Bennington County VT Houses for Sale

/60
$1,150,000
- 3 Beds
- 3 Baths
- 2,267 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
/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
$699,000
- 4 Beds
- 3.5 Baths
- 5,700 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
/41
$295,000
- 5 Beds
- 2 Baths
- 1,588 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
/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
$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
/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
/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
/39
$275,000
- 3 Beds
- 1.5 Baths
- 1,264 Sq Ft
139 Mckinley St, Bennington, VT 05201

Welcome to 139 McKinley Street in Bennington! This charming 1920 New Englander blends character and convenience in a great village location. Inside, you'll find a first-floor primary bedroom with laundry and a half bath downstairs, a cozy living room with a beautiful woodstove, and hardwood floors upstairs with easy care laminate throughout the main level.A standout feature is the

Brooke Thomson Drew

Mahar McCarthy Real Estate

(607) 437-6795

139 Mckinley St, Bennington, VT 05201
/59
$745,000
- 4 Beds
- 4 Baths
- 4,844 Sq Ft
422 N Mason Hill Rd, Pownal, VT 05261

At the end of a tree lined drive this country Contemporary awaits you, situated on a private 10 acre parcel with stone walls, mature perennials, and a mix of lawn and woods. The main level enjoys an open floor plan, perfect for entertaining; cooks kitchen with gas range, stainless appliances, pantry cabinets as well as a butler's pantry anchors the space. The two-story fieldstone hearth with

Vicki Wilson

Maple Leaf Realty

(802) 483-8151

422 N Mason Hill Rd, Pownal, VT 05261
/35
$359,000
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
33 Aspen Ln, Bondville, VT 05340

Minutes from Stratton Mountain, this cozy chalet offers the perfect mountain escape with timeless character and room to make it your own. Featuring a classic chalet style floor to ceiling stone fireplace and wood interior, this home exudes vintage alpine charm. There are three bedrooms, two baths and an open concept living space, providing plenty of room for gatherings or weekend getaways.

Alison Cummings

Cummings & Co

(802) 424-9210

33 Aspen Ln, Bondville, VT 05340
/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
$895,000
- 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
- 3,333 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
/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
/36
$4,975,000
- 5 Beds
- 4 Baths
- 5,445 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
/55
$1,575,000
- 5 Beds
- 5 Baths
- 4,785 Sq Ft
671 West Rd, Manchester Center, VT 05255

Charming 1790 Manchester Village home with guest house and separate garage located in the heart of Manchester Village and just steps from restaurants, shops, and the Southern Vermont Arts Center. This beautifully maintained 5 bedroom, 3 1/2 bath home sits on 3.8 private acres of expansive lawn, manicured gardens, and outdoor entertaining space. The updated kitchen features a large island, a

Katherine Zilkha Four Seasons Sotheby's Int'l Realty

671 West Rd, Manchester Center, VT 05255
/43
$749,000
- 4 Beds
- 2 Baths
- 1,200 Sq Ft
86 Benson Fuller Dr, Bondville, VT 05340

Your Ultimate GetawayEscape to this idyllic Vermont retreat, where convenience meets relaxation. This spacious home offers everything you need for a fun-filled and carefree lifestyle, from outdoor entertaining to cozy indoor spaces.Step out onto the large deck and unwind by the gas fire pit table, or enjoy watching the friendly mini-golf matches below. In the cooler nights of winter,

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

86 Benson Fuller Dr, Bondville, VT 05340
/52
$775,000
- 4 Beds
- 3.5 Baths
- 4,032 Sq Ft
77 Monument Ave, Bennington, VT 05201

Located in the prestigious Village of Old Bennington, this stately 4,000+ sq. ft. center hall Colonial sits on 1.6 beautifully landscaped acres with a year-round creek and charming footbridge. Thoughtfully maintained, it features updates including electrical, plumbing, new roofing, and rebuilt chimneys. A gracious foyer welcomes you, flanked by a formal parlor with fireplace and half bath,

Moira Spivey Four Seasons Sotheby's Int'l Realty

77 Monument Ave, Bennington, VT 05201
/60
$1,825,000
- 3 Beds
- 4 Baths
- 2,872 Sq Ft
36 Beaver St, Bondville, VT 05340

Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape—crafted for adventure, relaxation, and making lasting memories in every season. Whether you’re hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute

MaryKate Grey Stratton Real Estate

36 Beaver St, Bondville, VT 05340
/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
/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

Kim Morgan-Wohler Wohler Realty Group

1949 South Rd, Peru, VT 05152
/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
/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
/43
$1,550,000
- 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 4.7 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 main

Margretta Fischer Wohler Realty Group

7 Timberbrook N, Dorset, VT 05251
/33
$895,000
- 3 Beds
- 3 Baths
- 3,037 Sq Ft
725 Wideawake Rd, Manchester Center, VT 05255

