Vintage homes for sale & real estate in Windham County, VT

77 homes

Sort:

Recommended

NEW 1 HR AGO

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
Large farmhouse with 15.78 acres, metal roof, easy access to multiple ski resorts. Four bedrooms, one and a half baths. Large front and back yard, level with some fencing. Will need notice to show.

$625,000

4 beds1.5 baths2,764 sq ft

768 VT Route 30, Jamaica, VT 05343

Metal roof • 15.78 acre lot • Built 1860

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
Come home to this cozy sun filled house with beautiful hardwood floors and a well thought out floor plan. Built ins, bookshelves and a fireplace are sure to please the next owner! This house is tucked away on a quiet street but also so close the town recreation area. Generous and private backyard with plenty of garden space available.

$250,000

3 beds1.5 baths1,232 sq ft

19 Williams Ter, Bellows Falls, VT 05101

Bookshelves • Private backyard • Built ins

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
Discover the ideal balance of privacy and convenience in this welcoming 4-bedroom, 2-bath home in the heart of Bellows Falls. Set on a spacious 1-acre lot, the 1,800-sq-ft interior provides generous room for comfortable everyday living. A private garage and secluded yard offer both practicality and serenity, while the large covered porch invites year-round enjoyment of the outdoors. With Rockingham Rec Park just moments away and all the benefits of an in-town location close at hand, this home offers a peaceful retreat within a well-connected neighborhood—perfect for putting down roots.

$299,900

4 beds1.5 baths1,800 sq ft

10 King St, Bellows Falls, VT 05101

Large covered porch • Private garage • In-town location

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
Welcome to "Sweet Berry Farm", a charming Vermont homestead blending 1850s character with a spacious modern addition. Set on 5.7 private acres in Jamaica, this property offers abundant natural beauty—mature apple trees, blueberry and blackberry bushes and vibrant seasonal gardens. The expanded farmhouse provides exceptional space for living and entertaining. The main floor features an open living and dining area with large windows, a generous kitchen with peninsula, and a separate butler’s kitchen. A wide mudroom and cozy woodstove hearth add to the home’s welcoming feel. The lower level includes a family room, den, bedroom, and bath, ideal for guests. Upstairs,

$875,000

5 beds4.5 baths3,840 sq ft

42 Blackberry Ln, Jamaica, VT 05343

Private acres • Generous kitchen • Butler's kitchen

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
Take a moment to admire this charming Victorian townhouse, nestled on a quiet one-way street. Delightfully landscaped and renovated, the owner has taken care to modernize (heating system, wiring, plumbing, roof, bathrooms, etc. ) without compromising the character & charm we all love. Beautiful maple woodwork and lofty ceilings add to the lovely turn-of-the-century details. With three separate flexible levels that can either connect as a traditional one family home or be used separately, the options with this property are endless. Live on the first floor, enjoy a real fireplace and continue the proven Airbnb business of renting the second and third floors, and live for free. (If this

