Bennington County VT Homes for Sale with Garage

/59
$2,800,000
- 3 Beds
- 3.5 Baths
- 3,938 Sq Ft
23 Valley View Rd, Winhall, VT 05340

Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

Kim Morgan-Wohler Wohler Realty Group

23 Valley View Rd, Winhall, VT 05340
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/53
$399,000
- 5 Beds
- 3 Baths
- 2,568 Sq Ft
100 McCarthy Acres, North Bennington, VT 05257

Almost lake front! Come for the space, stay for the location! This 2,500+ sq. ft. home offers five bedrooms, three full bathrooms, a large home office in the finished basement, and an additional 250 sq. ft. bonus room off one of the upstairs bedrooms. The owners converted the original garage into a 600 sq. ft. primary bedroom (heated and cooled with an efficient mini-split and separated into a

Nicholas Charest Maple Leaf Realty

100 McCarthy Acres, North Bennington, VT 05257
/28
$1,700,000
- 4 Beds
- 3.5 Baths
- 2,363 Sq Ft
43 Middle Ridge Rd Unit 415, Winhall, VT 05155

Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

Edwin Kevil Stratton Real Estate

43 Middle Ridge Rd Unit 415, Winhall, VT 05155
/53
$625,000
- 3 Beds
- 2 Baths
- 1,894 Sq Ft
190 Vt Route 11 Unit 1, Peru, VT 05152

Don't miss the opportunity to own this renovated 4 bedroom/ 2 full bath townhouse in Peru, VT. This tasteful and high end renovation will wow you. Combining the ambiance and character of a European mountain Chalet with the amenities and style of a contemporary mountain residence, this offers beautiful tiled luxury bathrooms and gourmet kitchen. The great room has vaulted wood beamed ceilings,

Robert Sabol Wohler Realty Group

190 Vt Route 11 Unit 1, Peru, VT 05152
/25
$475,000
- 3 Beds
- 2 Baths
- 1,460 Sq Ft
393 Morse Hill Rd, East Dorset, VT 05253

This beautifully maintained home is now available for the first time in 40 years.On the main level, you will find a generously sized eat-in kitchen with granite countertops that opens to a dining room. There are two additional rooms on the main level: a large living room and a bedroom. The main floor also boasts French door that leads out to a spacious deck, perfect for overlooking the

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

393 Morse Hill Rd, East Dorset, VT 05253
/36
$498,000
- 3 Beds
- 2 Baths
- 1,671 Sq Ft
6 Dwyers Camp Rd, Shaftsbury, VT 05262

Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior,

Lori Hurley Four Corner Properties LLC

6 Dwyers Camp Rd, Shaftsbury, VT 05262
/42
$439,000
- 4 Beds
- 1.5 Baths
- 1,728 Sq Ft
639 Wiley Mountain Rd, Readsboro, VT 05350

Updated mountain home on 13.63 flat, usable acres bordering the Green Mountain National Forest and offering an outdoor paradise in every season. Tucked at the top of a quiet road, this property blends comfort, space, and access to Vermont’s best year-round recreation.Inside, you’ll find new hardwood floors, a renovated kitchen and bathrooms, a main-level bedroom, a full bath, main-level

Melissa Nebelski Skihome Realty

639 Wiley Mountain Rd, Readsboro, VT 05350
/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 and a half 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,

Diana Stugger Four Seasons Sotheby's Int'l Realty

5 Linscott Rd Unit 56, Jamaica, VT 05343
/31
$259,000
- 2 Beds
- 1 Bath
- 836 Sq Ft
473 South Rd, East Arlington, VT 05252

This is an exceptional opportunity at this price point as a starter home for individuals or young families. This quaint craftsman home sits in the town of Sunderland and is the ideal location situated between Manchester and Bennington, Vermont. It is a 2.5 mile drive to the village of Arlington. This location boasts School Choice for families, to include Burr and Burton Academy. A mudroom

