Windham County VT Homes for Sale

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  /30

  $289,000

  • 1 Bed
  • 1 Bath
  • 2,000 Sq Ft

  116 Birge St Unit 3, Brattleboro, VT 05301

  Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings, cool factory-style

  Liz LaVorgna Brattleboro Area Realty

  116 Birge St Unit 3, Brattleboro, VT 05301
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  /41

  $875,000

  • 7 Beds
  • 6.5 Baths
  • 1,152 Sq Ft

  136 Vermont Route 100, Dover, VT 05356

  Residential Property with Income Potential Near Mount Snow Discover a rare opportunity to own a versatile residential property with multiple income streams, located just minutes from the village of West Dover and the Mount Snow Resort area. Whether used as a primary residence, second home, or investment property, this offering provides exceptional flexibility. The main residence features a

  Cyd Scott Cohn & Company

  136 Vermont Route 100, Dover, VT 05356
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  /15

  $530,000

  • Land
  • 30 Acres
  • $17,667 per Acre

  00 W Hill Rd S, Jamaica, VT 05343

  Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

  Jacki Murano Southern Vermont Realty Group

  00 W Hill Rd S, Jamaica, VT 05343
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  /16

  $410,000

  • 3 Beds
  • 2 Baths
  • 2,192 Sq Ft

  69 Colonial Ridge Rd, West Dover, VT 05356

  Located in the highly desirable Dover Hills section of Dover, this 3 bedroom plus loft den has been well maintained by the original owners and upgraded with a metal roof. The foyer mudroom with a second entrance into the main living area allows you to unload your ski gear there or through the outside entrance to the basement. You enter into the main living area with a cozy wood burning fireplace,

  Nadine Coffey Berkley & Veller Greenwood/Dover

  69 Colonial Ridge Rd, West Dover, VT 05356
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  /30

  $139,000

  • Land
  • 20.1 Acres
  • $6,915 per Acre

  251 Phillips Hill Rd, West Halifax, VT 05358

  Discover 20.10 acres of land in Halifax, Vermont, just a short drive to Greenfield, MA, and from skiing at Mount Snow and The Hermitage Club. This property consists of two separately deeded building lots, offering flexibility for two homes or a single retreat. Enjoy seasonal mountain views, peaceful surroundings, and direct access from a quiet country road. In the warmer months, take advantage of

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  251 Phillips Hill Rd, West Halifax, VT 05358
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  /29

  $249,000

  • 3 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  4106 Vt Route 30, Jamaica, VT 05343

  Built in 1840, this charming home has long been a part of Jamaica’s rich history. Thoughtfully updated for modern living, it features a brand-new septic system, a renovated kitchen with granite countertops, and spacious rooms filled with natural light. Perfectly located just a short walk to town and Jamaica State Park, and only 10 miles from Stratton’s lifts, this property offers the ideal blend

  Carrie Mathews Winhall Real Estate

  4106 Vt Route 30, Jamaica, VT 05343
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  /59

  $275,000

  • 2 Beds
  • 1 Bath
  • 715 Sq Ft

  81 Parish Hill Rd, Newfane, VT 05345

  Nestled in the hills of South Newfane, Vermont, this off-grid property offers the perfect balance of seclusion, recreation, and comfort. Set on 22.32± acres of mixed timberland, the land features a meandering creek, wildlife habitat, and excellent hunting opportunities for deer and turkey. A 715 sq. ft. cabin, approximately 80% complete, serves as the centerpiece of the property. Built with a

  Chad Bruyette Whitetail Properties Real Estate, LLC

  81 Parish Hill Rd, Newfane, VT 05345
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  /41

  $1,495,000

  • 4 Beds
  • 3.5 Baths
  • 4,153 Sq Ft

  487 Vermont Route 100, Londonderry, VT 05148

  Set on nine acres, this inviting three bedroom brick home offers a rare blend of comfort, space, and rural charm. The main level features a large primary bedroom, with a beautiful full bathroom and walk in closet. Each room on the main level you'll find bright and comfortable living spaces and a beautiful sunroom that overlooks the surrounding fields. Upstairs, two spacious bedrooms share a

