30,481

Windham County, VT Homes

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    • /33

      Est $378,159 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,643 Sq Ft

      8 Castle Hill Rd, Wilmington, VT 05363

      8 Castle Hill Rd, Wilmington, VT 05363
  • /31

    $735,000

    • 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
  • /27

    $347,500 Sold Nov 06, 2025

    • 1,296 Sq Ft
    • $268/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1946

    15 Laurel St, Brattleboro, VT 05301

    LOVELY Laurel Street! This charming south-facing home is bathed in natural light and offers a thoughtful layout that combines the best of in-town living with a peaceful, out-of-town vibe. Enjoy a spacious backyard and a convenient enclosed porch/mudroom right off the attached garage—perfect for those chilly Vermont winters. The location couldn’t be better as it is close to town and nearby trails.

    Thomas Dahlin Berkley & Veller Greenwood Country

    15 Laurel St, Brattleboro, VT 05301
    • /30

      Est $430,309 Not Listed For Sale

      • 5 Beds
      • 2 Baths
      • 2,295 Sq Ft

      18 Castle Hill Rd, Wilmington, VT 05363

      18 Castle Hill Rd, Wilmington, VT 05363
  • /12

    $39,999

    • Land
    • 2 Acres
    • $20,000 per Acre

    14 Brickyard Rd, Dover, VT 05341

    Beautiful hillside parcel less than ten minutes from Mount Snow but outside the direct path of heavy tourist traffic. Brickyard Road is a winding packed-gravel road dotted sparsely with homes for full-time Dover residents, each with plenty of land and privacy. From the roadside the topography dips down about 5 feet, then quickly comes to a much more gradual slope which continues for approximately

    David White OwnerEntry.com

    14 Brickyard Rd, Dover, VT 05341
  • /18

    $120,000 Sold Nov 06, 2025

    • 888 Sq Ft
    • $135/SF
    • 99 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    15 Lynwood Dr, Brattleboro, VT 05301

    This is absolutely NOT your ordinary Mobile Home! Original year of frame is 1971 and is difficult to finance by lenders so the owner has done a HUGE PRICE DROP. Completely rebuilt from the floor up with wood framing, windows, doors and insulation. This fully fenced leased lot has two sheds, a 1 car garage building with tons of storage and a workshop building with its own mini-split for heat and

    Chris Long BHG Masiello Brattleboro

    15 Lynwood Dr, Brattleboro, VT 05301
    • /34

      Est $714,574 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,148 Sq Ft

      72 Castle Hill Rd, Wilmington, VT 05363

      72 Castle Hill Rd, Wilmington, VT 05363
  • /44

    $429,900

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft

    1909 Davidson Hill Rd, Westminster, VT 05158

    This charming Vermont country farmhouse offers peaceful privacy at the end of a quiet town road. Recently updated with quality materials and meticulous attention to detail, the home blends classic warmth with modern comfort. The open-concept main floor features a beautifully appointed kitchen ideal for family meals, flowing into the dining area and a cozy living room with a bay window and

    Steve Schoppmeyer BHG Masiello Brattleboro

    1909 Davidson Hill Rd, Westminster, VT 05158
  • /18

    $485,000 Sold Nov 05, 2025

    • 2,060 Sq Ft
    • $235/SF
    • 161 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    3 Mill Rd, West Dover, VT 05356

    When you picture a rustic and woodsy Vermont retreat, but with modern comforts, this is that home. Spacious chalet style home located conveniently on the MOOver shuttle route 3 miles from the Mount Snow Ski Resort. This 4 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large living room and updated gas fireplace on brick hearth, direct views of

    Adam Palmiter Berkley & Veller Greenwood/Dover

    3 Mill Rd, West Dover, VT 05356
    • /40

      Est $435,393 Not Listed For Sale

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

      50 Ray Hill Rd, Wilmington, VT 05363

      50 Ray Hill Rd, Wilmington, VT 05363
  • /41

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    25 Upper Handle Rd Unit A, Dover, VT 05356

    Welcome to this inviting 3-bedroom plus loft, 2-bath Apple Hill condominium—perfectly located just minutes from Mount Snow. This spacious and well-maintained home offers a comfortable layout for a relaxing Vermont getaway. The updated kitchen and dining area feature a charming window seat, while the open-concept living room boasts another cozy window seat and a wood-burning fireplace for those

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    25 Upper Handle Rd Unit A, Dover, VT 05356
  • /25

