Pending Listings in Bennington County, VT

89 homes

Sort:

Recommended

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
A charming in-town home nestled on a generous . 32-acre lot in the heart of Manchester, Vermont. This cozy 2-bedroom, 1-bath single-family home offers the perfect blend of small-town charm and everyday convenience. With 768 square feet of comfortable living space, it's ideal for first-time buyers, downsizers, or those seeking a weekend getaway, or investment in one of Vermont’s most desirable communities. Located in a walkable neighborhood, you're just steps from local grocery stores, restaurants, outlet shopping, schools, parks, and more—everything you need is right at your fingertips. Inside, enjoy a warm and inviting atmosphere with baseboard heat and a toasty wood stove, per

$330,000

2 beds1 bath769 sq ft

64 Bond St, Manchester Center, VT 05255

0.32 acre lot • Somewhat walkable

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
This updated taconic style unit offers room to spread out with formal living room with wood burning fireplace, dining room, and galley style kitchen, three bedrooms, a cozy den complete with wet bar and sliding glass doors to a second deck, and a lower level rec room perfect for recreation or overflow guests. Recent kitchen upgrades include: wood panel cabinets, granite countertops, gas range, stainless appliances, and tile flooring. This unit is located in the very desirable F-units, built in 1985 with a total of 2,924 sqft, and has propane baseboard hot water heating, central air conditioning, and is north facing. One of the best aspects of this unit is the privacy that is offered on the

$775,000

4 beds3 baths2,924 sq ft

154 Kestrel Ct, Manchester, VT 05254

$1,147 HOA • Community pool • Car-dependent

CONTINGENT3D & VIDEO TOUR

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
A rustic diamond — ready for your personal touch! This bright Vermont chalet is tucked in the forest yet filled with brilliant light, warmth, and possibility. With soaring wood-clad cathedral ceilings, huge windows that welcome the morning sun, and a massive angular deck that blurs the line between indoors and nature, this home invites creativity and comfort. The open living area flows easily between kitchen, dining, and lounging spaces — with a generous highly functional kitchen and an island perfect for gathering. A stunning spiral stairway is complemented by the practicality of an elevator, and thoughtful extras include a carport, generator, extra freezer, and many storage sp

$495,000

4 beds4 baths2,370 sq ft

377 Glen Rd, Peru, VT 05152

2.5 acre lot • Car-dependent

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
A cozy chalet style home tucked in the woods in Winhall. Enjoy peaceful and private living with three seasons of beautiful mountain views and twinkling valley below. Hot tubbing and star gazing year round. Second owner since 1976. Updates include new metal roof, siding, deck, hot tub, kitchen, floors, bath, detached shed and more. A short drive to Bromley and Stratton Resorts. Lots of easily accessible activities such as hiking, mountain biking, cross-country skiing, golfing and pickle ball. An array of fun shops, restaurants, galleries in nearby Manchester So much nature and history to explore, too. A great place to relax and enjoy sunsets and snowfalls with family and friends - serenity

$425,000

2 beds1 bath974 sq ft

21 Deep Woods Cir Lot 27, Winhall, VT 05340

1.01 acre lot • Car-dependent

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
OPEN HOUSE SUNDAY OCTOBER 12TH 11:00AM-1:00PM! Escape to the mountains in this enchanting 4 bedroom, 3.5 bath home just moments from Stratton Resort in one of the areas most sought after neighborhoods! Offering classic chalet charm and convenience, this well-appointed home includes winter weekend/holiday shuttle service to the Stratton. After a day on the mountain, enjoy a walk to Stratton Village where you’ll find a variety of shops, and après-ski spots. Rather stay in? Curl up in front of the fire and take in the outdoors from the wall of windows. With its functional layout, open living area, spacious updated kitchen, sunny deck and a premier location, this chalet is the ulti

$849,000

4 beds3.5 baths2,028 sq ft

7 N Brookwood Rd, Bondville, VT 05340

0.89 acre lot • $76 HOA • Car-dependent

Property at 3343 Main St, Manchester, VT 05254, 4 beds, 3 baths

$915,000

4 beds3 baths2,898 sq ft

3343 Main St, Manchester, VT 05254

Property at 889 Overlea Rd, Bennington, VT 05201, 3 beds, 2 baths

$84,500

3 beds2 baths924 sq ft

889 Overlea Rd, Bennington, VT 05201

Property at 78 Farm Rd Unit E, Peru, VT 05152, 2 beds, 1 bath

$299,000

2 beds1 bath989 sq ft

78 Farm Rd Unit E, Peru, VT 05152

Property at 380 Partridge Hl #22, Manchestr Ctr, VT 05255, 3 beds, 4.5 baths

$1,885,000

3 beds4.5 baths3,874 sq ft

380 Partridge Hl #22, Manchestr Ctr, VT 05255

Property at 78 Farm Rd Unit A3, Peru, VT 05152, 3 beds, 1.5 baths

$459,000

3 beds1.5 baths1,394 sq ft

78 Farm Rd Unit A3, Peru, VT 05152

Property at 76 Harvest Hills Dr, North Bennington, VT 05257, 3 beds, 1 bath

$135,000

3 beds1 bath1,290 sq ft

76 Harvest Hills Dr, North Bennington, VT 05257

Property at 825 Case Ln, Readsboro, VT 05350, 3 beds, 2 baths

$550,000

3 beds2 baths2,499 sq ft

825 Case Ln, Readsboro, VT 05350

Property at 13803 Riverside Townhouses Rd #03, Manchester, VT 05255, 2 beds, 1.5 baths

