Bennington County, VT homes for sale & real estate

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NEW 10 HRS AGO

163 VT Route 30 Rd, Winhall, VT 05340
163 VT Route 30 Rd, Winhall, VT 05340
163 VT Route 30 Rd, Winhall, VT 05340
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Charming Restored Post & Beam Home with Commercial Zoning Near Stratton. Discover the perfect blend of rustic charm and modern functionality in this beautifully restored post and beam home ideally situated at the corner of Vermont Route 30 and scenic Kendall Farm Road. Featuring three bedrooms and two full baths, the home offers soaring vaulted ceilings, exposed beams, and an abundance of natural light that highlights its warm, inviting character. Located less than a mile from the Stratton Mountain access road, this property places you in the heart of Southern Vermonts year-round recreation. Enjoy easy access to skiing, hiking, and biking, with the Stratton snowmaking pond just a shor

$449,000

3 beds2 baths1,590 sq ft

163 VT Route 30 Rd, Winhall, VT 05340

0.93 acre lot • Car-dependent

OPEN SAT, 11AM TO 12:30PM

679 Middle Pownal Rd, Pownal, VT 05261
679 Middle Pownal Rd, Pownal, VT 05261
679 Middle Pownal Rd, Pownal, VT 05261
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Nestled in the heart of rural Pownal, this beautifully renovated 4-bedroom, 3-bath home offers the perfect blend of modern comfort and peaceful countryside living. Set on 12.1 picturesque acres, the property features a mix of open level land and serene wooded areas, ideal for hobby farming, equestrian use, or simply enjoying nature. Inside, you'll find a spacious and thoughtfully designed layout with generous living spaces, a contemporary kitchen featuring quartz countertops, and elegantly updated rooms throughout. The sunny breakfast nook opens via French doors to a large newer deck, perfect for entertaining or relaxing. There's ample room to build a barn, raise animals, or create expansiv

$509,900

4 beds2.5 baths2,240 sq ft

679 Middle Pownal Rd, Pownal, VT 05261

12.1 acre lot • Car-dependent

NEW 16 HRS AGO

8920 Sage Hill Rd #20, Manchester, VT 05255
8920 Sage Hill Rd #20, Manchester, VT 05255
8920 Sage Hill Rd #20, Manchester, VT 05255
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Nestled amidst the breathtaking scenery, this 3 bedroom condominium offers an idyllic escape. Inside, you're greeted by an open living space on the main floor, featuring high ceilings, natural woodwork and a wood-burning fireplace. The kitchen is spacious and flows into the dining/living area. On the main floor you'll also find the primary bedroom, full bathroom, half bath, and enclosed three season porch. Upstairs, two additional good sized bedrooms share a full bathroom, providing comfort and privacy for family and guests. Downstairs you’ll discover a versatile unfinished lower level, complete with dumb waiter, storage space, and closet. The attached two-car garage ensures convenien

$445,000

3 beds2.5 baths1,777 sq ft

8920 Sage Hill Rd #20, Manchester, VT 05255

$800 HOA • 2 garage spots • Community pool

22 Bromley Forest Rd, Winhall, VT 05340
22 Bromley Forest Rd, Winhall, VT 05340
22 Bromley Forest Rd, Winhall, VT 05340
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Open House Sunday July 6, 10-12. Welcome to your dream Vermont home—where space, light, and location come together in perfect harmony. This beautifully upgraded 4-bedroom residence, complete with a versatile bonus room, features an open-concept living area designed for comfort and connection. The kitchen is a standout, featuring an ILVE 30-Inch Majestic II Dual Fuel Range with 5 Sealed Brass Burners—offering a professional-grade cooking experience in the heart of your home. Expansive windows throughout flood the home with natural light, creating a warm and inviting atmosphere. Step outside onto the deck and take in breathtaking mountain views—perfect for relaxing or enter

$705,000

4 beds2.5 baths2,408 sq ft

22 Bromley Forest Rd, Winhall, VT 05340

1 acre lot • Garage • Car-dependent

C1 Meadow Ridge Rd, Winhall, VT 05340
C1 Meadow Ridge Rd, Winhall, VT 05340
C1 Meadow Ridge Rd, Winhall, VT 05340
ABOUT THIS HOME
Bennington County, VT Homes for Sale
WELCOME TO YOUR FAMILY'S PERFECT MOUNTAIN RETREAT. .WELCOME TO PIPER RIDGE!! This spacious 4 bedroom/4 bath condo is designed for comfort, convenience and offers an exceptional blend of mountain charm and modern amenities! Enjoy two open concept living areas with cozy wood burning fireplaces, fully equipped kitchen, private balcony showcasing winter mountain views. .. Perfect for entertaining. .. With timeless and delightful charm it is the ideal haven for family and guests! The "Icing on the Cake" and Real GEM is the exclusive access to your own state of the art sports center featuring a fitness center, indoor heated pool, tennis, game room and much more, great for unwinding afte

