Bennington County VT Homes for Sale

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  /41

  $279,000

  • 2 Beds
  • 1 Bath
  • 2,142 Sq Ft

  32 Albe Dr, Bennington, VT 05201

  MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect for those looking for the convenience of first floor living. Featuring tastefully painted rooms, bamboo flooring and modern appliances.The kitchen includes a dedicated eating area for family dining while the living room offers a warm and cozy gathering space. Both bedrooms are generously sized with large

  Beatrice O'Connell Maple Leaf Realty

  32 Albe Dr, Bennington, VT 05201
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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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  /41

  $950,000

  Open Sat 1:30PM - 3:30PM

  • 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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  /45

  $490,642

  $8K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,708 Sq Ft

  145 Oberdorf Rd, Readsboro, VT 05350

  Welcome to Alpenwald Village, a peaceful mountain community in scenic Readsboro, Vermont. This charming 4-bedroom chalet sits on 2 private acres and offers the perfect blend of comfort, style, and access to Vermont’s four-season lifestyle. Whether you're searching for a full-time residence or the ideal vacation getaway, this beautifully updated home delivers. Step inside to discover thoughtful

  Evan Russell Real Broker LLC

  145 Oberdorf Rd, Readsboro, VT 05350
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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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  /47

  $1,375,000

  New Construction Open Sun 11AM - 2PM Coming Soon

  • 3 Beds
  • 4.5 Baths
  • 3,415 Sq Ft

  3746 Main St Unit 1, Manchester, VT 05255

  Last Available Unit– This final Monarch on Main townhome is Luxury Living in Historic Manchester Village at its finest. Summer 2026, this premier Monarch on Main property offers the rare opportunity to own a thoughtfully designed townhome- front unit- in the heart of Manchester Village. Imagine an easy stroll to fine dinning, shopping and evening events. This three-level residence combines the

  Britt Wohler

  3746 Main St Unit 1, Manchester, VT 05255
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  /30

  $300,000

  $25K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 1,120 Sq Ft

  113 South St Unit 302, Bennington, VT 05201

  Whether you’re seeking a full-time downtown lifestyle, a lock-and-leave home base for travel, or you’re ready to make the leap from renting to owning, this is the kind of property that checks every box—location, character, and simplicity. Offered publicly for the first time, Unit 302 is filled with natural light from tall windows that frame the energy of downtown Bennington. Soaring ceilings,

  Jenifer Prouty Hoffman Hoffman Real Estate

  113 South St Unit 302, Bennington, VT 05201
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  /48

  $3,285,000

  • 5 Beds
  • 6 Baths
  • 6,900 Sq Ft

  68 Green Peak Orchard S, East Dorset, VT 05253

  Located in the desirable Green Peak Orchard, this exceptional custom Greek Revival residence is set on 9.9 private acres surrounded by mature landscaping, stone walls, and terraces. Thoughtfully designed with timeless craftsmanship, the home features wide-plank floors, hand-plastered walls and ceilings, custom moldings, historic reproduction lighting, and finely crafted wainscoting and cabinetry.

  Carol O`Connor Four Seasons Sotheby's Int'l Realty

  68 Green Peak Orchard S, East Dorset, VT 05253
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  /15

  $825,000

  • Land
  • 77.6 Acres
  • $10,631 per Acre

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

  Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

  Trent Stephens Wohler Realty Group

  0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
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  /12

  $69,000

  $6K PRICE DROP

  • Land
  • 13.01 Acres
  • $5,304 per Acre

  3 W Hill Dr, Readsboro, VT 05350

  Discover the potential of this 13-acre parcel in scenic Readsboro offering RR (Rural Residential) zoning and endless possibilities. With gently rolling terrain and potential for views, this property is ideal for a private home or possible subdivision. Aerial photos and videos available! Enjoy a true outdoor lifestyle with nearby access to skiing, hiking, fishing, boating, snowmobile trails, and

  Derek Greene Derek Greene

  3 W Hill Dr, Readsboro, VT 05350
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  /8

  $65,000

  • Land
  • 1.24 Acres
  • $52,419 per Acre

  2041 East Rd, Bennington, VT 05201

  Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life. Perk test were positive for a inground leaching system, results available.

