Vintage homes for sale & real estate in Windham, CT

13 homes

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ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Rare find kind of property! This property is complete with many incredible features. First Cape style home is 4 beds and 1.5 baths. Carpeted living room, first floor bedroom with a secondary bedroom that is currently being used as laundry room. Two additional rooms upstairs. Updated Galley style kitchen with granite countertops and plenty of cabinet space. Smaller eatin or informal dining area which leads into great room that looks out over the back yard. Oversized two car garage with lots of room for storage. All the mechanicals are updated including new furnace, electric hot water heater and oil tank. This home is equipped with a propane whole house generator. Your completely fenced in ba

$289,900

4 beds1.5 baths1,715 sq ft

41 Ashland St, Willimantic, CT 06226

Two story barn • Cape style home • Screened in gazebo

ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Welcome home to this beautifully maintained 2-bedroom, 1-bath ranch nestled in a welcoming Windham community. This move-in-ready home offers excellent condition throughout, with a thoughtfully finished basement providing valuable additional living space. A one-car garage adds convenience and storage, while the lovely landscaping creates inviting curb appeal and a pleasant outdoor setting. Ideally located near shopping, medical facilities, universities, and area casinos, this home offers easy access to everyday amenities and entertainment. A wonderful opportunity for those seeking comfort, convenience, and a well-cared-for home in a desirable location.

$239,000

2 beds1 bath864 sq ft

18 Laurel Ln, Windham, CT 06280

One car garage • Inviting curb appeal • Finished basement

ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
If you're looking for a spacious investment property or a home where you can add your own personal touches, this could be the one! Ideally located close to Eastern Connecticut State University, this 4-bedroom Colonial offers excellent potential as a housing investment, especially with a separate in-law apartment. The home features generously sized rooms, beautiful wood floors, some updated windows, and a cozy wood stove. Outside, enjoy a beautifully landscaped, fully fenced-in yard, a huge screened-in back porch-perfect for relaxing or entertaining-and a detached one-car garage. With its desirable location, flexible living space, and plenty of potential, this property is a wonderful opportu

$335,000

4 beds2.5 baths2,379 sq ft

130 Windham Rd, Willimantic, CT 06226

Fully fenced-in yard • Updated windows • 0.42 acre lot

ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Bring your vision to this six-bedroom home in Willimantic's Hill Section. With approximately 1,948 square feet of living space, the property features generously sized rooms, hardwood flooring, tall windows, original woodwork, and period details throughout. A brand-new roof has already been installed, providing a great start for future improvements. With thoughtful updates, this home has the potential to showcase its original character while being tailored to its next owner. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shopping, dining, and major routes. Property is being sold as-is. Also available is 15 Bellevue Street, located at the front of the pr

$175,000

6 beds2 baths1,948 sq ft

11 Bellevue St, Willimantic, CT 06226

Hardwood flooring • Tall windows • Period details

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Whether you're looking for abundant living space, room for extended household members, or an investment opportunity, this spacious 5-bedroom, 2-bath home offers exceptional flexibility in a prime Windham location. The home features generously sized bedrooms, updated bathrooms, and a versatile floor plan that can easily adapt to a variety of needs. A possible sixth bedroom on the first floor provides even more options for a home office, guest room, or additional living space. Previously utilized as a 6-bedroom rental, the home offers an abundance of space and functionality. A detached 2-car garage and expansive driveway provide ample parking, while the generous . 41-acre lot offers a surpris

$362,500

6 beds2 baths2,181 sq ft

371 Prospect St, Willimantic, CT 06226

Spacious yard • Expansive driveway • Generous lot

Property at 15 Bellevue St, Willimantic, CT 06226, 4 beds, 1.5 baths

$199,000

4 beds1.5 baths1,807 sq ft

15 Bellevue St, Willimantic, CT 06226

Property at 27 Gamache Ln, North Windham, CT 06256, 4 beds, 2 baths

$274,900

4 beds2 baths1,648 sq ft

27 Gamache Ln, North Windham, CT 06256

Property at 86 Chestnut St, Willimantic, CT 06226, 4 beds, 2 baths

$290,000

4 beds2 baths1,560 sq ft

86 Chestnut St, Willimantic, CT 06226

Property at 33 Machine Shop Hill Rd, South Windham, CT 06266, 4 beds, 3.5 baths

$549,900

4 beds3.5 baths2,548 sq ft

33 Machine Shop Hill Rd, South Windham, CT 06266

Property at 207 Summit St, Willimantic, CT 06226, 3 beds, 2 baths

$365,000

3 beds2 baths2,318 sq ft

207 Summit St, Willimantic, CT 06226

Property at 14 Carey St, Willimantic, CT 06226, 6 beds, 3 baths

$299,900

6 beds3 baths2,700 sq ft

14 Carey St, Willimantic, CT 06226

Property at 260 Summit St, Willimantic, CT 06226, 9 beds, 4 baths

$480,000

9 beds4 baths2,939 sq ft

260 Summit St, Willimantic, CT 06226

Property at 129 Walnut St, Willimantic, CT 06226, 4 beds, 1 bath

$219,000

4 beds1 bath1,078 sq ft

129 Walnut St, Willimantic, CT 06226

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ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Welcome to this 7 room, 2 bath, ranch style home, with a detached garage, located on 2 Acres. set back off the road. If you have been looking for country living, this may be your home. Fully applianced kitchen (laundry set-up conveniently located), Kitchen eating nook, plus a formal dining room. All located on one floor living. Bring your ideas. lots of potential to make it your own. Notice needed.