$885,000

4 beds4 baths2,598 sq ft

C1 Meadow Ridge Rd, Winhall, VT 05340

$1,507 HOA • Garage • Community pool

Property at 42 Colvin Ave, Shaftsbury, VT 05262, 3 beds, 1 bath

$199,900

3 beds1 bath952 sq ft

42 Colvin Ave, Shaftsbury, VT 05262

Property at 0 Maple Ridge Rd Unit B-2, Winhall, VT 05340, 4 beds, 3 baths

$820,000

4 beds3 baths2,317 sq ft

0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

Property at 78 Farm Rd Unit C1, Peru, VT 05152, 3 beds, 2 baths

$359,000

3 beds2 baths1,102 sq ft

78 Farm Rd Unit C1, Peru, VT 05152

Property at 272 Oak Hill Rd, Shaftsbury, VT 05262, 3 beds, 2.5 baths

$699,000

3 beds2.5 baths3,637 sq ft

272 Oak Hill Rd, Shaftsbury, VT 05262

Property at 6311 VT Route 7A, Sunderland, VT 05250, 10 beds, 6 baths

$795,000

10 beds6 baths5,493 sq ft

6311 VT Route 7A, Sunderland, VT 05250

Property at 7 Timberbrook N, Dorset, VT 05251, 5 beds, 4.5 baths

$1,550,000

5 beds4.5 baths4,219 sq ft

7 Timberbrook N, Dorset, VT 05251

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

$1,350,000

3 beds4.5 baths2,200 sq ft

3746-3738 Main St, Manchester, VT 05254

Property at 397 Fern Hl, Dorset, VT 05251, 5 beds, 4.5 baths

$1,600,000

5 beds4.5 baths4,243 sq ft

397 Fern Hl, Dorset, VT 05251

Property at E12 Rock Ridge Rd, Winhall, VT 05340, 3 beds, 3 baths

$795,000

3 beds3 baths1,842 sq ft

E12 Rock Ridge Rd, Winhall, VT 05340

Property at 725 Wideawake Rd, Manchester, VT 05255, 3 beds, 3 baths

$949,000

3 beds3 baths3,037 sq ft

725 Wideawake Rd, Manchester, VT 05255

Property at 2588 Vermont Route 11, Peru, VT 05152, 4 beds, 3 baths

$565,000

4 beds3 baths2,073 sq ft

2588 Vermont Route 11, Peru, VT 05152

Property at 3530 VT Route 346, Pownal, VT 05261, 3 beds, 2.5 baths

$299,900

3 beds2.5 baths1,810 sq ft

3530 VT Route 346, Pownal, VT 05261

Property at 55 Uphill Rd, Landgrove, VT 05148, 3 beds, 2.5 baths

$750,000

3 beds2.5 baths2,716 sq ft

55 Uphill Rd, Landgrove, VT 05148

Property at 379 Owl's Head Hl, Dorset, VT 05251, 3 beds, 4 baths

$775,000

3 beds4 baths2,187 sq ft

379 Owl's Head Hl, Dorset, VT 05251

Property at D-9 Cobble Ridge Rd, Winhall, VT 05340, 3 beds, 3 baths

$799,000

3 beds3 baths2,317 sq ft

D-9 Cobble Ridge Rd, Winhall, VT 05340

Property at 60 Knoll Crest Ln, Bennington, VT 05201, 4 beds, 2 baths

$355,000

4 beds2 baths2,072 sq ft

60 Knoll Crest Ln, Bennington, VT 05201

Property at 120 Albe Dr, Bennington, VT 05201, 3 beds, 2.5 baths

$319,000

3 beds2.5 baths1,888 sq ft

120 Albe Dr, Bennington, VT 05201

Property at 14 Robinson Ave, Bennington, VT 05201, 3 beds, 1 bath

$219,500

3 beds1 bath1,254 sq ft

14 Robinson Ave, Bennington, VT 05201

Property at 303-305 Gage St, Bennington, VT 05201, 6 beds, 2 baths

$225,000

6 beds2 baths2,112 sq ft

303-305 Gage St, Bennington, VT 05201

Property at 318 Skyboro Rd W, Pownal, VT 05261, 3 beds, 1 bath

$119,000

3 beds1 bath1,008 sq ft

318 Skyboro Rd W, Pownal, VT 05261

Property at 174 Cleveland Ave, Shaftsbury, VT 05262, 3 beds, 1 bath

$249,000

3 beds1 bath1,660 sq ft

174 Cleveland Ave, Shaftsbury, VT 05262

Property at 145 White Farm Ln, Shaftsbury, VT 05262, 4 beds, 4 baths

$920,000

4 beds4 baths3,974 sq ft

145 White Farm Ln, Shaftsbury, VT 05262

Property at 106 Eagle Nest Rd #12, Manchester, VT 05255, 3 beds, 2.5 baths

$595,000

3 beds2.5 baths2,220 sq ft

