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Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame home. Outside, perennial gardens give way to open pasture suitable for a few horses or sheep, woodland trails for riding, hiking, cross-country skiing, and snowshoeing and direct access to the GMHA trail system. Built in 2015, the three-bedroom residence is defined by soaring spaces, exposed fir beams, walls of glass, and craftsmanship that feels substantial without being formal. Nearly every principal room is oriented toward the eastern views, bringing the surrounding mountains and changing Vermont landscape into daily life. The main level is equally comfortable for quiet everyday living or a houseful of guests, with an open kitchen, dining area, and dramatic great room centered around a floor-to-ceiling double-sided stone fireplace. A more intimate sitting room, screened porch, expansive deck, and primary suite are also located on this floor. Upstairs are a loft office, two en suite guest bedrooms, and a media room. The walk-out lower level adds a gym, infrared sauna, workshop, and temperature-controlled wine room with capacity for approximately 1,000 bottles. An 18.5 kW solar array supports near net-zero living, while a three-bay garage accommodates vehicles, sporting equipment, and the gear that comes with an active Vermont life. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort.

3 Beds ⋅ 4 Baths ⋅ 5099532 MLS

Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame home. Outside, perennial gardens give way to open pasture suitable for a few horses or sheep, woodland trails for riding, hiking, cross-country skiing, and snowshoeing and direct access to the GMHA trail system. Built in 2015, the three-bedroom residence is defined by soaring spaces, exposed fir beams, walls of glass, and craftsmanship that feels substantial without being formal. Nearly every principal room is oriented toward the eastern views, bringing the surrounding mountains and changing Vermont landscape into daily life. The main level is equally comfortable for quiet everyday living or a houseful of guests, with an open kitchen, dining area, and dramatic great room centered around a floor-to-ceiling double-sided stone fireplace. A more intimate sitting room, screened porch, expansive deck, and primary suite are also located on this floor. Upstairs are a loft office, two en suite guest bedrooms, and a media room. The walk-out lower level adds a gym, infrared sauna, workshop, and temperature-controlled wine room with capacity for approximately 1,000 bottles. An 18.5 kW solar array supports near net-zero living, while a three-bay garage accommodates vehicles, sporting equipment, and the gear that comes with an active Vermont life. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort.

115 Eastman Rd, Woodstock

$2,950,000

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful perennial gardens, antique moss covered stonewalls, an apple orchard, large swimming pond and a privately sited tennis court. The Estate is meticulously cared for and combines antique craftsmanship with modern touches. The Main house consists of 5 bedrooms including a first floor primary suite with private bath, vaulted ceilings and new large walk in closet. Kitchen features thermador appliances and quartz counters anchored by a large dining room with stunning wood floors. An expansive cozy living room centered by a handsome brick fireplace to curl up with a book on a snowy day. The rooms are spacious and inviting with an abundance of light, exposed original hand-hewn beams and easy access for outdoor entertaining on the brick patio or the new east terrace. Enjoy a separate 3 bedroom Guest House for friends/family with good rental income history. New Tesla Tower for backup power. Located in the heart of horse country and the village of South Woodstock. Enjoy skiing, championship golf and fly fishing on the Black River. Easy access to shopping, restaurants and Upper Valley. Only 8 minutes to Woodstock, 2.5 hours to Boston and 5 hours to NYC. Kedron Valley Farm is a stunning, quintessential farm in the heart of GMHA.

8 Beds ⋅ 8 Baths ⋅ 5094600 MLS

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful perennial gardens, antique moss covered stonewalls, an apple orchard, large swimming pond and a privately sited tennis court. The Estate is meticulously cared for and combines antique craftsmanship with modern touches. The Main house consists of 5 bedrooms including a first floor primary suite with private bath, vaulted ceilings and new large walk in closet. Kitchen features thermador appliances and quartz counters anchored by a large dining room with stunning wood floors. An expansive cozy living room centered by a handsome brick fireplace to curl up with a book on a snowy day. The rooms are spacious and inviting with an abundance of light, exposed original hand-hewn beams and easy access for outdoor entertaining on the brick patio or the new east terrace. Enjoy a separate 3 bedroom Guest House for friends/family with good rental income history. New Tesla Tower for backup power. Located in the heart of horse country and the village of South Woodstock. Enjoy skiing, championship golf and fly fishing on the Black River. Easy access to shopping, restaurants and Upper Valley. Only 8 minutes to Woodstock, 2.5 hours to Boston and 5 hours to NYC. Kedron Valley Farm is a stunning, quintessential farm in the heart of GMHA.

5798 South Rd, Woodstock

$2,950,000

Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary residence is perfectly sited to overlook Woodstock’s iconic Mount Tom and the Marsh-Billings Museum, Vermont’s only National Park. The property sits at the end of a quiet road with only one other neighboring residence. There is a bedroom suite on each of the three levels, allowing family members or guests to claim their own space. The open living room on the main level is a natural gathering place, either by the fire in the winter, or out on the deck in the summertime to take in the views. The adjoining 1,040-sqft modern pool house was completed in 2023, providing a luxurious new extension of the home. Inside is an open floor plan, where floor-to-ceiling windows showcase unobstructed mountain views to the North and West. Thoughtfully designed with a custom Viking kitchen, spa-style walk-in shower, and guest bed, the pool house is ideal for entertaining guests, hosting family parties, or relaxing apres-ski. The outdoor heated pool is a centerpiece of the property, providing four-season enjoyment.

3 Beds ⋅ 5 Baths ⋅ 5072035 MLS

Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary residence is perfectly sited to overlook Woodstock’s iconic Mount Tom and the Marsh-Billings Museum, Vermont’s only National Park. The property sits at the end of a quiet road with only one other neighboring residence. There is a bedroom suite on each of the three levels, allowing family members or guests to claim their own space. The open living room on the main level is a natural gathering place, either by the fire in the winter, or out on the deck in the summertime to take in the views. The adjoining 1,040-sqft modern pool house was completed in 2023, providing a luxurious new extension of the home. Inside is an open floor plan, where floor-to-ceiling windows showcase unobstructed mountain views to the North and West. Thoughtfully designed with a custom Viking kitchen, spa-style walk-in shower, and guest bed, the pool house is ideal for entertaining guests, hosting family parties, or relaxing apres-ski. The outdoor heated pool is a centerpiece of the property, providing four-season enjoyment.

