Windham County, VT Homes

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  $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
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  /12

  $1,000 per month

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

  3550 Coolidge Hwy, Guilford, VT 05301

  Property Id: 1565026THIS IS A SHARED SPACE - FEMALE ROOMMATE WANTEDSpacious 1-bedroom shared property located at 3550 Coolidge Highway in Guilford, VT. Built in 1979, this cozy unit comes with modern amenities including a refrigerator, washer, dryer, and more. Enjoy the convenience of off-street parking, on-site laundry, and a fireplace. Utilities included in the rent are

  3550 Coolidge Hwy, Guilford, VT 05301
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  /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 $360,297

  Last Listing Agent Rich Caplan Deerfield Valley Real Estate

  45 Dorr Fitch Rd, West Dover, VT 05356
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  /30

  Est $644,280 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  79 Wilmington Heights, Wilmington, VT 05363

  79 Wilmington Heights, Wilmington, VT 05363
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  /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
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  /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 $425-$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
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  /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
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  /30

  Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 2,088 Sq Ft

  30 Styles Branch Rd Unit 309, Stratton, VT 05360

  30 Styles Branch Rd Unit 309, Stratton, VT 05360
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  /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
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  /19

  $850 per month

  • Studio
  • 1 Bath
  • 200 Sq Ft
  • Condo for Rent

  111 Wiswall Hill Rd Unit Tiny home/mini cottage, Newfane, VT 05345

  Initial lease term will be months to months to ensure both sides are happy with the living situation as the cottage is in close proximity to our main home.utilities can be agreed on with a flat fee of aprox $150.-/monthdriveway will be snow cleared by the owner. walkway to the unit and stairs are the responsibility of the tenant. parking is available.

  111 Wiswall Hill Rd Unit Tiny home/mini cottage, Newfane, VT 05345
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  /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

  Last Listing Agent Kim Meeker Southern Vermont Realty Group

  28 Dover Green Rd, Dover, VT 05356
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  /26

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 962 Sq Ft

  1 Wildwood Dr, West Brattleboro, VT 05301

  1 Wildwood Dr, West Brattleboro, VT 05301
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  /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
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  /29

  $18,000 per month

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • House for Rent

  67 Vermont Route 100, Jamaica, VT 05155

  Discover the charm of this delightful rental nestled along a quintessential river in Vermont! With its prime location on a major road, you're just 7 miles away from the slopes of the Stratton Mountain ski resort, making it the perfect getaway for winter sports enthusiasts. This spacious home boasts multiple living areas, ensuring everyone has their own space to relax and unwind. With four

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  67 Vermont Route 100, Jamaica, VT 05155
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  /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 $560,972

  Last Listing Agent Sigrid Pickering Chimney Hill Realty

  78 Pond Loop Unit M-2, Wilmington, VT 05363
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  /32

  Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,529 Sq Ft

  97 Stratton Dr, Townshend, VT 05353

  97 Stratton Dr, Townshend, VT 05353
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  /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
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  /30

  $1,400 per month

  • 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
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  /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
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  /21

  Est $341,395 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  443 Dover Rd, Newfane, VT 05351

  443 Dover Rd, Newfane, VT 05351
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  /20

  $339,000

  • 3 Beds
  • 2.5 Baths
  • 1,510 Sq Ft

  6 Longest Dr Unit 1, Wilmington, VT 05363

  Turn key renovated 3+ bedroom, 2.5 bath townhouse just off the Haystack Golf Club 10th hole, with easy access to trails, the village of Wilmington, lakes, and the nearby Hermitage Club and Mount Snow ski resorts. This unit has been completely renovated throughout and is being sold for immediate enjoyment. Features include a vaulted living room area with stone fireplace, great natural light

  Adam Palmiter Berkley & Veller Greenwood/Dover

  6 Longest Dr Unit 1, Wilmington, VT 05363
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  /23

  $5,000 per month

  • 3 Beds
  • 1.5 Baths
  • 2,092 Sq Ft
  • House for Rent

  1070 Hells Peak Rd, Londonderry, VT 05148

  Charming Antique Home on 60 Acres – Hell’s Peak Road, Londonderry, Vermont Set on 60 rolling acres in the quaint hamlet of Londonderry, this beautiful antique home offers the perfect Vermont retreat. With availability for the upcoming 2025–26 ski season, it’s an ideal opportunity for those seeking both seasonal enjoyment and year-round serenity. Located near three premier ski areas with a direct

  Bob Maisey Berkshire Hathaway HomeServices Stratton Home

  1070 Hells Peak Rd, Londonderry, VT 05148
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  /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
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  /35

  Est $592,390 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 2,517 Sq Ft

  10 Lower Highlands Rd, Dover, VT 05356

  10 Lower Highlands Rd, Dover, VT 05356
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  /17

  $209,000 Under Contract

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  75 Mather Rd, Brattleboro, VT 05301

  Great Location, Great opportunity! Currently, a 1-bedroom, 1-bath home sits back on a desirable, pleasant country road. It is a larger lot than most, and with vision, here is an opportunity to start home ownership, downsize to a one-level with efficient living space. Use an investment or create your small Vermont getaway. This sweet spot is ready for your vision and ideas. This property is in

