Windham Real Estate

Welcome to Windham, Connecticut—a charming town nestled in the heart of Windham County. With its rich history, vibrant community, and picturesque landscapes, Windham offers a unique blend of small-town charm and modern conveniences that make it an ideal place to call home.

Founded in the 17th century, Windham boasts a rich tapestry of historical significance. The town’s historic district features beautifully preserved buildings that tell the story of its past, offering residents and visitors alike a glimpse into the area’s heritage. Stroll through the quaint downtown area, where you’ll find local boutiques, cozy cafes, and delightful eateries, all contributing to the town’s inviting atmosphere.

Nature enthusiasts will adore Windham’s stunning outdoor spaces. The town is surrounded by lush forests and scenic parks, perfect for hiking, biking, and enjoying the great outdoors. The nearby Natchaug State Forest offers miles of trails and serene picnic spots, making it a favorite destination for families and adventurers.

Windham is also known for its strong sense of community. The town hosts various events throughout the year, from farmers’ markets to seasonal festivals, fostering connections among residents and creating a welcoming environment for newcomers. With a focus on education and family-friendly activities, Windham is an excellent place to raise children.

Whether you’re drawn to its historical charm, vibrant community spirit, or beautiful surroundings, Windham, CT, offers a delightful lifestyle that combines the best of both worlds. Explore this hidden gem and discover why so many have chosen to make Windham their home!

Newest Listings in Windham

$299,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24216737 MLS

Investors Take Notice! Bring your vision and unlock the potential of this Victorian-style two-family property at 55 Main Street in Willimantic. Each unit offers 2 bedrooms and 1 bath, with both bathrooms recently updated with brand-new finishes. While the property would benefit from additional updating and improvements, the opportunity to build equity and maximize its potential is well worth exploring. Ideally located across from Recreation Park, near Eastern Connecticut State University and UConn, and within walking distance to local amenities and the bus line. Whether you're an investor seeking your next project or an owner-occupant looking to offset your mortgage with rental income, this property offers exciting possibilities. Bring your ideas, envision the possibilities, and schedule your showing today!

55 Main St, Windham

$329,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24216414 MLS

Step into a truly one-of-a-kind home where history, character, and creativity come together. Originally built circa 1892 as the historic Hilltop Hose Company No. 3 Firehouse, this remarkable property has been thoughtfully transformed into an eclectic single-family residence while honoring its architectural roots. The 1,000-square-foot first floor offers an expansive open layout with soaring ceilings, creating an impressive space for everyday living and entertaining. Nearly as spacious, the versatile third-floor retreat includes a full bathroom, extensive built-in storage, counter space, and a private balcony-making it ideal as a generous primary suite, guest room, living area, home office, creative studio, or flexible multigenerational living space. Distinctive Art Deco-inspired design elements add personality throughout, creating a home unlike any other. The composite and stone patio, landscaped yard, and the refreshing shade of mature trees make it an ideal spot to enjoy your morning coffee or unwind at the end of the day. The impressive stone foundation basement boasts high ceilings, a laundry area with utility sink, and clean storage space. Conveniently located near Eastern Connecticut State University, downtown Willimantic's restaurants, shops, entertainment, and local events, with easy access to Route 6 and a short drive to UConn. A rare opportunity to own a distinctive property where historic charm and modern comfort blend into an unforgettable place to call home.

