Bennington County VT Homes for Sale

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  /40

  $1,699,000

  • 4 Beds
  • 4 Baths
  • 2,951 Sq Ft

  1949 South Rd, Peru, VT 05152

  Discover Berry Hill Farm, an exceptional Vermont estate where inspired design, extraordinary craftsmanship, and natural beauty come together in one remarkable setting. Offering privacy, versatility, and a deep connection to the landscape, this unique property encompasses 15.52 acres across two separately deeded parcels, creating a rare offering for a Southern Vermont retreat. The contemporary

  Helen Nault

  1949 South Rd, Peru, VT 05152
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  /47

  $1,500,000

  • Land
  • 38.57 Acres
  • $38,890 per Acre

  500 Nims Rd, Dorset, VT 05251

  This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

  Laura Beckwith Josiah Allen Real Estate, Inc.

  500 Nims Rd, Dorset, VT 05251
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  /27

  $179,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,485 Sq Ft

  432 South St Unit D2, Bennington, VT 05201

  Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

  Abi Gregorio

  432 South St Unit D2, Bennington, VT 05201
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  /2

  $4,177,625

  $802K PRICE DROP

  • 33,801 Sq Ft

  1000 Investors Ln, Manchester, VT 05255

  Exceptional opportunity to acquire a well-established Vermont investment portfolio consisting of 10 properties inclusive of 33 residential units and 2 commercial units located across the desirable communities of Brattleboro, Ludlow, Manchester, Cavendish, Shaftsbury, Proctorsville, and Chester. This diverse portfolio has been thoughtfully maintained and professionally managed, with many long-term

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  1000 Investors Ln, Manchester, VT 05255
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  /7

  $997,000

  • Land
  • 23,086 Sq Ft
  • $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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  /58

  $1,599,000

  • 4 Beds
  • 2.5 Baths
  • 5,403 Sq Ft

  525 Andrea Dr, Stamford, VT 05352

  Paradise Found!Exquisite Vermont Retreat. Follow the gravel road to the end and you will discover this amazing wonderfully protected and private home on 37 acres in the peaceful town of Stamford. The best of Vermont skiing, boating, hiking, winter and summer recreation as well as the shopping, dining, art, and culture of the Berkshires of Massachusetts are also just a short drive away. Bright

  Paul Harsch Harsch Associates

  525 Andrea Dr, Stamford, VT 05352
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  /52

  $2,285,000

  • 5 Beds
  • 4.5 Baths
  • 4,647 Sq Ft

  543 Lower Hollow Rd, Dorset, VT 05251

  A Serene Dorset Hollow Retreat Along the Mettowee RiverTucked into the storied Dorset Hollow, this 4.6-acre retreat enjoys 488 feet of Mettowee River frontage, offering a rare blend of tranquility, comfort, and timeless Vermont charm. Expansive mountain views and the soothing sounds of the river surround you—fall asleep each night to its calming presence. Multiple outdoor spaces include a

  Britt Wohler

  543 Lower Hollow Rd, Dorset, VT 05251
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  /9

  $269,000

  $26K PRICE DROP

  • 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

  $275,000

  $20K PRICE DROP

  • 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.

  Julie Glover Mahar McCarthy Real Estate

  124 S Branch St, Bennington, VT 05201
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  /32

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,878 Sq Ft

  32 Benson Fuller Dr, Bondville, VT 05340

  Embrace Vermont living with this fully furnished, 4-bedroom, 3.5-bath contemporary home located just minutes from Stratton Mountain Resort. Situated on a serene 1-acre lot along a quiet road, this move-in-ready sanctuary offers effortless mountain comfort, high-end entertaining space, and practical updates throughout. Quality architectural details welcome you into a bright main level boasting a

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  32 Benson Fuller Dr, Bondville, VT 05340
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  /8

  $199,000

  $51K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  924 Vt Route 7a, Shaftsbury, VT 05262

  Full of character and opportunity, this charming 2-bedroom, 2-bath home in Shaftsbury offers an affordable entry into homeownership or a fantastic addition to an investment portfolio. Once serving as the local post office, the property has a unique history and a cozy footprint that makes it ideal as a starter home, downsizing option, or rental property. Recent improvements include a beautifully

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  924 Vt Route 7a, Shaftsbury, VT 05262
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  /59

  $989,900

  • 4 Beds
  • 3 Baths
  • 5,697 Sq Ft

  66 Somerset Rd, Searsburg, VT 05363

  Six oversized garage bays across two multi-level outbuildings, direct access to Green Mountain National Forest, backyard waterfalls, and 5.4 private acres make this gated Southern Vermont retreat unlike anything else near Wilmington. Just five miles from downtown Wilmington and less than 12 miles from Mount Snow, the property combines substantial space for living and entertaining with exceptional

  Erica Reynolds Southern Vermont Realty Group

  66 Somerset Rd, Searsburg, VT 05363
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  /40

  $595,000

  $20K PRICE INCREASE

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

  23 Loop Rd Unit 10, Bondville, VT 05340

  Set among sun-dappled woodlands along a peaceful country road, this distinctive post-and-beam home captures the charm of a Vermont sugar shack with the warmth of a classic ski-country retreat. This furnished three bedroom, two bath home offers 1,416 sq ft of inviting living space, thoughtfully designed for both full-time living and memorable getaways. Inside, the vaulted Great Room immediately

