Bennington County, VT homes for sale & real estate

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ABOUT THIS HOME
Bennington County, VT Homes for Sale
Centrally located renovated Bennington duplex, with backyard and garage. This duplex can generate an annual net operating income of ~$23k+ at current numbers (~10.5%), producing robust returns from cash flow and not speculation! Owner performed renovations since acquiring, including to heating systems, plumbing, and gut renovation of the upstairs 2br (currently rented for $1,400). Unit 1 on the ground floor is spacious 3br ~1,250 square feet with backyard access, eat in kitchen, desirable layout, and would make a perfect owners' unit if the intention is to owner occupy and cover your mortgage and make extra income (current rent is $1,709 and tenant is on a month-to-month lease). his is a

$215,000

5 beds2 baths2,201 sq ft

317 Pleasant St, Bennington, VT 05201

Heating systems • Plumbing • Gut renovation

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the home and an easy car drive to the Stratton Mountain Village. The home boasts four sizable bedrooms, three and half bathrooms, beautiful stone wood burning fireplace, downstairs family room for games and entertaining, ample storage space as well as finished space above the garage. Wake up to the sun

$1,195,000

4 beds3.5 baths4,200 sq ft

9 Lower Taylor Hill Rd, Winhall, VT 05340

Private acres • Winhall river • Mountain views

ABOUT THIS HOME
Bennington County, VT Homes for Sale
WOW CHECK OUT THIS Country Cutie on the edge of town. The home has been updated while keeping the period Charm. Large level nicely landscaped yard enclosed by hedges. The lager living room has a fireplace with insert and lots of built-ins. The walkout basement has a large room that has been used as a bedroom with a stone fireplace and a half bath in the heated workshop area. The septic was just serviced.

$294,500

3 beds1.5 baths1,934 sq ft

508 Barney Rd, Bennington, VT 05201

Walkout basement • Landscaped yard • Heated workshop area

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Welcome to Three Maple Drive, a beautifully crafted, brand-new single-family home nestled in a quiet and scenic location in Manchester, Vermont. Built in 2023 with impeccable attention to detail, this 3,059 sq ft modern farmhouse seamlessly blends luxury, comfort, and timeless design—all set on a private 3.85-acre lot with gorgeous mountain views. This home features three spacious bedroom suites, each with its own private bath, along with an additional half bath on the main level and a ¾ bath in the expansive bonus room above the garage—perfect for a guest suite, office, or studio. The heart of the home is an open-concept kitchen, dining, and living area filled with natur

$3,350,000

3 beds4.5 baths3,059 sq ft

466 Three Maple Dr, Manchester Center, VT 05255

Private lot • High-end tile work • Open-concept kitchen

ABOUT THIS HOME
Bennington County, VT Homes for Sale
The House that Love Built-Multigenerational Comfort & Thoughtful Design Tucked away in a peaceful neighborhood, set back from a well maintained town road. This beautifully maintained home is perfect for wildlife watching and enjoying serene solitude. Designed with multigenerational or accessible living in mind, the home features a private in-law suite with it's own ramp entry, wide doorways, and a custom roll in shower. Just outside the suite, enjoy a private deck offering easy access and a peaceful place to relax. The main level includes custom woodwork, hardwood floors, passive solar windows, and fresh paint throughout. The cozy kitchen has a window over the porcelain sink, a pantry

