30,780

Windham County, VT Homes

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  • /8

    $275,000 Under Contract

    • Land
    • 34.53 Acres
    • $7,964 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /15

    $2,300 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Condo for Rent

    58 Frost Place Unit Frost Place Duplex, Brattleboro, VT 05301

    This bright and beautifully maintained 3-bedroom apartment offers the perfect blend of convenience and tranquility in one of Brattleboro’s most desirable neighborhoods. Ideally situated within walking distance to downtown and the hospital, you’ll enjoy easy access to everything you need—while still being tucked away on a quiet street.It includes a generous outdoor space, where the

    58 Frost Place Unit Frost Place Duplex, Brattleboro, VT 05301
  • /34

    $200,000 Sold Oct 17, 2025

    533 Pratt Bridge Rd, Jamaica, VT 05343

    • 3 Beds
    • 2 Baths
    • 2,613 Sq Ft
    • Built 1970

    Last Sold Summary

    • 27% Below List Price
    • $77/SF
    • 25 Days On Market

    Current Estimated Value $225,463

    Last Listing Agent Mike England Michael England Real Estate

    533 Pratt Bridge Rd, Jamaica, VT 05343
    • /11

      Est $306,331 Not Listed For Sale

      48 Loop Rd, Newfane, VT 05345

      • 3 Beds
      • 2 Baths
      • 1,992 Sq Ft
      • Built 1973
      48 Loop Rd, Newfane, VT 05345

      Last Sold Summary

      • 17% Above List Price
      • $131/SF
      • 15 Days On Market
      • Last Sold Price $261,000
      • Nov 02, 2023

      Last Listing Agent A.J. Bellville Bellville Realty

  • /11

    $495,000 Under Contract

    • Land
    • 68.89 Acres
    • $7,185 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /7

    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 827 Sq Ft
    • Apartment for Rent

    4 Elliot St Unit 5, Brattleboro, VT 05301

    Corner apartment in downtown Brattleboro in the National is located on the corner of Elliot and Main Street. This two-bedroom apartment is in a secure building, laundry facilities on site, with parking down the street in the parking garage. Pets are welcome with an extra pet fee.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 5, Brattleboro, VT 05301
  • /54

    $1,743,600 Sold Sep 30, 2025

    1324 Middle Rd, Brattleboro, VT 05301

    • 7 Beds
    • 7.5 Baths
    • 8,718 Sq Ft
    • Built 2005

    Last Sold Summary

    • 50% Below List Price
    • $200/SF
    • 274 Days On Market

    Current Estimated Value $1,754,418

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    1324 Middle Rd, Brattleboro, VT 05301
    • /33

      Est $235,835 Not Listed For Sale

      849 Mcmillan Rd, Halifax, VT 05342

      • 1 Bed
      • 1 Bath
      • 856 Sq Ft
      • Built 2020
      849 Mcmillan Rd, Halifax, VT 05342

      Last Sold Summary

      • 11% Below List Price
      • $310/SF
      • 13 Days On Market
      • Last Sold Price $265,000
      • Dec 19, 2023

      Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

  • /12

    $999,000

    • Land
    • 12.2 Acres
    • $81,885 per Acre

    Higley Hill Rd, Wilmington, VT 05363

    Looking for Vermont land with privacy, natural beauty, and development potential? This 12.2-acre parcel in Windham County offers a peaceful escape tucked into the woods, ideal for buyers seeking recreational land, a homestead site, or a rural retreat. With 250 ft of road frontage on Higley Hill Rd, the property is easily accessible while still offering seclusion.The terrain is wooded and

    Community Lands Community Lands

    Higley Hill Rd, Wilmington, VT 05363
  • /30

    $1,300 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    210 Elliot St Unit 3, Brattleboro, VT 05301

