Bennington County VT Homes for Sale

/30
$1,300,000
- 11 Beds
- 9 Baths
- 9,560 Sq Ft
3309 3321 Main St, Manchester, VT 05254

A Rare Opportunity! Introducing a historically significant gem, available for the first time in over 40 years. Set in the picturesque and highly sought after Manchester Village, this timeless estate includes a grand Main House and a charming Carriage House, each situated on its own adjoining 1.27-acre lot, totaling an expansive 2.54 park-like acres. Together, the residences offer 11 bedrooms, 6

Gregory Cutler Four Seasons Sotheby's Int'l Realty

3309 3321 Main St, Manchester, VT 05254
/26
$585,000
- 4 Beds
- 2.5 Baths
- 2,448 Sq Ft
2 Spruce High Rd, Winhall, VT 05340

Nestled in the desirable Vermont Ventures development, this stunning barn-style home blends rustic charm with modern comfort. Featuring soaring cathedral ceilings with exposed beams, the spacious open-concept kitchen, living, and dining areas are bathed in natural light, creating a warm and inviting atmosphere. Step outside to a large private deck with a hot tub—perfect for relaxing or

Carrie Mathews Winhall Real Estate

2 Spruce High Rd, Winhall, VT 05340
/45
$495,000
- 3 Beds
- 2.5 Baths
- 3,924 Sq Ft
410 Tudor Rd, Arlington, VT 05250

Triple Mountain Views! The wrap-around decks and expansive views will impress any nature lover. This home offers hardwood floors, Vermont marble countertops, and an abundance of windows and light paired with interesting architectural design. Around every turn, you will be surprised by space and contemporary architecture. Re-built in 2011, offering two bedrooms and three baths with a walk-out

Margretta Fischer Wohler Realty Group

410 Tudor 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
/47
$399,000
- 5 Beds
- 3.5 Baths
- 3,600 Sq Ft
46 Duffy Dr, Bennington, VT 05201

This spacious 5-bedroom, 4-bath Colonial in Bennington's sought-after Maplewood neighborhood offers over 3,600 sq ft of flexible living space, including a finished walk-out in-law suite with full kitchen and private entry. Thoughtfully updated with granite counters, stainless steel appliances, and a smart home system including ADT security, glass break sensors, and a smart thermostat. The vaulted

Nick Sicard EXP Realty

46 Duffy Dr, Bennington, VT 05201
/22
$139,000
- 4 Beds
- 1 Bath
- 1,262 Sq Ft
101 Morgan St, Bennington, VT 05201

Motivated seller.!!! Move in asd add your finishing touches to this Antique House located in Downtown on a generous corner. This 2 story, 4 bedroom, 1 bath Bennington home has great character featuring a Dutch front door, enclosed front porch, and beautiful bay window. Property has an eat-in kitchen, dinning room, laundry room with washer and dryer, living room, basement, and den! Enjoy being

Dan Mason Perrott Realty

101 Morgan St, Bennington, VT 05201
/41
$524,900
- 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

Ann Greenwood Alton + Westall Real Estate Agency, LLC

245 Southshire Dr, Bennington, VT 05201
/53
$595,000
- 4 Beds
- 2.5 Baths
- 2,456 Sq Ft
23 Mechanic St, North Bennington, VT 05257

Modern Comfort Meets Historic Charm in North Bennington, VermontNestled within the heart of North Bennington's National Historic District, this thoroughly modern and light-filled home offers the perfect blend of timeless character and contemporary living. Situated on a beautifully landscaped 0.69-acre lot, the property includes a private backyard with ample space for perennial and vegetable

Kelley Mccarthy Mahar McCarthy Real Estate

23 Mechanic St, North Bennington, VT 05257
/18
$549,900
- 3 Beds
- 3.5 Baths
- 1,888 Sq Ft
14 Vaughn Farm Rd Unit 4, Manchester Center, VT 05255

Breathtaking views of Mt Equinox from this completely updated 3 bedroom 4 bath condominium just minutes from town and the ski mountains. The top floor features a fully renovated kitchen with new cabinets, granite countertops and new windows that feature views of a lovely birch tree amidst your own patio and garden. The spacious living room features a deck with mountain views, cathedral ceilings

Sean Dillon Four Seasons Sotheby's Int'l Realty

14 Vaughn Farm Rd Unit 4, Manchester Center, VT 05255
/37
$1,100,000
- 5 Beds
- 4.5 Baths
- 3,697 Sq Ft
1589 Richville Rd, Manchester Center, VT 05255

