Windham County, VT Homes

/32
$475,000

$75K 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
/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 $473,146

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

214 Putney Rd, Brattleboro, VT 05301

/17
Est $310,384

Not Listed For Sale

5 Mountain Village, Dover, VT 05356
- 2 Beds
- 2 Baths
- 924 Sq Ft
- Built 1987
5 Mountain Village, Dover, VT 05356

Last Sold Summary
- 77 Days On Market

/2
$45,000

Under Contract
- Land
- 1 Acre
- $45,000 per Acre
0 Edie Ln, Jamaica, VT 05343

This is a town sale property. There is a 30 day waiting period after a fully executed contract. The 30 days is a window for public feedback. Under the statute, if Town residence object to the sale, they have 30 days from the date of the notice to submit a petition to the Town. If a petition is signed by at least 5% of the towns registered voters, the select, Board cannot just sell the property,

Carrie Mathews Winhall Real Estate

0 Edie Ln, Jamaica, VT 05343
/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

/25
Not Listed For Sale

1879 Fort Bridgman Rd, Vernon, VT 05354
- 2 Beds
- 2 Baths
- 1,440 Sq Ft
- Built 2022
1879 Fort Bridgman Rd, Vernon, VT 05354

Last Sold Summary
- 39 Days On Market

/50
$565,000
- 3 Beds
- 2 Baths
- 1,814 Sq Ft
1886 Winhall Hollow Rd, South Londonderry, VT 05155

Great Location, New Roof, New Septic, recent exterior painting! This turn key residence is ideally located between three ski areas and near schools and shopping. Gourmet kitchen, wood floors, upscale baths and a huge 3 car garage/ barn with finished office space. Tucked amidst the forest with views of Magic Mountain's ridge line, whether you are looking for a second home in the mountains or

Kim Morgan-Wohler Wohler Realty Group

1886 Winhall Hollow Rd, South Londonderry, VT 05155
/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 $588,544

Last Listing Agent Jennifer Hovey-Densmore Deerfield Valley Real Estate

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

/51
Est $1,423,135

Not Listed For Sale

115 E Village Cir, Wilmington, VT 05363
- 4 Beds
- 3.5 Baths
- 3,203 Sq Ft
- Built 2016
115 E Village Cir, Wilmington, VT 05363

Last Sold Summary
- 134 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
/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 $740,637

Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home

573 Middletown Rd, Londonderry, VT 05148

/36
Est $440,026

Not Listed For Sale

17 Old Town Rd, West Dover, VT 05356
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
- Built 2006
17 Old Town Rd, West Dover, VT 05356

Last Sold Summary
- 102 Days On Market

/23
$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
/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

/27
Est $440,979

Not Listed For Sale

2193 Old County Rd, West Halifax, VT 05358
- 3 Beds
- 1.5 Baths
- 1,883 Sq Ft
- Built 2003
2193 Old County Rd, West Halifax, VT 05358

Last Sold Summary
- 27 Days On Market

/31
$289,000
- 2 Beds
- 1 Bath
- 808 Sq Ft
57 Eddy Rd, Newfane, VT 05345

Tucked away near the end of a quiet gravel road, this charming two-bedroom cottage offers exceptional privacy on 39 wooded acres in Newfane. Surrounded by nature, the secluded property provides abundant space for exploring, hiking, hunting, recreation, or simply enjoying the peaceful Vermont setting. A stream winds through the land, adding to the property’s natural appeal. Inside, the cozy home

Grayson VanHendrick Flex Realty

57 Eddy Rd, Newfane, VT 05345
/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 $398,847

Last Listing Agent Lily Gautot Greenwald Realty Group

62 Westminster Rd, Putney, VT 05346

/23
Not Listed For Sale

8 Deepwood Park, Brattleboro, VT 05301
- 3 Beds
- 2 Baths
- 880 Sq Ft
- Built 2024
8 Deepwood Park, Brattleboro, VT 05301

Last Sold Summary
- 118 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
/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

/35
Est $509,417

Not Listed For Sale

4 Summit Meadows Ln, Dover, VT 05356
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
- Built 1982
4 Summit Meadows Ln, Dover, VT 05356

