30,390

Windham County, VT Homes

Section Image
  • /51

    $725,000

    • 4 Beds
    • 2 Baths
    • 1,370 Sq Ft

    98 Darby Hill Rd, Bellows Falls, VT 05101

    TOTAL PRIVACY ON 96 ACRES ABUTS THE VILLAGE FOREST & THE LOCATION OF MINARD'S POND. THIS WELL CARED FOR HOME IS CLASSIC COUNTRY THROUGHOUT W/HARD WOOD, WIDE BOARD FLOORS & BEAUTIFULL WOOD CEILINGS, FULLY APPLIANCED KITCHEN & LAUNDRY ROOM, UPDATED BATHS PLUS A REAR DECK W/TREX FLOORING OFF THE FOUR SEASON SUN ROOM. A LARGE 3 BAY BARN, WORKSHOP W/ 2ND FLOOR & ATTACHED CAR PORT W/CEMENT FLOOR.

    Don Chabot Town and Country Realty

    98 Darby Hill Rd, Bellows Falls, VT 05101
  • /38

    $109,000 Sold Jul 30, 2025

    • 1,400 Sq Ft
    • $78/SF
    • 6 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1938

    16 Jones Hill Rd, Newfane, VT 05362

    Property being sold 'as is', conveyed with clean title.Seller has not occupied property, so no disclosures are available.Dwelling does have 'good bones', garage is worthless.“This property is eligible under the Freddie Mac First Look Initiative through 07/26/2025.

    Robert Balewicz Evergreen Realty of Vermont

    16 Jones Hill Rd, Newfane, VT 05362
    • /15

      Est $346,348 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,620 Sq Ft

      164 Gilfeather Rd, Wardsboro, VT 05355

      164 Gilfeather Rd, Wardsboro, VT 05355
  • /36

    $26,500

    • 1 Bed
    • 1 Bath
    • 671 Sq Ft

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

    Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Benefits of Grand Summit ownership include the best ski in/out mountain location available. Use of the Grand Summit amenities all year round including valet parking, owners private lounge, private owners library, full service spa with saunas hot tubs and outdoor heated pool, private owners only ski/golf locker rooms for year

    Kelly Agrillo Southern Vermont Realty Group

    308 Qtr.4, 89 Grand Summit Way, Dover, VT 05356
  • /18

    $335,000 Sold Jul 30, 2025

    • 1,174 Sq Ft
    • $285/SF
    • 36 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1956

    138 Cedar St, Brattleboro, VT 05301

    Welcome to this adorable 3-bedroom, 1-bath ranch-style home nestled in one of Brattleboro's most sought-after neighborhoods! Built in 1956, this lovingly cared for gem perfectly blends classic character with modern comfort. Many recent upgrades including CertainTeed Monogram vinyl siding and trim, freshly painted interior walls and so much more. The kitchen features a sleek Whirlpool glass top

    Claire Renaud Berkley & Veller Greenwood Country

    138 Cedar St, Brattleboro, VT 05301
    • /13

      Est $131,329 Not Listed For Sale

      • 3 Beds

      70 Broad Brook Rd, Vernon, VT 05354

      70 Broad Brook Rd, Vernon, VT 05354
  • /13

    $185,000

    • Land
    • 15 Acres
    • $12,333 per Acre

    491 Whitneyville Rd, Halifax, VT 05358

    Escape the hustle and bustle of suburban life with this serene 15- acre parcel, comprising open meadow and woodland. Surrounded by mature trees, this tranquil lot is ideal for the nature lovers, providing seasonal ridgeline mountain views that enhance its beauty. A drilled well is already in place, ready to connect to for your future home. Conveniently located in southern Vermont, you'll enjoy

    Monica Sumner BHG Masiello Brattleboro

    491 Whitneyville Rd, Halifax, VT 05358
  • /44

    $510,000 Sold Jul 30, 2025

    • 2,352 Sq Ft
    • $217/SF
    • 68 Days On Market
    • 6 Beds
    • 3.5 Baths
    • Built 1965

    592 Vermont Route 100, Stratton, VT 05360

    6 Bed/4 Bath Expansive Chalet! Located in Stratton, minutes north of Mount Snow. Loft, den, two kitchens offer incredible space, flexibility, and potential across three full levels. Floor plan accommodates large groups, setting that offers easy access to skiing, snowmobiling, all-season recreation, and the Stratton Town Forest. Main floor welcomes you with soaring brick fireplace anchoring the

