Bennington County VT Homes for Sale

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  /2

  $2,190,000

  • Land
  • 1.16 Acres
  • $1,887,931 per Acre

  301 Northside Dr, Bennington, VT 05201

  Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

  Paul Carroccio TPW Real Estate

  301 Northside Dr, Bennington, VT 05201
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  /29

  $250,000

  • 9 Beds
  • 5 Baths
  • 3,810 Sq Ft

  6982 Main St, Readsboro, VT 05350

  Prime location meets potential! Situated in the center of charming Readsboro, this 5-unit multi-family property offers a rare opportunity for investors and owner-occupants alike. Whether you're looking to expand your portfolio or live in one unit while generating rental income from the others, this property delivers. Some renovations needed – perfect for those looking to add value and

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  6982 Main St, Readsboro, VT 05350
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  /50

  $259,000

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  3264 Route 153, West Rupert, VT 05776

  This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical with a

  Scott McChesney McChesney RE, Inc.

  3264 Route 153, West Rupert, VT 05776
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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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  /3

  $219,000

  • 2 Beds
  • 1 Bath
  • 1,872 Sq Ft

  17 Henry Hill, Stamford, VT 05352

  Sean Taylor Moresi Real Estate Partners

  17 Henry Hill, Stamford, VT 05352
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  /17

  $79,900

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  108 Baker Dr, Bennington, VT 01237

  Built in 2000 this charming home is located in Catamount Mobile Home Park, a community with no age restrictions in beautiful Bennington, Vermont. Situated on a large corner lot with front and back decks offering mountain views. Open, light-filled floor plan with bright kitchen, living room, primary suite, second bedroom, full bath, and laundry. Features include anewer shed (1 year old) and

  Colleen Zajac MONARCH REALTY, INC.

  108 Baker Dr, Bennington, VT 01237
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  /41

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  7 Roundtree Rd, Winhall, VT 05340

  Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  7 Roundtree Rd, Winhall, VT 05340
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  /4

  $28,000

  • Land
  • 2.3 Acres
  • $12,174 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own a

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /24

  $471,000

  • 3 Beds
  • 2 Baths
  • 1,357 Sq Ft

  102 Mccormick Ln, Sunderland, VT 05250

  Built in 2003, the home's open-concept design is highlighted by a bright and airy living/dining/kitchen area, where large windows flood the space with abundant natural light. A cozy pellet stove provides warmth and ambiance for those crisp Vermont evenings. The functional layout features two comfortable bedrooms and a full bathroom on the main level, while the private primary ensuite bedroom

  Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

  102 Mccormick Ln, Sunderland, VT 05250
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  /36

  $355,000

  • 4 Beds
  • 2 Baths
  • 2,108 Sq Ft

  149 Jewett Dr, Bennington, VT 05201

  Tucked just outside of town with sweeping views in every direction, this 4-bedroom, 2-bath raised ranch offers the space and setting you're looking for. Hardwood floors run throughout the main level, where the sun-filled living room features a cozy wood-burning fireplace—perfect for gathering on chilly evenings. The finished lower level provides flexible space to grow, including the third and

  Faith Rhodes Maple Leaf Realty

  149 Jewett Dr, Bennington, VT 05201
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  /30

  $550,000

  • 2 Beds
  • 2 Baths
  • 2,218 Sq Ft

  1439 Main St, Manchester Center, VT 05255

  Purdy School House, est. 1850 - Step into history with this lovingly preserved former schoolhouse, offering timeless character with modern comfort. Featuring 2 bedrooms, 2 baths, and a striking stone fireplace, this home blends warmth and charm. A full basement and attached one-car garage provide practical convenience. Set on 2.01 acres, the property includes a fenced dog yard and plenty of space

  Richard Slocum Four Seasons Sotheby's Int'l Realty

  1439 Main St, Manchester Center, VT 05255
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  /4

  $190,000

  • 5 Beds
  • 2 Baths
  • 1,478 Sq Ft

  32-34 Sage St, Bennington, VT 05257

  Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer. Current tenants keep their units up well.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  32-34 Sage St, Bennington, VT 05257
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  /60

  $1,595,000

  • 17 Beds
  • 20 Baths
  • 14,861 Sq Ft

  3888 Vermont Route 7a, Shaftsbury, VT 05262

  The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

  Vicki Wilson Maple Leaf Realty

  3888 Vermont Route 7a, Shaftsbury, VT 05262
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  /4

  $27,999

  • Land
  • 2.4 Acres
  • $11,666 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 2.4-acre lot offers the perfect blend of privacy and convenience. Power is available at the road. Whether you're seeking a peaceful retreat or a year-round residence, this spacious lot provides ample room for gardens, recreation, and more, all within a welcoming mountain community. Don't miss this opportunity to own

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
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  /39

  $1,289,000

  • 5 Beds
  • 4.5 Baths
  • 4,540 Sq Ft

  84 Edward Isham Dr, Manchester Center, VT 05255

  Set in a desirable neighborhood just minutes from Manchester Village, this beautifully maintained home offers expansive mountain views in both directions, abundant natural light, and exceptional living space across three finished levels. Designed for comfortable living and easy entertaining, the recently renovated kitchen features a quartz island and marble countertops and opens to inviting

