Windham County VT Homes for Sale

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  /4

  $59,000

  • Land
  • 3.3 Acres
  • $17,879 per Acre

  0 Hunt Rd, Wardsboro, VT 05355

  Discover the perfect canvas for your Vermont dream home on this newly created 3.3-acre parcel in Wardsboro. Tucked away in a peaceful, private setting, you’ll enjoy the quiet beauty of the surrounding woods while still being within easy reach of some of Southern Vermont’s most sought-after destinations. Spend your winters skiing at Mount Snow or Stratton Mountain Resort, and take advantage of

  Mike Masters Four Seasons Sotheby's Int'l Realty

  0 Hunt Rd, Wardsboro, VT 05355
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  /30

  $399,000

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  1511 E Dover Rd, Wardsboro, VT 05355

  Tucked along a scenic stretch of East Dover Road, this charming Wardsboro property captures the essence of Vermont country living with the added bonus of easy access to some of Southern Vermont’s most sought-after destinations. Just a short drive to Mount Snow and Stratton Mountain Resort, this location is ideal for year-round recreation—from skiing and snowboarding in the winter to hiking,

  Mike Masters Four Seasons Sotheby's Int'l Realty

  1511 E Dover Rd, Wardsboro, VT 05355
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  /27

  $495,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 1,246 Sq Ft

  81 Chapin St, Brattleboro, VT 05301

  Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downtown Brattleboro, this 3-bedroom, 3-bath home blends historic craftsmanship with a cutting-edge deep-energy retrofit. Enjoy easy access to shops, dining, the Amtrak station, and the Retreat Trails from a peaceful, residential setting. Unlike typical historic renovations, this property underwent a

  John Hatton Berkley & Veller Greenwood Country

  81 Chapin St, Brattleboro, VT 05301
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  /17

  $1,450,000

  • Land
  • 201.4 Acres
  • $7,200 per Acre

  0 Forrester Rd Unit 5082418, Jamaica, VT 05360

  Own this large tract of land, over 200 acres that abuts over 1100 acres of Green Mountain National Forest property. This private setting is less than 3 miles to Stratton Mountain Resort with easy owned access on Forrester Pond. Current 18 acre gravel pit is being reclaimed and closed on this property. See the Vermont Land Use Permit 2W1316 online for further information. There are multiple

  Chris Lowe Lowe's Real Estate, LLC

  0 Forrester Rd Unit 5082418, Jamaica, VT 05360
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  /13

  $99,000

  • Land
  • 10.05 Acres
  • $9,851 per Acre

  78 Captain Copeland Rd, Dover, VT 05341

  Set on a quiet country road, this 10+ acre parcel offers an ideal blend of privacy and convenience with easy access to Mount Snow and year-round recreation. The property is currently wooded, providing a natural setting with the potential to open up attractive mountain views. Located in a desirable area close to skiing, hiking, and outdoor activities, this land presents a great opportunity for a

  Carrie Mathews Winhall Real Estate

  78 Captain Copeland Rd, Dover, VT 05341
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  /35

  $650,000

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft

  198 E Hill Rd, Wardsboro, VT 05355

  Gorgeous home with so many upgrades over the past five years! Updated kitchen with appliances, baths, new roof, windows, flooring, well pump, mini splits, high efficiency propane combo unit for heat and hot water, new pavement, three car detached garage, woodshed, fenced in doghouse area and so much more! These are just a few of the items this homeowner has done to improve the property. The home

  Julie Lowe Lowe's Real Estate, LLC

  198 E Hill Rd, Wardsboro, VT 05355
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  /29

  $335,000

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

  160 Sunny Acres Rd, Brattleboro, VT 05301

  Charming and well cared for ranch-style home offering comfortable one-level living. This inviting 3-bedroom, 2-bath property is move-in ready and the functional layout provides a bright living area, spacious bedrooms, and convenient everyday flow. Enjoy easy access to nearby schools, shopping, and local amenities while still having a cozy place to call home. A wonderful opportunity for those

