Pending Listings in Bennington County, VT

86 homes

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ABOUT THIS HOME
Pending Listing in Bennington County, VT:
A wonderful investment opportunity in the desirable village of North Bennington! This income-producing property with three units has been well kept and updated over the years - most recently with a brand new roof. Two of the three-bedroom units have been freshly renovated and all are currently occupied with a strong rental history. Two of the units have two stories, giving it a townhouse feel, while the one-level unit is perfect for accessibility. All include laundry hook-ups for convenience. There is also ample parking for tenants and guests. Across the street is the lovely Paran Creek, and you're not far from Lake Paran. Great dining and shopping is well within walking distance. With the

$279,000

9 beds3 baths3,176 sq ft

26-30 Sage St, North Bennington, VT 05257

0.26 acre lot • Car-dependent

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
Exquisite Residence located just 2 miles from Dorset Village in North Rupert. Featuring creative flooring tile, wood accents, exposed beams & wide-plank hardwood floors, the rustic yet sophisticated design creates an earthy & luxurious experience. The chef kitchen is a culinary masterpiece, with custom sage green cabinetry, sleek black countertops, & a deep soapstone farmhouse sink – all blend together offering timeless durability alongside a wall of windows that flood the room with soft, natural light. The primary suite resides in the soaring loft space—its vaulted ceilings & natural finishes evoke a sense of open, tranquil repose. Large windows flood th

$1,275,000

3 beds2.5 baths2,259 sq ft

694 Sykes Hollow Rd, Pawlet, VT 05776

8.6 acre lot • Garage • Car-dependent

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
Welcome to this charming 1900's cottage, ideally situated in the heart of Bennington Village! This delightful home offers the perfect blend of historic charm and modern convenience, though it is well-loved and awaits your personal touch and some TLC to truly shine. Enjoy easy access to local shopping and schools, making daily errands and commutes a breeze. For outdoor enthusiasts, nearby trails provide ample opportunities for recreation, and the YMCA with its indoor pool and tennis courts is just a stone's throw away. The property boasts a fully fenced backyard, perfect for pets or play, and features inviting covered porches on both the front and side, ideal for relaxing with a cup of coffe

$159,900

2 beds2 baths1,104 sq ft

229 Division St, Bennington, VT 05201

9,583 sq ft lot • Somewhat walkable

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
Exceptional Main Residence and Guest House in a premier quintessential Vermont setting, beautifully designed to capture spectacular views of mountains and sunsets. Situated on 7.9 acres in an exceptional estate-style setting, the forward-thinking floor plan is prime for entertaining in multiple spaces, while still maintaining a welcoming New England character. With views from every gathering room; living room, billiard room, gourmet kitchen, the design maximizes the setting and access to the outdoor with large patio, gardens and lovely meadow. With great attention to detail, this custom-built home features a gourmet kitchen with Bosch & Wolf appliances, wide pine floors, masonry heart

$2,495,000

5 beds4.5 baths4,483 sq ft

743 Green Peak Orchard Rd, Manchester Center, VT 05255

7.9 acre lot • $50 HOA • 3 garage spots

CONTINGENT

ABOUT THIS HOME
Pending Listing in Bennington County, VT:
Welcome to your dream Vermont retreat. This classic 3 bedroom Colonial is gracefully set on 9.52 acres of open meadows with direct frontage on the Battenkill River, renowned worldwide for its exceptional trout fishing. With timeless architecture, peaceful privacy, and sweeping Mountain views, this property captures the essence of New England living. Inside, the home blends historic charm with everyday comfort. Wide-plank hardwood floors, hand-crafted details, and two wood-burning fireplaces one in the living room and another in the historic kitchen create an inviting, warm atmosphere. The main level features a thoughtfully placed bedroom with nearby full bath, offering single-level living f

$995,000

5 beds4.5 baths3,697 sq ft

1589 Richville Rd, Manchester Center, VT 05255

9.52 acre lot • 2 garage spots • Car-dependent

Property at 374 Winhall Hollow Rd, Bondville, VT 05340, 4 beds, 3 baths

$495,000

4 beds3 baths1,920 sq ft

374 Winhall Hollow Rd, Bondville, VT 05340

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 83 Benson Fuller Dr, Winhall, VT 05340, 5 beds, 5.5 baths

$1,050,000

5 beds5.5 baths4,729 sq ft

83 Benson Fuller Dr, Winhall, VT 05340

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 44 Hilltop Rd, Winhall, VT 05340, 4 beds, 4 baths

