Windham Real Estate

Welcome to Windham, Connecticut – a charming town nestled in the heart of Windham County, where history, nature, and community come together to create a vibrant living experience. Known for its rich heritage and picturesque landscapes, Windham is a hidden gem that offers a perfect blend of small-town charm and modern amenities.

As you stroll through the town, you’ll be captivated by its historic architecture and welcoming atmosphere. The downtown area is dotted with quaint shops, local eateries, and cultural landmarks that reflect the town’s diverse heritage. Whether you’re indulging in a delicious meal at a family-owned restaurant or exploring the unique boutiques, Windham has something for everyone.

Nature enthusiasts will find solace in Windham’s beautiful parks and recreational areas. With miles of scenic trails, lush green spaces, and tranquil lakes, outdoor adventures await at every turn. Enjoy a leisurely hike, a picnic with friends, or simply unwind in the serene surroundings – Windham is a haven for those who appreciate the great outdoors.

Education is a cornerstone of the community, with highly-rated schools and a commitment to fostering a nurturing environment for families. The town’s strong sense of community is felt through numerous events and gatherings, where residents come together to celebrate local culture and build lasting connections.

Windham is not just a place to live; it’s a place to thrive. With its rich history, vibrant community, and stunning natural beauty, Windham, Connecticut, is the perfect backdrop for your next chapter. Come and discover the warmth and charm that make Windham a wonderful place to call home!

Newest Listings in Windham

$290,000

3 Beds ⋅ 2 Baths ⋅ 24220426 MLS

This beautifully updated & maintained home is move-in ready and waiting for its new owners! The first floor features high ceilings and consistent flooring throughout, creating a warm and cohesive feel. As you enter through the front door, there is a spacious office featuring beautiful custom wood built-ins. The generously sized dining room, leads to a versatile flex room complete with a laundry closet and half bath. This adaptable space offers endless possibilities and could easily serve as a first-floor bedroom, game room, craft room, or additional living area. The spacious living room provides the perfect place to relax and unwind, featuring a woodstove (serviced in 2026) to keep you cozy during those chilly New England winters. The updated kitchen offers plenty of storage and functionality for all your everyday needs. Upstairs, you'll find three comfortable bedrooms and a full bathroom. Each bedroom features carpeting and large windows that fill the spaces with beautiful natural light. Step outside to enjoy the private, fully fenced backyard, ideal for entertaining or simply relaxing. The outdoor space features a covered porch & patio area, along with a shed that offers excellent storage or the perfect opportunity for a workshop.Blending modern updates with timeless charm, this wonderful home offers flexible living spaces, inviting outdoor areas, and a convenient location close to both ECSU & UCONN. A fantastic opportunity to enjoy all this home has to offer!

89 Spring St, Windham

$299,900

3 Beds ⋅ 1 Baths ⋅ 24220674 MLS

Your First Home Could Be Closer Than You Think! Welcome to this charming, move-in-ready Cape in the heart of Willimantic, where classic New England character meets modern updates and everyday convenience! Whether you're purchasing your first home or looking for a place that's easy to maintain, this inviting 3-bedroom home offers the perfect combination of comfort, functionality, and charm-without the long list of projects! Step inside and discover a bright, open-concept living space filled with thoughtful updates and unique finishing touches. The beautifully refreshed kitchen features granite countertops and stainless-steel appliances, making cooking and entertaining a pleasure. With many major improvements completed within the past four years-including the kitchen, first-floor bathroom, carpeting in the upstairs bedrooms, and newer siding, windows, roof, and furnace-you can spend more time enjoying your home and less time worrying about renovations! Conveniently located near shopping, restaurants, downtown amenities, and commuter routes, this home makes everyday living easy while providing a peaceful place to call your own. Why keep renting when you could start building equity in a place of your own? With its combination of major updates, flexible living space, and inviting outdoor setting, this Willimantic gem is an opportunity worth exploring. Move-in ready, full of charm, and waiting for its next chapter. Schedule your private showing today!

349 Mansfield Ave, Windham

$250,000

3 Beds ⋅ 1 Baths ⋅ 24219261 MLS

There's so much to love about this longtime family home! This inviting Cape offers a comfortable floor plan, nice sized rooms, and wonderful natural light throughout. Invite guests over to enjoy the spacious dining room with vaulted ceilings and oversized windows, while the sunroom/laundry area with wood stove offers another cozy space. The 4th bedroom, previously converted to a den, could be used for an office, extra living space or back to a bedroom to suit your needs. Outside, you'll find a beautifully maintained yard with established gardens, a lovely patio with stone stove, and plenty of room to relax and entertain. A 20x12 workshop with electricity, plus an adjoining covered storage area, is perfect for hobbies, projects, and extra storage. Newer roof, oil tank, and hot water heater add peace of mind. Set in a desirable neighborhood close to Eastern Connecticut State University and with easy access to UConn, this home has been lovingly cared for by the same family for many years and is ready for someone new to bring their vision and make it their own!

