Bennington, VT Homes

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  /60

  $1,950,000

  • 4 Beds
  • 3.5 Baths
  • 3,333 Sq Ft

  1268 Myers Rd, Shaftsbury, VT 05262

  Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, a 2 car garage, top notch equestrian facilities, a trout and koi pond, and the list goes on and on. The winding driveway leads to a world away, as it opens to view of the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 441-6014

  1268 Myers Rd, Shaftsbury, VT 05262
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  /37

  $219,000 Sold Aug 29, 2025

  • 1,156 Sq Ft
  • $189/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  261 Sycamore Ln, Shaftsbury, VT 05262

  Welcome to 261 Sycamore Lane, Shaftsbury, VT!Nestled in a desirable neighborhood, this charming Cape Cod style home is a perfect fit for first-time homebuyers or those looking to downsize into something more manageable. Set of 0.35 acres, the home offers 3 bedrooms and 1 full bath, with added convenience of a first-floor bedroom and bath.Enjoy a spacious backyard perfect for pets, kids,

  Brooke Thomson Drew Mahar McCarthy Real Estate

  261 Sycamore Ln, Shaftsbury, VT 05262
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  /36

  Est $956,745 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,104 Sq Ft

  469 Laclair Rd, Shaftsbury, VT 05262

  469 Laclair Rd, Shaftsbury, VT 05262
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  /36

  $490,000

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

  1061 Granger Hollow Rd, North Bennington, VT 05257

  Dreaming of a peaceful Vermont lifestyle? This three bedroom, 2 bath home sits on 11.5 acres of beautiful land with rolling open mountain views, a stream, mature apple trees, and an inground pool all the ingredients for your perfect retreat.Step inside to this home that has had a complete refresh. The home offers a first floor bedroom and full bath with a step in shower, making it great

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 481-3292

  1061 Granger Hollow Rd, North Bennington, VT 05257
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  /57

  $256,000 Sold Aug 25, 2025

  • 1,224 Sq Ft
  • $209/SF
  • 4 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1978

  153 Spur Rd Unit PVT, Bennington, VT 05201

  Simplify life in this charming one-story home nestled on 2 peaceful acres, offering the perfect blend of privacy and convenience just minutes from town. Thoughtfully designed for comfort and accessibility, this cozy 3-bedroom property features an open-concept kitchen, dining, and living area centered around a classic brick fireplace—ideal for Vermont’s cozy seasons.Enjoy the warmth of a bonus

  Lindsey Martin Maple Leaf Realty

  153 Spur Rd Unit PVT, Bennington, VT 05201
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  /40

  Est $315,423 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  216 Bank St, North Bennington, VT 05257

  216 Bank St, North Bennington, VT 05257
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  /13

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  2017 East Rd, Shaftsbury, VT 05262

  3 bedroom 2 bath, double wide on 1.49 acres in Shaftsbury. Offering good location, large yard, and convenient travel to town. Living room with new pellet stove, kitchen with modern appliances including newer stove and dining area. Outside a 2 car detached garage, storage sheds and front and rear porches. New carpet.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 798-5968

  2017 East Rd, Shaftsbury, VT 05262
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  /56

  $245,000 Sold Aug 18, 2025

  • 1,660 Sq Ft
  • $148/SF
  • 11 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1946

  174 Cleveland Ave, Shaftsbury, VT 05262

  Fresh clean ranch ready for your finish touched. This house was just painted and the roof was replaced. Large fenced back yard for pets. The deck id ready for a new pool or just access the backyard for games or leisure. Easy to show and move in ready.

  Dan Mason Perrott Realty

  174 Cleveland Ave, Shaftsbury, VT 05262
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  /37

  Est $365,627 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft

  91 Mcguire St, North Bennington, VT 05257

  91 Mcguire St, North Bennington, VT 05257
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  /60

  $1,795,000

  • 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

  (802) 444-8317

  3888 Vermont Route 7a, Shaftsbury, VT 05262
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  /40

  $225,000 Sold Aug 18, 2025

  • 1,538 Sq Ft
  • $146/SF
  • 12 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1890

  721 Vt Route 7a, Shaftsbury, VT 05262

  Located in the downtown neighborhood of Shaftsbury. Walking distance to school, town offices, country stores, parks and playgrounds. A first-floor bedroom with French doors leading outside - as well as a first-floor family room, laundry room, new kitchen and den. Two bedrooms upstairs. There's plenty of room in this home. A one car garage and fully fenced in lot for your privacy.

