31,018

Windham County, VT Homes

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  • /51

    $799,000

    • 4 Beds
    • 5 Baths
    • 3,992 Sq Ft

    1035 Vermont 121, Windham, VT 05359

    Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A

    Jamie Wylie Stratton Real Estate

    1035 Vermont 121, Windham, VT 05359
  • /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

    $405,500

    Sold Jan 29, 2026

    44 Villager Loop, Dover, VT 05356

    • 3 Beds
    • 3 Baths
    • 2,144 Sq Ft
    • Built 1987

    Last Sold Summary

    • 25% Below List Price
    • $189/SF
    • 480 Days On Market

    Current Estimated Value $410,088

    Last Listing Agent Janet Boyd Boyd Real Estate

    44 Villager Loop, Dover, VT 05356
    • /26

      Est $370,103

      Not Listed For Sale

      157 Pine St, Brattleboro, VT 05301

      • 3 Beds
      • 1.5 Baths
      • 1,435 Sq Ft
      • Built 1890
      157 Pine St, Brattleboro, VT 05301

      Last Sold Summary

      • 22 Days On Market

  • /33

    $915,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,529 Sq Ft

    761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360

    A rare opportunity in Long Trail House, this corner residence has been thoughtfully reimagined from two separate units into a spacious, fully renovated retreat designed for flexible living. The expanded layout now includes multiple sleeping areas and a den/office, offering versatility for guests or remote work. Natural light fills the home thanks to its corner position, while open living space

    Edwin Kevil Stratton Real Estate

    761 Stratton Mountain Access Rd Unit 321/323, Stratton, VT 05360
  • /14

    $65,000 Per Month

    • 3 Beds
    • 5 Baths
    • 2,600 Sq Ft
    • Condo for Rent

    790 Stratton Access, Stratton, VT 05155

    Designed for the ultimate winter ski season, this home offers multiple gathering spaces to unwind after a day on the mountain. Gather around the impressive stone wood-burning fireplace in the main living room, challenge each other to a game of pool in the expansive recreation room, or simply savor the warmth of this inviting mountain retreat. Three generously sized bedrooms, including a spacious

    Christine Chovan

    790 Stratton Access, Stratton, VT 05155
  • /37

    $340,000

    Sold Aug 14, 2025

    290 Melendy Hill Rd, South Londonderry, VT 05155

    • 3 Beds
    • 3 Baths
    • 2,809 Sq Ft
    • Built 1936

    Last Sold Summary

    • 15% Below List Price
    • $121/SF
    • 159 Days On Market

    Current Estimated Value $351,322

    Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home

    290 Melendy Hill Rd, South Londonderry, VT 05155
    • /29

      Est $378,090

      Not Listed For Sale

      28 Greenleaf St, Brattleboro, VT 05301

      • 2 Beds
      • 1.5 Baths
      • 1,620 Sq Ft
      • Built 2006
      28 Greenleaf St, Brattleboro, VT 05301

      Last Sold Summary

      • 10 Days On Market

  • /30

    $1,060,000

    • 3 Beds
    • 3 Baths
    • 1,587 Sq Ft

    778 Stratton Mountain Access Rd Unit 2401, Stratton, VT 05155

    Enjoy elevated mountain living from this top-floor corner residence in Mountain Watch, ideally positioned with expansive valley views and access to the Villager Lift. Bright interiors, abundant natural light, and two private balconies create inviting spaces to take in the surrounding scenery throughout every season. The updated kitchen and bathrooms offer modern finishes while maintaining the

    Jamie Wylie Stratton Real Estate

    778 Stratton Mountain Access Rd Unit 2401, Stratton, VT 05155
  • /24

    $2,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    776 Old Route 8, Jamaica, VT 05343

    Welcome home to this beautifully renovated 3-bedroom, 2-bath single-family residence nestled on a peaceful 1⁄2-acre lot with direct access to a tranquil brook. This rental comes fully furnished. Blending modern updates with the serenity of nature, this property offers the perfect balance of comfort and outdoor living. Step inside to discover a thoughtfully updated interior featuring bright,

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    776 Old Route 8, Jamaica, VT 05343
  • /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 $233,328

    Last Listing Agent Mike England Michael England Real Estate

    533 Pratt Bridge Rd, Jamaica, VT 05343
    • /27

      Est $487,154

      Not Listed For Sale

      32 Christie Ln, Brattleboro, VT 05301

      • 3 Beds
      • 2.5 Baths
      • 2,832 Sq Ft
      • Built 1985
      32 Christie Ln, Brattleboro, VT 05301