21 Pennywood Ln, Windham

$145,000

3 Beds ⋅ 1 Baths ⋅ 24220144 MLS

Investor opportunity in the heart of Willimantic! 26 Ash Ave is a 3 bedroom, 1 bath single family offering 1,119 sq ft of living space on a 5,227 sq ft lot. This circa-1900 home is full of character and ready for its next owner to add value through updates and renovation. Ideal for a fix-and-flip, BRRRR, or long-term rental strategy. The area offers consistent rental demand with convenient access to Eastern Connecticut State University, Windham Hospital, downtown Willimantic, and Routes 6, 32 and 66. Low entry point with solid upside in an active seller's market. Property is being sold in AS-IS condition. Cash or hard money buyers preferred. Bring your contractor and your vision. Easy to show!

26 Ash Ave, Windham

$425,000

4 Beds ⋅ 2 Baths ⋅ 24219643 MLS

Tucked along a quiet country road, this distinctive 4-bedroom, 1.5-bath home sits on 1.36 acres with a wonderful mix of rustic character, versatile living spaces, and opportunities to add your own touches. The property includes a detached garage, barn, established garden areas, and plenty of room for hobbies and outdoor pursuits. Enter through the kitchen, where warm wood cabinetry, exposed beams, tongue-and-groove ceilings, and a generous island create an inviting space for everyday gathering. An extra-wide hallway connects the kitchen to the rest of the home, offering a surprisingly useful area currently enjoyed as a coffee bar and music space. Just beyond is the spacious dining room, complete with shiplap walls and custom shelving, providing plenty of room to gather around the table. The expansive living room is filled with warmth and character, featuring a wood stove, custom barn doors, and an open ceiling that connects to the loft above. The main level also offers bedroom space and a full bathroom, providing options for those who appreciate the convenience of first-floor living. Upstairs, you'll find additional bedrooms of varying sizes and configurations, along with a half bathroom and smaller spaces that lend themselves to a variety of uses. Overlooking the living room, the open loft provides another flexible living area with vaulted wood ceilings, a skylight, and custom barn-door details, currently enjoyed as a retreat for visiting family.

265 Ballamahack Rd, Windham

$280,000

3 Beds ⋅ 1 Baths ⋅ 24216431 MLS

Welcome to 197 Southridge Drive! Nestled in an established Willimantic neighborhood, this classic 3BR, 1BA Raised Ranch offers a perfect blend of modern efficiency, outdoor living space, and a highly convenient location. Make outdoor dining and morning coffee seamless by stepping onto your own private deck just off the kitchen. The deck leads down to a fenced backyard. The partially finished basement offers additional living area plus plenty of storage or future expansion space to suit your needs. Property is located just minutes from Downtown Willimantic's vibrant historic district, you'll have easy access to the weekly Farmers Market and miles off scenic biking and running on the Air Line State Park Trail. This property is ideally situated for students, faculty or investors looking to leverage the local academic community located just minutes away from ECSU and a quick commute to UCONN.

197 Southridge Dr, Windham

$115,000

2 Beds ⋅ 1 Baths ⋅ 24219114 MLS ⋅ Cedar Crest BLDG.

Welcome to Cedar Crest in South Windham! This second-floor end-unit condo features two bedrooms, one full bath, a separate living room, and an eat-in kitchen with room for a dining table. In-unit laundry and two assigned off-street parking spaces add everyday convenience. Located just off Route 32, the condo offers easy access to downtown Willimantic, Eastern Connecticut State University, and UConn's Storrs campus.

270 S Windham Rd Unit 68, Windham

$305,000

5 Beds ⋅ 3 Baths ⋅ 24157885 MLS

Discover the possibilities with this spacious two-family property! Whether you're looking to owner-occupy one unit while utilizing the second or exploring the potential of renting both, this property offers flexibility to suit your needs. Both living spaces feature comfortable areas for relaxing and entertaining, while the kitchens provide ample cabinet and counter space for everyday convenience. Enjoy the generous yard, offering plenty of room for outdoor activities and gatherings. The property may also offer potential for future subdivision or additional development, subject to town approval and buyer due diligence. Don't miss the opportunity to explore all this property has to offer!

125 Mountain St, Windham

$149,900

3 Beds ⋅ 2 Baths ⋅ 24218827 MLS

Spacious, bright, move-in ready and tucked against the woods! This 3-bedroom, 2-bath home in Stonegate Manor offers over 1,600+ square feet with an open layout, vaulted ceilings and a stone fireplace that anchors the living space. Enjoy access to a walking trail leading to the Willimantic Reservoir and surrounding watershed areas. Conveniently located near Route 6, shopping, restaurants and the airport, with public water and sewer. The park has no age restrictions and permits up to two pets per park regulations.

59 Circle Dr, Windham

$8,500

24217749 MLS

.17 Acre residential corner lot located in Windham! Conveniently located on the corner of Cloran and Alice St, with dual road frontage measuring over 95 ft total. Close to local highways and amenities. Buyer to perform all due diligence regarding zoning, utilities, and buildability

28 Cloran St, Windham

$249,700

4 Beds ⋅ 2 Baths ⋅ 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 ⋅ 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

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Windham Real Estate

Newest Listings in Windham

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