Bennington County VT Homes for Sale

• 

  

  

  /55

  $495,000

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  935 Old Manchester Rd, Peru, VT 05152

  Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski AccessEscape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure.Fully self-sufficient with solar power and propane generator

  Margretta Fischer Wohler Realty Group

  935 Old Manchester Rd, Peru, VT 05152
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  /44

  $365,000

  • 3 Beds
  • 1 Bath
  • 1,660 Sq Ft

  989 Carpenter Hill Rd, Bennington, VT 05201

  Country charm meets modern comfort... Welcome to your perfect slice of paradise! This lovingly updated ranch home is nestled on a peaceful country road and sits on a generous 2.6 acre lot, offering the ideal blend of privacy, space, and style. Step inside to discover a bright, refreshed interior featuring new vinyl plank flooring, freshly painted walls in a neutral palate, and updated lighting

  Angela Bevin Maple Leaf Realty

  989 Carpenter Hill Rd, Bennington, VT 05201
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  /27

  $319,000

  • 3 Beds
  • 1 Bath
  • 836 Sq Ft

  557 Beech St, Manchester Center, VT 05255

  Manchester. Let the sun shine in. Easy living on one level with 3 bedrooms. You'll enjoy sitting in the kitchen and gazing either at the mountain view or the flower garden in the backyard. Nice level area to plant a garden or play outdoor games in the yard. Detached 1 car garage, good storage and area for workbench. Quick drive into center of Manchester and minutes to the Manchester Country Club.

  Patti Trudel RE/MAX Four Seasons

  557 Beech St, Manchester Center, VT 05255
• 

  

  

  /30

  $495,000

  • 7 Beds
  • 4 Baths
  • 2,494 Sq Ft

  190 Cemetery Rd, Arlington, VT 05250

  This is a RARE two lot offering!! It is located on Cemetery Rd in Arlington,VT with quiet, secluded lots. Great opportunity for multi-generational living, guest house, rental income, air bnb, extra space or great resale opportunity. House #1 is a two story house on 2.29 surveyed acres with 4 bedrooms and 1 3⁄4 bathrooms. The living room features a cathedral ceiling with skylights and a wood

  

  Trent Stephens

  Wohler Realty Group

  (802) 200-2970

  190 Cemetery Rd, Arlington, VT 05250
• 

  

  

  /20

  $649,000

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

  27 Owls Head Hill Ln, Dorset, VT 05251

  Charming Raised Ranch on 2 Acres – Dorset, VTWelcome to your new home in the heart of Dorset! Nestled on a beautifully landscaped 2-acre corner lot, this inviting raised ranch offers privacy, comfort, and versatile living space.3 Bedrooms | 2 Full Baths | 2-Car Attached GarageStep inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect for everyday

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  27 Owls Head Hill Ln, Dorset, VT 05251
• 

  

  /21

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  58 Walker Meadows, Arlington, VT 05250

  Afordable Single level Three bedroom, two bath home on a wonderful level lot. Convenient location to schools, town restaurants, shopping, library, physicians and hiking trails. A sweet spot to enjoy the large back yard and spacious deck. From the deck you can enter the great room with French doors allowing for natural light and the wood burning fireplace. This cozy welcoming home features hard

  Margretta Fischer Wohler Realty Group

  58 Walker Meadows, Arlington, VT 05250
• 

  

  /21

  $120,000

  • Land
  • 20 Acres
  • $6,000 per Acre

  1319 Vail Rd, Bennington, VT 05201

  Discover an exceptional opportunity to build your dream home on this prime 20-acre parcel located in the desirable west end of Bennington. This expansive property offers a perfect blend of privacy and convenience, ready for immediate development.Key features of this remarkable land include an established driveway providing easy access to your future homesite, and a completed perk test

  Lilli West Maple Leaf Realty

  1319 Vail Rd, Bennington, VT 05201
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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! 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 enjoyed fireside under the stars.The main

