30,689

Windham County, VT Homes

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  • /26

    $325,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 976 Sq Ft

    9047 Vermont 30, Jamaica, VT 05155

    “The Yellow Sweetie” offers a rare blend of charm, convenience, and proven income potential. This stylish country-meets-shabby-chic retreat has been a high-income producing rental for many years, making it an excellent opportunity for investment, year-round living, or a Vermont vacation retreat.Ideally located near the base of Stratton Mountain, the property sits just one minute from the

    Carrie Mathews Winhall Real Estate

    9047 Vermont 30, Jamaica, VT 05155
  • /46

    $299,000 Sold Jan 22, 2026

    4410 Pikes Falls Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 2,194 Sq Ft
    • Built 1962

    Last Sold Summary

    • 5% Below List Price
    • $136/SF
    • 5 Days On Market

    Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

    4410 Pikes Falls Rd, Jamaica, VT 05343
    • /11

      Not Listed For Sale

      3960 Jacksonville Stage Rd, West Halifax, VT 05358

      3960 Jacksonville Stage Rd, West Halifax, VT 05358

      Last Sold Summary

      • 6 Days On Market

      Last Sold Price $96,000

      Last Listing Agent Betsy Adamovich Real Broker LLC

  • /21

    $489,000

    • 3 Beds
    • 2 Baths
    • 2,003 Sq Ft

    12 Lilla Ln, Wilmington, VT 05363

    Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private

    Adam Palmiter Berkley & Veller Greenwood/Dover

    12 Lilla Ln, Wilmington, VT 05363
  • /8

    $59,000 Sold Mar 14, 2025

    1625 Vt Route 9, Searsburg, VT 05363

    • Land
    • 13.5 Acres
    • $4,370 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 172 Days On Market

    Last Listing Agent Mike Masters Four Seasons Sotheby's Int'l Realty

    1625 Vt Route 9, Searsburg, VT 05363
    • /9

      Not Listed For Sale

      0 Parker Hill Rd, Bellows Falls, VT 05101

      0 Parker Hill Rd, Bellows Falls, VT 05101

      Last Sold Summary

      • 284 Days On Market

      Last Sold Price $155,000

      Last Listing Agent Will Cronin Barrett & Valley Assoc. Inc

  • /31

    $1,750,000

    • 4 Beds
    • 3.5 Baths
    • 2,698 Sq Ft

    148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360

    148B Sun Bowl Ridge Rd., Stratton Mountain, VT 05155, Solstice 148B Ski in, ski out directly from your private garage on a Stratton ski trail that has full snowmaking coverage. This home is in one of the most exclusive trailside communities in all of the Northeast! It has an open and sunny floorplan with large windows and a sliding glass door to the private patio with fire pit and hot tub.

    Andrew King Stratton Real Estate

    148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
  • /51

    $343,000 Sold Jun 23, 2025

    442 S Wardsboro Rd, Newfane, VT 05345

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft
    • Built 1795

    Last Sold Summary

    • 4% Above List Price
    • $223/SF
    • 7 Days On Market

    Current Estimated Value $332,436

    Last Listing Agent Laura D'Angelo Berkley & Veller Greenwood Country

    442 S Wardsboro Rd, Newfane, VT 05345
    • /5

      Est $118,667 Not Listed For Sale

      29 Woodsman Rd, West Dover, VT 05356

      29 Woodsman Rd, West Dover, VT 05356

      Last Sold Summary

      • 133% Above List Price
      • 25 Days On Market

      Last Sold Price $51,000

      Last Listing Agent Leslie Fraser Four Seasons Sotheby's Int'l Realty

  • /32

    $229,000

    • 3,302 Sq Ft

    36 Barker St, Town of Rockingham, VT 05101

    This charming three-unit property in the heart of Bellows Falls, VT, offers a rare combination of historic character and modern appeal. With its exterior freshly painted in November 2025, the building exudes curb-appeal and care. Inside, the first-floor unit features three bedrooms and a full bath—perfect for a family or long-term tenant—while the second and third-floor units each offer two

    Rob Weltz Barrett and Valley Associates Inc.

