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$287,500
3 Beds ⋅ 2 Baths ⋅ 5102823 MLS
NEW PRICE! Now offered at $287,500, 29 Ronaldo Court presents a compelling opportunity in an established Rutland City neighborhood. A recently updated neighboring home on the same street closed at $335,000, creating a meaningful $47,500 difference for buyers who would rather personalize a home to their own taste than pay a premium for someone else’s style. This three-bedroom, 1.5-bath raised ranch offers approximately 1,830 square feet of finished living space with a practical layout and a partially finished lower level that adds flexibility for a family room, home office, recreation area, den, or guest space. Just off the kitchen, a rear deck provides an inviting place for outdoor dining, entertaining, or relaxing while overlooking the backyard. Enjoy the sights and sounds of nearby Moon Brook, creating a peaceful natural backdrop that is not often found within the city. Despite the brookside setting, the home is not located within a designated flood zone, offering buyers the enjoyment of the natural setting without the property itself being mapped in a flood hazard area. Additional features include a one-car garage, paved driveway, and convenient access to Rutland High School, Rutland Regional Medical Center, shopping, dining, and other city amenities. For buyers looking for space, location, and the opportunity to make a home truly their own, 29 Ronaldo Court deserves a look. This home offers a wonderful combination of neighborhood living, flexible interior space, and an outdoor setting placing this one on your short list! Welcome Home! OPEN HOUSE SUNDAY SEPTEMBER 13TH - NOON to 2:00PM

29 Ronaldo Ct, Rutland City
$354,500
4 Beds ⋅ 3 Baths ⋅ 5102595 MLS
Welcome home to this classic Colonial offering over 2,200 square feet of living space in a convenient Rutland City location. With four bedrooms and 2.5 bathrooms, this home blends timeless character with everyday functionality and offers an excellent opportunity to make it your own.The spacious floor plan features generous living areas, making it easy to entertain guests or enjoy quiet evenings at home. Upstairs, you'll find four well-proportioned bedrooms, providing plenty of space for family, guests, or a home office.Situated on a manageable 0.23-acre lot with a paved driveway and public road frontage, this property offers easy maintenance while still providing outdoor space for gardening, recreation, or relaxing. Conveniently located near shopping, restaurants, schools, parks, and downtown Rutland amenities, this home is full of potential and ready for its next owner to add their personal touch.

72 Edgerton St, Rutland City
$259,000
3 Beds ⋅ 2 Baths ⋅ 5102069 MLS
Open House 8/1 11am-1pm! This charming single-family home in Rutland City is bound to sell quickly! Imagine yourself relaxing, sipping coffee, and watching the sun rise from your large, private deck, the perfect place to start your day or unwind in the evening. Inside, you'll find warm wood finishes throughout that add character and charm, while the spacious layout offers flexibility to fit a variety of lifestyles. Step inside to a welcoming dining area that flows seamlessly into the large kitchen, offering space for either bar-style seating or a full dining table, making it ideal for everyday meals or gathering with family and friends. The first floor also includes a private office or bonus room, providing additional space for working from home, hobbies, or other needs. Continue past the kitchen and dining area into the expansive, sun-filled living room, where natural light creates a bright and inviting atmosphere. Just off the living room is a generously sized first-floor bathroom with the convenience of laundry. Upstairs, you'll find two charming bedrooms, each featuring large dormer windows that bring in plenty of natural light, closet space, and built-in beds that add to the home's unique character. A spacious second bathroom completes the upper level, offering added convenience and functionality. With its versatile floor plan, inviting living spaces, and distinctive charm, this home is ready for its next owner to make it their own.

150 Holly St, Rutland City
$525,000
3 Beds ⋅ 3 Baths ⋅ 5101623 MLS
Spacious, bright and well-maintained 3-bedroom, 3-bath home featuring an open-concept kitchen, dining and living area with cathedral ceilings. Enjoy a pantry, laundry room, hardwood floors, attached 2-car garage, a bright finished lower level that offers exceptional flexibility with a separate private exterior entrance in addition to interior access from the main level, two extra rooms with large windows, closets, and two bathrooms. Ideal for office or sleeping, gym, yoga, media space, an in-law suite, young adult children looking for their own space and independence, live in help, or potential rental unit. Relax in the quiet backyard, perfect for entertaining or unwinding. Conveniently located just minutes from shopping, local businesses, restaurants, Home Depot, Rutland Regional Medical Center, Rutland High School and downtown Rutland. Outdoor enthusiasts will appreciate being just 8 miles from Pico Mountain and 13 miles from Killington Resort. Enjoy the convenience of being close to everything while coming home to a quiet peaceful neighborhood. Additional interior photos to follow.