  Jessica Citera Cummings & Co

  288 Cedar Ln, Peru, VT 05152
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  /39

  $289,000

  • 2 Beds
  • 1.5 Baths
  • 1,417 Sq Ft

  51 Russell St Unit D, Arlington, VT 05250

  A Wonderful Townhouse in desirable Arlington Village. Welcome to this charming 2 bedroom 1 and a half bath nestled in the heart of Arlington, with a one car garage. This location offers the perfect blend of comfort and convenience. Inside you will find newly refinished hardwood floors, updated tiling at the entry, and stainless steel appliances. A sun drenched living room and dining area walks

  Robert Sabol Wohler Realty Group

  51 Russell St Unit D, Arlington, VT 05250
• 

  

  /15

  $269,000

  • 2 Beds
  • 1 Bath
  • 2,500 Sq Ft

  624 Main St, Bennington, VT 05201

  Prime Mixed-Use Building on Main Street-Bennington, Vermont. Located in the heart of downtown Bennington, this versatile mixed-use property offers an excellent opportunity for both investors and owner-occupants. The main level features a spacious, adaptable commercial space ideal for retail, office, or service-based businesses. With its high visibility and foot traffic on Main Street, this is a

  Kelley Mccarthy Mahar McCarthy Real Estate

  624 Main St, Bennington, VT 05201
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  /39

  $599,000

  • 5 Beds
  • 3.5 Baths
  • 2,468 Sq Ft

  17 Signal Hill Rd, Winhall, VT 05340

  17 Signal Hill Road offers Vermont charm in a secluded mountain setting. With over 2,400 square feet of living space, this five-bedroom, three-and-a-half-bath home has been thoughtfully maintained and move-in ready. The main level features a spacious living room with a dramatic fieldstone fireplace, vaulted ceilings, and skylights that fill the home with natural light. A loft overlooking

  Christiane Carroccio TPW Real Estate

  17 Signal Hill Rd, Winhall, VT 05340
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  /35

  $575,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft

  704 Fox Hill Rd, Bennington, VT 05201

  House hunting in Vermont and can't find what you want? Or it sold before you had time to tour or think it through? This brand new custom built home could be the answer. Desirable neighborhood with paved town roads, close to SVMC hospital, Bennington College, downtown restaurants and events, and one hour from Albany Int'l Airport. Nestled at the base of Mount Anthony, there's direct access to

  Jenifer Prouty Hoffman Hoffman Real Estate

  704 Fox Hill Rd, Bennington, VT 05201
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  /47

  $625,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  682 Fox Hill Rd, Bennington, VT 05201

  Soak up the mountain view from a brand new custom built home. Desirable neighborhood with paved town maintained roads. Just outside of Old Bennington and close to SVMC hospital, downtown restaurants and theaters. An easy commute to Bennington College, 22 minute drive to Williamstown, MA or an hour to Albany Int'l Airport. Nestled at the base of Mount Anthony, hikers will appreciate direct

  Jenifer Prouty Hoffman Hoffman Real Estate

  682 Fox Hill Rd, Bennington, VT 05201
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  /37

  $1,695,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,688 Sq Ft

  143 Stratton Mountain Access Rd, Winhall, VT 05340

  Just Completed by DG Builders in Stratton, Vermont143 Stratton Mountain Access Road, a newly completed 5-bedroom, 5-bath residence, located just minutes from Stratton Mountain Resort and all the year-round activities it has to offer. Blending modern mountain style with timeless Vermont charm, this home is move-in ready and waiting for its first owners.The light-filled open floor plan

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  143 Stratton Mountain Access Rd, Winhall, VT 05340
• 

  

  /22

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,248 Sq Ft

  203 Northside Dr, Bennington, VT 05201

  Welcome to 203–205 Northside Drive, a truly unique property that combines residential living with commercial potential all in one. Are you looking for the flexibility to live in an apartment while generating income from multiple rental units, or would you prefer to restore the property back into a spacious single-family residence? This property gives you both options. Currently configured with

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 471-3591

  203 Northside 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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  /43

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  683 Water St, North Bennington, VT 05257

  Completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom with private bathroom and an

