Bennington County, VT homes for sale & real estate

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NEW 7 HRS AGO

86 Benson Fuller Dr, Winhall, VT 05340
86 Benson Fuller Dr, Winhall, VT 05340
86 Benson Fuller Dr, Winhall, VT 05340
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Your Ultimate Family Getaway Escape to this idyllic Vermont retreat, where convenience meets relaxation. This spacious home offers everything you need for a fun-filled and carefree lifestyle, from outdoor entertaining to cozy indoor spaces. Step out onto the large deck and unwind by the gas fire pit table, or enjoy watching the friendly mini-golf matches below. In the cooler nights of winter, take in the mountain views. As you enter inside you'll find the perfect place to hang your coat and drop your shoes. The open kitchen is perfect for entertaining both inside and out. This house boasts of two inviting living rooms, each featuring a wood stove for warmth and ambiance—ideal for thos

$749,000

4 beds2 baths2,040 sq ft

86 Benson Fuller Dr, Winhall, VT 05340

1 acre lot • Car-dependent

NEW 19 HRS AGO

72 Two Cow Ln, Manchester, VT 05255
72 Two Cow Ln, Manchester, VT 05255
72 Two Cow Ln, Manchester, VT 05255
ABOUT THIS HOME
Bennington County, VT Homes for Sale
CREAM ALWAYS RISES TO THE TOP!. .. .. Especially on Two Cow Lane!! Step in to this charming GEM and discover for yourself timeless elegance with this beautifully crafted 3 bedroom 2 bath home built by Breen Builders, known for impeccable detail and quality. .. .Obvious from the precision of each cut to the flawless finishes that highlight the natural beauty of the wood throughout this warm inviting home filled with natural light! The kitchen boast handcrafted cabinetry and modern amenities, perfect for family gatherings. Relax in the cozy living room, rich pine floors and a Sir Rumford style fireplace for cooler evenings! Set in a picturesque neighborhood, enjoy effortless access to both Ma

$619,000

3 beds2 baths1,987 sq ft

72 Two Cow Ln, Manchester, VT 05255

0.32 acre lot • Somewhat walkable

NEW 20 HRS AGO

432 South St Unit C6, Bennington, VT 05201
432 South St Unit C6, Bennington, VT 05201
432 South St Unit C6, Bennington, VT 05201
ABOUT THIS HOME
Bennington County, VT Homes for Sale
A fresh perspective on easy living! Welcome to this beautifully maintained 2BR/1.5 BA second-floor condo in Nathanial Court offering the perfect blend of comfort, convenience, and low-maintenance living. Step into a bright and airy open floor plan, where large windows flood the space with natural light. The tidy kitchen boasts ample cabinet space, sleek stainless steel appliances, and a clean aesthetic. Retreat to the spacious primary bedroom, complete with a generous walk-in closet to keep everything organized and clutter-free. Whether you're looking for a full-time residence or a charming second home, this condo fits the bill. Enjoy being just minutes from downtown shops and restaurants,

$155,000

2 beds1.5 baths852 sq ft

432 South St Unit C6, Bennington, VT 05201

$211 HOA • Somewhat walkable

266 Robillard Rd, Stamford, VT 05352
266 Robillard Rd, Stamford, VT 05352
266 Robillard Rd, Stamford, VT 05352

$225,000

6 beds1.5 baths2,082 sq ft

266 Robillard Rd, Stamford, VT 05352

0.64 acre lot • Car-dependent

62 Dorset Village Ln, Dorset, VT 05251
62 Dorset Village Ln, Dorset, VT 05251
62 Dorset Village Ln, Dorset, VT 05251
ABOUT THIS HOME
Bennington County, VT Homes for Sale
Charming Home in Quaint Dorset Village Setting Nestled on a gentle knoll above the heart of Dorset Village, this delightful home offers the perfect blend of privacy and convenience. Just a short stroll to village amenities and mere moments from the renowned Pinnacle hiking trails, the location is ideal for those seeking both community charm and outdoor adventure. Brimming with potential, this village gem invites its next owner to restore it to its original single-family glory or continue its current flexible layout—live comfortably on one level while generating income from the other. The possibilities are endless. Despite its central location, the home enjoys a peaceful, tucked-away f

