Bennington County VT Homes for Sale

/60
$1,795,000
- 17 Beds
- 20 Baths
- 14,861 Sq Ft
3888 Vermont Route 7a, Shaftsbury, VT 05262

The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

Vicki Wilson

Maple Leaf Realty

(802) 444-8317

3888 Vermont Route 7a, Shaftsbury, VT 05262
/11
$179,900
- 4 Beds
- 2 Baths
- 2,643 Sq Ft
905 County St, Bennington, VT 05201

Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 204-5943

905 County St, Bennington, VT 05201
/4
$199,900
- 5 Beds
- 2 Baths
- 1,478 Sq Ft
32-34 Sage St, Bennington, VT 05257

Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 402-4994

32-34 Sage St, Bennington, VT 05257
/21
$175,000
- Land
- 18 Acres
- $9,749 per Acre
0 U S 7, Pownal, VT 05261

Beautiful Pownal Valley views from almost wherever you stand on this 17.95 acre parcel. Zoned for commercial use along the road frontage and rural residential in back creates opportunities for different types of development.

Vicki Wilson

Maple Leaf Realty

(802) 327-8230

0 U S 7, Pownal, VT 05261
/40
$1,295,000
- 4 Beds
- 6 Baths
- 4,272 Sq Ft
1016 West Rd, Manchester Center, VT 05255

Manchester Village...an award winning architect transformed this "Sears & Roebuck" mini farmstead indo Living Art! Masterful execution of architectural detail at every turn. Circular landscaped drive ties the residence, garages, and the an impressive party barn together for year round use. The substantial covered stone porch enters the arts & crafts foyer.. with study to one side, ahead the

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 357-7462

1016 West Rd, Manchester Center, VT 05255
/15
$115,000
- Land
- 2.90 Acres
- $39,655 per Acre
Lot 3 Route 11 30, Winhall, VT 05340

Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 808-6197

Lot 3 Route 11 30, Winhall, VT 05340
/2
$20,000
- Land
- 3.00 Acres
- $6,667 per Acre
0 U S 7, Pownal, VT 05261

3 acre parcel located behind other parcels. Would be a great place for a hunting "camp", blind or recreation. Right of Way is from 63 Metcalfe Road, Pownal.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 210-3911

0 U S 7, Pownal, VT 05261
/2
$109,000
- Land
- 2.60 Acres
- $41,923 per Acre
0 Kesick Swamp Rd, Sunderland, VT 05250

Terrific 2.6 acre building lot in Sunderland. Located at the end of Kesick Swamp Road. Private and almost ready to go. Some site work has been done and a septic design for a 2 bedroom home has been completed, just needs permitting. Current owner will change from recreational use to Residential use, prior to closing.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 454-3023

0 Kesick Swamp Rd, Sunderland, VT 05250
/33
$229,900
- 3 Beds
- 1 Bath
- 1,144 Sq Ft
5 Center St, Bennington, VT 05201

Welcome to 5 Center Street in the heart of Bennington! This charming single level home offers 3 bedrooms and 1 full bath across a well designed 1,144 sq. ft. floor plan the perfect size for easy living and energy efficiency. Whether you’re looking to downsize, purchase your first home, or simply enjoy the convenience of one floor living, this home is a wonderful fit.Inside, you’ll find a

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 553-3433

5 Center St, Bennington, VT 05201
/55
$850,000
- 3 Beds
- 3.5 Baths
- 2,340 Sq Ft
879 River Rd, Manchester, VT 05255

Authentic 1800's center chimney, hand hewn post and beam cape on coveted River Road within a short walk to the Battenkill River! This beauty has had the fireplace chimney's lined, the eat-in "keeping room" kitchen updated nicely, and the plank flooring is all intact! 12 over 12 windows, chair rails, exposed framing, and original doors and hardware are exceptional. The kitchen has a Dutch Oven

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 300-3678

879 River Rd, Manchester, VT 05255
/41
$399,900
- 3 Beds
- 2.5 Baths
- 1,792 Sq Ft
882 East Rd, Bennington, VT 05201

Welcome to 882 East Road! This spacious first-floor ranch, set on 1.97 acres, offers comfort, convenience, and room to grow. Built in 2002, the home features three bedrooms and two and half baths, all thoughtfully designed for easy single level living.The open kitchen provides plenty of working space, a beautiful pantry, and excellent flow into a large living room, perfect for gathering and

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 215-3662

882 East Rd, Bennington, VT 05201
/43
$422,000
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
100 Walsh Rd, Arlington, VT 05250

