Luxury homes for sale & real estate in Bennington County, VT

48 homes

Sort:

Recommended

NEW 2 HRS AGO

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room. Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef’s kitchen includes custom inset cabinetry, marble countertops, a Sub-Zero refrigerator, Viking range, and a walk-in pantry with walnut counter and beadboard ceiling. The primary suite offers a cathedral ceiling and tranquil views, with a spa-like bath featuring marble floors and a clawfoot soaking tub. Two

$1,425,000

3 beds2.5 baths2,560 sq ft

1058 Granger Hollow Rd, Shaftsbury, VT 05262

Over 40 acres • Mature forest • Stone walls

NEW 4 HRS AGO

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Exceptionally furnished, this residence is a "Stand Out" Ramsey Gourd, architect designed, coveted River Road Colonial accommodating 4,450 SF main level (8,585 SF on three floors) drenched in south facing light tying indoor - outdoor living to ideal mountain view perspectives. The East Mountains create the back drop for the elegantly laid out open concept that seamlessly transitions from area to spacious area. A cook's kitchen suggests separate prep areas, clean up areas, pantry and dining with full brick fireplace wall and always the hearth of the home. The formal BDDW handmade heirloom quality dining and ultra comfortable coffered ceiling living room is balanced upon a wonderful

$2,750,000

4 beds7.5 baths8,586 sq ft

384 Riverbend Dr, Manchester Center, VT 05254

Formal dining • Open concept • Architect designed

NEW 20 HRS AGO

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Endless possibilities !!!!! Inn, Air BNB, Restaurant, Family compound. Building has been updated and lovingly renovated with a few things left to do. great location. Minutes to Bromley. Come and see. Worth the trip

$1,295,000

14 beds13.5 baths6,000 sq ft

2759 rt 11 Rte, Peru, VT 05251

Minutes to bromley • 9.56 acre lot • Built 1825

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Showings to start Saturday, January 3rd. One-of-a-kind, craftsman-built Vermont log home set on over 26 private acres with breathtaking, long-range mountain views. Tucked away at the dead end of the road, this exceptional property offers rare privacy while remaining close to premier ski mountains and all the dining, shopping, and cultural attractions of Manchester, VT. The land features two picturesque waterfalls and a serene natural setting that feels worlds away. The home showcases expansive windows that flood the interior with natural light, highlighting warm wood tones and timeless craftsmanship throughout. Enjoy outdoor living from the inviting covered front porch or the back deck with

$1,399,000

4 beds3.5 baths5,397 sq ft

12 Sunny Hill Rd, Winhall, VT 05340

Vermont log home • 26.9 acre lot • 3 garage spots

ABOUT THIS HOME
Luxury Home for sale in Bennington County, VT:
Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season. Step inside to find a spacious, light-filled interior with clean contemporary lines, warm natural materials, and an inviting open layout ideal for gathering with family and friends. Large windows bring the outdoors in, while generous living spaces provide plenty of room to relax after a day

$950,000

4 beds3.5 baths3,031 sq ft

7 Roundtree Rd, Bondville, VT 05340

Private acres • Large windows • Expansive lot

Property at 124 Elm St, Bennington, VT 05201

$975,000

— beds— baths8,888 sq ft

124 Elm St, Bennington, VT 05201

Property at 11 Founders Hill Rd, Winhall, VT 05340, 5 beds, 3.5 baths

$1,150,000

5 beds3.5 baths4,017 sq ft

11 Founders Hill Rd, Winhall, VT 05340

Property at 24 N Branch Rd, Winhall, VT 05340, 5 beds, 4.5 baths

$995,000

5 beds4.5 baths2,321 sq ft

24 N Branch Rd, Winhall, VT 05340

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 19 Roundtree Rd, Bondville, VT 05340, 4 beds, 2.5 baths

$1,025,000

4 beds2.5 baths3,086 sq ft

19 Roundtree Rd, Bondville, VT 05340

Property at 1594 Vermont Route 7A, Shaftsbury, VT 05262, 5 baths

$995,000

— beds5 baths4,724 sq ft

1594 Vermont Route 7A, Shaftsbury, VT 05262

Property at 146 Ridges Way Unit 1200-1, Peru, VT 05161, 4 beds, 3.5 baths

$850,000

4 beds3.5 baths3,658 sq ft

146 Ridges Way Unit 1200-1, Peru, VT 05161

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 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 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 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 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 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 23 Valley View Rd, Winhall, VT 05340, 3 beds, 3.5 baths

$2,800,000

3 beds3.5 baths3,938 sq ft

23 Valley View Rd, Winhall, VT 05340

Property at 2589 W Sandgate Rd, Arlington, VT 05250, 5 beds, 3 baths

$1,995,000

5 beds3 baths6,323 sq ft

2589 W Sandgate Rd, Arlington, VT 05250

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 759 Stratton Mountain Access Rd #339, Stratton, VT 05155, 3 beds, 3 baths

