Bennington County VT Homes for Sale

/43
$275,000
- 3 Beds
- 2 Baths
- 1,422 Sq Ft
277 Union St, Bennington, VT 05201

Enchanting, delightful, magical... this lovely c. 1920 village home is all of that and more! 3BR/2BA home has beautiful hardwood floors and a cook's kitchen with Corian countertops and not one but two pantries! Dining room, living room with electric fireplace, office/study that could also be a first floor bedroom and updated 3/4 bath round out the first floor. Upstairs there is the primary

Vicki Wilson

Maple Leaf Realty

(802) 588-8535

277 Union St, Bennington, VT 05201
/34
$349,900
- 3 Beds
- 2 Baths
- 2,354 Sq Ft
290 Springhill Rd, Bennington, VT 05201

Contemporary style 3BR/2BA home in a lovely residential neighborhood not far from downtown Bennington! Kitchen has been updated with granite counters and stainless appliances and opens onto sunny dining area. Living room includes brick hearth with woodstove and shiplap ceiling, there is first floor laundry and a three-quarter bath as well as an expansive family room with lots of natural light.

Vicki Wilson

Maple Leaf Realty

(802) 300-3742

290 Springhill Rd, Bennington, VT 05201
/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
/15
$550,000
- 6 Beds
- 2 Baths
- 5,878 Sq Ft
972 Vt Route 7a, Shaftsbury, VT 05262

MIXED USE INVESTMENT PROPERTY boasts two rental apartments and first floor retail space. The “Shaftsbury Country Store Building” on Historic Route 7A has stood the test of time. This landmark building dates back to 1850, when 10% of Vermont’s population was destined to serve in the Union Army and fight in the Civil War. The back apartment is on the second and third floors with a large deck

Kristin Comeau

TPW Real Estate

(802) 988-7626

972 Vt Route 7a, Shaftsbury, VT 05262
/13
$225,000
- 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) 213-9746

2017 East Rd, Shaftsbury, VT 05262
/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
$1,750,000
- 4 Beds
- 4.5 Baths
- 4,891 Sq Ft
430 Riverbend Dr, Manchester Center, VT 05255

Tasteful Grace... Timeless Style... Easy Comfort... Manchester's River Road leads to this Extraordinary 4900 SF Riverbend Residence embracing the most impactful Green Mountain views from every room with window walls that bring the outdoors in. The casual open flow floorplan transitions flawlessly over hardwood floors taking in abundant architectural detail from deep crown moldings, custom

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 481-3816

430 Riverbend Dr, Manchester Center, VT 05255
/40
$875,000
- 4 Beds
- 3 Baths
- 3,607 Sq Ft
3357 Main St, Manchester, VT 05254

Historic Manchester Village... Lovingly restored mid-1800s residence holds court on this beautiful street with lantern-lined marble sidewalks and underground utilities. Walk to all area amenities, from numerous dining options to Equinox Pond hikes and various sports such as golf, tennis, paddle, and cross-country skiing. This two-story-expanded colonial offers lovely light, architectural details,

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 636-5833

3357 Main St, Manchester, VT 05254
/4
$298,000
- 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
/41
$399,000
- 2 Beds
- 2 Baths
- 2,294 Sq Ft
4690 Route 153, Rupert, VT 05776

This very special Vermont Contemporary is perched above the road on 10+ beautiful acres of gardens and park-like forest. The property is located on the east side of VT Rte 153 in Rupert, an unspoiled northwest corner of Bennington County. Start your day enjoying sunrise in the breakfast sunroom for morning coffee or tea, and enjoy the evening light on the west-facing screen porch listening to

Kristin Comeau

TPW Real Estate

(802) 487-8165

4690 Route 153, Rupert, VT 05776
/4
$225,000
- 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
/47
$65,000
- Land
- 10 Acres
- $6,250 per Acre
210 Sparrow Dr, Stamford, VT 05352

Wonderful 10.4+/- acre lot with views of Black Poll, Spruce and Greylock mountains. Located in the small southern Vermont town of Stamford. Sparrow is a quite residential drive maintained year-round by the town. The property slopes up from the road, offering several potential homes sites with very nice views to the southeast. The seller recently had the lot soil tested for septic capacity and

Curtis Trousdale Preferred Properties

210 Sparrow Dr, Stamford, VT 05352
/24
$39,000
- Land
- 7 Acres
- $5,540 per Acre
170 Gore Rd, Bennington, VT 05201

7.04 +/- Acres of beautiful open woodland, gently sloping and surrounded by stone walls. A perfect spot for a little get-a-way, camping, tenting, hunting but with future potential for a home. Access is via a deeded 50’ ROW off a paved town road. This ROW is about 800’ long. It would likely be simple to create a parking area and walk or ATV out to the property for recreational purposes. In

