Bennington County, VT Homes

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  /45

  $340,000

  • 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 renovated

  Lindsey Martin Maple Leaf Realty

  19 Royal St, North Bennington, VT 05257
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  /50

  $1,275,000 Sold Sep 05, 2025

  • 3,610 Sq Ft
  • $353/SF
  • 79 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1960

  3360 Dorset Rd W, Dorset, VT 05251

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

  David Halligan Four Seasons Sotheby's Int'l Realty

  3360 Dorset Rd W, Dorset, VT 05251
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  /35

  Est $821,219 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft

  290 Mending Walls Rd, Manchester Center, VT 05255

  290 Mending Walls Rd, Manchester Center, VT 05255
• 

  

  

  /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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  /2

  $1,600,000 Sold Sep 05, 2025

  • 3,441 Sq Ft
  • $465/SF
  • 11 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1997

  53 Old County Rd E Unit 15, Londonderry, VT 05148

  Welcome to Landgrove, one of Vermont’s most charming and vibrant communities! This magnificent property offers end-of-road privacy, a luxurious top-to-bottom renovation 2015-2018, the quintessential (and essential) “finished” barn, and 29 acres of beautifully landscaped gardens, grounds and handsome woods awaiting your adventures. This one-of-a-kind property is immaculate, turnkey, and ready for

  Claudia Harris Mary Mitchell Miller Real Estate

  53 Old County Rd E Unit 15, Londonderry, VT 05148
• 

  

  /28

  Est $761,545 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,955 Sq Ft

  182 Mending Walls Rd, Manchester Center, VT 05255

  182 Mending Walls Rd, Manchester Center, VT 05255
• 

  

  /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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  /28

  $398,350 Sold Sep 04, 2025

  • 1,620 Sq Ft
  • $246/SF
  • 0 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2025

  315 Chester Knoll Dr, Bennington, VT 05201

  This stunning new construction home offers the perfect blend of modern efficiency and serene natural surroundings. Located in a highly desirable neighborhood, this energy-efficient home is a testament to quality craftsmanship and thoughtful design.Step inside to an open-concept living space flooded with natural light. The main level flows seamlessly to a spacious deck, where you'll enjoy

  Lilli West Maple Leaf Realty

  315 Chester Knoll Dr, Bennington, VT 05201
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  /26

  Est $625,804 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,924 Sq Ft

  989 Beech St, Manchester Center, VT 05255

  989 Beech St, Manchester Center, VT 05255
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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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  /60

  $1,369,000 Sold Sep 04, 2025

  • 3,967 Sq Ft
  • $345/SF
  • 12 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1987

  393 Red Tail Ln, Dorset, VT 05251

  Stunning contemporary design with elevated mountain views, three bedrooms, four bathrooms, on 11.52 secluded acres in Dorset Hollow. Many recent improvements including: propane baseboard heat, mini-splits for a/c, kitchen redesign, and screened in porch. This home offers an open floor plan with floor to ceiling windows, wood burning fireplace, access to rear sundeck, and wonderful unobstructed

  David Halligan Four Seasons Sotheby's Int'l Realty

  393 Red Tail Ln, Dorset, VT 05251
• 

  

  /31

  Est $603,564 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,177 Sq Ft

  350 Carlen St, Manchester Center, VT 05255

  350 Carlen St, Manchester Center, VT 05255
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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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  /60

  $2,150,000 Sold Sep 04, 2025

  • 4,975 Sq Ft
  • $432/SF
  • 36 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1983

  341 Danby Mountain Rd, Dorset, VT 05251

  Spectacular Dorset 24 acre Architect Designed Estate conveniently located 1.3 miles from the Dorset Green boasting level stone walled perennial gardens, meadows and woodlands, water ways and pond with established walking paths meandering throughout this compound creating ideal indoor - outdoor transitions to be embraced quietly amongst song birds and completely away from all hustle and bustle!

  Laura Beckwith Josiah Allen Real Estate, Inc.

  341 Danby Mountain Rd, Dorset, VT 05251
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  /40

  Est $722,552 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,564 Sq Ft

  190 Meadow Ridge Rd, Manchester Center, VT 05255

  190 Meadow Ridge Rd, Manchester Center, VT 05255
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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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  /37

  $256,250 Sold Sep 03, 2025

  • 1,259 Sq Ft
  • $204/SF
  • 7 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1940

  1236 Morgan St, Bennington, VT 05201

  Charming and solid 1940s Cape with detached 2-car garage. On the outskirts of town with 0.63 acres, this property has a rural vibe, but only 1.2 miles from Main Street... enjoy both the quiet and convenience! Large rear deck overlooks the backyard and is a welcome entryway to the sunny breakfast nook and kitchen. All appliances are staying, including the washer/dryer in the basement. Dining

  Jenifer Prouty Hoffman Hoffman Real Estate

  1236 Morgan St, Bennington, VT 05201
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  /24

  Est $777,245 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,903 Sq Ft

  268 Meadow Ridge Rd, Manchester Center, VT 05255

  268 Meadow Ridge Rd, Manchester Center, VT 05255
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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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  /49

  $245,000 Sold Sep 03, 2025

  • 864 Sq Ft
  • $284/SF
  • 28 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1959