Tucked away in the picturesque Vermont Hamlet of Sandgate, home to just 480 residents, this property provides the perfect escape from the bustle of city life. Here, you can enjoy the warmth of a close-knit community, stunning natural surroundings, and easy access to local amenities.Sitting on a generous 1.5-acre lot, the property offers ample space for outdoor recreation and the peaceful

Kristin Comeau

TPW Real Estate

(802) 521-2780

100 Walsh Rd, Arlington, VT 05250
/16
$145,000
- 3 Beds
- 1.5 Baths
- 1,485 Sq Ft
755 Main St, Bennington, VT 05201

Many possibilities with this property located on Main Street in Bennington. Zoned village commercial but currently a 3 bedroom 1 and a half bath home. Nice kitchen, dining room, living room, main level primary with half bath, main level laundry and more. Needs some TLC. Won't qualify for first time homebuyer programs.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 444-8936

755 Main St, Bennington, VT 05201
/46
$850,000
- 5 Beds
- 2 Baths
- 2,424 Sq Ft
2 Cold Spring Rd, North Bennington, VT 05257

Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 810-8434

2 Cold Spring Rd, North Bennington, VT 05257
/60
$1,950,000
- 4 Beds
- 3.5 Baths
- 4,023 Sq Ft
1268 Myers Rd, Shaftsbury, VT 05262

Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, a 2 car garage, top notch equestrian facilities, a trout and koi pond, and the list goes on and on. The winding driveway leads to a world away, as it opens to view of the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 441-6014

1268 Myers Rd, Shaftsbury, VT 05262
/36
$490,000
- 3 Beds
- 2 Baths
- 2,108 Sq Ft
1061 Granger Hollow Rd, North Bennington, VT 05257

Dreaming of a peaceful Vermont lifestyle? This three bedroom, 2 bath home sits on 11.5 acres of beautiful land with rolling open mountain views, a stream, mature apple trees, and an inground pool all the ingredients for your perfect retreat.Step inside to this home that has had a complete refresh. The home offers a first floor bedroom and full bath with a step in shower, making it great

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 481-3292

1061 Granger Hollow Rd, North Bennington, VT 05257
/62
$499,900
- 4 Beds
- 2.5 Baths
- 2,240 Sq Ft
679 Middle Pownal Rd, Pownal, VT 05261

Nestled in the heart of rural Pownal, this beautifully renovated 4-bedroom, 3-bath home offers the perfect blend of modern comfort and peaceful countryside living. Set on 12.1 picturesque acres, the property features a mix of open level land and serene wooded areas, ideal for hobby farming, equestrian use, or simply enjoying nature. Inside, you'll find a spacious and thoughtfully designed layout

Erin Vincent

BISHOP WEST REAL ESTATE

(802) 636-6092

679 Middle Pownal Rd, Pownal, VT 05261
/60
$1,600,000
- 5 Beds
- 4.5 Baths
- 4,243 Sq Ft
397 Fern Hill, Dorset, VT 05251

Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 644-3043

397 Fern Hill, Dorset, VT 05251
/47
$1,500,000
- Land
- 39 Acres
- $38,890 per Acre
500 Nims Rd, Dorset, VT 05251

This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 634-4776

500 Nims Rd, Dorset, VT 05251
/2
$225,000
- 6 Beds
- 2 Baths
- 2,112 Sq Ft
303-305 Gage St, Bennington, VT 05201

Low maintenance duplex in Bennington. Offering good rental history and income. 2 -3 bedroom units, newer systems, vinyl siding and more. Walking distance to town. schools and recreation.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 471-3314

303-305 Gage St, Bennington, VT 05201
/60
$1,150,000
- 3 Beds
- 3 Baths
- 2,462 Sq Ft
636 Dexter Rd, Shaftsbury, VT 05262

In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the

Kristin Comeau

TPW Real Estate

(802) 520-1220

636 Dexter Rd, Shaftsbury, VT 05262
/4
$249,000
- 5 Beds
- 3 Baths
- 2,184 Sq Ft
137 Park St, Bennington, VT 05201

Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 444-8271

137 Park St, Bennington, VT 05201
/60
$1,100,000
- 4 Beds
- 2.5 Baths
- 3,215 Sq Ft
92 Coventry Ln, Manchester Center, VT 05255

Coventry House - Offered For The First Time! Built in 1972, the home was thoughtfully designed by local architect Charles "Bud" Lynch in collaboration with the owners. This custom-built home blends timeless design with natural surroundings. Offering a country kitchen, 4 bedrooms and 3+ vintage baths reflecting the 70’s era focus on color, natural materials, and open floor plans all on one level

