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$249,000

Versatility is the name of the game with this turnkey Five-bedroom, two-and-three-quarter-bath property that wears many hats beautifully. Whether you're dreaming of a spacious single-family residence, a multi-family income generator, or a thriving short-term rental venture, the flexibility here is genuinely rare—and the heavy lifting has already been done for you. Move right in without lifting a paintbrush. Everything is ready to go, which means you can start living, hosting, or earning from day one. The proven vacation-rental potential makes this an especially smart play for buyers who appreciate a property that pays its own way while you enjoy the perks of Vermont ownership. Step outside and the appeal only deepens. A generous lot offers room to garden, gather, or simply breathe, while convenient parking keeps everyday comings and goings refreshingly hassle-free. At a price point designed to turn heads, this is the kind of value that makes savvy shoppers do a double take. Location seals the deal. Pine Hill Park sits practically around the corner, rewarding hikers and bikers with miles of wooded trails. Golfers can tee off at the nearby Rutland Country Club, and peace of mind comes easy with Rutland Regional Medical Center close by. When winter arrives, the legendary slopes of Killington Resort are roughly twenty minutes away, and the local train station keeps regional travel simple. Opportunity, comfort, and income potential rarely arrive in one tidy package—so seize the moment and schedule your showing today.

5098199 MLS

Versatility is the name of the game with this turnkey Five-bedroom, two-and-three-quarter-bath property that wears many hats beautifully. Whether you're dreaming of a spacious single-family residence, a multi-family income generator, or a thriving short-term rental venture, the flexibility here is genuinely rare—and the heavy lifting has already been done for you. Move right in without lifting a paintbrush. Everything is ready to go, which means you can start living, hosting, or earning from day one. The proven vacation-rental potential makes this an especially smart play for buyers who appreciate a property that pays its own way while you enjoy the perks of Vermont ownership. Step outside and the appeal only deepens. A generous lot offers room to garden, gather, or simply breathe, while convenient parking keeps everyday comings and goings refreshingly hassle-free. At a price point designed to turn heads, this is the kind of value that makes savvy shoppers do a double take. Location seals the deal. Pine Hill Park sits practically around the corner, rewarding hikers and bikers with miles of wooded trails. Golfers can tee off at the nearby Rutland Country Club, and peace of mind comes easy with Rutland Regional Medical Center close by. When winter arrives, the legendary slopes of Killington Resort are roughly twenty minutes away, and the local train station keeps regional travel simple. Opportunity, comfort, and income potential rarely arrive in one tidy package—so seize the moment and schedule your showing today.

292 West St, Rutland City

$435,000

Tucked into the rolling Wallingford countryside, this three-bedroom, two-bathroom home proves that spacious living and rural serenity can happily coexist on one generous lot. Inside, the newer kitchen anchors the home with fresh finishes showcasing Quartz countertops. A pellet stove was added in the living room to provide an extra heat source in the winters. Three efficient heat pumps keep every corner comfortable across all four Vermont seasons. One level living, three bedrooms and full bath complete the main flor. The lower level was completed to offer flexible bonus space that adapts to your needs—home office, playroom, studio, a hobby you keep promising to start. Step outside and the real showstopper appears: a sprawling 700-square-foot TimberTech deck built for lazy mornings and lively gatherings envelopes the Craven above-ground pool and a sizable barn wired with fifty-amp electric stands ready for workshops, storage, toys, or big-dream projects. The expansive rolling lawn that leads to the creek in the far back of the property; delivering breathing room that suburban lots simply can't match. Location seals the appeal. Elfin Lake sits just up the road for paddling and picnicking, while the trails of White Rocks National Recreation Area reward every hiker and nature lover nearby. Families appreciate proximity to Mill River Union High School, and powder chasers will love that Killington Ski Area is a scenic drive away.

3 Beds ⋅ 2 Baths ⋅ 5098161 MLS

Tucked into the rolling Wallingford countryside, this three-bedroom, two-bathroom home proves that spacious living and rural serenity can happily coexist on one generous lot. Inside, the newer kitchen anchors the home with fresh finishes showcasing Quartz countertops. A pellet stove was added in the living room to provide an extra heat source in the winters. Three efficient heat pumps keep every corner comfortable across all four Vermont seasons. One level living, three bedrooms and full bath complete the main flor. The lower level was completed to offer flexible bonus space that adapts to your needs—home office, playroom, studio, a hobby you keep promising to start. Step outside and the real showstopper appears: a sprawling 700-square-foot TimberTech deck built for lazy mornings and lively gatherings envelopes the Craven above-ground pool and a sizable barn wired with fifty-amp electric stands ready for workshops, storage, toys, or big-dream projects. The expansive rolling lawn that leads to the creek in the far back of the property; delivering breathing room that suburban lots simply can't match. Location seals the appeal. Elfin Lake sits just up the road for paddling and picnicking, while the trails of White Rocks National Recreation Area reward every hiker and nature lover nearby. Families appreciate proximity to Mill River Union High School, and powder chasers will love that Killington Ski Area is a scenic drive away.

470 Creek Rd, Wallingford

$599,000

Some properties simply have to be experienced in person to be fully appreciated, and this is one of them. This charming 3-bedroom, 2.5-bath Cape sits on 17 breathtaking acres where sweeping views, a spring fed pond, mature fruit trees, blueberry bushes, and beautifully maintained grounds create an exceptional setting. The property also includes two outbuildings, including a classic barn with hayloft and stalls. A second outbuilding features upper- and lower-level garage bays, ideal for equipment, ATVs, tractors, workshop space, or additional storage. Inside, the eat-in kitchen features a large picture window overlooking western views and stunning sunsets. It flows into the living room with a cozy wood-burning fireplace and sliding glass doors leading to the back porch, the perfect spot to enjoy the sunrise. A half bath with laundry is located just off the kitchen, while the first-floor primary suite offers a walk-in closet and private en suite bath. Upstairs are two generously sized bedrooms, each with a closet, and an additional full bath. The walk-out basement offers excellent potential for future expansion and already includes a roughed-in bathroom. A two-car attached garage completes the home. Enjoy the tranquility of country living without sacrificing convenience. Located just outside of Rutland, the property is close to shopping, dining, and healthcare, and only 30 minutes from Okemo and Killington/Pico for year-round recreation.

3 Beds ⋅ 3 Baths ⋅ 5098079 MLS

Some properties simply have to be experienced in person to be fully appreciated, and this is one of them. This charming 3-bedroom, 2.5-bath Cape sits on 17 breathtaking acres where sweeping views, a spring fed pond, mature fruit trees, blueberry bushes, and beautifully maintained grounds create an exceptional setting. The property also includes two outbuildings, including a classic barn with hayloft and stalls. A second outbuilding features upper- and lower-level garage bays, ideal for equipment, ATVs, tractors, workshop space, or additional storage. Inside, the eat-in kitchen features a large picture window overlooking western views and stunning sunsets. It flows into the living room with a cozy wood-burning fireplace and sliding glass doors leading to the back porch, the perfect spot to enjoy the sunrise. A half bath with laundry is located just off the kitchen, while the first-floor primary suite offers a walk-in closet and private en suite bath. Upstairs are two generously sized bedrooms, each with a closet, and an additional full bath. The walk-out basement offers excellent potential for future expansion and already includes a roughed-in bathroom. A two-car attached garage completes the home. Enjoy the tranquility of country living without sacrificing convenience. Located just outside of Rutland, the property is close to shopping, dining, and healthcare, and only 30 minutes from Okemo and Killington/Pico for year-round recreation.

2086 Walker Mountain Rd, Clarendon

$499,995

Welcome to Moon Ridge 2B. This renovated 3-level town home offers 2 bedrooms plus bonus room and 3 bathrooms. Tucked away just off Killington Road, this condo provides both comfort and ease. Imagine sipping apres on the deck outside the living room or relaxing on the couch while listening to the crackle of the wood burning fireplace, all while being minutes to everything that Killington has to offer. The generously sized primary bedroom has 2 large closets, an abundance of sunshine and a private deck offering beautiful views of both Killington and Pico. Enjoy cooking in the tastefully designed kitchen offering stainless steel appliances, granite counter tops and cherry cabinets. The lower level renovation allows for guests to have their own space, complete with living room, bathroom and wet bar. The common area space on the back side of the unit is great for entertaining. This home is a must see. Schedule your showing today.

2 Beds ⋅ 3 Baths ⋅ 5098037 MLS

Welcome to Moon Ridge 2B. This renovated 3-level town home offers 2 bedrooms plus bonus room and 3 bathrooms. Tucked away just off Killington Road, this condo provides both comfort and ease. Imagine sipping apres on the deck outside the living room or relaxing on the couch while listening to the crackle of the wood burning fireplace, all while being minutes to everything that Killington has to offer. The generously sized primary bedroom has 2 large closets, an abundance of sunshine and a private deck offering beautiful views of both Killington and Pico. Enjoy cooking in the tastefully designed kitchen offering stainless steel appliances, granite counter tops and cherry cabinets. The lower level renovation allows for guests to have their own space, complete with living room, bathroom and wet bar. The common area space on the back side of the unit is great for entertaining. This home is a must see. Schedule your showing today.