8 Lamontagne Ln, Rutland City
$319,900
5101525 MLS
Investment Opportunity in the Heart of Rutland City! Discover the perfect blend of classic charm and income producing potential with this beautiful three unit Gambrel style multifamily home on Church Street in Rutland City. Featuring gorgeous hardwood floors, thoughtful updates, and timeless character throughout, this well-maintained property is ready to welcome its next owner. Whether you’re looking to owner occupy and let rental income help offset your mortgage and living expenses or add a solid investment property to your portfolio, this versatile property offers endless possibilities. It's convenient location places you close to shopping, restaurants, schools, parks, and many of Rutland City’s everyday amenities. If you’ve been searching for a multifamily property that combines charm, convenience, and excellent income potential, this is the opportunity you’ve been waiting for. Schedule your showing today and see all that this exceptional Church Street property has to offer!

65 Church St, Rutland City
$225,000
5101519 MLS
Attention visionaries and portfolio builders: here's a two unit multifamily with two bedrooms in each unit, located on 2,474 square feet of raw potential and a convenient location. This building is a canvas waiting for a confident brush. The bones are solid, the footprint is generous, and the opportunity to add real value is genuine whether you're refreshing tired finishes, reconfiguring layouts, or transforming the space into rental income. Savvy investors will recognize immediately what a property like this can become with a thoughtful renovation plan and a little imagination. First-time buyers or skiers eyeing house-hacking, meanwhile, can occupy one unit while tenants help cover the mortgage. The layout offers flexibility, giving you room to shape the configuration that suits your goals. Downtown sits within easy walking distance, meaning coffee shops, restaurants, and errands are all reachable on foot, a perk that keeps quality tenants interested and leases signed. The Marble Valley Regional Transit are just minutes away, making car-free living a legitimate option. Adventure seekers, take heart: the legendary slopes of Killington sit a scenic drive east, promising world-class skiing and four seasons of mountain recreation practically in your backyard.

31 Baxter St, Rutland City
$199,500
3 Beds ⋅ 2 Baths ⋅ 5100936 MLS
Move right into this remodeled 3-bedroom, 2 full-bath home located in Rutland City. The first floor offers the ease of one-level living with a spacious, updated kitchen that includes a washer and dryer, a comfortable first-floor bedroom, and a full bathroom. The functional layout is perfect for everyday living and added convenience. Upstairs, you'll find two generously sized bedrooms and a second full bathroom, providing plenty of space for family, guests, or a home office. This updated home combines modern improvements with a practical floor plan, making it an excellent option for first-time buyers, downsizers, or anyone looking for a move-in-ready property.

3 Meadow St, Rutland City
$248,000
5100840 MLS
Six bedrooms. Two bathrooms. One seriously flexible floor plan. This roomy Rutland home currently lives happily as a single-family residence, but its multi-family past means the bones are already there to convert it back into a two-unit income machine whenever the mood strikes. That kind of dual personality is rare, and it puts you firmly in the driver's seat. Spread out and enjoy every generous room as one big household, or reimagine the layout to collect rent while you're at it. Either way, the attractive price point makes the numbers refreshingly friendly, whether you're a growing family craving elbow room or an investor hunting for reliable cash flow. The location does plenty of heavy lifting too. Rutland's historic downtown sits just a short stroll away, where local shops, cafes, and timeless New England character keep the neighborhood buzzing. Depot Park offers a green spot to unwind, while the nearby train station and regional bus service make getting around wonderfully simple—a real bonus for tenants who value connection. Outdoor lovers won't feel shortchanged either. Pine Hill Park delivers miles of wooded trails practically around the corner, and when snow starts falling, Pico Mountain and legendary Killington Resort are both a quick drive east for world-class skiing. Comfortable home base, savvy rental play, or a little of both—this generous property leaves the choice entirely up to you. Come see the potential in person and start imagining the possibilities today. Alsolisted as Single Family MLS #5100839