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  84 Edward Isham Dr, Manchester Center, VT 05255
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  /23

  $340,000

  • 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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  /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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  /29

  $415,000

  • 6 Beds
  • 3 Baths
  • 5,208 Sq Ft

  126 Washington Ave, Bennington, VT 05201

  Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

  Vicki Wilson Maple Leaf Realty

  126 Washington Ave, Bennington, VT 05201
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  /15

  $500,000

  • Land
  • 21.2 Acres
  • $23,585 per Acre

  56 Lower Taylor Hill Rd, Winhall, VT 05340

  A rare opportunity to create a private Vermont retreat on 21.2 +/- acres along Lower Taylor Hill Road in Winhall. The property is supported by a State-approved wastewater permit for a six (6) bedroom single-family residence, offering flexibility to design a substantial home within permitted limits. Rolling terrain, natural clearings, and mature woodland provide multiple potential building sites,

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  56 Lower Taylor Hill Rd, Winhall, VT 05340
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  /55

  $995,000

  • 5 Beds
  • 4.5 Baths
  • 2,321 Sq Ft

  24 N Branch Rd, Winhall, VT 05340

  Exceptional Renovation of a Stratton Resort Residence in the Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite- this mountain chalet has been updated

  Kim Morgan-Wohler Wohler Realty Group

  24 N Branch Rd, Winhall, VT 05340
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  /6

  $99,000

  • Land
  • 1 Acre
  • $99,000 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 Site PlanCovenants

  Andrew King Stratton Real Estate

  88A Sylvan Ridge Rd, Winhall, VT 05340
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  /56

  $2,300,000

  • 9 Beds
  • 8 Baths
  • 5,512 Sq Ft

  288 Cedar Ln, Peru, VT 05152

  Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be

  Jessica Citera Cummings & Co

  288 Cedar Ln, Peru, VT 05152
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  /56

  $3,350,000

  • 3 Beds
  • 4.5 Baths
  • 3,059 Sq Ft

  466 3 Maple Dr, Manchester, VT 05254

  Welcome to Three Maple Drive, a beautifully crafted, brand-new single-family home nestled in a quiet and scenic location in Manchester, Vermont. Built in 2023 with impeccable attention to detail, this 3,059 sq ft modern farmhouse seamlessly blends luxury, comfort, and timeless design—all set on a private 3.85-acre lot with gorgeous mountain views.This home features three spacious bedroom

  David Shehadi Josiah Allen Real Estate, Inc.

  466 3 Maple Dr, Manchester, VT 05254
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  /37

  $585,000

  • 3 Beds
  • 2 Baths
  • 2,070 Sq Ft

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

  Special Price!! EOB Unit B-7!!! Equinox on the Battenkill, one of Southern Vermont’s premier condo/resort communities located in the historic village of scenic Manchester. This charming 3 bed 2 bath luxury town home, one of the select few with attached garages, offers the privacy of a quiet cul de sac, beautifully landscaped. Four seasons living in sought out neighborhood, Owls Nest! Management

  Dana Kingsley Josiah Allen Real Estate, Manchester Branch Office

  68 Owls Nest Cir Unit B-7, Manchester, VT 05254
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  /47

  $245,000

  • 2 Beds
  • 2 Baths
  • 911 Sq Ft

  726 Rice Ln, Bennington, VT 05201

  Welcome to this charming Cape-style home, nestled in a peaceful country setting just moments from Bennington College and scenic walking and hiking trails. This inviting property offers the perfect blend of rural tranquility and convenient access to town. Located just 10 minutes from downtown Bennington, you’ll have quick access to local shops, restaurants, cultural attractions, and everyday

  Thomas Martins Maple Leaf Realty

  726 Rice Ln, Bennington, VT 05201
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  /20

  $215,000

  • Land
  • 4.46 Acres
  • $48,206 per Acre

  OA E Manchester Rd, Manchester, VT 05255

  Very desirable lot off East Manchester Road with several building possibilities. Gently sloping, preliminary septic permit in place and access to all Manchester has to offer.

  Peter Pierce EXP Realty

  OA E Manchester Rd, Manchester, VT 05255
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  /54

  $389,900

  • 3 Beds
  • 3.5 Baths
  • 2,148 Sq Ft

  328 Chester Knoll Dr, Bennington, VT 05201

  Well-maintained 2005 tri-level home offering comfortable, easy living in a desirable residential neighborhood. Features include efficient radiant floor heat, mini-split system for added comfort and new vinyl plank flooring on the lower and main levels. The kitchen is outfitted with attractive cherry cabinets and offers a functional layout for everyday living. Located within a PUD, the HOA covers

  Vicki Wilson Maple Leaf Realty

  328 Chester Knoll Dr, Bennington, VT 05201
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  /49

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  2092 N Bennington Rd, North Bennington, VT 05257

  Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedrooms upstairs and a pocket half bathroom. downstairs has a master bedroom with a newly remodeled ensuite, kitchen with breakfast table area, 4 seasons living space in the back and a front livingroom with new flooring. The previous owner used the 4 seasons room as a formal dining room since it has

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  2092 N Bennington Rd, North Bennington, VT 05257
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  /28

  $414,900

  • 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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  /56

  $929,000

  • 4 Beds
  • 3 Baths
  • 2,068 Sq Ft

  104 High Meadow Rd, Winhall, VT 05340

  Location says it all. This High Meadow mountain retreat is located in one of Stratton Resort’s premier locations. High Meadow offers winter weekend and holiday shuttle service to the slopes for your convenience. Bathed in sunshine thanks to its southern exposure, this contemporary home welcomes you with a seamless open floor plan that flows effortlessly from the kitchen into expansive

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  104 High Meadow Rd, Winhall, VT 05340
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  /34

  $339,000

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  This inviting in-town home has been nearly completely renovated with only a few more touches to be brought by the new owner, blending fresh updates with classic comfort. Inside, you’ll find 3 bedrooms and a full bath, plus a bonus room that could serve as a 4th bedroom with a half-bath. An additional room with its own separate entrance is ideal for a small home business. The convenient attached

  Cassie Barbeau Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
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  /20

  $600,000

  • Land
  • 28 Acres
  • $21,429 per Acre

  00 Vermont 11, Peru, VT 05152

  28 +/- acre parcel in Peru Vermont with views of Stratton Mountain, Bromley Mountain and Magic Mountain. Rare east, south and westerly exposure provides consistent natural light and excellent solar orientation throughout the day. Positioned across from Johnny Seesaw’s and minutes to Bromley Market and Bromley Mountain Ski Resort, the property offers privacy with immediate access to dining, skiing

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
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  /50

  $4,999,000

  • 6 Beds
  • 7.5 Baths
  • 8,720 Sq Ft

  454 Mountain Rd, Stratton, VT 05155

  Welcome to a one-of-a-kind 141-acre mountaintop retreat at Stratton Mountain Resort - an extraordinary sanctuary with panoramic views of Stratton, Mount Snow, and Bromley. Designed for elegance and ease, this home is a rare blend of architectural beauty, comfort, and sophistication. A gracious entryway opens to a sunlit living room and library anchored by an 18-foot stone fireplace. Expansive

  Lisa Sullivan Four Seasons Sotheby's Int'l Realty

  454 Mountain Rd, Stratton, VT 05155
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  /2

  $65,000

  • Land
  • 17.3 Acres
  • $3,757 per Acre

  0 Hidden Valley Rd Unit 5055076, Shaftsbury, VT 05262

  Ready to build 17 acer lot with wastewater permit for a 4 bedroom single family residence. Great potential for a pond site, the trail on the lot make it a great opportunity for a horse paddock.

  Dan Mason Perrott Realty

  0 Hidden Valley Rd Unit 5055076, Shaftsbury, VT 05262
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  /25

  $1,425,000

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

  1058 Granger Hollow Rd, North Bennington, VT 05257

  A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room.Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef’s kitchen

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  1058 Granger Hollow Rd, North Bennington, VT 05257
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  /37

  $999,000

  • 4 Beds
  • 3.5 Baths
  • 2,280 Sq Ft

  17 Roundtree Rd, Winhall, VT 05340

  Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

  Sarah Nichols Winhall Real Estate

  17 Roundtree Rd, Winhall, VT 05340
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  /5

  $440,000

  • Land
  • 5.54 Acres
  • $79,422 per Acre

  Lot #4 Margeaux Ln, Stratton, VT 05155

  Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  Lot #4 Margeaux Ln, Stratton, VT 05155
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  /8

  $59,000

  • Land
  • 0.29 Acre
  • $203,448 per Acre

  420 Burgess Rd, Bennington, VT 05201

  Level building lot with town sewer and water at the edge of town.Possible owner financing.

  Dan Mason Perrott Realty

  420 Burgess Rd, Bennington, VT 05201
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  /16

  $139,000

  • Land
  • 1.62 Acres
  • $85,802 per Acre

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340

  wooded slightly elevated parcel. With clearing there should be some across valley views. Past soil test indicates proposed septic locations.Five-minute walk to Stratton snowmaking pond.

  Mike England Michael England Real Estate

  0 Lower Taylor Hill Rd Unit 19, Winhall, VT 05340
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  /58

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  27 Broken Pines Dr, Bennington, VT 05201

  Welcome to your peaceful country retreat just over the Bennington town line in Shaftsbury! This 3BR/2BA ranch offers effortless one-level living on a generous 3.5-acre lot surrounded by nature and abundant wildlife. The heart of the home features a modern eat-in kitchen with granite countertops, custom Kraftmaid cabinets installed in 2022 and durable vinyl plank flooring throughout, creating a

  Vicki Wilson Maple Leaf Realty

  27 Broken Pines Dr, Bennington, VT 05201

Showing Results 121 - 160, Page 4 of 5