$995,000

3 beds3 baths1,501 sq ft

759 Stratton Mountain Access Rd #339, Stratton, VT 05155

Property at 24 VT Route 11, Londonderry, VT 05148, 6 beds, 7 baths

$895,000

6 beds7 baths5,764 sq ft

24 VT Route 11, Londonderry, VT 05148

Property at 932 McNamara Rd, Dorset, VT 05251, 4 beds, 3 baths

$1,525,000

4 beds3 baths3,931 sq ft

932 McNamara Rd, Dorset, VT 05251

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 3309 3321 Main St, Manchester, VT 05254, 11 beds, 7.5 baths

$1,300,000

11 beds7.5 baths9,560 sq ft

3309 3321 Main St, Manchester, VT 05254

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

$850,000

4 beds3 baths3,659 sq ft

445 Canterbury Rd, Manchester Center, VT 05255

Property at 17 Roundtree Rd, Bondville, VT 05340, 4 beds, 3.5 baths

$999,000

4 beds3.5 baths2,280 sq ft

17 Roundtree Rd, Bondville, VT 05340

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 636 Dexter Rd, Shaftsbury, VT 05262, 4 beds, 3 baths

$985,000

4 beds3 baths2,462 sq ft

636 Dexter Rd, Shaftsbury, VT 05262

Property at 3888-3904 VT Route 7A, Arlington, VT 05250, 17 beds, 19 baths

$1,745,000

17 beds19 baths14,861 sq ft

3888-3904 VT Route 7A, Arlington, VT 05250

Property at 25 Mountain Haunts Rd, Bondville, VT 05340, 6 beds, 6.5 baths

$2,999,000

6 beds6.5 baths6,650 sq ft

25 Mountain Haunts Rd, Bondville, VT 05340

Property at 1016 West Rd, Manchester, VT 05254, 4 beds, 5 baths

$1,245,000

4 beds5 baths4,272 sq ft

1016 West Rd, Manchester, VT 05254

Property at 1677 Barnumville Rd, Manchester Center, VT 05255, 4 beds, 2.5 baths

$1,350,000

4 beds2.5 baths4,634 sq ft

1677 Barnumville Rd, Manchester Center, VT 05255

Property at 25 Benson Fuller Rd, Winhall, VT 05340, 4 beds, 3.5 baths

$860,000

4 beds3.5 baths4,104 sq ft

25 Benson Fuller Rd, Winhall, VT 05340

Property at 527 Benson Rd, Manchester Center, VT 05255, 5 beds, 4 baths

$4,975,000

5 beds4 baths6,998 sq ft

527 Benson Rd, Manchester Center, VT 05255

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

$1,700,000

4 beds3.5 baths2,363 sq ft

43 Middle Ridge Rd #415, South Londonderry, VT 05155

Property at 2001 Depot St, Manchester, VT 05255, 6 beds, 7 baths

$1,190,000

6 beds7 baths5,400 sq ft

2001 Depot St, Manchester, VT 05255

Property at 515 W Fields Rd, Manchester, VT 05254, 5 beds, 5.5 baths

$6,900,000

5 beds5.5 baths6,500 sq ft

515 W Fields Rd, Manchester, VT 05254

Property at 33 Forest Haunts Rd, Bondville, VT 05340, 4 beds, 4 baths

$1,350,000

4 beds4 baths4,640 sq ft

33 Forest Haunts Rd, Bondville, VT 05340

Property at 14 Old Ridge Rd, Bondville, VT 05340, 4 beds, 4 baths

$1,975,000

4 beds4 baths4,270 sq ft

14 Old Ridge Rd, Bondville, VT 05340

Viewing page 1 of 2

Luxury Homes for Sale in Bennington County

There are currently 48 luxury homes for sale in Bennington County at a median listing price of $550K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Bennington County stay on the market for 86 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 38 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 30 condos, 1 townhouse, and 11 multi-family units for sale in Bennington County last month. Find your dream home in Bennington County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Bennington County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Bennington County. If you're looking to sell your home in the Bennington County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Bennington County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Bennington County, VT

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
$553,450
Stowe homes for sale
$1,124,500
Woodstock homes for sale
$1,095,000
Montpelier homes for sale
$409,500
Brattleboro homes for sale
$375,000
South Burlington homes for sale
$696,580
Shelburne homes for sale
$549,900
Waterbury homes for sale
$399,000
Rutland homes for sale
$277,500
Ludlow homes for sale
$557,500
Manchester homes for sale
$1,300,000
Middlebury homes for sale
$482,500
Barre homes for sale
$269,000
Bennington homes for sale
$259,450
Norwich homes for sale
$0

Copyright 2026 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 Sat Jan 03 2026 on the search page

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

Luxury homes for sale & real estate in Bennington County, VT

Luxury Homes for Sale in Bennington County

More real estate resources for Bennington County, VT

Nearby Counties

Cities

Nearby Counties with Luxury Homes

Nearby Cities with Luxury Homes

More to explore in Bennington County, VT

How to buy a house in Bennington County, VT

Popular Markets in Vermont