Bennington County VT Homes for Sale

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  $1,225,000

  • 4 Beds
  • 3 Baths
  • 3,357 Sq Ft

  153 High Meadow Rd, Winhall, VT 05340

  Located in Stratton Resort’s sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace.Recent

  Britt Wohler

  153 High Meadow Rd, Winhall, VT 05340
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  /41

  $429,000

  • 2 Beds
  • 2 Baths
  • 6,686 Sq Ft

  3310 Vt Route 346, Pownal, VT 05261

  Paul Harsch Harsch Associates

  3310 Vt Route 346, Pownal, VT 05261
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  /53

  $825,000

  $74K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,112 Sq Ft

  2572 Morse Hill Rd, Dorset, VT 05251

  Some properties announce everything at once. Others reward the buyer w/ discernment to see what is quietly waiting to be realized. Set along the rise of Morse Hill Road, this Dorset home is a rare opportunity: a substantial residence on 10 acres where value extends beyond what exists today into what the land could become. Beyond a beautiful Vermont home, there is potential to shape an

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

  2572 Morse Hill Rd, Dorset, VT 05251
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  /25

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,688 Sq Ft

  171 Garbrooke Dr, Bennington, VT 05201

  Welcome to this inviting Cape-style home offering 3 bedrooms, 2 baths and a comfortable layout designed for both everyday living and entertaining. The main level features an open-concept kitchen and dining area that flows directly onto a huge back deck—an ideal spot for summer dinners, gatherings or simply relaxing while overlooking the secluded, wooded backyard. With both a living room and

  Lilli West Maple Leaf Real Estate

  171 Garbrooke Dr, Bennington, VT 05201
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  /14

  $159,900

  • 5 Beds
  • 1 Bath
  • 1,593 Sq Ft

  493 Main Rd, Stamford, VT 05352

  Bring your imagination to this over 1500 sq. ft. 5 bedroom, New England farmhouse and let it go wild! Level one acre lot with attached shed and small outbuilding for animals or projects. And the sunsets-- oh the sunsets! Relax on your open porch and take in the breathtaking beauty of the western sky as the day winds down.Very easy main route access, close to downtown and Stamford Elementary

  Pauline Green Lamacchia Realty, Inc. - Adams

  493 Main Rd, Stamford, VT 05352
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  /29

  $439,000

  • 2 Beds
  • 2.5 Baths
  • 1,490 Sq Ft

  7330 Main St, Manchester Center, VT 05255

  Charming Main Street Manchester Barn with Mountain ViewsConveniently located on Main Street in Manchester, this charming barn offers a wonderful combination of character, comfort, and versatility. The open-concept main level features an eat-in kitchen with distinctive post-and-beam details and a spacious living room with a propane fireplace. The living area opens directly to a large

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  7330 Main St, Manchester Center, VT 05255
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  /27

  $995,000

  • 5 Beds
  • 2 Baths
  • 3,522 Sq Ft

  2529 Main St, Manchester, VT 05254

  Light, bright, & thoughtfully updated, this charming Manchester village home offers the perfect blend of antique character, modern convenience, & exceptional outdoor space. Set on nearly five acres of level, usable land with beautiful views toward Mount Equinox, the property provides room to spread out & enjoy everything Vermont living has to offer—whether gathering with family & friends,

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  2529 Main St, Manchester, VT 05254
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  /3

  $475,000

  • Land
  • 12.82 Acres
  • $37,051 per Acre

  22 Morse Rd, Bennington, VT 05201

  Positioned in the heart of Bennington’s commercial corridor on 12.82 open acres, 22 Morse Road present a prime development opportunity. Offering excellent visibility and accessibility along one of the area’s primary commercial arteries, the property is ideally situated for a variety of commercial, retail, service, mixed-use, or redevelopment possibilities. The location provides convenient access

  Paul Carroccio TPW Real Estate

  22 Morse Rd, Bennington, VT 05201
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  /32

  $265,000

  $10K PRICE DROP

  • 1,680 Sq Ft

  318 North St, Bennington, VT 05201

  Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a

  Jenifer Prouty Hoffman Hoffman Real Estate

  318 North St, Bennington, VT 05201
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  /38

  $360,000

  • 2 Beds
  • 2 Baths
  • 1,841 Sq Ft

  5892 Route 100 Route, Londonderry, VT 05148

  Charming Farmhouse Gem in the Heart of LondonderryWelcome home to this inviting 2-bedroom, bonus room and 2-bathroom residence centrally located in Londonderry, VT a dream location for outdoor enthusiasts with quick, convenient access to world-class skiing at Magic, Bromley, Stratton, and Okemo Mountains in the winter. Summer and fall you are close to hiking the multitude of trails,