  Claire Renaud Berkley & Veller Greenwood Country

  160 Sunny Acres Rd, Brattleboro, VT 05301
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  /2

  $55,000

  • Land
  • 0.5 Acre
  • $110,000 per Acre

  404 Fox Mountain Rd, Wilmington, VT 05363

  Top of the Hill. Build your dream home! One of 2 remaining lots on the new Fox Mt. Cul de Sac, and the only single lot. These have had recent soil tests showing the lot is suitable for a 3-bedroom home. The Lot is oriented to the Southwest, towards Bennington. Plus, enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding,

  Sigrid Pickering Chimney Hill Realty

  404 Fox Mountain Rd, Wilmington, VT 05363
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  /37

  $639,000

  • 4 Beds
  • 2.5 Baths
  • 2,573 Sq Ft

  11 Strawberry Hill, Brattleboro, VT 05301

  Beautifully sited on 1.9 acres just off Greenhill Parkway, this tastefully modernized 1940s cape blends architectural pedigree with thoughtful, high end updates. Designed by noted architect James Britton of Greenfield, MA - a contemporary of Royal Barry Wills and long admired for his classic New England forms - the home retains its classic original character, while offering a fully refreshed

  Dan Normandeau Berkley & Veller Greenwood Country

  11 Strawberry Hill, Brattleboro, VT 05301
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  /60

  $1,088,000

  • 6 Beds
  • 4.5 Baths
  • 5,828 Sq Ft

  151 Townshend Rd, Grafton, VT 05146

  Located in the heart of Grafton, Vermont, on a spacious one-acre, flat lot a quick stroll from town, this extensively renovated property offers exceptional flexibility and scale. The property is configured to allow division into two condominium-style living spaces plus a separate artist loft or accessory dwelling, each with its own entrance, creating versatile possibilities for expansive

  Erin McCormick KW Vermont

  151 Townshend Rd, Grafton, VT 05146
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  /60

  $795,000 Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 3,212 Sq Ft

  104 Juniper Ridge Rd, Brattleboro, VT 05301

  Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

  Kristen Ziter Taylor Brattleboro Area Realty

  104 Juniper Ridge Rd, Brattleboro, VT 05301
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  /23

  $260,000

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft

  429 Vt Route 30, Newfane, VT 05345

  Discover the perfect blend of charm and tranquility in this delightful 2-bedroom bungalow nestled in the heart of Newfane Village. Fresh paint throughout, this home is move-in ready and awaiting its next owner. You can sit on the side deck and enjoy a spacious, yard ideal for gardening, entertaining, or simply soaking in the sounds of nature with direct access to a picturesque stream. You can

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  429 Vt Route 30, Newfane, VT 05345
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  /32

  $24,500

  • 1 Bed
  • 2 Baths
  • 869 Sq Ft

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356

  This unique style, a sleep six condo, is located on the top floor of the hotel and features two levels, including a loft bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area has a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping four people. The spacious loft bedroom features a king-size bed, a large walk-in closet, and an

  Patricia Fitzpatrick Skihome Realty

  328, Qtr. 4 89 Grand Summit Way, Dover, VT 05356
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  /33

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft

  1829 W Jamaica Rd, Jamaica, VT 05343

  Vermont Charming! Tucked away along a peaceful river in Jamaica, Vermont this charming cape offers the perfect blend of privacy, character and convenience just 4 miles from Stratton Mountain Resort. With three bedrooms and one and three quarters baths, the home has been thoughtfully maintained and updated while preserving its classic New England charm. Recent upgrades to the kitchen and bathrooms

  

  Alison Cummings

  Cummings & Co

  (802) 471-3958

  1829 W Jamaica Rd, Jamaica, VT 05343
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  /31

  $619,000

  • 4 Beds
  • 4 Baths
  • 3,354 Sq Ft

  556 Sawmill Rd, Wardsboro, VT 05355

  Set on a private one-acre lot in Wardsboro, this well-designed 4-bedroom, 4-bathroom home with an attached garage offers over 3,000 square feet of living space and the perfect blend of comfort, style, and refined Vermont living. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property is perfectly positioned for year-round enjoyment — from winter

  Kim Meeker Southern Vermont Realty Group

  556 Sawmill Rd, Wardsboro, VT 05355
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  /8

  $74,900

  • Land
  • 1.1 Acres
  • $68,091 per Acre

  2 Johnson Hill, Dover, VT 05356

  Private 1.10 +/- Acre lot in Dover Hills VT. #WW-2-2888 Permit in place. Trinity Engineering did the engineering and the lot was approved for a three bedroom dwelling.

