30,790

Windham County, VT Homes

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  • /33

    $19,500

    • 1 Bed
    • 1 Bath
    • 589 Sq Ft

    102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356

    Trailside! Use it, Rent it, Trade it! Does 13 weeks of vacation a year sound nice? Own this deeded quartershare property for 1 week every 28 days, on a rotating basis. This 1-of-a-kind, end-unit, slopeside 1-bedroom, 1 full bath unit has sleeping space for 4, and looks out over the Sundance Base Lodge and the Sundance Express, the new 6-person chairlift. Open-concept kitchen/dining room, and a

    Donna Brown Skihome Realty

    102, Qtr 4 Grand Summit Way Unit 102, Qtr 4, Dover, VT 05356
  • /43

    $229,300 Sold May 02, 2025

    129 Morningside Commons, Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 1,139 Sq Ft
    • Built 1998

    Last Sold Summary

    • $201/SF
    • 28 Days On Market

    Current Estimated Value $246,149

    Last Listing Agent Zachary Zupan EXP Realty

    129 Morningside Commons, Brattleboro, VT 05301
    • /23

      Est $500,367 Not Listed For Sale

      2 Ives Rd, Wilmington, VT 05363

      • 4 Beds
      • 3 Baths
      • 1,200 Sq Ft
      • Built 1960
      2 Ives Rd, Wilmington, VT 05363

      Last Sold Summary

      • 2% Below List Price
      • $425/SF
      • 159 Days On Market
      • Last Sold Price $510,000
      • Sep 01, 2023

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /2

    $370,000

    • 5 Beds
    • 4 Baths
    • 3,002 Sq Ft

    10 Birge St, Brattleboro, VT 05301

    Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

    Christine Lewis Brattleboro Area Realty

    10 Birge St, Brattleboro, VT 05301
  • /55

    $479,000 Sold Aug 22, 2025

    1 Dorr Fitch Rd, Dover, VT 05356

    • 4 Beds
    • 3 Baths
    • 2,566 Sq Ft
    • Built 1900

    Last Sold Summary

    • $187/SF
    • 1 Day On Market

    Current Estimated Value $478,151

    Last Listing Agent Donald Koelsch Deerfield Valley Real Estate

    1 Dorr Fitch Rd, Dover, VT 05356
    • /31

      Est $370,007 Not Listed For Sale

      962 Chapel Hill Rd, Whitingham, VT 05361

      • 3 Beds
      • 2 Baths
      • 1,963 Sq Ft
      • Built 1988
      962 Chapel Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 8% Above List Price
      • $174/SF
      • 7 Days On Market
      • Last Sold Price $342,000
      • Apr 26, 2024

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /16

    $19,999

    • Land
    • 1 Acre
    • $19,999 per Acre

    0 Hunter Brook Rd, South Newfane, VT 05351

    Beautiful creekside property in Newfane, ideal for camping, fishing, or RVing. The western boundary line follows Hunter Brook, which turns like a horseshoe at this location and almost meets the eastern boundary: Hunter Brook Road. As a result the property naturally divides itself into two sides, each with its own strengths and weaknesses.The northeastern side is larger, more private, and

    David White OwnerEntry.com

    0 Hunter Brook Rd, South Newfane, VT 05351
  • /30

    $1,000,000 Sold Jan 30, 2026

    585 Pleasant Valley Rd, Jamaica, VT 05343

    • Land
    • 108 Acres
    • $9,259 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 293 Days On Market

    Current Estimated Value $1,013,968

    Last Listing Agent Britt Wohler

    585 Pleasant Valley Rd, Jamaica, VT 05343
    • /31

      Est $106,520 Not Listed For Sale

      1124 Chapel Hill Rd, Whitingham, VT 05361

      1124 Chapel Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 433% Above List Price
      • 64 Days On Market
      • Last Sold Price $20,000
      • Jun 25, 2024

      Last Listing Agent Curtis Trousdale Preferred Properties

  • /9

    $480,000

    • Land
    • 7.8 Acres
    • $61,538 per Acre

    16 Overlook Dr, Dover, VT 05356

    A rare opportunity to own one of the last remaining lots in the prestigious Peaks/Greenspring community! This home development site offers 7.8 acres of land with a home site featuring full panoramic mountain and woodland views to the north and east, including mountain views to undeveloped national forest land. This property is the largest and most private lot in The Peaks community, providing a

