Windham County, VT Homes

/56
$350,000
- 6 Beds
- 4.5 Baths
- 3,042 Sq Ft
2072 N Main St, Londonderry, VT 05148

Rare Mixed-Use Opportunity in Downtown Londonderry, VT – Live, Work, or Invest! Unlock the full potential of this versatile and beautifully situated property in the heart of Londonderry’s vibrant downtown district. With major West River frontage, expansive lawn space, and prime visibility on North Main Street, this unique listing offers endless possibilities — perfect for residential, commercial,

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 441-6058

2072 N Main St, Londonderry, VT 05148
/11
$2,175 per month
- 4 Beds
- 1 Bath
- 1,360 Sq Ft
- House for Rent
123 Frost St, Brattleboro, VT 05301

A nice house that is suitable for up to 5 occupants and conveniently located within walking distance to the shopping, restaurants and entertainment in downtown Brattleboro. Spacious kitchen includes a dishwasher and built in microwave, recently purchased stove & fridge. This unit also featuring laundry hookups and a bathtub/shower combo. This home features a first floor bedroom or office space

123 Frost St, Brattleboro, VT 05301
/21
$270,000 Sold Sep 19, 2025
- 1,386 Sq Ft
- $195/SF
- 3 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1961
204 Bluebrook Rd, West Dover, VT 05356

This 3 bedroom cape style home sits on the Blue Brook of West Dover in a private stream setting. The owner has most recently entertained many Air bnb guests who all leave lovely comments about this special place. Skiing is just a few minutes from this home as are two golf courses, restaurants and shopping. Vast trails are just down the road and across the brook is the National Forest where

Regina Perrotto Skihome Realty

204 Bluebrook Rd, West Dover, VT 05356

/20
Est $578,028 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,036 Sq Ft
78 Middle Ridge Rd Unit 102, Stratton, VT 05155

78 Middle Ridge Rd Unit 102, Stratton, VT 05155

/10
$185,000
- Land
- 8 Acres
- $23,125 per Acre
4441 Vt Route 30, Jamaica, VT 05343

Discover the potential of this serene and wooded 8.0± acre parcel, offering a peaceful setting and natural beauty just minutes from the heart of Jamaica Village. Currently being subdivided from a larger tract, the lot features a 5 Bedroom Wastewater Permit pending state approval and a survey in progress to finalize boundaries—laying the foundation for your future plans. An existing electric

Trent Stephens

Wohler Realty Group

(802) 808-6056

4441 Vt Route 30, Jamaica, VT 05343
/12
$1,850 per month
- 3 Beds
- 1 Bath
- 1,700 Sq Ft
- Apartment for Rent
1155 Putney Rd Unit 1A, Brattleboro, VT 05301

Newly renovated second floor apt above local Restaurant. Conveniently located on the roundabout at Exit 3 of I-91. Great apartment with all new appliances, countertops, flooring, upgraded electrical and more. Easy location near shopping and restaurants. Non smokers and no pets. All utilities by tenant.

Jim Bialowski BHG Masiello Keene

1155 Putney Rd Unit 1A, Brattleboro, VT 05301
/40
$781,000 Sold Sep 19, 2025
- 2,663 Sq Ft
- $293/SF
- 33 Days On Market
- 3 Beds
- 5 Baths
- Built 1944
1194 Ames Hill Rd, Brattleboro, VT 05301

Welcome to The Appleshed. Starting as a storage structure within an old apple orchard, to a gentleman's hunting/fishing camp, to the cherished family home it is today, this property has had many lives and grown into a beloved gathering place for generations. Now it’s ready for its next chapter. Set on 63.8 acres with a babbling brook and breathtaking views of Mount Monadnock, this is a true

Keith Nowak Four Seasons Sotheby's Int'l Realty

1194 Ames Hill Rd, Brattleboro, VT 05301

/11
Est $315,181 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,992 Sq Ft
48 Loop Rd, Newfane, VT 05345

48 Loop Rd, Newfane, VT 05345

/14
$120,000
- Land
- 2.07 Acres
- $57,971 per Acre
191 Pingree Park Ln, Londonderry, VT 05148

Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

Alison Cummings

Cummings & Co

(802) 848-6904

191 Pingree Park Ln, Londonderry, VT 05148
/20
$13,466 per month
- 3 Beds
- 3 Baths
- 1,194 Sq Ft
- Condo for Rent
3A Black Pine Unit ID1261564P, Dover, VT 05356

This gorgeous three-bedroom condo is situated directly across from Mount Snow, offering everything you need for the perfect getaway. Whether you're planning a ski trip in the winter, an action-packed summer vacation, or a relaxing fall leaf-peeping trip, this is a great spot to call your home away from home. Wake up in the morning and take in the beautiful views of Mount Snow from your windows;

