Bennington County, VT Homes

/51
$1,875,000
- 3 Beds
- 2.5 Baths
- 3,368 Sq Ft
276 Wilcox Hollow Rd, Sandgate, VT 05250

Luxury Timber Frame Estate on 52+ Acres in Southern Vermont. This exceptional custom post-and-beam retreat is privately set amid rolling hardwood forestland, offering expansive mountain views, remarkable privacy, and a rare sense of peace and connection to nature. Designed for both elegance and efficiency, the home features solar panels with two Tesla Powerwalls for optional off-grid

Margretta Fischer

Wohler Realty Group

(802) 521-2796

276 Wilcox Hollow Rd, Sandgate, VT 05250
/19
$2,750 per month
- 2 Beds
- 2 Baths
- 1,910 Sq Ft
- House for Rent
477 Myers Rd, Shaftsbury, VT 05262

Charming circa 1910 two-bedroom unfurnished Vermont Farmhouse in the town of Shaftsbury. Located on a town-maintained road, non-smoking, no pet property, with parking limited to two cars. The included appliances are a washer, dryer, refrigerator, and electric stove. All showings will be scheduled for Wednesday and Thursday afternoons only.

Kristin Comeau

TPW Real Estate

(802) 520-0672

477 Myers Rd, Shaftsbury, VT 05262
/36
$277,737 Sold Feb 18, 2026

109 Watershed Rd, Woodford, VT 05201
- 3 Beds
- 2 Baths
- 1,782 Sq Ft
- Built 1992
Last Sold Summary
- 7% Below List Price
- $156/SF
- 9 Days On Market
Last Listing Agent Faith Rhodes Maple Leaf Realty

109 Watershed Rd, Woodford, VT 05201

/40
Est $1,050,954 Not Listed For Sale

160 Hemlock Ridge Rd, Manchester Center, VT 05255
- 3 Beds
- 3.5 Baths
- 4,139 Sq Ft
- Built 2002
160 Hemlock Ridge Rd, Manchester Center, VT 05255

Last Sold Summary
- 7% Above List Price
- $237/SF
- 4 Days On Market
Last Sold Price $979,000

Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty

/47
$1,500,000
- Land
- 38.57 Acres
- $38,890 per Acre
500 Nims Rd, Dorset, VT 05251

This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 634-4776

500 Nims Rd, Dorset, VT 05251
/31
$6,500 per month
- 4 Beds
- 3.5 Baths
- 2,340 Sq Ft
- House for Rent
294 Green Peak Orchard S, Dorset, VT 05253

Escape to a stunning summer/winter retreat in Southern Vermont, featuring 4 spacious bedrooms and 3.5 baths. Nestled in the heart of nature, this property offers breathtaking mountain views, perfect for relaxation and outdoor adventures. Open-concept living/kitchen area with plenty of seating, a wood burning fireplace, and panoramic mountain views. Kitchen is fully equipped with modern

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 644-7034

294 Green Peak Orchard S, Dorset, VT 05253
/32
$300,000 Sold May 15, 2025

17 Tel Rd, Bennington, VT 05201
- 4 Beds
- 2.5 Baths
- 2,272 Sq Ft
- Built 1970
Last Sold Summary
- $132/SF
- 6 Days On Market
Current Estimated Value $304,848

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

17 Tel Rd, Bennington, VT 05201

/19
Est $310,042 Not Listed For Sale

119 Dewey St, Bennington, VT 05201
- 5 Beds
- 3 Baths
- 3,960 Sq Ft
- Built 1880
119 Dewey St, Bennington, VT 05201

Last Sold Summary
- 9% Above List Price
- $72/SF
- 191 Days On Market
Last Sold Price $285,000

Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

/26
$295,000 Pending
- 6 Beds
- 3 Baths
- 2,640 Sq Ft
235 Elm St Unit 3, Bennington, VT 05201

This three-unit building features one unit per floor and is ideally located downtown. Set back from the road, it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. Highlights include a large back deck, a spacious partially fenced yard, and a shared driveway with MLS #5057051. The seller prefers to sell both properties together. Listing agent is related to the seller.