321 Moon Ridge Rd Unit 2B, Killington

$60,000

Village Home with Restoration Potential Set in a charming village location, this spacious 4 bedroom, 3 bath home is ready for restoration and offers endless potential. Featuring classic architectural details and a traditional layout, this property awaits your vision to bring it back to life. A detached garage provides convenient storage or workshop space. Located close to local shops, schools, and village amenities. This is a wonderful opportunity to create your dream home in a desirable setting. Property being conveyed "as is" with no warranties or guarantees.

4 Beds ⋅ 3 Baths ⋅ 5097982 MLS

Village Home with Restoration Potential Set in a charming village location, this spacious 4 bedroom, 3 bath home is ready for restoration and offers endless potential. Featuring classic architectural details and a traditional layout, this property awaits your vision to bring it back to life. A detached garage provides convenient storage or workshop space. Located close to local shops, schools, and village amenities. This is a wonderful opportunity to create your dream home in a desirable setting. Property being conveyed "as is" with no warranties or guarantees.

44 E Main St, Poultney

$848,000

Don’t miss a rare opportunity to own a stunning private retreat on a quiet cul-de-sac in one of Killington’s most desirable neighborhoods. Zoned a 4-bedroom residence, currently enjoyed as a 3-bed, 1.75-bath w/attached 2-car garage and attic storage above. Beautiful finishes throughout: vaulted ceilings, hardwood floors, updated carpeting, updated baths, newer appliances, custom kitchen cabinetry, woodwork & tilework. New roof December 2025. Outdoor living shines here. 2 beautiful patios and an expansive deck create a wonderful space for entertaining, relaxing, overlooking a wonderfully private backyard. Enjoy miles of Sherburne mountain bike Trails on the adjacent Green Mountain National Forest conservation land. Walk directly from your backyard to Kent Pond. Just 2 minutes from to Green Mountain National Golf, 1 mile from Killington Road. Bonus: a spacious two-story barn offers 672 square ft of flexible space, complete with full electrical service—ideal for a woodshop, art studio, hobby space, gym, or generous storage capacity. After a day outdoors on the adjacent trails, kayaking on Kent Pond, or enjoying the slopes at Killington resort, relax and unwind in the outdoor 8’ x 8’ 6-person Jacuzzi hot tub. Enjoy fireplace & woodstove on winter nights. Work from a sun-filled office, Xfinity gigabyte available. Whole house generator and a circular driveway! A rare blend of privacy, recreation, & convenience in the heart of Killington. Call today for more info.

4 Beds ⋅ 2 Baths ⋅ 5097967 MLS

Don’t miss a rare opportunity to own a stunning private retreat on a quiet cul-de-sac in one of Killington’s most desirable neighborhoods. Zoned a 4-bedroom residence, currently enjoyed as a 3-bed, 1.75-bath w/attached 2-car garage and attic storage above. Beautiful finishes throughout: vaulted ceilings, hardwood floors, updated carpeting, updated baths, newer appliances, custom kitchen cabinetry, woodwork & tilework. New roof December 2025. Outdoor living shines here. 2 beautiful patios and an expansive deck create a wonderful space for entertaining, relaxing, overlooking a wonderfully private backyard. Enjoy miles of Sherburne mountain bike Trails on the adjacent Green Mountain National Forest conservation land. Walk directly from your backyard to Kent Pond. Just 2 minutes from to Green Mountain National Golf, 1 mile from Killington Road. Bonus: a spacious two-story barn offers 672 square ft of flexible space, complete with full electrical service—ideal for a woodshop, art studio, hobby space, gym, or generous storage capacity. After a day outdoors on the adjacent trails, kayaking on Kent Pond, or enjoying the slopes at Killington resort, relax and unwind in the outdoor 8’ x 8’ 6-person Jacuzzi hot tub. Enjoy fireplace & woodstove on winter nights. Work from a sun-filled office, Xfinity gigabyte available. Whole house generator and a circular driveway! A rare blend of privacy, recreation, & convenience in the heart of Killington. Call today for more info.

218 Lakewood Dr, Killington

$335,000

Own a piece of history with this beautifully renovated duplex that perfectly blends timeless character with modern updates. Situated on a desirable .71 dead-end corner lot, this exceptional property also features a detached two-car garage and offers the ideal opportunity for both homeowners and investors alike. Live in one unit and rent the other to help offset your mortgage, or add this turnkey property to your investment portfolio. Each side-by-side unit is a mirror image of the other, offering a functional layout with a spacious living room, dining area, and updated kitchen on the main level. Upstairs, you'll find two comfortable bedrooms and one bathroom in each unit. One unit also boasts incredible walk-up attic access, presenting endless possibilities. Finish the space into a home office, playroom, guest suite, hobby room, or simply enjoy the abundance of storage. Whether you're looking for owner-occupied income, a multigenerational living arrangement, or a fully renovated investment property, this duplex checks all the boxes. **Second unit is under construction and set to be finished end of August

5097909 MLS

Own a piece of history with this beautifully renovated duplex that perfectly blends timeless character with modern updates. Situated on a desirable .71 dead-end corner lot, this exceptional property also features a detached two-car garage and offers the ideal opportunity for both homeowners and investors alike. Live in one unit and rent the other to help offset your mortgage, or add this turnkey property to your investment portfolio. Each side-by-side unit is a mirror image of the other, offering a functional layout with a spacious living room, dining area, and updated kitchen on the main level. Upstairs, you'll find two comfortable bedrooms and one bathroom in each unit. One unit also boasts incredible walk-up attic access, presenting endless possibilities. Finish the space into a home office, playroom, guest suite, hobby room, or simply enjoy the abundance of storage. Whether you're looking for owner-occupied income, a multigenerational living arrangement, or a fully renovated investment property, this duplex checks all the boxes. **Second unit is under construction and set to be finished end of August

48-50 Taylor Hill Rd, Proctor

$679,000

Some know it as the Bow House, others call it the Acorn House, but perhaps it's time to call it home. Rich in charm and character, this distinctive residence draws inspiration from the rare New England bow roof tradition, a style rooted in Maritime craftsmanship and celebrated for its graceful curved roofline. Originally influenced by the techniques of shipwrights and carpenters who built wooden boat hulls, the design creates a striking silhouette while maximizing headroom and living space on the second floor. The sweeping ceilings lend an openness that sets this home apart from more conventional New England houses. Thoughtfully updated for modern living, the current owners added a 1st flr primary suite that blends seamlessly with the original architecture, creating a home that's as functional as it is beautiful. Central A/C & heat pumps provides year-round comfort, while a woodstove in the kitchen and a pellet stove in the basement add warmth and inviting ambiance during Vermont's cooler months. Privately tucked away from the road, yet right in the heart of town, the property offers the best of both worlds. The oversized three-car garage provides exceptional space for vehicles, hobbies, or storage, and the dry basement offers even more room for organization. For buyers who appreciate homes with authentic character, thoughtful craftsmanship, and architectural significance, this is a rare opportunity. Equally appealing is its location in the heart of Brandon, one of Vermont's most vibrant villages, where galleries, studios, live performances, locally owned shops, cafés, and community events create a lively arts scene and a welcoming sense of place. Enjoy the convenience of village living while becoming part of a creative community that celebrates both history and culture. Homes with this level of architectural distinction and timeless charm seldom become available. This is more than a place to live,it's an opportunity to own a truly memorable piece of Vermont.

3 Beds ⋅ 3 Baths ⋅ 5097890 MLS

Some know it as the Bow House, others call it the Acorn House, but perhaps it's time to call it home. Rich in charm and character, this distinctive residence draws inspiration from the rare New England bow roof tradition, a style rooted in Maritime craftsmanship and celebrated for its graceful curved roofline. Originally influenced by the techniques of shipwrights and carpenters who built wooden boat hulls, the design creates a striking silhouette while maximizing headroom and living space on the second floor. The sweeping ceilings lend an openness that sets this home apart from more conventional New England houses. Thoughtfully updated for modern living, the current owners added a 1st flr primary suite that blends seamlessly with the original architecture, creating a home that's as functional as it is beautiful. Central A/C & heat pumps provides year-round comfort, while a woodstove in the kitchen and a pellet stove in the basement add warmth and inviting ambiance during Vermont's cooler months. Privately tucked away from the road, yet right in the heart of town, the property offers the best of both worlds. The oversized three-car garage provides exceptional space for vehicles, hobbies, or storage, and the dry basement offers even more room for organization. For buyers who appreciate homes with authentic character, thoughtful craftsmanship, and architectural significance, this is a rare opportunity. Equally appealing is its location in the heart of Brandon, one of Vermont's most vibrant villages, where galleries, studios, live performances, locally owned shops, cafés, and community events create a lively arts scene and a welcoming sense of place. Enjoy the convenience of village living while becoming part of a creative community that celebrates both history and culture. Homes with this level of architectural distinction and timeless charm seldom become available. This is more than a place to live,it's an opportunity to own a truly memorable piece of Vermont.