  130 Sycamore Ln, Shaftsbury, VT 05262

  Looking for easy living on a quiet, dead-end street in a desirable neighborhood? Look no further! This one level ranch has all you need. Sitting on a nice-sized yet manageable lot, this two bedroom home has been meticulously maintained from top to bottom. The furnace was replaced only a year ago, so heating costs have been low for the current owners. Great news for Vermont winters! The bedrooms

  Justine Curry Maple Leaf Realty

  130 Sycamore Ln, Shaftsbury, VT 05262
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  /26

  Est $718,569 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,124 Sq Ft

  373 Hillcrest Rd, Manchester Center, VT 05255

  373 Hillcrest Rd, Manchester Center, VT 05255
• 

  

  /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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  /32

  $170,000 Sold Sep 03, 2025

  • 1,155 Sq Ft
  • $147/SF
  • 66 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1993

  106 Park St Unit 1, Bennington, VT 05201

  Welcome to Unit #1 at Norton Potters, a quaint and quiet townhouse community nestled in a lovely neighborhood setting. This end-unit two-bedroom home is full of character and natural light, offering a peaceful retreat with a deck that overlooks a serene stream.The main level features a spacious living room, dining area, kitchen with a generous pantry, a convenient half bath, and laundry

  Faith Rhodes Maple Leaf Realty

  106 Park St Unit 1, Bennington, VT 05201
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  /36

  Est $562,052 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft

  64 Mears Ln, Manchester Center, VT 05255

  64 Mears Ln, Manchester Center, VT 05255
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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
• 

  

  /19

  $225,000 Sold Aug 29, 2025

  • Land
  • 16.68 Acres
  • $13,489 per Acre

  • 34 Days On Market

  1801 S Stream Rd, Bennington, VT 05201

  Welcome to 1801 South Stream Road a picturesque 16.68 acres of timeless Vermont charm property. This beautiful parcel features two classic Vermont red barns full of character and charm, that offer endless potential. With some repairs, they could be ideal for livestock, storage, or workshop space ready to support your vision for country living. A picturesque pond, in need of a little TLC, offers

  Brooke Thomson Drew Mahar McCarthy Real Estate

  1801 S Stream Rd, Bennington, VT 05201
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  /26

  Est $583,497 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,182 Sq Ft

  84 Green Mountain Rd, Manchester Center, VT 05255

  84 Green Mountain Rd, Manchester Center, VT 05255
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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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  /59

  $1,082,500 Sold Aug 29, 2025

  • 4,054 Sq Ft
  • $267/SF
  • 45 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2005

  4 Garden Loop Rd, Winhall, VT 05340

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

  Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

  4 Garden Loop Rd, Winhall, VT 05340
• 

  

  /23

  Est $554,051 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,664 Sq Ft

  70 Hillcrest Rd, Manchester Center, VT 05255

  70 Hillcrest 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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  /37

  $219,000 Sold Aug 29, 2025

  • 1,156 Sq Ft
  • $189/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  261 Sycamore Ln, Shaftsbury, VT 05262

  Welcome to 261 Sycamore Lane, Shaftsbury, VT!Nestled in a desirable neighborhood, this charming Cape Cod style home is a perfect fit for first-time homebuyers or those looking to downsize into something more manageable. Set of 0.35 acres, the home offers 3 bedrooms and 1 full bath, with added convenience of a first-floor bedroom and bath.Enjoy a spacious backyard perfect for pets, kids,

  Brooke Thomson Drew Mahar McCarthy Real Estate

  261 Sycamore Ln, Shaftsbury, VT 05262
• 

  

  /35

  Est $768,732 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,520 Sq Ft

  2529 Main St, Manchester Center, VT 05255

  2529 Main St, Manchester Center, VT 05255
• 

  

  /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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  /43

  $115,000 Sold Aug 29, 2025

  • Land
  • 25.7 Acres
  • $4,475 per Acre

  • 22 Days On Market

  0000 Skiparee Rd, Pownal, VT 05261

  Gorgeous 25.7 acre parcel on a dead end road in Pownal, Vermont. This wooded lot offers many possibilities for a home site. Across a stream and up the logging road there is a large clearing that would offer great privacy, with the mountain behind you and great views to the south and east. A lot of opportunity for outdoors activities, homesteading, livestock and gardening. This lot makes the world

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  0000 Skiparee Rd, Pownal, VT 05261
• 

  

  /19

  Est $663,448 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,004 Sq Ft

  251 White Birch Ln, Manchester Center, VT 05255

  251 White Birch Ln, Manchester Center, VT 05255
• 

  

  /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
• 

  

  /23

  $525,000 Sold Aug 29, 2025

  • 2,139 Sq Ft
  • $245/SF
  • 5 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1910

  62 Dorset Village Ln, Dorset, VT 05251

  Charming Home in Quaint Dorset Village SettingNestled on a gentle knoll above the heart of Dorset Village, this delightful home offers the perfect blend of privacy and convenience. Just a short stroll to village amenities and mere moments from the renowned Pinnacle hiking trails, the location is ideal for those seeking both community charm and outdoor adventure.Brimming with

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  62 Dorset Village Ln, Dorset, VT 05251
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  /41

  Est $566,139 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,088 Sq Ft

  1565 E Manchester Rd, Manchester Center, VT 05255

  1565 E Manchester Rd, 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

Showing Results 521 - 560, Page 14 of 18