    210 Elliot St Unit 3, Brattleboro, VT 05301
  • /59

    $360,000 Sold Sep 26, 2025

    45 Dorr Fitch Rd, West Dover, VT 05356

    • 5 Beds
    • 3.5 Baths
    • 2,800 Sq Ft
    • Built 1968

    Last Sold Summary

    • 14% Below List Price
    • $129/SF
    • 10 Days On Market

    Current Estimated Value $368,143

    Last Listing Agent Rich Caplan Deerfield Valley Real Estate

    45 Dorr Fitch Rd, West Dover, VT 05356
    • /32

      Est $471,323 Not Listed For Sale

      476 Edie Ln, Jamaica, VT 05343

      • 3 Beds
      • 3 Baths
      • 1,800 Sq Ft
      • Built 1988
      476 Edie Ln, Jamaica, VT 05343

      Last Sold Summary

      • 5% Above List Price
      • $249/SF
      • 40 Days On Market
      • Last Sold Price $449,000
      • Oct 25, 2024

      Last Listing Agent Carrie Mathews Winhall Real Estate

  • /7

    $195,000 Under Contract

    • Land
    • 15.27 Acres
    • $12,770 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /17

    $2,200 per month

    • 2 Beds
    • 1 Bath
    • 930 Sq Ft
    • Townhouse for Rent

    60 Brookside Dr Unit 3, Brattleboro, VT 05301

    This warm and inviting 2-bedroom condo comes fully furnished with everything you will need to just move in and relax. The first-floor open concept kitchen/living room makes for easy entertaining while you cook dinner. Upstairs are both bedrooms and the 3/4 bathroom. This comes with a full basement that has the washer and dryer and still usable space for storage or another room. This condo is not

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    60 Brookside Dr Unit 3, Brattleboro, VT 05301
  • /10

    $82,000 Sold Jan 07, 2026

    0 Old Ledge Rd Unit 4950217, Westminster, VT 05346

    • Land
    • 5 Acres
    • $16,400 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 928 Days On Market

    Last Listing Agent Christine Lewis Brattleboro Area Realty

    0 Old Ledge Rd Unit 4950217, Westminster, VT 05346
    • /24

      Est $248,201 Not Listed For Sale

      1751 Rockingham Rd, Rockingham, VT 05143

      • 2 Beds
      • 1.5 Baths
      • 1,120 Sq Ft
      • Built 1989
      1751 Rockingham Rd, Rockingham, VT 05143

      Last Sold Summary

      • 38% Above List Price
      • $161/SF
      • 14 Days On Market
      • Last Sold Price $180,000
      • Oct 20, 2023

      Last Listing Agent Thaddeus Abare Barrett and Valley Associates Inc.

  • /15

    $650,000 Under Contract

    • Land
    • 51.93 Acres
    • $12,517 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and

    Thom Milke Fountains Land Inc.

    0 W Hill Rd, Jamaica, VT 05343
  • /27

    $1,750 total monthly price

    • 1 Bed
    • 1.5 Baths
    • 835 Sq Ft
    • Condo for Rent

    18 Henry St Unit Townhouse-like Apartment, Bellows Falls, VT 05101

    18 Henry St Unit Townhouse-like Apartment, Bellows Falls, VT 05101
  • /46

    $480,000 Sold Oct 28, 2025

    28 Dover Green Rd, Dover, VT 05356

    • 4 Beds
    • 2 Baths
    • 2,092 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $229/SF
    • 29 Days On Market

    Current Estimated Value $457,285

    Last Listing Agent Kim Meeker Southern Vermont Realty Group

    28 Dover Green Rd, Dover, VT 05356
    • /14

      Not Listed For Sale

      5 Lahar Rd, Marlboro, VT 05351

      5 Lahar Rd, Marlboro, VT 05351

      Last Sold Summary

      • 9 Days On Market
      • Last Sold Price $140,000
      • Nov 30, 2023

      Last Listing Agent Jamie Watson BHG Masiello Keene

  • /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
  • /11

    $1,700 per month

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft
    • Apartment for Rent

    4 Elliot St Unit 2, Brattleboro, VT 05301

    Corner apartment in downtown Brattleboro in the National is located on the corner of Elliot and Main Street. This one-bedroom apartment is in a secure building, laundry facilities on site, with parking down the street in the parking garage. Pets are welcome with an extra pet fee.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 2, Brattleboro, VT 05301
  • /60