36 Summer St, Rutland City
$248,000
6 Beds ⋅ 2 Baths ⋅ 5100839 MLS
Six bedrooms. Two bathrooms. One seriously flexible floor plan. This roomy Rutland home currently lives happily as a single-family residence, but its multi-family past means the bones are already there to convert it back into a two-unit income machine whenever the mood strikes. That kind of dual personality is rare, and it puts you firmly in the driver's seat. Spread out and enjoy every generous room as one big household, or reimagine the layout to collect rent while you're at it. Either way, the attractive price point makes the numbers refreshingly friendly, whether you're a growing family craving elbow room or an investor hunting for reliable cash flow. The location does plenty of heavy lifting too. Rutland's historic downtown sits just a short stroll away, where local shops, cafes, and timeless New England character keep the neighborhood buzzing. Depot Park offers a green spot to unwind, while the nearby train station and regional bus service make getting around wonderfully simple—a real bonus for tenants who value connection. Outdoor lovers won't feel shortchanged either. Pine Hill Park delivers miles of wooded trails practically around the corner, and when snow starts falling, Pico Mountain and legendary Killington Resort are both a quick drive east for world-class skiing. Comfortable home base, savvy rental play, or a little of both—this generous property leaves the choice entirely up to you. Come see the potential in person and start imagining the possibilities today. Also listed as Multi-Family MLS 5100840

36 Summer St, Rutland City
$310,000
3 Beds ⋅ 1 Baths ⋅ 5100754 MLS
Welcome home to this well-maintained 3-bedroom, 1-bath ranch located in one of Rutland City's most sought-after neighborhoods. Set on a level 0.34-acre lot, this bright and airy home offers comfortable one-level living with the added bonus of a partially finished lower level that provides plenty of extra space to fit your lifestyle. The main level features an inviting layout with abundant natural light, three bedrooms, and a full bathroom, creating a warm and welcoming atmosphere throughout. Downstairs, you'll find a spacious finished family room that's perfect for a media room, playroom, home office, or gym, along with a dedicated laundry area and generous storage space. Step outside onto the large back deck, an ideal spot for grilling, entertaining, or simply relaxing while overlooking the spacious backyard. An attached one-car garage adds everyday convenience, while the desirable neighborhood offers a peaceful setting that's just minutes from shopping, restaurants, schools, parks, and all that Rutland has to offer. Whether you're searching for your first home, looking to downsize, or simply want a move-in ready property in a fantastic location, this charming ranch is one you won't want to miss.

15 Stone Ridge Dr, Rutland City
$460,000
4 Beds ⋅ 2 Baths ⋅ 5100483 MLS
Welcome to a truly remarkable residence - a timeless old-style home where exceptional craftsmanship, historic elegance, & thoughtful updates harmonize. From the moment you step inside, you'll be greeted by breathtaking original woodwork, rich oak floors, stunning fireplaces, & impressive architectural details. Every room tells a story of enduring quality while offering the comfort & functionality today's buyers desire. The beautifully remodeled kitchen is the heart of the home, masterfully updated to preserve its historic character while embracing modern convenience. Light-filled, airy, & impeccably designed, it is truly a flawless space. A grand foyer leads to an expansive formal dining room, perfect for hosting family gatherings & memorable celebrations. The 1st floor also features a spacious living room along with a versatile bonus finished space. The 2nd floor continues to impress with 4 generously sized bedrooms, an open central hallway, full bathroom, custom built-ins, & exquisite craftsmanship. Every detail exudes elegance & rare authenticity. The 3rd floor attic presents even more opportunity, whether envisioned as additional living space or storage. Offering nearly 3,500 finished sq. ft. above grade, this monumental floor plan provides room to live, entertain, & grow without sacrificing character. Architecturally, the home is a striking blend of late 19th-century Victorian influence & romantic Italian countryside design, with a hipped roof, stucco exterior, grand covered entry, & an abundance of oversized windows. Completing the property is a partially above-grade basement, detached 2-car garage, charming balcony & a desirable corner lot. More than just a house, this is an estate; a rare chance to own an architectural treasure where history, beauty, & craftsmanship have been lovingly preserved while offering the space & amenities for modern living. Homes of this caliber are seldom available, making this a truly unforgettable Rutland City offering.