    36 Barker St, Town of Rockingham, VT 05101
  • /37

    $375,000 Sold Jun 16, 2025

    146 Sherwood Cir, Brattleboro, VT 05301

    • 3 Beds
    • 1.5 Baths
    • 1,632 Sq Ft
    • Built 1998

    Last Sold Summary

    • 7% Above List Price
    • $230/SF
    • 66 Days On Market

    Current Estimated Value $439,829

    Last Listing Agent Kate Barry EXP Realty

    146 Sherwood Cir, Brattleboro, VT 05301
    • /12

      Est $614,171 Not Listed For Sale

      58 Oak St, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 3,400 Sq Ft
      • Built 1867
      58 Oak St, Brattleboro, VT 05301

      Last Sold Summary

      • 3% Above List Price
      • $175/SF
      • 20 Days On Market

      Last Sold Price $595,000

      Last Listing Agent Robert Doyle Berkley & Veller Greenwood Country

  • /15

    $67,500

    • Land
    • 3.5 Acres
    • $19,286 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 home

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    0 Dover Rd Unit 5054979, Newfane, VT 05345
  • /30

    $105,000 Sold Dec 03, 2025

    10 Taylor St, Town of Rockingham, VT 05101

    • 1,968 Sq Ft
    • Built 1910

    Last Sold Summary

    • 16% Below List Price
    • $53/SF
    • 97 Days On Market

    Current Estimated Value $107,581

    Last Listing Agent Julie Buffum Buffum Realty

    10 Taylor St, Town of Rockingham, VT 05101
    • /22

      Not Listed For Sale

      0 Bills Rd, Stratton, VT 05360

      0 Bills Rd, Stratton, VT 05360

      Last Sold Summary

      • 119 Days On Market

      Last Sold Price $150,000

      Last Listing Agent Monique White Deerfield Valley Real Estate

  • /24

    $92,999 Under Contract

    • 2 Beds
    • 2 Baths
    • 790 Sq Ft

    201 Shady Pines, Westminster, VT 05158

    Welcome to 201 Shady Pines, Westminster VT 05158, where modern comfort meets affordability in Shady Pines MHP! This brand-new Cortes model manufactured home offers 2 bedrooms, 2 bathrooms, and 790 sq. ft. (14 x 60 ft.) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

    Kate Barry EXP Realty

    201 Shady Pines, Westminster, VT 05158
  • /2

    $80,000 Sold Dec 19, 2025

    Lot #3 Peachtree Ln, Brattleboro, VT 05301

    • Land
    • 4.27 Acres
    • $18,735 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 50 Days On Market

    Last Listing Agent Desiree Stango Berkley & Veller Greenwood Country

    Lot #3 Peachtree Ln, Brattleboro, VT 05301
    • /32

      Not Listed For Sale

      432 Route 121, Westminster, VT 05158

      • 6 Beds
      • 2 Baths
      • 2,899 Sq Ft
      • Built 1903
      432 Route 121, Westminster, VT 05158

      Last Sold Summary

      • $62/SF
      • 148 Days On Market

      Last Sold Price $180,000

      Last Listing Agent Steve Schoppmeyer BHG Masiello Brattleboro

  • /46

    $495,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,756 Sq Ft

    214 Putney Rd, Brattleboro, VT 05301

    Step back in time and discover the enchanting potential of this distinguished 1940 Colonial, perfectly positioned to capture the spirit of Brattleboro. Perched on a generous 0.79-acre level lot, this home offers a rare blend of expansive personal space and convenient in-town living. From the moment you arrive, the classic lines, wood siding, and enduring slate roof hint at the craftsmanship of a

    Keith Nowak Four Seasons Sotheby's Int'l Realty

    214 Putney Rd, Brattleboro, VT 05301
  • /14

    $240,000 Sold Jul 17, 2025

    17 Wardon Rd, Putney, VT 05346

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1974

    Last Sold Summary

    • 4% Below List Price
    • $210/SF
    • 34 Days On Market

    Current Estimated Value $286,914

    Last Listing Agent Jody Graves Berkley & Veller Greenwood Country

    17 Wardon Rd, Putney, VT 05346
    • /3

      Est $415,593 Not Listed For Sale

      394 Canal St, Brattleboro, VT 05301

      • Studio
      • 2 Baths
      • 2,863 Sq Ft
      • Built 1930
      394 Canal St, Brattleboro, VT 05301

      Last Sold Summary

      • 12% Above List Price
      • $129/SF
      • 0 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Christine Lewis Brattleboro Area Realty

