30,889

Windham County, VT Homes

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  • /15

    $650,000

    $200K PRICE DROP 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
  • /16

    $2,200 Per Month

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

    80 Central St, 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

    80 Central St, Brattleboro, VT 05301
  • /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
    • /26

      Not Listed For Sale

      1 Wildwood Dr, West Brattleboro, VT 05301

      • 2 Beds
      • 1 Bath
      • 962 Sq Ft
      • Built 1977
      1 Wildwood Dr, West Brattleboro, VT 05301

      Last Sold Summary

      • 12 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
  • /7

    $1,500 Per Month

    • 1 Bed
    • 225 Sq Ft
    • Apartment for Rent

    114 Main St Unit 36, Brattleboro, VT 05301

    Newly renovated third floor studio 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 36, Brattleboro, VT 05301
  • /46

    $450,000

    Sold May 15, 2026

    214 Putney Rd, Brattleboro, VT 05301

    • 4 Beds
    • 2.5 Baths
    • 2,756 Sq Ft
    • Built 1940

    Last Sold Summary

    • 9% Below List Price
    • $163/SF
    • 46 Days On Market

    Current Estimated Value $498,988

    Last Listing Agent Keith Nowak Four Seasons Sotheby's Int'l Realty

    214 Putney Rd, Brattleboro, VT 05301
    • /32

      Not Listed For Sale

      97 Stratton Dr, Townshend, VT 05353

      • 5 Beds
      • 4.5 Baths
      • 3,529 Sq Ft
      • Built 1830
      97 Stratton Dr, Townshend, VT 05353

      Last Sold Summary

      • 118 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
  • /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
  • /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
    • /21

      Est $331,077

      Not Listed For Sale

      443 Dover Rd, Newfane, VT 05351

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1996
      443 Dover Rd, Newfane, VT 05351

      Last Sold Summary

      • 8 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
  • /10

    $1,700 Per Month

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

    114 Main St Unit 37, Brattleboro, VT 05301

    Newly Renovated apartment. Located on the 3rd floor of 114 Main Street, this apartment has its own washer and dryer in the unit. Heat is included and pets are welcome. A nice big window with views of downtown allows so much sunlight into the space. Dedicated free parking can be used at the 215 Main Street tenant parking lot. Apartment is not furnished, photos are virtually staged.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    114 Main St Unit 37, Brattleboro, VT 05301
  • /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 $604,701

    Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

    31 Joan's Ridge Rd, West Dover, VT 05356
    • /35

      Est $594,970

      Not Listed For Sale

      10 Lower Highlands Rd, Dover, VT 05356

      • 6 Beds
      • 3.5 Baths
      • 2,517 Sq Ft
      • Built 1970
      10 Lower Highlands Rd, Dover, VT 05356

      Last Sold Summary

      • 126 Days On Market

  • /24

    $495,000

    $55K PRICE DROP
    • 4,116 Sq Ft

    33 Oak St, Brattleboro, VT 05301

    This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the

    Kate Barry EXP Realty

    33 Oak St, Brattleboro, VT 05301
  • /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
  • /2

    $700,000

    Sold Jul 21, 2025

    40 Founders Hill Rd, Stratton, VT 05360

    • 4 Beds
    • 2 Baths
    • 1,084 Sq Ft
    • Built 1960

    Last Sold Summary

    • $646/SF
    • 0 Days On Market

    Current Estimated Value $712,620

    Last Listing Agent Margretta Fischer Wohler Realty Group

    40 Founders Hill Rd, Stratton, VT 05360
    • /19

      Not Listed For Sale

      43 High Point Dr Unit D23, Stratton, VT 05360

      • 2 Beds
      • 2 Baths
      • 1,130 Sq Ft
      • Built 1983
      43 High Point Dr Unit D23, Stratton, VT 05360

      Last Sold Summary

      • 8 Days On Market

  • /15

    $67,500

    $12K PRICE DROP
    • 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
  • /15

    $2,200 Per Month

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

    78 Central St, Brattleboro, VT 05301

    This first 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, Brattleboro, VT 05301
  • /48

    $750,000

    Sold Aug 14, 2025

    573 Middletown Rd, Londonderry, VT 05148

    • 4 Beds
    • 3.5 Baths
    • 2,573 Sq Ft
    • Built 1989

    Last Sold Summary

    • 18% Below List Price
    • $291/SF
    • 141 Days On Market

    Current Estimated Value $750,469

    Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    573 Middletown Rd, Londonderry, VT 05148
    • /40

      Est $517,000

      Not Listed For Sale

      2900 Route 121 E, Grafton, VT 05146

      • 3 Beds
      • 2 Baths
      • 1,613 Sq Ft
      • Built 2006
      2900 Route 121 E, Grafton, VT 05146