32 North St, Rutland City
$345,000
5100442 MLS
Welcome home to this well-maintained property offering space, flexibility, and endless possibilities! The main level offers three comfortable bedrooms, a full bathroom and a beautiful updated kitchen with a convenient walk in pantry. A first-floor washer and dryer add everyday convenience and functionality to the home's thoughtful layout. The spacious living room and large dining area ideal for gathering with family and friends. Upstairs, you'll find three additional bedrooms, offering exceptional flexibility for a growing household, welcoming guests, creating a home office, or designing the perfect hobby or recreation space. Enjoy peace of mind with a new roof installed aprx. 3 years ago and most major mechanical systems less than seven years old. The home is also pre-wired for a whole house generator, making future installation simple and convenient. Step outside to the rear deck and unwind while overlooking the private backyard, naturally screened by mature foliage for a secluded setting. Adding to its appeal, this property was once configured as a two-unit home and offers the potential to be converted back, making it an excellent opportunity for multi-generational living or investment potential. Whether you're looking for a spacious single-family home or a property with income-producing possibilities, this versatile home is ready to meet your needs.

49 North St, Rutland City
$345,000
5 Beds ⋅ 2 Baths ⋅ 5100438 MLS
Welcome home to this well-maintained property offering space, flexibility, and endless possibilities! The main level offers three comfortable bedrooms, a full bathroom and a beautiful updated kitchen with a walk-in pantry. A first-floor washer and dryer add everyday convenience and functionality to the home's thoughtful layout. The spacious living room and large dining area ideal for gathering with family and friends. Upstairs, you'll find three additional bedrooms, offering exceptional flexibility for a growing household, welcoming guests, creating a home office, or designing the perfect hobby or recreation space. Enjoy peace of mind with a new shingle roof installed aprx. 3 years ago and most major mechanical systems less than seven years old. The home is also pre-wired for a whole house generator, making future installation simple and convenient. Step outside to the rear deck and unwind while overlooking the private backyard, naturally screened by mature foliage for a secluded feeling atmosphere. Adding to its appeal, this property was once configured as a two-unit home and offers the potential to be converted back, making it an excellent opportunity for multi-generational living or investment potential. Whether you're looking for a spacious single-family home or a property with income-producing possibilities, this versatile home is ready to meet your needs.

49 North St, Rutland City
$250,000
3 Beds ⋅ 2 Baths ⋅ 5100286 MLS
Historic Charm. Modern Upgrades. Easy Living. This beautifully maintained 3-bedroom, 1.5-bath home perfectly balances classic detail with smart, modern updates. It starts with the welcoming wraparound front porch, which is a spacious, inviting spot for enjoying morning coffee, evening cocktails with friends, or simply curling up with a good book. Upon entering, you’ll find the inside of this home as appealing as the outside, highlighted by original woodwork and hardwood floors. The living and dining rooms flow openly into one another, making the main level perfect for everything from easy, everyday living to hosting holiday gatherings. At the center of the home is the kitchen, featuring stainless steel appliances, plenty of storage, and a handy mudroom that leads out to the side porch and the backyard. A flexible first-floor bedroom (currently used as a den) sits near the half bath, making it the perfect setup for guests, first-floor living, or a home office. Upstairs, an open bonus room offers extra hangout space, alongside a full bath and two comfortable bedrooms, one of which has a classic transom window and a private balcony. Behind this home’s vintage charm are impressive energy-efficient infrastructure upgrades, including a new boiler, a heat pump water heater, and a mini-split for efficient heating and cooling. There is also an exterior EV charger and a state-of-the-art smart SPAN® electrical panel that lets you manage the whole home’s energy right from your phone. Located in the heart of Rutland, this lovely home is just moments from downtown restaurants, shopping, parks, RRMC, and a plethora of recreational opportunities, including Pine Hill Park for mountain biking and Killington-Pico Ski Resort.