      Last Sold Summary

      • 12 Days On Market

  • /21

    $290,000

    • Land
    • 289.12 Acres
    • $1,003 per Acre

    2817 Lt 22, Jamaica, VT 05343

    Windham Woods Forest offers 289.12 acres of productive, predominantly hardwood timberland in the scenic southern Green Mountains of Jamaica, VT, an area prized for sparse development, strong wildlife habitat, and proximity to the Green Mountain National Forest and Stratton Mountain Resort. The property boasts significant Legal Trail frontage on both Black Bear and Melis Roads and sits directly on

    Zach Jaminet Fountains Land

    2817 Lt 22, Jamaica, VT 05343
  • /16

    $2,200 Per Month

    • 2 Beds
    • 1 Bath
    • 1,525 Sq Ft
    • Apartment for Rent

    78 Central St Unit 78, Brattleboro, VT 05301

    This second floor, two-bedroom apartment in town on a quiet side street. This unit has had some updates to the kitchen and bathroom, along with fresh paint throughout. The rooms have amazing sunlight throughout the day and enjoy the evenings on your enclosed porch. This is close to shopping, public transportation and schools. Rent does not include any utilities. Photos are virtually staged,

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    78 Central St Unit 78, 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 $1,741,095

    Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

    1324 Middle Rd, Brattleboro, VT 05301
    • /48

      Est $315,256

      Not Listed For Sale

      52 Belmont Ave, Brattleboro, VT 05301

      • 3 Beds
      • 1.5 Baths
      • 1,300 Sq Ft
      • Built 1924
      52 Belmont Ave, Brattleboro, VT 05301

      Last Sold Summary

      • 57 Days On Market

  • /12

    $99,000

    $900K PRICE DROP
    • Land
    • 12.2 Acres
    • $8,115 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
  • /10

    $2,400 Per Month

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

    114 Main St Unit 31, Brattleboro, VT 05301

    Newly renovated third floor two bedroom apartment with a large window with in-town views. Access to everything you need within a few blocks. Enjoy the downtown scene with restaurants and breweries right on the same block. This one room apartment has its own washer and dryer in the unit. Pictures are virtually staged, apartment is not furnished.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    114 Main St Unit 31, 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 $350,496

    Last Listing Agent Rich Caplan Deerfield Valley Real Estate

    45 Dorr Fitch Rd, West Dover, VT 05356
    • /25

      Est $109,741

      Not Listed For Sale

      13 Pine St, Bellows Falls, VT 05101

      • 5 Beds
      • 3 Baths
      • 3,900 Sq Ft
      • Built 1900
      13 Pine St, Bellows Falls, VT 05101

      Last Sold Summary

      • 8 Days On Market

  • /52

    $499,000

    • 5 Beds
    • 4 Baths
    • 3,665 Sq Ft

    522 Vermont Route 100, Wardsboro, VT 05355

    Dating to the 1830s and thoughtfully renovated through the 1990s and early 2000s, this Vermont homestead blends historic character with the comforts of modern living. Set on 12 mostly open, level acres surrounded by mountains, it offers the kind of setting people dream about but rarely find. Start your morning with coffee overlooking the meadow as mist rises from the fields and the sound of the

    Lee Brown Four Seasons Sotheby's Int'l Realty

    522 Vermont Route 100, Wardsboro, VT 05355
  • /32

    $4,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,080 Sq Ft
    • House for Rent

    194 Main St, Grafton, VT 05146

    VACATION RENTAL. In the center of Grafton Village find the refined Phebe Frost house. Beautifully maintained and thoughtfully decorated, spend some special time in Vermont! Lovely features include wood floors, double sided fireplace in living and dining, comfortable family room/den and stocked pantry. Delightful master suite on main floor and two additional bedrooms bookend a full bath upstairs.

    Jessica Landers Barrett and Valley Associates Inc.

    194 Main St, Grafton, VT 05146
  • /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
    • /28

      Est $623,910

      Not Listed For Sale

      12 Conifer Ln, Wilmington, VT 05363

      • 3 Beds
      • 2.5 Baths
      • 2,100 Sq Ft
      • Built 2010
      12 Conifer Ln, Wilmington, VT 05363

      Last Sold Summary

      • 81 Days On Market

  • /42

    $489,999

    • 3 Beds
    • 2 Baths
    • 1,410 Sq Ft

    7 High Top Unit B117, Wilmington, VT 05363

    Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and

    Sigrid Pickering Chimney Hill Realty

    7 High Top Unit B117, Wilmington, VT 05363
  • /9

    $1,700 Per Month

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

    4 Elliot St Unit 11, Brattleboro, VT 05301

    In town, one bedroom apartment, with bright sunlit rooms. The apartment has a combined kitchen and living room, with a separate bedroom. Coin operated laundry is on site, trash removal, and a secure building. Pet friendly building, Photos are virtually staged and apartment is not furnished.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 11, Brattleboro, VT 05301
  • /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 $497,765