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  5892 Route 100 Route, Londonderry, VT 05148
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  /34

  $115,000

  $10K PRICE DROP

  • Land
  • 2.9 Acres
  • $39,655 per Acre

  311 Beechwood Ln, Peru, VT 05152

  This lovely, nearly 3 acre parcel of land is located on Beechwood Lane, about 1 mile from the Town center of Peru. There is approximately 353' frontage on Beechwood Lane and approximately 271' frontage on Beechnut Drive. The land is gently sloped and nicely wooded for privacy. Xfinity high speed internet available. Peru features the J.J. Hapgood General store, Peru Congregational Church, Hapgood

  Dylan Gage Bromley Real Estate

  311 Beechwood Ln, Peru, VT 05152
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  /34

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 2,746 Sq Ft

  2436 Mad Tom Rd, East Dorset, VT 05253

  Picture yourself on 12 private wooded acres along one of Vermont's most scenic country roads in a classic 4-bedroom, 3-bath Colonial offering the perfect blend of comfort, character, and outdoor adventure. Built in 1977 and thoughtfully maintained, the home welcomes you with warm hardwood floors, a beautifully renovated kitchen featuring soapstone countertops, abundant cabinetry, and a sunny

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2436 Mad Tom Rd, East Dorset, VT 05253
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  /43

  $1,250,000

  $245K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,170 Sq Ft

  50 Grouse Ln, Dorset, VT 05251

  Custom built Dorset Hollow estate offered for the first time since 1998. Perfectly situated on 10 private acres abutting 3,200 acres of conservation land, this 5,100 sq ft residence combines timeless quality, fine finishes, and Vermont mountain charm. Designed for comfort and entertaining, the home features 4 bedrooms, 5 bathrooms, and an attached 2-car garage. Elegant details include four

  David Halligan Four Seasons Sotheby's Int'l Realty

  50 Grouse Ln, Dorset, VT 05251
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  /8

  $239,000

  • Land
  • 5.35 Acres
  • $44,673 per Acre

  01 Old Depot Rd, West Arlingtn, VT 05250

  Big views, open land, and room to make it your own. Offered as two lots under a single listing, this 5+ acre property is an inviting piece of the Arlington countryside, with sweeping views of both the Taconic and Green Mountains. The open field overlooks a privately maintained pond and enjoys a peaceful setting just down the road from one of Southern Vermont's most charming farms. An approved

  Marek Kovac TPW Real Estate

  01 Old Depot Rd, West Arlingtn, VT 05250
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  /22

  $579,000

  • 3 Beds
  • 1.5 Baths
  • 2,048 Sq Ft

  560 New Ireland Rd, Manchester Center, VT 05255

  This charming two-story Colonial in Manchester offers a comfortable and functional layout with plenty of living space. The first floor features a kitchen with a wood burning fireplace, along with dining and living areas perfect for everyday living and entertaining. A mudroom provides convenient access to the attached garage. Upstairs, you’ll find three additional rooms offering flexibility for

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  560 New Ireland Rd, Manchester Center, VT 05255
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  /16

  $299,900

  • 3 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  1725 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

  Nature lovers, rejoice! Situated on 23 private acres with a beautiful mountain view, this property offers exceptional privacy and seclusion surrounded by the natural beauty of Vermont. With abundant space to explore, relax, and enjoy the outdoors, it’s an ideal setting for those seeking a peaceful country retreat. The main level features a spacious open floor plan with a large kitchen and

  Matt Waddington Hoffman Real Estate

  1725 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
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  /47

  $524,900

  • 4 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  87 Grinka Farm Dr, Readsboro, VT 05350

  Set on 5 acres in the scenic hills of Readsboro, this spacious 4-bedroom, 2.5-bath farmhouse offers privacy, mountain views, and plenty of room to enjoy Vermont’s natural beauty. The 2,120-square-foot interior features warm wood flooring, abundant natural light, and a welcoming layout designed for everyday living and entertaining. The kitchen offers generous cabinetry, ample workspace, and an

  Colt Hazell Flex Realty

  87 Grinka Farm Dr, Readsboro, VT 05350
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  /49

  $1,375,000

  $75K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,376 Sq Ft

  39 Eagle Ridge, Dorset, VT 05251

  5.7 beautiful acres just off of Morse Hill Road where the southern exposures are to behold, a warm and inviting modern designed residence, post and beam barn and sweeping mountain views await your attention! The 5 Bedroom mostly ensuite house features the grand open concept where living areas are spacious and distinctive areas yet transition beautifully from space to space with newly finished

  Laura Beckwith Josiah Allen Real Estate, Inc.

