Brownsville, VT Homes

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  /52

  $1,390,000

  • 5 Beds
  • 3.5 Baths
  • 3,953 Sq Ft

  11 College Hill Rd, Woodstock, VT 05091

  Welcome to 11 College Hill Road - Situated in the heart of Woodstock Village, this classic 1919 Gambrel offers space, charm, and incredible views of both the Ottauquechee River and the town's beloved Mount Tom. This beautifully maintained home is perched perfectly above the river with over a half an acre of landscaped outdoor space, including 50 feet of river frontage, mature fruit trees, and

  Zoe Hathorn Washburn Snyder Donegan Real Estate Group

  11 College Hill Rd, Woodstock, VT 05091
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  /20

  $2,800 per month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  21 Central St Unit 3rd floor, Woodstock, VT 05091

  Just now offered for lease is a newly created luxury apartment in the very heart of Woodstock Village! The elevated location, above the hub of central village shopping, presents captivating views of village activity, as well as distant hills. The owners started with a blank slate, in a previously vacant space and have provided all of the benefits of wall to wall new construction. State of the art

  John Wetmore Wetmore Real Estate

  21 Central St Unit 3rd floor, Woodstock, VT 05091
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  /40

  $750,000 Sold May 01, 2025

  • 1,840 Sq Ft
  • $408/SF
  • 43 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1970

  6963 South Rd, Woodstock, VT 05071

  Enchanting cottage perched on a private knoll with short range views. This property consist of 33 acres with a mixture of open meadow and woods for those looking for an afternoon of walking or snowshoeing. It is currently enrolled in the Current Use Forestry program. Stunning perennial gardens enhance the handsome stone walls and stone walk way to the residence. It's a Garden enthusiasts

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  6963 South Rd, Woodstock, VT 05071
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  /40

  Est $1,308,316 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,440 Sq Ft

  4946 South Rd, South Woodstock, VT 05071

  4946 South Rd, South Woodstock, VT 05071
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  /51

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  20 The Green, Woodstock, VT 05091

  Stunning antique cape! Located in the 'heart' of Woodstock. Originally located on Central Street- this home was moved in the 1960's to this location and had an extensive renovation in 2011. The antique brick section was built in 1826- it boasts a spacious living room anchored with a large wood burning fireplace, original wide pine floors and lots of space for entertaining. Adjacent find a

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  20 The Green, Woodstock, VT 05091
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  /36

  $460,000 Sold Apr 18, 2025

  • 2,996 Sq Ft
  • $154/SF
  • 325 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1840

  24 High St, Woodstock, VT 05091

  Constructed in 1840, this post & beam home is situated in the heart of Woodstock Village. A short stroll across the Kedron Brook footbridge to shopping and restaurants, the property is just steps away from all of the amenities this renowned Vermont town has to offer. Woodstock Elementary School, Vail Field and the Woodstock Inn are also just around the corner. Historic High Street, once home to

  Danny Kogut Williamson Group Sothebys Intl. Realty

  24 High St, Woodstock, VT 05091
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  /39

  Est $953,432 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,507 Sq Ft

  433 Cowdrey Path, Woodstock, VT 05091

  433 Cowdrey Path, Woodstock, VT 05091
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  /35

  $1,999,000

  • 5 Beds
  • 4.5 Baths
  • 4,214 Sq Ft

  10 College Hill Rd, Woodstock, VT 05091

  10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in

  John Snyder Snyder Donegan Real Estate Group

  10 College Hill Rd, Woodstock, VT 05091
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  /50

  $1,275,000 Sold Apr 02, 2025

  • 2,584 Sq Ft
  • $493/SF
  • 72 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1985

  1075 Westerdale Rd, Woodstock, VT 05091

  This lovingly maintained property with mountain views has been enjoyed by a single family since its construction in 1985. The open-concept layout is anchored by a stone Rumford fireplace, which along with the southern exposure warms the large easy-to-keep space. The first floor master boasts ample storage with a sliding door for quick access to the grounds. Across from the main house via a

  Keri Cole Williamson Group Sothebys Intl. Realty

  1075 Westerdale Rd, Woodstock, VT 05091
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  /23

  Not Listed For Sale

  0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091

  0 Carlton Hill Rd Unit 4670150, Woodstock, VT 05091
• 

  

  /40

  $2,250,000

  • 5 Beds
  • 3.5 Baths
  • 3,502 Sq Ft

  4945 South Rd, Woodstock, VT 05071

  The John Arnold Cottle House is a landmark residence in the heart of South Woodstock, a rare blend of village convenience and country living. Built in 1811 by one of the area's earliest settlers, this stately Federal-style brick home has been thoughtfully restored to honor its historic charm while integrating modern comforts. Set on 2.7 acres, the property features 450 ft of frontage on Kedron