    Last Listing Agent Kim Meeker Southern Vermont Realty Group

    28 Dover Green Rd, Dover, VT 05356
    • /60

      Not Listed For Sale

      7 Deepwood Park, Brattleboro, VT 05301

      • 3 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1987
      7 Deepwood Park, Brattleboro, VT 05301

      Last Sold Summary

      • 204 Days On Market

  • /32

    $495,000

    • 3,882 Sq Ft

    1309 Putney Rd, Brattleboro, VT 05301

    Exceptional investment opportunity! This well maintained six-unit property is in outstanding condition and has seen numerous recent improvements, making it an attractive addition to any investment portfolio. Exterior updates include fresh paint completed last year, newer windows (approximately three years old), a newer rubber membrane roof, buried power, updated electrical, a newer hot water

    Kerry Mulverhill

    1309 Putney Rd, Brattleboro, VT 05301
  • /33

    $18,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,250 Sq Ft
    • House for Rent

    22 Reynolds Ln, Jamaica, VT 05343

    Escape to the mountains and enjoy winter the way it was meant to be experienced. Located just 5.5 miles from Stratton's Sun Bowl, this newly constructed 3-bedroom, 2.5-bath home offers the perfect setting for ski weekends, holiday gatherings, and memorable mountain getaways. Thoughtfully designed with a modern mountain aesthetic, the home features soaring ceilings, warm wood finishes, and

    Cheyanne Pugliese

    22 Reynolds Ln, Jamaica, VT 05343
  • /32

    $190,000

    Sold Apr 29, 2026

    36 Barker St, Town of Rockingham, VT 05101

    • 3,302 Sq Ft
    • Built 1880

    Last Sold Summary

    • 17% Below List Price
    • $58/SF
    • 9 Days On Market

    Current Estimated Value $190,845

    Last Listing Agent Rob Weltz Barrett and Valley Associates Inc.

    36 Barker St, Town of Rockingham, VT 05101
    • /17

      Not Listed For Sale

      8 Brickyard Rd, Dover, VT 05341

      8 Brickyard Rd, Dover, VT 05341

      Last Sold Summary

      • 30 Days On Market

  • /7

    $399,000

    • Land
    • 30 Acres
    • $13,300 per Acre

    Lot X Tyanoga Rd, Whitingham, VT 05361

    Spectacular opportunity to own a rare waterfront building lot on Lake Sadawga in Southern Vermont. This lot sits on a private dead end corner with southern exposure, private lake frontage including an earthen dam, and easy access along this pristine, natural lake. There is additional frontage along Stimpson Hill Road. The lake offers tremendous fishing, kayaking, canoeing, water sports, and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot X Tyanoga Rd, Whitingham, VT 05361
  • /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. PICTURES ARE VIRTUALLY STAGED - APARTMENT IS NOT FURNISHED

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    4 Elliot St Unit 5, Brattleboro, VT 05301
  • /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
    • /10

      Not Listed For Sale

      42-44 Canal St, Brattleboro, VT 05301

      42-44 Canal St, Brattleboro, VT 05301

      Last Sold Summary

      • 2 Days On Market

  • /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
  • /14

    $2,100 Per Month

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    23 Turner Hill Rd, Grafton, VT 05146

    Charming single-family home located in Grafton, Vermont. This well-maintained 3-bedroom, 2-bath home offers comfort, space, and a rural setting. The home will be unfurnished and features a bright living area, open diningroom/kitchen and nice sized bedrooms. It has easy access to local amenities, outdoor recreation, and nearby towns. $2,100/month plus all utilities & services. Annual

    Team BVA Rentals Barrett and Valley Associates Inc.

    23 Turner Hill Rd, Grafton, VT 05146
  • /24

    $92,999

    Sold May 11, 2026

    201 Shady Pines, Westminster, VT 05158

    • 2 Beds
    • 2 Baths
    • 790 Sq Ft
    • Built 2024

    Last Sold Summary

    • $118/SF
    • 348 Days On Market

    Last Listing Agent Kate Barry EXP Realty

    201 Shady Pines, Westminster, VT 05158
    • /46

      Not Listed For Sale

      128 Spaulding Hill Rd, Dummerston, VT 05346

      • 4 Beds
      • 5 Baths
      • 4,337 Sq Ft
      • Built 1989
      128 Spaulding Hill Rd, Dummerston, VT 05346

      Last Sold Summary

      • 8 Days On Market

Showing Results 41 - 80, Page 2 of 18

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