    $275,000 Sold Nov 04, 2025

    • 2,376 Sq Ft
    • $116/SF
    • 8 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1900

    50 Grove St, Brattleboro, VT 05301

    New to the market, this well-maintained 3-unit property is a fantastic opportunity for both investors and owner-occupants. Located just minutes from downtown, it offers convenience, value, and flexibility. One unit is currently on a month to month and move-in ready, making it ideal for someone looking to live on-site or set their own rental terms. The other two units are occupied by long-term,

    Kate Barry EXP Realty

    50 Grove St, Brattleboro, VT 05301
    • /21

      Est $445,288 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,914 Sq Ft

      157 Minor Rd, Wilmington, VT 05363

      157 Minor Rd, Wilmington, VT 05363
  • /42

    $798,000

    • 3 Beds
    • 2 Baths
    • 2,588 Sq Ft

    619 Stratton Arlington Rd, West Wardsboro, VT 05360

    Nestled between Stratton and Mount Snow and just minutes from Grout Pond, this timeless Vermont log home offers the perfect balance of rustic charm and modern comfort. Set on 7.90 beautifully landscaped acres with perennial gardens, a small pond, and mature fruit trees, the property captures the essence of mountain living.The main level features an open-concept layout with soaring beamed

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    619 Stratton Arlington Rd, West Wardsboro, VT 05360
  • /50

    $675,000 Sold Nov 03, 2025

    • 2,570 Sq Ft
    • $263/SF
    • 1 Day On Market
    • 4 Beds
    • 3 Baths
    • Built 1925

    7 Landgrove Rd, Landgrove, VT 05148

    Tucked away in a corner of beautiful Landgrove village just off a quiet country lane, this beautiful Post & Beam residence is a fascinating home designed for entertaining and fun! Enjoy the charm and architectural interest of the historic country barn it once was and all of the modern amenities resulting from two major renovations in 1985 and 2005 with continued updates and improvements over the

    Claudia Harris Mary Mitchell Miller Real Estate

    7 Landgrove Rd, Landgrove, VT 05148
    • /18

      Est $265,131 Not Listed For Sale

      • 5 Beds
      • 2.5 Baths
      • 2,030 Sq Ft

      36 Sparrow Ln, Wilmington, VT 05363

      36 Sparrow Ln, Wilmington, VT 05363
  • /3

    $500,000

    • Land
    • 5.05 Acres
    • $99,010 per Acre

    Lot 1 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 5+ acres overlooking the 18th hole and mountains beyond for year

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 1 Mountain Ridge Estates, Wilmington, VT 05363
  • /21

    $34,900 Sold Nov 03, 2025

    • 778 Sq Ft
    • $45/SF
    • 167 Days On Market
    • 1 Bed
    • 2 Baths
    • Built 1998

    201/03 Qt.3, 89 Grand Summit Way, Dover, VT 05356

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? One bedroom lockout sleep 8 unit. Studio side (201) has a Kitchen, living room with a queen murphy bed and queen sleeper sofa. Unit (203) has two queen beds. Both units have a full bathroom and balcony's. A great way to enjoy the mountain resort lifestyle at an affordable price.Benefits of Grand Summit ownership include the

    Kelly Agrillo Southern Vermont Realty Group

    201/03 Qt.3, 89 Grand Summit Way, Dover, VT 05356
    • /33

      Est $287,471 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,088 Sq Ft

      752 Route 9 E, Wilmington, VT 05363

      752 Route 9 E, Wilmington, VT 05363
  • /3

    $450,000

    • Land
    • 3.38 Acres
    • $133,136 per Acre

    Lot 4 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 3.38+ acres overlooking the 18th tee box and mountains beyond for

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 4 Mountain Ridge Estates, Wilmington, VT 05363
  • /40

    $390,000 Sold Nov 03, 2025

    • 1,980 Sq Ft
    • $197/SF
    • 4 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1985

    18 Hemlock Hill Rd, Newfane, VT 05345

    Tucked away on serene Hemlock Hill Road, a quiet private lane shared by just 4 homes, this lovingly maintained year-round A-frame offers the perfect blend of rustic charm and modern comfort. Built in 1985 and thoughtfully updated since, the home sits on 1.5 acres of manicured woodland, creating a peaceful retreat in the heart of Vermont’s natural beauty. Step inside to discover a bright and open

