Bennington County VT Homes for Sale

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  /59

  $1,050,000

  • 3 Beds
  • 3.5 Baths
  • 2,160 Sq Ft

  10 Middle Ridge Rd Unit 25, Winhall, VT 05155

  A Rare Stratton Resort Opportunity in Fox Chapel Perfectly situated in the heart of Stratton Mountain Resort, this exceptional Fox Chapel townhouse offers the ultimate mountain lifestyle with walkable access to the Gondola, Stratton Village shops, and dining. Designed in classic chalet style, this three-story residence features a dramatic open floor plan highlighted by a floor-to-ceiling grand

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  10 Middle Ridge Rd Unit 25, Winhall, VT 05155
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  /60

  $995,000

  • 6 Beds
  • 7 Baths
  • 5,400 Sq Ft

  2001 Depot St, Manchester Center, VT 05255

  LOCATION, LOCATION: Just 8 minutes to Bromley and 20 minutes to Stratton, yet close to Manchester’s dining, shopping, fishing, golf, and the Horse Show. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bath retreat offers over 5,400 sq ft on 3.2 private acres—ideal as a primary home, vacation getaway, or rental investment. With a strong history as a

  Steven Bryant TPW Real Estate

  2001 Depot St, Manchester Center, VT 05255
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  /45

  $995,000

  • 13 Beds
  • 12 Baths
  • 8,594 Sq Ft

  2759 Vt Route 11, Peru, VT 05152

  Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2759 Vt Route 11, Peru, VT 05152
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  /6

  $35,000

  • Land
  • 1.7 Acres
  • $20,588 per Acre

  159 Oberdorf Rd, Readsboro, VT 05350

  Escape to the mountains with this ready-to-build 1.7-acre lot in scenic Alpenwald Village! Nestled beside National Forest land and bordered by a charming brook along the northern edge, this property offers a peaceful natural setting with endless outdoor adventure at your doorstep. Enjoy direct access to VAST snowmobile and VASA ATV trails, nearby hiking and mountain biking, and Dutch Hill for

  Lindsey Martin Maple Leaf Realty

  159 Oberdorf Rd, Readsboro, VT 05350
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  /60

  $5,250,000

  • 9 Beds
  • 10 Baths
  • 7,900 Sq Ft

  1184 E Manchester Rd, Manchester, VT 05255

  Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  1184 E Manchester Rd, Manchester, VT 05255
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  /32

  $295,000

  • 1 Bed
  • 1.5 Baths
  • 1,680 Sq Ft

  318 North St, Bennington, VT 05201

  A former florist shop for 2 decades, this mixed-use property is now a blank slate ready for your vision. Zoning allows for retail, food/drink/entertainment, gallery or studio, personal or professional services, to multi-family or single-family residential. First floor and basement previously served as retail space, but with the walk-in cooler now removed, the main level feels significantly

  Jenifer Prouty Hoffman Hoffman Real Estate

  318 North St, Bennington, VT 05201
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  /25

  $98,999 New Construction

  • 2 Beds
  • 2 Baths
  • 825 Sq Ft

  78 Ethans Way, Bennington, VT 05201

  Welcome to 78 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polomodel manufactured home offers 2 bedrooms, 2 bathrooms, and 825 sq. ft. 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 energy-efficient

  Kate Barry EXP Realty

  78 Ethans Way, Bennington, VT 05201
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  /7

  $997,000

  • Land
  • 0.53 Acre
  • $1,881,132 per Acre

  153 Northside Dr, Bennington, VT 05201

  Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

  Lori Hurley Four Corner Properties LLC

  153 Northside Dr, Bennington, VT 05201
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  /9

  $295,000

  • 4 Beds
  • 2 Baths
  • 2,206 Sq Ft

  116 S Branch St Unit 118, Bennington, VT 05201

  Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

  Julie Glover Mahar McCarthy Real Estate

  116 S Branch St Unit 118, Bennington, VT 05201
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  /13

  $295,000

  • 4 Beds
  • 2 Baths
  • 2,022 Sq Ft

  124 S Branch St, Bennington, VT 05201

  Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups—perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street. With

  Julie Glover Mahar McCarthy Real Estate

  124 S Branch St, Bennington, VT 05201
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  /5

  $350,000 New Construction

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

  525 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. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy

  Lilli West Maple Leaf Realty

  525 Jennings Brook Dr, Bennington, VT 05201
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  /13

  $475,000

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

  10 Byington Unit F1, Winhall, VT 05340

  The first showings will be at the open house 3/8/26 from 2-4 pm.Welcome to your Vermont mountain retreat in the sought-after Winhall Acres community. This charming 3-bedroom plus loft, 2-bath condominium chalet offers the perfect blend of comfort, convenience, and year-round adventure.The home features a smart and inviting layout designed for both relaxing and entertaining. Three

  Carrie Mathews Winhall Real Estate

  10 Byington Unit F1, Winhall, VT 05340
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  /45

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  9 Lower Taylor Hill Rd, Winhall, VT 05340

  Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

  Timothy Mich Doddridge Stratton Real Estate

  9 Lower Taylor Hill Rd, Winhall, VT 05340
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  /59

  $3,475,000

  • 5 Beds
  • 6 Baths
  • 5,905 Sq Ft

  220 Camptown Rd, Manchester Center, VT 05255

  Set high on a hillside overlooking a picturesque horse farm, this exceptional Manchester property captures far-reaching mountain views and covetous privacy. Nearly 39 acres of sweeping lawn and open meadow transition into wooded terrain, with direct access to over 1,000 acres of conserved land leading to Mount Equinox and Myrick Mountain in the Equinox Highlands. Trails on the property and

  Christiane Carroccio TPW Real Estate

  220 Camptown Rd, Manchester Center, VT 05255
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  /9

  $27,500

  • Land
  • 1.2 Acres
  • $22,917 per Acre

  0 Bergrucken Ln Unit 5044034, Stamford, VT 05352

  Trade city sirens for wind-rustled maples on this gently wooded 1.2-acre lot tucked inside Alpenwald Village. Alpenwald, although deed restricted, the light protective covenants keep the area tidy without cramping your architectural imagination. Think A-Frame, modern farmhouse, or a passive solar cottage. Beyond the lot is access to trails that lace through the Green Mountain National Forest.

  Kelly Agrillo Southern Vermont Realty Group

  0 Bergrucken Ln Unit 5044034, Stamford, VT 05352
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  /43

  $2,100,000

  • 4 Beds
  • 3 Baths
  • 3,780 Sq Ft

  1228 Skiparee Rd, Pownal, VT 05260

  Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

  Christiane Carroccio TPW Real Estate

  1228 Skiparee Rd, Pownal, VT 05260
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  /60

  $579,900

  • 1 Bed
  • 1 Bath
  • 2,529 Sq Ft

  126 Simeon Dean Rd, Shaftsbury, VT 05262

  Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft & Heated Tack Rm added, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete

  Denise Byers Green Mountain Premiere Properties

  126 Simeon Dean Rd, Shaftsbury, VT 05262
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  /12

  $399,500

  • Land
  • 2.7 Acres
  • $147,963 per Acre

  2937 Dorset Rd W, Dorset, VT 05251

  Prime Buildable Lot in Dorset! Embrace the Best of All Worlds! Discover a rare opportunity to own a ready-to-build lot in the heart of Dorset, perfectly positioned to offer unparalleled access to the town's finest attractions. Just moments from scenic hiking trails, the picturesque Dorset Green, and the esteemed Dorset Field Club, this property is your gateway to a lifestyle of outdoor adventure

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  2937 Dorset Rd W, Dorset, VT 05251
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  /23

  $249,000

  • Land
  • 17.6 Acres
  • $14,148 per Acre

  88 Cedar Ln, Peru, VT 05152

  Tucked away in the heart of the Green Mountains, this stunning 17.60-acre parcel in picturesque Peru, Vermont, is a rare opportunity to create your dream retreat. The land is richly wooded, offering a serene natural setting filled with mature trees and gently rolling terrain that promises a spectacular display of fall foliage—an ever-changing canvas of vibrant reds, oranges, and golds each

  Joe Castaluccio Winhall Real Estate

  88 Cedar Ln, Peru, VT 05152
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  /27

  $290,000

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

  196 Granger Hollow Rd, North Bennington, VT 05257

  Currently being used as a primary home with in-law rental 2nd home, this property could easily transition into a 2 unit multifamily with 2 separate houses with your tenants paying all utilities responsible for their own plowing and yard upkeep. This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large