  • /30

    $749,000

    • Land
    • 2.57 Acres
    • $291,440 per Acre

    Lot 3 Old Mill Ln, Wilmington, VT 05363

    Bring your own builder and discover an exceptional opportunity to own a 2.57 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 3 Old Mill Ln, Wilmington, VT 05363
  • /29

    $495,000 Sold Nov 21, 2025

    275 Pams Hill Rd, Wardsboro, VT 05355

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 1969

    Last Sold Summary

    • 4% Below List Price
    • $330/SF
    • 59 Days On Market

    Current Estimated Value $493,584

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    275 Pams Hill Rd, Wardsboro, VT 05355
    • /40

      Est $551,934 Not Listed For Sale

      1084 Cyrus Rd, Whitingham, VT 05361

      • 3 Beds
      • 4 Baths
      • 2,200 Sq Ft
      • Built 2005
      1084 Cyrus Rd, Whitingham, VT 05361

      Last Sold Summary

      • 2% Above List Price
      • $245/SF
      • 129 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Kristen Breeden Southern Vermont Realty Group

  • /22

    $539,000

    • Land
    • 2.88 Acres
    • $187,153 per Acre

    309 Vermont Route 100, Dover, VT 05356

    Prime Investment Opportunity – Near Mount Snow Ski Resort!An exceptional development opportunity awaits just half a mile from Mount Snow Ski Resort. This level lot with stunning mountain views is ideally situated close to all area recreation – skiing, snowboarding, hiking, biking, and more.Plans for 8 units / 24 bedroomsTown sewer availableMost permits secured – only waiting on

    Rich Caplan Deerfield Valley Real Estate

    309 Vermont Route 100, Dover, VT 05356
  • /49

    $625,000 Sold Jan 15, 2026

    956 Old Cheney Rd, West Townshend, VT 05359

    • 2 Beds
    • 2 Baths
    • 2,144 Sq Ft
    • Built 1790

    Last Sold Summary

    • 14% Below List Price
    • $292/SF
    • 141 Days On Market

    Current Estimated Value $651,360

    Last Listing Agent Kim Meeker Southern Vermont Realty Group

    956 Old Cheney Rd, West Townshend, VT 05359
    • /37

      Est $442,163 Not Listed For Sale

      94 Brets Rd, Brattleboro, VT 05301

      • 3 Beds
      • 2.5 Baths
      • 1,444 Sq Ft
      • Built 2001
      94 Brets Rd, Brattleboro, VT 05301

      Last Sold Summary

      • 2% Above List Price
      • $301/SF
      • 16 Days On Market

      Last Sold Price $434,000

      Last Listing Agent John Redd Skihome Realty

  • /35

    $125,000 Under Contract

    • Land
    • 1.52 Acres
    • $82,237 per Acre

    406 Fox Mountain Rd, Wilmington, VT 05363

    Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all

    Sigrid Pickering Chimney Hill Realty

    406 Fox Mountain Rd, Wilmington, VT 05363
  • /44

    $655,000 Sold Sep 12, 2025

    1176 E Dover Rd, Wardsboro, VT 05355

    • 2 Beds
    • 1.5 Baths
    • 1,530 Sq Ft
    • Built 2000

    Last Sold Summary

    • 2% Above List Price
    • $428/SF
    • 7 Days On Market

    Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

    1176 E Dover Rd, Wardsboro, VT 05355
    • /32

      Est $533,970 Not Listed For Sale

      110 Beaver Pond Rd, Dummerston, VT 05301

      • 3 Beds
      • 2.5 Baths
      • 2,280 Sq Ft
      • Built 2008
      110 Beaver Pond Rd, Dummerston, VT 05301

      Last Sold Summary

      • 2% Above List Price
      • $230/SF
      • 9 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

  • /50

    $319,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,468 Sq Ft

    756 Turkey Mountain Rd, Jamaica, VT 05343

    Tucked away on 2.5± mostly level acres with stonewalls and a brook at the edge of the property, this Jamaica, Vermont, Cape offers a rare combination of usable land, privacy, and natural beauty. Inside, the 3-bedroom, 2-bath home offers a sensible, functional floor plan with solid bones and the opportunity to update and personalize over time. First-floor bedroom with a newly refreshed full bath,

