Bennington County, VT Homes

/36
$460,000
- 3 Beds
- 2 Baths
- 2,108 Sq Ft
1061 Granger Hollow Rd, North Bennington, VT 05257

Dreaming of a peaceful Vermont lifestyle? This three bedroom, 2 bath home sits on 11.5 acres of beautiful land with rolling open mountain views, a stream, mature apple trees, and an inground pool all the ingredients for your perfect retreat.Step inside to this home that has had a complete refresh. The home offers a first floor bedroom and full bath with a step in shower, making it great

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 481-3292

1061 Granger Hollow Rd, North Bennington, VT 05257
/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
/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 $342,740

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

17 Tel Rd, Bennington, VT 05201

/22
Est $278,979 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,048 Sq Ft
494 Atwood Dr, Pownal, VT 05261

494 Atwood Dr, Pownal, VT 05261

/28
$300,000 Pending
- 3 Beds
- 2 Baths
- 1,188 Sq Ft
72 Sawmill Rd, Pownal, VT 05261

Experience the perfect blend of comfort and functionality in this modern doublewide, built in 2022, offering easy one-level living with upgraded insulation for energy efficiency. Features newer sitework with a drilled well and engineered septic system designed and permitted for 2 bedrooms, meaning 4-person occupancy. This spacious home features three bedrooms, allowing for versatile options using

Gary Fuls Jr

RE/MAX Transitions

(802) 722-7730

72 Sawmill Rd, Pownal, VT 05261
/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
/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
Last Listing Agent Gregory Cutler Four Seasons Sotheby's Int'l Realty

374 Overlea Rd, North Bennington, VT 05257

/60
Est $389,420 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,032 Sq Ft
145 Main St, Pownal, VT 05261

145 Main St, Pownal, VT 05261

/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
/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
/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 $469,213

Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

458 Fox Hill Rd, Bennington, VT 05201

/32
Est $1,572,460 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,507 Sq Ft
40 Nims, Dorset, VT 05251

40 Nims, Dorset, VT 05251

/58
$625,000 Under Contract
- 3 Beds
- 2.5 Baths
- 3,284 Sq Ft
1098 W Sandgate Rd, Arlington, VT 05250

Private, Quiet, and Solidly built timeless Post & Beam 2,200 SF residence on 10.05 acres offering South and Westerly sunlight all day long ending with lovely sunsets! Overlooking a spring fed pond and a mix of open terrain and deciduous slope side forest with trails. The house offers main level all open 40' X 32' great room living / dining/ kitchen with a massive center 2.5 story stone fireplace.

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 992-1723

1098 W Sandgate Rd, Arlington, 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
/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
Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty

72 Mckee Rd, Arlington, VT 05250

/40
Est $940,141 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,774 Sq Ft
67 Coventry Ln, Manchester Center, VT 05255

67 Coventry Ln, Manchester Center, VT 05255

/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
/41
$5,000 per month
- 4 Beds
- 2.5 Baths
- 2,844 Sq Ft
- House for Rent
78 Stoney Fields Rd, Manchester Center, VT 05255

Winter Ski Rental – Enjoy the perfect Vermont winter getaway in this spacious 4 bedroom, 3 bath, 2,844 SF ranch home set on 2.13 private acres, just steps from downtown Manchester Center. Recently refreshed with stylish wallpaper, modern wood floors, and brand new kitchen appliances, this home blends cozy charm with contemporary comfort. Relax on the new expansive deck offering sweeping mountain

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 317-8075

78 Stoney Fields Rd, Manchester Center, 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

/34
Est $502,897 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,586 Sq Ft
32 County Rd, Stamford, VT 05352

32 County Rd, Stamford, VT 05352

/27
$299,900 Under Contract
- 1 Bed
- 1 Bath
- 1,085 Sq Ft
2837 Main St, Manchester Center, VT 05255

Located just off Route 7A near Hildene, The Lincoln Family Home, this charming bungalow offers the perfect balance of in town convenience and a private setting. Set on .82 acres, the home features one bedroom and one full bath with desirable first-floor living, making it ideal for a full time residence or an easy Vermont getaway.This home is filled with charming details and character,

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 712-0520

2837 Main St, Manchester Center, VT 05255
/14
$2,275 per month
- 2 Baths
- 1,120 Sq Ft
- Property for Rent
343 Dewey St, Bennington, VT 05201