Last Sold Summary
- 139 Days On Market

/2
$89,900
- 4 Beds
- 2 Baths
- 1,902 Sq Ft
206 Smith Rd, Jamaica, VT 05343

Looking for a project? Featuring a drilled well, existing septic, electric, and driveway, you have a good start for a new build, renovation or a combination of the two. The cabin has been added onto many times, making room for a growing family. The land is mostly level, with some nice plantings and the house sits back a little distance from the neighbors. The well is being shared, electric is run

Christine Lewis Brattleboro Area Realty

206 Smith Rd, Jamaica, VT 05343
/50
$300,000

Sold Mar 16, 2026

756 Turkey Mountain Rd, Jamaica, VT 05343
- 3 Beds
- 2 Baths
- 1,468 Sq Ft
- Built 1996
Last Sold Summary
- 6% Below List Price
- $204/SF
- 19 Days On Market
Current Estimated Value $310,058

Last Listing Agent Jacki Murano Southern Vermont Realty Group

756 Turkey Mountain Rd, Jamaica, VT 05343

/13
Not Listed For Sale

#10 Wilmington Heights Spur, Wilmington, VT 05363
#10 Wilmington Heights Spur, Wilmington, VT 05363

Last Sold Summary
- 135 Days On Market

/8
$95,000

$25K PRICE DROP
- Land
- 15 Acres
- $6,333 per Acre
0 Carpenter Hill Rd Unit 5090787, Guilford, VT 05301

Hillside building lot deeded for one beautiful home, with a straight-ahead view of inspiring mountains and valleys to the south. The property is moderately sloped near the road but more flat at the highest elevation, with benches of level ground at intervals up and down the land. A network of hiking trails is blazed across the property, but the easiest way to view the high ground is what remains

David White OwnerEntry.com

0 Carpenter Hill Rd Unit 5090787, Guilford, VT 05301
/2
$305,000

Sold Oct 06, 2025

152 Main St, Grafton, VT 05146
- 3 Beds
- 2 Baths
- 1,917 Sq Ft
- Built 1841
Last Sold Summary
- 22% Below List Price
- $159/SF
- 89 Days On Market
Current Estimated Value $548,227

Last Listing Agent Jessica Landers Barrett and Valley Associates Inc.

152 Main St, Grafton, VT 05146

/38
Est $629,841

Not Listed For Sale

10 E Village Cir, Wilmington, VT 05363
- 6 Beds
- 3 Baths
- 2,312 Sq Ft
- Built 1970
10 E Village Cir, Wilmington, VT 05363

Last Sold Summary
- 95 Days On Market

/8
$70,000
- Land
- 2.01 Acres
- $34,826 per Acre
0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354

Amazing Opportunity to Build Your Forever Home!This beautiful south-facing, open lot offers the perfect setting for your dream home, with convenient access to power right at the road. The back portion of the property is graced with mature trees, providing shade and a natural pathway to nearby VAST snowmobile and hiking trails. Enjoy the peace of a quiet country setting where you can listen to

Kerry Mulverhill

0 Huckle Hill Rd Unit 5059719, Vernon, VT 05354
/35
$391,000

Sold Jun 25, 2026

76 Belmont Ave, Brattleboro, VT 05301
- 3 Beds
- 2 Baths
- 1,686 Sq Ft
- Built 1915
Last Sold Summary
- 9% Above List Price
- $232/SF
- 4 Days On Market
Current Estimated Value $356,342

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

76 Belmont Ave, Brattleboro, VT 05301

/41
Est $536,517

Not Listed For Sale

441 Guilford St, Brattleboro, VT 05301
- 4 Beds
- 2 Baths
- 2,450 Sq Ft
- Built 1880
441 Guilford St, Brattleboro, VT 05301

Last Sold Summary
- 48 Days On Market

/10
$499,900
- Land
- 8.5 Acres
- $58,812 per Acre
340 Tyanoga Lot X, Whitingham, VT 05361

WATERFRONT! WATERFRONT! WATERFRONT! Nestled at the end of a quiet cul-de-sac, this private property offers water front land; the perfect setting to build your dream home, for full-time living or a second home for quiet enjoyment. Much of the groundwork has already been completed, making it easy to bring your vision to life. This property features: drilled well already in place; underground