249 Sawyer Rd, Woodstock

$2,600,000

2687 GARVIN HILL ROAD- Surrounded by the rolling hills and natural beauty of the Woodstock countryside, 2687 Garvin Hill Road offers a quintessential Vermont lifestyle on 18.16 acres, just minutes from the heart of Woodstock Village. Landscaped grounds, old stone walls, and expansive acreage create an inviting setting for gardening, outdoor gatherings, walking the property, or simply enjoying the changing seasons. The 5-bedroom historic residence blends original charm and character with sophisticated upgrades, creating warm, comfortable living spaces without compromising modern convenience. A bright, light-filled kitchen and dining area flows beautifully into a formal dining room and a dramatic vaulted great room–showcasing exposed hand-hewn beams and a wood-burning fireplace–as well as a sizable screened porch overlooking the grounds, all of which provide an ideal setting for entertaining family and friends. Adjacent to the kitchen on the other side of the house is a more intimate living room with a second fireplace, an office, and a bedroom with full bath, offering the possibility of one-level living. Upstairs, there is an en suite bedroom and two additional bedrooms that share a full bath. The lower level adds versatile finished space with a 5th bedroom guest suite with recreation space. An attached three-bay garage and barn provide ample room for vehicles, outdoor equipment, and all the gear that comes with four-season Vermont living. The attached barn has two horse stalls. There are two beautiful ponds on the property, the larger is well positioned in the backyard towards the view. Beyond the property, Woodstock’s extensive network of hiking and biking trails, nearby rivers, golf, skiing, and other year-round recreation along with shops, restaurants, and galleries are all within easy reach. Some photos are digitally enhanced.

5 Beds ⋅ 5 Baths ⋅ 5112419 MLS

2687 GARVIN HILL ROAD- Surrounded by the rolling hills and natural beauty of the Woodstock countryside, 2687 Garvin Hill Road offers a quintessential Vermont lifestyle on 18.16 acres, just minutes from the heart of Woodstock Village. Landscaped grounds, old stone walls, and expansive acreage create an inviting setting for gardening, outdoor gatherings, walking the property, or simply enjoying the changing seasons. The 5-bedroom historic residence blends original charm and character with sophisticated upgrades, creating warm, comfortable living spaces without compromising modern convenience. A bright, light-filled kitchen and dining area flows beautifully into a formal dining room and a dramatic vaulted great room–showcasing exposed hand-hewn beams and a wood-burning fireplace–as well as a sizable screened porch overlooking the grounds, all of which provide an ideal setting for entertaining family and friends. Adjacent to the kitchen on the other side of the house is a more intimate living room with a second fireplace, an office, and a bedroom with full bath, offering the possibility of one-level living. Upstairs, there is an en suite bedroom and two additional bedrooms that share a full bath. The lower level adds versatile finished space with a 5th bedroom guest suite with recreation space. An attached three-bay garage and barn provide ample room for vehicles, outdoor equipment, and all the gear that comes with four-season Vermont living. The attached barn has two horse stalls. There are two beautiful ponds on the property, the larger is well positioned in the backyard towards the view. Beyond the property, Woodstock’s extensive network of hiking and biking trails, nearby rivers, golf, skiing, and other year-round recreation along with shops, restaurants, and galleries are all within easy reach. Some photos are digitally enhanced.

2687 Garvin Hill Rd, Woodstock

$2,599,000

This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with maple-lined streets, stately homes, artisanal boutiques, and a warm and welcoming spirit. The town and assorted local organizations offer cultural and family fun activities offered throughout the year. Currently being used as a 7-room Inn boasting an additional 2-bedroom owner’s quarters, this property could be returned to operating as a private residential property with zoning permit. Please contact for more information on making this beautiful place your dream home!

9 Beds ⋅ 11 Baths ⋅ 5062350 MLS

This exquisite Victorian invites you to embracequintessential New England living in a charming downtown setting. This property in Woodstock, VT offers a rare blend of historic charm and modern convenience, all within one of Vermont’s most beloved communities. Woodstock is often hailed as “the prettiest small town in America,” and for good reason. The village is a vibrant resort town with maple-lined streets, stately homes, artisanal boutiques, and a warm and welcoming spirit. The town and assorted local organizations offer cultural and family fun activities offered throughout the year. Currently being used as a 7-room Inn boasting an additional 2-bedroom owner’s quarters, this property could be returned to operating as a private residential property with zoning permit. Please contact for more information on making this beautiful place your dream home!

41 Pleasant St, Woodstock

$2,500,000

See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butler’s pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficiencies—including a whole-house generator and rooftop solar—offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermont’s finest amenities. Some photos are digitally enhanced.

4 Beds ⋅ 4 Baths ⋅ 5087228 MLS

See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero refrigerator, Wolf range, dual dishwashers, prep sink, and a generous granite island perfect for gathering. Beyond the kitchen, a gracious butler’s pantry, inviting den, game room, and large living room create a home that is as functional as it is inviting. Expansive windows frame unobstructed views, bringing the surrounding landscape into every room, while modern efficiencies—including a whole-house generator and rooftop solar—offer peace of mind and sustainability. Equestrians and hobby enthusiasts alike will appreciate the impeccably maintained grounds: a four-stall barn with heated tack room, double run-in shed within the six-acre pasture, a greenhouse, and an additional five-bay garage/shop provide endless flexibility for pursuits and storage. The primary three-car garage ensures convenience close to home. With two wells servicing the property and an included separate, buildable lot with a four-bedroom septic design, the estate presents a unique opportunity for expansion or multigenerational living. All of this, just seven minutes from the charm of Woodstock Village and under twenty minutes to world-class skiing, creates a lifestyle defined by privacy, beauty, and effortless access to Vermont’s finest amenities. Some photos are digitally enhanced.

114 Oak Ridge Way, Woodstock

$2,300,000

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the french doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom book shelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garage and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view!

5 Beds ⋅ 6 Baths ⋅ 5098424 MLS

Exceptional Views to Killington! Perched high on a private knoll and surrounded by open lush meadows and surrounded by antique stonewalls. This 5 bedroom, 4 bathroom extended cape styled home was renovated approx 15 years ago with handsome hardwood floors throughout. Large kitchen with Calcutta Marble, Electrolux stainless appliances and ample storage that opens into the dining room- The formal living room also has expansive views beyond the french doors to a covered porch across the back of the house for entertaining family and friends. The living room is anchored by a traditional propane fireplace, custom book shelves, lovely pocket doors... it's easy to want to curl up with a good book in the wintertime. Generous primary suite with custom built-ins, walk in closet and expansive bathroom located on first floor. There is a second guest bedroom with full bath on the first floor as well as a cozy den surrounded by built-in bookcases. Second floor features 3 very large bedrooms and 2.5 bathrooms including a clawfoot tub. A walk out basement for easy access to store patio furniture. Ample storage or potential for a workshop. There is a generator on site, 2 bay attached garage and barn/stables down below the property. The majority of the property is open and mowed to perfection. This estate has been well maintained and in a superior location. Killington/Pico and Okemo a short distance. Easy access to historic Woodstock, championship golf, tennis, cross country skiing and shopping. Come take a look. Not many properties with this exceptional view!