Robert Sabol Wohler Realty Group

473 South Rd, East Arlington, VT 05252
/45
$3,600,000
- 4 Beds
- 3.5 Baths
- 2,338 Sq Ft
198 Church St, Dorset, VT 05251

Nestled in the heart of the iconic Dorset village, just steps from the Dorset Field Club and the beloved local theater, this enchanting historic home has been meticulously renovated, rejuvenated, and reimagined with no expense spared. From the moment you arrive, the home's timeless charm and thoughtful updates are evident. A complete reengineering of the roof and replacement of all major systems

Adrienne Sherwood Four Seasons Sotheby's Int'l Realty

198 Church St, Dorset, VT 05251
/33
$445,000
- 3 Beds
- 2.5 Baths
- 1,777 Sq Ft
8920 Sage Hill Rd Unit 20, Manchester, VT 05255

Nestled amidst the breathtaking scenery, this 3 bedroom condominium offers an idyllic escape. Inside, you're greeted by an open living space on the main floor, featuring high ceilings, natural woodwork and a wood-burning fireplace. The kitchen is spacious and flows into the dining/living area. On the main floor you'll also find the primary bedroom, full bathroom, half bath, and enclosed three

David Halligan Four Seasons Sotheby's Int'l Realty

8920 Sage Hill Rd Unit 20, Manchester, VT 05255
/32
$675,000
- 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
/33
$820,000
- 4 Beds
- 3 Baths
- 2,317 Sq Ft
0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

Beautifully updated Piper Ridge townhouse just steps from the private sports center and offering weekend/holiday shuttle service to Stratton’s lifts in winter. This light-filled home features an updated kitchen and baths, gleaming hardwood floors, and elegant tilework throughout. The one-car garage has been thoughtfully converted into a spacious ski room plus a large storage or owner’s

Carrie Mathews Winhall Real Estate

0 Maple Ridge Rd Unit B-2, Winhall, VT 05340
/59
$679,000
- 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
/38
$565,000
- 4 Beds
- 3 Baths
- 2,073 Sq Ft
2588 Vermont 11, Peru, VT 05152

On a gentle rise surrounded by 7.5 acres of meadows and woodland, this Vermont style ranch subtly blends an appealing rustic charm with contemporary features. The current owners purchased the property in 2021 for family and friends and installed a new wastewater system, new furnace, new roof section, new appliances. The rough sawn clapboard exterior delineates the enduring character of the house.

Diana Stugger Four Seasons Sotheby's Int'l Realty

2588 Vermont 11, Peru, VT 05152
/41
$750,000
- 3 Beds
- 2.5 Baths
- 2,716 Sq Ft
55 Uphill Rd, Landgrove, VT 05148

The advantage of end of the road privacy on 18 acres in charming Landgrove. This beautiful contemporary offers generously sized rooms with over 2700 sq ft and a perfect Vermont floor plan. Easy entry from the large 2 car garage into the mud room area, and right into the kitchen with it's expansive counter space and cozy sitting area with propane stove for those cool winter mornings. The

Brian Gehlich RE/MAX Four Seasons

55 Uphill Rd, Landgrove, VT 05148
/31
$799,000
- 3 Beds
- 3 Baths
- 2,317 Sq Ft
9 F Cobble Ridge Rd, Winhall, VT 05340

Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy

Carrie Mathews Winhall Real Estate

9 F Cobble Ridge Rd, Winhall, VT 05340
/25
$305,000
- 3 Beds
- 2.5 Baths
- 1,888 Sq Ft
120 Albe Dr, Bennington, VT 05201

Comfortable, convenient and close to downtown Bennington and all its amenities. Built in 2001, in a quiet neighborhood, the home features 3 bedrooms and 2.5 baths,, which includes a primary suite with its own bath. The first floor offers a spacious eat-in kitchen with washer and dryer efficiently installed in a large closet. The kitchen also has glass doors that open to private deck and a level