  Story Jenks LandVest, Inc/Woodstock

  4945 South Rd, Woodstock, VT 05071
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  /39

  $410,000 Sold Apr 01, 2025

  • 1,052 Sq Ft
  • $390/SF
  • 97 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1930

  6 Highland Ave, Woodstock, VT 05091

  A rare opportunity for Woodstock! An affordable Woodstock Village cottage! The advantage of contemporary solar powered energy efficiency, with connection to an energy storing Tesla battery! The property further benefits from valuable infrastructure components of the municipal sewer system and the Woodstock Aqueduct Water Company! An attractive interior features wood flooring throughout! A large

  John Wetmore Wetmore Real Estate

  6 Highland Ave, Woodstock, VT 05091
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  /40

  Est $1,869,466 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 4,410 Sq Ft

  5 Pine St, Woodstock, VT 05091

  5 Pine St, Woodstock, VT 05091
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  /53

  $1,399,000

  • 4 Beds
  • 3.5 Baths
  • 4,228 Sq Ft

  608 Fletcher Hill Rd, Woodstock, VT 05091

  Open House Sunday, April 13, 12:00 to 2:00 - Tucked away in the serene forests of Woodstock, Vermont, this beautifully remodeled 11-room home offers 4 bedrooms, 4 bathrooms, and 4,225 sq. ft. of luxurious living space on 5.4 private acres. The open-concept design is flooded with natural light, featuring a stunning chef’s kitchen with high-end stainless steel appliances, Vermont soapstone

  Sandy Reavill Real Broker LLC

  608 Fletcher Hill Rd, Woodstock, VT 05091
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  /35

  $475,000 Sold Mar 27, 2025

  • 1,424 Sq Ft
  • $334/SF
  • 144 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1971

  378 Fletcher Hill Rd, South Woodstock, VT 05071

  Privately located, in desirable South Woodstock! A comfortable home with the benefit of great outside spaces providing the opportunity for recreation, gardening or entertaining! South Woodstock is well known for the potential of having wonderful access to miles of trails enjoyed by equestrians, hikers and snowmobilers. The numerous amenities of historic Woodstock Village are just minutes away!

  John Wetmore Wetmore Real Estate

  378 Fletcher Hill Rd, South Woodstock, VT 05071
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  /34

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  7429 Us Route 4, Bridgewater, VT 05034

  7429 Us Route 4, Bridgewater, VT 05034
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  /60

  $2,450,000

  • 4 Beds
  • 3.5 Baths
  • 5,573 Sq Ft

  851 Riverside Park Rd, Woodstock, VT 05091

  "All Seasons" is the ultimate Vermont retreat, designed for gatherings and getaways while seamlessly blending rustic charm with modern luxury. This 5,900-sq-ft barn-style home, just over five minutes from Woodstock Village via Route 4 and the Lincoln Covered Bridge, sits high on a knoll above the Ottauquechee River with views to Killington. A veritable mini-resort, the property offers

  Richard Higgerson Higgerson & Company

  851 Riverside Park Rd, Woodstock, VT 05091
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  /24

  $230,000 Sold Mar 26, 2025

  • 856 Sq Ft
  • $269/SF
  • 3 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1984

  29 Heritage Condos Unit 29D, Woodstock, VT 05091

  OPEN HOUSE CANCELLED.A desirable 1 bedroom condo in Woodstock! Just a short distance from the high school, Farmer's Market, and Thompson Senior Center and only a 3 minute drive from the Woodstock town green and less than 12 minutes to Saskadena Six for skiing. The condo association takes care of all the exterior maintenance (minus clearing off the balcony), and provides interior lockable

  Franchesca Collins Hall Collins Real Estate Group

  29 Heritage Condos Unit 29D, Woodstock, VT 05091
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  /27

  Est $762,286 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,579 Sq Ft

  7 Golf Ave, Woodstock, VT 05091

  7 Golf Ave, Woodstock, VT 05091
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  /41

  $1,150,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,698 Sq Ft

  119 English Mills Way, Woodstock, VT 05091

  An expansive 5 bedroom home, in a private location, conveniently just a few minutes drive from Woodstock Village! Among often sought amenities are a ground floor primary bedroom suite with private bath, a dramatic great room with cathedral ceiling and wood burning fireplace, a generously sized lower level in-law/guest suite with kitchen, dining, living room and bedroom with bath, 3 additional

  John Wetmore Wetmore Real Estate

  119 English Mills Way, Woodstock, VT 05091
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  /43

  $700,000 Sold Feb 14, 2025

  • 2,616 Sq Ft
  • $268/SF
  • 15 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  944 College Hill Rd, Woodstock, VT 05091