  Jamie Wylie Stratton Real Estate

  487 Vermont Route 100, Londonderry, VT 05148
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  /25

  $365,000

  • 5 Beds
  • 3 Baths
  • 2,254 Sq Ft

  85 Stockwell Dr, Brattleboro, VT 05301

  Sweet! This 5 bedroom /3 bath home is located in one of our most sought after neighborhoods, is newly remodeled, has 2 pellet stoves for economical heat and a nice back deck. Lots of opportunities to garden, relax in a hammock or play with pets. Flexible floor plan is perfect for at home workers, multigenerational living and aging in place. Hop the MOOVER and take a ride downtown, to Memorial

  Christine Lewis Brattleboro Area Realty

  85 Stockwell Dr, Brattleboro, VT 05301
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  /19

  $469,000

  • 2 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363

  Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363
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  /50

  $435,000

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  27 Country Ct, Wilmington, VT 05363

  Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous

  Janet Boyd Boyd Real Estate

  27 Country Ct, Wilmington, VT 05363
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  /14

  $279,000

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  8 Happy Haven Rd, Wilmington, VT 05363

  Conveniently located to village center, elementary school, lakes and trails. This riverfront home is waiting for a facelift! Three bedrooms, 2 bathrooms, living room, kitchen with a dining area with siders to a deck over looking the Deerfield River. Room downstairs for a hobby or craft room and a family room with a gas fireplace. Newer hot water tank and furnace. Room for gardens and a two car

  Janet Boyd Boyd Real Estate

  8 Happy Haven Rd, Wilmington, VT 05363
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  /44

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  24 Antler Loop, West Dover, VT 05356

  This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views.

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  24 Antler Loop, West Dover, VT 05356
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  /3

  $299,000

  • Land
  • 0.84 Acre
  • $355,952 per Acre

  8 B Freestyle Cir, Dover, VT 05356

  Ski in and out at Mount Snow from one of the last two buildable lots on the mountain. If you understand the convenience of slopeside living this could be the location for you to build your dream home. This building site is part of the TrailsEdge PUD, sharing in their utilities and ski access to/from Mount Snow through the Snowdance Village ski trails. Note that this is the larger of 2 lots

  John Redd Skihome Realty

  8 B Freestyle Cir, Dover, VT 05356
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  /33

  $390,000

  • 3 Beds
  • 1.5 Baths
  • 2,208 Sq Ft

  440 Stratton Arlington Rd, Stratton, VT 05360

  Experience the charm of owning a chalet in Vermont’s sought-after Stratton area, ideally located between Stratton Mountain and Mount Snow for easy ski access. Recent road improvements ensure smooth travel year-round. Outdoor lovers will enjoy nearby trails for hiking, snowmobiling, and snowshoeing, making this an ideal retreat for both relaxation and adventure. The home features a finished

  Mike England Michael England Real Estate

  440 Stratton Arlington Rd, Stratton, VT 05360
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  /45

  $380,000

  • 5 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  1033 Burrington Hill Rd, Whitingham, VT 05361

  Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's

  Monique White Deerfield Valley Real Estate

  1033 Burrington Hill Rd, Whitingham, VT 05361
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  /39

  $925,000

  • 5 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  3715 Route 11, Londonderry, VT 05148

  Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws sink, and upscale

  Cheyanne Pugliese

  3715 Route 11, Londonderry, VT 05148
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  /23

  $1,150,000

  • 6,442 Sq Ft

  69-71 Elliot St, Brattleboro, VT 05301

  Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

  Erica Reynolds Southern Vermont Realty Group

  69-71 Elliot St, Brattleboro, VT 05301
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  /45