Erica Hale

Ridgeline Real Estate

(802) 210-4437

235 Elm St Unit 3, Bennington, VT 05201
/37
$8,000 per month
- 3 Beds
- 3 Baths
- 1,980 Sq Ft
- House for Rent
3093 Route 30, Dorset, VT 05251

Wonderful Dorset Village Historic Colonial, private and completely protected by the established vintage tree line that buffers the neighbors and Route 30. Walk to Village location, this property has been fully renovated with updated kitchen and baths. The house is warm and welcoming with front and side covered porch entrance while the rear screened porch creates an expansive summer room to the

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 255-8729

3093 Route 30, Dorset, VT 05251
/30
$345,750 Sold Oct 21, 2025

374 Overlea Rd, North Bennington, VT 05257
- 3 Beds
- 2 Baths
- 1,753 Sq Ft
- Built 1948
Last Sold Summary
- 5% Below List Price
- $197/SF
- 58 Days On Market
Current Estimated Value $354,663

Last Listing Agent Gregory Cutler Four Seasons Sotheby's Int'l Realty

374 Overlea Rd, North Bennington, VT 05257

/19
Not Listed For Sale

3372 Main St, Manchester, VT 05255
- 5 Beds
- 5 Baths
- 3,332 Sq Ft
- Built 1769
3372 Main St, Manchester, VT 05255

Last Sold Summary
- $135/SF
- 57 Days On Market
Last Sold Price $450,000

Last Listing Agent Andrea Kaplan Four Seasons Sotheby's Int'l Realty

/56
$1,750,000
- 6 Beds
- 3 Baths
- 3,340 Sq Ft
215 & 221 Vt Route 30, Dorset, VT 05251

Two homes, multiple barns and outbuildings on 69 incredible acres in Dorset, VT. Nestled in the Green Mountains, 215 Route 30 the 1780s farmhouse featuring 3 bedrooms, 2 baths with 1645 finished sqft. The second building, nestled away from the road is 221 Route 30 built in 1940 with 3 bedrooms and 2 baths. 1800 sqft. The property offers pastoral venues, mature forest, and scenic mountain views. A

Margretta Fischer

Wohler Realty Group

(802) 944-4482

215 & 221 Vt Route 30, Dorset, VT 05251
/60
$12,500 per month
- 4 Beds
- 4.5 Baths
- 4,393 Sq Ft
- House for Rent
163 Taconic Rd, Manchester, VT 05255

Exclusive Taconic Avenue walk to Village Location... Rarely found, Recently Constructed in 2002 this High Country Colonial is on one acre seamlessly blending within the historic district. Aesthetically pleasing among the area's recently restored Houses of the Hildene era, this residence meets all expectations! Deep front porch entry to soaring foyer flanked with formal rooms while the family

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 255-8917

163 Taconic Rd, Manchester, VT 05255
/49
$435,000 Sold Oct 10, 2025

458 Fox Hill Rd, Bennington, VT 05201
- 4 Beds
- 4 Baths
- 3,040 Sq Ft
- Built 2007
Last Sold Summary
- 2% Above List Price
- $143/SF
- 7 Days On Market
Current Estimated Value $436,891

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

458 Fox Hill Rd, Bennington, VT 05201

/31
Est $303,790 Not Listed For Sale

146 Brookside Dr, Stamford, VT 05352
- 3 Beds
- 2 Baths
- 1,836 Sq Ft
- Built 1949
146 Brookside Dr, Stamford, VT 05352

Last Sold Summary
- 6% Above List Price
- $156/SF
- 104 Days On Market
Last Sold Price $285,500