$595,000

4 beds2 baths2,139 sq ft

62 Dorset Village Ln, Dorset, VT 05251

0.65 acre lot • 3 garage spots • Car-dependent

Property at 115 Benson Fuller Dr, Winhall, VT 05340, 5 beds, 4.5 baths

$2,400,000

5 beds4.5 baths3,252 sq ft

115 Benson Fuller Dr, Winhall, VT 05340

Property at 5515 Main St, Manchester, VT 05255, 2 beds, 2 baths

$645,000

2 beds2 baths4,044 sq ft

5515 Main St, Manchester, VT 05255

Property at 432 South St Unit A7, Bennington, VT 05201, 2 beds, 1.5 baths

$158,000

2 beds1.5 baths819 sq ft

432 South St Unit A7, Bennington, VT 05201

Property at 77 Monument Ave, Bennington, VT 05201, 4 beds, 3.5 baths

$775,000

4 beds3.5 baths4,032 sq ft

77 Monument Ave, Bennington, VT 05201

Property at 43 Middle Ridge Rd #415, Stratton, VT 05155, 4 beds, 3.5 baths

$1,700,000

4 beds3.5 baths2,363 sq ft

43 Middle Ridge Rd #415, Stratton, VT 05155

Property at 190 VT Route 11 #1, Peru, VT 05152, 3 beds, 2 baths

$625,000

3 beds2 baths1,894 sq ft

190 VT Route 11 #1, Peru, VT 05152

Property at 393 Morse Hill Rd, Dorset, VT 05253, 3 beds, 2 baths

$475,000

3 beds2 baths1,460 sq ft

393 Morse Hill Rd, Dorset, VT 05253

Property at 551 W Fields Rd, Manchester, VT 05254, 6 beds, 8 baths

$10,300,000

6 beds8 baths10,993 sq ft

551 W Fields Rd, Manchester, VT 05254

Property at 23 Robinson Ave, Bennington, VT 05201, 3 beds, 1.5 baths

$335,000

3 beds1.5 baths1,682 sq ft

23 Robinson Ave, Bennington, VT 05201

Property at 6 Dwyers Camp Rd, Shaftsbury, VT 05262, 3 beds, 2 baths

$498,000

3 beds2 baths1,671 sq ft

6 Dwyers Camp Rd, Shaftsbury, VT 05262

Property at 36 Beaver St, Winhall, VT 05340, 3 beds, 4 baths

$1,825,000

3 beds4 baths2,872 sq ft

36 Beaver St, Winhall, VT 05340

Property at 755 Main St, Bennington, VT 05201, 3 beds, 1.5 baths

$145,000

3 beds1.5 baths1,485 sq ft

755 Main St, Bennington, VT 05201

Property at 2 Cold Spring Rd, Shaftsbury, VT 05257, 5 beds, 2 baths

$895,000

5 beds2 baths2,424 sq ft

2 Cold Spring Rd, Shaftsbury, VT 05257

Property at 106 Mill Brook Rd, Sunderland, VT 05250, 2 beds, 2 baths

$395,000

2 beds2 baths2,248 sq ft

106 Mill Brook Rd, Sunderland, VT 05250

Property at 1243 Murray Hill Heights Rd #43, Manchester, VT 05255, 3 beds, 3 baths