  $115,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  26 Lynwood Dr, Brattleboro, VT 05301

  Don’t miss this unique opportunity to own a mobile home in a Vermont park with features that truly set it apart. Situated on a large lot, this home offers a full concrete foundation with a walkout basement—a rare find that provides exceptional storage, workshop space, or future finishing potential.The interior features a highly functional floor plan, with the kitchen, living room, and dining

  Jon Tourville

  26 Lynwood Dr, Brattleboro, VT 05301
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  /26

  $179,000

  • 4 Beds
  • 2 Baths
  • 2,470 Sq Ft

  1153 Rockingham Rd, Town of Rockingham, VT 05101

  Calling all investors and handy people! This is your opportunity to bring a classic property back to its former glory. Set on approximately 8.67 acres with frontage along the Williams River and Route 103, the location offers endless potential for a variety of uses. The spacious home appears to have solid bones but will require rehabilitation to restore its charm. A concrete slab is already in

  Chelsea Richardson Barrett and Valley Associates Inc.

  1153 Rockingham Rd, Town of Rockingham, VT 05101
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  /59

  $2,398,000

  • 4 Beds
  • 4 Baths
  • 3,585 Sq Ft

  127 Fannie Hill Dr, Wilmington, VT 05363

  Welcome to 127 Fannie Hill Road, an exceptional mountain retreat ideally located adjacent to The Hermitage Club in Wilmington, Vermont. This stunning 4 bedroom, (with two bonus bunk rooms) 4 bathroom home artfully blends modern mountain living with rustic charm. Featuring a thoughtful mix of materials which include reclaimed barn board, sleek corrugated metal, and contemporary cable railing this

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  127 Fannie Hill Dr, Wilmington, VT 05363
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  /15

  $305,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  5 First Ln Unit 1, Wilmington, VT 05363

  Owner open to offers. Lovely 2 bedroom condo as close as you can get to the 1st tee at the Haystack Golf Club, with winter views over the course to the mountains and sunsets beyond. This practical unit sits conveniently right on one of the best courses in New England, and a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. Inside you are

  Adam Palmiter Berkley & Veller Greenwood/Dover

  5 First Ln Unit 1, Wilmington, VT 05363
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  /38

  $749,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  717 Horsenail Hill Rd, Chester, VT 05143

  Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

  Robin Apps Four Seasons Sotheby's Int'l Realty

  717 Horsenail Hill Rd, Chester, VT 05143
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  /39

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  156 Mountain View Rd, Wilmington, VT 05363

  This charming Cape-style home offers three bedrooms and two full baths across the first two floors, featuring bamboo hardwood floors throughout and abundant natural light. Upstairs bedrooms have built in dressers. The living room boasts a cozy gas fireplace and flows seamlessly into the open-concept kitchen and dining area. A MAJOR highlight is the deeded lake rights to the picturesque Lake

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  156 Mountain View Rd, Wilmington, VT 05363
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  /20

  $179,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  7139 Vermont Route 100, Whitingham, VT 05361

  This cozy two bedroom, one bath cottage with vaulted wood ceilings is just steps away from Lake Whitingham! Enjoy a low maintenance get-away with an inviting living room and kitchen. This charming property offers the perfect escape for summer and winter enjoyment! The heart of the home is open and inviting where cold winter nights are made comfortable with an efficient propane heater. The simple,

  Casey Scott Southern Vermont Realty Group

  7139 Vermont Route 100, Whitingham, VT 05361
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  /31

  $33,500

  • 1 Bed
  • 2 Baths
  • 709 Sq Ft

  145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units; Studio unit (145) Queen murphy bed, kitchenette, full bathroom and a balcony. Hotel unit (147) Two queen beds, full bathroom and balcony. Units are located the mountain side of the hotel just down the hallway from the Spa, ski locker, health club and pool.. Lock out units