207 Summit St, Windham

$389,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24216131 MLS

Pride of ownership shines throughout this beautifully maintained circa 1953 Ranch, nestled on 1.38 acres of picturesque, park-like grounds! Quality built and lovingly cared for, this inviting 3-bedroom, 1-bath home offers comfortable one-level living with timeless charm and thoughtful updates. Inside, discover gleaming hardwood floors, a spacious living room with fireplace, adjoining dining area, and a bright kitchen featuring natural wood cabinetry and ample storage. A true highlight is the expansive 48'x17' 3-season sunroom, surrounded by windows and sliders offering wonderful views of the beautifully landscaped grounds. Perfect for relaxing, entertaining, or simply enjoying nature's changing seasons! Outside, sweeping lawns, mature trees, ornamental plantings, and lovely garden areas create a peaceful retreat. A covered patio, two storage sheds, paved driveway, and attached 2-car garage add convenience and versatility. Significant improvements include the roof, windows, sliders, updated electrical, mini-split systems, and a new boiler. Central air and a generator hookup provide additional comfort and convenience. A wonderful combination of solid construction, meticulous maintenance, and natural beauty, this special property is ready for its next chapter. Come experience it for yourself! Owner is a licensed real estate agent in VT.

106 Jerusalem Rd, Windham

$365,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215945 MLS

Country living at its best with this Contemporary Cape w/1711sqft, 3 Bedrm, 3 Full Baths, HUGE 1000 plus sqft BARN/GARAGE/OUTBUILDING ON 2.64 ac of level land with a stream. Perfect property for hobbys, animals, storage, wood working, home based business and much more. Open floor plan w/ 2 Foyer entrances w/ tiles floors, open kitchen & dining rm with slider to your private deck. Living rm with a woodstove. 1st floor large bedrm w/ full bath with tile floor & adorable barn doors. 2nd floor has a Master suite w/ Full bath w/a jacuzzi tub. 2nd master bed w/vaulted ceilings & french doors to a private deck. Separate office, play rm or could be a large walkin closet & a 3rd FULL BATH. BARN/OUT BUILDING/ GARAGE w/ a full attic floored. So many possibilities in this home. Bring your horses, home based business, 4 wheelers, dirt bike, green house, storage, man cave, garage, chicken coop & so much MORE. Sits privately off the road with lots of space for gardens on a nice level lot. Many updates throughout the years including windows, roof, septic tank, well tank & much more. Solar panels to save money on power. Power bill is approx 80 dollars a month. Sits on a dead end street. Come live in the country close to all major routes, airport, Hartford, cssinos for ONLY 365,000

33 Old Brooklyn Tpke, Windham

$229,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24215087 MLS

Adorable ranch/split level home! Convenient yet quiet non through road. Walk to the bus lines and shopping. Cute 2 bedroom home with updated bath, living room with fireplace. LVP and tile flooring throughout.Three outbuildings, side porch, and front patio. Heated lower level needs updating but great for expansion. Attached garage and walkout basement. Newer septic tank.Great backyard, paved driveway, set up a showing today.

38 Crystal Rd, Windham

$519,900

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24215433 MLS

Beautifully Remodeled Home with Modern Updates & Separate In-Law Living! Welcome to this beautifully renovated home offering the perfect combination of modern comfort, spacious living, and versatility! Thoughtfully updated throughout, this home features an inviting layout designed for today's lifestyle. The main living area offers 3 spacious bedrooms, 2.5 bathrooms, and a dedicated home office. The bright, open-concept kitchen, dining, and living areas create a seamless flow, perfect for everyday living and entertaining. Convenient main-level laundry adds to the home's functionality. A separate in-law living area provides an excellent opportunity for multigenerational living, extended family, or guests. This private space features 1 bedroom, 1 full bathroom, its own laundry area, and a comfortable living space, all conveniently located on the first floor. Extensive renovations throughout, including a new roof and new furnace, offer added value and peace of mind. Step outside to enjoy the spacious deck, ideal for outdoor entertaining, relaxing, or hosting summer gatherings. The property also features two detached garages, including an oversized heated garage offering exceptional space for vehicles, storage, a workshop, or hobbies. With its beautifully updated interior, flexible living arrangements, and impressive garage space, this property offers something for everyone. Move-in ready and full of possibilities-schedule your private showing today!