    Sandy Reavill Real Broker LLC

    18 Hemlock Hill Rd, Newfane, VT 05345
    • /36

      Est $439,493 Not Listed For Sale

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

      60 Hall Rd, Wilmington, VT 05363

      60 Hall Rd, Wilmington, VT 05363
  • /3

    $500,000

    • Land
    • 1.1 Acres
    • $454,545 per Acre

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.1 acres overlooking the fairway of the 18th hole and mountains

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 2 Mountain Ridge Estates, Wilmington, VT 05363
  • /2

    $480,000 Sold Nov 03, 2025

    • 2,800 Sq Ft
    • $171/SF
    • 30 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1986

    20 Challenger Hill, West Dover, VT 05356

    Charming Private Retreat Near Mount SnowNestled on a private, wooded lot, this inviting home offers serene outdoor living with both a front and rear deck, as well as a level front yard.Inside, the open-concept layout features a beautiful brick wood-burning fireplace in the living room and a cozy sunroom with vaulted ceilings and large windows that bathe the space in natural light. It

    Rich Caplan Deerfield Valley Real Estate

    20 Challenger Hill, West Dover, VT 05356
    • /20

      Est $465,576 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,536 Sq Ft

      143 Sun and Ski Rd, Wilmington, VT 05363

      143 Sun and Ski Rd, Wilmington, VT 05363
  • /3

    $500,000

    • Land
    • 1.82 Acres
    • $274,725 per Acre

    Lot 3 Mountain Ridge Estates, Wilmington, VT 05363

    Being offered for the first time, is this spectacular newly cleared home site with stunning views of the Haystack and Mount Snow ridgeline and sunsets beyond. Mountain Ridge Estates abuts the Haystack Golf Club and are exclusive home sites for the discerning buyer looking to create a special spot in Vermont. This particular lot is 1.82+ acres overlooking the 18th fairway and mountains beyond for

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot 3 Mountain Ridge Estates, Wilmington, VT 05363
  • /14

    $250,000 Sold Oct 31, 2025

    • 1,250 Sq Ft
    • $200/SF
    • 5 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1995

    70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301

    Beautifully elegant light filled condo in Bluebell Building at Arbor Hill. An abundance of windows throughout creates a magical light filled environment that includes hardwood flooring, a Great Room providing space for Living, Dining and Kitchen, 2 spacious Bedrooms, 2 Full Baths, Entry w/ double closet and Laundry/Pantry. The Primary Bedroom has an en suite Bath, mini split and a large walk-in

    Robert Doyle Berkley & Veller Greenwood Country

    70 Arbor Hill Commons Unit 15, Brattleboro, VT 05301
    • /36

      Est $933,247 Not Listed For Sale

      • 7 Beds
      • 5 Baths
      • 3,574 Sq Ft

      72 Aldrich Rd, Wilmington, VT 05363

      72 Aldrich Rd, Wilmington, VT 05363
  • /54

    $3,750,000

    • 6 Beds
    • 6.5 Baths
    • 5,660 Sq Ft

    168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360

    Experience true mountain luxury in this stunning six bedroom six bathroom slope side single family home, perfectly positioned for effortless access to world-class skiing and snowboarding at the Stratton Mountain Resort. Designed with comfort and style in mind, this residence combines refined alpine architecture with modern amenities including a gym, steam shower, pool table that doubles as table

    Timothy Mich Doddridge Stratton Real Estate

    168 Sunbowl Ridge Rd Unit 168 AB, Stratton, VT 05360
  • /39

    $512,000 Sold Oct 31, 2025

    • 1,866 Sq Ft
    • $274/SF
    • 414 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1989

    58 Colonial Ridge Rd, Dover, VT 05356

    This Wonderful Home is being offered for the first time in over 20 years. The current owners have enjoyed it, and taken care of it with upgrades and upkeep as needed. The newer paint, standing seam metal roof, deck stain, kitchen remodel including appliances, glass slider, all interior solid core doors and Rinnai heating units are all evidence to the care this home has seen. The high ceilings and

    Steve Goldfarb Deerfield Valley Real Estate

    58 Colonial Ridge Rd, Dover, VT 05356
    • /29

      Est $427,058 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 1,100 Sq Ft

      259 Vt Route 100 N, Wilmington, VT 05363

      259 Vt Route 100 N, Wilmington, VT 05363
  • /9

    $185,000

    • Land
    • 8 Acres
    • $23,125 per Acre

    4441 Vermont 30, Jamaica, VT 05343

    Set amidst a peaceful woodland setting, this 8.0± acre parcel offers the perfect balance of seclusion and convenience—tucked away for privacy yet easily accessible year-round.. Currently being subdivided from a larger tract, this parcel presents a rare chance to shape your vision from the ground up.A five-bedroom Wastewater Permit has been approved, and a professional boundary survey is