  Janet Boyd Boyd Real Estate

  2 Johnson Hill, Dover, VT 05356
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  /2

  $25,000

  • Land
  • 0.6 Acre
  • $41,667 per Acre

  28 Upper Howes Way, Wilmington, VT 05363

  Sweet Spot tucked away in a quiet corner of the Hill, ready for you to build your vacation getaway. Recent soil tests are favorable for a 3-bedroom house. Enjoy all the amenities Chimney Hill offers on its 1,200 Acre Resort Campus, including year-round swimming, seasonal tennis and pickleball, ice skating with a warming hut full of skates to use, hiking, biking, snowmobiling right from your house

  Sigrid Pickering Chimney Hill Realty

  28 Upper Howes Way, Wilmington, VT 05363
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  /23

  $470,000

  • 4 Beds
  • 2 Baths
  • 2,016 Sq Ft

  6D White Oaks Loop Unit 7, Dover, VT 05356

  Welcome to this spacious end-unit Timber Creek condominium, ideally located directly across from Mount Snow. This highly desirable community offers the perfect blend of mountain convenience and resort-style amenities, making it an exceptional year-round getaway. The main level features a welcoming mudroom entry with built-in bench and cubbies, opening into the dining area that flows seamlessly

  Monique White Deerfield Valley Real Estate

  6D White Oaks Loop Unit 7, Dover, VT 05356
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  /20

  $195,000

  • Land
  • 46.2 Acres
  • $4,221 per Acre

  1499 Josh Rd, Halifax, VT 05358

  Looking for true peace and tranquility? This 46.2-acre parcel faces South/SW and is located in a gorgeous remote valley with no road noise or any sound other than the sound of the crystal-clear brook crashing down the valley and the wind in the trees! The parcel does have some improvements including a modified camper with a 1000 gallon holding tank, existing gravel driveway off Josh Road (class

  Chris Long BHG Masiello Brattleboro

  1499 Josh Rd, Halifax, VT 05358
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  /5

  $72,000

  • Land
  • 6.21 Acres
  • $11,594 per Acre

  0 Crane Mountain Rd, Townshend, VT 05353

  Nestled on top of Townshend Acres this 6.21 acre surveyed lot offers a amazing opportunity to build your dream home . This mostly level wooded parcel has easy access to a town-maintained road near a neighborhood community . Outdoor activities abound ; hiking , hunting , snowmobiling all available ...outside your door. Minutes from four seasons resorts for skiing, music and biking. Convenient to

  Janet Lucier Barrett & Valley Assoc. Inc

  0 Crane Mountain Rd, Townshend, VT 05353
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  /37

  $795,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on almost 2 acres of landscaped grounds with lawns, stone walls & gardens, plus an adjoining 9.4 acre woodland lot with snowshoe trails in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
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  /51

  $244,900 Coming Soon

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

  72 Morningside Commons, Brattleboro, VT 05301

  Move up to a designer condo! Impeccable detailing by an IKEA design team raised this unit to a high level of quality. From the marble floor entrance to the architectural ceiling over the dining area to the custom kitchen and bathroom installations to the decorator lighting to the PAX closet wardrobe systems... it all speaks "beautiful". Newer features include a propane boiler and hot water heater

  Sally Fegley BHG Masiello Brattleboro

  72 Morningside Commons, Brattleboro, VT 05301
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  /17

  $285,000

  • 1 Bed
  • 1 Bath
  • 1,320 Sq Ft

  116 Birge St Unit 2, Brattleboro, VT 05301

  Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors—magical in combination and truly beautiful. A home, an artist loft...so many uses, so unique, so

  Christine Lewis Brattleboro Area Realty

  116 Birge St Unit 2, Brattleboro, VT 05301
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  /32

  $499,000

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins! Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  77 Buttonwood Dr, Brattleboro, VT 05301
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  /33