Kristin Comeau

TPW Real Estate

(802) 424-8410

92 Coventry Ln, Manchester Center, VT 05255
/41
$295,000
- 5 Beds
- 2 Baths
- 2,418 Sq Ft
226 North St, Bennington, VT 05201

This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 327-7149

226 North St, Bennington, VT 05201
/13
$199,000
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
2017 East Rd, Shaftsbury, VT 05262

3 bedroom 2 bath, double wide on 1.49 acres in Shaftsbury. Offering good location, large yard, and convenient travel to town. Living room with new pellet stove, kitchen with modern appliances including newer stove and dining area. Outside a 2 car detached garage, storage sheds and front and rear porches. New carpet.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 798-5968

2017 East Rd, Shaftsbury, VT 05262
/10
$20,000
- Land
- 1.40 Acres
- $14,286 per Acre
0 Bergrucken Ln Unit 24262915, Stamford, VT 05352

1.4 Acres of Scenic Vacant Land in Bennington County, VT Located in Alpenwald VillageLooking for the perfect spot to build your dream home or vacation retreat? This 1.4-acre lot in Bennington County, Vermont offers an incredible opportunity! Located in the exclusive Alpenwald Village community, the property boasts 115 ft of road frontage on Bergrucken Ln, providing easy access while

Community Lands

0 Bergrucken Ln Unit 24262915, Stamford, VT 05352
/10
$20,000
- Land
- 1.20 Acres
- $16,667 per Acre
0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350

1.2 Acres of Scenic Land for Sale in Bennington County, VTEscape to the beauty of Bennington County, Vermont, with this stunning 1.2-acre parcel of vacant land. Offering 350 ft of road frontage on Oberdorf Rd, this lot provides easy access and is nestled within the private Alpenwald Village, a peaceful community ideal for your dream home or vacation retreat. Surrounded by nature, this

Community Lands

0 Oberdorf Rd Unit 24065553, Readsboro, VT 05350
/36
$4,975,000
- 5 Beds
- 4 Baths
- 6,998 Sq Ft
527 Benson Rd, Manchester Center, VT 05255

Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould

Story Jenks LandVest, Inc/Woodstock

527 Benson Rd, Manchester Center, VT 05255
/27
$625,000
- 4 Beds
- 4.5 Baths
- 3,864 Sq Ft
6265 Vt Route 7a, Sunderland, VT 05250

Extensively Renovated Classic Vermont ColonialThis beautifully updated 1935 Vermont Colonial offers the perfect blend of classic charm and modern convenience, with thoughtful additions completed in 1972 and 2016. With nearly 3,900 square feet of living space, this spacious home features 4 bedrooms, 4.5 bathrooms, two dedicated office spaces, and a versatile third-story bonus room — ideal for

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

6265 Vt Route 7a, Sunderland, VT 05250
/42
$1,525,000
- 4 Beds
- 3 Baths
- 3,931 Sq Ft
932 Mcnamara Rd, Dorset, VT 05251

Tucked away at the end of a gently curved, tree-lined drive, this exceptional contemporary home blends timeless elegance with Vermont charm. A welcoming paver patio leads to the informal entry, while a marble pathway guides you to the striking formal entrance and grand foyer. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality

Britt Wohler Wohler Realty Group

932 Mcnamara Rd, Dorset, VT 05251
/60
$710,000
- 3 Beds
- 2.5 Baths
- 2,034 Sq Ft
3 Short Rd, Bondville, VT 05340

Reside in a renovated 1800s expanded cape in Vermont, complete with all the country amenities you desire! The presence of a barn with a workshop indicates that the home you are purchasing is well cared for. The eat-in kitchen boasts a soapstone sink, pine flooring, granite countertops, and custom cabinetry. The living room features a wood-burning fireplace, as does the dining room. An addition

Mike England Michael England Real Estate

3 Short Rd, Bondville, VT 05340
/40
$1,350,000
- 2 Beds
- 2.5 Baths
- 1,900 Sq Ft
81 Fern Hill, Dorset, VT 05251

Storybook Cape full of comfort and charm in a private location surrounded by gardens, specimen maples and an unusual acre of pachysandra ground cover.The home's living room centers around a traditional fireplace and French doors leading to a slate terrace overlooking established gardens. The sun filled dining room features built in cabinets and leads to a custom designed kitchen. A sunroom