    Helen Nault

    4441 Vermont 30, Jamaica, VT 05343
  • /51

    $280,000 Sold Oct 31, 2025

    • 3,468 Sq Ft
    • $81/SF
    • 88 Days On Market
    • 6 Beds
    • 3 Baths
    • Built 1850

    31 School St, Bellows Falls, VT 05101

    Attractive and well maintained 3 unit Multi-family with great in-town location. Many original features remain including wood floors, 2 marble mantles, moldings, curved walls, beautiful arches and built-ins. Unit 1 on the first floor features living room open via graceful arches to dining room, large eat-in kitchen, 2 large bedrooms,, hardwood floors, marble fireplaces. Unit 2 is on the 2nd floor

    Steve Schoppmeyer BHG Masiello Brattleboro

    31 School St, Bellows Falls, VT 05101
    • /18

      Est $326,231 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,564 Sq Ft

      57 Riverside Dr, Wilmington, VT 05363

      57 Riverside Dr, Wilmington, VT 05363
  • /52

    $1,150,000

    • 8 Beds
    • 4 Baths
    • 4,828 Sq Ft

    5 Tannery Rd, West Dover, VT 05356

    Discover your getaway at Mount Snow in this beautifully renovated 8-bedroom estate, ideal for unforgettable family gatherings, cherished reunions, or inspiring work retreats. Set on nearly 4 serene acres at the foot of Mount Snow, you'll be surrounded by breathtaking mountain views and enjoy effortless access to the slopes just a short drive away. This magnificent home features a dedicated

    Michelle O'Neil Deerfield Valley Real Estate

    5 Tannery Rd, West Dover, VT 05356
  • /57

    $595,000 Sold Oct 31, 2025

    • 2,740 Sq Ft
    • $217/SF
    • 8 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1988

    138 Gardiner Dr, Londonderry, VT 05148

    Nestled within the exclusive 400-acre Powder Mill Reserve and directly abutting Lowell Lake State Park, this exceptional 4-bedroom, 3-bath home offers a rare opportunity to own a slice of paradise. Designed for those who cherish the outdoors, the property provides direct access to hiking trails, scenic ponds, VAST snowmobile trails, and panoramic views – all with the peace and privacy of a

    Kevin Barnes William Raveis Real Estate Vermont Properties

    138 Gardiner Dr, Londonderry, VT 05148
    • /40

      Est $695,336 Not Listed For Sale

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

      143 Ray Hill Rd, Wilmington, VT 05363

      143 Ray Hill Rd, Wilmington, VT 05363
  • /26

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    106 Silver Birch Unit 17H, Dover, VT 05356

    Bright 3-Bedroom End Unit at Timber Creek – Across from Mount Snow Ski Area.Welcome to your mountain getaway! This sunny 3-bedroom, 2-bath end unit in the desirable Timber Creek condominium community offers the perfect blend of comfort, convenience, and year-round recreation. Located directly across from Mount Snow and a short drive to the Hermitage Club, you'll enjoy unbeatable access to

    Heidi Zizza Four Seasons Sotheby's Int'l Realty

    106 Silver Birch Unit 17H, Dover, VT 05356
  • /16

    $310,000 Sold Oct 31, 2025

    • 1,248 Sq Ft
    • $248/SF
    • 236 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1980

    12E Dover Green Loop Unit 12E, Dover, VT 05356

    Renovated townhome in the Dover Green community located just a short drive or shuttle ride south of Mount Snow. This spacious unit overlooks a pond and nice sunny exposure thanks to recent clearing, and has easy access to parking and the side yard. Inside is an open concept floor plan with vaulted great room, wood burning fireplace and brick hearth, a large eat in kitchen with new cabinets,

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12E Dover Green Loop Unit 12E, Dover, VT 05356
    • /24

      Est $579,519 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,836 Sq Ft

      252 Ray Hill Rd, Wilmington, VT 05363

      252 Ray Hill Rd, Wilmington, VT 05363

Showing Results 241 - 280, Page 7 of 18

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