  Kristen Ziter Taylor Brattleboro Area Realty

  75 Mather Rd, Brattleboro, VT 05301
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  $2,000 per month

  • 3 Beds
  • 1 Bath
  • 2,200 Sq Ft
  • Condo for Rent

  197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301

  Available December 1Spacious and sun-filled 3-bedroom apartment with an additional office, offering room to live, work, and relax. Enjoy a full dining room, large kitchen, comfortable living room, and your own private porch—perfect for morning coffee or unwinding at the end of the day.This home features new windows, clean carpeting, and excellent natural light from every direction. You’ll

  197 Western Ave Unit 2 - Upstairs, Brattleboro, VT 05301
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  /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 $600,595

  Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

  31 Joan's Ridge Rd, West Dover, VT 05356
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  /19

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft

  43 High Point Dr Unit D23, Stratton, VT 05360

  43 High Point Dr Unit D23, Stratton, VT 05360
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  /27

  $249,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,155 Sq Ft

  4668 Vermont 112, Halifax, VT 05342

  Historic hillside farm situated along the North River valley just a few miles into VT from MA on 31 acres of land. Approx. 5 acres of open sloping pasture most recently used as a sheep farm. The house is circa 1860 and has good bones and updated systems including a new drilled well, on demand HW, propane backup generator and other modern improvements. The interior of the home is in need of

  Chris Long BHG Masiello Brattleboro

  4668 Vermont 112, Halifax, VT 05342
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  /33

  $6,000 per month

  • 5 Beds
  • 3 Baths
  • 2,912 Sq Ft
  • House for Rent

  1138 River Rd, Jamaica, VT 05343

  WINTER MONTHLY RENTAL - $6,000/Month Plus prepaid utilities ($750/month) | Total due in Full Before Occupancy. Spend the winter in the mountains with this spacious and fully updated 5-bedroom, 3-bath home with a cozy loft in scenic Jamaica, VT. Nestled in a quiet wooded setting, this inviting retreat comfortably accommodates up to 12 guests. After a day on the slopes, relax by the fireplace with

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1138 River Rd, Jamaica, VT 05343
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  /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 $216,129

  Last Listing Agent Glenn Olney Barrett and Valley Associates Inc.

  1457 Rockingham Rd, Town of Rockingham, VT 05101
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  /40

  Est $564,333 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft

  2900 Route 121 E, Grafton, VT 05146

  2900 Route 121 E, Grafton, VT 05146
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  /44

  $429,900

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  1909 Davidson Hill Rd, Westminster, VT 05158

  This charming Vermont country farmhouse offers peaceful privacy at the end of a quiet town road. Recently updated with quality materials and meticulous attention to detail, the home blends classic warmth with modern comfort. The open-concept main floor features a beautifully appointed kitchen ideal for family meals, flowing into the dining area and a cozy living room with a bay window and

  Steve Schoppmeyer BHG Masiello Brattleboro

  1909 Davidson Hill Rd, Westminster, VT 05158
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  /41

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  92 Prospect St Unit 1, Brattleboro, VT 05301

  Available Now - First Floor apartment in duplex close to downtown Brattleboro. 2 bedroom, beautiful wood floors, Covered porch, pantry, non-working fireplace, 2 Off street assigned parking spaces.Snow Removal, Garbage and Water Included. Tenants pay all utilities and oil. $1500/month - First and security deposit required.Email for Info or Application. Credit and Background checks

  92 Prospect St Unit 1, Brattleboro, VT 05301
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  /32

  $500,000 Sold Mar 17, 2025

  659 Magic Cir, Londonderry, VT 05148

  • 5 Beds
  • 3 Baths
  • 2,962 Sq Ft
  • Built 1972

  Last Sold Summary

  • 17% Below List Price
  • $169/SF
  • 182 Days On Market

  Current Estimated Value $526,433

  Last Listing Agent Ernie Rossi 802 Real Estate

  659 Magic Cir, Londonderry, VT 05148
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  /34

  Est $854,067 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,412 Sq Ft

  5 Rice Hill Rd, Dover, VT 05341

  5 Rice Hill Rd, Dover, VT 05341
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  /36

  $449,000 Under Contract

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

  44 Villager Loop, Dover, VT 05356

  Mountain Retreat located at 44 Villager Loop, Dover Hills, Dover, VTVery little use and never rented. Upgrades include a freshly painted exterior with a new roof and 3 mini-splits. Large mudroom entry, living room with fireplace, kitchen, dining area, 3 bedrooms, 3 baths, family room and a large deck for entertaining and relaxing. Close to the town center, restaurants, Town Park and Valley

  Janet Boyd Boyd Real Estate

  44 Villager Loop, Dover, VT 05356
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  /24

  $40,000 per month

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

  1303 Goodaleville Rd, South Londonderry, VT 05155

  Stunning expansive farmhouse ready for your winter enjoyment. Just ten minutes from Stratton's access road entrance . Located on a beautiful country road. 5 attractive bedrooms , 3 full baths, 2 half baths. Yoga room. Sauna. Wood burning fireplace. Garage. This decorator appointed home is the perfect winter vacation respite for you and your family and friends. Utilities , Owners's

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  1303 Goodaleville Rd, South Londonderry, VT 05155
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  /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 $708,858

  Last Listing Agent Margretta Fischer Wohler Realty Group

  40 Founders Hill Rd, Stratton, VT 05360
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  Est $207,650 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,369 Sq Ft

  951 Dover Rd, South Newfane, VT 05351

  951 Dover Rd, South Newfane, VT 05351

Showing Results 41 - 80, Page 2 of 18