$475,000

3 beds3 baths1,710 sq ft

1243 Murray Hill Heights Rd #43, Manchester, VT 05255

Property at 224 Burrington Rd, Pownal, VT 05261, 3 beds, 2 baths

$349,900

3 beds2 baths1,658 sq ft

224 Burrington Rd, Pownal, VT 05261

Property at 447 Farm Rd, Arlington, VT 05250, 2 beds, 2 baths

$399,500

2 beds2 baths1,564 sq ft

447 Farm Rd, Arlington, VT 05250

Property at 639 Wiley Mountain Rd, Readsboro, VT 05350, 4 beds, 1.5 baths

$439,000

4 beds1.5 baths1,728 sq ft

639 Wiley Mountain Rd, Readsboro, VT 05350

Property at 495 Fairview St, Bennington, VT 05201, 3 beds, 2 baths

$410,000

3 beds2 baths1,309 sq ft

495 Fairview St, Bennington, VT 05201

Property at 16 Hunters Rdg, Winhall, VT 05340, 4 beds, 4.5 baths

$2,225,000

4 beds4.5 baths5,000 sq ft

16 Hunters Rdg, Winhall, VT 05340

Property at 5 Linscott Rd #56, Winhall, VT 05340, 3 beds, 2.5 baths

$799,000

3 beds2.5 baths2,370 sq ft

5 Linscott Rd #56, Winhall, VT 05340

Property at 5491 VT Route 315, Rupert, VT 05776, 5 beds, 4.5 baths

$2,095,000

5 beds4.5 baths3,218 sq ft

5491 VT Route 315, Rupert, VT 05776

Property at 473 South Rd, Sunderland, VT 05252, 2 beds, 1 bath

$270,000

2 beds1 bath1,136 sq ft

473 South Rd, Sunderland, VT 05252

Property at 681 Powderhorn Rd, Manchester, VT 05255, 4 beds, 3.5 baths

$949,000

4 beds3.5 baths3,400 sq ft

681 Powderhorn Rd, Manchester, VT 05255

Property at 1949 South Rd, Peru, VT 05152, 4 beds, 3 baths

$1,790,000

4 beds3 baths2,545 sq ft

1949 South Rd, Peru, VT 05152

Property at 41 Audrey Ln, Bennington, VT 05201, 2 beds, 2 baths

$96,906

2 beds2 baths777 sq ft

41 Audrey Ln, Bennington, VT 05201

Property at 10 Cassie Ln, Bennington, VT 05201-0000, 2 beds, 2 baths

$96,906

2 beds2 baths777 sq ft

10 Cassie Ln, Bennington, VT 05201-0000

Property at 29 Dustin Dr, Bennington, VT 05201, 2 beds, 2 baths

$96,906

2 beds2 baths777 sq ft

29 Dustin Dr, Bennington, VT 05201

Property at 24 Cassie Ln, Bennington, VT 05201, 2 beds, 2 baths

$96,906

2 beds2 baths777 sq ft

24 Cassie Ln, Bennington, VT 05201

Property at 1268 Myers Rd, Shaftsbury, VT 05262, 4 beds, 3.5 baths

$1,950,000

4 beds3.5 baths4,023 sq ft

1268 Myers Rd, Shaftsbury, VT 05262

Property at 198 Church St, Dorset, VT 05251, 4 beds, 3.5 baths

$3,600,000

4 beds3.5 baths2,338 sq ft

198 Church St, Dorset, VT 05251

Property at 1061 Granger Hollow Rd, Shaftsbury, VT 05257, 3 beds, 2 baths

$499,900

3 beds2 baths2,108 sq ft

1061 Granger Hollow Rd, Shaftsbury, VT 05257

Property at 679 Middle Pownal Rd, Pownal, VT 05261, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths2,240 sq ft

679 Middle Pownal Rd, Pownal, VT 05261

Property at 8920 Sage Hill Rd #20, Manchester, VT 05255, 3 beds, 2.5 baths

$445,000

3 beds2.5 baths1,777 sq ft

8920 Sage Hill Rd #20, Manchester, VT 05255

Property at 22 Bromley Forest Rd, Winhall, VT 05340, 4 beds, 2.5 baths

$675,000

4 beds2.5 baths2,408 sq ft

22 Bromley Forest Rd, Winhall, VT 05340

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

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Average home prices near Bennington County, VT

Cities

Wilmington homes for sale
$587,500
Manchester homes for sale
$1,300,000
Stratton Mountain homes for sale
$845,000
Arlington homes for sale
$549,000
Bennington homes for sale
$275,000
Manchester Center homes for sale
$672,000
Chimney Hill homes for sale
$499,000
Dorset homes for sale
$1,537,500
North Bennington homes for sale
$395,000

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)

$345,000

-1.4% YoY | Jun 2025

1 year
3 year
5 year

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

Location

Data

Jun 2025

Growth

% YoY

Bennington County, VT

$345,000

-1.4%

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
$622,000
Stowe homes for sale
$899,000
Woodstock homes for sale
$995,000
Montpelier homes for sale
$466,950
Brattleboro homes for sale
$329,000
South Burlington homes for sale
$712,500
Shelburne homes for sale
$672,000
Waterbury homes for sale
$345,000
Manchester homes for sale
$1,300,000
Rutland homes for sale
$279,000
Ludlow homes for sale
$512,000
Bennington homes for sale
$272,000
Barre homes for sale
$275,000
Middlebury homes for sale
$634,500
Norwich homes for sale
$1,027,000

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 Jul 25 2025 on the search page

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