3A Black Pine Unit ID1261564P, Dover, VT 05356
/28
$363,000 Sold Sep 19, 2025
- 1,584 Sq Ft
- $229/SF
- 11 Days On Market
- 3 Beds
- 2 Baths
- Built 1970
34 Mountain View Loop, Dover, VT 05356

This classic chalet located just 1.5 miles from Mount Snow Resort exudes charm and great potential. Set on a .45-acre lot, this solid 3-bedroom home has a new metal shingle life-time roof (2021), replacement windows (2020) and the chimney was sealed in 2021 as well. This home offers a great foundation for your finishing touches. Step inside to an open-concept living area featuring wide-plank pine

Patrice Schneider Southern Vermont Realty Group

34 Mountain View Loop, Dover, VT 05356

/33
Est $607,785 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 1,800 Sq Ft
40 Kingswood Rd, Dover, VT 05356

40 Kingswood Rd, Dover, VT 05356

/18
$130,000
- Land
- 2.19 Acres
- $59,361 per Acre
192 Pingree Park Ln, Londonderry, VT 05148

Discover this hidden gem in Londonderry. River frontage on pristine Utley Brook with headwaters flowing from the Green Mountain National Forest create a serene setting minutes from downtown. Full time residence or vacation home, you choose! Ready to build. Completely engineered- State and Town permits for a 4 bedroom home in place including septic permits, well and house placement, updated

Alison Cummings

Cummings & Co

(802) 444-8158

192 Pingree Park Ln, Londonderry, VT 05148
/7
$1,700 per month
- 2 Beds
- 1 Bath
- 671 Sq Ft
- Apartment for Rent
1889 Vermont 30 Unit 2, Townshend, VT 05353

Second Floor 2 bedroom apartment with natural light, close to town and is available now. Off street parking and a yard make the location ideal.

Peggy Winchester ACORN REAL ESTATE GROUP LLC

1889 Vermont 30 Unit 2, Townshend, VT 05353
/36
$470,000 Sold Sep 19, 2025
- 2,432 Sq Ft
- $193/SF
- 31 Days On Market
- 3 Beds
- 2 Baths
- Built 1982
52 Big Bend Loop, Wilmington, VT 05363

This well-maintained 3 bedroom, 2 bath chalet in the sought after Chimney Hill community offers three levels of thoughtfully designed living space, providing plenty of room for the entire family. Recent improvements include a new roof in 2024, freshly painted exterior, and a recently stained deck, ensuring the home is move-in ready. The open concept main floor features an updated kitchen with

Prema Fitzpatrick Skihome Realty

52 Big Bend Loop, Wilmington, VT 05363

/33
Est $251,301 Not Listed For Sale
- 1 Bed
- 1 Bath
- 856 Sq Ft
849 Mcmillan Rd, Halifax, VT 05342

849 Mcmillan Rd, Halifax, VT 05342

/37
$395,000 Under Contract
- 4 Beds
- 2 Baths
- 2,400 Sq Ft
3298 Houghtonville Rd, Grafton, VT 05146

Classic 1800s Farmhouse in Charming Grafton, VermontLocated in Houghtonville, a beautiful part of historic Grafton, this mid-19th century farmhouse offers a rare opportunity to restore and reimagine a true Vermont original. With strong bones and timeless character, the home features wide plank floors, vintage woodwork, and a traditional layout that reflects its heritage. Typical of this

Alison Cummings

Cummings & Co

(802) 317-7411

3298 Houghtonville Rd, Grafton, VT 05146
/4
$1,600 per month
- 2 Beds
- 1 Bath
- 640 Sq Ft
- Condo for Rent
498 Marlboro Rd Unit N37, Brattleboro, VT 05301

Property Id: 1510783Two bedroom apartment for rent in a professionally managed apartment building in West Brattleboro, Vermont. Clean, bright, with on-site laundry and off-street parking. Rents include heat and hot water. All units are non smoking. Small pets would require approval and an additional security deposit.

498 Marlboro Rd Unit N37, Brattleboro, VT 05301
/15
$55,000 Sold Sep 19, 2025
- 2,090 Sq Ft
- $26/SF
- 432 Days On Market
- Built 1860
211 High St, Brattleboro, VT 05301

Here's a great opportunity! Formerly a 2 unit multi-family, this is currently a shell ready for your finishing! This property will need everything ... heating, electrical, plumbing, exterior work and full interior finishing. Very convenient to downtown, some off street parking but nicely sited above the road. Please do NOT park in the driveway.