$279,900

3 beds2 baths1,652 sq ft

337 Hampton Rd, Chaplin, CT 06235

Formal dining room • Ranch style home • 2 acres

OPEN SAT, 10:30AM TO 12PM

ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Charming, move in ready, and full of opportunity, this well cared for ranch offers the perfect blend of comfort, convenience, and timeless appeal. Tucked away on a quiet street, you'll immediately appreciate the peaceful setting and beautifully maintained grounds that create a private retreat just minutes from everyday essentials. Inside, a spacious living room welcomes you with a large picture window that fills the space with natural light, while the inviting eat in kitchen features stainless steel appliances, newer laminate flooring, and a charming greenhouse window that is perfect for herbs, flowers, or your morning coffee. Two comfortable bedrooms provide cozy spaces to unwind, with har

$275,000

2 beds1 bath984 sq ft

9 Buckingham Rd, Mansfield Center, CT 06250

Large picture window • Eat in kitchen • Spacious living room

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Classic Craftsman style, inviting spaces and a beautiful setting come together at 216 Trumbull Highway! Cape Cod shake siding and a welcoming front porch set the tone for this charming 3-bedroom, 2-full-bath home offering over 2,400 sq ft of nicely flowing living space. Inside, hardwood floors add warmth and character, while the country kitchen offers plenty of room for a dinette. The spacious floor plan includes a dining room, living room with built-in bookshelves, and family room with sliders opening to a large back deck-perfect for enjoying the private yard bordered by mature trees that are sure to put on a spectacular show come autumn! The full basement is partially finished with excell

$399,900

3 beds2 baths2,463 sq ft

216 Trumbull Hwy, Lebanon, CT 06249

Country kitchen • Built-in bookshelves • Craftsman style

ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Welcome to this well-maintained 4-bedroom Cape Cod-style home, peacefully situated at the end of a quiet street. Well maintained and thoughtfully upgraded, this home offers comfort, functionality, and peace of mind. The heated breezeway provides a welcoming entrance and convenient access to the attached garages. The spacious kitchen offers plenty of room for cooking and entertaining and features newer appliances installed in 2024. Just off the kitchen, the comfortable living room features a fireplace and hardwood flooring creating a warm and inviting space to relax and gather. Mini-split systems on each level provide efficient cooling and welcome relief on hot summer days. The main level in

$385,000

4 beds1 bath1,478 sq ft

17 Buckingham Rd, Mansfield Center, CT 06250

Remodeled bathroom • Spacious kitchen • Newer appliances

SHORT SALE

ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Discover the possibilities at 165 Huntington Road in scenic Scotland, Connecticut. Set on over 21 acres of picturesque countryside and surrounded by the natural beauty of northeastern Connecticut, this unique property offers open space and endless opportunities to roam, recreate, or simply enjoy the peaceful setting. Inside you'll find three bedrooms to include a generously sized Master Bedroom. Enjoy the jacuzzi tub in the attached private bathroom. At the other end of the residence is an enormous Great Room that can serve as an entertainment space for years to come. A wrap around deck adds a little extra to take in the scenic view. Relax in the sunroom year-round while enjoying peace of t

$515,000

3 beds3.5 baths3,052 sq ft

165 Huntington Rd, Scotland, CT 06264

Over 21 acres • Wrap around deck • Sunroom

ABOUT THIS HOME
Vintage Home for sale in Windham, CT:
Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra bedrooms, a home office, playroom, gym, or guest space - perfect for today's flexible lifestyle needs. Tucked away in a truly special setting, this home is surrounded by federal land, offering direct access to scenic hiking and horseback riding trails just steps from your door. Enjoy the peace and pr

$419,900

5 beds2.5 baths2,887 sq ft

13 Bates Rd, Chaplin, CT 06235

Hardwood flooring • Porch • Newer boiler

Vintage Homes for Sale in Windham

There are currently 13 vintage homes for sale in Windham at a median listing price of $290K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windham stay on the market for 42 days and receive 1 offers. This map is refreshed with the newest listings in Windham every 15 minutes.

In the past month, 17 homes have been sold in Windham. In addition to houses in Windham, there were also 4 condos, 0 townhouses, and 4 multi-family units for sale in Windham last month. Find your dream home in Windham 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 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windham. If you're looking to sell your home in the Windham area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windham with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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