Woodstock NH Just Listed (7 Days) Real Estate, Homes, Condos for Sale

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!

11 Maple St, Woodstock

$2,950,000

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

$849,000

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

$10,500

1 Beds ⋅ 2 Baths ⋅ 5092964 MLS

This Quarter Share ownership, one bedroom condo (you have use 1 week per month) is a nicely updated unit located in the Notchbrook building. Step out your door to The Pemi River and just a short stroll to the club house. Inside you'll find 1 bedroom, 2 full baths plus a Jaccuzi tub. Also features a gas fireplace to warm you on cold winter evenings and a full-size kitchen to cook for the entire family. Owning a quarter share is an affordable alternative to whole ownership. This is NOT a time share, you own the actual real estate. Condo fees include all utilities, maintenance and full use of all facilities. Deer Park has a fantastic amenities package which includes a beautiful spring fed pond with beach for swimming, indoor pool, hot tub, racquetball, weight & cardio rooms, tennis courts, ice skating, shuttle bus to Loon Mountain during the ski season and more. There is also an on-site rental program with worldwide RCI Exchange. Sorry, no pets allowed in the quarter share buildings.

164 Deer Park Dr Unit 168D, Woodstock

$395,000

5092107 MLS

Rare opportunity to own 8 +/- acres of land in South Woodstock Village with easy access off of Rt. 106. This parcel is being divided off of a 10.87 acre lot. There is a wonderful , open site ideal for building your dream home offering privacy , trails and a short walk to the South Woodstock Country Store, Kedron Valley Inn , dining at the Ransom Tavern and a swim in the Kedron pond ! 5 miles into Woodstock Village , skiing available at multiple resorts including Okemo and Killington as well as local Saskadena Six. Green Mt. Horse Association is around the corner . The year round access to outdoor activities is endless. Call today for more information and a viewing . Subject to completion of the subdivision of the parcel.

Rte 106, Woodstock

$515,000

3 Beds ⋅ 2 Baths ⋅ 5092031 MLS

$10,000 PRICE REDUCTION on this 3 bedroom unit at The Glen at Deer Park. Furnished 3rd floor unit with vaulted ceilings, skylight, and balcony overlooking the river. Wake up listening to the calming sounds of the river bubbling outside your window. Enjoy all 4 seasons, from skiing at Loon Mountain in winter, to hiking in Franconia Notch in Summer. Or stay right on property and enjoy all the amenities Deer Park has to offer, including 2 beaches, tennis court, and rec center.

45 Riverfront Dr Unit 243, Woodstock

$695,000

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

$1,395,000

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

$220,000

1 Beds ⋅ 1 Baths ⋅ 5089181 MLS

This beautifully updated 1-bed, 1-bath condo offers the perfect combination of modern comfort and an unbeatable mountain-town location. Outdoor enthusiasts will appreciate the prime location between Loon & Cannon Mountains, with hiking, skiing, and recreational trails accessible right from your doorstep. Summertime activities include mountain biking cycling, camping, and opportunities to explore local swimming holes along the Pemigewassett River and beyond!. Ideally situated on Main Street in downtown North Woodstock, you’ll enjoy being just steps from local restaurants, breweries, coffee shops, & charming boutiques, while also being minutes from amenities in vibrant downtown Lincoln. Fully renovated at the end of 2024, this unit showcases an open concept layout with lots of natural light, brand-new flooring, a completely redesigned kitchen & full bathroom, updated plumbing, a newly installed water heater, and is being offered almost fully furnished, delivering a truly turnkey, move-in-ready experience. The bedroom is spacious and large enough for a king-sized bed and dressers, and has a walk-in closet. As a desirable 1st-floor unit, the condo features dual entry points for added convenience and easy accessibility. Additional highlights include low HOA fees, a private porch with outdoor storage closet, and convenient on-site laundry within the building. There is also a separate closet in the building for bike storage if desired. The association is pet friendly & allows rentals with a 30-day minimum, offering excellent flexibility for extended stays or investment potential while maintaining a welcoming residential atmosphere. Whether you’re searching for a full-time residence, weekend retreat, or investment opportunity in one of New Hampshire’s most sought-after destinations, this turnkey condo offers the very best of mountain living with downtown convenience.