$325,000

2 beds1.5 baths1,083 sq ft

13803 Riverside Townhouses Rd #03, Manchester, VT 05255

Property at 93 Mountain Ridge Rd, Peru, VT 05215, 3 beds, 2.5 baths

$550,000

3 beds2.5 baths1,850 sq ft

93 Mountain Ridge Rd, Peru, VT 05215

Property at 165 Pippin Knl, Bennington, VT 05201, 4 beds, 3 baths

$325,000

4 beds3 baths2,994 sq ft

165 Pippin Knl, Bennington, VT 05201

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

$1,275,000

5 beds4.5 baths4,686 sq ft

7 Timberbrook N, Dorset, VT 05251

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 103 Norton St, Bennington, VT 05201, 4 beds, 2 baths

$339,000

4 beds2 baths1,728 sq ft

103 Norton St, Bennington, VT 05201

Property at 634 Wiley Mountain Dr, Readsboro, VT 05350, 1 bed

$185,000

1 bed— baths400 sq ft

634 Wiley Mountain Dr, Readsboro, VT 05350

Property at 1148 Kent Hollow Rd, West Rupert, VT 05776-4421, 3 beds, 2.5 baths

$675,000

3 beds2.5 baths2,208 sq ft

1148 Kent Hollow Rd, West Rupert, VT 05776-4421

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

$650,000

3 beds2.5 baths3,637 sq ft

272 Oak Hill Rd, Shaftsbury, VT 05262

Property at 879 River Rd, Manchester, VT 05255, 3 beds, 3.5 baths

$850,000

3 beds3.5 baths2,340 sq ft

879 River Rd, Manchester, VT 05255

Property at 126 Fox Hill Rd, Bennington, VT 05201, 5 beds, 1.5 baths

$795,000

5 beds1.5 baths2,450 sq ft

126 Fox Hill Rd, Bennington, VT 05201

Property at 564 Overlook Rd, Manchester Center, VT 05255, 5 beds, 4.5 baths

$2,995,000

5 beds4.5 baths6,567 sq ft

564 Overlook Rd, Manchester Center, VT 05255

Property at 69 Hillvale Dr, Manchester Center, VT 05255, 4 beds, 2 baths

$529,000

4 beds2 baths1,828 sq ft

69 Hillvale Dr, Manchester Center, VT 05255

Property at 109 Nichols Hill Ln, Dorset, VT 05251, 3 beds, 2.5 baths

$895,000

3 beds2.5 baths1,946 sq ft

109 Nichols Hill Ln, Dorset, VT 05251

Property at 224 Sycamore Ln, Shaftsbury, VT 05252, 4 beds, 2 baths

$249,500

4 beds2 baths1,602 sq ft

224 Sycamore Ln, Shaftsbury, VT 05252

Property at 20 Jamie Ln, Bondville, VT 05340, 5 beds, 3.5 baths

$975,000

5 beds3.5 baths3,500 sq ft

20 Jamie Ln, Bondville, VT 05340

Property at 2288 East Rd, Bennington, VT 05201, 5 beds, 3 baths

$279,900

5 beds3 baths3,164 sq ft

2288 East Rd, Bennington, VT 05201

Property at 1059 Bailey Hill Rd, Readsboro, VT 05350, 3 beds, 1 bath

$502,900

3 beds1 bath2,400 sq ft

1059 Bailey Hill Rd, Readsboro, VT 05350

Property at 92 Coventry Ln, Manchester Center, VT 05255, 4 beds, 2.5 baths

$985,000

4 beds2.5 baths3,215 sq ft

92 Coventry Ln, Manchester Center, VT 05255

Property at 55 Monument Ave, Bennington, VT 05201, 3 beds, 2.5 baths

$650,000

3 beds2.5 baths2,675 sq ft

55 Monument Ave, Bennington, VT 05201

Property at 72 McKee Rd, Arlington, VT 05250, 4 beds, 2 baths

$350,000

4 beds2 baths1,368 sq ft

72 McKee Rd, Arlington, VT 05250

Property at 262 Powderhorn Rd, Manchester Center, VT 05255, 4 beds, 5.5 baths

$895,000

4 beds5.5 baths4,213 sq ft

262 Powderhorn Rd, Manchester Center, VT 05255

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

$1,795,000

17 beds19 baths14,861 sq ft

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

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

$1,350,000

3 beds4.5 baths3,415 sq ft

3746-3738 Main St, Manchester, VT 05254

Property at 73 Cranberry Hill Rd, Bondville, VT 05340, 4 beds, 4.5 baths

$949,000

4 beds4.5 baths2,658 sq ft

73 Cranberry Hill Rd, Bondville, VT 05340

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

$364,900

4 beds1.5 baths1,728 sq ft

639 Wiley Mountain Rd, Readsboro, VT 05350

Property at 4A Ridge Ct, Bondville, VT 05340, 3 beds, 3 baths

$615,000

3 beds3 baths1,886 sq ft

4A Ridge Ct, Bondville, VT 05340

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

$850,000

3 beds3 baths3,037 sq ft

725 Wideawake Rd, Manchester Center, VT 05255

Property at 26-30 Sage St, North Bennington, VT 05257, 9 beds, 3 baths

$279,000

9 beds3 baths3,176 sq ft

26-30 Sage St, North Bennington, VT 05257

Viewing page 1 of 3

Pending Listings in Bennington County

There are currently 89 pending listings 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 75 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 53 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 31 condos, 1 townhouse, and 12 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

Cities

Nearby Counties

Nearby Counties with Pending Listings

Nearby Cities with Pending Listings

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
$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 Sun Oct 26 2025 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.