Bennington County VT Homes for Sale

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  /10

  $245,000

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  209 Grove St Unit 11, Bennington, VT 05201

  Well-maintained 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, an eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice backyard, 2 covered parking spaces

  Julie Glover Mahar McCarthy Real Estate

  209 Grove St Unit 11, Bennington, VT 05201
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  /43

  $2,300,000

  • Land
  • 67 Acres
  • $34,328 per Acre

  215 Vermont 30, Dorset, VT 05251

  Opportunities are Knocking! Welcome to an extraordinary 67-acre estate parcel in Dorset, perfectly positioned along Route 30. This remarkable property offers the ultimate trifecta—location, natural beauty, and limitless potential. Bordering a gentle brook and featuring a mix of rolling meadows and scenic mountain logging trails, this raw, untouched farmland is a rare find in one of Vermont’s most

  Margretta Fischer Wohler Realty Group

  215 Vermont 30, Dorset, VT 05251
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  /8

  $9,999

  • Land
  • 1.2 Acres
  • $8,332 per Acre

  0 Alpendorf Ave, Readsboro, VT 05350

  Stake a claim on your own little piece of Vermont, at the foot of the Green Mountain National Forest. This 1.2-acre triangular lot rises up from the road and may allow peekaboo views of the surrounding valley starting in late-fall, once the region's famous foliage drops away. It's located in Alpenwald Village, with community-maintained roads rolling up and down the area's hilly topography. Today

  David White OwnerEntry.com

  0 Alpendorf Ave, Readsboro, VT 05350
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  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs.Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201
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  /23

  $360,000

  • 3 Beds
  • 2 Baths
  • 1,590 Sq Ft

  22 Carlen St, Manchester Center, VT 05255

  Live in one and rent the other. Discover the charm and value of this affordable starter home with rental option. Located in a quiet, residential area of Manchester. This spacious ranch-style property offers a rare combination of flexibility, space, and opportunity, perfect for first-time buyers, investors, or anyone looking to create their dream home with a few finishing touches. The main level

  Andy Reed Four Seasons Sotheby's Int'l Realty

  22 Carlen St, Manchester Center, VT 05255
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  /28

  $424,900

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  139 Bergwelt Ln, Readsboro, VT 05350

  Charming Country Retreat with Scenic Views and Timeless Character.Welcome to your dream country escape! Nestled on a peaceful, tree-lined lane, this beautifully maintained 3-bedroom, 2-bathroom home offers the perfect blend of rustic charm and modern comfort. Set on a spacious 3.6 acre lot, the property boasts serene views, mature gardens, and ample privacy — ideal for relaxing weekends or

  Heidi Zizza Four Seasons Sotheby's Int'l Realty

  139 Bergwelt Ln, Readsboro, VT 05350
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  /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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  /32

  $368,000

  • 3 Beds
  • 2 Baths
  • 1,337 Sq Ft

  78 Carbonti Cir, Arlington, VT 05250

  Easy single-level living! Welcome to Arlington's Carbonti Circle. Updated three-bedroom, two-bath ranch nestled in a quiet neighborhood setting just minutes from downtown Arlington and the famous Battenkill River. Set on a .30-acre lot, this home offers the perfect blend of comfort, character and convenience. Experience easy living in this beautifully maintained single-level home! Enjoy a

  Margretta Fischer Wohler Realty Group

  78 Carbonti Cir, Arlington, VT 05250
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  /41

  $349,000

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  509 Thompson Pond Rd, Pownal, VT 05261

  Discover Your Perfect Getaway at Verdmont If you're a nature enthusiast, a rare and exclusive opportunity awaits at the Verdmont Outing Club. Nestled in the heart of the Green Mountain Preserve, this gated community spans nearly 500 acres of unspoiled wilderness-a true haven for outdoor living.As a shareholder, you'll enjoy a wealth of amenities: Water & Land Privileges: Two stunning

  Kelley Mccarthy Mahar McCarthy Real Estate

  509 Thompson Pond Rd, Pownal, VT 05261
• 

  

  /23

  $249,000

  • Land
  • 17.6 Acres
  • $14,148 per Acre

  88 Cedar Ln, Peru, VT 05152

  Tucked away in the heart of the Green Mountains, this stunning 17.60-acre parcel in picturesque Peru, Vermont, is a rare opportunity to create your dream retreat. The land is richly wooded, offering a serene natural setting filled with mature trees and gently rolling terrain that promises a spectacular display of fall foliage—an ever-changing canvas of vibrant reds, oranges, and golds each

  Joe Castaluccio Winhall Real Estate

  88 Cedar Ln, Peru, VT 05152
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  /17

  $145,000

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft

  432 South St Unit C6, Bennington, VT 05201

  A fresh perspective on easy living! Welcome to this beautifully maintained 2BR/1.5 BA second-floor condo in Nathanial Court offering the perfect blend of comfort, convenience, and low-maintenance living. Step into a bright and airy open floor plan, where large windows flood the space with natural light. The tidy kitchen boasts ample cabinet space, sleek stainless steel appliances, and a clean

  Angela Bevin Maple Leaf Realty

  432 South St Unit C6, Bennington, VT 05201
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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
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  /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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  /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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  /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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  /34

  $565,000

  • 4 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  22 Bromley Forest Rd, Bondville, VT 05340

  Welcome to your ideal Vermont retreat where comfort, style, and location converge! This upgraded 4-bedroom home, complete with a versatile bonus room, has been meticulously maintained and offers an open floor plan perfect for gathering and everyday living. The kitchen shines with stainless steel appliances and a new professional grade dual-fuel convection range. East and south facing windows

  Carrie Mathews Winhall Real Estate

  22 Bromley Forest Rd, Bondville, VT 05340
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  /33

  $775,000

  • 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
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  /38

  $485,000

  • 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
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  /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

  $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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  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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 bed

  Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

  68 Owls Nest Cir Unit B-7, Manchester, VT 05254

Showing Results 121 - 160, Page 4 of 6