Curtis Trousdale Preferred Properties

170 Gore Rd, Bennington, VT 05201
/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
$795,000
- 2 Beds
- 2 Baths
- 3,478 Sq Ft
142 Mount Aeolus Rd, Manchester, VT 05255

A Rare Investment Opportunity in Manchester! This versatile property offers the perfect blend of commercial and residential potential, making it an ideal choice for savvy investors or those seeking a live-work setup. The upstairs features a spacious residential rental, while the lower level was recently leased to a local daycare, providing immediate rental income.This well-maintained property

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

142 Mount Aeolus Rd, Manchester, VT 05255
/50
$1,375,000
- 4 Beds
- 5 Baths
- 3,610 Sq Ft
3360 Dorset Rd W, Dorset, VT 05251

Exceptional Dorset Contemporary with Classic Craftsmanship & Modern ComfortsSet on 1.86 peaceful acres abutting Dorset Field Club property, this beautifully maintained four-bedroom, five-bath contemporary home offers privacy, elegance, and an ideal Vermont lifestyle. Surrounded by nature and just moments from Dorset Village, this property blends timeless design with thoughtful updates, perfect

David Halligan Four Seasons Sotheby's Int'l Realty

3360 Dorset Rd W, Dorset, VT 05251
/60
$1,100,000
- 6 Beds
- 5 Baths
- 5,298 Sq Ft
50 Stratton View Rd, Winhall, VT 05340

Custom built six-bedroom home on 2 acres with spectacular views of Stratton Mountain. The kitchen has granite countertops and custom cabinets with the dining area nearby with plenty of space to accommodate a large gathering. The living area has a cathedral ceiling with large windows for an abundance of natural light and stunning year-round views of Stratton Mountain, with a lovely stone fireplace

Mike England Michael England Real Estate

50 Stratton View Rd, Winhall, VT 05340
/26
$677,000
- 4 Beds
- 3 Baths
- 2,560 Sq Ft
3 Stratton Ridge Rd, Winhall, VT 05340

This spacious four-bedroom, three-bathroom home is perfectly situated just minutes away from the Stratton base lodge, making it an ideal Vermont vacation retreat. The home offers plenty of convenience and comfort, with a mudroom providing ample space for all your ski gear. Two of the bedrooms feature en-suite bathrooms, and there's a cozy loft area, perfect for unwinding with a good book or

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

3 Stratton Ridge Rd, Winhall, VT 05340
/48
$685,000
- 3 Beds
- 2.5 Baths
- 1,738 Sq Ft
1516 W Mountain Rd, Shaftsbury, VT 05262

Discover your dream retreat in this immaculate 3-bedroom, 3-bath, single level home, nestled on over 4 acres of breathtaking landscape. Enjoy expansive mountain views of the Taconic range, Bennington Monument, and Mount Graylock. Relax on the spacious deck or in the screened-in porch, soaking in the stunning vistas. This updated one-level home, features hardwood floors throughout and an open

Margretta Fischer Wohler Realty Group

1516 W Mountain Rd, Shaftsbury, VT 05262
/28
$1,475,000
- 4 Beds
- 2.5 Baths
- 4,634 Sq Ft
1677 Barnumville Rd, Manchester Center, VT 05255

This historic 19th century two-story brick Federal house was originally a popular tavern. It has been completely renovated/updated to serve today's relaxed living while retaining all classic features. A bright kitchen/dining/living great room w/fireplace is the heart of the home. A first-floor master suite includes a spa-like bath w/fireplace. There is an adjacent mudroom entrance with 1/2 bath

R. Diedrich August Wohler Realty Group

1677 Barnumville Rd, Manchester Center, VT 05255
/59
$1,200,000
- 3 Beds
- 3.5 Baths
- 4,054 Sq Ft
4 Garden Loop Rd, Winhall, VT 05340

Your Stratton Mountain retreat awaits! This beautiful turnkey mountain home just off the Stratton Mountain Road is the perfect location for family gatherings, ski trips, hiking and more. This three-bedroom, three-bath home on three levels includes a breathtaking great room with a stone fireplace and vaulted ceilings. Dining room and additional breakfast area next to the kitchen. A large open

Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

4 Garden Loop Rd, Winhall, VT 05340
/28
$799,000
- 4 Beds
- 3 Baths
- 3,676 Sq Ft
5 Stratton Ridge Rd, Winhall, VT 05340

Discover the ultimate Vermont ski retreat, just 2 miles from Stratton Mountain. This captivating home offers breathtaking mountain views across three spacious levels. The upper level features a private primary suite with a newly renovated bath and a cozy loft/office space — your peaceful sanctuary. The heart of the home, the main level, is perfect for gathering, with soaring cathedral ceilings,