    Patricia Fitzpatrick Skihome Realty

    16 Overlook Dr, Dover, VT 05356
  • /28

    $460,000 Sold May 01, 2025

    70 Tyler St, Brattleboro, VT 05301

    • 4 Beds
    • 1.5 Baths
    • 2,051 Sq Ft
    • Built 1920

    Last Sold Summary

    • $224/SF
    • 0 Days On Market

    Current Estimated Value $471,510

    Last Listing Agent Karen Hoppe Berkley & Veller Greenwood Country

    70 Tyler St, Brattleboro, VT 05301
    • /26

      Est $255,879 Not Listed For Sale

      2815 Burrington Hill Rd, Whitingham, VT 05361

      • 1 Bed
      • 1 Bath
      • 700 Sq Ft
      • Built 1982
      2815 Burrington Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 11% Above List Price
      • $329/SF
      • 6 Days On Market
      • Last Sold Price $230,000
      • Jan 05, 2024

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /15

    $59,000 Under Contract

    • Land
    • 3.58 Acres
    • $16,480 per Acre

    Lot 4 Ghastly Job Way, Wilmington, VT 05363

    3.58 acres east of Wilmington village. This property is ready to build on, site work has commenced; tree clearing and partial driveway installed, fully engineered, survey, and Sate of Vermont Wastewater Permit for the construction of a three bedroom home. This parcel offers a great location, close to Lake Raponda for swimming, near Molly Stark State Park for hiking and minutes to Lake Whitingham

    Monique White Deerfield Valley Real Estate

    Lot 4 Ghastly Job Way, Wilmington, VT 05363
  • /44

    $359,350 Sold Sep 26, 2025

    399 Laurel Lake Rd, Jacksonville, VT 05342

    • 2 Beds
    • 3 Baths
    • 1,696 Sq Ft
    • Built 1930

    Last Sold Summary

    • 10% Below List Price
    • $212/SF
    • 17 Days On Market

    Current Estimated Value $341,076

    Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

    399 Laurel Lake Rd, Jacksonville, VT 05342
    • /12

      Est $345,500 Not Listed For Sale

      2027 Burrington Hill Rd, Whitingham, VT 05361

      2027 Burrington Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 47% Above List Price
      • 262 Days On Market
      • Last Sold Price $235,000
      • Oct 06, 2023

      Last Listing Agent Kristen Breeden Southern Vermont Realty Group

  • /43

    $799,000

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

    39D Dover Springs Ln, Dover, VT 05356

    Located in the highly sought-after Greensprings community at Mount Snow, this spacious 4 bedroom, 4 bath townhouse offers the perfect blend of comfort, convenience, and year-round recreation.The bright, open-concept main living area features vaulted ceilings, abundant natural light, and a cozy fireplace ideal for gathering after a day on the slopes. Large windows and sliding doors invite the

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    39D Dover Springs Ln, Dover, VT 05356
  • /34

    $405,000 Sold May 23, 2025

    47B Suntec Loop, Dover, VT 05356

    • 3 Beds
    • 3 Baths
    • 1,768 Sq Ft
    • Built 1982

    Last Sold Summary

    • 10% Below List Price
    • $229/SF
    • 131 Days On Market

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

    47B Suntec Loop, Dover, VT 05356
    • /29

      Est $517,326 Not Listed For Sale

      960 Holbrook Rd, Jacksonville, VT 05342

      • 3 Beds
      • 2 Baths
      • 2,600 Sq Ft
      • Built 1968
      960 Holbrook Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 1% Below List Price
      • $202/SF
      • 14 Days On Market
      • Last Sold Price $525,000
      • Aug 04, 2023

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /38

    $399,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft

    75 E Birch Rd Unit 35, Stratton, VT 05360

    Beautifully updated top-floor condominium located in Stratton Village, offering breathtaking views of Stratton Mountain. The Vantage Point community is ideally positioned to provide a sense of privacy while remaining just minutes from all the year-round amenities Stratton has to offer. A short stroll leads to the Stratton Fitness Center, featuring tennis and pickleball courts, an indoor pool, and

    Kristin Pirie Winhall Real Estate

    75 E Birch Rd Unit 35, Stratton, VT 05360
  • /11

    $153,000 Sold Aug 25, 2025

    41 Old Depot Rd, Putney, VT 05346

    • Land
    • 4.53 Acres
    • $33,775 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 33 Days On Market

