Bennington County VT Homes for Sale

/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
/43
$790,000
- 4 Beds
- 3.5 Baths
- 7,786 Sq Ft
56 Mending Walls Rd, Manchester Center, VT 05255

Welcome to your next chapter in Manchester, Vermont.Tucked away in the sought-after Mending Walls community, this 4-bedroom, 4-bath home offers over 5,700 square feet of sun-filled space designed for both comfort and connection. Set on a private one-acre lot, it’s clean, unfurnished, and ready for you to make it your own.Inside, you’ll find warm wood floors, a chef’s kitchen with

Trent Stephens

Wohler Realty Group

(802) 215-6507

56 Mending Walls Rd, Manchester Center, VT 05255
/19
$225,000
- Land
- 17 Acres
- $13,489 per Acre
1801 S Stream Rd, Bennington, VT 05201

Welcome to 1801 South Stream Road a picturesque 16.68 acres of timeless Vermont charm property. This beautiful parcel features two classic Vermont red barns full of character and charm, that offer endless potential. With some repairs, they could be ideal for livestock, storage, or workshop space ready to support your vision for country living. A picturesque pond, in need of a little TLC, offers

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 317-7489

1801 S Stream Rd, Bennington, VT 05201
/41
$320,000 Open Sun 1PM - 3PM
- 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
/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) 392-9104

3888 Vermont Route 7a, Shaftsbury, VT 05262
/11
$129,000
- Land
- 7 Acres
- $17,223 per Acre
0 Lois Ln Unit 5045700, Arlington, VT 05250

Come for the Views—Stay for the Possibilities!Bring Your Architect or Builder.Discover 7.49 exceptional acres across three separate lots, nestled on Lois Lane—a quiet, private dead-end road just off Old West Road in the historic town of Arlington.A driveway is already in place, guiding you to a secluded potential homesite tucked deep into nature.As you enter Lois Lane, Lot #3 sits

Kristin Comeau

TPW Real Estate

(802) 613-0403

0 Lois Ln Unit 5045700, Arlington, VT 05250
/38
$650,000
- 3 Beds
- 2.5 Baths
- 2,184 Sq Ft
359 Hickory Hill Rd, Bennington, VT 05201

Welcome to this beautifully updated Center Hall Colonial, privately set on 2.58 wooded acres at the end of a peaceful cul-de-sac just minutes from downtown and major highways. The three bedroom, two and half bath home is truly move in ready, offering the perfect balance of comfort, style, and privacy. Step inside to an open concept main level where the kitchen flows seamlessly into the

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 633-6530

359 Hickory Hill Rd, Bennington, VT 05201
/11
$185,000
- 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
/60
$2,750,000
- 4 Beds
- 7.5 Baths
- 8,586 Sq Ft
384 Riverbend Dr, Manchestr Ctr, VT 05255

Exceptional Furnished, this residence is a "Stand Out" Ramsey Gourd, architect designed, coveted River Road area 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

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 300-3969

384 Riverbend Dr, Manchestr Ctr, VT 05255
/20
$750,000
- 4 Beds
- 5 Baths
- 6,650 Sq Ft
338 Main St, Bennington, VT 05201

Don't miss your opportunity to own one of the area's most prestigious properties. The "Marble Bank" is located at the intersection of US Route 7 and Vermont Route 9 and is currently the landmark Fiddlehead Gallery. This property offers unique and grand architecture to go along with its high visibility location. Downtown's redevelopment and thriving new businesses make this location even more

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 347-6655

338 Main St, Bennington, VT 05201
/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
$1,450,000
- 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
/4
$279,000
- 4 Beds
- 4 Baths
- 2,080 Sq Ft
123 Bradford St, Bennington, VT 05201

4 unit apartment building with great rental history and income. Front and back porches and balcony. Great location. Showings to begin 6/10/2024

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 210-1728

123 Bradford St, Bennington, VT 05201
/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
$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
/37
$219,000
- 3 Beds
- 1 Bath
- 1,156 Sq Ft
261 Sycamore Ln, Shaftsbury, VT 05262