Carrie Mathews Winhall Real Estate

5 Stratton Ridge Rd, Winhall, VT 05340
/37
$675,000
- 9 Beds
- 8.5 Baths
- 4,995 Sq Ft
722 Main St, Bennington, VT 05201

Imagine owning the oldest home in downtown Bennington full of history and amazing detail. Built by Joseph Safford after opening Bennington's first Grist Mill, then fully renovated during the Italianate Victorian area for much of it's current design. This historic Inn along the Walloomsac River is now being used as an Air BnB rental as well as a separate leased 2 bedroom apartment. The Fully

Lilli West Maple Leaf Realty

722 Main St, Bennington, VT 05201
/27
$1,650,000
- 2 Beds
- 2.5 Baths
- 1,799 Sq Ft
1424 West Rd, Manchester Center, VT 05255

Luxurious Guest House on 16.9 Acres with Unmatched Views and Custom Features. Nestled on nearly 17 acres of pristine land off Manchester West Road, this high-end guest house offers breathtaking panoramic views of the Green Mountains and Mt. Equinox. Designed with a perfect blend of comfort and elegance while you build you dream home, the home features custom carpentry throughout, showcasing

Andy Reed Four Seasons Sotheby's Int'l Realty

1424 West Rd, Manchester Center, VT 05255
/35
$649,000
- 8 Beds
- 3.5 Baths
- 2,520 Sq Ft
405 Vermont 30, Winhall, VT 05340

Ski Resort Investment Gem! 2-Family Home Near Stratton & BromleyRare investment opportunity in the heart of Vermont's premier ski region. Located on scenic Vermont Route 30, this property offers unparalleled access to both Stratton Mountain Resort and Bromley Mountain Ski Resort. Whether you're looking to live in one unit and rent the other, or convert it to a single-family home, this

Robin Apps Four Seasons Sotheby's Int'l Realty

405 Vermont 30, Winhall, VT 05340
/25
$875,000
- 4 Beds
- 3.5 Baths
- 5,700 Sq Ft
56 Mending Walls Rd, Manchester Center, VT 05255

A lovely cape/farmhouse located in the desirable Mending Walls Subdivision. A light, bright, spacious, 4 bedroom, 3.5 bath, beautifully updated home, boasting high end appliances, beautiful wood floors, two master suites, one on first floor with separate entrance so could be in law suite/au pair room, screened in porch, finished basement with lots of storage space. Living room with fireplace,

Derek Greene Derek Greene

56 Mending Walls Rd, Manchester Center, VT 05255
/37
$699,999
- 4 Beds
- 3 Baths
- 3,504 Sq Ft
636 Tunnel St, Readsboro, VT 05350

Almost there! This owner has taken a traditional farmhouse and transformed it into an amazing home full of style and grace. There are many ways to consider this home...over 3500 square feet of single family living with 4 bedrooms (or even 5) and 3 baths...live on one floor, AIR B&B all or part of the other floor....rent both levels and use as a vacation home on off seasons. The kitchen is

Christine Lewis Brattleboro Area Realty

636 Tunnel St, Readsboro, VT 05350
/28
$750,000
- 3 Beds
- 2 Baths
- 2,610 Sq Ft
3622 Dorset West Rd, Dorset, VT 05251

Unique Dorset West Road offering....This rare opportunity beckons creativity, craft, and charm! Begs all those ready, willing and able to renovate, keeping the existing home, whilst enjoying life in an extremely beautiful and desirable location. Enjoy the beautiful framed in mountain views from most interior living spaces and from the back patio/yard. This 6.6 acre rolling property boasts

Sunny Breen Josiah Allen Real Estate, Inc.

3622 Dorset West Rd, Dorset, VT 05251
/36
$875,000
- 4 Beds
- 3 Baths
- 2,797 Sq Ft
13 Betty Johnson Ln, Bondville, VT 05340

Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening. With two distinct living areas, you'll find the ideal spaces for

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

13 Betty Johnson Ln, Bondville, VT 05340
/28
$825,000
- 5 Beds
- 2 Baths
- 3,500 Sq Ft
20 Bishop Rd, Searsburg, VT 05363

Absolutely amazing long range mountain views over the Green Mountain National Forest, Mount Snow, Haystack, and Stratton, from this beautiful 2020 Moosehead log home. This home sits on 7+ acres with easy access to VAST snowmobile trails, as well as your own property to loop on, but still only a short drive to ski resorts, lakes, and other Vermont destinations. The home has a gorgeous open floor