99 Franklin St, Rutland City
$499,000
4 Beds ⋅ 3 Baths ⋅ 5100088 MLS
Welcome to this beautifully maintained 4-bedroom, 3-bathroom home nestled in a great Rutland City neighborhood. Offering a flexible floor plan, generous living spaces, and an exceptional backyard oasis, this home is ready for its next owners. The first floor features an updated kitchen, a formal dining room, and a spacious living room that's perfect for everyday living and entertaining. Also on the main level are two bedrooms and two full bathrooms, creating an ideal setup for a first-floor primary suite or a separate wing for children, guests, or multi-generational living. Upstairs, you'll find two additional bedrooms, including a spacious bedroom with an adjoining sitting area that would make an excellent home office, reading nook, or private retreat. A ¾ bathroom completes the second level. Outside, enjoy your private backyard with beautiful perennial gardens, a spacious deck, an in-ground swimming pool, and a storage shed. This move-in-ready home offers the perfect combination of comfort, flexibility, and outdoor enjoyment. Don't miss the opportunity to make it yours!

10 Catherine Dr, Rutland City
$90,000
5100032 MLS
Discover the potential of this unique City lot in an established Rutland neighborhood. The property features a large, older storage building believed to have originally served as a carriage building, offering character and a variety of possibilities for its next owner. Whether you're looking to build a new home, create a workshop, or utilize the existing building for vehicle, equipment, or material storage, this property offers flexibility in a convenient location with a curb cut on East Street too. Neighborhood Business zoning may allow a variety of residential and commercial uses, making it an appealing opportunity for homeowners, entrepreneurs, investors, contractors, landscapers, tradespeople, collectors, or hobbyists seeking space for their business or personal interests. Conveniently located just minutes from downtown Rutland, you'll enjoy easy access to shopping, restaurants, schools, healthcare, and everyday amenities. Vermont's outdoor recreation is also close at hand, including skiing at Killington Resort and Pico Mountain, hiking and biking throughout the region, boating and fishing on nearby lakes including Lake Bomoseen and Lake St Catherine, and countless opportunities to enjoy the Green Mountains. Convenient travel is available via Rutland–Southern Vermont Regional Airport, with Burlington International Airport and Albany International Airport both within an easy drive. Buyer is responsible for conducting their own due diligence with the City of Rutland to verify zoning regulations, permitted uses, building requirements, utility availability, and any approvals necessary for their intended use.

40 Terrill St, Rutland City
$89,000
5099313 MLS
Beautiful city lot waiting for your home to be built on it.

29.5 Hillside Rd, Rutland City
$299,000
5099297 MLS
Investment Opportunity in Rutland, VT! Welcome to 33 Summer Street, a four-unit multifamily property in a prime Rutland location. This property features three renovated units with modern amenities and updated finishes. The exterior has been freshly painted, the old unused chimney has been removed, and a clean Certificate of Occupancy is in hand, offering added peace of mind for the next owner. Conveniently located close to local amenities and public transportation, this property is well positioned to attract tenants. Whether you're looking to expand your portfolio or start investing in real estate, 33 Summer Street presents an excellent opportunity with strong potential for steady rental income.

33 Summer St, Rutland City
$309,000
3 Beds ⋅ 3 Baths ⋅ 5099281 MLS
Welcome to this charming 3-bedroom, 2.5-bath Colonial located on a quiet dead-end street in Rutland City. Situated on a spacious 0.36-acre lot, this home offers plenty of room both inside and out, along with a detached 2-car garage and an additional one-bay garage beneath the house for extra parking, storage, or a workshop. Inside, you'll find beautiful hardwood floors throughout the home. The main level features a spacious kitchen with a large pantry, a convenient half bath, a comfortable living room with a cozy pellet stove, a den or playroom, and an additional versatile room that's perfect as a home office or potential first-floor bedroom. Upstairs, you'll find three bedrooms and a full bathroom. The finished basement adds valuable living space with a bonus room, laundry area, and a three-quarter bath, making it ideal for guests, recreation, or a home gym. Outside, enjoy the patio and backyard with plenty of room for children and pets to play, as well as space for gardening or entertaining. Located in a peaceful neighborhood with minimal traffic, this property offers a wonderful combination of comfort, flexibility, and outdoor enjoyment.