    Jacki Murano Southern Vermont Realty Group

    592 Vermont Route 100, Stratton, VT 05360
    • /35

      Est $273,196 Not Listed For Sale

      • 4 Beds
      • 1 Bath
      • 1,152 Sq Ft

      63 Washburn Way, Vernon, VT 05354

      63 Washburn Way, Vernon, VT 05354
  • /59

    $795,000

    • 3 Beds
    • 3.5 Baths
    • 1,730 Sq Ft

    2A Townhouse Square Unit T-4, Dover, VT 05356

    Experience the best of all worlds! Just 100 feet from your front door, you can hop onto a Mount Snow ski trail, or take a short walk to the newly renovated and expanded, on-site Amenities Center, featuring an indoor pool, outdoor pool, exercise room, saunas, lockers, and more. This beautifully appointed, fully furnished townhome is truly turnkey. Inside, you’ll find three fireplaces—including one

    John Redd Skihome Realty

    2A Townhouse Square Unit T-4, Dover, VT 05356
  • /39

    $380,000 Sold Jul 29, 2025

    • 1,150 Sq Ft
    • $330/SF
    • 27 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1986

    75 E Birch Rd Unit 39, Stratton, VT 05360

    Welcome to Vantage Point ! This updated and well appointed end unit is conveniently located on the second level of the middle building right behind the Stratton Fitness Center overlooking the outdoor tennis and pickleball courts. More recent upgrades are new flooring throughout, newer washer/dryer and lighting. Guest bedroom is set up for families. Winter shuttle service to the mtn base

    Terry Hill Berkshire Hathaway HomeServices Stratton Home

    75 E Birch Rd Unit 39, Stratton, VT 05360
    • /40

      Est $218,925 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,120 Sq Ft

      550 Newton Rd, Vernon, VT 05354

      550 Newton Rd, Vernon, VT 05354
  • /20

    $279,900

    • 4 Beds
    • 2 Baths
    • 1,733 Sq Ft

    1177 Western Ave, Brattleboro, VT 05301

    So much to offer! This 4 bedroom 2 bath has plenty of room for all! It features a large kitchen with lots of counter space and the laundry tucked in for easy access while you cook and bake. The deck overlooks the lower yard where the solar panels live and the perfect spot for the above ground swimming pool (needs a liner). Huge lot, lots of off street parking and on the MOOVER line for non

    Christine Lewis Brattleboro Area Realty

    1177 Western Ave, Brattleboro, VT 05301
  • /44

    $405,000 Sold Jul 28, 2025

    • 2,132 Sq Ft
    • $190/SF
    • 33 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1998

    156 Sherwood Cir, Brattleboro, VT 05301

    YOU CAN GET THERE FROM HERE! NEW ENGLAND CHARM AND FLEXIBLE SPACES...YOUR LUSH RETREAT AWAITS! A short drive to the cultural and foodie hub of southeastern Vermont, this slice of heaven is where your dreams take root. Follow a scenic road to a vibrant green lot where a terraced rock wall dotted with ferns and hostas signals your arrival. A large covered porch invites you to pull up a chair,

    Fine Homes Group International Keller Williams Realty-Metropolitan

    156 Sherwood Cir, Brattleboro, VT 05301
    • /39

      Est $490,839 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,195 Sq Ft

      131 Woodland Rd, Vernon, VT 05354

      131 Woodland Rd, Vernon, VT 05354
  • /16

    $22,450

    • 1 Bath
    • 407 Sq Ft

    239 - Qtr 4 89 Grand Summit Way Unit 239, Dover, VT 05356

    Quarter share (deeded interval 4) ownership at the Grand Summit offers 13 weeks of vacation per year on a rotating schedule that can be used, rented, or traded as you desire. Ownership this year includes Thanksgiving, Christmas/New years and Feb vacation weeks. This second floor (Unit 239) with mountain views sleep four studio is 407 sq ft and has a murphy bed in the living area, a kitchen/dining

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    239 - Qtr 4 89 Grand Summit Way Unit 239, Dover, VT 05356
  • /23

    $356,000 Sold Jul 28, 2025

    • 1,550 Sq Ft
    • $230/SF
    • 38 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1929

    122 Marlboro Ave, Brattleboro, VT 05301

    122 Marlboro Avenue is in a highly sought out, in-town neighborhood known for its peace and quiet, friendly neighbors, and super-convenient location. This solid, 3-4 bedroom, 2 bath home sits attractively on a sunny and level lot and comes with an oversized garage and attached workshop (and potential to add additional living space). This home provides a completely renovated and modernized