Well-maintained provider office space available for lease, offering approx. 1,120 sq ft. Layout includes a waiting room with half bath, reception area, 2 operatories (or rooms), private office, and an additional half bath. Shared kitchen with the adjacent unit. Staff enjoy a separate entrance and designated parking, distinct from the public entry and lot. Rent includes electric, heat/AC,

Peter West

BISHOP WEST REAL ESTATE

(802) 347-1295

343 Dewey St, Bennington, VT 05201
/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

/40
Est $3,258,996 Not Listed For Sale
- 5 Beds
- 7.5 Baths
- 8,700 Sq Ft
440 Marcia Ln, Dorset, VT 05251

440 Marcia Ln, Dorset, VT 05251

/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
/56
$5,000 per month
- 3 Beds
- 2 Baths
- 1,932 Sq Ft
- House for Rent
397 Powderhorn Rd, Manchester Center, VT 05255

SPRING/SUMMER RENTAL: Charming newly renovated ranch with 3 bedrooms, 2 baths is the perfect summer rental, offering a cozy and inviting atmosphere! Conveniently located close to town for easy access to shops and dining. Enjoy a fenced-in backyard with a deck, perfect for grilling and outdoor relaxation. The kitchen and living room are located on the first floor, along with the spacious primary

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 729-7527

397 Powderhorn Rd, Manchester Center, VT 05255
/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

/22
Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,708 Sq Ft
16 Clark Rd, Rupert, VT 05776

16 Clark Rd, Rupert, VT 05776

/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
/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
/48
$395,000 Sold Jan 30, 2025

3310 Vt Rte 346, North Pownal, VT 05260
- 2 Beds
- 1 Bath
- 7,000 Sq Ft
- Built 1898
Last Sold Summary
- 12% Below List Price
- $56/SF
- 94 Days On Market
Last Listing Agent Paul Harsch HARSCH ASSOCIATES

3310 Vt Rte 346, North Pownal, VT 05260

/31
Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,888 Sq Ft
12 Stratton Rd W Unit 12, Winhall, VT 05340

12 Stratton Rd W Unit 12, Winhall, VT 05340

/15
$115,000
- Land
- 2.9 Acres
- $39,655 per Acre
Lot 3 Route 11 30, Winhall, VT 05340

Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 808-6197

Lot 3 Route 11 30, Winhall, VT 05340
/18
$4,500 per month
- 4 Beds
- 3 Baths
- 2,500 Sq Ft
- House for Rent
191 Forest Mountain Rd, Peru, VT 05152

WELCOME TO PERU MOUNTAIN LODGE... Now Available For Your Vermont Summer '25 Vacation! Don't Let This One Get away... Cozy open living area with four Bedrooms. Two bedrooms on the main level, the Main Suite in the loft above, and a fourth bedroom in the finished walk-out basement. This home boasts a cathedral ceiling, an updated cooks kitchen, and a striking stone fireplace with two

Kristin Comeau

TPW Real Estate

(802) 889-8948

191 Forest Mountain Rd, Peru, VT 05152
/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 $197,716

Last Listing Agent Vicki Wilson Maple Leaf Realty

106 Park St Unit 8, Bennington, VT 05201

/36
Est $751,717 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,104 Sq Ft
469 Laclair Rd, Shaftsbury, VT 05262

469 Laclair Rd, Shaftsbury, VT 05262

/60
$1,600,000
- 5 Beds
- 4.5 Baths
- 4,243 Sq Ft
397 Fern Hill, Dorset, VT 05251

Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 644-3043

397 Fern Hill, Dorset, VT 05251
/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
/3
$452,500 Sold Aug 28, 2025

3460 Sunderland Hill Rd, Arlington, VT 05250
- 3 Beds
- 3 Baths
- 2,935 Sq Ft
- Built 1920
Last Sold Summary
- 14% Below List Price
- $154/SF
- 17 Days On Market
Current Estimated Value $566,804

Last Listing Agent William Mariano

3460 Sunderland Hill Rd, Arlington, VT 05250

/28
Not Listed For Sale
- 6 Beds
- 6.5 Baths
- 5,896 Sq Ft
27 Mountain View Rd, Winhall, VT 05360

27 Mountain View Rd, Winhall, VT 05360

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