7 High St, Brandon

$740,000

A RARE combination of unspoiled forest (last cut in the 1960's), long road frontage, accessible terrain, and LOCATION! Multiple potential homesites (two easy-to-develop sites already soil tested) with View potential. Outdoors Lovers will appreciate that the Killington Resort and Town Recreation Area, state parks & accessible ponds, two golf courses, and National Forest are ALL only Minutes away! This 122+/- Acres lies East of Rt. 100 and North of River Road. The Tract enjoys 2/3rds mile of maintained road frontage. A recent Forester evaluation reports there is significant timber value. A Soil Test Report is available. Another adjacent 52 acres with two homesites and Ottaqueche riverfront may also be available for $250,000 (MLS #509885).

5097867 MLS

A RARE combination of unspoiled forest (last cut in the 1960's), long road frontage, accessible terrain, and LOCATION! Multiple potential homesites (two easy-to-develop sites already soil tested) with View potential. Outdoors Lovers will appreciate that the Killington Resort and Town Recreation Area, state parks & accessible ponds, two golf courses, and National Forest are ALL only Minutes away! This 122+/- Acres lies East of Rt. 100 and North of River Road. The Tract enjoys 2/3rds mile of maintained road frontage. A recent Forester evaluation reports there is significant timber value. A Soil Test Report is available. Another adjacent 52 acres with two homesites and Ottaqueche riverfront may also be available for $250,000 (MLS #509885).

00 Vt Route 100 & River Road, Killington

$1,250,000

It’s hard to say which season you’ll enjoy most in this exceptional 4-bedroom, 5-bath fully furnished and equipped custom-built home, privately set on ten acres comprised of two separate 5-acre lots, with the lower lot offering possible development opportunities. Located in an established neighborhood with protective covenants that preserve both value and tranquility, this thoughtfully designed home showcases true pride of ownership with real wood finishes, detailed millwork, and quality materials throughout, offering a level of warmth and character that’s increasingly rare. Located on sought-after Cricket Hill Road in Killington, the property is perfectly positioned for year-round recreation, just a mile from Green Mountain National Golf Course and only ten minutes from Killington Resort. Yet despite its convenience, the setting feels worlds away, with sweeping long-range mountain views creating a stunning backdrop in every season. Inside and out, the home is designed for comfort and connection to nature. In the warmer months, relax by the pool while listening to the soothing sounds of a nearby waterfall feature tucked into the greenhouse, surrounded by mature landscaping and vibrant gardens. The property’s private pond and outdoor hot tub offer additional spaces to unwind, entertain, and enjoy the peaceful surroundings. As winter arrives, take in panoramic views of snow-covered peaks, including Pico Mountain, before heading out to nearby ski areas or returning home to the serenity of your mountain retreat. The craftsmanship continues throughout the interior, where inviting living spaces and fine details create a cozy yet refined atmosphere. A well-appointed in-law apartment above the attached two-car garage provides both interior and private exterior access, making it ideal for guests or extended family seeking independence without sacrificing comfort. Call today to book your private showing for this unique opportunity.

4 Beds ⋅ 5 Baths ⋅ 5097823 MLS

It’s hard to say which season you’ll enjoy most in this exceptional 4-bedroom, 5-bath fully furnished and equipped custom-built home, privately set on ten acres comprised of two separate 5-acre lots, with the lower lot offering possible development opportunities. Located in an established neighborhood with protective covenants that preserve both value and tranquility, this thoughtfully designed home showcases true pride of ownership with real wood finishes, detailed millwork, and quality materials throughout, offering a level of warmth and character that’s increasingly rare. Located on sought-after Cricket Hill Road in Killington, the property is perfectly positioned for year-round recreation, just a mile from Green Mountain National Golf Course and only ten minutes from Killington Resort. Yet despite its convenience, the setting feels worlds away, with sweeping long-range mountain views creating a stunning backdrop in every season. Inside and out, the home is designed for comfort and connection to nature. In the warmer months, relax by the pool while listening to the soothing sounds of a nearby waterfall feature tucked into the greenhouse, surrounded by mature landscaping and vibrant gardens. The property’s private pond and outdoor hot tub offer additional spaces to unwind, entertain, and enjoy the peaceful surroundings. As winter arrives, take in panoramic views of snow-covered peaks, including Pico Mountain, before heading out to nearby ski areas or returning home to the serenity of your mountain retreat. The craftsmanship continues throughout the interior, where inviting living spaces and fine details create a cozy yet refined atmosphere. A well-appointed in-law apartment above the attached two-car garage provides both interior and private exterior access, making it ideal for guests or extended family seeking independence without sacrificing comfort. Call today to book your private showing for this unique opportunity.

838 Cricket Hill Rd, Killington

$465,000

Rarely available and ideally situated within The Woods Resort & Spa, this updated, furnished, south-facing end-unit condo combines abundant natural light, exceptional privacy, direct patio access to the outdoors, and one of the community's closest locations to the spa and fitness center. Whether you're searching for a weekend ski retreat, a 4-season mountain getaway, or a low-maintenance Vermont home, this move-in-ready 2-bedroom, 2-bath condo offers the perfect balance of comfort, convenience, and lifestyle. The additional windows unique to this end unit, fill the home with natural light throughout the day, while Karndean luxury vinyl plank flooring provides the warmth and beauty of hardwood with exceptional durability after a day of skiing, hiking, mountain biking, golfing, or exploring everything the Killington region has to offer. The updated kitchen features modern appliances and flows seamlessly into the dining area and inviting living room. A classic wood-burning fireplace creates the perfect place to gather after a day on the mountain, while sliding glass doors open to a private patio overlooking The Woods' beautifully maintained clay tennis courts. Owners enjoy access to the courts, and the open green space beyond the patio creates a peaceful setting for morning coffee, outdoor dining, or simply relaxing and taking in the fresh Vermont air. One of the home's most desirable features is its direct patio access to the lawn. The patio opens directly to the outdoors, making it especially convenient for dog owners, children, or anyone who appreciates easy access to green space. The primary suite features an updated en-suite bath with a glass walk-in shower, while the second bedroom and full bath provide comfortable accommodations for family and guests. Just steps away, owners enjoy access to The Woods Spa, featuring an indoor pool, hot tub, sauna, steam room, fitness center, and locker rooms all included in the monthly condo fee. Call now to see this property

2 Beds ⋅ 2 Baths ⋅ 5097799 MLS

Rarely available and ideally situated within The Woods Resort & Spa, this updated, furnished, south-facing end-unit condo combines abundant natural light, exceptional privacy, direct patio access to the outdoors, and one of the community's closest locations to the spa and fitness center. Whether you're searching for a weekend ski retreat, a 4-season mountain getaway, or a low-maintenance Vermont home, this move-in-ready 2-bedroom, 2-bath condo offers the perfect balance of comfort, convenience, and lifestyle. The additional windows unique to this end unit, fill the home with natural light throughout the day, while Karndean luxury vinyl plank flooring provides the warmth and beauty of hardwood with exceptional durability after a day of skiing, hiking, mountain biking, golfing, or exploring everything the Killington region has to offer. The updated kitchen features modern appliances and flows seamlessly into the dining area and inviting living room. A classic wood-burning fireplace creates the perfect place to gather after a day on the mountain, while sliding glass doors open to a private patio overlooking The Woods' beautifully maintained clay tennis courts. Owners enjoy access to the courts, and the open green space beyond the patio creates a peaceful setting for morning coffee, outdoor dining, or simply relaxing and taking in the fresh Vermont air. One of the home's most desirable features is its direct patio access to the lawn. The patio opens directly to the outdoors, making it especially convenient for dog owners, children, or anyone who appreciates easy access to green space. The primary suite features an updated en-suite bath with a glass walk-in shower, while the second bedroom and full bath provide comfortable accommodations for family and guests. Just steps away, owners enjoy access to The Woods Spa, featuring an indoor pool, hot tub, sauna, steam room, fitness center, and locker rooms all included in the monthly condo fee. Call now to see this property

151 Village Cir Unit V31, Killington

$898,000

Offered for the first time by its original owner, this distinguished Killington Basin residence was thoughtfully designed and built by renowned Roaring Brook Constructors, Killington’s award-winning design/build firm. The property offers an expansive backyard with two decks to enjoy nature. Set within the sought-after Telefon Trail neighborhood, the property offers exceptional access to the lifts and the acclaimed dining along Killington Road. Inside, the layout connects the living spaces with ease, while an oversized heated two-car garage adds comfort and convenience through Vermont’s winter season. The expansive primary suite features a walk-in closet and a well-appointed private bath with double sinks, a whirlpool tub, and a separate stall shower. A secondary suite provides its own walk-in closet and direct access to a shared bath. The cupola set in the middle of the house brings in natural light. Nicely landscaped with expansive lawns, flower gardens, crab apple trees, evergreens and red maples. Sale is subject to Sellers finding suitable housing prior to closing. Seller is a licensed real estate broker.

3 Beds ⋅ 3 Baths ⋅ 5097766 MLS

Offered for the first time by its original owner, this distinguished Killington Basin residence was thoughtfully designed and built by renowned Roaring Brook Constructors, Killington’s award-winning design/build firm. The property offers an expansive backyard with two decks to enjoy nature. Set within the sought-after Telefon Trail neighborhood, the property offers exceptional access to the lifts and the acclaimed dining along Killington Road. Inside, the layout connects the living spaces with ease, while an oversized heated two-car garage adds comfort and convenience through Vermont’s winter season. The expansive primary suite features a walk-in closet and a well-appointed private bath with double sinks, a whirlpool tub, and a separate stall shower. A secondary suite provides its own walk-in closet and direct access to a shared bath. The cupola set in the middle of the house brings in natural light. Nicely landscaped with expansive lawns, flower gardens, crab apple trees, evergreens and red maples. Sale is subject to Sellers finding suitable housing prior to closing. Seller is a licensed real estate broker.