    Jacki Murano Southern Vermont Realty Group

    756 Turkey Mountain Rd, Jamaica, VT 05343
  • /53

    $685,000 Sold Aug 13, 2025

    37 Spring Hill Rd, West Dover, VT 05356

    • 4 Beds
    • 5.5 Baths
    • 3,695 Sq Ft
    • Built 2005

    Last Sold Summary

    • 19% Below List Price
    • $185/SF
    • 109 Days On Market

    Current Estimated Value $710,929

    Last Listing Agent Jillian Wimmelman Deerfield Valley Real Estate

    37 Spring Hill Rd, West Dover, VT 05356
    • /20

      Est $281,991 Not Listed For Sale

      149 Canal St, Brattleboro, VT 05301

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1899
      149 Canal St, Brattleboro, VT 05301

      Last Sold Summary

      • 28% Above List Price
      • $105/SF
      • 81 Days On Market

      Last Sold Price $220,000

      Last Listing Agent David Brown

  • /20

    $995,000

    • 3 Beds
    • 3.5 Baths
    • 1,800 Sq Ft

    56 Shattarack Rd Unit D6, Stratton, VT 05360

    Rare opportunity to own an exceptional ski-out/ski-back Slopeside unit at Stratton. This newly renovated 3-bedroom plus loft, 3.5-bathroom townhome offers spacious accommodations in a prime location that is both private and highly convenient. The expanded kitchen features elegant stone countertops and stainless steel appliances, perfect for both everyday meals and entertaining. The wood-burning

    Kim Morgan-Wohler Wohler Realty Group

    56 Shattarack Rd Unit D6, Stratton, VT 05360
  • /40

    $350,000 Sold Jan 09, 2026

    119 Main St, Putney, VT 05346

    • 4 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • Built 1798

    Last Sold Summary

    • 36% Below List Price
    • $183/SF
    • 136 Days On Market

    Current Estimated Value $356,842

    Last Listing Agent Heather Gleim CENTURY 21 North East

    119 Main St, Putney, VT 05346
    • /40

      Est $401,828 Not Listed For Sale

      392 Old Stage Rd, West Halifax, VT 05358

      • 1 Bed
      • 1 Bath
      • 1,416 Sq Ft
      • Built 2001
      392 Old Stage Rd, West Halifax, VT 05358

      Last Sold Summary

      • 6% Below List Price
      • $301/SF
      • 6 Days On Market

      Last Sold Price $426,000

      Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

  • /5

    $139,000

    • Land
    • 8.52 Acres
    • $16,315 per Acre

    0 Higley Hill, Dover, VT 05356

    Fantastic eastern views of New Hampshire mountains & valleys. A roadway, power & phone already exists for 4 dramatic view lots. Pick the one you want! Family & friends will enjoy ski area resort & local amenities nearby, while Brattleboro & CT River Valley resources are just down the hill. Truly majestic sites! Package lot offers considered. Appointment is required to walk the property.

    Michael Purcell Berkley & Veller Greenwood/Dover

    0 Higley Hill, Dover, VT 05356
  • /16

    $593,000 Sold Mar 31, 2025

    6 Johnson Hill Rd, Dover, VT 05356

    • 4 Beds
    • 3 Baths
    • 2,604 Sq Ft
    • Built 2006

    Last Sold Summary

    • 1% Below List Price
    • $228/SF
    • 14 Days On Market

    Current Estimated Value $623,917

    Last Listing Agent Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    6 Johnson Hill Rd, Dover, VT 05356
    • /4

      Est $489,578 Not Listed For Sale

      255 Minard Rd, Putney, VT 05346

      • 3 Beds
      • 2.5 Baths
      • 2,958 Sq Ft
      • Built 1986
      255 Minard Rd, Putney, VT 05346

      Last Sold Summary

      • 55% Above List Price
      • $106/SF
      • 0 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Heidi Bernier Berkley & Veller Greenwood Country

  • /2

    $70,000

    • Land
    • 2.01 Acres
    • $34,826 per Acre

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

    Amazing Opportunity to Build Your Forever Home!This beautiful south-facing, open lot offers the perfect setting for your dream home, with convenient access to power right at the road. The back portion of the property is graced with mature trees, providing shade and a natural pathway to nearby VAST snowmobile and hiking trails. Enjoy the peace of a quiet country setting where you can listen to

    Kerry Mulverhill

    0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

Showing Results 161 - 200, Page 5 of 18

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