  Dan Mason Perrott Realty

  2041 East Rd, Bennington, VT 05201
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  /60

  $1,900,000

  • 6 Beds
  • 6 Baths
  • 5,704 Sq Ft

  751 Main Rd, Stamford, VT 05352

  Step into the most amazing Victorian house you will ever see! Built in 1880, you will feel like you've walked back in time. Beautiful architecture and woodwork. The house was built by John Tudor, a Welsh immigrant who had made a fortune as a mill owner in northern Vermont and settled in Stamford. There is a stunning 3 floor Post & Beam Barn built in 2000 with a 2 car garage built-in. Barn also

  Michael Jarvis United Country Real Estate Mike Jarvis Group Inc

  751 Main Rd, Stamford, VT 05352
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  /37

  $875,000

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  155 Brookman Rd, Pownal, VT 05261

  Gorgeous setting for this newly constructed home built in 2025, offering breathtaking views from the expansive front porch on 10+/- private acres. Thoughtfully designed with quality craftsmanship throughout, the custom kitchen features beautiful cabinetry, a large center island, gas range, and classic farmhouse sink, all open to the inviting living room with a cozy gas fireplace. The stunning

  Kelley Mccarthy Mahar McCarthy Real Estate

  155 Brookman Rd, Pownal, VT 05261
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  /60

  $1,495,000

  $300K PRICE DROP

  • 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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  /7

  $100,000

  • Land
  • 26.2 Acres
  • $3,817 per Acre

  0 Magee Rd Unit 249355, Stamford, VT 05352

  Uncover this hidden and exceptional 26.2-acre property featuring two prime lots, perfect for development or creating your personal retreat. This picturesque Vermont landscape is highlighted by small streams and even a tranquil pond, complete with wide trails that ensure easy navigation throughout the property for access, exercise and recreational vehicles. Complete with remarkable stone outcrops

  Gary Fuls Jr RE/MAX TRANSITIONS

  0 Magee Rd Unit 249355, Stamford, VT 05352
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  /27

  $609,000

  • 4 Beds
  • 3 Baths
  • 1,650 Sq Ft

  60 Hilltop Rd Unit 60, Winhall, VT 05340

  Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  60 Hilltop Rd Unit 60, Winhall, VT 05340
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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 bedrooms.

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, 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

  Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont living. Rolling terrain, mature woodland, and natural clearings create an exceptional setting for a private Vermont retreat, with the potential for Bromley Mountain views depending on house placement and design.Supported by a

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  56 Lower Taylor Hill Rd, Winhall, VT 05340
• 

  

  /19

  $499,000

  • 6 Beds
  • 6 Baths
  • 9,000 Sq Ft

  425 Main St, Bennington, VT 05201

  15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

  Chris Long BHG Masiello Brattleboro

  425 Main St, Bennington, VT 05201
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  /6

  $99,000

  $11K PRICE DROP

  • 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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  /57

  $2,275,000

  $25K PRICE DROP

  • 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

  $2,875,000

  $475K PRICE DROP

  • 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 suites,

  David Shehadi Josiah Allen Real Estate, Inc.

  466 3 Maple Dr, Manchester, VT 05254
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  /39

  $1,575,000

  • 4 Beds
  • 5.5 Baths
  • 4,530 Sq Ft

  527 Sleighbell Ln, Manchester Center, VT 05255

  Set on over 11.5 private acres, this custom-built Colonial offers the kind of comfort, craftsmanship, and peace of mind that’s increasingly hard to find. Thoughtfully designed and maintained since it was built in 2004, this home blends timeless style with practical features for everyday living. With over 4,300 square feet, the layout provides generous space without feeling overwhelming. The home

  David Halligan Four Seasons Sotheby's Int'l Realty

  527 Sleighbell Ln, Manchester Center, VT 05255
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  /30

  $219,000

  • 4 Beds
  • 1 Bath
  • 1,127 Sq Ft

  20 Sage St, North Bennington, VT 05257

  Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an

  Abi Gregorio

  20 Sage St, North Bennington, VT 05257
• 

  /2

  $249,000

  • Land
  • 29.9 Acres
  • $8,328 per Acre

  0 North Rd Unit 5079306, East Arlington, VT 05252

  Once you locate this quiet parcel there is a lovely wooded setting which offers a potential for a family compound or a possible subdivision. See Directions.There utilities along the extensive road frontage of North Road and Bacon Hollow Road which is a dead end... No soils or engineering value completed and must be processed with new zoning and state permitting.