915 Peterkin Hill Rd, Woodstock

$1,795,000

HILLSIDE FARM - SOUTH WOODSTOCK, VERMONT. Hillside Farm estate presents an exceptional opportunity to embrace the quintessential Vermont country lifestyle on 10.1 picturesque acres in prestigious South Woodstock. Offered TURNKEY and FULLY FURNISHED, the sale includes an extraordinary array of shop equipment, mechanical equipment and property-maintenance and recreational equipment. Built by a master craftsman and builder, the residence showcases handsome timber-frame construction, warm woodwork and enduring craftsmanship throughout. Rolling meadows and pastures, woodland, two streams and a scenic pond create an idyllic setting for equestrian, agricultural and recreational pursuits. At the heart of the home, the spacious country kitchen features cherry cabinetry, gas cooktop, and an antique Stewart woodstove. The 20’ x 18’ great room offers wide pine floors, exposed framing and a soaring cathedral ceiling, overlooking a lovely 14 foot deep pond and scenic vista. The primary suite includes double closets and an ensuite bath with radiant heat, Jacuzzi tub and shower. Additional bedrooms, dining room, and a home office provide flexible living space. The lower level offers a game room with woodstove and pool table, a small kitchenette, and 3/4 bath. The property is remarkably well equipped with a greenhouse, two-stall horse stable, multiple barns and outbuildings, garage workshop, mechanic’s shop, and a substantial 23’ x 35’ woodworking shop. Tucked into the woods is a delightful rustic cabin complete with kitchenette, woodstove, porch and nearby outhouse; an inviting retreat surrounded by nature and set just above one of two babbling brooks. Located in the heart of South Woodstock’s celebrated horse country, Hillside Farm enjoys proximity to the renowned GMHA and the area’s extensive network of scenic riding trails. This is a rare opportunity to own a gentleman's farm that is move-in ready for a VT homestead or second home. Photos electronically decluttered.

3 Beds ⋅ 4 Baths ⋅ 5111623 MLS

HILLSIDE FARM - SOUTH WOODSTOCK, VERMONT. Hillside Farm estate presents an exceptional opportunity to embrace the quintessential Vermont country lifestyle on 10.1 picturesque acres in prestigious South Woodstock. Offered TURNKEY and FULLY FURNISHED, the sale includes an extraordinary array of shop equipment, mechanical equipment and property-maintenance and recreational equipment. Built by a master craftsman and builder, the residence showcases handsome timber-frame construction, warm woodwork and enduring craftsmanship throughout. Rolling meadows and pastures, woodland, two streams and a scenic pond create an idyllic setting for equestrian, agricultural and recreational pursuits. At the heart of the home, the spacious country kitchen features cherry cabinetry, gas cooktop, and an antique Stewart woodstove. The 20’ x 18’ great room offers wide pine floors, exposed framing and a soaring cathedral ceiling, overlooking a lovely 14 foot deep pond and scenic vista. The primary suite includes double closets and an ensuite bath with radiant heat, Jacuzzi tub and shower. Additional bedrooms, dining room, and a home office provide flexible living space. The lower level offers a game room with woodstove and pool table, a small kitchenette, and 3/4 bath. The property is remarkably well equipped with a greenhouse, two-stall horse stable, multiple barns and outbuildings, garage workshop, mechanic’s shop, and a substantial 23’ x 35’ woodworking shop. Tucked into the woods is a delightful rustic cabin complete with kitchenette, woodstove, porch and nearby outhouse; an inviting retreat surrounded by nature and set just above one of two babbling brooks. Located in the heart of South Woodstock’s celebrated horse country, Hillside Farm enjoys proximity to the renowned GMHA and the area’s extensive network of scenic riding trails. This is a rare opportunity to own a gentleman's farm that is move-in ready for a VT homestead or second home. Photos electronically decluttered.

6405 Folding Hills Rd, Woodstock

$1,750,000

EATON HOUSE- Steeped in history and ideally situated in Woodstock’s Historic District, the Eaton House is a handsome Greek Revival-inspired residence built in 1856. Set on a beautifully landscaped .55-acre lot bordering the lovely Kedron Brook, the property offers a rare combination of historic character, modern comfort, and effortless Village living. The interiors are bright and charming, seamlessly blending architectural details with thoughtful updates. The main level is designed for both everyday living and entertaining, with a well-appointed kitchen and dining area complemented by a gracious formal dining room featuring built-in china cabinets and French doors. Adjacent the dining room at the front of the house is a formal sitting room, while across the foyer, a spacious living room with built-in bookshelves centers around a cozy fireplace. Upstairs, five bedrooms and two baths provide generous accommodations for family and friends. Outside, a private deck off the kitchen offers a peaceful setting for outdoor dining and hosting social gatherings. An attached two-car garage and upgraded mechanical systems, including mini-splits for heating and cooling, add modern convenience. Just a short stroll from Woodstock Village’s acclaimed shops, restaurants, galleries, cultural, and recreational offerings, this exceptional property captures the timeless appeal of Village living while offering the comfort and functionality of today. Enjoy the annual Wassail Parade from your own front porch, and view of the Mount Tom Star from the ell of the house. Note: some photos virtually adjusted.

5 Beds ⋅ 3 Baths ⋅ 5113873 MLS

EATON HOUSE- Steeped in history and ideally situated in Woodstock’s Historic District, the Eaton House is a handsome Greek Revival-inspired residence built in 1856. Set on a beautifully landscaped .55-acre lot bordering the lovely Kedron Brook, the property offers a rare combination of historic character, modern comfort, and effortless Village living. The interiors are bright and charming, seamlessly blending architectural details with thoughtful updates. The main level is designed for both everyday living and entertaining, with a well-appointed kitchen and dining area complemented by a gracious formal dining room featuring built-in china cabinets and French doors. Adjacent the dining room at the front of the house is a formal sitting room, while across the foyer, a spacious living room with built-in bookshelves centers around a cozy fireplace. Upstairs, five bedrooms and two baths provide generous accommodations for family and friends. Outside, a private deck off the kitchen offers a peaceful setting for outdoor dining and hosting social gatherings. An attached two-car garage and upgraded mechanical systems, including mini-splits for heating and cooling, add modern convenience. Just a short stroll from Woodstock Village’s acclaimed shops, restaurants, galleries, cultural, and recreational offerings, this exceptional property captures the timeless appeal of Village living while offering the comfort and functionality of today. Enjoy the annual Wassail Parade from your own front porch, and view of the Mount Tom Star from the ell of the house. Note: some photos virtually adjusted.