39 Cramton Ave, Rutland City
$67,000
2 Beds ⋅ 2 Baths ⋅ 5099276 MLS
Affordable, move-in ready, and being sold fully furnished this well maintained 2 bedroom, 1.5 bath single-wide home is a fantastic opportunity in Rutland City! Step inside to find a spacious living room, two generously sized bedrooms, and a large eat-in kitchen with plenty of room for dining and gathering. Just off the dining area, a rear deck offers the perfect spot to enjoy your morning coffee or unwind after a long day. Additional conveniences include a handicap-accessible ramp, in home washer and dryer, and a functional layout designed for easy everyday living. Ideally located just minutes from Rutland Regional Medical Center, shopping, restaurants, and all the amenities Rutland City has to offer. Sale is contingent upon park approval. Park requirements include a minimum credit score of 680 or higher, and no dogs are permitted in the park.

9 Billings Mobile Mnr, Rutland City
$289,000
3 Beds ⋅ 1 Baths ⋅ 5098847 MLS
Three bedroom ranch on a spacious city lot in the outskirts of Rutland City with impeccable mountain views. Close to restaurants and parks, but central to skiing and lake regions. The house has been well maintained and is ready for its new owners to make it their own.

140 Dorr Dr, Rutland City
$339,000
3 Beds ⋅ 2 Baths ⋅ 5098926 MLS
Just Reduced. Take advantage of this great price. Gorgeous & private back yard paradise with beautiful in-ground pool, surrounded by expansive stamped-concrete & relaxing shaded patio. Propane firepit for enjoying your surroundings late into the evening. This three bedroom, one and half bath raised ranch is very spacious with luminous living room, eat in kitchen, its lower level family room and/or office, with direct access to the delightful backyard. Sliders off the kitchen lead to a very large deck covered by a magnificent gazebo to enjoy your back yard views in every kind of weather. Seller owned solar panels, replacement windows, heat pump & pellet stove make this home extremely efficient and affordable. Outbuildings allow for great storage space for all your patio furniture & pool equipment. Do not delay on this special offering. You'll never want to leave home.

168 Lincoln Ave, Rutland City
$339,000
3 Beds ⋅ 2 Baths ⋅ 5098432 MLS
OPEN HOUSE JULY 11TH-9:00 to Noon. CHARTER HILLS. Desirable location, beautiful updates, and a wonderful neighborhood setting make this 3-bedroom, 2-bath home a standout. Charter Hills is known for its peaceful atmosphere, community pond, and excellent walkability, and is conveniently located near schools, Rutland Regional Medical Center, shopping, dining, and a short drive to world-class skiing at Killington Resort. The current owners have thoughtfully modernized the home, opening a wall to create a bright, inviting floor plan that's perfect for today's lifestyle. The renovated kitchen is the heart of the home, featuring all-new appliances, gleaming granite countertops, ample cabinetry, and a spacious breakfast bar for casual meals and busy mornings. The adjoining living area is filled with natural light and enhanced by a new sliding glass door leading to an oversized, newer deck with low-maintenance Trex decking. Step outside and enjoy the private backyard, an ideal setting for entertaining, gardening, or simply relaxing. The main level offers three comfortable bedrooms, a full bath, and attractive new vinyl flooring throughout, creating a fresh, clean, move-in-ready feel. The sunny lower level offers valuable living space, including a generously sized family room, a second full bath, and a convenient laundry area. Multiple windows allow natural light to pour in, making this level feel warm and welcoming rather than basement-like. Additional improvements include updates to the roof and major mechanical systems, providing peace of mind for the next owner. The paved driveway and .30-acre lot enhance the home's appeal, offering low maintenance while still providing plenty of outdoor enjoyment. Whether you're looking for a wonderful family home, a comfortable place to downsize, or simply a property in one of the area's most sought-after neighborhoods, this Charter Hills residence offers the perfect blend of privacy, convenience, and modern updates.

6 Irving Hts, Rutland City
$259,000
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
$300,000
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
$259,000
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
$249,000
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
$499,000
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
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
$499,000
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

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