Bennington County, VT homes for sale & real estate

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NEW 6 HRS AGO

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft added & Heated Tack Rm, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/ nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete enjoyment. This is a vintage 1800's farmhouse with an old grist mill foundation still evident along the brook that runs through this historic property! Covered Porch & Patio is perfect for relaxing rocking, while being soothed by the soft sounds of the brook. Renovated in 20

$579,900

4 beds3 baths2,529 sq ft

126 Simeon Dean Rd, Shaftsbury, VT 05262

Newly fenced pasture • Paddocks • New electric

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c. 1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized ki

$695,000

3 beds2.5 baths2,715 sq ft

58 Mount Anthony Rd, Bennington, VT 05201

Sprawling views • Formal dining room • Exposed beams

NEW 23 HRS AGO

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Lovely ranch home with 2 bedrooms on a great level lot. Come see all the improvements including but not limited to, new flooring, new kitchen counter, new stove, new dishwasher, fresh paint throughout, new boiler, new oil tank, and new light fixtures. Come see what else this home has to offer.

$185,000

2 beds1 bath880 sq ft

2591 Chapel Rd, Bennington, VT 05201

New stove • New boiler • Fresh paint

ABOUT THIS HOME
Bennington County, VT Homes for Sale
Tucked away from the road and surrounded by nature, this inviting duplex in Bennington offers the perfect blend of privacy, charm, and convenience. Whether you're looking for a smart investment or a place to call home while earning rental income, this property is a must-see! Each spacious unit features 3 comfortable bedrooms, an updated full bath, bright living and dining rooms, and a classic kitchen complete with a nostalgic walk-in pantry, electric range, and refrigerator. Laundry hookups are available for both units — one conveniently located in the pantry upstairs, and the other in the basement, which also provides generous storage space. Enjoy peace of mind with separate utilitie

$239,900

6 beds2 baths2,400 sq ft

110 S Branch St, Bennington, VT 05201

Separate utilities • Updated full bath • Classic kitchen

ABOUT THIS HOME
Bennington County, VT Homes for Sale
A great getaway or starter home tucked away in the Vermont woods. Up on a hill, there are partial mountain views, privacy and a fenced in area for animals and chickens. Close to VAST and VASA trail systems, hiking, hunting, backcountry skiing and lakes. Downhill skiing - multiple areas less than an hour away. Country living not too far from the city! Come check it out.

$175,000

2 beds1 bath792 sq ft

4677 Vt Route 100, Readsboro, VT 05350

Fenced in area • 1.7 acre lot • Built 1950

Property at 4928 Main St #2, Manchester Center, VT 05255, 2 beds, 2 baths

$675,000

2 beds2 baths1,432 sq ft

4928 Main St #2, Manchester Center, VT 05255

Property at 496 County Rd, Stamford, VT 05352, 2 beds, 1 bath

$249,900

2 beds1 bath1,120 sq ft

496 County Rd, Stamford, VT 05352

Property at 32 Cobble Ridge Rd Unit D10, Winhall, VT 05340, 3 beds, 3 baths

$735,000

3 beds3 baths2,317 sq ft

32 Cobble Ridge Rd Unit D10, Winhall, VT 05340

Property at 143 Nichols Rd, Peru, VT 05152, 8 beds, 6 baths

$895,000

8 beds6 baths4,326 sq ft

143 Nichols Rd, Peru, VT 05152

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 115 Nottingham Park, Manchester Center, VT 05255, 3 beds, 2 baths

$629,000

3 beds2 baths2,120 sq ft

115 Nottingham Park, Manchester Center, VT 05255

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 933 E Rd, Bennington, VT 05201, 2 beds, 1 bath

$37,100

2 beds1 bath1,302 sq ft

933 E Rd, Bennington, VT 05201

Property at 9 Lower Taylor Hill Rd, Winhall, VT 05340, 4 beds, 3.5 baths

$1,195,000

4 beds3.5 baths4,200 sq ft

9 Lower Taylor Hill Rd, Winhall, VT 05340

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 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 389 Wilcox Rd, Arlington, VT 05250, 3 beds, 2 baths

$595,000

3 beds2 baths3,475 sq ft

389 Wilcox Rd, Arlington, VT 05250

Property at 50 Grouse Ln, Dorset, VT 05251, 4 beds, 4.5 baths

$1,495,000

4 beds4.5 baths5,170 sq ft

50 Grouse Ln, Dorset, VT 05251

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 134 Monument Ave, Bennington, VT 05201, 3 beds, 2.5 baths