18 Pleasant St, Woodstock

$1,695,000

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE.

2 Beds ⋅ 3 Baths ⋅ 5084536 MLS

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is comprised of a large, open-format living space with gourmet kitchen, dining and living spaces, plus a first level bedroom with modern ensuite bath. Upstairs is another large open floor plan living space with a half-bath, and a full bedroom with ensuite bath. Each side of the upstairs living space has loft sleeping bunk-areas for kids (of all ages!). SEE DEDICATED PROPERTY WEBSITE FOR VIDEOS, VIRTUAL WALKTHROUGH, FLOORPLANS AND MORE.

2394 Fletcher Hill Rd, Woodstock

$1,645,000

Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former Taftsville Country Store. Expand your living space and use the large, open storefront as a home office or as an entertaining TV /Theatre room (we will even throw in two rows of reclining Theater seats)! The current owners use the place as a second home getaway. The rental offsets would be the Post Office lease (can be cancelled if the space is needed for other ventures) and whatever you choose to do with the smaller Airbnb one bedroom rental. Perfect opportunity for a vacation getaway/combo investment to offset living expenses with this small scale multi-unit property. Just five minutes to the quintessential downtown Village of Woodstock! Property consists of a spacious 3Brm/2Bth two story Owners quarters, storefront space with bath (approved for restaurant, café, or retail store), Post Office (with current lease), smaller one bedroom Apartment/In-Law rental (former AIRBNB rental), and additional storage space for second home toys. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. The historic village of Taftsville is known to be a wonderful community and is a desirable location for home ownership. Must see to appreciate! *Main Level Photos Have Been Electronically Decluttered*

4 Beds ⋅ 4 Baths ⋅ 5096963 MLS

Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colonial is approx. 2,300+/- sq/ft with beautiful old wood flooring, newer kitchen, upgraded systems, and fully furnished. Also included, is an additional 2,500+/- sq/ft (total) of an AirBNB rental/In-Law apartment, along with an active US Postal Service rental space, and generous storefront space in the former Taftsville Country Store. Expand your living space and use the large, open storefront as a home office or as an entertaining TV /Theatre room (we will even throw in two rows of reclining Theater seats)! The current owners use the place as a second home getaway. The rental offsets would be the Post Office lease (can be cancelled if the space is needed for other ventures) and whatever you choose to do with the smaller Airbnb one bedroom rental. Perfect opportunity for a vacation getaway/combo investment to offset living expenses with this small scale multi-unit property. Just five minutes to the quintessential downtown Village of Woodstock! Property consists of a spacious 3Brm/2Bth two story Owners quarters, storefront space with bath (approved for restaurant, café, or retail store), Post Office (with current lease), smaller one bedroom Apartment/In-Law rental (former AIRBNB rental), and additional storage space for second home toys. Current owners have redesigned, paved, and expanded the parking lot to include 21 parking spaces to the south side with four (4) 19Kw Electric Vehicle Charging stations, ADA access to building, and ADA accessible restrooms. Property boasts pretty patio views of the Ottauquechee River and Taftsville Covered Bridge. The historic village of Taftsville is known to be a wonderful community and is a desirable location for home ownership. Must see to appreciate! *Main Level Photos Have Been Electronically Decluttered*

2706 E Woodstock Rd, Woodstock

$1,600,000

The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three luxurious residences in the heart of the Village. Unit B occupies the top two floors and offers over 3,200 square feet of beautifully appointed living space with the feel of a private home. The main level features gracious living and dining rooms with a wood-burning fireplace, a spacious family room, and an en-suite study or guest bedroom with its own fireplace. The kitchen opens to the family room and is filled with southern light. A built-in bar near the dining area leads to a private balcony overlooking the Village and landscaped grounds, perfect for morning coffee or evening entertaining. The upper level opens to a charming landing with built-in bookcases, a serene primary suite, and an ensuite guest bedroom. A rear Carriage House provides covered garage and storage. With timeless character, refined interiors, and walk-to-everything convenience, this is a rare opportunity to own one of Woodstock’s most photographed and cherished historic homes.

3 Beds ⋅ 4 Baths ⋅ 5076786 MLS

The Richmond House Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a proud brick Federal distinguished by its softly weathered rose-hued patina and refined architectural detail. Set on more than an acre behind a classic white picket fence and thoughtfully reimagined under the direction of Laurence Rockefeller, the property comprises three luxurious residences in the heart of the Village. Unit B occupies the top two floors and offers over 3,200 square feet of beautifully appointed living space with the feel of a private home. The main level features gracious living and dining rooms with a wood-burning fireplace, a spacious family room, and an en-suite study or guest bedroom with its own fireplace. The kitchen opens to the family room and is filled with southern light. A built-in bar near the dining area leads to a private balcony overlooking the Village and landscaped grounds, perfect for morning coffee or evening entertaining. The upper level opens to a charming landing with built-in bookcases, a serene primary suite, and an ensuite guest bedroom. A rear Carriage House provides covered garage and storage. With timeless character, refined interiors, and walk-to-everything convenience, this is a rare opportunity to own one of Woodstock’s most photographed and cherished historic homes.

39 Elm St Unit B, Woodstock

$1,595,000

Currently operating as an award winning B&B, this thoughtfully designed, flexibly configured income property is also ideal as a primary residence. Situated at 45 Pleasant Street, just a short stroll from the shops, restaurants and galleries of Woodstock Village, the property overlooks East End Park and the Ottauquechee River Trail, offering an exceptional blend of village convenience as well as natural beauty and outdoor recreation. Inside, historic Vermont charm meets sophisticated contemporary design, with rich finishes, warm hardwood floors, dramatic tilework, custom built-ins and thoughtfully designed lighting throughout. Beautifully appointed baths feature contemporary tile, glass-enclosed showers and upscale finishes reminiscent of a luxury boutique hotel. Guest accommodations offer comfort and privacy, with each principal guest room featuring a king bed, private bath and wet bar equipped with refrigerator, microwave and coffee maker. The expansive 420-square-foot suite includes a separate living room and spa-inspired bath with double vanity, heated floors, heated towel rack and jetted tub. Inviting common areas, a guest lounge, wraparound porch, decks, gardens and fire-pit areas create wonderful spaces for entertaining or relaxation. A dedicated yoga/Pilates studio offers additional flexibility for wellness activities or personal enjoyment. The private upper-level owner's quarters feature two bedrooms, two beautifully appointed baths, a full eat-in kitchen and finished attic space, providing exceptional flexibility for an owner/operator, extended family or full-time residence. Enjoy Woodstock's four-season lifestyle, from skiing and snowshoeing to hiking, golf, cycling and exploring Vermont's scenic countryside. Whether envisioned as a private residence, hospitality venture or investment property, this distinctive offering combines an established rental platform, exceptional location and versatile living spaces. A rare opportunity to make it your own!