Ann Greenwood Alton + Westall Real Estate Agency, LLC

120 Albe Dr, Bennington, VT 05201
/45
$355,000
- 4 Beds
- 1 Bath
- 1,680 Sq Ft
19 Royal St, North Bennington, VT 05257

Charming North Bennington Home in a Desirable Neighborhood.Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College.Step inside to discover a freshly

Lindsey Martin Maple Leaf Realty

19 Royal St, North Bennington, VT 05257
/54
$1,995,000
- 3 Beds
- 2.5 Baths
- 3,451 Sq Ft
139 Prospect St, Manchester, VT 05254

Step into Vermont’s rich history with this beautifully reimagined 3 bedroom, 3,451 sq ft home in the heart of Manchester Village, just steps from over 900 acres of scenic trails at the base of Equinox Mountain. Originally built in 1934 as a historic residence, the home offers a rare blend of timeless character and modern comfort. A marble walkway leads to classic Dutch doors, while a peaceful

Katherine Zilkha Four Seasons Sotheby's Int'l Realty

139 Prospect St, Manchester, VT 05254
/38
$1,995,000
- 5 Beds
- 3 Baths
- 4,959 Sq Ft
2589 W Sandgate Rd, Arlington, VT 05250

Two Pigs Farm is a hillside retreat in Southern Vermont's Taconic Range, where meadows are bound by ancient maple trees, stone walls and two clear brooks. The circa 1989 farmhouse and barns feel timeless—rooted, quietly graceful—designed for comfort, and connection. Inspired by childhood summers in Sandgate, the owner dreamed of a place where time stretches—mornings for berry picking, afternoons

Dia Jenks LandVest, Inc/Woodstock

2589 W Sandgate Rd, Arlington, VT 05250
/23
$4,000,000
- 5 Beds
- 2 Baths
- 3,347 Sq Ft
15 Wind Hill Rd, Manchester Center, VT 05255

At the heart of this remarkable 136-acre property in Manchester Center, Vermont, are two distinct historic homes, each telling a story of the land’s deep roots in the Beattie-Forrest family, who have stewarded it for over a century.The original farmhouse, built circa 1800, offers five bedrooms and two baths, with timeless details including a vintage kitchen and hand-hewn timber framing.

Paul Carroccio TPW Real Estate

15 Wind Hill Rd, Manchester Center, VT 05255
/34
$500,000
- 1 Bed
- 2 Baths
- 300 Sq Ft
417 Maple Hill Rd, Arlington, VT 05250

Scandinavian Timber Frame Tiny House & Grindbygg! Over 10 acres of privacy and beautiful vistas. 360 degree mountain view from this custom heartfelt build. The property includes a one bedroom tiny house complete with kitchen, gas range, wood stove, movie projector, sleeping loft and so much more. A drilled well, on demand propane hot water heater and water shed for water storage. This cozy

Margretta Fischer Wohler Realty Group

417 Maple Hill Rd, Arlington, VT 05250
/31
$150,000
- 3 Beds
- 1 Bath
- 1,508 Sq Ft
109 Evergreen Dr, Bennington, VT 05201

House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front

Zachary Zupan EXP Realty

109 Evergreen Dr, Bennington, VT 05201
/41
$499,900 Open Fri 1PM - 3:30PM
- 4 Beds
- 2.5 Baths
- 2,116 Sq Ft
245 Southshire Dr, Bennington, VT 05201

Nestled in one of Bennington's most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm--all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System(BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious

Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

245 Southshire Dr, Bennington, VT 05201
/50
$425,000
- 3 Beds
- 2 Baths
- 1,941 Sq Ft
97 Buck Hill Rd, Shaftsbury, VT 05262