265 Telefon Trl, Killington

$300,000

NEW PRICE $300K A rare opportunity to own a historic 157-year-old property situated on 4.48 acres in Rutland City. Rich in character and history, this spacious residence offers the charm and architectural appeal of a bygone era while benefiting from valuable Industrial zoning, creating unique possibilities for investment, redevelopment, or business use (subject to City approvals and permitted uses). The home, constructed in 1869, features a total of fourteen rooms. The first level includes two bedrooms, one bath, a kitchen, living room, and dining room. The second level offers four bedrooms, one bath, a kitchenette, dining room, and two other rooms. Enclosed porches on both levels. A detached classic carriage barn with workshop space and a second floor adds versatility for storage, or future use. The expansive 4.48-acre parcel provides open space, and room for future planning, all while enjoying a convenient city location with easy access to downtown, major roadways, and employment centers. The property retains much of its original character but will require a complete remodel and updating. Interior components are dated, and buyers should be aware of known conditions affecting the property, including knob-and-tube wiring, insulated piping in the basement, and evidence of prior ceiling leaks. Buyers are encouraged to conduct their own inspections and due diligence regarding the property's condition. Located within an Industrial zoning district, the property offers substantial potential beyond its current residential use. Buyers are strongly encouraged to consult with the City of Rutland Planning & Zoning Department regarding permitted and conditional uses.This property is being conveyed in as-is condition, including all remaining contents. Whether you're seeking a distinctive historic home, a live/work opportunity, or a property with outstanding long-term redevelopment potential, this offering presents a rare combination of history, acreage and future possibilities.

6 Beds ⋅ 2 Baths ⋅ 5097658 MLS

NEW PRICE $300K A rare opportunity to own a historic 157-year-old property situated on 4.48 acres in Rutland City. Rich in character and history, this spacious residence offers the charm and architectural appeal of a bygone era while benefiting from valuable Industrial zoning, creating unique possibilities for investment, redevelopment, or business use (subject to City approvals and permitted uses). The home, constructed in 1869, features a total of fourteen rooms. The first level includes two bedrooms, one bath, a kitchen, living room, and dining room. The second level offers four bedrooms, one bath, a kitchenette, dining room, and two other rooms. Enclosed porches on both levels. A detached classic carriage barn with workshop space and a second floor adds versatility for storage, or future use. The expansive 4.48-acre parcel provides open space, and room for future planning, all while enjoying a convenient city location with easy access to downtown, major roadways, and employment centers. The property retains much of its original character but will require a complete remodel and updating. Interior components are dated, and buyers should be aware of known conditions affecting the property, including knob-and-tube wiring, insulated piping in the basement, and evidence of prior ceiling leaks. Buyers are encouraged to conduct their own inspections and due diligence regarding the property's condition. Located within an Industrial zoning district, the property offers substantial potential beyond its current residential use. Buyers are strongly encouraged to consult with the City of Rutland Planning & Zoning Department regarding permitted and conditional uses.This property is being conveyed in as-is condition, including all remaining contents. Whether you're seeking a distinctive historic home, a live/work opportunity, or a property with outstanding long-term redevelopment potential, this offering presents a rare combination of history, acreage and future possibilities.

45 Park St, Rutland City

$599,000

Build your dream home on this beautiful 114-acre wooded parcel in Clarendon, Vermont. A cleared building site offers breathtaking mountain views, and a state wastewater permit is already in place for a 4-bedroom home. A roughed-in access road leads to the building site. Enjoy the privacy and recreation that comes with 114 acres of mostly wooded land, while being just outside of Rutland for convenient access to shopping, dining, healthcare, and everyday amenities. Located just 30 minutes from Manchester, Killington/Pico and Okemo, this property offers the perfect balance of seclusion, convenience, and year-round outdoor adventure. Owner financing is available, offering added flexibility for buyers.

5097649 MLS

Build your dream home on this beautiful 114-acre wooded parcel in Clarendon, Vermont. A cleared building site offers breathtaking mountain views, and a state wastewater permit is already in place for a 4-bedroom home. A roughed-in access road leads to the building site. Enjoy the privacy and recreation that comes with 114 acres of mostly wooded land, while being just outside of Rutland for convenient access to shopping, dining, healthcare, and everyday amenities. Located just 30 minutes from Manchester, Killington/Pico and Okemo, this property offers the perfect balance of seclusion, convenience, and year-round outdoor adventure. Owner financing is available, offering added flexibility for buyers.

3393 Creek Rd, Clarendon

$374,900

Welcome to your peaceful Vermont retreat! This is a property you must see to really appreciate! Pictures cannot capture the pure peice and quiet on 5.6 wooded acres. This well-maintained 3-bedroom, 2-bath home offers approximately 2,200 square feet of comfortable living space with the perfect balance of privacy, space, and convenience. Inside, you'll find a spacious and functional layout with generous living areas, abundant natural light, and endless potential to make it your own. The kitchen offers ample workspace and is ready for your personal updates, while the home's thoughtful floor plan is ideal for both everyday living and entertaining. Recent energy-efficient upgrades include four mini-split heat pumps for year-round heating and cooling, a heat pump water heater providing comfort, efficiency, and peace of mind. Outside, enjoy the beauty of open space with room for gardening, recreation, animals, or simply relaxing while taking in the peaceful surroundings. Whether you're looking for a private home with acreage, hobby farm potential, or a quiet country escape, this property offers endless possibilities. Conveniently located just minutes from local amenities while still offering the tranquility of rural living, this exceptional property is listed at $374,900 accepting offers. Seller will offer concessions to buyer

3 Beds ⋅ 2 Baths ⋅ 5097536 MLS

Welcome to your peaceful Vermont retreat! This is a property you must see to really appreciate! Pictures cannot capture the pure peice and quiet on 5.6 wooded acres. This well-maintained 3-bedroom, 2-bath home offers approximately 2,200 square feet of comfortable living space with the perfect balance of privacy, space, and convenience. Inside, you'll find a spacious and functional layout with generous living areas, abundant natural light, and endless potential to make it your own. The kitchen offers ample workspace and is ready for your personal updates, while the home's thoughtful floor plan is ideal for both everyday living and entertaining. Recent energy-efficient upgrades include four mini-split heat pumps for year-round heating and cooling, a heat pump water heater providing comfort, efficiency, and peace of mind. Outside, enjoy the beauty of open space with room for gardening, recreation, animals, or simply relaxing while taking in the peaceful surroundings. Whether you're looking for a private home with acreage, hobby farm potential, or a quiet country escape, this property offers endless possibilities. Conveniently located just minutes from local amenities while still offering the tranquility of rural living, this exceptional property is listed at $374,900 accepting offers. Seller will offer concessions to buyer

852 Boardman Hill Rd, West Rutland

$193,600

Seasonal summer cottage that sits right on Lake Hortonia and it can be your summer retreat. There is a forced hot air gas furnace that has been hooked up to extend your seasons. There is a deck upstairs and an enclosed porch down. Also provided is a Lopi wood stove for extra cozy warmth. This cottage has 65 ft of direct lake frontage. 2 upper bedrooms with a downstairs 3/4 bath. Enjoy boating on picturesque quiet Lake Hortonia which is 2 miles long with 22 miles of shoreline and eleven Islands. Excellent fishing. 2 Sheds COMBINED in center for storage. Same family has enjoyed this cottage for 28 years and it is time for new owners to put their finishing touches on it.

2 Beds ⋅ 1 Baths ⋅ 5097525 MLS

Seasonal summer cottage that sits right on Lake Hortonia and it can be your summer retreat. There is a forced hot air gas furnace that has been hooked up to extend your seasons. There is a deck upstairs and an enclosed porch down. Also provided is a Lopi wood stove for extra cozy warmth. This cottage has 65 ft of direct lake frontage. 2 upper bedrooms with a downstairs 3/4 bath. Enjoy boating on picturesque quiet Lake Hortonia which is 2 miles long with 22 miles of shoreline and eleven Islands. Excellent fishing. 2 Sheds COMBINED in center for storage. Same family has enjoyed this cottage for 28 years and it is time for new owners to put their finishing touches on it.