$395,000

4 beds4 baths2,182 sq ft

39 Williston St, Brattleboro, VT 05301

Modernize plumbing • Modernize wiring • Quiet one-way street

Property at 1555 W River Rd, Dummerston, VT 05301, 2 beds, 1 bath

$285,000

2 beds1 bath903 sq ft

1555 W River Rd, Dummerston, VT 05301

Property at 4106 VT Route 30, Jamaica, VT 05343, 3 beds, 2.5 baths

$299,000

3 beds2.5 baths2,338 sq ft

4106 VT Route 30, Jamaica, VT 05343

Property at 48 Legion Rd, Newfane, VT 05345, 3 beds, 1 bath

$259,000

3 beds1 bath1,712 sq ft

48 Legion Rd, Newfane, VT 05345

Property at 12 Laurel Ave, Bellows Falls, VT 05101, 3 beds, 1 bath

$205,000

3 beds1 bath912 sq ft

12 Laurel Ave, Bellows Falls, VT 05101

Property at 141 Piney Brook Way, Brattleboro, VT 05301-9605, 4 beds, 4 baths

$599,000

4 beds4 baths4,060 sq ft

141 Piney Brook Way, Brattleboro, VT 05301-9605

Property at 88 Westminster St, Bellows Falls, VT 05101, 6 beds, 2.5 baths

$382,000

6 beds2.5 baths3,590 sq ft

88 Westminster St, Bellows Falls, VT 05101

Property at 2418 Vermont Route 11, Londonderry, VT 05148, 3 beds, 2 baths

$485,000

3 beds2 baths1,751 sq ft

2418 Vermont Route 11, Londonderry, VT 05148

Property at 2197 N Main St, Londonderry, VT 05148, 4 beds, 2 baths

$139,000

4 beds2 baths1,910 sq ft

2197 N Main St, Londonderry, VT 05148

Property at 2072 N Main St, Londonderry, VT 05148, 6 beds, 3 baths

$299,000

6 beds3 baths3,942 sq ft

2072 N Main St, Londonderry, VT 05148

Property at 5 Tannery Rd, West Dover, VT 05356, 8 beds, 4 baths

$1,150,000

8 beds4 baths4,828 sq ft

5 Tannery Rd, West Dover, VT 05356

Property at 1909 Davidson Hill Rd, Westminster, VT 05158, 3 beds, 2 baths

$429,900

3 beds2 baths2,140 sq ft

1909 Davidson Hill Rd, Westminster, VT 05158

Property at 34 Williams St, Bellows Falls, VT 05101

$199,000

— beds— baths2,139 sq ft

34 Williams St, Bellows Falls, VT 05101

Property at 58-60 Frost Pl, Brattleboro, VT 05301, 6 beds, 2 baths

$415,000

6 beds2 baths2,048 sq ft

58-60 Frost Pl, Brattleboro, VT 05301

Property at 1909 Pine Banks Rd, Putney, VT 05158, 3 beds, 3 baths

$798,000

3 beds3 baths2,757 sq ft

1909 Pine Banks Rd, Putney, VT 05158

Property at 230 Western Ave, Brattleboro, VT 05301, 4 beds, 2.5 baths

$479,000

4 beds2.5 baths1,887 sq ft

230 Western Ave, Brattleboro, VT 05301

Property at 1089 Marlboro Rd, Brattleboro, VT 05301, 3 beds, 2 baths

$369,000

3 beds2 baths1,703 sq ft

1089 Marlboro Rd, Brattleboro, VT 05301

Property at 11 Fornuto Rd, Wardsboro, VT 05355, 3 beds, 1.5 baths

$285,000

3 beds1.5 baths3,096 sq ft

11 Fornuto Rd, Wardsboro, VT 05355

Property at 25 Upper Handle Rd Unit A, West Dover, VT 05356, 3 beds, 2 baths

$399,000

3 beds2 baths1,400 sq ft

25 Upper Handle Rd Unit A, West Dover, VT 05356

Property at 192 Western Ave, Brattleboro, VT 05301, 3 beds, 2 baths

$568,000

3 beds2 baths2,066 sq ft

192 Western Ave, Brattleboro, VT 05301

Property at 2137 Brockway Mills Rd, Chester, VT 05101, 2 beds, 1 bath

$249,900

2 beds1 bath— sq ft

2137 Brockway Mills Rd, Chester, VT 05101

Property at 93 Clark St, Brattleboro, VT 05301, 3 beds, 1 bath

$90,000

3 beds1 bath1,030 sq ft

93 Clark St, Brattleboro, VT 05301

Property at 24-28 Rockingham St, Rockingham, VT 05101, 2 beds, 1 bath

$750,000

2 beds1 bath17,000 sq ft

24-28 Rockingham St, Rockingham, VT 05101

Property at 876 Route 100, Wilmington, VT 05363, 3 beds, 2 baths

$295,000

3 beds2 baths1,328 sq ft

876 Route 100, Wilmington, VT 05363

Property at 8 Happy Haven Rd, Wilmington, VT 05363, 3 beds, 2 baths

$299,000

3 beds2 baths1,632 sq ft

8 Happy Haven Rd, Wilmington, VT 05363

Property at 87 Townshend Rd, Grafton, VT 05146, 3 beds, 3 baths

