Bennington County VT Homes for Sale

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  /21

  $249,000

  • Land
  • 3.42 Acres
  • $72,807 per Acre

  0 Havoc Hill Unit 29, Dorset, VT 05253

  Tranquility and Adventure Await on Havoc Hill. Discover 3.42 plus private, wooded acres nestled atop storied Havoc Hill in charming East Dorset, Vermont. Known for its beauty and historic ties to early Vermont logging and farming communities, Havoc Hill offers a rare opportunity to own land rich in character and natural serenity. Set off the picturesque Mad Tom Road, this secluded parcel is fully

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  0 Havoc Hill Unit 29, Dorset, VT 05253
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  /40

  $549,000

  • 2 Beds
  • 2 Baths
  • 4,044 Sq Ft

  5515 Main St, Manchester, VT 05255

  Own a piece of Vermont history with this charming 1830s home, perfectly situated on Main Street in downtown. Zoned for mixed use (MU2), this versatile property offers endless possibilities-live, work, or do both in one inspiring space. The 2-bedroom, 2-bath home blends vintage Vermont character with modern comfort, featuring mini-splits for heating and cooling, a propane stove, fiber optic

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  5515 Main St, Manchester, VT 05255
• 

  

  

  /45

  $179,900

  • 4 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  266 Robillard Rd, Stamford, VT 05352

  SOUTHERN VERMONT!~ DRASTIC PRICE DROP! 4 bedroom home in Stamford, Vermont located less than 15 minutes to Mass MoCA In North Adams this country location with over a 1/2 acre of great yard space. Large outdoor back deck, inside sitting porch, kitchen with pantry opens to dining & living room. Oak hardwood floors on 1st & 2nd floors. 4 nice sized bedrooms on 2nd level. 3rd level would make great

  Colleen Zajac MONARCH REALTY, INC.

  266 Robillard Rd, Stamford, VT 05352
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  /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
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  /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

  755 Main St, Bennington, VT 05201
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  /55

  $2,225,000

  • 4 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  16 Hunter Ridge Rd, Bondville, VT 05340

  Custom built Wadsworth Design Build timber-frame mountain retreat blends luxury, craftsmanship, and convenience just minutes from Stratton Mountain Resort. Set on 2.66 acres and spanning 5,000± square feet, this 4-bedroom, 5-bath home includes two additional sleeping space ideal for hosting friends and family. A grand entry framed by oversized Douglas fir posts welcomes you into a lodge style

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  16 Hunter Ridge Rd, Bondville, VT 05340
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  /57

  $1,769,000

  • 5 Beds
  • 4.5 Baths
  • 3,218 Sq Ft

  5491 Vt Route 315, Rupert, VT 05776

  Luxury home, move-in ready, on 5+ peaceful acres with protected panoramic mountain views and stream frontage, 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

  Annette Gallo Real Broker LLC

  5491 Vt Route 315, Rupert, VT 05776
• 

  

  /22

  $895,000

  • Land
  • 24.08 Acres
  • $37,168 per Acre

  A Windsor Rd, Manchester, VT 05255

  Simply Extraordinary! 24.08 Acres with a State Wastewater Permit for 11 Bedrooms that includes 2 buildable lots within the acreage. With unrivaled easterly views, this parcel is the last permitted within what is now the Forest and Recreational/Farming and Rural Residential District of Manchester , Vermont. There will be no further development around this parcel. Abutted by protected lands and

  Kim Morgan-Wohler Wohler Realty Group

  A Windsor Rd, Manchester, VT 05255
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  /36

  $1,790,000

  • 4 Beds
  • 3 Baths
  • 2,545 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
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  /33

  $425,000

  • 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
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  /33

  $799,000

  • 4 Beds
  • 3 Baths
  • 2,317 Sq Ft

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340

  Move in and relax—seller will pay your first year of HOA fees! 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

  Carrie Mathews Winhall Real Estate

  0 Maple Ridge Rd Unit B-2, Winhall, VT 05340
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  /38

  $525,000

  • 4 Beds
  • 3 Baths
  • 2,073 Sq Ft

  2588 Vermont 11, Peru, VT 05152

  PRICE ADJUSTMENT: 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

  Diana Stugger Four Seasons Sotheby's Int'l Realty

  2588 Vermont 11, Peru, VT 05152
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  /34

  $249,900

  • 3 Beds
  • 2.5 Baths
  • 1,810 Sq Ft

  3530 Vt Route 346, Pownal, VT 05261

  This historic house, built in 1880, is nestled in the quiet village of North Pownal. It is situated on a large, level lot and offers the timeless charm of yesteryear. The first floor features a roomy kitchen with Kenmore Plus Stainless-Steel appliances, an open-concept living room and dining room, an updated bathroom, and a convenient first-floor laundry room. The back porch has been partially

  Matt Waddington Hoffman Real Estate

  3530 Vt Route 346, Pownal, VT 05261
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  /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
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  /31

