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

104 homes

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ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Move-In Ready Ranch in an Excellent Location! Welcome home to this adorable, move-in-ready ranch offering 2 bedrooms and 1 full bath. Thoughtfully updated and filled with charm, this home features a welcoming front porch-perfect for relaxing with your morning coffee or unwinding at the end of the day. The updated kitchen boasts beautiful granite countertops and offers a functional space for preparing meals and entertaining. A charming sunroom provides additional living space and offers endless possibilities for a cozy sitting area, home office, reading nook, or year-round enjoyment. Step outside to the rear patio, an ideal spot for outdoor dining, entertaining, or simply enjoying the fresh

$289,900

2 beds1 bath696 sq ft

32 Pomfret Rd, Brooklyn, CT 06234

Charming sunroom • Front porch • Updated kitchen

OPEN SAT, 12PM TO 2PMFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Welcome to 208 Bass Rd, a charming three-bedroom, one-bath mid-century modern ranch nestled on a desirable corner lot. Surrounded by elaborate gardens and natural landscaping, this home offers a tranquil, secret-garden setting complete with a relaxing back deck and vibrant butterfly bushes. Inside, character abounds with classic arched detailing, rich wood accents, and newly refinished hardwood floors (2026). The inviting living room features a cozy fireplace and built-in bookshelves, flowing seamlessly into the dining area and a functional kitchen with a cozy breakfast nook. A standout great room boasts floor-to-ceiling windows and an independent AC/heat split, creating a bright and flexib

$449,000

3 beds1 bath2,161 sq ft

208 Bass Rd, Windham, CT 06280

Natural landscaping • Wood accents • Back deck

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Opportunity awaits at 488 School Street in Putnam! Built in 1930, this home offers 6 rooms, including 3 bedrooms and 1.5 baths, set on a . 41-acre lot. Features include a detached one-car garage, full unfinished basement, mudroom, and a woodstove that can provide an alternative heat source and help offset today's high heating costs. While the home is dated and would benefit from cosmetic updates, it remains livable and move-in ready, offering buyers the chance to make improvements over time and add their own personal touches. The exterior has areas of peeling paint that will need attention and may limit financing options, so buyers should consult with their lender regarding property conditi

$270,000

3 beds1.5 baths1,154 sq ft

488 School St, Putnam, CT 06260

Woodstove • Mudroom • 0.41 acre lot

SHORT SALE

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Charming Antique Colonial - Prime Windham Location Step back in time and experience the warmth and character of this classic 1915 Antique Colonial, beautifully situated on a desirable corner lot in Windham. This inviting home offers four spacious bedrooms and one full bath, along with a generously sized living room perfect for relaxing or entertaining. The bright eat-in kitchen provides a welcoming space for gatherings and everyday living. Enjoy peaceful mornings or cozy seasonal evenings in the sun-filled three-season room, complete with stairs leading directly out to the backyard. The property is surrounded by a charming white picket fence, enhancing its timeless New England appeal. A sta

$217,500

4 beds1 bath1,078 sq ft

129 Walnut St, Willimantic, CT 06226

Two-story garage • Three-season room • White picket fence

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
A great opportunity to call Putnam home while enjoying the added benefit of rental income! This spacious two-family property offers approximately 3,198 square feet of living space, with two bedrooms and one full bath in each unit. One unit will be delivered vacant, making this an ideal setup for an owner-occupant looking for the comfort of their own space while having rental income from the second unit help offset monthly expenses. Inside, you'll find generous living areas, hardwood floors, and classic character throughout, along with a functional two-family layout that offers plenty of flexibility. A detached two-car garage and driveway provide convenient off-street parking and additional