  Wendy Larson Hooscik Realty

  721 Vt Route 7a, Shaftsbury, VT 05262
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  /30

  Est $426,809 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 3,334 Sq Ft

  94 Lake Dr, North Bennington, VT 05257

  94 Lake Dr, North Bennington, VT 05257
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  /34

  $399,900 Under Contract

  • 2 Beds
  • 3 Baths
  • 1,700 Sq Ft

  43 Spur Rd, Bennington, VT 05201

  Private and gorgeous home situated on 3.54 acres in Shaftsbury. Offering 2 bedrooms with a full primary suite (large primary bathroom and walk in closet), 3 total bathrooms and modern design. Enjoy the large airy and open living room with fireplace, modern kitchen with plenty of cupboards and marble counter top and dining area with slider to the private backyard and multi-level deck. Many

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 255-8583

  43 Spur Rd, Bennington, VT 05201
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  /35

  $420,000 Sold Aug 14, 2025

  • 1,832 Sq Ft
  • $229/SF
  • 69 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1985

  1283 Hidden Valley Rd, Shaftsbury, VT 05262

  Welcome to the one you’ve been waiting for in sought after Shaftsbury! This beautifully updated, low-maintenance Colonial offers comfort, style, and space, inside and out. Step into a freshly painted interior where thoughtful updates shine throughout. The heart of the home is the spacious kitchen, featuring all new appliances, gleaming granite countertops, and abundant cabinetry, perfect for

  Angela Bevin Maple Leaf Realty

  1283 Hidden Valley Rd, Shaftsbury, VT 05262
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  /38

  Est $469,378 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,082 Sq Ft

  27 Horton Hill Rd, Shaftsbury, VT 05262

  27 Horton Hill Rd, Shaftsbury, VT 05262
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  /46

  $850,000

  • 5 Beds
  • 2 Baths
  • 2,424 Sq Ft

  2 Cold Spring Rd, North Bennington, VT 05257

  Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 810-8434

  2 Cold Spring Rd, North Bennington, VT 05257
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  /31

  $400,000 Sold Aug 13, 2025

  • 1,624 Sq Ft
  • $246/SF
  • 10 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1961

  2374 Shaftsbury Hollow Rd, North Bennington, VT 05257

  Escape to peace and privacy in this beautiful 2-bedroom, 1 bath getaway home set on 7.15 picturesque acres, complete with your own private pond and surrounded by majestic mountains. Step inside to an open-concept kitchen, dining, and living area-perfect for entertaining or simply soaking in the serenity. The space is filled with natural light thanks to large windows that frame the stunning views.

  Kelley Mccarthy Mahar McCarthy Real Estate

  2374 Shaftsbury Hollow Rd, North Bennington, VT 05257
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  /40

  Est $377,485 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  211 Grandview St, North Bennington, VT 05257

  211 Grandview St, North Bennington, VT 05257
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  /17

  $485,000

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

  Discover a true Vermont lifestyle at this meticulously maintained charming farmhouse nestled on picturesque Shaftsbury Hollow Road. This property combines historic character with thoughtful modern updates, offering a serene retreat with breathtaking mountain views across a just shy of 10-acre lot where the White Creek gracefully runs along one side and the entire back boundary. Step out onto the

  Lori Hurley Four Corner Properties LLC

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
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  /40

  $615,000 Sold Aug 07, 2025

  • 3,173 Sq Ft
  • $194/SF
  • 85 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1804

  5529 Vt Route 7a, Shaftsbury, VT 05262

  Presenting an absolutely detail rich and unspoiled 1804 Center Hall Post & Beam Colonial on Historic 7A that promises to create wonderful memories for its steward. Nurture has been the key to preserving the casual grace of this 5 bay noted residence; with a stunning 33' X 15'6" great room centered on the fireplace, this space provides living / dining perfect for hosting today's lifestyle needs

  Laura Beckwith Josiah Allen Real Estate, Inc.