Pauline Green Lamacchia Realty, Inc. - Adams

340 Tyanoga Lot X, Whitingham, VT 05361
/56
$538,000

Sold Jul 21, 2026

1041 Church Hollow Rd, Brattleboro, VT 05301
- 4 Beds
- 2.5 Baths
- 2,567 Sq Ft
- Built 1987
Last Sold Summary
- $210/SF
- 2 Days On Market
Current Estimated Value $560,545

Last Listing Agent Kathy Dowd Bellville Realty

1041 Church Hollow Rd, Brattleboro, VT 05301

/23
Est $170,947

Not Listed For Sale

233 Bluebrook Rd, Dover, VT 05356
- 6 Beds
- 4 Baths
- 2,764 Sq Ft
- Built 1974
233 Bluebrook Rd, Dover, VT 05356

Last Sold Summary
- 32 Days On Market

/31
$1,050,000
- 5 Beds
- 4 Baths
- 3,300 Sq Ft
1C Ego Aly, Dover, VT 05356

Breathtaking, direct Mount Snow views from this spectacular Outlook Townhome, perched just above the base area at Mount Snow Ski Resort. With rustic natural wood finishes, soaring vaulted spaces, and sweeping slopeside exposure, this five-bedroom, four-bath townhome strikes a rare balance of warmth and luxury. A timber-framed covered porch wraps around to the rear, opening up to west and

Adam Palmiter Berkley & Veller Greenwood/Dover

1C Ego Aly, Dover, VT 05356
/60
$570,000

Sold Jul 31, 2025

290 Roel Rd, Brattleboro, VT 05301
- 2 Beds
- 2.5 Baths
- 2,599 Sq Ft
- Built 1991
Last Sold Summary
- 5% Below List Price
- $219/SF
- 79 Days On Market
Current Estimated Value $564,437

Last Listing Agent Flex Realty Group Flex Realty

290 Roel Rd, Brattleboro, VT 05301

/39
Est $538,539

Not Listed For Sale

60 Robbins Rd, Dover, VT 05341
- 3 Beds
- 2 Baths
- 2,252 Sq Ft
- Built 1995
60 Robbins Rd, Dover, VT 05341

Last Sold Summary
- 126 Days On Market

/20
$325,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
8F Dover Green Loop Unit 8F, Dover, VT 05356

Spacious townhome at an incredible price in the Dover Green community located just a short drive or shuttle ride south of Mount Snow. This private end unit sits nestled towards the top of the development with great privacy and parking, and has had numerous recent upgrades to the roof, foundation, paint, siding, and whole house water filtration. The interior boasts a vaulted great room, wood

Adam Palmiter Berkley & Veller Greenwood/Dover

8F Dover Green Loop Unit 8F, Dover, VT 05356
/40
$781,000

Sold Sep 19, 2025

1194 Ames Hill Rd, Brattleboro, VT 05301
- 3 Beds
- 5 Baths
- 2,663 Sq Ft
- Built 1944
Last Sold Summary
- 2% Below List Price
- $293/SF
- 33 Days On Market
Last Listing Agent Keith Nowak Four Seasons Sotheby's Int'l Realty

1194 Ames Hill Rd, Brattleboro, VT 05301

/40
Est $507,355

Not Listed For Sale

35 Buckboard Dr, Dover, VT 05356
- 3 Beds
- 2 Baths
- 1,372 Sq Ft
- Built 1987
35 Buckboard Dr, Dover, VT 05356

Last Sold Summary
- 44 Days On Market

/26
$299,000
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
57 Vartland Ridge, Londonderry, VT 05148

Set on 1.1 acres with access to VAST trails, this property offers a blend of recent upgrades, functional space, and future potential. Being sold as-is, the property offers the chance to update and customize while benefiting from several major upgrades already completed. Recent improvements include a new furnace and hot water heater installed in 2022, along with a new propane tank and updated

Jamie Wylie Stratton Real Estate

57 Vartland Ridge, Londonderry, VT 05148

Showing Results 81 - 120, Page 3 of 18

Vermont

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Windham County, VT Homes

Real Estate & Homes