    Current Estimated Value $521,129

    Last Listing Agent Victoria Woods Brattleboro Area Realty

    41 Old Depot Rd, Putney, VT 05346
    • /40

      Est $421,441 Not Listed For Sale

      656 Allard Rd, Whitingham, VT 05361

      • 4 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1949
      656 Allard Rd, Whitingham, VT 05361

      Last Sold Summary

      • 9% Above List Price
      • $192/SF
      • 56 Days On Market
      • Last Sold Price $385,000
      • Feb 14, 2024

      Last Listing Agent Craig Ruggless EXP Realty

  • /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
  • /37

    $370,000 Sold Feb 12, 2026

    3298 Houghtonville Rd, Grafton, VT 05146

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 1890

    Last Sold Summary

    • 6% Below List Price
    • $154/SF
    • 44 Days On Market

    Current Estimated Value $388,085

    Last Listing Agent Alison Cummings Cummings & Co

    3298 Houghtonville Rd, Grafton, VT 05146
    • /32

      Est $233,530 Not Listed For Sale

      329 Deer Hill Rd, Whitingham, VT 05361

      • 2 Beds
      • 1 Bath
      • 952 Sq Ft
      • Built 1968
      329 Deer Hill Rd, Whitingham, VT 05361

      Last Sold Summary

      • 2% Above List Price
      • $241/SF
      • 6 Days On Market
      • Last Sold Price $229,900
      • Sep 01, 2023

      Last Listing Agent Jon Tourville

  • /26

    $899,000

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

    1C Townhouse Square Unit 7, Dover, VT 05356

    Experience true ski-in/ski-out living at Mount Snow in the highly desirable Seasons on Mount Snow community - on Tin Lizzy, and just seconds to the lift. This spacious 3-bedroom, 3.5-bath townhouse offers a thoughtful and functional layout, including two private en suite bedrooms for added comfort and flexibility. Two separate living areas provide ample space for entertaining and relaxing, while

    Stephanie Sugden Real Broker LLC

    1C Townhouse Square Unit 7, Dover, VT 05356
  • /26

    $520,000 Sold Sep 25, 2025

    18 Old Town Rd, West Dover, VT 05356

    • 3 Beds
    • 1.5 Baths
    • 2,145 Sq Ft
    • Built 1981

    Last Sold Summary

    • 5% Below List Price
    • $242/SF
    • 15 Days On Market

    Current Estimated Value $525,290

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    18 Old Town Rd, West Dover, VT 05356
    • /39

      Est $557,185 Not Listed For Sale

      3358 Vt Route 100, Whitingham, VT 05361

      • 5 Beds
      • 5 Baths
      • 3,300 Sq Ft
      • Built 1900
      3358 Vt Route 100, Whitingham, VT 05361

      Last Sold Summary

      • 7% Below List Price
      • $182/SF
      • 118 Days On Market
      • Last Sold Price $599,000
      • May 10, 2024

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /18

    $299,000

    • Land
    • 1.06 Acres
    • $282,075 per Acre

    12 Someday Rd, Dover, VT 05356

    Located in the prestigious Someday neighborhood of West Dover,VT this 1.06-acre building lot offers a unique opportunity to create your dream home with breathtaking views of Mount Snow ski resort. The lot, which once housed the original Someday homestead as your footprint, it is now ready for its next chapter. With a permit for sewer in place for a 6-bedroom home, the property provides a head

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    12 Someday Rd, Dover, VT 05356
  • /39

    $475,000 Sold Apr 23, 2025

    101 Washington St, Brattleboro, VT 05301

    • 5 Beds
    • 2.5 Baths
    • 2,823 Sq Ft
    • Built 1905

    Last Sold Summary

    • $168/SF
    • 121 Days On Market

    Current Estimated Value $504,567

    Last Listing Agent Thomas Dahlin Berkley & Veller Greenwood Country

    101 Washington St, Brattleboro, VT 05301
    • /29

      Est $582,638 Not Listed For Sale

      55 Reed Hill Rd, Jacksonville, VT 05342

      • 5 Beds
      • 3 Baths
      • 2,732 Sq Ft
      • Built 1840
      55 Reed Hill Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 1% Below List Price
      • $216/SF
      • 35 Days On Market
      • Last Sold Price $590,000
      • Oct 28, 2024