Last Listing Agent Monica Sumner BHG Masiello Brattleboro

/43
$2,300,000
- Land
- 67 Acres
- $34,328 per Acre
215 Vermont 30, Dorset, VT 05251

Opportunities are Knocking! Welcome to an extraordinary 67-acre estate parcel in Dorset, perfectly positioned along Route 30. This remarkable property offers the ultimate trifecta—location, natural beauty, and limitless potential. Bordering a gentle brook and featuring a mix of rolling meadows and scenic mountain logging trails, this raw, untouched farmland is a rare find in one of Vermont’s most

Margretta Fischer

Wohler Realty Group

(802) 300-4271

215 Vermont 30, Dorset, VT 05251
/40
$11,300 per month
- 5 Beds
- 3 Baths
- 4,432 Sq Ft
- House for Rent
303 W View Estates, Manchester, VT 05255

Gorgeous 4,432 Square Foot - 5 bedroom, 3 bath Log Home in the Heart of Manchester and the Green Mountains! You won't find a better equipped, more spacious and luxury home, located in one of the best Winter and Summer vacation spots in Vermont. 1st Floor boasts a beautiful great room with cathedral ceiling, stone fireplace seamlessly flows into an open-concept kitchen/dining area. Great for

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 300-4671

303 W View Estates, Manchester, VT 05255
/7
$345,000 Sold Nov 07, 2025

72 Mckee Rd, Arlington, VT 05250
- 4 Beds
- 2 Baths
- 1,368 Sq Ft
- Built 1985
Last Sold Summary
- 21% Below List Price
- $252/SF
- 127 Days On Market
Current Estimated Value $353,875

Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty

72 Mckee Rd, Arlington, VT 05250

/49
Not Listed For Sale

1000 Bear Mountain Camp Rd, Rupert, VT 05776
1000 Bear Mountain Camp Rd, Rupert, VT 05776

Last Sold Summary
- 72 Days On Market
Last Sold Price $245,000

Last Listing Agent Curtis Trousdale Preferred Properties

/30
$225,000
- 2 Beds
- 1 Bath
- 784 Sq Ft
92 Bourn Brook Rd Unit 67, Manchester Center, VT 05255

2 bedroom, 1 bath townhouse offering a bright open concept layout across two levels. The main level features comfortable living and dining spaces, in-unit laundry, and hardwood flooring. Upstairs you’ll find two nicely sized bedrooms and a full bath. Ideally located in the heart of Manchester Center, just minutes from shopping, dining, schools, and everyday amenities, with easy access to multiple

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 357-7389

92 Bourn Brook Rd Unit 67, Manchester Center, VT 05255
/25
$3,200 per month
- 4 Beds
- 2 Baths
- 1,950 Sq Ft
- House for Rent
78 Franklin Rd, Manchester, VT 05255

AVAILABLE NOW! WINTER RENTAL: '25/'26 As the seasons change, this charming older home in the heart of Manchester Village is ready to welcome you. With its unique traditional elements, this fully furnished home is a perfect retreat for the Winter Season.Bon appetit! Located just a couple of blocks from Manchester's Restaurant Row...Available November 15th '25, through

Kristin Comeau

TPW Real Estate

(802) 300-3752

78 Franklin Rd, Manchester, VT 05255
/28
$398,350 Sold Sep 04, 2025

315 Chester Knoll Dr, Bennington, VT 05201
- 4 Beds
- 2 Baths
- 1,620 Sq Ft
- Built 2025
Last Sold Summary
- $246/SF
- 0 Days On Market
Last Listing Agent Lilli West Maple Leaf Realty

315 Chester Knoll Dr, Bennington, VT 05201

/22
Est $265,941 Not Listed For Sale

494 Atwood Dr, Pownal, VT 05261
- 3 Beds
- 2 Baths
- 2,048 Sq Ft
- Built 2006
494 Atwood Dr, Pownal, VT 05261

Last Sold Summary
- 8% Above List Price
- $120/SF
- 5 Days On Market
Last Sold Price $246,000

Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

/47
$599,000 Under Contract
- 5 Beds
- 3 Baths
- 3,836 Sq Ft
162 Highland Ave, Manchester Center, VT 05255

Easy Investment Opportunity! Three unit multi-family. Great passive income. Turn key money maker! Spacious layout with privacy for each unit. The main level unit offers an open living dining area, three bedrooms, one-bath with mountain views off the spacious deck. The second floor offers two separate one-bedroom, one-bath units. Each unit has its own entrance. The lower level provides storage for

Margretta Fischer

Wohler Realty Group

(802) 317-7820

162 Highland Ave, Manchester Center, VT 05255
/38
$6,000 per month
- 3 Beds
- 3 Baths
- 2,425 Sq Ft
- House for Rent
3436 Main St, Manchester, VT 05254

Summer Rental | July 1 – October 15, 2026 Winter Rental | December 2026 - March 2027Offered for the first time, this exceptional Manchester residence presents a rare opportunity to enjoy refined village living in the heart of Manchester, Vermont. Beautifully renovated and fully furnished, the home artfully blends timeless elegance with modern sophistication.At the center of the home is a

Kristin Comeau

TPW Real Estate

(802) 474-3905

3436 Main St, Manchester, VT 05254
/30
$160,000 Sold Jul 09, 2025

195 Tunnel St, Readsboro, VT 05350
- 2 Beds
- 1.5 Baths
- 1,056 Sq Ft
- Built 1875
Last Sold Summary
- 7% Above List Price
- $152/SF
- 49 Days On Market
Current Estimated Value $179,994

Last Listing Agent Casey Scott Southern Vermont Realty Group

195 Tunnel St, Readsboro, VT 05350

/60
Est $385,377 Not Listed For Sale

145 Main St, Pownal, VT 05261
- 4 Beds
- 2.5 Baths
- 2,032 Sq Ft
- Built 1742
145 Main St, Pownal, VT 05261

Last Sold Summary
- 9% Below List Price
- $209/SF
- 11 Days On Market
Last Sold Price $424,000

Last Listing Agent Nicholas Charest Maple Leaf Realty

/40
$1,245,000
- 4 Beds
- 6 Baths
- 4,272 Sq Ft
1016 West Rd, Manchester Center, VT 05255

Manchester Village...an award winning architect transformed this "Sears & Roebuck" mini farmstead indo Living Art! Masterful execution of architectural detail at every turn. Circular landscaped drive ties the residence, garages, and the an impressive party barn together for year round use. The substantial covered stone porch enters the arts & crafts foyer.. with study to one side, ahead the

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 357-7462

1016 West Rd, Manchester Center, VT 05255
/10
$1,295 per month
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
201 Division St Unit 201, Bennington, VT 05201

Property Id: 2255313This freshly painted, recently renovated 2 bedroom unit, located in a nice neighborhood near downtown, is now available! 1295/month rent. Washer and Dryer hookups in the unit. Heat pump system with multiple heads handles the heat and cooling. Water/Sewer and trash, but not heat, included in the rent as well as one parking space. Owner is willing to consider pets with a

201 Division St Unit 201, Bennington, VT 05201
/26
$155,000 Sold Feb 03, 2026

777 Butternut Gutter, Arlington, VT 05250
- Land
- 10 Acres
- $15,500 per Acre
Last Sold Summary
- 6% Below List Price
- 57 Days On Market
Last Listing Agent Sunny Breen Josiah Allen Real Estate, Inc.