      Last Sold Summary

      • 6 Days On Market

  • /31

    $695,000

    $170K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 2,481 Sq Ft

    1871 W Hill Rd, Townshend, VT 05353

    OPEN HOUSE - Sunday, May 24 from 2:00 - 4:00. Welcome to your fully furnished chalet-style escape in Townshend, Vermont. Set on 10 partially cleared, usable acres, this 2-bedroom, 2-bathroom home offers the perfect blend of privacy, comfort, and classic Vermont charm. Featuring additional living space in the loft and den, this property provides flexibility.Step inside to find a warm, inviting

    Kim Meeker Southern Vermont Realty Group

    1871 W Hill Rd, Townshend, VT 05353
  • /12

    $1,750 Per Month

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

    788 Vermont 30 Unit 1, Newfane, VT 05345

    Welcome to the Tiny Home Village located in Newfane. This is the first one in the new village for rent. This is a fully furnished home, with available garden space and a storage shed for your use. This tiny home is located on the backside of the Newfane Flea Market. Its available immediately. Set up your tour today

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    788 Vermont 30 Unit 1, Newfane, VT 05345
  • /35

    $120,000

    Sold Mar 20, 2026

    406 Fox Mountain Rd, Wilmington, VT 05363

    • Land
    • 1.52 Acres
    • $78,947 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 302 Days On Market

    Last Listing Agent Sigrid Pickering Chimney Hill Realty

    406 Fox Mountain Rd, Wilmington, VT 05363
    • /34

      Est $769,773

      Not Listed For Sale

      5 Rice Hill Rd, Dover, VT 05341

      • 4 Beds
      • 3.5 Baths
      • 3,412 Sq Ft
      • Built 1989
      5 Rice Hill Rd, Dover, VT 05341

      Last Sold Summary

      • 108 Days On Market

  • /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
  • /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
  • /44

    $500,000

    Sold Jul 07, 2025

    19 Grimes Hill Rd, Newfane, VT 05345

    • 4 Beds
    • 3.5 Baths
    • 3,588 Sq Ft
    • Built 1840

    Last Sold Summary

    • 13% Below List Price
    • $139/SF
    • 40 Days On Market

    Current Estimated Value $531,246

    Last Listing Agent Kristen Ziter Taylor Brattleboro Area Realty

    19 Grimes Hill Rd, Newfane, VT 05345
    • /33

      Est $197,831

      Not Listed For Sale

      951 Dover Rd, South Newfane, VT 05351

      • 2 Beds
      • 1 Bath
      • 1,369 Sq Ft
      • Built 1900
      951 Dover Rd, South Newfane, VT 05351

      Last Sold Summary

      • 9 Days On Market

  • /24

    $799,999

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,592 Sq Ft

    62 Potter Rd, Wardsboro, VT 05355

    Brand-new construction in process in Wardsboro, set on a spacious 2-acre parcel. Introducing a brand-new 3-bedroom, 3.5-bath home is slated for completion in late fall 2026. Inside, you’ll find beautiful natural light, wide-plank pine flooring, oversized windows, and an inviting, bright living space. The main level offers an open-concept layout with a well-appointed kitchen, dining area, and

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    62 Potter Rd, Wardsboro, VT 05355
  • /9

    $2,500 Per Month

    • 3 Beds
    • 1 Bath
    • 850 Sq Ft
    • Apartment for Rent

    110 Estey St Unit 1, Brattleboro, VT 05301

    First Floor 3-bedroom apartment on a quiet side street that is close to public transportation, hospitals and shopping. Newly painted and new flooring this unit has its own washer and dryer. The large bright sunlit rooms with high ceilings give this apartment a special touch. Rent includes heat, hot water and electricity. It has off street parking and a porch to sit and enjoy your morning coffee.

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    110 Estey St Unit 1, Brattleboro, VT 05301
  • /13

    $375,000

    Sold Dec 18, 2025

    62 Westminster Rd, Putney, VT 05346

    • 2,293 Sq Ft
    • Built 1850

    Last Sold Summary

    • $164/SF
    • 20 Days On Market

    Current Estimated Value $388,071

    Last Listing Agent Lily Gautot Greenwald Realty Group

    62 Westminster Rd, Putney, VT 05346
    • /40

      Est $582,303

      Not Listed For Sale

      27 Haymaker Ln Unit 9A, Wilmington, VT 05363

      • 3 Beds
      • 2.5 Baths
      • 2,500 Sq Ft
      • Built 1989
      27 Haymaker Ln Unit 9A, Wilmington, VT 05363

      Last Sold Summary

      • 18 Days On Market

  • /5

    $139,000

    $36K PRICE DROP
    • 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
  • /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
  • /26

    $40,000

    Sold Sep 17, 2025

    00 E Putney Falls Rd, Putney, VT 05346

    • Land
    • 1.5 Acres
    • $26,667 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 76 Days On Market

    Last Listing Agent Geralyn Donohue Four Seasons Sotheby's Int'l Realty

    00 E Putney Falls Rd, Putney, VT 05346
    • /21

      Est $134,847

      Not Listed For Sale

      724 Saxtons River Rd, Saxtons River, VT 05154

      724 Saxtons River Rd, Saxtons River, VT 05154

      Last Sold Summary

      • 207 Days On Market

Showing Results 81 - 120, Page 3 of 18

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