5 Beds ⋅ 6 Baths ⋅ 5115063 MLS

Currently operating as an award winning B&B, this thoughtfully designed, flexibly configured income property is also ideal as a primary residence. Situated at 45 Pleasant Street, just a short stroll from the shops, restaurants and galleries of Woodstock Village, the property overlooks East End Park and the Ottauquechee River Trail, offering an exceptional blend of village convenience as well as natural beauty and outdoor recreation. Inside, historic Vermont charm meets sophisticated contemporary design, with rich finishes, warm hardwood floors, dramatic tilework, custom built-ins and thoughtfully designed lighting throughout. Beautifully appointed baths feature contemporary tile, glass-enclosed showers and upscale finishes reminiscent of a luxury boutique hotel. Guest accommodations offer comfort and privacy, with each principal guest room featuring a king bed, private bath and wet bar equipped with refrigerator, microwave and coffee maker. The expansive 420-square-foot suite includes a separate living room and spa-inspired bath with double vanity, heated floors, heated towel rack and jetted tub. Inviting common areas, a guest lounge, wraparound porch, decks, gardens and fire-pit areas create wonderful spaces for entertaining or relaxation. A dedicated yoga/Pilates studio offers additional flexibility for wellness activities or personal enjoyment. The private upper-level owner's quarters feature two bedrooms, two beautifully appointed baths, a full eat-in kitchen and finished attic space, providing exceptional flexibility for an owner/operator, extended family or full-time residence. Enjoy Woodstock's four-season lifestyle, from skiing and snowshoeing to hiking, golf, cycling and exploring Vermont's scenic countryside. Whether envisioned as a private residence, hospitality venture or investment property, this distinctive offering combines an established rental platform, exceptional location and versatile living spaces. A rare opportunity to make it your own!

45 Pleasant St, Woodstock

$1,395,000

Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements. At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed natural bluestone radiant heat flooring, complemented by thoughtfully updated baths, including one with a beautifully executed marble walk-in shower. A dramatic new three-story addition, wrapped in oversized casement windows, introduces abundant natural light and generous new living space while creating a compelling architectural counterpoint to the original home. Nearly every major element has been addressed: new ultra-durable Everlast Advanced Composite siding, interior paint, new roof, all new windows, heat and AC pumps throughout, and a whole-house generator provide the comfort, efficiency, and peace of mind of a thoroughly updated property. Outside, the setting is quintessential Vermont. A new natural bluestone patio and walkway open to an expansive, level lawn bordered by the Kedron Valley Brook, where natural swimming holes invite summer afternoons by the water. Established landscaping, a pond, firepit, and the sound of the brook create an unexpectedly private retreat remarkably close to town. The property also features a historic 2,100-square-foot classic red barn with approved septic plans, offering incredible potential for unique expansion. Just minutes from Woodstock Village, with excellent proximity to the Mt. Peg trail system, Woodstock Inn & Resort amenities, and GMHA, this is a rare opportunity to enjoy the soul and craftsmanship of an historic Vermont home with the ease, light, and livability of a comprehensive modern renovation. Old Vermont soul. Entirely new chapter. Showings begin Saturday, 9/19/2026, with an open house from 1-3:30.

4 Beds ⋅ 3 Baths ⋅ 5110412 MLS

Historic character, beautifully reimagined for modern Vermont living. Minutes from Woodstock Village, this extensively renovated four-bedroom home pairs the warmth and authenticity of its 150-year-old wide-pine floors and exposed beams with a remarkable collection of recent improvements. At the heart of the home is a brand-new, high-end kitchen with Bosch appliances and newly installed natural bluestone radiant heat flooring, complemented by thoughtfully updated baths, including one with a beautifully executed marble walk-in shower. A dramatic new three-story addition, wrapped in oversized casement windows, introduces abundant natural light and generous new living space while creating a compelling architectural counterpoint to the original home. Nearly every major element has been addressed: new ultra-durable Everlast Advanced Composite siding, interior paint, new roof, all new windows, heat and AC pumps throughout, and a whole-house generator provide the comfort, efficiency, and peace of mind of a thoroughly updated property. Outside, the setting is quintessential Vermont. A new natural bluestone patio and walkway open to an expansive, level lawn bordered by the Kedron Valley Brook, where natural swimming holes invite summer afternoons by the water. Established landscaping, a pond, firepit, and the sound of the brook create an unexpectedly private retreat remarkably close to town. The property also features a historic 2,100-square-foot classic red barn with approved septic plans, offering incredible potential for unique expansion. Just minutes from Woodstock Village, with excellent proximity to the Mt. Peg trail system, Woodstock Inn & Resort amenities, and GMHA, this is a rare opportunity to enjoy the soul and craftsmanship of an historic Vermont home with the ease, light, and livability of a comprehensive modern renovation. Old Vermont soul. Entirely new chapter. Showings begin Saturday, 9/19/2026, with an open house from 1-3:30.

2033 South Rd, Woodstock

$1,395,000

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4 bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

5 Beds ⋅ 4 Baths ⋅ 5089552 MLS

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4 bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

1522 Barnard Rd, Woodstock

$1,195,000

This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and resort amenities. The home has overlooked the Ottauquechee River and the former Woodstock woolen mill since 1890. The old mill has long since been repurposed as a children’s daycare center surrounded by community pools, basketball courts, and the Town’s recreation center. On long summer days, the joyful sounds of children enjoying the wide sand beach and swimming holes float up from the river below. Over the years, the floor plan has been adapted on all three levels to modern lifestyles. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The home, like many in Woodstock Village, was damaged in August 2011 by Hurricane Irene. The property is not in the designated 100-Year floodplain that requires insurance. Irene was a FEMA-designated 500-year flood event that affected the basement; afterward, the owners replaced the lower-level sheetrock and the heating boiler and restored the riverbank.