777 Butternut Gutter, Arlington, VT 05250

/32
Est $1,675,679 Not Listed For Sale

40 Nims, Dorset, VT 05251
- 3 Beds
- 3.5 Baths
- 3,507 Sq Ft
- Built 2006
40 Nims, Dorset, VT 05251

Last Sold Summary
- 18% Above List Price
- $405/SF
- 8 Days On Market
Last Sold Price $1,420,000

Last Listing Agent Katherine Zilkha Four Seasons Sotheby's Int'l Realty

/17
$270,000 Pending
- 6 Beds
- 3 Baths
- 2,900 Sq Ft
239 - 241 Elm St, Bennington, VT 05201

Located downtown, this three-unit building it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. The property includes an unfinished space with the potential to add an additional unit, offering great investment upside. Recent updates include a brand-new roof installed this year. Shared driveway with MLS #5057052; seller is seeking to sell both properties together. Listing

Erica Hale

Ridgeline Real Estate

(802) 278-6021

239 - 241 Elm St, Bennington, VT 05201
/36
$40,000 per month
- 4 Beds
- 3 Baths
- 2,791 Sq Ft
- House for Rent
33 Strattonwald Rd, Winhall, VT 05340

Lock in your rental for ski season '26-'27! This cheerful, modern-yet-classic Strattonwald chalet is nestled in a private community just 7 minutes to Stratton's Main Base, with shuttle access. There is so much room for everyone, with two primary bedroom suites plus two more bedrooms; a gourmet open-concept kitchen/dining/living room with wood stove; second living/TV room. Downstairs living room

Jamie Luke TPW Real Estate

33 Strattonwald Rd, Winhall, VT 05340
/7
$75,000 Sold May 20, 2025

00 Vermont 8, Readsboro, VT 05350
- Land
- 31 Acres
- $2,419 per Acre
Last Sold Summary
- 24% Below List Price
- 261 Days On Market
Last Listing Agent Kim Meeker Southern Vermont Realty Group

00 Vermont 8, Readsboro, VT 05350

/40
Est $935,161 Not Listed For Sale

67 Coventry Ln, Manchester Center, VT 05255
- 3 Beds
- 3 Baths
- 2,774 Sq Ft
- Built 1965
67 Coventry Ln, Manchester Center, VT 05255

Last Sold Summary
- 13% Above List Price
- $297/SF
- 10 Days On Market
Last Sold Price $825,000

Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty

/37
$175,000 Under Contract
- 2 Beds
- 1 Bath
- 684 Sq Ft
4355 Sandgate Rd, Arlington, VT 05250

Cozy cabin retreat waiting for you! This rustic two-bedroom, one-bath log home features a beautiful hearth with a stone fireplace and the charm of a true fisherman’s cabin in the woods. Enjoy easy, year-round access via a paved, town-maintained road and a newly constructed driveway leading directly to the home.The property offers waterfront access to the famous Green River—perfect for

Margretta Fischer

Wohler Realty Group

(802) 330-5803

4355 Sandgate Rd, Arlington, VT 05250
/2
$1,100 per month
- 1 Bed
- 1 Bath
- House for Rent
165 Benmont Ave, Bennington, VT 05201

Property Id: 1488761I bed 1 bath small house.The tenants pay their own utilities:heat electric etc…

165 Benmont Ave, Bennington, VT 05201
/34
$175,000 Sold May 16, 2025

106 Park St Unit 8, Bennington, VT 05201
- 2 Beds
- 1.5 Baths
- 1,056 Sq Ft
- Built 1993
Last Sold Summary
- $166/SF
- 9 Days On Market
Current Estimated Value $174,004

Last Listing Agent Vicki Wilson Maple Leaf Realty

106 Park St Unit 8, Bennington, VT 05201

/34
Est $472,506 Not Listed For Sale

32 County Rd, Stamford, VT 05352
- 2 Beds
- 2 Baths
- 1,586 Sq Ft
- Built 1989
32 County Rd, Stamford, VT 05352

Last Sold Summary
- 7% Below List Price
- $322/SF
- 0 Days On Market
Last Sold Price $510,000

Last Listing Agent Rebecca Seymour Brattleboro Area Realty

Showing Results 1 - 40, Page 1 of 18

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