Welcome to your dream Vermont retreat. This classic 3 bedroom Colonial is gracefully set on 9.52 acres of open meadows with direct frontage on the Battenkill River, renowned worldwide for its exceptional trout fishing. With timeless architecture, peaceful privacy, and sweeping Mountain views, this property captures the essence of New England living. Inside, the home blends historic charm with

Carol O`Connor Four Seasons Sotheby's Int'l Realty

1589 Richville Rd, Manchester Center, VT 05255
/57
$2,429,000
- 7 Beds
- 6.5 Baths
- 6,358 Sq Ft
349 Kent Hill Rd, Dorset, VT 05251

Located in the heart of Dorset Village, just a short walk to the town green, this stunning 7-bedroom, 7-bath residence, built in 1928, is a rare find. Set on 4 hill top acres, the property exudes timeless elegance, blending the charm of its historic roots with thoughtful modern updates. Inside, you will discover a captivating blend of warmth and sophistication. The gourmet kitchen, the heart of

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

349 Kent Hill Rd, Dorset, VT 05251
/21
$299,000
- 3 Beds
- 1.5 Baths
- 1,365 Sq Ft
339 Chester Knoll Dr, Bennington, VT 05201

A completely renovated gem in a fantastic location awaits its new owner. This beautifully restored cape-style home in Bennington's desirable Chester Knoll community offers a stunning and worry-free living experience. Adhering to the newest Vermont energy codes, this energy-efficient home boasts an Energy Star propane heating system for optimal comfort and savings.Chester Knoll provides an

Lori Hurley Four Corner Properties LLC

339 Chester Knoll Dr, Bennington, VT 05201
/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
/59
$599,000
- 4 Beds
- 2 Baths
- 1,828 Sq Ft
69 Hillvale Dr, Manchester Center, VT 05255

This is a wonderful craftsman style ranch in a great location right in the heart of Manchester, in the sunny Hillvale neighborhood. It offers views to Mt. Equinox and is walking access to all Manchester's amenities. Four bedrooms, two full baths, updated kitchen with stainless appliances and granite counter tops, the dining room's french door opens on to an expansive deck for BBQ's and

Robert Sabol Wohler Realty Group

69 Hillvale Dr, Manchester Center, VT 05255
/26
$289,900
- 3 Beds
- 1.5 Baths
- 1,576 Sq Ft
519 South St, Bennington, VT 05201

Welcome to this beautifully maintained 3-bedroom, 1.25-bath home nestled on a corner lot in Bennington. This inviting property blends classic charm with thoughtful updates, offering comfort and style both inside and out.Step into the spacious kitchen featuring stunning wood cabinetry, granite countertops, and a functional island with a bar sink-perfect for entertaining or everyday living. The

Kelley Mccarthy Mahar McCarthy Real Estate

519 South St, Bennington, VT 05201
/27
$1,300,000
- 2 Beds
- 1 Bath
- 1,056 Sq Ft
233 Squires Rd, Manchester Center, VT 05255

Discover a rare opportunity to live and work amidst the serene beauty of Manchester, Vermont. This fully renovated 2-bedroom, 1-bath contemporary ranch, with leased solar array, is nestled on nearly 19 acres, offering a harmonious blend of modern comfort and entrepreneurial potential.The open-concept design features a spacious kitchen and living area, complemented by energy-efficient

Mark Triller Real Broker LLC

233 Squires Rd, Manchester Center, VT 05255
/46
$425,000
- 3 Beds
- 3 Baths
- 1,728 Sq Ft
4 Bank St, Bennington, VT 05201

Across from the 5th Fairway of the Mount Anthony Country Club you’ll find this charming, meticulously maintained 3 bedroom 2 bath home. The spacious open layout, custom kitchen, and expansive deck are warm and inviting. Relax on your front porch and enjoy the scenic mountain vistas of Mount Anthony and the Bennington Monument. Fabulous, convenient location! The home began as a bungalow, the

Margretta Fischer Wohler Realty Group

4 Bank St, Bennington, VT 05201
/51
$2,100,000
- 5 Beds
- 3.5 Baths
- 4,630 Sq Ft
3407 Main St, Manchester, VT 05254

A rare offering in the heart of Manchester Village, 3407 Main Street is a distinguished Georgian-style estate that exemplifies timeless elegance and refined country living. Set on over three private acres of landscaped grounds, this grand residence is a harmonious blend of classic architectural beauty and modern sophistication. Built in 1988 with meticulous attention to scale and symmetry, the

Christiane Carroccio TPW Real Estate

3407 Main St, Manchester, VT 05254
/9
$27,500
- Land
- 1.20 Acres
- $22,917 per Acre
0 Bergrucken Ln Unit 5044034, Stamford, VT 05352

Trade city sirens for wind-rustled maples on this gently wooded 1.2-acre lot tucked inside Alpenwald Village. Alpenwald, although deed restricted, the light protective covenants keep the area tidy without cramping your architectural imagination. Think A-Frame, modern farmhouse, or a passive solar cottage. Beyond the lot is access to trails that lace through the Green Mountain National Forest.