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  683 Water St, North Bennington, VT 05257
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  /27

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,958 Sq Ft

  550 Finbars Forest Rd, Manchester Center, VT 05255

  Tucked away on a private two-acre lot in the heart of the Green Mountains and within the Burr & Burton Academy school district, this modern farmhouse offers a peaceful setting minutes from downtown Manchester and adjacent to Manchester Country Club. The main level features an open-concept layout with a beautifully designed kitchen at its center - rich dark cabinetry, Caesarstone quartz

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  550 Finbars Forest Rd, Manchester Center, VT 05255
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  /51

  $269,000

  • 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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  /4

  $39,500

  • Land
  • 2 Acres
  • $19,750 per Acre

  0 Oberhugel Rd Unit 5059139, Stamford, VT 05352

  Here are 2 beautiful wooded lots high on the mountain! Perfect opportunity for you to create your paradise in southern Vermont! Alpenwald is a hidden gem - a community on a mountain across from an old ski area which has been repurposed for Backcountry skiing and hiking. Alpenwald also has direct access to the VAST trail network as well as ATV trails. It is also not far from ski areas such as MT

  Duncan Honig Maple Leaf Realty

  0 Oberhugel Rd Unit 5059139, Stamford, VT 05352
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  /26

  $199,900

  • 4 Beds
  • 2 Baths
  • 1,278 Sq Ft

  215 Maple St, Bennington, VT 05201

  Huge Price Reduction. Enjoy the charm and comfort of this beautifully renovated home, ideally nestled in the heart of Bennington. As you arrive, you'll be greeted by a spacious front porch, perfect for relaxation, entertaining, and enjoying cool breezes. This property has undergone a complete transformation from a two-family to a stunning single-family home. It now offers convenient one-floor

  Matt Waddington Hoffman Real Estate

  215 Maple St, Bennington, VT 05201
• 

  

  /22

  $375,000

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

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340

  Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

  Robin Apps Four Seasons Sotheby's Int'l Realty

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340
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  /56

  $1,849,000

  • 3 Beds
  • 2.5 Baths
  • 3,450 Sq Ft

  139 Prospect St, Manchester, VT 05254

  Set against Equinox Mountain and just minutes from the thriving center of Manchester, this timeless and elegant home has been thoughtfully renovated to honor age-old craftsmanship while embracing modern building science to create a beautiful, healthy, and inviting space. Recent renovations include a comprehensive rebuild and expansion of the upper floor, Marvin windows and patio doors, charming

  Cheyanne Pugliese

  139 Prospect St, Manchester, VT 05254
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  /40

  $1,525,000

  • 4 Beds
  • 3 Baths
  • 3,931 Sq Ft

  932 Mcnamara Rd, Dorset, VT 05251

  Tucked away at the end of a gently curved, tree-lined drive, this exceptional contemporary home blends timeless elegance with Vermont charm. A welcoming paver patio leads to the informal entry, while a marble pathway guides you to the striking formal entrance and grand foyer. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality

  Britt Wohler

  932 Mcnamara Rd, Dorset, VT 05251
• 

  

  /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
• 

  

  /36

  $224,500

  • 5 Beds
  • 2 Baths
  • 2,212 Sq Ft

  1138 Main Rd, Stamford, VT 05352

  Stamford, VT - A country drive less than 10 minutes North Adams, MA- home of Mass MoCA. Dating back to 1850 this spacious home boasts 4 bedrooms & 2 baths. 1st floor bedroom, bath, laundry, kitchen, dining, living room, den & sunroom. Nestled on almost and acre of land and bordering a babbling brook this property offers a privacy sanctuary. Come take a look for yourself! Located close to

  Colleen Zajac MONARCH REALTY, INC.