$399,000

4 beds2 baths3,198 sq ft

346 Church St, Putnam, CT 06260

In ground pool • New roof • Close to downtown

Property at 7 Amidon Dr, Ashford, CT 06278, 3 beds, 2 baths

$599,900

3 beds2 baths1,372 sq ft

7 Amidon Dr, Ashford, CT 06278

Property at 31 Depot Rd, Plainfield, CT 06239, 5 beds, 1 bath

$209,900

5 beds1 bath1,939 sq ft

31 Depot Rd, Plainfield, CT 06239

Property at 10 Homestead Rd, Dayville, CT 06241, 4 beds, 2 baths

$400,000

4 beds2 baths2,272 sq ft

10 Homestead Rd, Dayville, CT 06241

Property at 602 N Main St, Killingly, CT 06239, 3 beds, 2 baths

$269,000

3 beds2 baths1,467 sq ft

602 N Main St, Killingly, CT 06239

Property at 89 John Perry Rd, Eastford, CT 06242, 4 beds, 2.5 baths

$625,000

4 beds2.5 baths4,538 sq ft

89 John Perry Rd, Eastford, CT 06242

Property at 20 Bradley St, Putnam, CT 06260, 5 beds, 2 baths

$169,900

5 beds2 baths2,767 sq ft

20 Bradley St, Putnam, CT 06260

Property at 990 Riverside Dr, North Grosvenordale, CT 06255, 5 beds, 1.5 baths

$424,900

5 beds1.5 baths2,132 sq ft

990 Riverside Dr, North Grosvenordale, CT 06255

Property at 225 Woodstock Ave, Putnam, CT 06260, 4 beds, 2 baths

$419,900

4 beds2 baths1,897 sq ft

225 Woodstock Ave, Putnam, CT 06260

Property at 540 Squaw Rock Rd, Moosup, CT 06354, 3 beds, 2 baths

$449,900

3 beds2 baths1,856 sq ft

540 Squaw Rock Rd, Moosup, CT 06354

Property at 101 Beaver Dam Rd, Woodstock Valley, CT 06282, 4 beds, 2 baths

$339,900

4 beds2 baths1,712 sq ft

101 Beaver Dam Rd, Woodstock Valley, CT 06282

Property at 6 Old Route 12, Thompson, CT 06277, 9 beds, 3.5 baths

$349,999

9 beds3.5 baths4,336 sq ft

6 Old Route 12, Thompson, CT 06277

Property at 5 Eastford Rd, Eastford, CT 06242, 4 beds, 1.5 baths

$329,900

4 beds1.5 baths3,324 sq ft

5 Eastford Rd, Eastford, CT 06242

Property at 19 North Rd, Ashford, CT 06278, 4 beds, 1 bath

$379,900

4 beds1 bath2,332 sq ft

19 North Rd, Ashford, CT 06278

Property at 78 Hammond Hill Rd, Hampton, CT 06247, 4 beds, 2 baths

$449,900

4 beds2 baths2,002 sq ft

78 Hammond Hill Rd, Hampton, CT 06247

Property at 178 Farrows St, Putnam, CT 06260, 3 beds, 2 baths

$345,000

3 beds2 baths1,344 sq ft

178 Farrows St, Putnam, CT 06260

Property at 45 Fairview St, Killingly, CT 06239, 2 beds, 1 bath

$315,000

2 beds1 bath832 sq ft

45 Fairview St, Killingly, CT 06239

Property at 91 Church St, Thompson, CT 06277, 5 beds, 3.5 baths

$799,000

5 beds3.5 baths2,990 sq ft

91 Church St, Thompson, CT 06277

Property at 10 Centennial St, Putnam, CT 06260, 3 beds, 1 bath

$289,000

3 beds1 bath956 sq ft

10 Centennial St, Putnam, CT 06260

Property at 85 Robertson Ave, Killingly, CT 06239, 4 beds, 2 baths

$393,000

4 beds2 baths1,904 sq ft

85 Robertson Ave, Killingly, CT 06239

Property at 500 Route 169, Woodstock, CT 06281, 5 beds, 3.5 baths

$779,000

5 beds3.5 baths2,467 sq ft

500 Route 169, Woodstock, CT 06281

Property at 29 Vandall St, North Grosvenordale, CT 06255, 3 beds, 2 baths

$499,000

3 beds2 baths4,907 sq ft

29 Vandall St, North Grosvenordale, CT 06255

Property at 108 Krapf Rd, Ashford, CT 06278, 3 beds, 1.5 baths

$399,000

3 beds1.5 baths1,564 sq ft

108 Krapf Rd, Ashford, CT 06278

Property at 354 Pomfret St, Pomfret Center, CT 06259, 6 beds, 4.5 baths

$975,000

6 beds4.5 baths4,601 sq ft

354 Pomfret St, Pomfret Center, CT 06259

Property at 28 Lovers Ln, Windham, CT 06280, 2 beds, 1 bath

$189,000

2 beds1 bath1,000 sq ft

28 Lovers Ln, Windham, CT 06280

Property at 357 Wrights Crossing Rd, Pomfret Center, CT 06259, 5 beds, 5.5 baths

$2,500,000

5 beds5.5 baths7,772 sq ft

357 Wrights Crossing Rd, Pomfret Center, CT 06259

Property at 110 Church St, Putnam, CT 06260, 7 beds, 2.5 baths

$475,000

7 beds2.5 baths3,071 sq ft

110 Church St, Putnam, CT 06260

Property at 31 Canterbury Rd, Brooklyn, CT 06234, 4 beds, 3.5 baths

$485,000

4 beds3.5 baths2,879 sq ft

31 Canterbury Rd, Brooklyn, CT 06234

Property at 122 Child Hill Rd, Woodstock, CT 06281, 4 beds, 3 baths

$679,000

4 beds3 baths3,865 sq ft

122 Child Hill Rd, Woodstock, CT 06281

Property at 160 Halls Hill Rd, Danielson, CT 06239, 3 beds, 1.5 baths

$699,900

3 beds1.5 baths3,119 sq ft

160 Halls Hill Rd, Danielson, CT 06239

Property at 9 Ellen Ln, Woodstock, CT 06281, 6 beds, 3 baths

$499,900

6 beds3 baths3,214 sq ft

9 Ellen Ln, Woodstock, CT 06281

Property at 813 Westford Rd, Ashford, CT 06278, 3 beds, 2 baths

$533,000

3 beds2 baths2,010 sq ft

813 Westford Rd, Ashford, CT 06278

Property at 259 Ference Rd, Ashford, CT 06278, 3 beds, 2 baths

$219,000

3 beds2 baths3,243 sq ft

259 Ference Rd, Ashford, CT 06278

Property at 137-139 S Chestnut St, Plainfield, CT 06387, 8 beds, 2 baths

$365,000

8 beds2 baths2,522 sq ft

137-139 S Chestnut St, Plainfield, CT 06387

Property at 19 Bellevue St, Willimantic, CT 06226, 5 beds, 2 baths

$349,900

5 beds2 baths2,678 sq ft

19 Bellevue St, Willimantic, CT 06226

Property at 1-5 Mountain Hill Rd, North Grosvenor Dale, CT 06255, 6 beds, 3 baths

$499,900

6 beds3 baths1,296 sq ft

1-5 Mountain Hill Rd, North Grosvenor Dale, CT 06255

Property at 1 Library Rd, Canterbury, CT 06331, 3 beds, 2.5 baths

$425,000

3 beds2.5 baths2,123 sq ft

1 Library Rd, Canterbury, CT 06331

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Vintage Homes for Sale in Windham County

There are currently 104 vintage homes for sale in Windham County at a median listing price of $389K. 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 43 days and receive 1 offers. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 138 homes have been sold in Windham County. In addition to houses in Windham County, there were also 38 condos, 1 townhouse, and 47 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.

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