  5529 Vt Route 7a, Shaftsbury, VT 05262
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  /39

  Est $256,401 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,413 Sq Ft

  61 Dunham Ave, North Bennington, VT 05257

  61 Dunham Ave, North Bennington, VT 05257
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  /36

  $498,000

  • 3 Beds
  • 2 Baths
  • 1,671 Sq Ft

  6 Dwyers Camp Rd, Shaftsbury, VT 05262

  Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior,

  Lori Hurley Four Corner Properties LLC

  6 Dwyers Camp Rd, Shaftsbury, VT 05262
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  /35

  $279,000 Sold Aug 07, 2025

  • 1,740 Sq Ft
  • $160/SF
  • 30 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  65 Mountain View Dr, Shaftsbury, VT 05262

  3 bed 2 bath ranch with great views of the Green Mountain Range in a country setting in the Shaftsbury School District. Double flue chimney ready for a secondary heat source.

  Dan Mason Perrott Realty

  65 Mountain View Dr, Shaftsbury, VT 05262
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  /40

  Est $518,181 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,042 Sq Ft

  287 Hewitt Dr, North Bennington, VT 05257

  287 Hewitt Dr, North Bennington, VT 05257
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  /59

  $679,000

  • 3 Beds
  • 2.5 Baths
  • 3,637 Sq Ft

  272 Oak Hill Rd, Shaftsbury, VT 05262

  Built in 2001, this stunning contemporary home sits on just under 8 peaceful acres and offers a perfect blend of space, light, and comfort. The grand two-story living room features soaring ceilings and a cozy pellet stove, creating an impressive focal point. The first floor offers a spacious primary suite for ultimate convenience, along with a dedicated home office—perfect for remote work or

  Faith Rhodes Maple Leaf Realty

  272 Oak Hill Rd, Shaftsbury, VT 05262
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  /42

  $252,000 Sold Jul 25, 2025

  • 768 Sq Ft
  • $328/SF
  • 41 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1965

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257

  A peace of heaven in the Hollow! Idyllic setting with 3.5 acres surrounded by trees. The property borders the Little White Creek, with hiking/biking trails all around for your own outdoor adventure or peaceful relaxation. Adorable house with 2 bedrooms, 1 bath, and an open concept main room. Wood-burning fireplace in the living room, plus there's a wood boiler and oil-fired hot air furnace in

  Jenifer Prouty Hoffman Hoffman Real Estate

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257
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  /14

  Est $261,916 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,508 Sq Ft

  169 Reservoir Rd, Shaftsbury, VT 05262

  169 Reservoir Rd, Shaftsbury, VT 05262
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  /48

  $899,000

  • 4 Beds
  • 4 Baths
  • 3,691 Sq Ft

  42 Airport Rd, Shaftsbury, VT 05262

  Welcome to this exquisite post and beam timber frame home, nestled in a prime location just moments from the Mount Snow Ski Resort and Mount Snow Golf Course. This remarkable 4-bedroom, 4-bathroom home blends rustic charm with modern luxury, offering an unparalleled mountain retreat perfect for both relaxation and adventure. As you step inside, you’ll be greeted by soaring ceilings and

  Mike Masters Four Seasons Sotheby's Int'l Realty

  42 Airport Rd, Shaftsbury, VT 05262
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  /41

  $750,000 Sold Jul 14, 2025

  • 1,836 Sq Ft
  • $408/SF
  • 55 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2022

  482 Horton Hill Rd, Shaftsbury, VT 05262

  Built in 2021, this stylish 3 bed, 3 bath modern home sits on 9.8 acres with wide open views from every angle. Large windows and a wraparound Trex deck with sleek cable railing blur the lines between indoors and out, with access from both the living room and primary suite. Inside, the open layout is designed for today's living-featuring a gorgeous kitchen with stainless appliances, granite

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  482 Horton Hill Rd, Shaftsbury, VT 05262
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  /40

  Est $575,973 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,982 Sq Ft

  1004 Holy Smoke Rd, Shaftsbury, VT 05262

  1004 Holy Smoke Rd, Shaftsbury, VT 05262
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  /49

  $595,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,278 Sq Ft

  199 North Rd, Shaftsbury, VT 05262

  Expansive Home with Guest House on Nearly 10 Serene Acres. Tucked away on almost 10 peaceful acres, this beautifully crafted property offers a spacious main home and a well-appointed guest house-ideal for multigenerational living, rental income, or hosting guests. The main residence impresses with its soaring cathedral ceilings in the living room, a dramatic floor-to-ceiling stone fireplace, and