33 Machine Shop Hill Rd, Windham

$324,999

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214512 MLS

Imagine summer mornings with coffee on the new Trex deck, afternoons spent by your in-ground pool, and evenings launching a kayak right into the river behind your backyard. At 15 Cracow Ave, that lifestyle comes together with the comfort of an updated 3-bedroom, 2-bath ranch where many of the big-ticket improvements have already been taken care of. Inside, the open floor plan was made for gathering. The remodeled kitchen features quartz countertops and soft-close cabinetry and opens directly into the dining area and spacious living room, where a wood-burning fireplace becomes the centerpiece on cooler New England nights. Down the hall, the true primary suite gives you something rarely found at this price point-a private full bathroom with double vanities-along with two additional bedrooms and a second full bath.

15 Cracow Ave, Windham

$495,000

ACTIVE Status ⋅ 24215007 MLS

303 Boston Post Road, North Windham, CT, offers a compelling opportunity to acquire a high-visibility commercial property along the Route 6 retail corridor at a lighted corner. Priced at $495,000, this single-story brick/masonry building features approximately 1,500 SF on the first floor plus a 1,500 SF basement, providing flexibility for office, service, or adaptive-reuse potential. Surrounded by major national retailers including Walmart, The Home Depot, Tractor Supply Co., and Dunkin', the property benefits from strong commercial synergy and daily exposure along a corridor with approximately 16,900 vehicles per day. The site is well positioned for users seeking an established location with existing improvements, public water and sewer, and strong visibility in one of North Windham's primary retail areas. This property also presents an exciting value-add or redevelopment angle, with potential to explore a compact coffee or quick-service concept, subject to approvals.

303 Boston Post Rd, Windham

$217,500

4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24213182 MLS

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 standout feature is the impressive two-story garage with access from two streets, offering exceptional convenience, storage, or potential workshop space. The full walk-out lower level adds additional functionality and flexibility. Ideally located close to local colleges, this property presents an excellent opportunity for investors, owner-occupants, or those seeking rental potential. Enjoy nearby delicious eateries, unique shops, and easy commuting access to surrounding towns and major routes. This is a truly charming and classic New England home that must be seen to be fully appreciated.

129 Walnut St, Windham

$578,520

ACTIVE Status ⋅ 24212010 MLS

New Roof (2011), Natural Gas Heat (Converted 2012), New Chimney Liner (2012). City Water, Sewer & Gas. Town owned. They will rezone for you depending on your use.

47 Crescent St, Windham

$499,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24210893 MLS

Beautiful new country home to be built on a picturesque 1.03-acre lot, offering the perfect blend of quality, comfort, and modern design. The thoughtfully designed open floor plan features solid wood flooring, vaulted ceilings in the living and dining rooms, and an abundance of natural light. The custom kitchen will showcase granite countertops and plenty of space for cooking and entertaining. Enjoy the convenience of 2 full baths plus a half bath, central air conditioning, and an attached 2-car garage. This is your opportunity to personalize and customize a brand-new home to fit your style and needs. Build the home you've been dreaming of in a peaceful country setting!

7 Scarborough Rd, Windham

$288,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24210578 MLS

Welcome to this well-cared-for home, where thoughtful updates and a comfortable layout create an inviting place to call home. The spacious eat-in kitchen provides plenty of room for meals and entertaining and flows naturally into the living area. The home offers three bedrooms and a well-maintained bathroom. A full walkout basement provides excellent potential space, whether you need a recreation room, home office or workshop. Outside, you'll find a private deck, paved driveway, an a carport for convenient parking and outdoor enjoyment. The roof was newly installed in September 2026, providing an important recent improvement for the next owner. With its comfortable floor plan, outdoor amenities, and opportunity to expand, this home offers plenty of room to make it your own. Situated in a peaceful and desirable part of town, the property is also conveniently located near UConn and Eastern Connecticut State University.

154 Manners Ave, Windham

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Windham Real Estate

Newest Listings in Windham

How much is your home worth?

How much is your home worth?