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

  • /11

    $250,000

    • Land
    • 18 Acres
    • $13,889 per Acre

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

    Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

    Christine Lewis Brattleboro Area Realty

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
  • /22

    $89,900 Sold Jan 23, 2026

    2 Wagon Dr, Brattleboro, VT 05301

    • 2 Beds
    • 2 Baths
    • 910 Sq Ft
    • Built 1977

    Last Sold Summary

    • $99/SF
    • 6 Days On Market

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    2 Wagon Dr, Brattleboro, VT 05301
    • /35

      Est $292,684 Not Listed For Sale

      159 Reed Hill Rd, Jacksonville, VT 05342

      • 3 Beds
      • 3 Baths
      • 1,626 Sq Ft
      • Built 1959
      159 Reed Hill Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 10% Below List Price
      • $200/SF
      • 18 Days On Market
      • Last Sold Price $326,000
      • Nov 01, 2023

      Last Listing Agent Jacki Murano Southern Vermont Realty Group

  • /51

    $899,800

    • 5 Beds
    • 8 Baths
    • 7,430 Sq Ft

    925 Hinesburg Rd, Brattleboro, VT 05301

    Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

    Christine Lewis Brattleboro Area Realty

    925 Hinesburg Rd, Brattleboro, VT 05301
  • /19

    $400,000 Sold Dec 15, 2025

    48 Landing Ln, Wilmington, VT 05363

    • 4 Beds
    • 2 Baths
    • 2,056 Sq Ft
    • Built 2003

    Last Sold Summary

    • 20% Below List Price
    • $195/SF
    • 52 Days On Market

    Current Estimated Value $425,205

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    48 Landing Ln, Wilmington, VT 05363
    • /40

      Est $517,783 Not Listed For Sale

      371 Butler Brook Rd, Jacksonville, VT 05342

      • 5 Beds
      • 2.5 Baths
      • 2,296 Sq Ft
      • Built 1976
      371 Butler Brook Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 7% Below List Price
      • $242/SF
      • 152 Days On Market
      • Last Sold Price $555,000
      • May 03, 2024

      Last Listing Agent Monica Sumner BHG Masiello Brattleboro

  • /35

    $34,900

    • 1 Bed
    • 2 Baths
    • 745 Sq Ft

    341/43 Qtr.4,89 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 (341) Queen murphy bed, kitchenette, full bathroom . Hotel unit (343) Two king beds, full bathroom. Units are located on the third floor mountain side of the hotel. Lock out units have the benefit of using the unit as a whole or stay in one side and rent the other

    Kelly Agrillo Southern Vermont Realty Group

    341/43 Qtr.4,89 Grand Summit Way, Dover, VT 05356
  • /12

    $325,000 Sold Feb 20, 2026

    16 Sycamore St, Brattleboro, VT 05301

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1992

    Last Sold Summary

    • 1% Below List Price
    • $339/SF
    • 10 Days On Market

    Current Estimated Value $317,750

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    16 Sycamore St, Brattleboro, VT 05301
    • /17

      Est $166,175 Not Listed For Sale

      813 Gates Pond Rd, Jacksonville, VT 05342

      • 2 Beds
      • 1 Bath
      • 826 Sq Ft
      • Built 1846
      813 Gates Pond Rd, Jacksonville, VT 05342

      Last Sold Summary

      • 4% Above List Price
      • $194/SF
      • 5 Days On Market
      • Last Sold Price $160,000
      • Jul 10, 2023

      Last Listing Agent Melissa Nebelski Real Broker LLC

  • /8

    $65,000

    • Land
    • 2 Acres
    • $32,500 per Acre

    585 Sawmill Rd, Stratton, VT 05360

    Ready to build! Nestled in the picturesque Snow Mountain Farms development, this prime 2 acre property offers the perfect canvas for your dream home. Situated in a great neighborhood with a convenient location, it provides easy access to both Mount Snow and Stratton. The property is equipped with a wastewater permit, septic design, an already cleared building envelope, and a driveway. Association

    Carrie Mathews Winhall Real Estate

    585 Sawmill Rd, Stratton, VT 05360

Showing Results 321 - 360, Page 9 of 18

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