  PRIVATE- Cape Cod Home less than a mile to Historic Woodstock Village! This generous sized home consisting of 2616 squ ft. sits on 3.62 secluded acres. Built in 1988 and first time on the market- this home has been well maintained with an abundance of light, generous proportioned rooms with handsome hardwood floors. First floor consists of kitchen with quartz counters and soft neutral toned

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  944 College Hill Rd, Woodstock, VT 05091
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  /30

  Est $1,018,013 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,423 Sq Ft

  12 High St, Woodstock, VT 05091

  12 High St, Woodstock, VT 05091
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  /40

  $1,875,000 Pending

  • 10 Beds
  • 12 Baths
  • 7,769 Sq Ft

  2709 W Woodstock Rd, Woodstock, VT 05091

  INVESTMENT, MULTI-GENERATIONAL, MULTI FAMILY AND COMMERCIAL OPPORTUNITY .. priced below appraised value on land and buildings providing instant equity. Experience the charm of Woodstock, VT with its quaint Main Street and enjoy the proximity to Killington Resort, just a short drive away. This exceptional property offers a unique blend of natural beauty and year-round recreational opportunities,

  Susan Bishop Four Seasons Sotheby's Int'l Realty

  2709 W Woodstock Rd, Woodstock, VT 05091
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  /40

  $2,750,000 Sold Feb 13, 2025

  • 6,443 Sq Ft
  • $427/SF
  • 495 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1970

  318 Ebbin Lockwood Way, Woodstock, VT 05071

  Serene, private, contemporary: Sited on a ridge above South Woodstock village, the 54 acre property offers complete seclusion in an elegant setting with an extensive network of trails. The three bedroom main dwelling is sleek and elegant, with an open floor plan crafted to take in the beauty of the site with abundant use of organic material designed to integrate the design with the surrounding

  Story Jenks LandVest, Inc/Woodstock

  318 Ebbin Lockwood Way, Woodstock, VT 05071
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  /38

  Est $543,131 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft

  39 South St, Woodstock, VT 05091

  39 South St, Woodstock, VT 05091
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  /26

  $489,500

  • 2 Beds
  • 1.5 Baths
  • 930 Sq Ft

  11A Prospect St, Woodstock, VT 05091

  Walk to everything Woodstock village has to offer from this sunny condo! Within an easy stroll of the Woodstock Inn, downtown restaurants, farmer's markets, and the Marsh Billings Rockefeller National Park, 11A Prospect is ideal for enjoying the charms of village living. Elevated above the Route 4 on a bucolic neighborhood side street, this well-kept home offers historic details with modern

  Keri Cole Williamson Group Sothebys Intl. Realty

  11A Prospect St, Woodstock, VT 05091
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  /2

  $1,175,000 Sold Jan 29, 2025

  • 2,660 Sq Ft
  • $442/SF
  • 186 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2014

  6453 South Rd, Woodstock, VT 05071

  Round Top Cottage is sited on a knoll just outside the village of South Woodstock on 20 acres, offering complete privacy and views of the rolling hills framing the Kedron Valley. This three-bedroom lodge, fully renovated in 2024, blends modern amenities with rustic elegance. The open floor plan features cathedral ceilings in the main living and dining area, creating an inviting space to gather

  Story Jenks LandVest, Inc/Woodstock

  6453 South Rd, Woodstock, VT 05071
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  /27

  Est $709,018 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft

  37 South St, Woodstock, VT 05091

  37 South St, Woodstock, VT 05091
• 

  

  /3

  $329,900

  • Land
  • 142 Acres
  • $2,323 per Acre

  00 Chateauguay Rd, Woodstock, VT 05091

  Prime land access off Chateauguay Rd with no zoning, HOA, or deed restrictions. Sub-dividable with well and septic needed; electricity nearby. Just 25 minutes from the town of Woodstock’s amenities, parks and historic sites. 20 minutes to Killington Ski Resort and Coolidge State Park, and 30 minutes to Pico Mountain Ski Resort and Lynches River County Park. Perfect for building your dream home or

  Derek Greene Derek Greene

  00 Chateauguay Rd, Woodstock, VT 05091
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  /40

  $4,205,000 Sold Jan 27, 2025

  • 5,939 Sq Ft
  • $708/SF
  • 121 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1797

  327 Fletcher Schoolhouse Rd, Woodstock, VT 05071

  ByBrook Farm: Reimagined, turnkey 1790s farmhouse set in one of Vermont's most loved valleys, perennial gardens, stone walls, a spring fed pond, a brook, and rolling meadows. Quiet luxury. Just outside the hamlet of South Woodstock on 25 acres, the 2-bedroom 4,667 sf farmhouse and the 2-bedroom 1,273 sf guest cottage are connected by a stone pathway through the gardens. In the recent renovations

