Homes with Parking for Sale in Bennington County, VT

133 homes

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ABOUT THIS HOME
Home with Parking for sale in Bennington County, VT:
Set on over 11.5 private acres, this custom-built Colonial offers the kind of comfort, craftsmanship, and peace of mind that’s increasingly hard to find. Thoughtfully designed and maintained since it was built in 2004, this home blends timeless style with practical features for everyday living. With over 4,300 square feet, the layout provides generous space without feeling overwhelming. The home is permitted for four bedrooms, with flexibility for additional rooms to accommodate guests, hobbies, or a home office. Five full bathrooms and a half bath ensure convenience for both residents and visitors. The main level is designed for ease and accessibility, featuring a spacious primary su

$1,450,000

4 beds5.5 baths4,530 sq ft

527 Sleighbell Ln, Manchester Center, VT 05255

Spa-like bathroom • Two-story great room • Mountain views

FLOOR PLAN

ABOUT THIS HOME
Home with Parking for sale in Bennington County, VT:
Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the serenity and natural beauty for years to come. The thoughtfully designed open-concept main level features a bright and inviting living area, ideal for entertaining or relaxing while taking in the surrounding landscape. The primary bedroom and an additional guest bedroom are conveniently located on the m

$695,000

4 beds2 baths1,614 sq ft

515 Quarry Rd, Bennington, VT 05201

Mountain retreat • Versatile loft area • Finished lower level

ABOUT THIS HOME
Home with Parking for sale in Bennington County, VT:
Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with hardwood floors, and a stunning primary suite featuring a custom walk-in closet and a spa-inspired bath with heated tile floors. Offering exceptional flexibility, two of the four bedrooms are currently configured as home offices, while the versatile floor plan easily adapts to a variety of lifestyles. T

$539,900

4 beds2.5 baths2,376 sq ft

811 Middle Pownal Rd, Bennington, VT 05201

Bonus room • Heated tile floors • Home offices

ABOUT THIS HOME
Home with Parking for sale in Bennington County, VT:
Luxury Timber Frame Estate on 52+ Acres in Southern Vermont. This exceptional custom post-and-beam retreat is privately set amid rolling hardwood forestland, offering expansive mountain views, remarkable privacy, and a rare sense of peace and connection to nature. Designed for both elegance and efficiency, the home features solar panels with two Tesla Powerwalls for optional off grid independence, paired with energy efficient mini-split systems providing low cost heating and air conditioning throughout the seasons. The residence offers three bedrooms and three baths, two versatile lofts, bonus room, gym and a spacious attached two car heated and insulated garage, complemented by a flexible

$1,575,000

3 beds2.5 baths3,368 sq ft

276 Wilcox Hollow Rd, Sandgate, VT 05250

Tesla powerwalls • Solar panels • 52 acres

ABOUT THIS HOME
Home with Parking for sale in Bennington County, VT:
Set in a premier Dorset country setting with sweeping 360-degree views of rolling pastures, mountains, and neighboring farmland, this charming single-level ranch offers a rare opportunity to enjoy the beauty and tranquility of Southern Vermont. The home offers over 1,568 square feet of comfortable living space, including an open-concept kitchen, dining, and living area, an office, three bedrooms, and two full bathrooms. The spacious primary suite includes an on-suite bathroom overlooking the expansive views. The home features new wood flooring throughout the interior, a slate entry foyer, first-floor laundry, and a centrally located pellet stove for supplemental heat. Additional upgrades in