Kelly Agrillo Southern Vermont Realty Group

0 Bergrucken Ln Unit 5044034, Stamford, VT 05352
/55
$325,000
- 3 Beds
- 1.5 Baths
- 1,664 Sq Ft
93 Pace Rd, Bennington, VT 05201

Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about

Harvey Roettinger RE/MAX North Professionals

93 Pace Rd, Bennington, VT 05201
/34
$525,000
- 3 Beds
- 3 Baths
- 1,696 Sq Ft
104 Johnny Cake Hill Ln, Readsboro, VT 05350

If you've been dreaming of peaceful country living with stunning views, this one-of-a-kind home on approximately 22 private acres in the hills of Southern Vermont is calling your name. Greet each morning with an awe-inspiring easterly panorama that, on clear days, stretches all the way to Mount Monadnock.This serene retreat offers the best of nature — birdsong in the morning, occasional

Monica Sumner BHG Masiello Brattleboro

104 Johnny Cake Hill Ln, Readsboro, VT 05350
/31
$1,593,000
- 5 Beds
- 5 Baths
- 6,200 Sq Ft
951 Rupert Rd, Arlington, VT 05250

Discover peace and privacy on this scenic Sandgate, Vermont retreat near the New York border. Nestled on 67 acres of unspoiled land, it’s ideal for families, outdoor enthusiasts, and animal lovers—blending natural beauty with comfortable living.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
/31
$379,000
- 4 Beds
- 2 Baths
- 1,809 Sq Ft
366 Clough Rd, Stamford, VT 05352

Southern Vermont country home, right over the border of Berkshire County, MA. Centrally located between major ski areas in Vermont and MA this home is also just a short drive to all cultural attractions in Berkshire County (MassMoCA, The Clark, Hancock Shaker Village). Bordering the North Branch of the Hoosic River, the property offers river frontage and expansive views of the beautiful Green

Debra Burchard OLD COUNTY PROPERTIES

366 Clough Rd, Stamford, VT 05352
/39
$2,950,000
- 8 Beds
- 8.5 Baths
- 6,471 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
/52
$2,285,000
- 5 Beds
- 4.5 Baths
- 4,647 Sq Ft
543 Lower Hollow Rd, Dorset, VT 05251

A Serene Dorset Hollow Retreat Along the Mettowee RiverTucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you—fall asleep each night to its calming presence. Multiple outdoor spaces include a

Britt Wohler Wohler Realty Group

543 Lower Hollow Rd, Dorset, VT 05251
/33
$365,000
- 3 Beds
- 1.5 Baths
- 1,666 Sq Ft
379 Swallow Hill Rd, Pownal, VT 05261

Welcome home! Tucked away on over 2.6 private and partially wooded acres in the exclusive and tight-knit Swallow Hill neighborhood, this stunning 3-bedroom, 1.5-bath home offers modern comfort and rustic charm in a serene natural setting in Southern Vermont.Step inside to soaring cathedral ceilings, exposed wood beams, and an abundance of Vermont beauty pouring in through large windows.

Cassie Barbeau Mahar McCarthy Real Estate

379 Swallow Hill Rd, Pownal, VT 05261
/7
$399,000
- 4 Beds
- 2 Baths
- 1,368 Sq Ft
72 Mckee Rd, Arlington, VT 05250

There is a charming 1985 Cape Cod style home situated on 2.4 acres that is now available.The property boasts a kitchen with a cathedral ceiling, a comfortable living room, and two bedrooms all conveniently located on the first floor. Upstairs, you'll find an additional two bedrooms and a bathroom. The home also includes a full unfinished basement, offering potential for future expansion or

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

72 Mckee Rd, Arlington, VT 05250
/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
/50
$419,000
- 3 Beds
- 3.5 Baths
- 1,730 Sq Ft
46 Willows Way Unit 5, Peru, VT 05152