$450,000

4 beds3 baths2,030 sq ft

848 Coleville Rd, Bennington, VT 05201

Private deck • Private in-law suite • 3 year old roof

Property at 158 Upland Downs Rd, Manchester Center, VT 05255, 3 beds, 2 baths

$815,000

3 beds2 baths1,743 sq ft

158 Upland Downs Rd, Manchester Center, VT 05255

Property at 2677 Rte 30 Rd, Dorset, VT 05251, 6 beds, 5 baths

$875,000

6 beds5 baths5,689 sq ft

2677 Rte 30 Rd, Dorset, VT 05251

Property at 3039 Route 30, Dorset, VT 05251, 4 beds, 5.5 baths

$2,295,000

4 beds5.5 baths4,506 sq ft

3039 Route 30, Dorset, VT 05251

Property at 126 Washington Ave, Bennington, VT 05201, 6 beds, 3 baths

$415,000

6 beds3 baths5,208 sq ft

126 Washington Ave, Bennington, VT 05201

Property at 144 Taconic Ave, Manchester, VT 05254, 6 beds, 5.5 baths

$1,895,000

6 beds5.5 baths5,178 sq ft

144 Taconic Ave, Manchester, VT 05254

Property at 4697 Main Rd, Stamford, VT 05352, 4 beds, 2 baths

$159,900

4 beds2 baths1,596 sq ft

4697 Main Rd, Stamford, VT 05352

Property at 58 Hicks Ln, Manchester Center, VT 05255, 4 beds, 3 baths

$650,000

4 beds3 baths2,975 sq ft

58 Hicks Ln, Manchester Center, VT 05255

Property at 21 County Rd, Pownal, VT 05261, 4 beds, 2 baths

$450,000

4 beds2 baths2,884 sq ft

21 County Rd, Pownal, VT 05261

Property at 215 & 221 VT Route 30, Dorset, VT 05251, 6 beds, 3 baths

$2,300,000

6 beds3 baths3,340 sq ft

215 & 221 VT Route 30, Dorset, VT 05251

Property at 933 East Rd, Bennington, VT 05201, 2 beds, 1 bath

$35,300

2 beds1 bath1,302 sq ft

933 East Rd, Bennington, VT 05201

Property at 2842 Vermont Route 7A, Shaftsbury, VT 05262, 3 beds, 2 baths

$375,000

3 beds2 baths2,661 sq ft

2842 Vermont Route 7A, Shaftsbury, VT 05262

Property at 130 Ipan Rd, Shaftsbury, VT 05257, 3 beds, 2.5 baths

$795,000

3 beds2.5 baths2,696 sq ft

130 Ipan Rd, Shaftsbury, VT 05257

Property at 89 Merson St, Bennington, VT 05201, 3 beds, 1.5 baths

$339,000

3 beds1.5 baths1,829 sq ft

89 Merson St, Bennington, VT 05201

Property at 1182 1184 East Manchester Rd, Manchester Center, VT 05255, 9 beds, 8.5 baths