  1138 Main Rd, Stamford, VT 05352
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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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  /41

  $360,000

  • 3 Beds
  • 1 Bath
  • 1,432 Sq Ft

  231 Bergrucken Ln Unit 121-122, Readsboro, VT 05350

  Discover the perfect balance of privacy, outdoor adventure, and scenic beauty in this recently updated 3-bedroom, 1-bath home nestled in the heart of Vermont’s Green Mountains —this rare gem is one of the few properties in the community with a view. The property features gently winding grass paths that invite you to explore your own backyard oasis, ideal for morning exercise, birdwatching, or

  Kristen Breeden Southern Vermont Realty Group

  231 Bergrucken Ln Unit 121-122, Readsboro, VT 05350
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  /46

  $805,000

  • 4 Beds
  • 2.5 Baths
  • 2,220 Sq Ft

  392 Powderhorn Rd, Manchester Center, VT 05255

  Set on two private acres in a desirable Manchester location, this renovated four-bedroom, three-bath Colonial offers a quiet retreat with convenient access to both Manchester and Dorset. Wide-plank pine floors and abundant natural light define the interiors, creating an inviting flow throughout. The main level includes a spacious living room with a stone fireplace, a formal dining room,

  Alexandra Crowley Four Seasons Sotheby's Int'l Realty

  392 Powderhorn Rd, Manchester Center, VT 05255
• 

  

  /38

  $749,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 4,683 Sq Ft

  2744 Danby Mountain Rd, Dorset, VT 05251

  This classic Vermont mountain retreat offers the perfect blend of comfort, privacy, and year-round recreation. Located just minutes from Dorset Village and Manchester, the property is surrounded by adventure—ski touring, snowshoeing, and hiking are all available right from your yard. A new wrap-around Trex deck invites you to unwind or dine outdoors while taking in views of the gardens and

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  2744 Danby Mountain Rd, Dorset, VT 05251
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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
• 

  

  /43

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  100 Walsh Rd, Arlington, VT 05250

  Tucked away in the picturesque Vermont Hamlet of Sandgate, home to just 480 residents, this property provides the perfect escape from the bustle of city life. Here, you can enjoy the warmth of a close-knit community, stunning natural surroundings, and easy access to local amenities. Sitting on a generous 1.5-acre lot, the property offers ample space for outdoor recreation and the peaceful

  

  Kristin Comeau

  TPW Real Estate

  (802) 521-2780

  100 Walsh Rd, Arlington, VT 05250
• 

  

  /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
• 

  

  /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
• 

  

  /23

  $775,000

  • 4 Beds
  • 3.5 Baths
  • 3,784 Sq Ft

  258 Mending Walls Rd, Manchester Center, VT 05255

  Nestled in the highly sought-after Mending Walls Subdivision, this beautiful 4-bedroom, 4-bathroom Colonial offers the perfect blend of comfort, space, and curb appeal. Set back on a level lot, enjoy serene mornings and evenings from the welcoming front porch overlooking the expansive front yard.The main level boasts spacious living area perfect for entertaining and everyday living.

  Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

  258 Mending Walls Rd, Manchester Center, VT 05255
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  /35

  $635,000

  • 5 Beds
  • 2 Baths
  • 2,050 Sq Ft

  1649 E Manchester Rd, Manchester Center, VT 05255

  Privately set yet moments from Manchester's boutiques, dining, and year-round recreation, this five-bedroom, two bath Cape offers a rare blend of quiet retreat and unmatched accessibility. Every space has been curated for comfort, versatility, and style, ideal for full-time living, a vacation escape, and many other possibilities. The kitchen, a refined anchor to the home, features stainless steel

  Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

  1649 E Manchester Rd, Manchester Center, VT 05255
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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
• 

  

  /44

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  475 Sunrise Ln, Arlington, VT 05250

  Discover your private retreat on Beautiful Sunrise Lane! Welcome to "Pine Hollow". This comfortable and inviting home sits on over 6 acres of serene, peaceful landscape, for those seeking a quiet environment and space! Idyllic setting surrounded by pines with complete solitude at the end of a private rd. Enjoy the comfort of generous rooms filled with natural light, ideal for family living and

  Sunny Breen Josiah Allen Real Estate, Inc.

  475 Sunrise Ln, Arlington, VT 05250
• 

  /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
• 

  

  /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

Showing Results 81 - 120, Page 3 of 6