A.J. Bellville Bellville Realty

211 High St, Brattleboro, VT 05301

/8
Est $793,790 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,244 Sq Ft
438 River Rd, Guilford, VT 05301

438 River Rd, Guilford, VT 05301

/16
$235,000
- Land
- 4.26 Acres
- $55,164 per Acre
190 &192 Pingree Park Ln, Londonderry, VT 05148

Quiet and pristine, this 4 + acre parcel is a prime location for your new home. At the end of a private road and within an easy distance to the grocery store, this is truly the best of both worlds. With babbling Utley Brook as the boundary on the East side, across the river is protected by a conservation district, insuring riverfront privacy. This nicely wooded parcel already has a road into the

Alison Cummings

Cummings & Co

(802) 523-3683

190 &192 Pingree Park Ln, Londonderry, VT 05148
/22
$15,000 per month
- 2 Beds
- 2 Baths
- 1,196 Sq Ft
- House for Rent
242 Cross Rd, Londonderry, VT 05155

Picture perfect 2 bedroom 2 bath 2025/2026 Seasonal rental! Recently completed construction, bright open living space, hardwood floors, cozy woodstove in a private location only 15 minutes to Stratton Resort, 15 minutes to Bromley, and 6 minutes to Magic Mountain ski area! Less than 10 minute drive to Londonderry for shopping and dining.

Lauren Behm Berkshire Hathaway HomeServices Stratton Home

242 Cross Rd, Londonderry, VT 05155
/56
$475,000 Sold Sep 18, 2025
- 2,160 Sq Ft
- $220/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 1970
6900 Windham Hill Rd, Windham, VT 05359

Nestled in the rolling hills of Windham, this inviting home offers the perfect blend of comfort and charm. Step inside the large mudroom as you transition inside to find tastefully painted rooms that create a warm and welcoming atmosphere. The fireplace features updated stonework, making it a stunning focal point for cozy evenings. A completely rebuilt deck extends your living space outdoors,

Keith Nowak Four Seasons Sotheby's Int'l Realty

6900 Windham Hill Rd, Windham, VT 05359

/24
Est $214,859 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,120 Sq Ft
1751 Rockingham Rd, Rockingham, VT 05143

1751 Rockingham Rd, Rockingham, VT 05143

/22
$1,000,000
- Land
- 67 Acres
- $14,925 per Acre
00 S Pine Banks Rd, Putney, VT 05346

Unleash the potential of this exceptional 60+ acre Vermont property, a rare offering brimming with diverse landscapes and endless possibilities. A well-maintained gravel driveway leads you into the heart of the land, complete with readily available power. Discover multiple potential building sites, each offering breathtaking views or secluded privacy, tailored to your preference. A charming

Ross Doody

Century 21 Highview Realty

(802) 499-2391

00 S Pine Banks Rd, Putney, VT 05346
/3
$2,200 per month
- 3 Beds
- 1 Bath
- 1,500 Sq Ft
- Condo for Rent
205 West St Unit A, Dummerston, VT 05301

Property Id: 2098688Welcome to your peaceful retreat in the heart of West Dummerston! This charming 3-bedroom + office, 1-bath converted barn apartment offers rustic warmth, privacy, and a welcoming sense of community, all just 10 minutes from Downtown Brattleboro and a 1-minute drive from the iconic covered bridge swimming hole.Inside, you'll find a cozy living room with a

205 West St Unit A, Dummerston, VT 05301
/50
$739,000 Sold Sep 18, 2025
- 3,050 Sq Ft
- $242/SF
- 6 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1990
52 Spruce Lake Estates, Wilmington, VT 05363

25 private acres with lake frontage, stunning lake & mountain scenery, and a beautifully maintained 3,300+ sq ft home w/ direct-entry 2-car garage. Located in private Spruce Lake Estates—close proximity to Mount Snow & Hermitage Club, State Parks, restaurants, shops and public transportation—this rare property offers 4-season living w/ space, privacy & frontage on a non-motorized lake w/ beach,

Jacki Murano Southern Vermont Realty Group

52 Spruce Lake Estates, Wilmington, VT 05363

/14
Not Listed For Sale
5 Lahar Rd, Marlboro, VT 05351

5 Lahar Rd, Marlboro, VT 05351

/30
$125,000
- 1,968 Sq Ft
10 Taylor St, Town of Rockingham, VT 05101

INVESTER SPECIAL! This 2-unit property has separate utilities, 2-3 bedroom units on each floor depending on how the layout is set up. Rooms are generously sized, front and side porches for each unit, full basement and attic.This would make a nice generational or family home or a great starter home with rental potential.