  $915,000

  • 3 Beds
  • 2.5 Baths
  • 1,529 Sq Ft

  761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360

  Originally a two bedroom and a one bedroom, this premiere condominium has been creatively converted into a very special family retreat. Completely renovated throughout----now three full bedrooms plus a den or office area, which could also serve as a fourth sleeping area--if so desired. You will also find two and a half beautifully renovated baths. The primary bedroom is oversized with a beautiful

  Edwin Kevil Stratton Real Estate

  761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360
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  /35

  $425,000

  • 4 Beds
  • 3 Baths
  • 4,488 Sq Ft

  35 School St, Bellows Falls, VT 05101

  This single-family Victorian home located in the village of Bellows Falls has lots of space for family and friends! Four bedrooms, three full baths, a second-floor laundry room, two kitchens, two living rooms, three bonus rooms, and even an area for a potential apartment above the one-car garage! The open-concept updated kitchen/living room offer plenty of storage and seating for everyone and

  Heather Gleim CENTURY 21 North East

  35 School St, Bellows Falls, VT 05101
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  /23

  $159,000

  • 1 Bed
  • 1 Bath
  • 592 Sq Ft

  219 High St Unit 3, Brattleboro, VT 05301

  Welcome to the effortless existence of condominium life with the rare addition of uniqueness. How nice to own a home while splitting the expenses with two other condo owners. Park in your driveway and follow a pretty stone path to your first-floor sanctuary. This efficient 592 sq ft space offers an open kitchen, dining area with a washer and dryer, living room, one bedroom, and a full bath. Share

  Kristen Ziter Taylor Brattleboro Area Realty

  219 High St Unit 3, Brattleboro, VT 05301
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  /18

  $249,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155

  Close to Magic, Bromley and Stratton! This two-bedroom, one bath condo with woodburning fireplace overlooks a beautiful brook and tennis court area. Private deck out back to enjoy some sun. Eat in kitchen with pass through countertop area opens into the living room. Manageable and spacious for a nice weekend getaway or make this your fulltime home. Just minutes to downtown with shopping, fuel,

  Julie Lowe Lowe's Real Estate, LLC

  3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155
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  /22

  $110,000

  • Land
  • 2.5 Acres
  • $44,000 per Acre

  69 Old Haven Ln, Putney, VT 05346

  Nestled in an idyllic setting at 69 Old Haven Lane, this exceptional building lot offers a rare opportunity to bypass the typical hurdles of new construction and start bringing your vision to life immediately. Located in a sought-after and peaceful pocket of Putney, this property perfectly balances the privacy of a country retreat with the convenience of an excellent location. Much of the

  Kate Barry EXP Realty

  69 Old Haven Ln, Putney, VT 05346
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  /12

  $159,500

  • 1 Bed
  • 1 Bath
  • 685 Sq Ft

  39 Brookside Dr Unit 7, Brattleboro, VT 05301

  Move right in! This condo has had some updates to include new scratch resistant vinyl plank flooring, new bathroom vanity, new kitchen range and freshly painted interior. Located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Shared basement with assigned storage space. Association fees include heat,

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 7, Brattleboro, VT 05301
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  /30

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  313 S Pine Banks Rd, Putney, VT 05346

  Experience the Magic of Putney, Vermont. Discover a private sanctuary in the heart of Vermont’s "Craft Capital." This meticulously maintained ranch offers the perfect blend of secluded country living and proximity to Putney’s vibrant cultural hub. Known for its world-class arts scene, organic farms, Yellow Barn Music, Next Stage Arts, Putney COOP, and iconic institutions like Sandglass Theater

  Thomas Dahlin Berkley & Veller Greenwood Country

  313 S Pine Banks Rd, Putney, VT 05346
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  /41

  $539,000

  • 4 Beds
  • 3 Baths
  • 2,948 Sq Ft

  196 Powder Mill Rd, Londonderry, VT 05148

  Mountain Escape with Multi-Generational Potential in Powder Mill Welcome to your mountain retreat in the heart of Vermont’s ski country! This spacious home in the desirable Powder Mill community has been thoughtfully updated with brand new kitchen cabinets, gleaming granite countertops, stainless steel appliances, and fresh carpet and flooring throughout. The flexible layout offers room for