    Stephanie Peduzzi-Baker Brattleboro Area Realty

    122 Marlboro Ave, Brattleboro, VT 05301
    • /40

      Est $467,311 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 3,551 Sq Ft

      19 Southern Heights Dr, Vernon, VT 05354

      19 Southern Heights Dr, Vernon, VT 05354
  • /9

    $389,000

    • Land
    • 10 Acres
    • $38,900 per Acre

    LOT E Handle Rd, West Dover, VT 05356

    Location, Location, Location! This exceptional wooded, level lot offers the perfect blend of privacy and convenience in one of Vermont’s most desirable areas. The Coldbrook River runs gracefully through the property, creating a peaceful natural setting. Views of Haystack Mountain with clearing. An ideal spot for your dream home. Situated just minutes from The Hermitage Inn and the exclusive,

    Richard Caplan Deerfield Valley Real Estate

    LOT E Handle Rd, West Dover, VT 05356
  • /26

    $347,000 Sold Jul 25, 2025

    • 1,435 Sq Ft
    • $242/SF
    • 22 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1890

    157 Pine St, Brattleboro, VT 05301

    Be impressed by this stately in-town Victorian home with an airy and open-concept feel, handsome historical features, and many thoughtful and attractive upgrades. Enter this lovely home loaded with charm and character and be prepared to be wowed with high ceilings and the gorgeous hardwood floors! A highlight of the house is an attractive kitchen with appealing custom cabinetry, granite and

    Stephanie Peduzzi-Baker Brattleboro Area Realty

    157 Pine St, Brattleboro, VT 05301
    • /40

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,139 Sq Ft

      86 Silver Ln, Vernon, VT 05354

      86 Silver Ln, Vernon, VT 05354
  • /19

    $400,000

    • 4 Beds
    • 2 Baths
    • 2,056 Sq Ft

    48 Landing Ln, Wilmington, VT 05363

    Private boat slip and beach access from this charming contemporary home just off Lake Raponda and a short drive to the Mount Snow ski resort. Enjoy the best of both worlds with easy access to summer boating, swimming, tennis, and outdoor activities for the summer, just a short drive from skiing and with direct snowmobile trail access. This 2003 home sits privately on a 4.35 acre lot with

    Adam Palmiter Berkley & Veller Greenwood/Dover

    48 Landing Ln, Wilmington, VT 05363
  • /2

    $250,000 Sold Jul 25, 2025

    • 900 Sq Ft
    • $278/SF
    • 9 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1971

    373 Brookline Rd, Athens, VT 05143

    Tucked away on 16 wooded acres in the quiet hills of Athens, Vermont, this unique property offers the kind of peace that’s getting harder to find. At its center is a simple, charming cabin with an open floor plan and vaulted ceiling, set just above a beaver pond that draws in wildlife and reflects the changing sky. It’s quiet here—really quiet. The kind of place where time slows down and the

    Daire Gibney Barrett and Valley Associates Inc.

    373 Brookline Rd, Athens, VT 05143
    • /30

      Est $442,185 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,482 Sq Ft

      8 Shirley Dr, Vernon, VT 05354

      8 Shirley Dr, Vernon, VT 05354
  • /13

    $79,500

    • Land
    • 3.5 Acres
    • $22,714 per Acre

    0 Dover Rd Unit 5054979, Newfane, VT 05345

    Welcome to your future home in the heart of a picturesque Vermont village! These exquisite land lots, thoughtfully designed by the architect-owner, offer a unique opportunity to build your dream home in a setting that perfectly captures the quintessential charm of small-town Vermont. Each lot is meticulously planned to adhere to the timeless "Vermont Vernacular" style, ensuring that your new

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    0 Dover Rd Unit 5054979, Newfane, VT 05345
  • /50

    $469,000 Sold Jul 25, 2025

    • 1,346 Sq Ft
    • $348/SF
    • 47 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2003

    2194 Mowrey Rd, Jamaica, VT 05343

    Diamond in the rough! Don't miss this opportunity to own a property in Jamaica, Vermont that has so much to offer! This property has been absolutely stunning in the past! Perched on a hill overlooking a private pond, fields that used to be pastures where your animals can roam and you can take in the local ridgeline view of the beautiful Green Mountains of Vermont! This is a true log home with

    Julie Lowe Lowe's Real Estate, LLC

    2194 Mowrey Rd, Jamaica, VT 05343
    • /35

      Est $306,210 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,092 Sq Ft

      7 Allison Ln, Vernon, VT 05354

      7 Allison Ln, Vernon, VT 05354
  • /26

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    78 Taft Brook Rd, East Dover, VT 05341

    Lovely country home that is being offered for the first time in 52 years. This special spot is 2 acres just off the Taft Brook in East Dover, a short drive from the Mount Snow ski resort, village of Wilmington, and Brattleboro. Enjoy complete privacy off the quiet country road, with beautiful landscaping, perennial gardens, natural stone work, level yard space, and direct access to walking and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    78 Taft Brook Rd, East Dover, VT 05341
  • /29