$789,000

4 beds4 baths2,997 sq ft

44 Hilltop Rd, Winhall, VT 05340

Property at 379 Swallow Hill Rd, Pownal, VT 05261, 3 beds, 1.5 baths

$349,900

3 beds1.5 baths1,666 sq ft

379 Swallow Hill Rd, Pownal, VT 05261

Property at 200 Applewood Ln, Manchester Center, VT 05255

$495,000

— beds— baths2,746 sq ft

200 Applewood Ln, Manchester Center, VT 05255

Property at 93 Hard Farm Rd, Manchester Center, VT 05255, 5 beds, 3 baths

$1,550,000

5 beds3 baths4,342 sq ft

93 Hard Farm Rd, Manchester Center, VT 05255

Property at 6828 Main St, Readsboro, VT 05350, 0.5 baths

$369,900

0 beds0.5 baths4,220 sq ft

6828 Main St, Readsboro, VT 05350

Property at 357 Kansas Rd, East Arlington, VT 05252, 4 beds, 2.5 baths

$549,000

4 beds2.5 baths3,100 sq ft

357 Kansas Rd, East Arlington, VT 05252

Property at 30 River Rd, Arlington, VT 05250, 5 beds, 2.5 baths

$225,000

5 beds2.5 baths2,735 sq ft

30 River Rd, Arlington, VT 05250

Property at 1 & 2 Joy Ln, Arlington, VT 05250

$85,000

— beds— baths— sq ft

1 & 2 Joy Ln, Arlington, VT 05250

Property at 3221 Hapgood Pond Rd, Peru, VT 05155, 4 beds, 4 baths

$649,000

4 beds4 baths2,868 sq ft

3221 Hapgood Pond Rd, Peru, VT 05155

Property at 43 Hilltop Rd, Winhall, VT 05340, 4 beds, 4 baths

$740,000

4 beds4 baths3,020 sq ft

43 Hilltop Rd, Winhall, VT 05340

Property at 207 Kesick Swamp Rd, Arlington, VT 05250, 3 beds, 3 baths

$395,000

3 beds3 baths3,800 sq ft

207 Kesick Swamp Rd, Arlington, VT 05250

Property at 4 Rockwood St, Bennington, VT 05201, 3 beds, 2 baths

$299,000

3 beds2 baths1,896 sq ft

4 Rockwood St, Bennington, VT 05201

Property at 4581 Main Rd, Stamford, VT 05352, 3 beds, 2.5 baths

$259,900

3 beds2.5 baths2,052 sq ft

4581 Main Rd, Stamford, VT 05352

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 3 Short Rd, Bondville, VT 05340, 3 beds, 2.5 baths

$649,900

3 beds2.5 baths2,034 sq ft

3 Short Rd, Bondville, VT 05340

Property at 5412 Bluestone Rd, Bennington, VT 05201, 1 bed

$139,000

1 bed— baths704 sq ft

5412 Bluestone Rd, Bennington, VT 05201

Property at 535 Red Mountain Rd, Arlington, VT 05250, 3 beds, 1.5 baths

$359,000

3 beds1.5 baths2,831 sq ft

535 Red Mountain Rd, Arlington, VT 05250

Property at 100 McCarthy Acres Rd, North Bennington, VT 05257, 5 beds, 3 baths

$399,000

5 beds3 baths3,118 sq ft

100 McCarthy Acres Rd, North Bennington, VT 05257

Property at 1044 Berwall Rd, Arlington, VT 05250, 4 beds, 3 baths

$575,000

4 beds3 baths2,212 sq ft

1044 Berwall Rd, Arlington, VT 05250

Property at 7 Landgrove Rd, Londonderry, VT 05148, 4 beds, 3 baths

$600,000

4 beds3 baths2,570 sq ft

7 Landgrove Rd, Londonderry, VT 05148

Property at 93 Pace Rd, Bennington, VT 05201-8755, 3 beds, 1.5 baths

$325,000

3 beds1.5 baths1,664 sq ft

93 Pace Rd, Bennington, VT 05201-8755

Property at 95 Birches Way Unit C-C2, Peru, VT 05152, 3 beds, 2 baths

$459,000

3 beds2 baths1,391 sq ft

95 Birches Way Unit C-C2, Peru, VT 05152

Property at 198 Twitchell Hill Rd, Shaftsbury, VT 05262, 3 beds, 2 baths

$212,000

3 beds2 baths1,959 sq ft

198 Twitchell Hill Rd, Shaftsbury, VT 05262

Property at 273 Union St, Bennington, VT 05201, 5 beds, 1 bath

$69,900

5 beds1 bath1,952 sq ft

273 Union St, Bennington, VT 05201

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

$445,000

3 beds3 baths1,710 sq ft

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

Property at 951 Rupert Rd, Arlington, VT 05250, 5 beds, 4 baths

$1,495,000

5 beds4 baths6,200 sq ft

951 Rupert Rd, Arlington, VT 05250

Property at 239 241 Elm St, Bennington, VT 05201, 6 beds, 3 baths

$270,000

6 beds3 baths2,900 sq ft

239 241 Elm St, Bennington, VT 05201

Property at 235 Elm St, Bennington, VT 05201, 6 beds, 3 baths

$295,000

6 beds3 baths2,640 sq ft

235 Elm St, Bennington, VT 05201

Property at 59 Sugar Brook Rd Unit D1, Peru, VT 05152, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths1,603 sq ft

59 Sugar Brook Rd Unit D1, Peru, VT 05152

Property at 101 Morgan St, Bennington, VT 05201, 4 beds, 1 bath

$139,000

4 beds1 bath1,262 sq ft

101 Morgan St, Bennington, VT 05201

Property at Stateline Rd, Shaftsbury, VT 05262

$79,000

— beds— baths— sq ft

Stateline Rd, Shaftsbury, VT 05262

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Pending Listings in Bennington County

There are currently 86 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.

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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 Wed Oct 29 2025 on the search page

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