  Kelly Agrillo Southern Vermont Realty Group

  145/47 Qtr.1,89 Grand Summit Way, Dover, VT 05356
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  /12

  $249,000

  • Land
  • 19.6 Acres
  • $12,704 per Acre

  227 Gault Rd, Wardsboro, VT 05355

  This property is ready for you to push the pedal down and Go. All the engineering work has been done! There is an inground 3 bedroom septic system, a drilled well and a long gravel driveway with culverts.With almost half of the 19 acres being cleared, there is massive solar potential here for off the grid living. There is a large shed/cabin at the beginning of the driveway, which you could

  Victoria Woods Brattleboro Area Realty

  227 Gault Rd, Wardsboro, VT 05355
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  /21

  $849,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,564 Sq Ft

  4 Breezy Way, West Dover, VT 05356

  Brand new construction ski home just south of the Mount Snow ski resort recently finished for immediate use. This convenient location has MOOver shuttle service at the end of the street to and from the mountain, easy access to great restaurants and coffee shops, and direct snowmobile trail access, in addition to ample parking and privacy. The home was just finished by the developer and is ready

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4 Breezy Way, West Dover, VT 05356
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  /29

  $1,249,000

  • 4 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  3F Slalom Dr, Dover, VT 05356

  Just steps from the Mount Snow ski trail, this impeccably maintained 3,500 square foot luxury townhome is located in TrailsEdge, Mount Snow's exclusive ski-on/off community. Never again fight the traffic or pay for parking in the main base area when you can ski to and from your front door! As an end unit, this four-bedroom, 5-bath furnished townhome is a testament to luxury, with radiant heat

  Patricia Fitzpatrick Skihome Realty

  3F Slalom Dr, Dover, VT 05356
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  /26

  $740,000

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  8 Grouse Ln, Dover, VT 05356

  Escape to 8A Grouse Lane at Mount Snow, where timeless post-and-beam character meets modern comfort in a setting designed for all four seasons. This beautifully reimagined end-unit townhome was thoughtfully redesigned to create an open, inviting living space, complete with a striking gas-burning fireplace—the perfect spot to gather after a day on the mountain. Wake up to ridge-line views, sip

  Wilkie Bushby TPW Real Estate

  8 Grouse Ln, Dover, VT 05356
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  /37

  $36,500

  • 2 Beds
  • 2 Baths
  • 878 Sq Ft

  313 Qtr.1, 89 Grand Summit Way, Dover, VT 05356

  Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Mountainside two bedroom sleep 6 unit with a covered balcony. Kitchen, living room and queen sleeper sofa as well as a king bed in private bedroom on the first floor. Full bath with double sink vanity on the first floor. Lofted bedroom also has a king bed and a 3/4 bath . Benefits of Grand Summit ownership include the best

  Kelly Agrillo Southern Vermont Realty Group

  313 Qtr.1, 89 Grand Summit Way, Dover, VT 05356
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  /33

  $1,350,000

  • 4 Beds
  • 4 Baths
  • 2,753 Sq Ft

  7 Woodfern Run, Stratton, VT 05360

  Enjoy true trailside living in this luxury four-bedroom, four-bathroom townhouse at the highly sought-after Treetop development at Stratton. With mountain views and ski-in/ski-out access, you'll spend more time skiing, less time with logistics!Inside, the open living, dining, and kitchen area reflects classic Adirondack style, creating a warm and inviting space for gathering after a day on

  Christiane Carroccio TPW Real Estate

  7 Woodfern Run, Stratton, VT 05360
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  /34

  $469,900

  • 5 Beds
  • 4 Baths
  • 3,064 Sq Ft

  176 High St, Brattleboro, VT 05301

  Conveniently located in Brattleboro Center, this historic three-family home offers the perfect blend of Historic charm, and modern convenience. It is an ideal opportunity for an investor seeking profitable rental income or an owner-occupant looking to live on the main level while offsetting their mortgage with two additional rental units. The first-floor unit features high ceilings, French doors,