Adam Palmiter Berkley & Veller Greenwood/Dover

20 Bishop Rd, Searsburg, VT 05363
/34
$550,000
- 3 Beds
- 2.5 Baths
- 1,872 Sq Ft
764 Barnumville Rd Unit 1, Manchester Center, VT 05255

Rustic charm meets modern comfort. Fully renovated barn-style condo in an incredible settingWelcome to a one-of-a-kind barn-style condominium that blends timeless craftsmanship with modern updates, set against the breathtaking backdrop of Vermont's Green Mountains. This fully renovated 3 bedroom, 3 bath home is anything but ordinary, offering character, quality, and convenience in one stunning

Lisa Sullivan Four Seasons Sotheby's Int'l Realty

764 Barnumville Rd Unit 1, Manchester Center, VT 05255
/42
$310,000
- 2 Beds
- 2 Baths
- 1,624 Sq Ft
516 Oberdorf Rd, Readsboro, VT 05350

Outdoor lover’s paradise in Alpenwald Village! This beautifully updated 2-bedroom, 2-bath home sits on an ample 2.5 acres and abuts National Forest land—perfect for year-round adventure. Step inside to your open kitchen and a bright family room with cathedral ceilings and a sliding door that opens to a peaceful back porch with stunning mountain views. The spacious mudroom offers plenty of room

Lindsey Martin Maple Leaf Realty

516 Oberdorf Rd, Readsboro, VT 05350
/6
$35,000
- Land
- 1.70 Acres
- $20,588 per Acre
159 Oberdorf Rd, Readsboro, VT 05350

Escape to the mountains with this ready-to-build 1.7-acre lot in scenic Alpenwald Village! Nestled beside National Forest land and bordered by a charming brook along the northern edge, this property offers a peaceful natural setting with endless outdoor adventure at your doorstep. Enjoy direct access to VAST snowmobile and VASA ATV trails, nearby hiking and mountain biking, and Dutch Hill for

Lindsey Martin Maple Leaf Realty

159 Oberdorf Rd, Readsboro, VT 05350
/29
$339,000
- 3 Beds
- 2 Baths
- 1,362 Sq Ft
297 Mad Tom Rd, East Dorset, VT 05253

Adorable Cape-style gem nestled beside the enchanting Mad Tom Brook. This bright and sunny 1.5-story home captures the essence of Vermont living, natural beauty, timeless charm, and thoughtfully updated comfort. Step inside to discover a charming interior that blends classic New England character with modern upgrades. The newly updated kitchen is appointed with elegant soapstone countertops and

Sandy Reavill Real Broker LLC

297 Mad Tom Rd, East Dorset, VT 05253
/47
$299,900
- 4 Beds
- 2.5 Baths
- 2,404 Sq Ft
120 Imperial Ave, Bennington, VT 05201

Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

Kelley Mccarthy Mahar McCarthy Real Estate

120 Imperial Ave, Bennington, VT 05201
/15
$180,000
- Land
- 37 Acres
- $4,865 per Acre
2793 Rupert Rd, Arlington, VT 05250

Tucked away in the quiet hills of Sandgate, Vermont—where the population is fewer than 500 kindred spirits—this rare 37-acre parcel offers a retreat into the stillness of nature. A harmonious blend of mature woodlands and thoughtfully cleared meadows, the land invites you to build your dream sanctuary in a place where the wild still whispers.With a state-approved wastewater permit already in

Faith Rhodes Maple Leaf Realty

2793 Rupert Rd, Arlington, VT 05250
/22
$215,000
- 1 Bed
- 1 Bath
- 644 Sq Ft
67 Bourn Brook Rd Unit 55, Manchester Center, VT 05255

Welcome to this beautifully updated one-bedroom upstairs unit that’s move-in ready and packed with value. Freshly painted with stylish vinyl plank flooring throughout, this home shines with natural light and thoughtful upgrades—including brand new kitchen counters and a new hot water tank.Enjoy the ease of low-maintenance living! The association handles trash service, snow removal, exterior

Faith Rhodes Maple Leaf Realty

67 Bourn Brook Rd Unit 55, Manchester Center, VT 05255
/10
$135,000
- Land
- 5 Acres
- $26,892 per Acre
0- Stratton View Rd, Winhall, VT 05340

Stratton View Road lives up to its name. Big Views of Stratton, just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Own your piece of Vermont.

Mike England Michael England Real Estate

0- Stratton View Rd, Winhall, VT 05340
/9
$65,000
- Land
- 0.74 Acre
- $87,838 per Acre
0 Stratton View Rd, Winhall, VT 05340

Stratton View Rd Lot # 58 , .74 +- acres wooded parcel. Just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Addition Lot MLS #5036984 available. Own your piece of Vermont.

Mike England Michael England Real Estate

0 Stratton View Rd, Winhall, VT 05340

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