  Charles Mauro Josiah Allen Real Estate, Inc.

  0 North Rd Unit 5079306, East Arlington, VT 05252
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  /20

  $199,500

  $16K PRICE DROP

  • Land
  • 4.46 Acres
  • $44,731 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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  /33

  $649,000

  • 3 Beds
  • 3 Baths
  • 1,650 Sq Ft

  39 Pond View Rd Unit 39, Winhall, VT 05340

  Set in a prime location along Stratton Access Road, this Intervale townhouse offers an easygoing mountain lifestyle with everything you need close at hand—including weekend and holiday winter shuttle service to the base lodge.The 3-bedroom + loft, 3-bath layout provides plenty of space for guests, while the open living area brings everyone together with a seamless flow between the kitchen,

  Carrie Mathews Winhall Real Estate

  39 Pond View Rd Unit 39, Winhall, VT 05340
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  /50

  $699,500

  New Construction $96K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,760 Sq Ft

  38 Jameson Flats, Manchester, VT 05255

  NEW CONSTRUCTION -Showings Begin 3/1.This beautifully designed 3-bedroom, 2.5-bath Condo blends modern comfort & energy-conscious features in a prime location, just steps from the heart of Manchester. An open-concept main living area is perfect for entertaining, with a kitchen featuring an eat-in island, ample storage, stainless steel appliances, including your choice of electric or propane

  Britt Wohler

  38 Jameson Flats, Manchester, VT 05255
• 

  

  /14

  $125,000

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft

  347 Hickory Rd, Bennington, VT 05201

  Your wait is over—an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach

  Thomas Martins Maple Leaf Realty

  347 Hickory Rd, Bennington, VT 05201
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  /38

  $349,000

  $10K PRICE INCREASE

  • 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
• 

  

  /20

  $600,000

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

  00 Vermont 11, Peru, VT 05152

  Sweeping views of Stratton, Bromley, and Magic Mountains define this 28 +/- acre offering in Peru, Vermont, where rare east, south, and westerly exposure provides exceptional natural light and solar orientation throughout the day. The surrounding landscape combines open mountain vistas, varied terrain, and connection to the Green Mountains in a setting shaped by Southern Vermont’s four-season

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
• 

  

  /38

  $4,999,000

  $2M PRICE DROP

  • 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
• 

  /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 and the trails 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
• 

  

  /5

  $375,000

  $90K PRICE DROP

  • Land
  • 5.54 Acres
  • $67,690 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
• 

  

  /52

  $89,900

  $9K PRICE DROP

  • 1 Bed
  • 586 Sq Ft

  845 Bailey Hill Rd, Readsboro, VT 05350

  Wonderful little getaway for some ''EZ'' living—be one with nature with all the essentials in place! It’s common to see wildlife in this rural setting, making it perfect to create your ideal Vermont retreat. Nestled among the trees, you’ll relish the peaceful ambiance and natural beauty that surrounds you, offering a true sense of escape from the everyday hustle. A tidy, compact getaway with a

  Dan Mason Perrott Realty

  845 Bailey Hill Rd, Readsboro, VT 05350
• 

  

  /8

  $59,000

  • Land
  • 12,632 Sq Ft
  • $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
• 

  

  /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
• 

  

  /14

  $219,995

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  240 Church St, Shaftsbury, VT 05262

  Ready for its next owner! This charming home offers a great opportunity for anyone looking to put their personal touch on a property with tons of potential. Sitting on an acre-sized lot, there’s plenty of room to expand. Inside, the home needs some TLC—but that’s where the value lies. With the right updates, you can truly bring your vision to life. The layout also provides potential for an in-law

  Derek Greene Derek Greene

  240 Church St, Shaftsbury, VT 05262

Showing Results 161 - 200, Page 5 of 6