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 updated bathroom with radiant flooring and a marble shower. Also on the first floor, you'll find a bright and airy kitchen

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

725 Wideawake Rd, Manchester Center, VT 05255
/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
/37
$799,000
- 4 Beds
- 3 Baths
- 3,609 Sq Ft
3357 Main St, Manchester, VT 05254

Situated along one of Manchester Village’s most iconic, tree-lined streets, this impeccably restored mid-19th century Colonial blends timeless charm with modern comfort. Surrounded by marble sidewalks and classic lantern lighting, this exceptional property offers the rare opportunity to live in a storybook setting with walkability to dining, shopping, hiking, and year-round recreational

Annette Gallo Real Broker LLC

3357 Main St, Manchester, VT 05254
/38
$1,200,000
- 5 Beds
- 1 Bath
- 2,228 Sq Ft
395 King Hill Rd, Readsboro, VT 05350

Stunning Mountain & Meadow Views, 135 acres of pristine rolling meadows overlook the Harriman Reservoir, sits a meticulously maintained c. 1770 5 bedroom farmhouse. Welcome to King Hill Farm, this idyllic Vermont homestead has been in the King family for multiple generations. No restrictions, enjoy the peace and quiet of a slight breeze, blue skies and bird songs. Remarkable, one of a kind

Margretta Fischer Wohler Realty Group

395 King Hill Rd, Readsboro, VT 05350
/28
$749,000
- 4 Beds
- 2 Baths
- 2,055 Sq Ft
21 Burnt Hill Rd, Winhall, VT 05341

Welcome to Gone Ski Inn, your cozy, all-season mountain retreat in the heart of Vermont!This charming home features four inviting bedrooms and two well-appointed bathrooms, offering plenty of space to unwind after a day of adventure. In the winter, cozy up by the crackling wood-burning fireplace , toasty wood stove or relax in the soothing hot tub under the stars. With ski trails just

Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

21 Burnt Hill Rd, Winhall, VT 05341
/26
$795,000
- 3 Beds
- 3 Baths
- 2,044 Sq Ft
6 Quarter Mile Rd, Winhall, VT 05340

AMAZING LOCATION! Walking distance to Stratton Mountain! This home is located on the shuttle route and being offered fully furnished! Walk to the slopes or just take a nice walk around the local trails. Spacious home with ample room for everyone. The open concept kitchen, dining, living room offers cathedral ceilings and woodburning fireplace. French doors leading out to the firepit area for

Julie Lowe Lowe's Real Estate, LLC

6 Quarter Mile Rd, Winhall, VT 05340
/33
$880,000
- 8 Beds
- 6 Baths
- 4,326 Sq Ft
143 Nichols Rd, Peru, VT 05152

I am writing to share information about a remarkable property in Peru, Vermont, that offers year-round enjoyment.This sun-filled home is situated on 10 acres of land, boasting beautiful mountain views and a private pond complete with a beach, deck, above-ground pool, and a sauna. Imagine swimming, fishing, and hiking in the warmer months, and ice-skating, snowmobiling, and cross-country

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

143 Nichols Rd, Peru, VT 05152
/28
$825,000
- 4 Beds
- 2 Baths
- 1,068 Sq Ft
6 Roundtree Rd, Winhall, VT 05340

Prime Stratton location! This charming 4-bedroom, 2-bathroom retreat offers vaulted ceilings, an open-concept living area with a wood burning fireplace, and a private deck and backyard for relaxing after a day on the slopes. With weekend and holiday shuttle service during ski season, plus easy access to Stratton Village’s shops, dining, and year-round activities, it’s the ideal spot to recharge

Christina Dryden Berkshire Hathaway HomeServices Stratton Home

6 Roundtree Rd, Winhall, VT 05340
/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
/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
$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
/28
$775,000
- 5 Beds
- 2 Baths
- 3,500 Sq Ft
20 Bishop Rd, Searsburg, VT 05363

Owners motivated and will consider offers. 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 direct 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

Adam Palmiter Berkley & Veller Greenwood/Dover

20 Bishop Rd, Searsburg, VT 05363
/28
$849,000 New Construction
- 3 Beds
- 2.5 Baths
- 1,980 Sq Ft
40 Jameson Flats Unit D, Manchester, VT 05255

New Construction in the Heart of Manchester – Showings Begin April 15This beautifully designed 3-bedroom, 2.5-bath freestanding home (with potential for a 4th bedroom) offers modern comfort, energy efficiency, and fine craftsmanship just steps from downtown Manchester. The open-concept main level features a chef’s kitchen with an eat-in island, ample storage, stainless steel appliances,

Britt Wohler Wohler Realty Group

40 Jameson Flats Unit D, Manchester, 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.