$5,250,000

9 beds8.5 baths7,900 sq ft

1182 1184 East Manchester Rd, Manchester Center, VT 05255

Property at 68 Green Peak Orchard Rd S, East Dorset, VT 05253, 5 beds, 5 baths

$3,285,000

5 beds5 baths6,900 sq ft

68 Green Peak Orchard Rd S, East Dorset, VT 05253

Property at 935 Old Manchester Rd, Peru, VT 05152, 2 beds, 1 bath

$495,000

2 beds1 bath1,344 sq ft

935 Old Manchester Rd, Peru, VT 05152

Property at 989 Carpenter Hill Rd, Pownal, VT 05261, 3 beds, 1 bath

$365,000

3 beds1 bath1,660 sq ft

989 Carpenter Hill Rd, Pownal, VT 05261

Property at 557 Beech St, Manchester Center, VT 05255, 3 beds, 1 bath

$319,000

3 beds1 bath836 sq ft

557 Beech St, Manchester Center, VT 05255

Property at 190-194 Cemetery Rd, Arlington, VT 05250, 7 beds, 4 baths

$495,000

7 beds4 baths2,494 sq ft

190-194 Cemetery Rd, Arlington, VT 05250

Property at 27 Owls Head Hill Ln, Dorset, VT 05251, 3 beds, 2 baths

$649,000

3 beds2 baths1,344 sq ft

27 Owls Head Hill Ln, Dorset, VT 05251

Property at 1555 E Arlington Rd, Arlington, VT 05250, 5 beds, 3 baths

$465,000

5 beds3 baths2,622 sq ft

1555 E Arlington Rd, Arlington, VT 05250

Property at 288 Cedar Ln, Peru, VT 05152, 9 beds, 7 baths

$2,300,000

9 beds7 baths5,512 sq ft

288 Cedar Ln, Peru, VT 05152

Property at 51 Russell St Unit D, Arlington, VT 05250, 2 beds, 1.5 baths

$289,000

2 beds1.5 baths1,417 sq ft

51 Russell St Unit D, Arlington, VT 05250

Property at 624 Main St, Bennington, VT 05201, 2 beds, 1 bath

$269,000

2 beds1 bath2,500 sq ft

624 Main St, Bennington, VT 05201

Property at 17 Signal Hill Rd, Bondville, VT 05340, 5 beds, 3.5 baths

$599,000

5 beds3.5 baths2,468 sq ft

17 Signal Hill Rd, Bondville, VT 05340

Property at 704 Fox Hill Rd, Bennington, VT 05201, 3 beds, 2 baths

$575,000

3 beds2 baths1,535 sq ft

704 Fox Hill Rd, Bennington, VT 05201

Property at 682 Fox Hill Rd, Bennington, VT 05201, 3 beds, 2 baths

$625,000

3 beds2 baths1,416 sq ft

682 Fox Hill Rd, Bennington, VT 05201

Property at 143 Stratton Mountain Access Rd, Winhall, VT 05340, 5 beds, 4.5 baths

$1,695,000

5 beds4.5 baths3,688 sq ft

143 Stratton Mountain Access Rd, Winhall, VT 05340

Property at 203-205 Northside Dr, Bennington, VT 05201, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths1,248 sq ft

203-205 Northside Dr, Bennington, VT 05201

Property at 1439 Main St, Manchester Center, VT 05255, 2 beds, 2 baths

$550,000

2 beds2 baths2,218 sq ft

1439 Main St, Manchester Center, VT 05255

Property at 550 Finbars Forest Rd, Manchester Center, VT 05255, 3 beds, 2 baths

$649,000

3 beds2 baths1,958 sq ft

550 Finbars Forest Rd, Manchester Center, VT 05255

Property at 3264 Route 153, West Rupert, VT 05776, 2 beds, 1 bath

$269,000

2 beds1 bath1,400 sq ft

3264 Route 153, West Rupert, VT 05776

Property at 215 Maple St, Bennington, VT 05201, 4 beds, 2 baths

$194,900

4 beds2 baths1,278 sq ft

215 Maple St, Bennington, VT 05201

Property at 3 Kimball Hill Rd #1, Winhall, VT 05340, 3 beds, 2 baths

$375,000

3 beds2 baths1,344 sq ft

3 Kimball Hill Rd #1, Winhall, VT 05340

Property at 139 Prospect St, Manchester, VT 05254, 3 beds, 2.5 baths

$1,849,000

3 beds2.5 baths3,450 sq ft

139 Prospect St, Manchester, VT 05254

Property at 1138 Main Rd, Stamford, VT 05352, 5 beds, 2 baths

$224,500

5 beds2 baths2,212 sq ft

1138 Main Rd, Stamford, VT 05352

Viewing page 2 of 6

Average home prices near Bennington County, VT

Cities

Jamaica homes for sale
$637,000
Wilmington homes for sale
$737,000
Manchester homes for sale
$1,269,000
Stratton Mountain homes for sale
$1,012,000
Arlington homes for sale
$368,000
Bennington homes for sale
$272,000
Manchester Center homes for sale
$687,000
Chimney Hill homes for sale
$499,000
Dorset homes for sale
$875,000
North Bennington homes for sale
$340,000

Counties

Bennington County, VT real estate trends

All Home Types trends in Bennington County, VT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$405,500

-28.6% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Bennington County, VT

$405,500

-28.6%

See more Bennington County, VT market insights

More to explore in Bennington County, VT

How to buy a house in Bennington County, VT

How much house can I afford?

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First-time homebuyer's guide

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Popular Markets in Vermont

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Montpelier homes for sale
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South Burlington homes for sale
$666,130
Shelburne homes for sale
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Waterbury homes for sale
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Rutland homes for sale
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Manchester homes for sale
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Ludlow homes for sale
$585,000
Barre homes for sale
$279,000
Middlebury homes for sale
$482,500
Bennington homes for sale
$272,000
Norwich homes for sale
$0

Copyright 2025 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Wed Dec 10 2025 on the search page

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