Julie Buffum

Buffum Realty

(802) 347-9139

10 Taylor St, Town of Rockingham, VT 05101
/10
$1,650 per month
- 1 Bed
- 1 Bath
- 422 Sq Ft
- Apartment for Rent
114 Main St Unit 33, Brattleboro, VT 05301

Newly renovated third floor one bedroom apartment with a large window with in-town views. Access to everything you need within a fewblocks. 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 33, Brattleboro, VT 05301
/12
$13,000 Sold Sep 18, 2025
- Land
- 0.47 Acre
- $27,660 per Acre
- 22 Days On Market
0 Elwell Heights Dr, Wilmington, VT 05363

.47 acre wooded parcel located just across the road from the Castle Hill picnic and boat launch area on Harriman Reservoir in Wilmington. Enjoy water skiing, boating, canoeing, kayaking, fishing and swimming just steps away. This is the perfect spot for a garage or shed to store the boats or an off grid cabin. There is no soil testing so new owners would need to perform tests in order to

Chad Lackey Deerfield Valley Real Estate

0 Elwell Heights Dr, Wilmington, VT 05363

/36
Est $510,636 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,050 Sq Ft
208 Shady Ln, West Wardsboro, VT 05360

208 Shady Ln, West Wardsboro, VT 05360

/60
$599,000
- 3 Beds
- 2 Baths
- 3,000 Sq Ft
121 Dover Hill Rd, Dover, VT 05341

Highly motivated sellers. Ideal for remote workers or second-home buyers, this Vermont retreat offers fiber-optic internet, energy-efficient systems, no water or sewer bills, and some of the state's lowest property taxes. Set on 5 private acres just minutes from Mount Snow and Grout Pond, this move-in ready home supports low-cost living with high quality of life.The updated kitchen

Nick Sicard EXP Realty

121 Dover Hill Rd, Dover, VT 05341
/2
$1,500 per month
- 1 Bed
- 1 Bath
- Condo for Rent
376 Western Ave Unit 1, Brattleboro, VT 05301

Property Id: 2099462Completely renovated spacious and bright first floor apartment. Large deck. Wood stove with free wood. New Mitsubishi mini split. Close to town park, hiking trails, farmers market. Close to downtown. Off street parking and storage area.

376 Western Ave Unit 1, Brattleboro, VT 05301
/26
$40,000 Sold Sep 17, 2025
- Land
- 1.5 Acres
- $26,667 per Acre
- 76 Days On Market
00 E Putney Falls Rd, Putney, VT 05346

1.5 acre +/- corner lot along East Putney Falls Road and Bellows Falls Road (Route 5) with State WW permit in progress for a 3-bedroom home. Driveway access to potential building site off East Putney Falls Road. Level, wooded building area elevated from road. Power at road and adjacent to property. Close to Putney Diner, The General Store, Putney Coop and Landmark College.

Geralyn Donohue Engel & Völkers Okemo

00 E Putney Falls Rd, Putney, VT 05346

/17
Est $479,735 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,309 Sq Ft
38 Summit Meadows Cir, Dover, VT 05356

38 Summit Meadows Cir, Dover, VT 05356

/41
$8,950,000
- 6 Beds
- 10 Baths
- 13,393 Sq Ft
370 Fischer Ln, Jamaica, VT 05343

Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

Dia Jenks LandVest, Inc/Woodstock

370 Fischer Ln, Jamaica, VT 05343
/7
$1,800 per month
- 1 Bed
- 1 Bath
- 535 Sq Ft
- Apartment for Rent
215 Main St Unit 209, Brattleboro, VT 05301

Recently renovated One bedroom apartment on the second floor. This one-bedroom apartment has bright sun lit rooms, with additional locking storage in the building, along with an elevator to get to the second floor for the onsite laundry facilities. This is intown living at its best. Apartment is partially furnished, just needs a bed.

Peggy Winchester ACORN REAL ESTATE GROUP LLC

215 Main St Unit 209, Brattleboro, VT 05301
/23
$490,000 Sold Sep 15, 2025
- 2,400 Sq Ft
- $204/SF
- 405 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1800
494 Cobb Reed Rd, Wardsboro, VT 05355

This home offers the best of a country property. The 1800's cape provides many surprisingly large rooms for family gatherings or entertaining friends. The old character of the home is evident in the wide pine floors, old fireplaces and 12 over 12 windows. With 2 bedrooms and two full baths with soaker tubs on each floor this should meet everyone's needs. There is also an exercise room in the

David Brown Berkley & Veller Greenwood Country

494 Cobb Reed Rd, Wardsboro, VT 05355

/30
Est $646,673 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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