  $749,000

  • 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
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  /19

  $219,500

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft

  14 Robinson Ave, Bennington, VT 05201

  Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

  Timothy Corcoran Mahar McCarthy Real Estate

  14 Robinson Ave, Bennington, VT 05201
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  /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

  303-305 Gage St, Bennington, VT 05201
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  /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
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  /33

  $525,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  3 Strattonwald Rd, Winhall, VT 05340

  Lovingly renovated and move-in ready, this 3-bedroom chalet is your ideal mountain escape in the sought-after Strattonwald neighborhood. Take in beautiful views of Stratton Mountain from the comfort of your home while enjoying the warmth and character of this thoughtfully updated retreat. Inside, you'll find a brand-new kitchen and updated bathroom, stone wood burning fireplace, gleaming hardwood

  Robin Apps Four Seasons Sotheby's Int'l Realty

  3 Strattonwald Rd, Winhall, VT 05340
• 

  

  /22

  $850,000

  • 4 Beds
  • 3 Baths
  • 3,659 Sq Ft

  445 Canterbury Rd, Manchester Center, VT 05255

  Nestled in one of Vermonts most sought-after locations, this exceptional Colonial home boasts sweeping panoramic views of the Green Mountain National Forest and the picturesque Northshire Valley, offering a peaceful and private retreat just minutes from the vibrant town of Manchester. Perfectly oriented to capture stunning morning sunrises, this 2.8-acre property provides the ideal balance of

  Andy Reed Four Seasons Sotheby's Int'l Realty

  445 Canterbury Rd, Manchester Center, VT 05255
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  /45

  $345,000

  • 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
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  /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

  137 Park St, Bennington, VT 05201
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  /10

  $342,000

  • Land
  • 28.5 Acres
  • $12,000 per Acre

  11 Old County Rd E, Londonderry, VT 05148

  A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  11 Old County Rd E, Londonderry, VT 05148
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  /38

  $1,995,000

  • 5 Beds
  • 3 Baths
  • 6,323 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
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  /38

  $860,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Jamaica, VT 05343

  Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape.Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Jamaica, VT 05343
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  /6

  $110,000

  • Land
  • 1 Acre
  • $110,000 per Acre

  88A Sylvan Ridge Rd, Winhall, VT 05340

  Wooded lot with hardwoods, evergreens and birch trees. Potential views of Bromley Mountain and beyond. Town maintained road. Close to VAST snowmobile trails. Build your dream home in the Golden Triangle of ski areas, Stratton, Bromley, and Magic Mountains. Only 10 minuets to Manchester. Available on request:Wastewater System and Potable Water Supply PermitSeptic

  Andrew King Stratton Real Estate

  88A Sylvan Ridge Rd, Winhall, VT 05340
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  /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
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  /10

  $1,950,000

  • Land
  • 7 Acres
  • $278,571 per Acre

  720 N Branch St, Bennington, VT 05201

  Discover the potential at 720 & 702 North Branch Street—a rare 7-acre offering in a prime Bennington location. With level land, generous frontage, and easy access, this property is perfectly positioned for residential or mixed-use development, with municipal water and sewer available at the street.The sale includes a well-maintained duplex at 702 North Branch, featuring a 3-bedroom unit

  Paul Carroccio TPW Real Estate

  720 N Branch St, Bennington, VT 05201
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  /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 a pond and beautiful vistas. Mountain views 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
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  /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
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  /31

  $135,000

  • 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
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  /37

  $625,000

  • 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
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  /27

  $1,200,000

  • 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
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  /9

  $27,500

  • Land
  • 1.2 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
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  /11

  $169,900

  • 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 with a lot of square footage.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  905 County St, Bennington, VT 05201
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  /45

  $1,190,000

  • 6 Beds
  • 7 Baths
  • 5,400 Sq Ft

  2001 Depot St, Manchester Center, VT 05255

  LOCATION, LOCATION: 8 minutes from Bromley, 20 minutes to Stratton, yet close to Manchester restaurants, shopping, fishing, Horse Show & golf. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bathroom retreat offers 5,400+ square feet of living space on 2 private acres—perfect for use as a primary residence, vacation getaway, or a return to its B&B roots.

  Steven Bryant TPW Real Estate

  2001 Depot St, Manchester Center, VT 05255
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  /50

  $374,900

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft

  927 Water St, North Bennington, VT 05257

  Charming Historic Home with Garden, Barn & Flexible Living Spaces This beautiful 100+ year-old home offers over 3,400 sq. ft. of warmth, character, and room to grow. Flooded with natural light, this home on 2+ acres has three sunny upstairs bedrooms and three baths. In addition to a large living room and full dining room, the main floor has a laundry/mudroom and front and rear parlors that can

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  927 Water St, North Bennington, VT 05257
• 

  

  /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
• 

  

  /50

  $4,500,000

  • 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

Showing Results 121 - 160, Page 4 of 6