  39 Eagle Ridge, Dorset, VT 05251
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  /49

  $675,000

  New Construction

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

  40 Jameson Flats, Manchester, VT 05255

  NEW CONSTRUCTION | EXCEPTIONAL CRAFTSMANSHIP | PRIME MANCHESTER LOCATIONThis exceptional new-construction 3-bedroom, 2.5-bath duplex has been thoughtfully designed and built to an exceptionally high standard, combining refined finishes, impressive craftsmanship, and highly efficient modern systems just steps from the heart of Manchester.The open-concept main level is designed for both

  Britt Wohler

  40 Jameson Flats, Manchester, VT 05255
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  /16

  $96,406

  New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  32 Cassie Ln, Bennington, VT 05201

  Welcome to 32 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  32 Cassie Ln, Bennington, VT 05201
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  /41

  $299,000

  $50K PRICE DROP

  • 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
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  /16

  $325,000

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  4362 Vt Route 11 Rd Unit 1A, Peru, VT 05152

  Two Bedroom, 1 Bathroom condo

  Dylan Gage Bromley Real Estate

  4362 Vt Route 11 Rd Unit 1A, Peru, VT 05152
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  /29

  $3,250,000

  • 5 Beds
  • 7 Baths
  • 8,156 Sq Ft

  1613 West Rd, Manchester, VT 05254

  Located in the beautiful countryside of Manchester, Vermont, 1613 West Road offers a peaceful setting with the kind of charm and character that makes this property truly one of a kind. Surrounded by scenic mountain views, open land, and natural surroundings, the property strikes a perfect balance of privacy and convenience. Just a short drive from the heart of Manchester, you enjoy easy access to

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  1613 West Rd, Manchester, VT 05254
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  /60

  $1,125,000

  • 4 Beds
  • 3 Baths
  • 2,614 Sq Ft

  3269 Route 30, Dorset, VT 05251

  Historic District, Dorset Village 4 Bedroom Colonial Farmhouse located with both residential and commercial zoning walk to every village amenity such as the Dorset Inn, Barrows House and Pool, Dorset Bakery, The Union Store, The Field Club, Dorset Library, Theater, Historic Society, and the Pinnacle walking trail. Recently restored this residence lives comfortably with extensive rear yard gardens

  Laura Beckwith Josiah Allen Real Estate, Inc.

  3269 Route 30, Dorset, VT 05251
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  /21

  $132,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  60 Tori Ln, Bennington, VT 05201

  Very well kept single-wide mobile home on it's own land. Cozy 2 bedroom, 1 bathroom home with single level living. Living room, kitchen with dining area, main level laundry and more. Has 2 enclosed porches. The smaller one is used as a pantry and the larger one is heated. Outside 2 sheds and the sounds of the nearby babbling brook. Also has RV electric hook up.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  60 Tori Ln, Bennington, VT 05201
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  /23

  $525,000

  Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,532 Sq Ft

  46 Equinox On the Battenkill Unit A8, Manchester, VT 05254

  Beautifully sited end unit with attractive landscaping; trees border along the right side and backyard off 2 decks and a patio; enjoy viewing the Green Mountains while listening to the babbling Battenkill River or sit enjoying the beautiful garden space with morning coffee; capture some creative ideas to bring back a fresh, updated look to this well designed Taconic condo layout... consisting of

  Donna Murray Varick Associates Ltd

  46 Equinox On the Battenkill Unit A8, Manchester, VT 05254
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  /2

  $425,000

  • Land
  • 3 Acres
  • $141,667 per Acre

  lot A Forest Pond Rd, Dorset, VT 05251

  Private Dorset West Road Location... private road... nearby Manchester and Dorset. Ready to build. Waste Water permit in place for 5 BR, 8 person occupancy.