64 Tyminski Ln, Hubbardton

$249,500

Classic Vermont charm meets everyday comfort in this inviting Pittsford Village home, where original character, thoughtful updates, and a spacious backyard come together at an exceptional value. A welcoming covered front porch offers the perfect place to enjoy your morning coffee or unwind after a busy day. Step inside to discover original hardwood floors that add warmth and timeless appeal throughout much of the home. The comfortable living room is centered around a cozy wood stove, creating an inviting atmosphere during Vermont's colder months. The eat-in kitchen and formal dining room provide flexibility for both everyday living and entertaining, while a full bath with first-floor laundry adds convenience. Upstairs, three comfortable bedrooms and a second full bath offer space for family, guests, or a home office. The .38-acre lot features a spacious backyard with room for gardening, pets, play, or outdoor gatherings. Replacement windows, low-maintenance vinyl siding, and a standing-seam metal roof provide lasting durability and reduced maintenance. A detached garage and ample driveway parking complete the property. Ideally located in the heart of Pittsford Village, you'll enjoy walking to the Pittsford Recreation Area and Lothrop Elementary School, with local shops and amenities just minutes away. Rutland is only 15 minutes away, and Burlington International Airport is less than 90 minutes from home. Blending character, functionality, and value, this home offers an opportunity that's becoming increasingly difficult to find in today's market. Sale is subject to the sellers securing suitable housing. Relocation options have been identified, and a flexible closing timeline is available.

3 Beds ⋅ 2 Baths ⋅ 5097502 MLS

Classic Vermont charm meets everyday comfort in this inviting Pittsford Village home, where original character, thoughtful updates, and a spacious backyard come together at an exceptional value. A welcoming covered front porch offers the perfect place to enjoy your morning coffee or unwind after a busy day. Step inside to discover original hardwood floors that add warmth and timeless appeal throughout much of the home. The comfortable living room is centered around a cozy wood stove, creating an inviting atmosphere during Vermont's colder months. The eat-in kitchen and formal dining room provide flexibility for both everyday living and entertaining, while a full bath with first-floor laundry adds convenience. Upstairs, three comfortable bedrooms and a second full bath offer space for family, guests, or a home office. The .38-acre lot features a spacious backyard with room for gardening, pets, play, or outdoor gatherings. Replacement windows, low-maintenance vinyl siding, and a standing-seam metal roof provide lasting durability and reduced maintenance. A detached garage and ample driveway parking complete the property. Ideally located in the heart of Pittsford Village, you'll enjoy walking to the Pittsford Recreation Area and Lothrop Elementary School, with local shops and amenities just minutes away. Rutland is only 15 minutes away, and Burlington International Airport is less than 90 minutes from home. Blending character, functionality, and value, this home offers an opportunity that's becoming increasingly difficult to find in today's market. Sale is subject to the sellers securing suitable housing. Relocation options have been identified, and a flexible closing timeline is available.

268 Furnace Rd, Pittsford

$270,000

Step into the timeless charm of this picture-perfect 1925 Vermont country cottage, where character, comfort, and a lifetime of love come together. Offering 3 bedrooms, 1 full bath, and convenient first-floor laundry, this home is as inviting as it is functional. From the moment you arrive, you'll be captivated by the large screened-in front porch - the perfect place to enjoy your morning coffee or unwind while taking in the peaceful surroundings. Situated on a spacious corner lot, the property offers endless opportunities for gardening, raising chickens, or simply enjoying the outdoors. Complete with a charming chicken coop, gardening shed, oversized 2-car garage, and bonus storage space off the back of the garage, there's room for all your hobbies and projects. The backyard is truly something special, backing up to the Mill River and the picturesque Kingsley Mill Covered Bridge, creating a quintessential Vermont setting that's hard to find. Lovingly cared for by the same owners for the past 67 years, this home radiates warmth and pride of ownership. Their hearts and souls have been poured into every corner, creating a welcoming atmosphere you can feel the moment you walk through the door. Cute as can be and ready for its next chapter, this beloved cottage is waiting for someone new to make it home.

3 Beds ⋅ 1 Baths ⋅ 5097468 MLS

Step into the timeless charm of this picture-perfect 1925 Vermont country cottage, where character, comfort, and a lifetime of love come together. Offering 3 bedrooms, 1 full bath, and convenient first-floor laundry, this home is as inviting as it is functional. From the moment you arrive, you'll be captivated by the large screened-in front porch - the perfect place to enjoy your morning coffee or unwind while taking in the peaceful surroundings. Situated on a spacious corner lot, the property offers endless opportunities for gardening, raising chickens, or simply enjoying the outdoors. Complete with a charming chicken coop, gardening shed, oversized 2-car garage, and bonus storage space off the back of the garage, there's room for all your hobbies and projects. The backyard is truly something special, backing up to the Mill River and the picturesque Kingsley Mill Covered Bridge, creating a quintessential Vermont setting that's hard to find. Lovingly cared for by the same owners for the past 67 years, this home radiates warmth and pride of ownership. Their hearts and souls have been poured into every corner, creating a welcoming atmosphere you can feel the moment you walk through the door. Cute as can be and ready for its next chapter, this beloved cottage is waiting for someone new to make it home.

2875 East St, Clarendon

$249,000

Versatility is the name of the game with this turnkey four-bedroom, two-and-three-quarter-bath property that wears many hats beautifully. Whether you're dreaming of a spacious single-family residence, a multi-family income generator, or a thriving short-term rental venture, the flexibility here is genuinely rare—and the heavy lifting has already been done for you. Move right in without lifting a paintbrush. Everything is ready to go, which means you can start living, hosting, or earning from day one. The proven vacation-rental potential makes this an especially smart play for buyers who appreciate a property that pays its own way while you enjoy the perks of Vermont ownership. Step outside and the appeal only deepens. A generous lot offers room to garden, gather, or simply breathe, while convenient parking keeps everyday comings and goings refreshingly hassle-free. At a price point designed to turn heads, this is the kind of value that makes savvy shoppers do a double take. Location seals the deal. Pine Hill Park sits practically around the corner, rewarding hikers and bikers with miles of wooded trails. Golfers can tee off at the nearby Rutland Country Club, and peace of mind comes easy with Rutland Regional Medical Center close by. When winter arrives, the legendary slopes of Killington Resort are roughly twenty minutes away, and the local train station keeps regional travel simple. Opportunity, comfort, and income potential rarely arrive in one tidy package. Time to seize the moment and schedule your showing today. *294 West Street is also available for sale and both properties could be purchased together at a discounted price.

4 Beds ⋅ 4 Baths ⋅ 5097393 MLS

Versatility is the name of the game with this turnkey four-bedroom, two-and-three-quarter-bath property that wears many hats beautifully. Whether you're dreaming of a spacious single-family residence, a multi-family income generator, or a thriving short-term rental venture, the flexibility here is genuinely rare—and the heavy lifting has already been done for you. Move right in without lifting a paintbrush. Everything is ready to go, which means you can start living, hosting, or earning from day one. The proven vacation-rental potential makes this an especially smart play for buyers who appreciate a property that pays its own way while you enjoy the perks of Vermont ownership. Step outside and the appeal only deepens. A generous lot offers room to garden, gather, or simply breathe, while convenient parking keeps everyday comings and goings refreshingly hassle-free. At a price point designed to turn heads, this is the kind of value that makes savvy shoppers do a double take. Location seals the deal. Pine Hill Park sits practically around the corner, rewarding hikers and bikers with miles of wooded trails. Golfers can tee off at the nearby Rutland Country Club, and peace of mind comes easy with Rutland Regional Medical Center close by. When winter arrives, the legendary slopes of Killington Resort are roughly twenty minutes away, and the local train station keeps regional travel simple. Opportunity, comfort, and income potential rarely arrive in one tidy package. Time to seize the moment and schedule your showing today. *294 West Street is also available for sale and both properties could be purchased together at a discounted price.

292 West St, Rutland City

$239,000

Calling all investors and big-family dreamers—here's a five-bedroom, two-bathroom home that knows how to multiply its value. Better yet, it arrives as part of a smart investment package alongside the property next door, doubling your opportunity in one tidy transaction. Five generous bedrooms mean there's room for everyone and everything, whether you're housing a growing household or filling rooms with reliable tenants. With two full bathrooms keeping morning routines civilized, this layout balances livability with genuine income-generating muscle. The rental potential here speaks for itself, and the attractive price point makes the math even sweeter for buyers who like their numbers to add up. Beyond the front door, Rutland's lively scene unfolds. The historic downtown district sits just a short stroll away, where local shops, eateries, and that timeless New England character invite you to linger. Outdoor lovers will adore Pine Hill Park nearby, offering miles of wooded trails for hiking and biking. Peace of mind comes courtesy of Rutland Regional Medical Center, a quick drive down the road, while ski fanatics can chase fresh powder at legendary Killington Resort roughly fifteen minutes away. This is the kind of property that wears two hats with ease—comfortable home base or savvy revenue stream, the choice is yours. Pairing solid bones with a location that keeps tenants and families equally happy, the upside is hard to ignore. Opportunities bundled this neatly don't wait around. Schedule your private showing today. 292 West Street is also available for sale and both properties could be purchased together at a discounted price.