Elena Atwill Four Seasons Sotheby's Int'l Realty

81 Fern Hill, Dorset, VT 05251
/36
$959,000
- 3 Beds
- 2.5 Baths
- 1,946 Sq Ft
109 Nichols Hill Ln, Dorset, VT 05251

This charming home with three acres is tucked in one of the lushest neighborhoods in Dorset, Nichols Hill Road is just two miles from the Dorset Green. The renovated kitchen features hand crafted maple cabinets, quartz counters, and a new downdraft range. The kitchen flows into a dining area and a sitting room with a wood-burning fireplace and a 7ft long window seat. The downstairs flooring is

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

109 Nichols Hill Ln, Dorset, VT 05251
/37
$999,000
- 4 Beds
- 3.5 Baths
- 2,280 Sq Ft
17 Roundtree Rd, Winhall, VT 05340

Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

Sarah Nichols Winhall Real Estate

17 Roundtree Rd, Winhall, VT 05340
/43
$1,650,000
- 4 Beds
- 3.5 Baths
- 3,926 Sq Ft
81 Pine Tree Ln, Manchester Center, VT 05255

Set on 3.1 private acres with a spring-fed mountain stream, this stunning 4-bed, 31⁄2-bath custom home—started in 2020 and completed in 2022—showcases exceptional craftsmanship, thoughtful design, and Vermont charm. True white oak hardwood floors flow throughout, complemented by a green slate-tiled mudroom with radiant heat. The fully custom kitchen boasts handcrafted cabinetry, soapstone

Roger Danyew Diamond Realty

81 Pine Tree Ln, Manchester Center, VT 05255
/46
$825,000
- 4 Beds
- 2.5 Baths
- 2,220 Sq Ft
392 Powderhorn Rd, Manchester Center, VT 05255

This renovated four-bedroom, three-bath Colonial home is set on 2 private acres, offering a quiet retreat with convenient access to both Manchester and Dorset.Wide-plank pine floors and natural light define the interiors. The main level features a spacious living room with a stone fireplace, a formal dining room, and an eat-in kitchen with a seamless connection to the adjoining spaces. A

Alexandra Crowley Four Seasons Sotheby's Int'l Realty

392 Powderhorn Rd, Manchester Center, VT 05255
/51
$725,000
- 3 Beds
- 2.5 Baths
- 2,208 Sq Ft
1148 Kent Hollow Rd, West Rupert, VT 05776

Country charm at the foot of Shatterack Mountain. Nestled in a classic Currier & Ives setting, this exceptional Cape Cod style home and barn sit on over 37 private acres, accessed by a a picturesque bridge over White Creek. Built by craftsman Mark Breen and inspired by a 300 year old Connecticut Cape, this home showcases timeless period detailing with crown molding and picture windows.

Margretta Fischer Wohler Realty Group

1148 Kent Hollow Rd, West Rupert, VT 05776
/34
$795,000
- 3 Beds
- 2.5 Baths
- 4,683 Sq Ft
2744 Danby Mountain Rd, Dorset, VT 05251

This luxurious mountain escape blends the best of both worlds -peaceful days surrounded by nature's beauty, with hiking, birding, and ski touring steps from your yard, along with nearby access to Dorset Village's dining, arts, and the renowned Dorset Field Club.A new wrap-around Trex deck invites you to relax or dine outdoors while enjoying sweeping views of lush gardens and mountain

Andie Fusco Four Seasons Sotheby's Int'l Realty

2744 Danby Mountain Rd, Dorset, VT 05251
/23
$799,000 Open Sat 11AM - 1PM
- 4 Beds
- 3.5 Baths
- 3,784 Sq Ft
258 Mending Walls Rd, Manchester Center, VT 05255

Nestled in the highly sought-after Mending Walls Subdivision, this beautiful 4-bedroom, 4-bathroom Colonial offers the perfect blend of comfort, space, and curb appeal. Set back on a level lot, enjoy serene mornings and evenings from the welcoming front porch overlooking the expansive front yard.The main level boasts spacious living area perfect for entertaining and everyday living.

Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

258 Mending Walls Rd, Manchester Center, VT 05255
/35
$649,500
- 5 Beds
- 2 Baths
- 2,050 Sq Ft
1649 E Manchester Rd, Manchester Center, VT 05255

Privately set yet moments from Manchester's boutiques, dining, and year-round recreation, this four-bedroom, two bath Cape offers a rare blend of quiet retreat and unmatched accessibility. Every space has been curated for comfort, versatility, and style, ideal for full-time living, a vacation escape, and many other possibilities. The kitchen, a refined anchor to the home, features stainless steel

Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

1649 E Manchester Rd, Manchester Center, VT 05255

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.