  Steve Schoppmeyer BHG Masiello Brattleboro

  196 Granger Hollow Rd, North Bennington, VT 05257
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  /14

  $2,500,000

  • Land
  • 227 Acres
  • $11,013 per Acre

  00 Vermont 11, Peru, VT 05152

  227 acre offering in Peru Vermont combining a 199 acre parcel bordering Green Mountain National Forest and a 28 acre parcel with views of Stratton, Bromley and Magic Mountains. Southern exposure and varied terrain provide excellent natural light, privacy and long range Green Mountain vistas. The property offers exceptional scale and flexibility suitable for a private estate, family compound or

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
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  /15

  $169,000

  • 2 Beds
  • 1 Bath
  • 748 Sq Ft

  415 County St, Bennington, VT 05201

  The transformation inside this home is nothing short of spectacular. This move-in-ready, one-floor living bungalow has been thoughtfully designed to maximize every square foot, including a brand-new bathroom and updated finishes. From the moment you step into the entrance that was converted from a front porch into a versatile mudroom or home office—you’ll feel the quality. The layout is a

  Lori Hurley Four Corner Properties LLC

  415 County St, Bennington, VT 05201
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  /40

  $439,500

  • 4 Beds
  • 3.5 Baths
  • 3,861 Sq Ft

  120 Village St, East Dorset, VT 05253

  Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

  Dana Kingsley Josiah Allen Real Estate, Inc.

  120 Village St, East Dorset, VT 05253
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  /3

  $109,000

  • Land
  • 17 Acres
  • $6,412 per Acre

  00 Bill T Dr, Readsboro, VT 05350

  Escape to the Green Mountains with this beautiful 17-acre parcel located at the end of a town-maintained road in scenic Readsboro, Vermont. This private property offers the perfect mix of seclusion and convenience, surrounded by nature and outdoor recreation opportunities. At the rear of the property, you’ll find a serene beaver pond that attracts moose, birds, and other local wildlife—an ideal

  Samantha Decker Deerfield Valley Real Estate

  00 Bill T Dr, Readsboro, VT 05350
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  /36

  $375,000

  • 3 Beds
  • 1.5 Baths
  • 1,748 Sq Ft

  695 Dermody Rd, Bennington, VT 05201

  This inviting ranch has been thoughtfully cared for and filled with warmth throughout. What truly sets it apart is the location, offering wide, beautiful views you can enjoy everyday. The level lot provides plenty of space for gardening, outdoor gatherings, or simply relaxing on the back deck with a morning cup of coffee, or an evening star gazing. With generous road frontage, the possibilities

  Monique Geannelis Mahar McCarthy Real Estate

  695 Dermody Rd, Bennington, VT 05201
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  /44

  $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 museums

  Colleen Zajac MONARCH REALTY, INC.

  1138 Main Rd, Stamford, VT 05352
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  /58

  $1,950,000

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft

  1086 West Rd, Bennington, VT 05201

  Built in 1866, this French Provençal–inspired stone estate is a rare and distinguished offering, blending historic grandeur with pastoral beauty on 94.56 acres just outside historic Bennington, Vermont. Commanding sweeping mountain views, the property delivers exceptional privacy while remaining conveniently close to town amenities. The main residence offers 9 bedrooms and 7 bathrooms,

  Kelley Mccarthy Mahar McCarthy Real Estate

  1086 West Rd, Bennington, VT 05201
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  /37

  $499,999

  • 4 Beds
  • 3 Baths
  • 3,504 Sq Ft

  636 Tunnel St, Readsboro, VT 05350

  Almost there! This owner has taken a traditional farmhouse and transformed it into an amazing home full of style and grace. There are many ways to consider this home...over 3500 square feet of single family living with 4 bedrooms (or even 5) and 3 baths...live on one floor, AIR B&B all or part of the other floor....rent both levels and use as a vacation home on off seasons. The kitchen is large