Welcome to 261 Sycamore Lane, Shaftsbury, VT!Nestled in a desirable neighborhood, this charming Cape Cod style home is a perfect fit for first-time homebuyers or those looking to downsize into something more manageable. Set of 0.35 acres, the home offers 3 bedrooms and 1 full bath, with added convenience of a first-floor bedroom and bath.Enjoy a spacious backyard perfect for pets, kids,

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 278-9491

261 Sycamore Ln, Shaftsbury, VT 05262
/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
$499,900
- 3 Beds
- 2 Baths
- 1,520 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
/43
$119,900
- Land
- 26 Acres
- $4,665 per Acre
0000 Skiparee Rd, Pownal, VT 05261

Gorgeous 25.7 acre parcel on a dead end road in Pownal, Vermont. This wooded lot offers many possibilities for a home site. Across a stream and up the logging road there is a large clearing that would offer great privacy, with the mountain behind you and great views to the south and east. A lot of opportunity for outdoors activities, homesteading, livestock and gardening. This lot makes the world

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 392-2133

0000 Skiparee 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
/27
$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
/59
$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
/49
$949,000
- 4 Beds
- 3.5 Baths
- 2,700 Sq Ft
681 Powderhorn Rd, Manchester Center, VT 05255

Enjoy privacy and convenience in this charming New England country home, just minutes from town. An open floor plan connects the updated country kitchen to the dining area and living room which features a fireplace and beamed cathedral ceiling. A large mud room with built in storage benches and a farmhouse sink has doors to the stone patio. In the living room, french doors open to a screened

Christiane Carroccio TPW Real Estate

681 Powderhorn Rd, Manchester Center, VT 05255
/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
/51
$1,600,000 Open Sun 11AM - 1PM
- 4 Beds
- 4.5 Baths
- 4,541 Sq Ft
33 Jamie Ln, Bondville, VT 05340

Exceptional Log Home tucked away in the beautiful Green Mountains of Vermont. Welcome to 33 Jamie Lane a 12 acre sanctuary minutes to Stratton Mountain Resort. This extraordinary property offers true privacy surrounded by woods and nature. Features three finished levels of dramatic living space with floor to ceiling windows , soaring stone fireplace, and cherry floors. Open concept kitchen/dining

Cynthia Mitrani Berkshire Hathaway HomeServices Stratton Home

33 Jamie Ln, Bondville, VT 05340
/22
$795,000
- 4 Beds
- 5.5 Baths
- 3,463 Sq Ft
185 Crooked Path Rd, Arlington, VT 05250

A Turnkey Vermont Escape in Picturesque ArlingtonWelcome to your dream getaway nestled in the heart of the Green Mountains—a beautifully appointed 4-bedroom, 5.5-bathroom estate offering the perfect blend of rustic charm and modern luxury. Each spacious bedroom features its own private en-suite bath, providing ultimate comfort and privacy for family and guests. The open-concept kitchen is

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

185 Crooked Path Rd, Arlington, VT 05250
/35
$799,000
- 3 Beds
- 2.5 Baths
- 2,230 Sq Ft
5 Linscott Rd Unit 56, Jamaica, VT 05343

This irresistible renovated Forest Farms contemporary with 3 bedrooms and 2 1⁄2 baths has an inviting ambiance as well as appealing floor plan flow. Past the foyer with half bath is the open living concept with white oak hardwood floors. The glow and warmth of the raised hearth stone fireplace in the living area is shared from windowed dining area to bright kitchen with all new appliances, new

Diana Stugger Four Seasons Sotheby's Int'l Realty

5 Linscott Rd Unit 56, Jamaica, VT 05343
/48
$2,095,000
- 4 Beds
- 3.5 Baths
- 2,654 Sq Ft
5491 Vt Route 315, Rupert, VT 05776

Set on 5+ peaceful acres with stream frontage and panoramic mountain views, this fully renovated 1909 Federal offers timeless character with a like-new feel—just 2.5 miles from the Dorset Green and dining but away from the bustle. Every inch of the main home has been meticulously updated with premium materials and workmanship. A custom walnut kitchen with high-end built in appliances with island

Annette Gallo Real Broker LLC

5491 Vt Route 315, Rupert, VT 05776
/58
$1,600,000
- 4 Beds
- 4 Baths
- 3,441 Sq Ft
53 Old County Rd E Unit 15, Londonderry, VT 05148