Two homes on 4.67 acres in Shaftsbury, VT! This village home offers a rare opportunity indeed by including a separate 2 bedroom ranch home as well. The main home is a charming New England farmhouse with 3 bedrooms and 2 bathrooms, living room, formal dining room, kitchen, main level laundry and so much more. The accessory dwelling unit offers 2 bedrooms, 1 bathroom, eat-in kitchen and living

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

97 Buck Hill Rd, Shaftsbury, VT 05262
/37
$679,000
- 3 Beds
- 2 Baths
- 2,070 Sq Ft
68 Owls Nest Cir Unit B-7, Manchester, VT 05254

Equinox on the Battenkill, is one of Southern Vermont’s premier condominium resort communities. Located in the historic Village of Manchester, nestled at the base of Mt. Equinox and situated along the acclaimed Equinox Golf Course and Battenkill River. One of it's gems, 68 Owls Nest Circle, has opened up and is priced to sell! Fresh interior and exterior paint and new windows. This charming 3

Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

68 Owls Nest Cir Unit B-7, Manchester, VT 05254
/31
$1,495,000
- 5 Beds
- 5 Baths
- 5,000 Sq Ft
951 Rupert Rd, Arlington, VT 05250

Discover peace and privacy on this scenic Sandgate, Vermont estate near the New York border. Nestled on 67 acres of unspoiled land, it’s ideal for outdoor enthusiasts, or those seeking to get away from it all, yet centrally located to modern amenities. Tucked down a long private drive, the home evokes a Scottish countryside manor. The spacious layout features a first-floor primary suite with two

Kristin Pirie KW Vermont Woodstock

951 Rupert Rd, Arlington, VT 05250
/39
$2,800,000
- 8 Beds
- 8.5 Baths
- 4,075 Sq Ft
69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155

This extraordinary Stratton Mountain Retreat, just minutes to the slopes, offers glorious long range views and a very private setting. This impressive home was masterfully constructed in 2009 and includes a separate barn, 11.55 acres of land, 2 covered porches, a built in barbecue and an outdoor fireplace, hot tub and fire pit.The main level of the home features a Gourmet Kitchen, grand

Sara Buckley Josiah Allen Real Estate, Inc.

69 Upper Taylor Hill Rd Unit D, Winhall, VT 05155
/37
$1,700,000
- 6 Beds
- 7 Baths
- 5,400 Sq Ft
2001 Depot St, Manchester Center, VT 05255

Experience the best of Vermont living at Greybourne House, a fully furnished and impeccably maintained estate offering four-season enjoyment. With 6 bedrooms, 7 full bathrooms, and over 5,400 square feet of living space on 3.2 private acres, this home combines comfort, elegance, and an unbeatable location just minutes from Bromley, Stratton, and the dining and shopping of Manchester. A grand

Steven Bryant TPW Real Estate

2001 Depot St, Manchester Center, VT 05255
/42
$1,950,000
- 9 Beds
- 7 Baths
- 6,956 Sq Ft
1086 West Rd, Bennington, VT 05201

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

Chris DeFelice Four Seasons Sotheby's Int'l Realty

1086 West Rd, Bennington, VT 05201
/49
$4,875,000
- 7 Beds
- 10 Baths
- 7,422 Sq Ft
318 Spring Hill Ln, Dorset, VT 05251

Welcome to a truly exceptional estate where classic charm and modern craftsmanship unite on 9 secluded acres in the heart of coveted Dorset, Vermont. Meticulously curated with no detail overlooked and no expense spared, this remarkable property features a beautifully renovated 1941 Colonial residence, complemented by a collection of newer luxury companion buildings that together create a one of a

Richard Slocum Four Seasons Sotheby's Int'l Realty

318 Spring Hill Ln, Dorset, VT 05251
/48
$599,900
- 4 Beds
- 3.5 Baths
- 3,742 Sq Ft
34 Southshire Dr, Bennington, VT 05201

Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all

Kelley Mccarthy Mahar McCarthy Real Estate

34 Southshire Dr, Bennington, VT 05201
/42
$799,000
- 4 Beds
- 3.5 Baths
- 3,188 Sq Ft
308 Mending Walls Rd, Manchester Center, VT 05255