    $535,000 Sold Jun 20, 2025

    78 Pond Loop Unit M-2, Wilmington, VT 05363

    • 5 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • Built 1968

    Last Sold Summary

    • 8% Below List Price
    • $191/SF
    • 200 Days On Market

    Current Estimated Value $564,590

    Last Listing Agent Sigrid Pickering Chimney Hill Realty

    78 Pond Loop Unit M-2, Wilmington, VT 05363
    • /36

      Est $533,389 Not Listed For Sale

      208 Shady Ln, West Wardsboro, VT 05360

      • 3 Beds
      • 2.5 Baths
      • 2,050 Sq Ft
      • Built 2006
      208 Shady Ln, West Wardsboro, VT 05360

      Last Sold Summary

      • 2% Below List Price
      • $265/SF
      • 5 Days On Market
      • Last Sold Price $542,500
      • Oct 10, 2023

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  • /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
  • /2

    $2,000 total monthly price

    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft
    • Condo for Rent

    4 Carinthia Ln, West Dover, VT 05356

    3 bedrooms. 3-bathroom half duplex, 100 feet from the base lodge of Mount Snow. Willing to do a seasonal rental as well. 1400 square ft with finished lower level.

    4 Carinthia Ln, West Dover, VT 05356
  • /22

    $69,000 Sold Oct 03, 2025

    1051 Maple Hill Ln, Whitingham, VT 05342

    • Land
    • 10.01 Acres
    • $6,893 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    1051 Maple Hill Ln, Whitingham, VT 05342
    • /48

      Est $638,068 Not Listed For Sale

      418 Diers, Jamaica, VT 05343

      • 3 Beds
      • 2.5 Baths
      • 2,621 Sq Ft
      • Built 1988
      418 Diers, Jamaica, VT 05343

      Last Sold Summary

      • 1% Below List Price
      • $246/SF
      • 4 Days On Market
      • Last Sold Price $645,000
      • Mar 13, 2025

      Last Listing Agent Julie Lowe Lowe's Real Estate, LLC

  • /26

    $599,000

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

    10 Grouse Ln Unit 10A, Dover, VT 05356

    Owners open to offers! Stunning Post and Beam style townhome overlooking spectacular views of Mount Snow and Haystack ski trails with the sunsets in the west beyond. This private end unit features an amenity rich location thanks to direct VAST snowmobile trail access, hiking and biking trails in the summer, as well as easy access to the Mount Snow golf course which is directly through the

    Adam Palmiter Berkley & Veller Greenwood/Dover

    10 Grouse Ln Unit 10A, Dover, VT 05356
  • /11

    $1,550 per month

    • 1 Bed
    • 1 Bath
    • 524 Sq Ft
    • House for Rent

    722 Vermont 30, Townshend, VT 05353

    Single Family home located in Townshend, newly renovated with fresh paint and flooring. All rooms have natural light and plenty of windows to enjoy the nature right outside the window. This home has a large private yard, just minutes from shopping.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    722 Vermont 30, Townshend, VT 05353
  • /29

    $21,000 Sold Sep 26, 2025

    282Qtr.4 89 Grand Summit Way, Dover, VT 05356

    • 1 Bath
    • 332 Sq Ft
    • Built 1998

    Last Sold Summary

    • 7% Below List Price
    • $63/SF
    • 40 Days On Market

    Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

    282Qtr.4 89 Grand Summit Way, Dover, VT 05356
    • /40

      Not Listed For Sale

      965 Western Ave, Brattleboro, VT 05301

      • 4 Beds
      • 3 Baths
      • 2,358 Sq Ft
      • Built 1840
      965 Western Ave, Brattleboro, VT 05301

      Last Sold Summary

      • $157/SF
      • 55 Days On Market
      • Last Sold Price $370,000
      • Dec 06, 2024