Welcome to Landgrove, one of Vermont’s most charming and vibrant communities! This magnificent property offers end-of-road privacy, a luxurious top-to-bottom renovation 2015-2018, the quintessential (and essential) “finished” barn, and 29 acres of beautifully landscaped gardens, grounds and handsome woods awaiting your adventures. This one-of-a-kind property is immaculate, turnkey, and ready for

Claudia Harris Mary Mitchell Miller Real Estate

53 Old County Rd E Unit 15, Londonderry, VT 05148
/36
$1,790,000
- 4 Beds
- 3 Baths
- 2,139 Sq Ft
1949 South Rd, Peru, VT 05152

Nestled in a serene and picturesque setting, Berry Hill Farm offers a rare opportunity to own an exceptional Vermont estate blending charm, versatility, and natural beauty. Spanning 15.52 acres across two separately deeded lots, the property combines inspired design with modern comfort. At its heart is a beautifully crafted contemporary home featuring three spacious bedrooms, sunlit living

Helen Nault Wohler Realty Group

1949 South Rd, Peru, VT 05152
/60
$1,375,000
- 3 Beds
- 4 Baths
- 3,967 Sq Ft
393 Red Tail Ln, Dorset, VT 05251

Stunning contemporary design with elevated mountain views, three bedrooms, four bathrooms, on 11.52 secluded acres in Dorset Hollow. Many recent improvements including: propane baseboard heat, mini-splits for a/c, kitchen redesign, and screened in porch. This home offers an open floor plan with floor to ceiling windows, wood burning fireplace, access to rear sundeck, and wonderful unobstructed

David Halligan Four Seasons Sotheby's Int'l Realty

393 Red Tail Ln, Dorset, VT 05251
/32
$705,000
- 4 Beds
- 2.5 Baths
- 2,408 Sq Ft
22 Bromley Forest Rd, Bondville, VT 05340

Open House Sunday July 6, 10-12. Welcome to your dream Vermont home—where space, light, and location come together in perfect harmony. This beautifully upgraded 4-bedroom residence, complete with a versatile bonus room, features an open-concept living area designed for comfort and connection.The kitchen is a standout, featuring an ILVE 30-Inch Majestic II Dual Fuel Range with 5 Sealed Brass

Carrie Mathews Winhall Real Estate

22 Bromley Forest Rd, Bondville, VT 05340
/59
$699,000
- 3 Beds
- 2.5 Baths
- 3,637 Sq Ft
272 Oak Hill Rd, Shaftsbury, VT 05262

Built in 2001, this stunning contemporary home sits on just under 8 peaceful acres and offers a perfect blend of space, light, and comfort. The grand two-story living room features soaring ceilings and a cozy pellet stove, creating an impressive focal point. The first floor offers a spacious primary suite for ultimate convenience, along with a dedicated home office—perfect for remote work or

Faith Rhodes Maple Leaf Realty

272 Oak Hill Rd, Shaftsbury, VT 05262
/47
$795,000
- 10 Beds
- 6 Baths
- 5,493 Sq Ft
6311 Vt Route 7a, Arlington, VT 05250

The Ira Allen House is nestled in the Battenkill Valley of Southern Vermont and features 420 feet of frontage on the Battenkill River, renowned worldwide for its exceptional trout fishing and ideal for a dip on a hot, steamy day, canoeing and kayaking. This beautiful property sits on over ten acres and boasts antique floors, original hand-hewn beams and many other antique gems as the tavern

Edward Jones Josiah Allen Real Estate, Manchester Branch Office

6311 Vt Route 7a, Arlington, VT 05250
/34
$949,000
- 3 Beds
- 3 Baths
- 3,037 Sq Ft
725 Wideawake Rd, Manchester Center, VT 05255

I am writing to provide you with details about a thoughtfully renovated and maintained custom Cape Cod style home.This home offers approximately 3,000 square feet of living space, including three bedrooms plus an additional room for guests, and three bathrooms. The first floor features a spacious master en suite with a walk-in closet, French doors leading to a patio, and a beautifully

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

725 Wideawake 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.