193 Main St Unit 115, Woodstock

$6,673,000

5 Beds ⋅ 4 Baths ⋅ 5089158 MLS

Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain views, arriving at Birch Tree Farm. Spanning more than 465 acres, this extraordinary Vermont retreat offers an immersive four-season lifestyle -- from pressing fresh cider from the orchard and tapping maple trees for syrup to harvesting honey and gathering fresh eggs for breakfast. Miles of trails traverse varied terrain, including the summit of Old Baldy Mountain (2,409 feet). The retreat includes a lodge-style residence, a modern barn, and several ancillary farm buildings. The wood and stone lodge-style home carries a relaxed mountain vibe. Thoughtfully renovated in 2026, the interiors balance scale and warmth: exposed beams, a cathedral ceiling in the great room, and a substantial wood-burning stone fireplace anchor the space, while floor-to-ceiling windows draw in sweeping views of the mountains. The wrap-around deck takes in an infinity pool, hot tub, and stocked pond. In spring, wild lupine carpet the meadow; in autumn, the apple orchard comes into its own. Landscape design by Shep Butler includes 10’ hydrangea bushes, perennials gardens, stone walls and a walled vegetable garden. The three-level bank barn, designed by award winning Boston architect John MacDonald and built by Housewright Construction, offers one of the finest barns in area with 7 box stalls, a farm manager’s office/tack room, and a versatile upper level for entertaining, recreation, and movie night as well as accommodating an overflow of guests. Nine fenced pastures, run-in sheds, chicken coop, apiary, and direct access to GMHA’s trail network support an exceptional equestrian and recreational lifestyle. 157 acres conserved by VLT. 3.1 miles from GMHA, 3.8 miles from South Woodstock Country Store and Post Office, Less than a half hour from Killington, 2.5 hours from Boston.

2358 Long Hill Rd, Woodstock

$429,000

5088279 MLS

Incredible location! 60+ acres situated on the corner of South Rd. (106) and Noah Wood Rd. in beautiful South Woodstock. The land rises from the roads to the crest of the hilltop with amazing view potential looking to the Northeast. Multiple building sites can be found throughout the property which offers great recreational opportunities including direct access to the VAST trail on the lower corner. Parcel is mostly wooded with a large Maple Grove currently tapped by a local syrup producer. Green Mountain Horse Assoc. is just around the bend and the South Woodstock Country Store and Kedron Valley Inn are just a few minutes away. Woodstock Village is 6 miles down the road. Amazing spot to build your primary residence or second home getaway.

Noah Wood Road, Woodstock

$595,000

4 Beds ⋅ 2 Baths ⋅ 5088170 MLS

A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location!

11 Maple St, Woodstock

$2,500,000

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

$345,000

5085318 MLS

Your dream home starts right here with a blank canvas in one of Vermont's most coveted communities. This exceptional buildable lot on Oak Ridge Way presents a rare opportunity to design and construct your ideal residence on a quiet side road in Woodstock. Nestled within a highly sought-after neighborhood, surrounded by million dollar homes, this property offers the kind of setting that inspires architects and homeowners alike. Picture your morning coffee on a wraparound porch, overlooking the existing neighboring pond and seasonal splendor that make this corner of New England absolutely legendary. The generous lot size provides ample outdoor space for landscaping, gardens, recreational areas, or whatever your imagination conjures. A septic permit is already in place and a house site has been cleared removing two of the biggest hurdles in the building process and letting you move forward with confidence and momentum. The surrounding community adds tremendous value to daily life here. Outdoor enthusiasts will appreciate nearby Aqueduct Trails for recreation and exploration, while the breathtaking Quechee Gorge is just a short drive away. The beloved Woodstock Farmers'Market keeps your kitchen stocked with fresh, local goodness all season long or spend the day downtown shopping in the unique shops and restaurants plus it's just a short drive to I89. Opportunities like this in Woodstock don't sit around waiting. Contact us today to learn more about this remarkable lot and start turning your vision into reality.

Oak Ridge Way, Woodstock

$1,695,000

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

$11,250

1 Beds ⋅ 2 Baths ⋅ 5083900 MLS

One bedroom, 2 bathroom, gas fireplace, fully furnished and ready to be enjoyed! Gas fireplace for ambience and A/C. Located on the lower level. Enjoy 13 weeks of ownership on a rotating basis at the highly sought-after Deer Park resort with all the amenities you could ever need. 5 acre spring fed swimming pond with beach, multi-million dollar clubhouse with indoor pool, racquetball courts, tennis, fitness room, etc. Enjoy the skating rink by the club house. Use this quarter share one week of every month, or exchange for a different location for a small fee through RCI or Intervale International. Showings from 11-1 on Fridays only.