      Last Listing Agent Kate Barry EXP Realty

  • /60

    $489,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,312 Sq Ft

    23 Wilsons Woods Rd, Brattleboro, VT 05301

    Welcome to 23 Wilsons Woods Road, a meticulously maintained Colonial-style home that offers the perfect Vermont balance: total wooded privacy combined with absolute convenience. Nestled at the end of a quiet road, this property feels like a secluded retreat tucked into the forest, yet you are literally moments away from Brattleboro’s vibrant restaurants, local shops, the hospital, and a thriving

    Kate Barry EXP Realty

    23 Wilsons Woods Rd, Brattleboro, VT 05301
  • /6

    $1,700 per month

    • 2 Beds
    • 1 Bath
    • 671 Sq Ft
    • Apartment for Rent

    1889 Vermont 30 Unit 1, Townshend, VT 05353

    First Floor 2 bedroom apartment with natural light, close to town and is available now. Off street parking and a yard make the location ideal. Apartment is not furnished

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    1889 Vermont 30 Unit 1, Townshend, VT 05353
  • /36

    $625,000 Sold Aug 20, 2025

    31 Joan's Ridge Rd, West Dover, VT 05356

    • 5 Beds
    • 3 Baths
    • 2,223 Sq Ft
    • Built 2012

    Last Sold Summary

    • 4% Below List Price
    • $281/SF
    • 126 Days On Market

    Current Estimated Value $622,195

    Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

    31 Joan's Ridge Rd, West Dover, VT 05356
    • /24

      Not Listed For Sale

      30 Styles Branch Rd Unit 307, Stratton, VT 05360

      • 4 Beds
      • 3.5 Baths
      • 1,178 Sq Ft
      • Built 1979
      30 Styles Branch Rd Unit 307, Stratton, VT 05360

      Last Sold Summary

      • $581/SF
      • 7 Days On Market
      • Last Sold Price $685,000
      • Sep 25, 2024

      Last Listing Agent Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  • /51

    $550,000

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft

    1886 Winhall Hollow Rd, South Londonderry, VT 05155

    Optimal Location, Competitively priced, Exceptional property tucked amidst nature with views toward Magic. Offering Main Residence and a large oversized detached garage/ barn with upstairs finished space and plenty of space for snow mobiles, ATVs and all your mountain vehicles and outdoor toys. Whether you're a weekend warrior looking to enjoy everything the Green Mountains have to offer or

    Kim Morgan-Wohler Wohler Realty Group

    1886 Winhall Hollow Rd, South Londonderry, VT 05155
  • /31

    $500 per month

    • 2 Baths
    • 352 Sq Ft
    • House for Rent

    21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146

    OFFICE SPACE AVAILABLE. The Windham Walkups now available for rent. Second floor office spaces now available above the Grafton Garage in Grafton Village VT. 5 separate office spaces are available and vary in rent based on size from $475-$650/month. Rent includes heat, electric and plowing. Shared parking area located just behind building. Two shared bathrooms and kitchenette space. Work remotely

    Jessica Landers Barrett and Valley Associates Inc.

    21 Vermont 121 Unit 1,2,4,5,6, Grafton, VT 05146
  • /36

    $230,000 Sold Apr 23, 2025

    1457 Rockingham Rd, Town of Rockingham, VT 05101

    • 4 Beds
    • 1 Bath
    • 1,600 Sq Ft
    • Built 1825

    Last Sold Summary

    • 49% Below List Price
    • $144/SF
    • 329 Days On Market

    Current Estimated Value $245,984

    Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

    1457 Rockingham Rd, Town of Rockingham, VT 05101
    • /17

      Est $462,130 Not Listed For Sale

      38 Summit Meadows Cir, Dover, VT 05356

      • 4 Beds
      • 3 Baths
      • 1,309 Sq Ft
      • Built 1984
      38 Summit Meadows Cir, Dover, VT 05356

      Last Sold Summary

      • 3% Below List Price
      • $363/SF
      • 12 Days On Market
      • Last Sold Price $475,000
      • Jul 21, 2024

      Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

Showing Results 41 - 80, Page 2 of 18

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