NEW ROOF, 2022! NEW MOUND SYSTEM! NEW WATER FILTER SYSTEM! CHIMNEY HAS LINER! NEW NEUTRAL INTERIOR PAINT! LIGHT FILLED, WALK OUT BASEMENT!Come see this immaculate Country Cape located in the highly sought-after community of Mending Walls in Manchester, Vermont. This well-maintained 2003 home combines timeless charm with modern convenience, offering a perfect blend of cozy living and spacious

Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

308 Mending Walls Rd, Manchester Center, VT 05255
/43
$1,495,000
- 5 Beds
- 4.5 Baths
- 4,219 Sq Ft
7 Timberbrook N, Dorset, VT 05251

Modern Elegance Surrounded by Mountain Serenity. Stunning 5-bedroom, 4.5-bath home nestled on nearly 2 acres, just minutes from Dorset Green and Manchester Village. Blending modern design with traditional warmth, the property features energy-efficient geothermal heating & cooling and solar power. Expansive windows and French doors frame mountain views, the deck is perfect for entertaining. The

Margretta Fischer Wohler Realty Group

7 Timberbrook N, Dorset, VT 05251
/41
$1,449,000
- 4 Beds
- 4 Baths
- 2,736 Sq Ft
693 Longview Dr, Manchester, VT 05255

Tucked away in one of Manchester's most scenic neighborhoods, this 4-bedroom, 4-bathroom home offers peace,privacy,and thoughtful updates on three beautifully landscaped acres.Mature trees, immaculately crafted stone walls, a flowing brook,and expansive level lawn spaces create a true Vermont retreat.Centrally located near the town center and 1.5 miles from Burr and Burton Academy,you get the

Tara van de Velde Four Seasons Sotheby's Int'l Realty

693 Longview Dr, Manchester, VT 05255
/25
$1,274,999
- 4 Beds
- 2.5 Baths
- 4,620 Sq Ft
139 Village View Rd, Manchester, VT 05255

Enjoy privacy and panoramic views of Mount Equinox and the Manchester Valley from this spacious, light-filled home in a desirable location. The main level features a vaulted great room, eat-in kitchen with adjacent covered porch, dining room, den with fireplace, two bedrooms, a full bath, and a primary suite with walk-in shower and jetted tub. Step out onto the expansive deck and take in the

Marek Kovac TPW Real Estate

139 Village View Rd, Manchester, VT 05255
/52
$199,000
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
130 Morgan St, Bennington, VT 05201

200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities.

Dan Mason Perrott Realty

130 Morgan St, Bennington, VT 05201
/40
$1,800,000
- 5 Beds
- 4.5 Baths
- 3,436 Sq Ft
59 Church St, Dorset, VT 05251

Exceptional Dorset Church St. offering. Spacious c 1850s Italianate with Greek Revival features in remarkable condition with new roof, windows, refinished floors, A/C. Spacious, bright eat-in kitchen large parlor living room with fireplace, dining room. First floor master suite, bright well-appointed eat-in kitchen and updated bathrooms. 4-5 bedrooms, Large level yard, stone walled terraces

R. Diedrich August Wohler Realty Group

59 Church St, Dorset, VT 05251
/58
$1,550,000
- 5 Beds
- 3 Baths
- 4,342 Sq Ft
93 Hard Farm Rd, Manchester Center, VT 05255

EARTH WIND AND SHIREHaving caught your breath from the view in the approach, and treading the elegant slate path into the home, you probably won't want to get past the "basking parlor", a room designed for sheer joy in the present moment, made compelling by the wall of windows and the perfectly proportioned design and vaulted ceiling. However, the delights in every room beckon: next is the

Lawrence Zupan EXP Realty

93 Hard Farm Rd, Manchester Center, VT 05255

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