  Diana Stugger Four Seasons Sotheby's Int'l Realty

  23 Loop Rd Unit 10, Bondville, VT 05340
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  /4

  $1,295,000

  • Land
  • 52.61 Acres
  • $24,615 per Acre

  00 Montgomery Rd, Pownal, VT 05261

  A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

  Ann Greenwood Alton + Westall Real Estate Agency, LLC

  00 Montgomery Rd, Pownal, VT 05261
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  /60

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 3,295 Sq Ft

  142 Schenkar Rd, Pownal, VT 05261

  Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home

  Erin McCormick KW Vermont

  142 Schenkar Rd, Pownal, VT 05261
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  /60

  $574,900

  $5K PRICE DROP

  • 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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  /27

  $645,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,432 Sq Ft

  4928 Main St Unit 2, Manchester Center, VT 05255

  Fabulous two bedroom two bath condominium converted in 2017 in the heart of Manchester Center. Many fine features: Marvin windows, hardwood flooring, central air conditioning, forced hot air heat, private second floor sundeck, mountain views. This one level second floor unit is accessed by private elevator and offers pretty mountain views through the oversized 9 foot windows. The living room has

  David Halligan Four Seasons Sotheby's Int'l Realty

  4928 Main St Unit 2, Manchester Center, VT 05255
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  /4

  $349,000

  • 3,637 Sq Ft

  710 Main St, Bennington, VT 05201

  Well-maintained four-unit property ideally located in downtown Bennington. This versatile multi-family offering features just the right amount of yard space for outdoor enjoyment, along with ample off-street parking. The property includes two one-bedroom units, one two-bedroom unit, and one spacious four-bedroom unit, providing a flexible mix of rental options. With a strong rental history and

  Dan Mason Perrott Realty

  710 Main St, Bennington, VT 05201
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  /52

  $179,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  130 Morgan St, Bennington, VT 05201

  200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities. Showings start 8/18/2026

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201
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  /60

  $1,850,000

  • 4 Beds
  • 3.5 Baths
  • 3,828 Sq Ft

  400 Spring Brook Rd, Arlington, VT 05250

  A once-in-a-generation estate, this 125 acre property offers the rare combination that you almost never find: true privacy, two residences, forest trails, cultivated grounds, and river frontage on the Battenkill. Nestled at the base of Red Mountain on a private road, with the far shore protected by parkland, the property feels like its own secluded world while remaining minutes from Manchester

  Emily Heyer Hoffman Real Estate

  400 Spring Brook Rd, Arlington, VT 05250
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  /52

  $299,000

  $10K PRICE INCREASE

  • 3 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  262 Union St, Bennington, VT 05201

  Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

  William Paquin Maple Leaf Real Estate

  262 Union St, Bennington, VT 05201
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  /12

  $399,500

  $11K PRICE DROP

  • 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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  /4

  $25,000

  $25K PRICE DROP

  • Land
  • 43,124 Sq Ft
  • $25,253 per Acre

  0 Route 30 Unit 5099207, Winhall, VT 05340

  Wooded one acre parcel off Rt 30 in Winhall, just past the west entrance to French Hollow Rd. and by Green Mountain National Forest and VTRT 30. This is a sloping /wooded parcel that extends down to the Mill Brook. There seems to be a nice plateau/bench as a possible build site........All Buyers should/must do their Own due diligence.

  Mike England Michael England Real Estate

  0 Route 30 Unit 5099207, Winhall, VT 05340
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  $215,000

  $20K PRICE DROP

  • 1,300 Sq Ft

  340 Pleasant St, Bennington, VT 05201

  Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with

  Melissa Nebelski Real Broker LLC

  340 Pleasant St, Bennington, VT 05201
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  /27

  $269,900

  $50K PRICE DROP

  • 2,190 Sq Ft

  196 Granger Hollow Rd, North Bennington, VT 05257

  Currently being used as a primary home a vacant 2nd home, this property could be either a single family residence with/without an in-law house or as 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

  Steve Schoppmeyer BHG Masiello Brattleboro

  196 Granger Hollow Rd, North Bennington, VT 05257
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  /24

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,035 Sq Ft

  84 Overlook Rd, East Dorset, VT 05253

  Commanding panoramic mountain views define this exceptional Dorset Overlook residence, where every room is designed to capture the beauty of Southern Vermont's ever-changing landscape. Bathed in natural light, the home's open floor plan creates an effortless flow between living, dining, and entertaining spaces, making everyday living as enjoyable as hosting family and friends.The thoughtfully