4 Beds ⋅ 3 Baths ⋅ 5100512 MLS

This wonderful Vermont Cape-style home is a peaceful hideaway with amazing views upriver towards Killington is within walking distance of Village shops, restaurants, and resort amenities. The home has overlooked the Ottauquechee River and the former Woodstock woolen mill since 1890. The old mill has long since been repurposed as a children’s daycare center surrounded by community pools, basketball courts, and the Town’s recreation center. On long summer days, the joyful sounds of children enjoying the wide sand beach and swimming holes float up from the river below. Over the years, the floor plan has been adapted on all three levels to modern lifestyles. The main level, entered from the garden walkway or garage, connects to an open country kitchen via a mudroom, which flows into the dining area and living room, offering extraordinary upriver views west toward Killington. A spacious main-floor primary bedroom with an en suite bath opens to a riverside deck, and an expanse of lawn and gardens surrounds the residence. Upstairs are two large bedrooms with a shared bath and a reading loft overlooking the living room below. The walkout lower level includes another bedroom, a bath, a recreation room, and a laundry. The home, like many in Woodstock Village, was damaged in August 2011 by Hurricane Irene. The property is not in the designated 100-Year floodplain that requires insurance. Irene was a FEMA-designated 500-year flood event that affected the basement; afterward, the owners replaced the lower-level sheetrock and the heating boiler and restored the riverbank.

16 Church St, Woodstock

$1,050,000

OPEN HOUSE - SUNDAY 10/11 - 10:00AM TO 12:00PM. Perched high above the valley on 5 private acres, 81 Meadow Lane offers one of the most spectacular panoramic mountain view settings in the White Mountains. With over 90 degrees of unobstructed views stretching across Franconia Notch and the surrounding peaks, this extraordinary property combines exceptional privacy with easy access to Lincoln, Woodstock, Loon Mountain Resort, hiking, golf, and year-round recreation. Blending historic New England character with thoughtful modern updates, the home has been carefully maintained and improved while preserving its timeless appeal. Warm, inviting living spaces, handcrafted details, and expansive windows create the perfect backdrop for gathering with family and friends after a day spent exploring the mountains. A truly rare offering, the property is configured in a unique tri-plex-style layout connected by enclosed breezeways, providing outstanding flexibility for today's buyers. With three full kitchens and accommodations for 18+ guests, it's ideally suited as a luxury vacation home, multi-generational retreat, corporate getaway, or income-producing investment with outstanding short-term rental potential. The thoughtful design allows large groups to enjoy time together while still providing privacy and separate living spaces. Major updates include standing seam metal roofing, updated electrical, plumbing, and heating systems, along with the added security of a whole-home standby propane generator, providing comfort and peace of mind in every season. Whether you're searching for an unforgettable second home, a one-of-a-kind family compound, or a versatile investment property in one of New Hampshire's premier four-season destinations, 81 Meadow Lane is a rare opportunity to own an exceptional mountaintop retreat where breathtaking sunsets, unmatched privacy, and endless mountain adventures await.

5 Beds ⋅ 4 Baths ⋅ 5097556 MLS

OPEN HOUSE - SUNDAY 10/11 - 10:00AM TO 12:00PM. Perched high above the valley on 5 private acres, 81 Meadow Lane offers one of the most spectacular panoramic mountain view settings in the White Mountains. With over 90 degrees of unobstructed views stretching across Franconia Notch and the surrounding peaks, this extraordinary property combines exceptional privacy with easy access to Lincoln, Woodstock, Loon Mountain Resort, hiking, golf, and year-round recreation. Blending historic New England character with thoughtful modern updates, the home has been carefully maintained and improved while preserving its timeless appeal. Warm, inviting living spaces, handcrafted details, and expansive windows create the perfect backdrop for gathering with family and friends after a day spent exploring the mountains. A truly rare offering, the property is configured in a unique tri-plex-style layout connected by enclosed breezeways, providing outstanding flexibility for today's buyers. With three full kitchens and accommodations for 18+ guests, it's ideally suited as a luxury vacation home, multi-generational retreat, corporate getaway, or income-producing investment with outstanding short-term rental potential. The thoughtful design allows large groups to enjoy time together while still providing privacy and separate living spaces. Major updates include standing seam metal roofing, updated electrical, plumbing, and heating systems, along with the added security of a whole-home standby propane generator, providing comfort and peace of mind in every season. Whether you're searching for an unforgettable second home, a one-of-a-kind family compound, or a versatile investment property in one of New Hampshire's premier four-season destinations, 81 Meadow Lane is a rare opportunity to own an exceptional mountaintop retreat where breathtaking sunsets, unmatched privacy, and endless mountain adventures await.

81 Meadow Ln, Woodstock

$975,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of the end Unit D, and some are virtually staged. Units A and D are end units, and Units B and C are interior units.

3 Beds ⋅ 4 Baths ⋅ 5065227 MLS

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of the end Unit D, and some are virtually staged. Units A and D are end units, and Units B and C are interior units.

26 Mt Peg Rd Unit A, Woodstock

$975,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of end Unit D, and some photos are virtually staged. Units A and D are end units, and Units B and C are interior units.

3 Beds ⋅ 4 Baths ⋅ 5065225 MLS

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of end Unit D, and some photos are virtually staged. Units A and D are end units, and Units B and C are interior units.

26 Mt Peg Roa Unit D, Woodstock

$899,900

Mountainside Road really leans into the Mountain get-away theme of New Hampshire. This property is currently being used as an Air B & B, featuring a main house with 4 bedrooms that can be combined with or leased separately with a studio apartment that has its own kitchen, bath, porch and private entry. The home offers great White Mountain Views, is directly across the Street from Lost River (swimming and waterfalls) and providing easy access to all the Lincoln / Woodstock attractions and Loon Mountain skiing. This was a primary home for decades, and the apartment was added for a caretaker to live on site. It has been meticulously updated and maintained through the years and a whole house generator provided comfort on those harsh winter nights. The Cottage or shed structure offers a place for projects or additional storage.

5 Beds ⋅ 4 Baths ⋅ 5104119 MLS

Mountainside Road really leans into the Mountain get-away theme of New Hampshire. This property is currently being used as an Air B & B, featuring a main house with 4 bedrooms that can be combined with or leased separately with a studio apartment that has its own kitchen, bath, porch and private entry. The home offers great White Mountain Views, is directly across the Street from Lost River (swimming and waterfalls) and providing easy access to all the Lincoln / Woodstock attractions and Loon Mountain skiing. This was a primary home for decades, and the apartment was added for a caretaker to live on site. It has been meticulously updated and maintained through the years and a whole house generator provided comfort on those harsh winter nights. The Cottage or shed structure offers a place for projects or additional storage.