$499,000

3 beds2 baths1,568 sq ft

336 Kirby Hollow Rd, Dorset, VT 05251

Split ac systems • Open-concept kitchen • New wood flooring

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

$1,650,000

3 beds4 baths5,072 sq ft

36 Beaver St, Winhall, VT 05340

Property at 683 Water St, North Bennington, VT 05257, 3 beds, 2 baths

$319,900

3 beds2 baths1,500 sq ft

683 Water St, North Bennington, VT 05257

Property at 144 High Meadow Rd, Winhall, VT 05340, 6 beds, 5.5 baths

$1,599,000

6 beds5.5 baths5,568 sq ft

144 High Meadow Rd, Winhall, VT 05340

Property at 103 Jennings Brook Dr #103, Bennington, VT 05201, 3 beds, 2 baths

$250,000

3 beds2 baths1,824 sq ft

103 Jennings Brook Dr #103, Bennington, VT 05201

Property at 153 High Meadow Rd, Winhall, VT 05340, 4 beds, 3 baths

$1,225,000

4 beds3 baths3,357 sq ft

153 High Meadow Rd, Winhall, VT 05340

Property at 425 Main St, Bennington, VT 05201, 6 beds, 5 baths

$475,000

6 beds5 baths9,000 sq ft

425 Main St, Bennington, VT 05201

Property at 191 Pleasant Street Ext, East Dorset, VT 05253, 3 beds, 1.5 baths

$525,000

3 beds1.5 baths1,594 sq ft

191 Pleasant Street Ext, East Dorset, VT 05253

Property at 6265 VT Route 7A, Sunderland, VT 05250, 4 beds, 4.5 baths

$650,000

4 beds4.5 baths3,864 sq ft

6265 VT Route 7A, Sunderland, VT 05250

Property at 1310 Dorset Hill Rd, East Dorset, VT 05253, 4 beds, 3 baths

$1,795,000

4 beds3 baths3,370 sq ft

1310 Dorset Hill Rd, East Dorset, VT 05253

Property at 109 Winhall Hollow Rd, Winhall, VT 05340, 1 bath

$1,200,000

Studio1 bath950 sq ft

109 Winhall Hollow Rd, Winhall, VT 05340

Property at 3039 Route 30, Dorset, VT 05251, 4 beds, 5.5 baths

$2,495,000

4 beds5.5 baths4,506 sq ft

3039 Route 30, Dorset, VT 05251

Property at 116-118 S Branch St, Bennington, VT 05201, 4 beds, 2 baths

$269,000

4 beds2 baths2,206 sq ft

116-118 S Branch St, Bennington, VT 05201

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

$1,275,000

4 beds2.5 baths4,084 sq ft

1677 Barnumville Rd, Manchester Center, VT 05255

Property at 2334 Morse Hill Rd, Dorset, VT 05251, 2 beds, 3.5 baths

$2,850,000

2 beds3.5 baths5,731 sq ft

2334 Morse Hill 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 68 Green Peak Orch S, East Dorset, VT 05253, 5 beds, 5 baths

$2,950,000

5 beds5 baths6,900 sq ft

68 Green Peak Orch S, East Dorset, VT 05253

Property at 14 A Marisa Ln, Dorset, VT 05251, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths1,786 sq ft

14 A Marisa Ln, Dorset, VT 05251

Property at 124 S Branch St, Bennington, VT 05201, 4 beds, 2 baths

$275,000

4 beds2 baths2,022 sq ft

124 S Branch St, Bennington, VT 05201

Property at 1060 Upper Hollow Rd, Dorset, VT 05251, 5 beds, 5.5 baths

$5,600,000

5 beds5.5 baths4,674 sq ft

1060 Upper Hollow Rd, Dorset, VT 05251

Property at 1083 Main St, Bennington, VT 05201, 2 beds, 1 bath

$209,900

2 beds1 bath1,075 sq ft

1083 Main St, Bennington, VT 05201

Property at 59 Garden Loop Rd, Winhall, VT 05340, 4 beds, 4.5 baths

$2,850,000

4 beds4.5 baths3,762 sq ft

59 Garden Loop 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 99 Holly's Way, West Rupert, VT 05776, 3 beds, 2 baths

$975,000

3 beds2 baths2,403 sq ft

99 Holly's Way, West Rupert, VT 05776

Property at 6 Old Ridge Rd, Winhall, VT 05340, 5 beds, 4.5 baths

$1,100,000

5 beds4.5 baths4,453 sq ft

6 Old Ridge Rd, Winhall, VT 05340

Property at 21 Jameson Flts Unit Duplex Unit B, Manchester, VT 05255, 3 beds, 2.5 baths

$595,000

3 beds2.5 baths1,368 sq ft

21 Jameson Flts Unit Duplex Unit B, Manchester, VT 05255

Property at 233 Squires Rd, Manchester Center, VT 05255, 2 beds, 1 bath

$1,200,000

2 beds1 bath1,056 sq ft

233 Squires Rd, Manchester Center, VT 05255

Property at 924 Henderson Rd, Williamstown, MA 01267, 4 beds, 2 baths

$850,000

4 beds2 baths3,507 sq ft

924 Henderson Rd, Williamstown, MA 01267

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

$450,000

3 beds2 baths1,460 sq ft

393 Morse Hill Rd, East Dorset, VT 05253

Property at 121 High Meadow Rd, Winhall, VT 05340-9999, 6 beds, 4 baths

$1,399,999

6 beds4 baths3,800 sq ft

121 High Meadow Rd, Winhall, VT 05340-9999

Property at 1182 1184 East Manchester Rd, Manchester Center, VT 05255, 9 beds, 8.5 baths

$4,995,000

9 beds8.5 baths7,900 sq ft

1182 1184 East Manchester Rd, Manchester Center, VT 05255

Property at 751 Main Rd, Stamford, VT 05352, 6 beds, 5 baths

$1,900,000

6 beds5 baths5,704 sq ft

751 Main Rd, Stamford, VT 05352

Property at 262 Dwyers Camp Rd, Shaftsbury, VT 05262, 3 beds, 2 baths

$479,000

3 beds2 baths2,065 sq ft

262 Dwyers Camp Rd, Shaftsbury, VT 05262

Property at 288 Cedar Ln, Peru, VT 05152, 9 beds, 7 baths

$2,275,000

9 beds7 baths5,512 sq ft

288 Cedar Ln, Peru, VT 05152

Property at Ridge Rd Unit C-4, Bondville, VT 05340, 3 beds, 3 baths

$825,000

3 beds3 baths2,598 sq ft

Ridge Rd Unit C-4, Bondville, VT 05340

Property at 120 Village St, East Dorset, VT 05253, 4 beds, 3.5 baths

$434,500

4 beds3.5 baths3,861 sq ft

120 Village St, East Dorset, VT 05253

Property at 145 Oberdorf Rd, Readsboro, VT 05350, 4 beds, 2 baths

$490,642

4 beds2 baths1,708 sq ft

145 Oberdorf Rd, Readsboro, VT 05350

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Homes with Parking for Sale in Bennington County

There are currently 133 homes with parking homes for sale in Bennington County at a median listing price of $525K. 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 74 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 47 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 39 condos, 0 townhouses, and 17 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 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 Thu Aug 27 2026 on the search page

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