  Timothy Corcoran Mahar McCarthy Real Estate

  199 North Rd, Shaftsbury, VT 05262
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  /60

  $420,000 Sold Jun 26, 2025

  • 2,753 Sq Ft
  • $153/SF
  • 31 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  123 Bank St, North Bennington, VT 05257

  Modern Updated Cape! Be amazed when you step into this expansive open concept home. This property has been lovingly updated, embracing a modern style. New flooring, new roof, two new baths, new windows & doors. Plus seamless gutters. Expanded finished square footage enhances the open flow and easy living. The Great Room offers open living/ kitchen/dining with a beverage bar, fire feature and

  Margretta Fischer Wohler Realty Group

  123 Bank St, North Bennington, VT 05257
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  /36

  Est $297,035 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,695 Sq Ft

  566 Vt Route 7a, Shaftsbury, VT 05262

  566 Vt Route 7a, Shaftsbury, VT 05262
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  /27

  $212,000

  • 3 Beds
  • 2 Baths
  • 1,959 Sq Ft

  198 Twitchell Hill Rd, Shaftsbury, VT 05262

  Discover the potential in this spacious 3-bedroom home, nestled in a beautiful setting with room to make it your own. Offering a flexible floor plan, the home includes two primary bedrooms that share a full bathroom, plus an additional guest bedroom and bath, making it ideal for multi-generational living or visiting guests. Inside, you’ll find a sunken living room that adds character and charm,

  Faith Rhodes Maple Leaf Realty

  198 Twitchell Hill Rd, Shaftsbury, VT 05262
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  /44

  $565,000 Sold Jun 26, 2025

  • 2,325 Sq Ft
  • $243/SF
  • 86 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1978

  196 Glastenview Dr, Shaftsbury, VT 05262

  Fully Renovated 4 bedroom plus office, Ranch-Rambler with stunning views.This home has undergone a complete transformation, featuring a reconfigured floor plan, new roof, siding, furnace, bathrooms, kitchen, flooring, deck, and landscaping. Enjoy open-concept living with a spacious kitchen, dining area, and living room that seamlessly flow together. Step outside onto the back deck for

  Lori Hurley Four Corner Properties LLC

  196 Glastenview Dr, Shaftsbury, VT 05262
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  /18

  Est $217,731 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,361 Sq Ft

  43 Buck Hill Rd, Shaftsbury, VT 05262

  43 Buck Hill Rd, Shaftsbury, VT 05262
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  /36

  $399,000

  • 5 Beds
  • 3 Baths
  • 3,118 Sq Ft

  100 McCarthy Acres, North Bennington, VT 05257

  Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

  Nicholas Charest Maple Leaf Realty

  100 McCarthy Acres, North Bennington, VT 05257
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  /48

  $650,000 Sold May 06, 2025

  • 1,738 Sq Ft
  • $374/SF
  • 192 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  1516 W Mountain Rd, Shaftsbury, VT 05262

  Discover your dream retreat in this immaculate 3-bedroom, 3-bath, single level home, nestled on over 4 acres of breathtaking landscape. Enjoy expansive mountain views of the Taconic range, Bennington Monument, and Mount Graylock. Relax on the spacious deck or in the screened-in porch, soaking in the stunning vistas. This updated one-level home, features hardwood floors throughout and an open

  Margretta Fischer Wohler Realty Group

  1516 W Mountain Rd, Shaftsbury, VT 05262
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  /12

  Est $349,180 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,123 Sq Ft

  140 Church St, Shaftsbury, VT 05262

  140 Church St, Shaftsbury, VT 05262
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  /24

  $42,000

  • Land
  • 0.48 Acre
  • $87,500 per Acre

  26 Asa's Way, Bennington, VT 05257

  Walking trails, a paved road, underground utilities, and water/sewer at the street, what more could you ask for? Situated high on Asa's Way, almost a half acre of slightly sloping and level lot is ready to build on. Over 200 feet of road frontage allows for many home designs; from a hillside house that maximizes the southerly sun, to a modern bungalow perched on a flat landing, bring your ideas!

  Angela Bevin Maple Leaf Realty

  26 Asa's Way, Bennington, VT 05257

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