  Charles Mauro Josiah Allen Real Estate, Inc.

  lot A Forest Pond Rd, Dorset, VT 05251
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  /47

  $2,850,000

  $150K PRICE DROP

  • 2 Beds
  • 3.5 Baths
  • 5,731 Sq Ft

  2334 Morse Hill Rd, Dorset, VT 05251

  Beautiful Dorset Contemporary Offering Privacy, Comfort, and Easy Living.If you’ve been looking for a private Vermont retreat with room to relax, entertain, and enjoy the beauty of every season, this exceptional custom home may be the perfect fit. Built in 1996 by respected Dorset builder Keith Dodson, this thoughtfully designed 5,731 sq. ft. contemporary sits on 12.15 peaceful acres with

  David Halligan Four Seasons Sotheby's Int'l Realty

  2334 Morse Hill Rd, Dorset, VT 05251
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  /42

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  336 Kirby Hollow Rd, Dorset, VT 05251

  Set in a premier Dorset country setting with sweeping 360-degree views of rolling pastures, mountains, and neighboring farmland, this charming single-level ranch offers a rare opportunity to enjoy the beauty and tranquility of Southern Vermont.The home offers over 1,568 square feet of comfortable living space, including an open-concept kitchen, dining, and living area, an office, three

  Britt Wohler

  336 Kirby Hollow Rd, Dorset, VT 05251
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  /32

  $675,000

  • 3 Beds
  • 1 Bath
  • 1,575 Sq Ft

  221 Landgrove Rd, Londonderry, VT 05148

  With more than 80 acres spanning the towns of Landgrove and Peru, this spectacular property is ripe for your imagination and offers several options for new construction, multi-family or generational development, or renovation! Be it choosing the perfect building site for the construction of your Vermont dream house, a total renovation of the existing three-bedroom cottage, or continuing to use

  Claudia Harris Mary Mitchell Miller Real Estate

  221 Landgrove Rd, Londonderry, VT 05148
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  /52

  $565,000

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,399 Sq Ft

  1131 Route 30, Dorset, VT 05251

  Making its first appearance on the market in generations, this beloved circa-1850 New Englander is filled with warmth, character, and endless potential. Situated on 1.5 picturesque acres along Route 30, midway between the charming villages of Dorset and Manchester, the property offers an exceptional setting with easy access to local shops, restaurants, hiking trails, skiing, and all the amenities

  David Shehadi Josiah Allen Real Estate, Inc.

  1131 Route 30, Dorset, VT 05251
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  /23

  $219,000

  $16K PRICE DROP

  • 1,860 Sq Ft

  205 County St, Bennington, VT 05201

  This well maintained 2-unit home exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family. use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 2-bedroom and 3-bedroom units, this property is designed to adapt to

  Dan Mason Perrott Realty

  205 County St, Bennington, VT 05201
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  /22

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 3,018 Sq Ft

  111 Eagle Rise Rd Unit 22, Manchester, VT 05255

  This exquisite, unattached 3 bedroom, 2.5 bath townhome at Eagle Rise in Manchester, VT offers the perfect blend of sophisticated design, comfort, and effortless mountain living. Completely renovated with contemporary amenities and thoughtfully curated finishes, this move in ready home is designed for both elegant entertaining and relaxed everyday living. The beautifully renovated kitchen and

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

  111 Eagle Rise Rd Unit 22, Manchester, VT 05255
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  /60

  $180,000

  $20K PRICE DROP

  • Land
  • 58.1 Acres
  • $3,098 per Acre

  1073 Chapel Rd, Bennington, VT 05201

  Unlock the potential of this spectacular 58.1 +/- acre woodland property in historic Bennington. The groundwork for your future home or getaway is already laid with a State-approved wastewater permit in place for a three-bedroom single-family residence, allowing you the flexibility to design your build. Further simplifying your plans, the property offers the rare advantage of connecting to the

  Curtis Trousdale Preferred Properties

  1073 Chapel Rd, Bennington, VT 05201
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  /25

  $375,000

  New Construction $25K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,190 Sq Ft

  527 Jennings Brook Dr, Bennington, VT 05201

  Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. Custom Kitchen with granite countertops, custom tile shower unit. The open-concept layout is highlighted by a spacious kitchen and a

  Lilli West Maple Leaf Real Estate

  527 Jennings Brook Dr, Bennington, VT 05201
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  /60

  $385,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,593 Sq Ft

  1111 Old Depot Rd, Shaftsbury, VT 05262

  Open House September 6 Sunday Noon to 2Welcome to 1111 Old Depot Road in Shaftsbury, Vermont, where country living and natural beauty come together on approximately four scenic acres. This inviting four-bedroom, two-full-bath ranch-style home offers a rare opportunity to enjoy privacy, natural beauty, and convenient access to one of Southern Vermont's most beloved recreational

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  1111 Old Depot Rd, Shaftsbury, VT 05262

Showing Results 241 - 276, Page 7 of 7