5 Beds ⋅ 2 Baths ⋅ 5097387 MLS

Calling all investors and big-family dreamers—here's a five-bedroom, two-bathroom home that knows how to multiply its value. Better yet, it arrives as part of a smart investment package alongside the property next door, doubling your opportunity in one tidy transaction. Five generous bedrooms mean there's room for everyone and everything, whether you're housing a growing household or filling rooms with reliable tenants. With two full bathrooms keeping morning routines civilized, this layout balances livability with genuine income-generating muscle. The rental potential here speaks for itself, and the attractive price point makes the math even sweeter for buyers who like their numbers to add up. Beyond the front door, Rutland's lively scene unfolds. The historic downtown district sits just a short stroll away, where local shops, eateries, and that timeless New England character invite you to linger. Outdoor lovers will adore Pine Hill Park nearby, offering miles of wooded trails for hiking and biking. Peace of mind comes courtesy of Rutland Regional Medical Center, a quick drive down the road, while ski fanatics can chase fresh powder at legendary Killington Resort roughly fifteen minutes away. This is the kind of property that wears two hats with ease—comfortable home base or savvy revenue stream, the choice is yours. Pairing solid bones with a location that keeps tenants and families equally happy, the upside is hard to ignore. Opportunities bundled this neatly don't wait around. Schedule your private showing today. 292 West Street is also available for sale and both properties could be purchased together at a discounted price.

294 West St, Rutland City

$929,000

This exceptional 3-bedroom, 2-bath home located on Dean Hill Road in Killington offers the perfect blend of comfortable mountain living, investment opportunity and year-round adventure access. Ideally positioned within walking distance of public transportation and just off The Killington Road, this fully furnished and equipped residence offers easy access to everything the region offers—skiing, snowboarding, mountain biking and more. Enjoy breathtaking views of Killington and Pico from inside the home, as well as from the private outdoor hot tub and the spacious deck. This property sits on a subdividable 1.9-acre lot, offering the flexibility to add an accessory dwelling unit (ADU) or expand in the future. The home features a generous 2-car garage with ample storage space, complemented by a detached storage shed with 2 levels, perfect for a workshop or additional gear storage. With the added benefit of public sewer and the potential for additional sewer units, this property provides a rare and versatile opportunity in the heart of Vermont's ski country. Call today for a private tour or more details.

3 Beds ⋅ 2 Baths ⋅ 5097372 MLS

This exceptional 3-bedroom, 2-bath home located on Dean Hill Road in Killington offers the perfect blend of comfortable mountain living, investment opportunity and year-round adventure access. Ideally positioned within walking distance of public transportation and just off The Killington Road, this fully furnished and equipped residence offers easy access to everything the region offers—skiing, snowboarding, mountain biking and more. Enjoy breathtaking views of Killington and Pico from inside the home, as well as from the private outdoor hot tub and the spacious deck. This property sits on a subdividable 1.9-acre lot, offering the flexibility to add an accessory dwelling unit (ADU) or expand in the future. The home features a generous 2-car garage with ample storage space, complemented by a detached storage shed with 2 levels, perfect for a workshop or additional gear storage. With the added benefit of public sewer and the potential for additional sewer units, this property provides a rare and versatile opportunity in the heart of Vermont's ski country. Call today for a private tour or more details.

325 Dean Hill Rd, Killington

$499,000

Investors, take note: here's a four unit multi-family property that pairs steady rental income with a prime uptown Rutland location—a combination savvy buyers rarely stumble upon. Built for performance, this well-maintained solid building features separate utilities across its units, meaning tenants cover their own usage and you sidestep the headache of dividing bills every month. The first floor spacious apartment also has use of the two car attached garage, three bedrooms and one level living. The second floor consist of (2) one bedroom units and a studio apartment with a private balcony. The fourth unit offers an abundance of natural light with built-in bookcases, a skylight and it's own access to a private garden at the back of the building. This layout accommodates multiple households comfortably, keeping occupancy strong and vacancies short. Whether you're an experienced landlord expanding your portfolio or a first-time investor dipping a toe into rental ownership, this property checks the practical boxes. The care that previous owners and the current owner has poured into upkeep shows, sparing you the surprise expenses that often plague older buildings. Simply put, it's ready to generate returns from the moment you collect the keys with a great rental history. Some newer heat pumps have been added for energy efficient heating. Location only sweetens the proposition. Tenants enjoy close proximity to Main Street Park, a pleasant green pocket perfect for lunch breaks and weekend lounging. Daily errands stay effortless with Shopping Plaza Road just minutes away, while Marble Valley Regional Transit puts car-free commuting within easy reach—a genuine selling point that keeps renters interested and leases signed. The bus also transports to Killington Ski area!

5097369 MLS

Investors, take note: here's a four unit multi-family property that pairs steady rental income with a prime uptown Rutland location—a combination savvy buyers rarely stumble upon. Built for performance, this well-maintained solid building features separate utilities across its units, meaning tenants cover their own usage and you sidestep the headache of dividing bills every month. The first floor spacious apartment also has use of the two car attached garage, three bedrooms and one level living. The second floor consist of (2) one bedroom units and a studio apartment with a private balcony. The fourth unit offers an abundance of natural light with built-in bookcases, a skylight and it's own access to a private garden at the back of the building. This layout accommodates multiple households comfortably, keeping occupancy strong and vacancies short. Whether you're an experienced landlord expanding your portfolio or a first-time investor dipping a toe into rental ownership, this property checks the practical boxes. The care that previous owners and the current owner has poured into upkeep shows, sparing you the surprise expenses that often plague older buildings. Simply put, it's ready to generate returns from the moment you collect the keys with a great rental history. Some newer heat pumps have been added for energy efficient heating. Location only sweetens the proposition. Tenants enjoy close proximity to Main Street Park, a pleasant green pocket perfect for lunch breaks and weekend lounging. Daily errands stay effortless with Shopping Plaza Road just minutes away, while Marble Valley Regional Transit puts car-free commuting within easy reach—a genuine selling point that keeps renters interested and leases signed. The bus also transports to Killington Ski area!

40 S Main St, Rutland City

$279,000

The Sycamore Inn — A Piece of Vermont History, Reimagined for Modern Living Rich in history and timeless appeal, The Sycamore Inn occupies part of the stately mid-1800s residence once known as the Governor's Mansion. Thoughtfully restored into a limited collection of condominium homes in the early 1980s, it preserves the craftsmanship and architectural character of its era while offering the comforts and conveniences of modern living. Opportunities to own within this iconic Rutland landmark are rare. Perfectly positioned on the first floor, Unit #2 offers both front and rear private entrances for everyday convenience. Step inside and be welcomed by soaring cathedral ceilings, remarkable period woodwork, and oversized windows that fill the home with natural light. Recently refinished hardwood floors extend throughout the main living areas, creating a warm and inviting atmosphere. The beautifully updated kitchen serves as the heart of the home, featuring an oversized granite island perfect for gathering, abundant cabinetry, space for a full dining table, and a striking arched built-in buffet that blends timeless character with everyday function. Two spacious bedrooms, a large full bath, and a private en suite half bath provide a comfortable and thoughtfully designed floor plan. Custom closet systems, abundant storage, an in-unit washer and dryer, and a fully enclosed private basement storage area offer conveniences rarely found in historic homes. Located in the heart of Rutland City, you'll enjoy the convenience of walking to downtown restaurants, shops, parks, and everyday services. Just a short drive away are Killington and Pico ski resorts, the lakes of Bomoseen and St. Catherine, scenic hiking trails, and year-round outdoor recreation that make Vermont living so desirable. Historic elegance. Modern convenience. A home with a story all its own. Schedule your private showing today—Be sure to ask for the property video. Open House Friday July 3rd, 1pm to 2:30pm

2 Beds ⋅ 2 Baths ⋅ 5097344 MLS

The Sycamore Inn — A Piece of Vermont History, Reimagined for Modern Living Rich in history and timeless appeal, The Sycamore Inn occupies part of the stately mid-1800s residence once known as the Governor's Mansion. Thoughtfully restored into a limited collection of condominium homes in the early 1980s, it preserves the craftsmanship and architectural character of its era while offering the comforts and conveniences of modern living. Opportunities to own within this iconic Rutland landmark are rare. Perfectly positioned on the first floor, Unit #2 offers both front and rear private entrances for everyday convenience. Step inside and be welcomed by soaring cathedral ceilings, remarkable period woodwork, and oversized windows that fill the home with natural light. Recently refinished hardwood floors extend throughout the main living areas, creating a warm and inviting atmosphere. The beautifully updated kitchen serves as the heart of the home, featuring an oversized granite island perfect for gathering, abundant cabinetry, space for a full dining table, and a striking arched built-in buffet that blends timeless character with everyday function. Two spacious bedrooms, a large full bath, and a private en suite half bath provide a comfortable and thoughtfully designed floor plan. Custom closet systems, abundant storage, an in-unit washer and dryer, and a fully enclosed private basement storage area offer conveniences rarely found in historic homes. Located in the heart of Rutland City, you'll enjoy the convenience of walking to downtown restaurants, shops, parks, and everyday services. Just a short drive away are Killington and Pico ski resorts, the lakes of Bomoseen and St. Catherine, scenic hiking trails, and year-round outdoor recreation that make Vermont living so desirable. Historic elegance. Modern convenience. A home with a story all its own. Schedule your private showing today—Be sure to ask for the property video. Open House Friday July 3rd, 1pm to 2:30pm

24 S Main St Unit 2, Rutland City

$949,000

Nestled in a picturesque and private Killington setting, this inviting 4-bedroom, 3.5-bathroom home offers the perfect combination of comfort, functionality, and timeless appeal. Set on a beautiful 5 acre lot with a scenic pond and charming gazebo, the property provides a peaceful backdrop for year-round enjoyment, whether you're sipping your morning coffee by the water or taking in the beauty of Vermont's changing seasons. Thoughtfully renovated and expanded in 1998 in partnership with Roaring Brook Constructors, the home was transformed to better accommodate modern living. Improvements included the addition of baseboard heat, front & rear covered porches, a spacious family room with vaulted ceilings, a large mudroom, designated laundry room, attached two-car garage, and expanded second-floor living space. Complementing the home's generous layout is a formal dining room, ideal for hosting holiday gatherings, dinner parties, or everyday meals with family and friends. The result is a home that offers generous gathering spaces while maintaining a warm and welcoming atmosphere throughout. Filled with natural light, the home features two inviting living rooms, each anchored by a wood-burning fireplace, creating the perfect space to relax and unwind. Significant system upgrades include central air conditioning on the upper level, a standby generator, septic alarm, and well pump safety shut-off for added peace of mind. Recent improvements further enhancing the property's appeal include a new roof installed in 2025, a brand-new boiler installed in 2026, and new carpeting on the second level. Lovingly maintained and enjoyed as a full-time residence, this home offers a rare opportunity to experience the privacy and tranquility Vermont is renowned for while remaining close to all that Killington has to offer. Whether you're seeking a year-round home or a Vermont retreat, this special property is ready to be enjoyed in every season. Call today to schedule your private showing!

