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

101 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
PRICE REDUCTION-- to Sell! It is possible to live rent or mortgage free and here’s your opportunity. This fully rented, three unit multi family property is already generating income. Live in one unit and let the other two cover your expenses, or bring your own vision to life in this premier location. Zoned for both commercial and residential use, the possibilities are extensive. Imagine a riverfront restaurant with al fresco dining, a new retail shop, an exercise or hot yoga studio, an art gallery, or continue with office and wellness services the property currently includes office space and a massage therapy business. The offering includes two houses, one apartment unit, an office sp

$350,000

7 beds4 baths3,551 sq ft

1950 N Main St, Londonderry, VT 05148

Ample parking • Generating income • Waterfront

FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
Stately Victorian-era building built in 1865, featuring large windows and sweeping covered porches. It offers a unique opportunity to own a commercial property tucked between the Brattleboro Public Library and a historic stone church. Sitting high above Main Street with views of Mount Wantastiquet, this building has had the same owners for over 3 decades, and served as headquarters for real estate companies. With over 5300 square feet and an attached two story annex with separate entrances, the building enjoys 13 rooms /offices, 5 half baths, historic fireplaces, and 7 exterior entrances. The two story layout, plus the attic and poured concrete full basement is well suited for a variety of

$475,000

8 beds0.5 baths5,300 sq ft

214 Main St, Brattleboro, VT 05301

Large windows • Historic fireplaces • Two story layout

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
This Vermont Country Farmhouse has been recently completed renovated and is ready for turn key enjoyment. The property consists of 41+ acres with tremendous exposure and easy main road access, extensive pasture which could easily be used for farming, a 42x48 post and beam barn, multiple out buildings ideal for workshops and storage, and a location with easy access to Harriman Reservoir and not far from skiing and villages. Truly an ideal location for anyone looking for a Vermont retreat, hobby farm, country getaway, or whatever your heart may desire. The home itself has been renovated with contemporary stylings including a gorgeous open concept great room with exposed original woodwork and

$599,000

5 beds2 baths2,350 sq ft

9282 VT Rte 100, Whitingham, VT 05361

41 acres • Access to skiing • Post and beam barn

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
Charming Farmhouse Gem in the Heart of Londonderry Welcome home to this inviting 2-bedroom, bonus room and 2-bathroom residence centrally located in Londonderry, VT a dream location for outdoor enthusiasts with quick, convenient access to world-class skiing at Magic, Bromley, Stratton, and Okemo Mountains in the winter. Summer and fall you are close to hiking the multitude of trails, kayaking, swimming or fishing at a one of the nearby state parks. The local coffee shop is within walking distance as well as the Londonderry Farmers Market! Inside, the home features classic farmhouse-style decor and warm, bright natural light throughout its comfortable living spaces. Step outside into a priv

$360,000

2 beds2 baths1,841 sq ft

5892 Route 100, Londonderry, VT 05148

Classic tree swing • Cozy fire pit • Custom treehouse

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Windham County, VT:
TWO HOMES | 1BR BARN APARTMENT | RESTORED VINTAGE BARN | 13+ ACRES. A rare Vermont multi-residence estate offering two beautifully renovated homes, a separate 1BR barn apartment, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm blends authentic character, exceptional craftsmanship, and modern four-season comfort. One residence is a restored 4BR farmhouse once used as the summer home of renowned art historian Meyer Schapiro, with wide-plank floors, antique doors, an expanded kitchen with soapstone counters, updated baths, and custom built-ins. Schapiro’s former art studio now serves as a self