5 & 7 Mountainside Rd, Woodstock

$875,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of the end Unit D, and some photos are virtually staged. Units A and D are end units, and Units B and C are interior units.

3 Beds ⋅ 4 Baths ⋅ 5065230 MLS

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of the end Unit D, and some photos are virtually staged. Units A and D are end units, and Units B and C are interior units.

26 Mt Peg Rd Unit B, Woodstock

$875,000

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of the end Unit D, and some photos are virtually staged. Units A and D are end units, and Units B and C are interior units.

3 Beds ⋅ 4 Baths ⋅ 5065228 MLS

Introducing the Mt Peg Condos – Beautifully situated at the foot of Mt. Peg in the Village of Woodstock! Rare opportunity to enjoy a turn-key, new construction condo in a prime location that offers ease of access to and year-round enjoyment of a plentitude of options for recreating, dining, shopping, theatre, and the arts. A light-filled main level interior with white oak flooring sets the stage for the open kitchen/dining/living area. The centrally located kitchen offers copious counter space and a spacious island for dining and food prep all of which are detailed with handsome jet mist granite counter tops. An office/media room and half bath complete the main level. The upper level continues with the white oak flooring and offers two ensuite bedrooms. A third bedroom, full bath, laundry room, and storage room complete the walkout lower level. Take in captivating views of Mt. Tom and the Marsh-Billings-Rockefeller National Park from every level of the condo. Hike, bike, and ski the Mt. Peg trails and enjoy a variety of fine dining options just outside your door. Please note that all interior photos are of the end Unit D, and some photos are virtually staged. Units A and D are end units, and Units B and C are interior units.

26 Mt Peg Rd Unit C, Woodstock

$849,000

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in desirable South Woodstock just seven minutes to the Woodstock Green, this home blends comfort, style, and convenience. The open-concept main level brings together the kitchen, dining area, and living room, where a vaulted ceiling and sleek propane fireplace create a warm, contemporary feel. The dining area opens onto a spacious deck and a flat backyard abutting conserved land, offering peaceful views and serene outdoor relaxation. A updated 1st-floor den/office provides flexibility and could easily serve as a 4th bedroom. Upstairs, the primary bedroom features a walk-in closet and a newly updated ensuite bath with elegant glass-tile walls. Two additional bedrooms share a renovated hallway bath. The finished lower level includes a dedicated laundry room and two rooms perfect as game/rec/gym/play rooms or offices. The attached two-car garage leads into a practical mudroom with built-in benches, hooks, and cubbies, ideal for Vermont living. With excellent mechanical systems, a full-house automatic generator, and updates already completed, this home offers effortless ownership in a prime location. If you’re seeking a turnkey, stylishly updated home just minutes from town, this South Woodstock gem is the one!

3 Beds ⋅ 3 Baths ⋅ 5094379 MLS

This beautifully renovated, truly move-in-ready home has been thoughtfully updated throughout including a brand-new kitchen, refreshed flooring, modernized bathrooms, fresh interior paint, a new garage door, an automatic full-house generator, and more. The property is offered FULLY TURNKEY, with nearly all furniture and furnishings conveying with the sale (artwork excluded). Privately sited in desirable South Woodstock just seven minutes to the Woodstock Green, this home blends comfort, style, and convenience. The open-concept main level brings together the kitchen, dining area, and living room, where a vaulted ceiling and sleek propane fireplace create a warm, contemporary feel. The dining area opens onto a spacious deck and a flat backyard abutting conserved land, offering peaceful views and serene outdoor relaxation. A updated 1st-floor den/office provides flexibility and could easily serve as a 4th bedroom. Upstairs, the primary bedroom features a walk-in closet and a newly updated ensuite bath with elegant glass-tile walls. Two additional bedrooms share a renovated hallway bath. The finished lower level includes a dedicated laundry room and two rooms perfect as game/rec/gym/play rooms or offices. The attached two-car garage leads into a practical mudroom with built-in benches, hooks, and cubbies, ideal for Vermont living. With excellent mechanical systems, a full-house automatic generator, and updates already completed, this home offers effortless ownership in a prime location. If you’re seeking a turnkey, stylishly updated home just minutes from town, this South Woodstock gem is the one!

358 Cowdrey Path, Woodstock

$845,000

Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm office, hay and dairy barns, multiple storage and ancillary structures. Whether looking to engage in the localvore food movement or looking to build a residential home on arguably the most desirable land parcel a stones throw from Woodstock Village, this property has location, setting and features that would be hard to replicate. The upper pasture with easy access has great views, privacy and a commanding location.

2 Beds ⋅ 1 Baths ⋅ 4913852 MLS

Randall Road Farm represents a rare opportunity to purchase a multigenerational family farmstead in an exceptionally desirable location. Long recognized as a well established farm raising Charolais beef cattle, poultry and hay. The owner has been the farmer/steward of many of the areas farms in the Woodstock and South Woodstock. The property has a single family dwelling, shop building with farm office, hay and dairy barns, multiple storage and ancillary structures. Whether looking to engage in the localvore food movement or looking to build a residential home on arguably the most desirable land parcel a stones throw from Woodstock Village, this property has location, setting and features that would be hard to replicate. The upper pasture with easy access has great views, privacy and a commanding location.

234 Randall Rd, Woodstock

$779,000

A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant open area and then curves a short distance up through softwood trees. Opening from those trees is the unexpected surprise! A large sunny meadow is revealed that is bordered by a wide meandering brook! This totally private meadow is within walking distance of the center of Woodstock and yet is quite invisible to passers by! A septic system designer has conducted a "perc test" investigation and believes it can support construction of an in ground septic system. A building lot that simply can not be duplicated within Woodstock! Visually well separated from this 4 acres the 2nd component of the 6 acre parcel is a well known 2 acre level area that for many years hosted the Saturday Woodstock Farmer's Marketplace. A location that presents convenient level walking to access the numerous amenities of Woodstock Village as well as to the endless recreational opportunities of the Billings- Rockefeller National Historical Park! This level parcel of land benefits from COMMERCIAL ZONING! Excellent access, a large level surface, and high visibility! Commercially zoned land is scarce in Woodstock!