  Matt Waddington Hoffman Real Estate

  176 High St, Brattleboro, VT 05301
• 

  /2

  $59,900

  • Land
  • 1 Acre
  • $59,900 per Acre

  Lot 37 Woodsman Rd, Dover, VT 05356

  Super building lots up near the Dover Elementary School. Gentle sloping lots, with municipal sewer and underground telephone & electric. Prices reflect the quality of the view(s). Some with ski area(s) to the west and others with local ridgelines to south. Only moments from West Dover dining, shopping, and skiing. The Elementary School provides a fun campus for younger recreational fun. How many

  Michael Purcell Berkley & Veller Greenwood/Dover

  Lot 37 Woodsman Rd, Dover, VT 05356
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  /10

  $88,000

  • Land
  • 10.05 Acres
  • $8,756 per Acre

  Lot 3 North St, Dover, VT 05431

  Discover the perfect Vermont retreat on this 10.15 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape. Whether you envision a

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 3 North St, Dover, VT 05431
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  /31

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft

  68 E Brook Crossing, Wilmington, VT 05363

  Lovely updated chalet in the Chimney Hill community just outside the village of Wilmington and south of the Mount Snow ski resort. This home sits on a private lot with direct snowmobile trail access, great for summer hiking and biking, nearby access to Lake Whitingham, and is just a short drive into the downtown for shopping and dining. Inside you are treated to a vaulted living space with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  68 E Brook Crossing, Wilmington, VT 05363
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  /39

  $1,150,000

  • 4 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  3 Shannon Ridge Rd, Dover, VT 05356

  3 Shannon Ridge Road, West Dover, VT Private Mountain Retreat Between Mount Snow and The Hermitage Club Experience the perfect fusion of luxury, privacy, and adventure in this beautifully renovated 4,950 sq ft home set on 1.62 acres of tranquil Vermont countryside. Ideally positioned between Mount Snow and the private Hermitage Club, this home offers a rare opportunity for refined mountain living

  Derek Greene Derek Greene

  3 Shannon Ridge Rd, Dover, VT 05356
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  /31

  $699,000

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

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155

  Nestled right on the slopes of Stratton Mountain Resort, this two bedroom two ensuite bathroom condominium offers true ski-in/ski-out convenience for your winter getaway. You'll find yourself just steps from the Villager chairlift, beginner ski area as well as a stone's throw to the shops and restaurants in the Stratton Village. An open-concept living/dinning/kitchen area that features a stone

  Timothy Mich Doddridge Stratton Real Estate

  778 Stratton Mountain Access Rd Unit 2302, Stratton, VT 05155
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  /32

  $749,000

  • Land
  • 1.22 Acres
  • $613,934 per Acre

  Lot 2 Old Mill Ln, Wilmington, VT 05363

  Bring your own builder and discover an exceptional opportunity to own a 1.22-acre parcel of land located in an exclusive private neighborhood adjacent to the renowned private ski resort, The Hermitage Club in Wilmington, Vermont. This premium lot is the perfect canvas for creating your dream mountain retreat with custom homes to be crafted by your own builder or the Wadsworth Design Build. Enjoy

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  Lot 2 Old Mill Ln, Wilmington, VT 05363
• 

  

  /15

  $59,900

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  23 Deepwood Park, Brattleboro, VT 05301

  This home is in need of some TLC but well worth the effort! This home has bedrooms at each end for privacy and comfort. The rest of the home is open concept for amiable living and good conversation. Cook and visit! Sitting on a nice lot, a small bit of gardening and sun loving sitting on the deck. All homes in this park met energy efficiency standards when placed in the park! Walk the loop and

  Angela Sherman Brattleboro Area Realty

  23 Deepwood Park, Brattleboro, VT 05301

Showing Results 161 - 200, Page 5 of 10