  Katie Ladue Gilbert BHHS Verani Upper Valley

  196 Powder Mill Rd, Londonderry, VT 05148
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  /44

  $527,900

  • 4 Beds
  • 3 Baths
  • 1,850 Sq Ft

  37B Kingswood Rd, Dover, VT 05356

  Refined mountain luxury meets effortless four-season living in this impeccable Kingswood townhome, offering direct snowmobile trail access and private shuttle service to Mount Snow. Ideally positioned on the level portion of the development, this exceptional four-bedroom residence enjoys convenient trail access and a more expansive, usable, level rear yard—a rare and highly sought-after offering

  Michelle O'Neil Deerfield Valley Real Estate

  37B Kingswood Rd, Dover, VT 05356
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  /8

  $195,000

  • Land
  • 4.86 Acres
  • $40,123 per Acre

  0 Stoney Brook Rd, Londonderry, VT 05148

  4.86 acre building lot in Londonderry, Vermont with mountain views of Stratton and Bromley, offering privacy, elevation, and a compelling Southern Vermont setting. Access and building site are roughed in, and the property includes a State of Vermont wastewater permit for a 5 bedroom single family residence. Private setting, just minutes to Magic Mountain Ski Area and Londonderry Marketplace, with

  Kevin Moran Four Seasons Sotheby's Int'l Realty

  0 Stoney Brook Rd, Londonderry, VT 05148
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  /55

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  57 Oak Ln, Jamaica, VT 05343

  This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set

  Mike England Michael England Real Estate

  57 Oak Ln, Jamaica, VT 05343
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  /9

  $195,000

  • Land
  • 1.2 Acres
  • $162,500 per Acre

  4769 Pikes Falls Rd, Jamaica, VT 05143

  This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

  Rachel Febbie EXP Realty

  4769 Pikes Falls Rd, Jamaica, VT 05143
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  /60

  $725,000

  • 6 Beds
  • 3 Baths
  • 3,630 Sq Ft

  5 William Mundell Rd, South Newfane, VT 05351

  Just a short drive from the slopes of Mount Snow, this beautifully renovated 1800s Vermont farmhouse seamlessly blends historic charm with modern comfort. Situated on 7.5 picturesque acres just beyond the Dover town line in South Newfane, the property offers rolling pasture, classic stone walls, established gardens, and multiple outbuildings, all with easy access to nearby villages, lakes, and

  The Malley Group KW Vermont

  5 William Mundell Rd, South Newfane, VT 05351
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  /39

  $725,000

  • 5 Beds
  • 4 Baths
  • 2,962 Sq Ft

  250 Valley View Rd, Dover, VT 05356

  Unique, spacious, and just minutes to Mount Snow, this 5-bedroom, 4-bath home with a private pond is the kind of property buyers wait for. Whether for personal use, a vacation getaway, or short-term rental potential, it offers a setting to enjoy every season. Set on a beautiful 2-acre lot, the home features a large open-concept main living area with a cathedral ceiling and oversized windows that

  Melissa Nebelski Real Broker LLC

  250 Valley View Rd, Dover, VT 05356
• 

  

  /25

  $369,000

  • 3 Beds
  • 3 Baths
  • 1,750 Sq Ft

  36C N Access Rd Unit 703, Dover, VT 05356

  Spacious Snow Mountain Village townhome adjacent to the upper parking lots at Mount Snow ski resort. This unique large unit is one of only a handful of units with this size for the development. Inside you are greeted by a tiled mudroom area with laundry, and an adjacent large guest room with en suite full bath. The main level has a large open concept living room with wood burning fireplace and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  36C N Access Rd Unit 703, Dover, VT 05356
• 

  

  /23

  $189,000

  • Land
  • 3.6 Acres
  • $52,500 per Acre

  00 Lake Hill Rd, Whitingham, VT 05361

  Rare opportunity to own the “Spring Lot,” a beautiful 3.6-acre building site overlooking private Laurel Lake in Southern Vermont. This peaceful 17-acre lake is reserved exclusively for landowners—no motorboats allowed—perfect for kayaking, canoeing, fishing, and swimming, with the ability to add your own private dock. With preliminary soil testing & septic design showing positive results,

  Chad Lackey Deerfield Valley Real Estate

  00 Lake Hill Rd, Whitingham, VT 05361

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