$695,000

3 beds2.5 baths2,868 sq ft

134 Monument Ave, Bennington, VT 05201

Property at 466 Three Maple Dr, Manchester Center, VT 05255, 3 beds, 4.5 baths

$3,350,000

3 beds4.5 baths3,059 sq ft

466 Three Maple Dr, Manchester Center, VT 05255

Property at 508 Barney Rd, Bennington, VT 05201, 3 beds, 1.5 baths

$295,000

3 beds1.5 baths1,934 sq ft

508 Barney Rd, Bennington, VT 05201

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

$169,900

4 beds2 baths1,596 sq ft

4697 Main Rd, Stamford, VT 05352

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

$2,495,000

4 beds5.5 baths4,506 sq ft

3039 Route 30, Dorset, VT 05251

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 6 Chad Cir, Bondville, VT 05340, 5 beds, 4 baths

$1,100,000

5 beds4 baths4,788 sq ft

6 Chad Cir, Bondville, VT 05340

Property at 848 Coleville Rd, Bennington, VT 05201, 4 beds, 3 baths

$450,000

4 beds3 baths2,030 sq ft

848 Coleville Rd, Bennington, VT 05201

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 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 477 Mountain View Dr, Shaftsbury, VT 05262, 3 beds, 2 baths

$490,000

3 beds2 baths2,265 sq ft

477 Mountain View Dr, Shaftsbury, VT 05262

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

$395,000

3 beds2 baths2,661 sq ft

2842 Vermont Route 7A, Shaftsbury, VT 05262

Property at 114 Colebrook Rd, East Arlington, VT 05252, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths2,800 sq ft

114 Colebrook Rd, East Arlington, VT 05252

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 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 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 115 River St, Bennington, VT 05201, 4 beds, 1.5 baths

$74,900

4 beds1.5 baths1,887 sq ft

115 River St, Bennington, VT 05201

Property at 81 Windward Hl, Dorset, VT 05251, 4 beds, 3.5 baths

$950,000

4 beds3.5 baths4,650 sq ft

81 Windward Hl, Dorset, VT 05251

Property at 6 Old Ridge Rd, Bondville, VT 05340, 5 beds, 4.5 baths

$1,100,000

5 beds4.5 baths4,453 sq ft

6 Old Ridge Rd, Bondville, VT 05340

Property at 3746-3738 Main St Unit A, Manchester, VT 05254, 3 beds, 4.5 baths

$1,350,000

3 beds4.5 baths3,415 sq ft

3746-3738 Main St Unit A, Manchester, VT 05254

Property at 317 Pleasant St, Bennington, VT 05201, 5 beds, 2 baths

$215,000

5 beds2 baths2,201 sq ft

317 Pleasant St, Bennington, VT 05201

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Average home prices near Bennington County, VT

Cities

Jamaica homes for sale
$339,000
Wilmington homes for sale
$760,000
Manchester homes for sale
$882,500
Stratton Mountain homes for sale
$972,000
Arlington homes for sale
$368,000
Bennington homes for sale
$282,000
Manchester Center homes for sale
$662,500
Chimney Hill homes for sale
$499,000
Dorset homes for sale
$875,000
North Bennington homes for sale
$350,000

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)

$370,000

-9.76% YoY | Sep 2025

1 year
3 year
5 year

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

Location

Data

Sep 2025

Growth

% YoY

Bennington County, VT

$370,000

-9.76%

See more Bennington County, VT market insights

More to explore in Bennington County, VT

How to buy a house in Bennington County, VT

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First-time homebuyer's guide

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Popular Markets in Vermont

Burlington homes for sale
$589,450
Stowe homes for sale
$1,175,000
Woodstock homes for sale
$1,195,000
Montpelier homes for sale
$429,500
Brattleboro homes for sale
$344,500
South Burlington homes for sale
$607,450
Shelburne homes for sale
$619,950
Waterbury homes for sale
$362,000
Rutland homes for sale
$278,000
Manchester homes for sale
$882,500
Ludlow homes for sale
$564,000
Middlebury homes for sale
$482,500
Barre homes for sale
$280,900
Bennington homes for sale
$282,000
Norwich homes for sale
$639,000

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 Fri Oct 24 2025 on the search page

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