164 Deer Park Dr Unit 161D, Woodstock

$450,000

2 Beds ⋅ 3 Baths ⋅ 5077683 MLS

Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a renovated kitchen with small eating area overlooking the back deck. Tall ceilings allow this space to feel spacious with an abundance of natural light. Second floor consisted of a very large primary bedroom with ample closets and sitting area. A full bathroom and the second bedroom is a perfect size for guests. Lower level has a walk out patio with new slider doors, large family room with a small kitchen and eat-in area, spacious laundry and 3/4 bathroom. Newer Buderus boiler. Pets are allowed- Offered furnished with all new custom curtains. Come take a look at this turn key property!

85 Townhouse Way Unit 14, Woodstock

$1,600,000

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

$2,950,000

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

$646,500

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

$875,000

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

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

$975,000

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

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

$349,000

4 Beds ⋅ 2 Baths ⋅ 5063810 MLS

Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean , inviting feel while preserving the home's classic farmhouse charm. An attached barn/ garage offers excellent storage and flexible space for outdoor gear , a workshop, or hobby area--ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just a short drive to the Village Green in Woodstock, the property also provides convenient access to hiking, biking, and skiing at nearby Killington Resort. Whether you are seeking a full time residence or a Vermont getaway , this property offers an excellent opportunity to enjoy one of Vermont's most desirable areas at an attractive price point. Call today for a private viewing.

5798 W Woodstock Rd, Woodstock

$325,000

5063317 MLS

Sweet Spot - 8 acre building lot located within minutes of the Woodstock Village Green! Driveway is in place and a lovely building site has been cleared and power is at site. Wonderful opportunity to build your Vermont getaway or primary residence. Enjoy access to four season recreation, Marsh-Billings-Rockefeller National Park, theatre, arts, dining, shopping and a short commute to all destinations in the vibrant Upper Valley community!

1 Carlton Hill Rd, Woodstock

$2,599,000

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

$5,950,000

4 Beds ⋅ 5 Baths ⋅ 5044620 MLS

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace. At the heart of the home is a chef’s kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with heated viewing area, and a spacious barn perfect for guest quarters, workshop or a car collection. Set between the twin gables, an elevated courtyard with a heated Soake pool creates a seamless indoor-outdoor connection, ideal for sunset reflections in the summer and stargazing in the winter. A 3-bay garage, and stream complete this offering. GMHA, and premier skiing nearby. Additional land available.

412 Skyland Ln, Woodstock

$525,000

5031426 MLS

Discover the perfect blend of privacy and convenience with this exceptional 20.2-acre parcel, combining two lots into one remarkable opportunity. Featuring a 50 foot right-of-way for access, this wooded retreat offers multiple prime building sites. With selective clearing, you can take in breathtaking views in your choice of direction; east, south, north, or west. Located just minutes from South Woodstock, you will enjoy close proximity to the Green Mountain Horse Association, the South Woodstock Country Store, Kedron Valley Inn, and the historic Ransom Tavern. Whether you are looking to build your dream home, a private getaway, or an investment property, this land offers endless potential in a sought-after Vermont setting. Do not miss out on this rare opportunity, schedule your visit today!

00 Long Hill Rd, Woodstock

$865,000

4 Beds ⋅ 3 Baths ⋅ 5052613 MLS

This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide board flooring, horizontal wainscotting, period doors and hardware and a keeping room fireplace. Massive exposed beams substantiate the date of construction. The four bedrooms and three baths include a first floor primary en suite bedroom. Spacious rooms with unusually high ceilings and multi pane windows create a comfortable living space. Beautifully sited and located on the exclusive Randall Road within a grove of ancient sugar maples.

1782 Randall Rd, Woodstock

$779,000

4945272 MLS

A truly unique 6 acre parcel of land conveniently located in the heart of Woodstock! Tremendous development potential! Zoning allows both BUSINESS SERVICE/LIGHT INDUSTRIAL 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 BUSINESS SERVICE/LIGHT INDUSTRIAL zoning! Excellent access, a large level surface, and high visibility! Similarly zoned land is scarce in Woodstock!

Barnard Rd, Woodstock

$845,000

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

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