$2,430,000

9 beds7 baths4,996 sq ft

494-564 Goodaleville Rd, Jamaica, VT 05343

1br barn apartment • 13 acres • Private hot tubs

Property at 54 Williams St, Bellows Falls, VT 05101, 4 beds, 2 baths

$125,000

4 beds2 baths2,644 sq ft

54 Williams St, Bellows Falls, VT 05101

Property at 634 Lower Dover Rd, Marlboro, VT 05344, 5 beds, 6 baths

$2,290,000

5 beds6 baths4,400 sq ft

634 Lower Dover Rd, Marlboro, VT 05344

Property at 455 S Main St, Brattleboro, VT 05301, 3 beds, 1 bath

$269,000

3 beds1 bath1,050 sq ft

455 S Main St, Brattleboro, VT 05301

Property at 13 Kimball Hl, Putney, VT 05346, 3 beds, 4 baths

$849,000

3 beds4 baths4,240 sq ft

13 Kimball Hl, Putney, VT 05346

Property at 37 Stowe Hill Rd, Wilmington, VT 05363, 4 beds, 2.5 baths

$624,900

4 beds2.5 baths2,904 sq ft

37 Stowe Hill Rd, Wilmington, VT 05363

Property at 54 Main St, Grafton, VT 05146, 4 beds, 2.5 baths

$639,000

4 beds2.5 baths2,128 sq ft

54 Main St, Grafton, VT 05146

Property at 2435 Stage Rd, Guilford, VT 05301, 6 beds, 6.5 baths

$750,000

6 beds6.5 baths3,877 sq ft

2435 Stage Rd, Guilford, VT 05301

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

$749,900

4 beds2.5 baths6,232 sq ft

4 Signal Pine Rd, Putney, VT 05346

Property at 3 Eldredge Rd, Chester, VT 05143, 5 beds, 5 baths

$1,600,000

5 beds5 baths6,118 sq ft

3 Eldredge Rd, Chester, VT 05143

Property at 1033 Burrington Hill Rd, Whitingham, VT 05361, 5 beds, 2.5 baths

$335,000

5 beds2.5 baths2,336 sq ft

1033 Burrington Hill Rd, Whitingham, VT 05361

Property at 6036 Jacksonville Stage Rd, Halifax, VT 05358, 5 beds, 1 bath

$725,000

5 beds1 bath1,224 sq ft

6036 Jacksonville Stage Rd, Halifax, VT 05358

Property at 2060 Townshend Rd, Grafton, VT 05146, 6 beds, 4 baths

$2,895,000

6 beds4 baths3,946 sq ft

2060 Townshend Rd, Grafton, VT 05146

Property at 3327 Route 30, Jamaica, VT 05343, 5 beds, 2 baths

$439,000

5 beds2 baths2,194 sq ft

3327 Route 30, Jamaica, VT 05343

Property at 494-498 Goodaleville Rd, Jamaica, VT 05343, 5 beds, 4 baths

$1,315,000

5 beds4 baths2,974 sq ft

494-498 Goodaleville Rd, Jamaica, VT 05343

Property at 116 Birge St #2, Brattleboro, VT 05301, 1 bed, 1 bath

$239,000

1 bed1 bath1,320 sq ft

116 Birge St #2, Brattleboro, VT 05301

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

$755,000

5 beds2.5 baths2,338 sq ft

3715 Route 11, Landgrove, VT 05148

Property at 50 Oak Grove Ave, Brattleboro, VT 05301, 4 beds, 3 baths

$340,000

4 beds3 baths1,918 sq ft

50 Oak Grove Ave, Brattleboro, VT 05301

Property at 258 Chester Rd, Grafton, VT 05146, 3 beds, 4 baths

$734,000

3 beds4 baths4,285 sq ft

258 Chester Rd, Grafton, VT 05146

Property at 1329 Newfane Rd, Wardsboro, VT 05355, 3 beds, 1 bath

$299,900

3 beds1 bath1,192 sq ft

1329 Newfane Rd, Wardsboro, VT 05355

Property at 4850 Route 100, Wardsboro, VT 05355, 4 beds, 2 baths

$350,000

4 beds2 baths1,830 sq ft

4850 Route 100, Wardsboro, VT 05355

Property at 673 VT Rte 121 E, Grafton, VT 05146, 5 beds, 2.5 baths

$549,000

5 beds2.5 baths3,000 sq ft

673 VT Rte 121 E, Grafton, VT 05146

Property at 238 Stowe Hill Rd, Wilmington, VT 05363, 9 beds, 9 baths

$2,950,000

9 beds9 baths6,726 sq ft

238 Stowe Hill Rd, Wilmington, VT 05363