  Story Jenks LandVest, Inc/Woodstock

  327 Fletcher Schoolhouse Rd, Woodstock, VT 05071
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  /31

  Est $898,216 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,970 Sq Ft

  10 Linden Hill, Woodstock, VT 05091

  10 Linden Hill, Woodstock, VT 05091
• 

  

  /40

  $775,000

  • 4 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  339 Gully Rd, Woodstock, VT 05091

  Peaceful Gully Road Retreat. Just minutes from Woodstock Village.Set on 5.1 private acres along quiet and desirable Gully Road, this beautifully updated four-bedroom, two and one-half bath home offers the perfect blend of peaceful country living and convenient proximity to Woodstock shops, restaurants, and schools.The main level features a light-filled, open-concept layout with a dramatic vaulted

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  339 Gully Rd, Woodstock, VT 05091
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  /37

  $975,000 Sold Jan 10, 2025

  • 2,944 Sq Ft
  • $331/SF
  • 28 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1994

  828 Deerbrook Way, Woodstock, VT 05091

  A gem of a property on 12 spectacular, mostly wooded, acres in the desirable Deerbrook Way area of Woodstock. Four+ miles to all the amenities of Woodstock Village and 8 miles to the Skyship Gondola at Killington. Built in 1994, this custom designed red oak Post and Beam Contemporary provides everything you would want in a primary residence or a get away vacation retreat. Situated on a 12+ acre

  Stan Butler Four Seasons Sotheby's Int'l Realty

  828 Deerbrook Way, Woodstock, VT 05091
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  /40

  Est $1,768,272 Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 3,892 Sq Ft

  28 The Green Unit 30, Woodstock, VT 05091

  28 The Green Unit 30, Woodstock, VT 05091
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  /26

  $650,000

  • Land
  • 78 Acres
  • $8,366 per Acre

  0 Mecawee Rd, Woodstock, VT 05091

  Spectacular 77+ acre parcel on sought after Mecawee Rd. with a perfect combination of level, sloping and hilly terrain. There are multiple building sites including a large cleared area set back off the road with a driveway in place and utilities (electric & fiber optic) at the street. This past Fall, the Sellers went to great lengths to clear the land all the way down to the road opening up

  Dan Noble Snyder Donegan Real Estate Group

  0 Mecawee Rd, Woodstock, VT 05091
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  /14

  $220,000 Sold Jan 08, 2025

  • 1,120 Sq Ft
  • $196/SF
  • 32 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1985

  2176 Bridgewater Center Rd, Bridgewater Corners, VT 05035

  Welcome to this delightful 3-bedroom, 1-bath ranch-style home nestled in the heart of scenic Bridgewater, Vermont. Perfectly situated on a quiet country road, this home offers the quintessential Vermont lifestyle with fresh air, and plenty of outdoor space. The single-level layout is ideal for easy living, featuring a spacious living room with large windows that let in plenty of natural light.

  Katie Ladue Gilbert KW Vermont Woodstock

  2176 Bridgewater Center Rd, Bridgewater Corners, VT 05035
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  /23

  Est $2,198,960 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 6,671 Sq Ft

  22 Prospect St, Woodstock, VT 05091

  22 Prospect St, Woodstock, VT 05091
• 

  

  /60

  $615,000

  • 4 Beds
  • 3 Baths
  • 2,678 Sq Ft

  20 Gully Rd, Woodstock, VT 05091

  AGGRESSIVE PRICE REDUCTION - Classic Vermont Antique Farmhouse just outside of Woodstock Village! c.1903 Dormered Cape set on approx. 2.6 acres of level, open land bordered by a tranquil brook. The property offers a picturesque setting with extensive perennial gardens, a patio by the stream, firepits, covered front porch, rear porch, and deck—perfect for relaxing or entertaining. Inside, the home

  John Bassette Bassette Real Estate Group

  20 Gully Rd, Woodstock, VT 05091
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  /28

  $270,000 Sold Jan 07, 2025

  • 1,328 Sq Ft
  • $203/SF
  • 72 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  823 Goldcoast Rd, Bridgewtr Cor, VT 05035

  Highly desired Bridgewater location on Gold Coast Road minutes to the Killington Skyeship Gondola & Base Lodge, and the beautiful Village of Woodstock. Close to VAST snowmobile trails, and endless hiking/mountain biking trails. Five minutes to the legendary Long Trail Brewery. This 3 bedroom, 2 full bath home is set on 2.6 tranquil, well-maintained acres. The home has an eat in kitchen, spacious

  Marni Rieger KW Vermont-Killington

  823 Goldcoast Rd, Bridgewtr Cor, VT 05035
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  /40

  Est $2,095,413 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,897 Sq Ft

  2 Border Ln, Woodstock, VT 05091

  2 Border Ln, Woodstock, VT 05091

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