4 Beds ⋅ 4 Baths ⋅ 5097221 MLS

Nestled in a picturesque and private Killington setting, this inviting 4-bedroom, 3.5-bathroom home offers the perfect combination of comfort, functionality, and timeless appeal. Set on a beautiful 5 acre lot with a scenic pond and charming gazebo, the property provides a peaceful backdrop for year-round enjoyment, whether you're sipping your morning coffee by the water or taking in the beauty of Vermont's changing seasons. Thoughtfully renovated and expanded in 1998 in partnership with Roaring Brook Constructors, the home was transformed to better accommodate modern living. Improvements included the addition of baseboard heat, front & rear covered porches, a spacious family room with vaulted ceilings, a large mudroom, designated laundry room, attached two-car garage, and expanded second-floor living space. Complementing the home's generous layout is a formal dining room, ideal for hosting holiday gatherings, dinner parties, or everyday meals with family and friends. The result is a home that offers generous gathering spaces while maintaining a warm and welcoming atmosphere throughout. Filled with natural light, the home features two inviting living rooms, each anchored by a wood-burning fireplace, creating the perfect space to relax and unwind. Significant system upgrades include central air conditioning on the upper level, a standby generator, septic alarm, and well pump safety shut-off for added peace of mind. Recent improvements further enhancing the property's appeal include a new roof installed in 2025, a brand-new boiler installed in 2026, and new carpeting on the second level. Lovingly maintained and enjoyed as a full-time residence, this home offers a rare opportunity to experience the privacy and tranquility Vermont is renowned for while remaining close to all that Killington has to offer. Whether you're seeking a year-round home or a Vermont retreat, this special property is ready to be enjoyed in every season. Call today to schedule your private showing!

243 Cricket Hill Rd, Killington

$2,675,000

This Stunning home has an amazing location on the 4th hole of Killington Golf Course in the heart of Killington Resort! It has an extraordinary combination of golf course frontage and unobstructed vistas of the Killington Mountain range. Enjoy total privacy while being less than a half a mile to the downtown restaurants, and less than 2 miles to the Killington Base lodges. The recent renovations by renowned architectural firm Robert Carl Williams include large round custom windows, wide plank white oak quarter sawn flooring, and natural Vermont granite, which are seen throughout this magnificent home. The open floor plan is ideal for entertaining. The chef’s kitchen and large connected dining room are steps from the sunroom with its floor to ceiling windows that integrate the 1.5-acre landscape. This floor also has a main floor guest bedroom and full bathroom. The generous newly added master bedroom on the top floor, with en-suite bathroom, features breathtaking year-round mountain views. This floor also has an additional bedroom and full bathroom. Visit the first floor to discover a family room with a fireplace, kitchenette, two offices, a full bathroom, an additional sunroom, as well as access to the outdoor hot tub. You enter the home via the custom post and beam four vehicle carport. The property has an equally impressive studio apartment located above a heated detached two-car garage. Meticulously designed, constructed, and maintained, this exceptional home will be enjoyed for generations to come.

3 Beds ⋅ 5 Baths ⋅ 5097098 MLS

This Stunning home has an amazing location on the 4th hole of Killington Golf Course in the heart of Killington Resort! It has an extraordinary combination of golf course frontage and unobstructed vistas of the Killington Mountain range. Enjoy total privacy while being less than a half a mile to the downtown restaurants, and less than 2 miles to the Killington Base lodges. The recent renovations by renowned architectural firm Robert Carl Williams include large round custom windows, wide plank white oak quarter sawn flooring, and natural Vermont granite, which are seen throughout this magnificent home. The open floor plan is ideal for entertaining. The chef’s kitchen and large connected dining room are steps from the sunroom with its floor to ceiling windows that integrate the 1.5-acre landscape. This floor also has a main floor guest bedroom and full bathroom. The generous newly added master bedroom on the top floor, with en-suite bathroom, features breathtaking year-round mountain views. This floor also has an additional bedroom and full bathroom. Visit the first floor to discover a family room with a fireplace, kitchenette, two offices, a full bathroom, an additional sunroom, as well as access to the outdoor hot tub. You enter the home via the custom post and beam four vehicle carport. The property has an equally impressive studio apartment located above a heated detached two-car garage. Meticulously designed, constructed, and maintained, this exceptional home will be enjoyed for generations to come.

426 Roaring Brook Rd, Killington

$499,000

Solid 1900 multi-family boasting nearly 4,000 sq. feet of living space. Currently set up as a 4-unit, may be a possibility to convert an office space into a fifth apartment. Clean updated Three 2-bedrooms and an efficiency adding 4 much needed apartments in Rutland City's repertoire. The house features spacious bedrooms with large closets, impressive living areas and tall ceilings. A large attached 2-car garage would be appealing to many future tenants. New sewer line and heat pumps, four 200 amp separate electric boxes and many upgrades including newer floors and metal roof areas. Great rental history!

5097073 MLS

Solid 1900 multi-family boasting nearly 4,000 sq. feet of living space. Currently set up as a 4-unit, may be a possibility to convert an office space into a fifth apartment. Clean updated Three 2-bedrooms and an efficiency adding 4 much needed apartments in Rutland City's repertoire. The house features spacious bedrooms with large closets, impressive living areas and tall ceilings. A large attached 2-car garage would be appealing to many future tenants. New sewer line and heat pumps, four 200 amp separate electric boxes and many upgrades including newer floors and metal roof areas. Great rental history!

36 S Main St, Rutland City

$240,000

Nestled in the picturesque marble town of Proctor, this three-bedroom, two-bath home offers comfort, convenience, and small-town Vermont living at its best. Uniquely situated along the Otter Creek Valley, Proctor is one of Rutland County's most scenic communities, home to the Vermont Marble Museum, Wilson Castle, the Fletcher Proctor Memorial Bridge, Beaver Pond, the Proctor Free Library, Carriage Trails, outdoor skating and roller rink, community pool, and more. Set on a corner lot with a fully fenced yard, this home offers inviting outdoor spaces, including an enclosed front porch perfect for relaxing and a spacious side yard ideal for entertaining, gardening, or pets. Inside, the renovated kitchen features abundant cabinetry, butcher block countertops, newer flooring, and a functional layout. The comfortable living room has wood floors, while an adjoining bonus space makes an excellent home office, reading nook, or play area. A bathroom is conveniently located on each level. The first floor features a half bath just off the rear entry which has a large coat closet, while the second floor offers a newer bath complete with a tiled step-in shower. Upstairs you'll find three bedrooms, each equipped with its own nearly brand-new heat pump, providing efficient heating and air-conditioned comfort. In total, five nearly brand-new heat pumps have been installed throughout the home. Additional updates include some newer windows, electrical improvements, and plumbing upgrades, offering peace of mind while leaving opportunities for cosmetic updates to make the home your own. Outside, a detached vintage garage with an attached potting shed, garden space, and mature shade trees complete the property. Combined with Proctor's highly regarded school system, vibrant community, and rich blend of historical, cultural, and recreational amenities, this home presents a wonderful opportunity to enjoy all that this special Vermont town has to offer.

3 Beds ⋅ 2 Baths ⋅ 5097065 MLS

Nestled in the picturesque marble town of Proctor, this three-bedroom, two-bath home offers comfort, convenience, and small-town Vermont living at its best. Uniquely situated along the Otter Creek Valley, Proctor is one of Rutland County's most scenic communities, home to the Vermont Marble Museum, Wilson Castle, the Fletcher Proctor Memorial Bridge, Beaver Pond, the Proctor Free Library, Carriage Trails, outdoor skating and roller rink, community pool, and more. Set on a corner lot with a fully fenced yard, this home offers inviting outdoor spaces, including an enclosed front porch perfect for relaxing and a spacious side yard ideal for entertaining, gardening, or pets. Inside, the renovated kitchen features abundant cabinetry, butcher block countertops, newer flooring, and a functional layout. The comfortable living room has wood floors, while an adjoining bonus space makes an excellent home office, reading nook, or play area. A bathroom is conveniently located on each level. The first floor features a half bath just off the rear entry which has a large coat closet, while the second floor offers a newer bath complete with a tiled step-in shower. Upstairs you'll find three bedrooms, each equipped with its own nearly brand-new heat pump, providing efficient heating and air-conditioned comfort. In total, five nearly brand-new heat pumps have been installed throughout the home. Additional updates include some newer windows, electrical improvements, and plumbing upgrades, offering peace of mind while leaving opportunities for cosmetic updates to make the home your own. Outside, a detached vintage garage with an attached potting shed, garden space, and mature shade trees complete the property. Combined with Proctor's highly regarded school system, vibrant community, and rich blend of historical, cultural, and recreational amenities, this home presents a wonderful opportunity to enjoy all that this special Vermont town has to offer.