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

  84 Overlook Rd, East Dorset, VT 05253
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  /14

  $2,395,000

  $105K PRICE DROP

  • Land
  • 227 Acres
  • $10,551 per Acre

  00 Vermont 11, Peru, VT 05152

  Bordering Green Mountain National Forest with sweeping views of Stratton, Bromley, and Magic Mountains, this 227 +/- acre offering in Peru, Vermont captures the scale, privacy, and natural beauty that define Southern Vermont mountain living.Spanning two distinct parcels, the offering includes 199 +/- acres bordering National Forest land and a separate 28 +/- acre parcel positioned to capture

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  00 Vermont 11, Peru, VT 05152
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  /40

  $434,500

  $45K PRICE DROP

  • 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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  /18

  $79,000

  $30K PRICE DROP

  • Land
  • 17 Acres
  • $4,647 per Acre

  00 Bill T Dr, Readsboro, VT 05350

  Significant price reduction! This gently sloping 17acre parcel should not be overlooked. This property offers a dead-end location on a town-maintained road, providing you with privacy and convenience. Nestled in the charming town of Readsboro and surrounded by the beautiful Green Mountains, you will have easy access to VAST snowmobile trails and VASA ATV trails. Plus, you are just a stone's throw

  Michelle O'Neil Deerfield Valley Real Estate

  00 Bill T Dr, Readsboro, VT 05350
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  /13

  $1,295,000

  • Land
  • 52 Acres
  • $24,904 per Acre

  0 Montgomery Rd, Pownal, VT 05261

  A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  0 Montgomery Rd, Pownal, VT 05261
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  /49

  $650,000

  • 5 Beds
  • 3 Baths
  • 5,524 Sq Ft

  81 Honeysuckle Ln, North Bennington, VT 05257

  Kelley Mccarthy Mahar McCarthy Real Estate

  81 Honeysuckle Ln, North Bennington, VT 05257
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  /42

  $3,900,000

  • 5 Beds
  • 7 Baths
  • 11,736 Sq Ft

  2236 River Rd, Manchester, VT 05254

  Set on more than 18 picturesque acres along desirable River Road in Manchester Village, this extraordinary, converted farm offers a rare blend of historic character, modern comfort, & endless possibilities. Thoughtfully transformed into a multi-use residential compound, the property features four distinct living, working, & entertaining spaces, each with its own personality and purpose.

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

  2236 River Rd, Manchester, VT 05254
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  /52

  $850,000

  $120K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 5,764 Sq Ft

  24 Vt Route 11, Londonderry, VT 05148

  Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection. Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chef’s kitchen, sun-filled all-season

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  24 Vt Route 11, Londonderry, VT 05148
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  /37

  $575,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14 Marisa Ln, Dorset, VT 05251

  Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here.Step inside and discover an open floor plan that feels both spacious and inviting

  Julie Citron RE/MAX Four Seasons

  14 Marisa Ln, Dorset, VT 05251
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  /26

  $2,300,000

  • 5 Beds
  • 3.5 Baths
  • 3,332 Sq Ft

  241 High Hill Rd, Manchester Center, VT 05255

  Perched on a hillside in one of the area's most sought-after in-town locations, this special property offers a rare combination of privacy, breathtaking mountain views, and a picturesque pond, all just moments from local shops, restaurants, and amenities. Surrounded by established landscaping and filled with natural light, the home captures the beauty of its setting through expansive windows on

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

  241 High Hill Rd, Manchester Center, VT 05255
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  /35

  $939,000

  • 3,031 Sq Ft

  3191 Vermont 30, Dorset, VT 05251

  Dorset Village Investor's choice! Village Commercial... Currently Presenting a 5 unit, 3030 SF residence that can not be reproduced locally. This building has been lifted and a full (includes a small crawl) poured concrete foundation installed... dry as can be... clean as any basement can be hoped for! There are a mix of one bedrooms and studios... The configuration can be easily altered to

  Laura Beckwith Josiah Allen Real Estate, Inc.

  3191 Vermont 30, Dorset, VT 05251
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  /16

  $495,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255

  Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-burning fireplace.The

  Northshire Sales Group Real Broker LLC

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255
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  /38

  $575,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14A Marisa Ln, Dorset, VT 05251

  Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here.Step inside and discover an open floor plan that feels both spacious and inviting

  Julie Citron RE/MAX Four Seasons

  14A Marisa Ln, Dorset, VT 05251
• 

  

  /60

  $1,600,000

  • 5 Beds
  • 4.5 Baths
  • 4,243 Sq Ft

  397 Fern Hill, Dorset, VT 05251

  Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

  Laura Beckwith Josiah Allen Real Estate, Inc.

  397 Fern Hill, Dorset, VT 05251
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  /41

  $1,425,000

  $100K PRICE DROP

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

  932 Mcnamara Rd, Dorset, VT 05251

  It's SUMMER in Dorset and Manchester Vermont and this home screams opportunity ! NEW ROOF and exterior maintenance all updated for new owner! Situated in a most beautiful 5.4 acre setting of mature trees, landscaping and privacy, tucked away at the end of a gently curved, tree-lined drive. Located just over the Manchester Dorset town line, where Three Maple Drive becomes MacNamara, you'll

  Britt Wohler

  932 Mcnamara Rd, Dorset, VT 05251

Showing Results 81 - 120, Page 3 of 7