4945272 MLS

A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both COMMERCIAL and RESIDENTIAL use! The 6 acres visually divide into 2 components with 2 diverse personalities. The 1st component is an extraordinary private building lot in the heart of Woodstock! Access to this 4 acre component initially leads through a pleasant open area and then curves a short distance up through softwood trees. Opening from those trees is the unexpected surprise! A large sunny meadow is revealed that is bordered by a wide meandering brook! This totally private meadow is within walking distance of the center of Woodstock and yet is quite invisible to passers by! A septic system designer has conducted a "perc test" investigation and believes it can support construction of an in ground septic system. A building lot that simply can not be duplicated within Woodstock! Visually well separated from this 4 acres the 2nd component of the 6 acre parcel is a well known 2 acre level area that for many years hosted the Saturday Woodstock Farmer's Marketplace. A location that presents convenient level walking to access the numerous amenities of Woodstock Village as well as to the endless recreational opportunities of the Billings- Rockefeller National Historical Park! This level parcel of land benefits from COMMERCIAL ZONING! Excellent access, a large level surface, and high visibility! Commercially zoned land is scarce in Woodstock!

Barnard Rd, Woodstock

$750,000

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is truly the highlight, with a picturesque pond, perennial gardens, open pasture, and a mix of wooded acreage offering endless opportunities for recreation, gardening, or simply enjoying the outdoors. All of this is just minutes from Woodstock Village, world-class skiing, shopping, dining, and everything this sought-after region has to offer.

3 Beds ⋅ 3 Baths ⋅ 5097258 MLS

If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is truly the highlight, with a picturesque pond, perennial gardens, open pasture, and a mix of wooded acreage offering endless opportunities for recreation, gardening, or simply enjoying the outdoors. All of this is just minutes from Woodstock Village, world-class skiing, shopping, dining, and everything this sought-after region has to offer.

1326 Curtis Hollow Rd, Woodstock

$749,000

Enjoy expansive views from every level of this beautifully updated, 3-bedroom, 3-full-bath Blake Hill condominium. As a highly desirable end unit, this property welcomes you with a classic bluestone entryway and a large wrap-around porch perfect for outdoor relaxing. Inside, the multi-level floor plan offers exceptional privacy, with an open-concept main level showcasing soaring vaulted ceilings, a dining area, and a living room centered around a cozy wood-burning fireplace with custom built-ins. The large chef's kitchen features stylish appointments, upscale appliances, and a premium Sub-Zero refrigerator. Adjacent the kitchen is a large bedroom with an attached bath, perfect accommodations for friends or family, while a functional mudroom rounds out the main floor. An en suite primary bedroom and sitting area/office serves as a secluded retreat on the entire second level. The fully finished ground level adds significant living space with a sizable third bedroom, full bath, secondary family room with its own fireplace, and massive extra bonus room with dedicated storage. Residents also enjoy access to the community swimming pool, which was completely updated in the summer of 2026. With its proximity to Woodstock Village and the Upper Valley’s many cultural and recreational offerings, this turnkey property is a must-see. Note: Some photos are virtually staged. Public Open House: Sunday, October 11 from 11am-1pm.

3 Beds ⋅ 3 Baths ⋅ 5113057 MLS

Enjoy expansive views from every level of this beautifully updated, 3-bedroom, 3-full-bath Blake Hill condominium. As a highly desirable end unit, this property welcomes you with a classic bluestone entryway and a large wrap-around porch perfect for outdoor relaxing. Inside, the multi-level floor plan offers exceptional privacy, with an open-concept main level showcasing soaring vaulted ceilings, a dining area, and a living room centered around a cozy wood-burning fireplace with custom built-ins. The large chef's kitchen features stylish appointments, upscale appliances, and a premium Sub-Zero refrigerator. Adjacent the kitchen is a large bedroom with an attached bath, perfect accommodations for friends or family, while a functional mudroom rounds out the main floor. An en suite primary bedroom and sitting area/office serves as a secluded retreat on the entire second level. The fully finished ground level adds significant living space with a sizable third bedroom, full bath, secondary family room with its own fireplace, and massive extra bonus room with dedicated storage. Residents also enjoy access to the community swimming pool, which was completely updated in the summer of 2026. With its proximity to Woodstock Village and the Upper Valley’s many cultural and recreational offerings, this turnkey property is a must-see. Note: Some photos are virtually staged. Public Open House: Sunday, October 11 from 11am-1pm.

264 Blake Hill Rd Unit Z, Woodstock

$699,000

Welcome to Lost Valley! Tucked into a quiet North Woodstock neighborhood, 39 Snow King Road offers a welcoming White Mountains getaway with 3 bedrooms, 2 baths, and thoughtful updates throughout. The kitchen features custom hickory cabinetry and quartz countertops, bringing natural warmth and style to the heart of the home. New windows and doors, a new septic system, and a whole-house water filtration system and softener add everyday comfort and convenience. Whether you’re seeking a year-round residence or a mountain retreat, this home offers a peaceful place to recharge and enjoy the outdoor adventures of the White Mountain National Forest. Come discover your North Country escape!

3 Beds ⋅ 2 Baths ⋅ 5115650 MLS

Welcome to Lost Valley! Tucked into a quiet North Woodstock neighborhood, 39 Snow King Road offers a welcoming White Mountains getaway with 3 bedrooms, 2 baths, and thoughtful updates throughout. The kitchen features custom hickory cabinetry and quartz countertops, bringing natural warmth and style to the heart of the home. New windows and doors, a new septic system, and a whole-house water filtration system and softener add everyday comfort and convenience. Whether you’re seeking a year-round residence or a mountain retreat, this home offers a peaceful place to recharge and enjoy the outdoor adventures of the White Mountain National Forest. Come discover your North Country escape!

39 Snow King Rd, Woodstock

$695,000

Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living space), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4.

3 Beds ⋅ 2 Baths ⋅ 5089949 MLS

Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living space), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4.

47 Pleasant St, Woodstock

$646,500

Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream. About two miles to GMHA and South Woodstock village, one mile to VAST trail. 40 minutes to skiing at Killington, less to Okemos. About 20 minutes to Ascutney Outdoors. Seven miles into Woodstock Village, the golf course and Woodstock Athletic Club. Dartmouth College and Dartmouth Hitchcock are 40 minutes away. Subdivision is in process. FLP partner is a real estate licensee.

5070692 MLS

Country land at the south end of Woodstock reaching from RT 106 to the top of the ridge. Potential for views with clearing at several levels. Trails through the property with access to the GMHA network. Stonewalls and a stream. About two miles to GMHA and South Woodstock village, one mile to VAST trail. 40 minutes to skiing at Killington, less to Okemos. About 20 minutes to Ascutney Outdoors. Seven miles into Woodstock Village, the golf course and Woodstock Athletic Club. Dartmouth College and Dartmouth Hitchcock are 40 minutes away. Subdivision is in process. FLP partner is a real estate licensee.

South Rd, Woodstock

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