    $365,000 Sold Jul 25, 2025

    • 1,620 Sq Ft
    • $225/SF
    • 10 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2006

    28 Greenleaf St, Brattleboro, VT 05301

    West Brattleboro contemporary cape situated on a large private partially fenced lot with fruit trees, raised bed gardens and plenty of outdoor recreational space. This sturdy, well-built house offers low maintenance and quality finishes like the standing seam metal roof and cement siding. Ample large windows bring the outside IN and provide lots of natural light. Interior features include: a

    Chris Long BHG Masiello Brattleboro

    28 Greenleaf St, Brattleboro, VT 05301
    • /40

      Est $685,477 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,273 Sq Ft

      116 Lily Pond Rd, Vernon, VT 05354

      116 Lily Pond Rd, Vernon, VT 05354
  • /40

    $720,000

    • 3 Beds
    • 3.5 Baths
    • 2,250 Sq Ft

    134 Ellis Brook Rd, Dover, VT 05356

    This stunningly renovated 3-bedroom, 3.5-bathroom vacation home with carport, completed in 2021, offers exceptional comfort and style in Dover Hills, near Mount Snow. The remodel includes a brand-new kitchen, bathrooms, flooring, and furniture throughout. Notable upgrades feature an additional 3/4 bathroom, a fully finished basement, and upgraded plumbing, electrical systems, and roof. Modern

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    134 Ellis Brook Rd, Dover, VT 05356
  • /27

    $487,500 Sold Jul 25, 2025

    • 2,832 Sq Ft
    • $172/SF
    • 12 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1985

    32 Christie Ln, Brattleboro, VT 05301

    This will be your favorite new listing. Tucked on a pocket of land, just beyond Memorial Park, you're in a neighborhood but it feels private, you see trees out every window. Custom-built home, 3 bedrooms, 2 1/2 updated baths, built in 1985. Incredibly warm and comfy. Cathedral ceiling with a wall of windows. Great kitchen for cooking, plenty of room for multiple chefs. Cozy nook for a small

    John Hatton Berkley & Veller Greenwood Country

    32 Christie Ln, Brattleboro, VT 05301
    • /35

      Est $305,411 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,909 Sq Ft

      672 Hucklehill Rd, Vernon, VT 05354

      672 Hucklehill Rd, Vernon, VT 05354
  • /31

    $556,000

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft

    174 Whites Hill Rd, Dover, VT 05356

    Nestled amidst over 20 acres of pristine land, this Moosehead log home offers the perfect blend of privacy and breathtaking views. Imagine living without the burden of an electric bill, as this property is equipped with a complete solar power system and a backup generator, ensuring you have all the modern conveniences while embracing a sustainable lifestyle.Whether you're working remotely

    Regina Perrotto Skihome Realty

    174 Whites Hill Rd, Dover, VT 05356
  • /17

    $195,000 Sold Jul 25, 2025

    • 1,414 Sq Ft
    • $138/SF
    • 26 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1880

    2147 N Main St, Londonderry, VT 05148

    Terrific in-town location! Improvements include new roof and trim last year, 24kw Generator, serviced annually, new flooring on first level and new washer and dryer. Easy to maintain yard space, walk to the plaza for shopping and restaurants, minutes to 3 ski resorts!

    Lisa Kelley Cummings & Co

    2147 N Main St, Londonderry, VT 05148
    • /33

      Est $293,074 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 936 Sq Ft

      156 Scott Rd, Vernon, VT 05354

      156 Scott Rd, Vernon, VT 05354
  • /57

    $2,595,000

    • 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
  • /23

    $170,000 Sold Jul 25, 2025

    • 2,764 Sq Ft
    • $62/SF
    • 32 Days On Market
    • 6 Beds
    • 4 Baths
    • Built 1974

    233 Bluebrook Rd, Dover, VT 05356

    The property is situated in a desirable location, making it an attractive option for potential buyers or investors. However, it requires significant renovations to enhance its overall appeal and functionality. Currently configured as a three-family residence, the house presents opportunities for conversion or improvement to maximize rental income or create a single-family home, depending on the

    Regina Perrotto Skihome Realty

    233 Bluebrook Rd, Dover, VT 05356
    • /34

      Est $453,305 Not Listed For Sale

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

      458 Hazel Hill Rd, Townshend, VT 05353

      458 Hazel Hill Rd, Townshend, VT 05353
  • /2

    $300,000

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft

    109 Central St, Brattleboro, VT 05301

    Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard

    Christine Lewis Brattleboro Area Realty

    109 Central St, Brattleboro, VT 05301

Showing Results 401 - 440, Page 11 of 18

How to Buy a Home How to Finance a Home How to Sell a Home