  Christine Lewis Brattleboro Area Realty

  636 Tunnel St, Readsboro, VT 05350
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  /37

  $629,000

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

  1649 E Manchester Rd, Manchester Center, VT 05255

  The most desirable homes are the ones that feel both beautifully removed and effortlessly connected. Privately set just moments from Manchester's boutiques, dining, and year-round recreation, this five bedroom, two bath Cape offers a rare sense of ease, pairing a peaceful setting with exceptional proximity to town. Thoughtfully updated and move-in ready, the home is as inviting as it is

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

  1649 E Manchester Rd, Manchester Center, VT 05255
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  /29

  $699,000

  • 3 Beds
  • 3 Baths
  • 2,317 Sq Ft

  9 F Cobble Ridge Rd, Winhall, VT 05340

  Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy

  Carrie Mathews Winhall Real Estate

  9 F Cobble Ridge Rd, Winhall, VT 05340
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  /42

  $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 throughout. Soaring

  Britt Wohler

  932 Mcnamara Rd, Dorset, VT 05251
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  /23

  $349,900

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  773 Oberdorf Rd, Readsboro, VT 05350

  Discover cozy mountain living in this charming Alpenwald chalet, where rustic character meets thoughtful modern updates. Nestled among the trees, this inviting retreat offers a bright, open floor plan filled with natural light from expansive windows and sliding glass doors. Recently remodeled, the kitchen and both full bathrooms bring a fresh, updated feel, while a comfortable bar area adds the

  Sean Taylor Moresi Real Estate Partners

  773 Oberdorf Rd, Readsboro, VT 05350
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  /40

  $6,900,000

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft

  515 W Fields Rd, Manchester, VT 05254

  Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rareand exceptional 5-bedroom, 6-bathroom home....The creative design of Architect Ramsey Gourd and Master Builder Mark Breen, well knownas two of Southern Vermont's

  Sunny Breen Josiah Allen Real Estate, Inc.

  515 W Fields Rd, Manchester, VT 05254
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  /10

  $342,000

  • Land
  • 28.5 Acres
  • $12,000 per Acre

  11 Old County Rd E, Londonderry, VT 05148

  A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  11 Old County Rd E, Londonderry, VT 05148
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  /12

  $299,999

  • Land
  • 10.05 Acres
  • $29,851 per Acre

  00 Garden Loop Rd, Winhall, VT 05340

  The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

  David White OwnerEntry.com

  00 Garden Loop Rd, Winhall, VT 05340
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  /24

  $1,200,000

  • 1 Bath
  • 950 Sq Ft

  109 Winhall Hollow Rd, Winhall, VT 05340

  Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  109 Winhall Hollow Rd, Winhall, VT 05340
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  /43

  $1,895,000

  • 6 Beds
  • 5.5 Baths
  • 5,178 Sq Ft

  144 Taconic Rd, Manchester, VT 05255

  “The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

  Tom Deck Josiah Allen Real Estate, Inc.

  144 Taconic Rd, Manchester, VT 05255
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  /31

  $329,000

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft

  103 Norton St, Bennington, VT 05201

  Beautifully Renovated 4-Bedroom Home with Modern Upgrades! Welcome to this stunning, move-in ready home that has been fully renovated with care and style. Offering 4 spacious bedrooms, 2 brand-new bathrooms, and 1,728 square feet of thoughtfully designed living space, this home is the perfect blend of comfort and modern living.Step inside to find gleaming hardwood floors that flow throughout

  Timothy Corcoran Mahar McCarthy Real Estate

  103 Norton St, Bennington, VT 05201
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  /7

  $175,000

  • Land
  • 15.49 Acres
  • $11,298 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
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  /44

  $199,000

  • 2 Beds
  • 2.5 Baths
  • 1,156 Sq Ft

  106 Park St Unit 2, Bennington, VT 05201

  Freshly updated 2-story townhouse in a convenient downtown Bennington location! This 2BR home features brand new stainless steel appliances, new vinyl plank flooring, and a fresh interior paint palette throughout. The open-concept main level offers a bright kitchen, dining, and living area—perfect for everyday living and entertaining—along with a pantry, half bath, and dedicated laundry room for

  Vicki Wilson Maple Leaf Realty

  106 Park St Unit 2, Bennington, VT 05201

Showing Results 81 - 120, Page 3 of 6