$619,000

3 beds3 baths1,800 sq ft

87 Townshend Rd, Grafton, VT 05146

Property at 5362 US Route 5, Westminster, VT 05158, 3 beds, 1 bath

$220,000

3 beds1 bath1,050 sq ft

5362 US Route 5, Westminster, VT 05158

Property at 4 Signal Pine Rd, Putney, VT 05346, 4 beds, 2.5 baths

$789,000

4 beds2.5 baths6,232 sq ft

4 Signal Pine Rd, Putney, VT 05346

Property at 10 Riverfront Dr, Bellows Falls, VT 05101, 2 beds, 2 baths

$275,000

2 beds2 baths1,440 sq ft

10 Riverfront Dr, Bellows Falls, VT 05101

Property at 3715 Route 11, Landgrove, VT 05148, 5 beds, 2.5 baths

$1,075,000

5 beds2.5 baths2,338 sq ft

3715 Route 11, Landgrove, VT 05148

Property at 2015 Vermont Route 30, Townshend, VT 05353, 5 beds, 2 baths

$335,000

5 beds2 baths1,944 sq ft

2015 Vermont Route 30, Townshend, VT 05353

Property at 224 Cobble Ridge Rd, Londonderry, VT 05148, 5 beds, 4.5 baths

$1,470,000

5 beds4.5 baths5,160 sq ft

224 Cobble Ridge Rd, Londonderry, VT 05148

Property at 76 Spruce St, Brattleboro, VT 05301, 4 beds, 3 baths

$425,000

4 beds3 baths3,314 sq ft

76 Spruce St, Brattleboro, VT 05301

Property at 977 Route 121, West Townshend, VT 05359, 4 beds, 3 baths

$499,000

4 beds3 baths3,152 sq ft

977 Route 121, West Townshend, VT 05359

Property at 20 Ray Hill Rd, Wilmington, VT 05363, 4 beds, 5 baths

$749,000

4 beds5 baths3,129 sq ft

20 Ray Hill Rd, Wilmington, VT 05363

Property at 6 Gates Lake Raponda Ln, Wilmington, VT 05363, 2 beds, 1.5 baths

$449,000

2 beds1.5 baths1,416 sq ft

6 Gates Lake Raponda Ln, Wilmington, VT 05363

Property at 58 Oak St, Brattleboro, VT 05301, 5 beds, 4 baths

$625,000

5 beds4 baths3,748 sq ft

58 Oak St, Brattleboro, VT 05301

Viewing page 1 of 2

Vintage Homes for Sale in Windham County

There are currently 77 vintage homes for sale in Windham County at a median listing price of $489K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windham County stay on the market for 100 days. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 61 homes have been sold in Windham County. In addition to houses in Windham County, there were also 85 condos, 6 townhouses, and 16 multi-family units for sale in Windham County last month. Find your dream home in Windham County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windham County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windham County. If you're looking to sell your home in the Windham County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windham County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Windham County, VT

More to explore in Windham County, VT

How to buy a house in Windham County, VT

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Vermont

Burlington homes for sale
$549,900
Stowe homes for sale
$1,225,000
Woodstock homes for sale
$1,195,000
Montpelier homes for sale
$357,500
Brattleboro homes for sale
$375,000
South Burlington homes for sale
$666,130
Shelburne homes for sale
$549,900
Waterbury homes for sale
$450,000
Rutland homes for sale
$269,500
Manchester homes for sale
$1,284,500
Ludlow homes for sale
$592,000
Barre homes for sale
$279,000
Middlebury homes for sale
$482,500
Bennington homes for sale
$249,900
Norwich homes for sale
$0

Copyright 2025 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Fri Dec 05 2025 on the search page

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

Vintage homes for sale & real estate in Windham County, VT

Vintage Homes for Sale in Windham County

More real estate resources for Windham County, VT

Cities

Nearby Counties

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Windham County, VT

How to buy a house in Windham County, VT

Popular Markets in Vermont