106 Eagle Nest Rd #12, Manchester, VT 05255

Property at 2374 Shaftsbury Hollow Rd, Shaftsbury, VT 05257, 2 beds, 1 bath

$395,000

2 beds1 bath1,624 sq ft

2374 Shaftsbury Hollow Rd, Shaftsbury, VT 05257

Property at 18 Jameson Flats Rd #18, Manchester, VT 05255, 2 beds, 1.5 baths

$649,500

2 beds1.5 baths1,293 sq ft

18 Jameson Flats Rd #18, Manchester, VT 05255

Property at 3357 Main St, Manchester, VT 05254, 4 beds, 3 baths

$849,000

4 beds3 baths3,609 sq ft

3357 Main St, Manchester, VT 05254

Property at 242 North Rd, Sunderland, VT 05252, 2 beds, 1.5 baths

$135,000

2 beds1.5 baths1,056 sq ft

242 North Rd, Sunderland, VT 05252

Property at 3460 Sunderland hill Rd, Sunderland, VT 05250, 3 beds, 3 baths

$525,000

3 beds3 baths2,935 sq ft

3460 Sunderland hill Rd, Sunderland, VT 05250

Property at 395 King Hill Rd, Readsboro, VT 05350, 5 beds, 1 bath

$1,200,000

5 beds1 bath2,228 sq ft

395 King Hill Rd, Readsboro, VT 05350

Property at 21 Burnt Hill Rd, Winhall, VT 05340, 4 beds, 2 baths

$749,000

4 beds2 baths2,055 sq ft

21 Burnt Hill Rd, Winhall, VT 05340

Property at 3 Strattonwald Rd, Winhall, VT 05340, 3 beds, 1 bath

$525,000

3 beds1 bath1,344 sq ft

3 Strattonwald Rd, Winhall, VT 05340

Property at 636 Dexter Rd, Shaftsbury, VT 05262, 3 beds, 3 baths

$1,150,000

3 beds3 baths2,462 sq ft

636 Dexter Rd, Shaftsbury, VT 05262

Property at 215 Dewey St, Bennington, VT 05201, 6 beds, 2 baths

$239,900

6 beds2 baths2,288 sq ft

215 Dewey St, Bennington, VT 05201

Property at 445 Canterbury Rd, Manchester, VT 05255, 4 beds, 3 baths

$995,000

4 beds3 baths3,659 sq ft

445 Canterbury Rd, Manchester, VT 05255

Property at 19 Royal St, Bennington, VT 05257, 4 beds, 1 bath

$365,000

4 beds1 bath1,680 sq ft

19 Royal St, Bennington, VT 05257

Property at 137-139 Park St, Bennington, VT 05201, 5 beds, 3 baths

$249,000

5 beds3 baths2,184 sq ft

137-139 Park St, Bennington, VT 05201

Viewing page 1 of 6

Average home prices near Bennington County, VT

Cities

Wilmington homes for sale
$587,500
Manchester homes for sale
$1,195,000
Stratton Mountain homes for sale
$850,000
Arlington homes for sale
$599,000
Bennington homes for sale
$284,000
Manchester Center homes for sale
$649,250
Chimney Hill homes for sale
$425,000
Dorset homes for sale
$1,582,500
North Bennington homes for sale
$496,950

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)

$401,000

-32.4% YoY | May 2025

1 year
3 year
5 year

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

Location

Data

May 2025

Growth

% YoY

Bennington County, VT

$401,000

-32.4%

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?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Vermont

Burlington homes for sale
$626,795
Stowe homes for sale
$1,099,500
Woodstock homes for sale
$1,150,000
Montpelier homes for sale
$477,200
Brattleboro homes for sale
$347,000
South Burlington homes for sale
$685,000
Shelburne homes for sale
$745,000
Waterbury homes for sale
$339,500
Manchester homes for sale
$1,195,000
Rutland homes for sale
$296,450
Ludlow homes for sale
$567,000
Bennington homes for sale
$284,000
Barre homes for sale
$259,950
Middlebury homes for sale
$519,500
Norwich homes for sale
$1,095,000

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 Tue Jul 08 2025 on the search page

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