Property at 6795 VT Route 100, Londonderry, VT 05148, 4 beds, 2 baths

$339,000

4 beds2 baths2,460 sq ft

6795 VT Route 100, Londonderry, VT 05148

Property at 246 Mann Rd, Wilmington, VT 05363, 1 bed

$249,000

1 bed— baths468 sq ft

246 Mann Rd, Wilmington, VT 05363

Property at 19 Canal St, Brattleboro, VT 05301, 9 beds, 4 baths

$399,000

9 beds4 baths3,286 sq ft

19 Canal St, Brattleboro, VT 05301

Property at 219 High St #3, Brattleboro, VT 05301, 1 bed, 1 bath

$139,000

1 bed1 bath592 sq ft

219 High St #3, Brattleboro, VT 05301

Property at 42 Blackberry Ln, Jamaica, VT 05343, 5 beds, 4.5 baths

$799,000

5 beds4.5 baths3,840 sq ft

42 Blackberry Ln, Jamaica, VT 05343

Property at 53 Hickory Ridge Rd S, Putney, VT 05346, 7 beds, 6 baths

$1,475,000

7 beds6 baths6,292 sq ft

53 Hickory Ridge Rd S, Putney, VT 05346

Property at 350 Sunset Lake Rd, Newfane, VT 05362, 4 beds, 3 baths

$1,000,000

4 beds3 baths3,632 sq ft

350 Sunset Lake Rd, Newfane, VT 05362

Property at 2245 Burrington Hill Rd, Whitingham, VT 05361, 4 beds, 1 bath

$1,150,000

4 beds1 bath1,972 sq ft

2245 Burrington Hill Rd, Whitingham, VT 05361

Property at 9 Mountain Acres Rd, Jamaica, VT 05343, 4 beds, 2 baths

$595,000

4 beds2 baths1,430 sq ft

9 Mountain Acres Rd, Jamaica, VT 05343

Property at 33 Oak St, Brattleboro, VT 05301

$375,000

— beds— baths4,116 sq ft

33 Oak St, Brattleboro, VT 05301

Property at 131,133,141 Green St, Brattleboro, VT 05301, 11 baths

$1,350,000

— beds11 baths7,660 sq ft

131,133,141 Green St, Brattleboro, VT 05301

Property at 148 Townshend Rd, Grafton, VT 05146, 3 beds, 2 baths

$679,000

3 beds2 baths2,100 sq ft

148 Townshend Rd, Grafton, VT 05146

Property at 16 School St, Brattleboro, VT 05301, 12 beds, 6 baths

$499,000

12 beds6 baths6,000 sq ft

16 School St, Brattleboro, VT 05301

Property at 341 Under The Mountain Rd, South Londonderry, VT 05155, 5 beds, 3 baths

$600,000

5 beds3 baths2,635 sq ft

341 Under The Mountain Rd, South Londonderry, VT 05155

Viewing page 2 of 3

Vintage Homes for Sale in Windham County

There are currently 101 vintage homes for sale in Windham County at a median listing price of $473K. 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 84 days. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 58 homes have been sold in Windham County. In addition to houses in Windham County, there were also 114 condos, 0 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

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

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
$509,000
Stowe homes for sale
$1,061,950
Woodstock homes for sale
$975,000
Montpelier homes for sale
$438,900
South Burlington homes for sale
$688,500
Brattleboro homes for sale
$289,000
Waterbury homes for sale
$440,000
Rutland homes for sale
$300,000
Ludlow homes for sale
$599,000
Shelburne homes for sale
$650,000
Waitsfield homes for sale
$515,000
Middlebury homes for sale
$499,000
Manchester homes for sale
$995,000
Bennington homes for sale
$259,000
Norwich homes for sale
$849,000

Copyright 2026 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 Mon Oct 19 2026 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

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.