2 Charles St, Proctor

$489,000

Step into timeless Adirondack charm with this beautifully updated turn-of-the-century cottage located in the sought-after Point of Pines Cottage Colony Association. Rich in character and classic lake-style appeal, this inviting home blends historic craftsmanship with thoughtful modern upgrades. Recent improvements include updated electrical throughout, a renovated kitchen and bath, and tasteful decorating enhancements that complement the home’s original warmth and personality. Comfortable and welcoming, the interior offers the perfect setting for relaxing weekends or memorable summer gatherings. Adding to its appeal is a privately owned 25-foot lakefront parcel complete with a 32-foot aluminum dock, ideal for boating, swimming, and enjoying peaceful waterfront living. Whether you're looking for a seasonal retreat or a place to create lasting family traditions, this unique property offers a rare opportunity to enjoy Lake Bomoseen colony living with private lake access.

5 Beds ⋅ 1 Baths ⋅ 5097021 MLS

Step into timeless Adirondack charm with this beautifully updated turn-of-the-century cottage located in the sought-after Point of Pines Cottage Colony Association. Rich in character and classic lake-style appeal, this inviting home blends historic craftsmanship with thoughtful modern upgrades. Recent improvements include updated electrical throughout, a renovated kitchen and bath, and tasteful decorating enhancements that complement the home’s original warmth and personality. Comfortable and welcoming, the interior offers the perfect setting for relaxing weekends or memorable summer gatherings. Adding to its appeal is a privately owned 25-foot lakefront parcel complete with a 32-foot aluminum dock, ideal for boating, swimming, and enjoying peaceful waterfront living. Whether you're looking for a seasonal retreat or a place to create lasting family traditions, this unique property offers a rare opportunity to enjoy Lake Bomoseen colony living with private lake access.

1044 Point Of Pines Rd, Castleton

$745,000

Tucked away at the end of Upper Michigan Road on 54.4 private acres bordering the Green Mountain National Forest, this remarkable 1825 Vermont farmhouse offers breathtaking long-range mountain views in an unforgettable setting. Rich in authentic character, the home showcases rustic knotty pine walls, exposed hand-hewn beams, wide plank floors, and a fieldstone fireplace hearth. The home's low ceilings and gently uneven floors are not imperfections — they are reminders of a time when homes were built by hand and meant to last. A thoughtfully designed addition in 1996 blends seamlessly with the original home, providing modern comfort with a spacious primary bedroom featuring 10-foot ceilings and custom built-ins, a guest bedroom, and a beautifully updated full bath. The expansive living area offers inviting spaces to gather around the woodstove, enjoy movie nights, or relax with family and friends. The vintage-inspired kitchen and dining area, with vaulted ceilings, warm pine finishes, and a picnic-style dining table, is ideal for casual entertaining. Upstairs, two additional guest bedrooms and a powder room provide comfortable accommodations. Outside, more than 30 acres of managed woodland extend along both sides of the town road, complemented by open lawns, mature perennial gardens, and endless opportunities to enjoy the spectacular southern views. A detached two-car garage with overhead storage provides ample space for vehicles and outdoor gear. Snowmobiling, ATV riding, hiking, mountain biking, and snowshoeing are all accessible directly from the property. A state wastewater permit for an additional three-bedroom home offers exceptional flexibility for future expansion or a family compound. This is a rare opportunity to own a legacy Vermont property where history, privacy, recreation, and extraordinary natural beauty come together.

3 Beds ⋅ 2 Baths ⋅ 5097001 MLS

Tucked away at the end of Upper Michigan Road on 54.4 private acres bordering the Green Mountain National Forest, this remarkable 1825 Vermont farmhouse offers breathtaking long-range mountain views in an unforgettable setting. Rich in authentic character, the home showcases rustic knotty pine walls, exposed hand-hewn beams, wide plank floors, and a fieldstone fireplace hearth. The home's low ceilings and gently uneven floors are not imperfections — they are reminders of a time when homes were built by hand and meant to last. A thoughtfully designed addition in 1996 blends seamlessly with the original home, providing modern comfort with a spacious primary bedroom featuring 10-foot ceilings and custom built-ins, a guest bedroom, and a beautifully updated full bath. The expansive living area offers inviting spaces to gather around the woodstove, enjoy movie nights, or relax with family and friends. The vintage-inspired kitchen and dining area, with vaulted ceilings, warm pine finishes, and a picnic-style dining table, is ideal for casual entertaining. Upstairs, two additional guest bedrooms and a powder room provide comfortable accommodations. Outside, more than 30 acres of managed woodland extend along both sides of the town road, complemented by open lawns, mature perennial gardens, and endless opportunities to enjoy the spectacular southern views. A detached two-car garage with overhead storage provides ample space for vehicles and outdoor gear. Snowmobiling, ATV riding, hiking, mountain biking, and snowshoeing are all accessible directly from the property. A state wastewater permit for an additional three-bedroom home offers exceptional flexibility for future expansion or a family compound. This is a rare opportunity to own a legacy Vermont property where history, privacy, recreation, and extraordinary natural beauty come together.

2238 Upper Michigan, Pittsfield

$995,000

A once-in-a-generation opportunity to own one of the most extraordinary and iconic properties on Lake Bomoseen. Tucked away on the private point of Acorn Lodge, behind Rabbit Island, this storybook lakefront retreat occupies one of the most coveted settings on the entire lake. Surrounded by water on multiple sides, the property offers unmatched panoramic views that stretch in every direction, creating the feeling of your own private peninsula. From sunrise reflections to spectacular sunset skies, every corner of this property captures a breathtaking perspective of Lake Bomoseen. Built in 1880, this charming 3-bedroom, 1-bath home is one of the last remaining original lake homes on Lake Bomoseen. A rare piece of the lake's history that can never be replicated. Rich with character and timeless appeal, it offers the chance to own not just a home, but a legacy. The waterfront is simply unrivaled. Featuring spectacular lake frontage, two brand-new oversized docks, direct deep-water access, and a boathouse providing ample storage for all your lake toys and equipment, this property is designed to maximize every aspect of lake living. Equally rare is the expansive, flat, and highly usable land which is a true luxury on waterfront properties and provides endless opportunities for entertaining, recreation, and future enjoyment. Properties of this caliber and uniqueness seldom come to market. The combination of historic charm, unparalleled views, exceptional frontage, direct lake access, and a private point setting creates an offering unlike any other on Lake Bomoseen. Whether enjoyed as a treasured family retreat for generations to come or transformed into your ultimate waterfront escape, this is a truly once-in-a-lifetime chance to own one of the lake's most remarkable properties. Come see for yourself just how special this property is! Give us a call to schedule your own private showing today and enjoy your 2026 summer lakeside.

3 Beds ⋅ 1 Baths ⋅ 5096953 MLS

A once-in-a-generation opportunity to own one of the most extraordinary and iconic properties on Lake Bomoseen. Tucked away on the private point of Acorn Lodge, behind Rabbit Island, this storybook lakefront retreat occupies one of the most coveted settings on the entire lake. Surrounded by water on multiple sides, the property offers unmatched panoramic views that stretch in every direction, creating the feeling of your own private peninsula. From sunrise reflections to spectacular sunset skies, every corner of this property captures a breathtaking perspective of Lake Bomoseen. Built in 1880, this charming 3-bedroom, 1-bath home is one of the last remaining original lake homes on Lake Bomoseen. A rare piece of the lake's history that can never be replicated. Rich with character and timeless appeal, it offers the chance to own not just a home, but a legacy. The waterfront is simply unrivaled. Featuring spectacular lake frontage, two brand-new oversized docks, direct deep-water access, and a boathouse providing ample storage for all your lake toys and equipment, this property is designed to maximize every aspect of lake living. Equally rare is the expansive, flat, and highly usable land which is a true luxury on waterfront properties and provides endless opportunities for entertaining, recreation, and future enjoyment. Properties of this caliber and uniqueness seldom come to market. The combination of historic charm, unparalleled views, exceptional frontage, direct lake access, and a private point setting creates an offering unlike any other on Lake Bomoseen. Whether enjoyed as a treasured family retreat for generations to come or transformed into your ultimate waterfront escape, this is a truly once-in-a-lifetime chance to own one of the lake's most remarkable properties. Come see for yourself just how special this property is! Give us a call to schedule your own private showing today and enjoy your 2026 summer lakeside.

48 Acorn Lodge Rd, Castleton