Freshly painted 46 Willows Way unit 5 in Bromley Village! This townhouse offers 3 bedrooms, 4 bathrooms plus the loft, mudroom, large deck with views and storage area. Three levels, end unit has wonderful southern views, and it is located within a short walk to the Lord's Prayer Ski Slope. The first-floor features large living room, kitchen and dining area and 1/2 Bathroom. The living room has

Tatsiana Clark Four Seasons Sotheby's Int'l Realty

46 Willows Way Unit 5, Peru, VT 05152
/50
$398,900
- 5 Beds
- 4 Baths
- 3,400 Sq Ft
927 Water St, North Bennington, VT 05257

Stately North Bennington Colonial with In-Law Suite & Barn on 2.6 Acres.Step into timeless elegance in this beautifully crafted colonial-style home located in the heart of charming North Bennington. Offering 5 spacious bedrooms and 4 bathrooms, this home features a flexible floor plan that includes a private in-law suite, formal living and dining rooms, a welcoming foyer, and both front and

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

927 Water St, North Bennington, VT 05257
/58
$269,000
- 7 Beds
- 4 Baths
- 4,417 Sq Ft
200 Depot St, Bennington, VT 05201

Own a piece of Bennington history! Alex Drysdale House, c. 1850. The grocery store (formerly 138 River Street) operated under the name "A. Drysdale & Son" and was built in 1876. Today this historic property is set up as a four-unit with great income potential. It currently houses three apartments: a freshly renovated four bedroom (used as an Airbnb), three bedroom, and efficiency, along with the

Justine Curry Maple Leaf Realty

200 Depot St, Bennington, VT 05201
/57
$215,000
- 3 Beds
- 1 Bath
- 1,416 Sq Ft
100 Webb St, Bennington, VT 05201

Enchanted Historic Home with Storybook Charm – A Hidden Gem Near Downtown!Step into a fairytale in this one-of-a-kind, lovingly maintained home — a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort.From the moment you arrive, you're greeted by the

Lindsey Martin Maple Leaf Realty

100 Webb St, Bennington, VT 05201
/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
/11
$780,000
- Land
- 664 Acres
- $1,175 per Acre
0 W Sandgate Rd, Sandgate, VT 05250

This remarkable, partially conserved property is a true gem for conservation-minded buyers and outdoor enthusiasts alike. Encompassing two watersheds and a stretch of the pristine Green River, the land offers a rich tapestry of natural features and diverse terrain—ideal for exploring, observing wildlife, and enjoying every season to its fullest. The landscape ranges from gently rolling meadows to

Andy Reed Four Seasons Sotheby's Int'l Realty

0 W Sandgate Rd, Sandgate, VT 05250
/50
$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
/28
$379,000
- 4 Beds
- 2 Baths
- 1,920 Sq Ft
84 Jasper Ln, Arlington, VT 05250

Immaculate Cape on a Quite dead end road. New metal roof. Tilt in windows.Whole house exhaust fan. Flooring--hardwood, laminate and tile. Great family house. Move in condition. Nothing to do but move in. Basement set up for a work shop.Leach field is shared

Charles Mauro Josiah Allen Real Estate, Inc.

84 Jasper Ln, Arlington, VT 05250
/43
$1,525,000
- 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
/27
$375,000
- Land
- 53 Acres
- $7,075 per Acre
0 Rock Bottom Ln, Peru, VT 05152

Discover the perfect canvas for your dream retreat on this stunning 53-acre parcel in picturesque Peru, Vermont. Tucked away in the Green Mountains, this exceptional property offers expansive views—including a breathtaking sightline to Magic Mountain—and the serenity of true Vermont wilderness.A private driveway is already in place, making access simple and setting the stage for your

David Shehadi Josiah Allen Real Estate, Inc.

0 Rock Bottom Ln, Peru, VT 05152
/41
$1,549,000
- 4 Beds
- 4 Baths
- 4,266 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
/35
$264,900
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
115 Jefferson Ave, Bennington, VT 05201

Located in a charming Bennington neighborhood, this home offers both convenience and comfort, with shopping, schools, the post office, and the hospital just a short distance away. The welcoming three-season front porch is perfect for enjoying your morning coffee or winding down after a long day. Inside, the spacious, eat-in kitchen has brand-new flooring and newer appliances, adding a fresh and

Kelley Mccarthy Mahar McCarthy Real Estate

115 Jefferson Ave, Bennington, VT 05201

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