Windham Homes for Sale

Welcome to Windham, Connecticut – a charming town that beautifully blends rich history with modern living. Nestled in Windham County, this picturesque community is known for its vibrant atmosphere, friendly neighborhoods, and a strong sense of community spirit. With its roots dating back to the 17th century, Windham boasts a wealth of historical landmarks, scenic parks, and cultural attractions that make it a delightful place to call home.

One of the highlights of Windham is its diverse array of homes for sale, catering to a variety of lifestyles and preferences. Whether you’re seeking a quaint colonial-style house with timeless charm, a contemporary family home with spacious layouts, or a cozy cottage nestled among the trees, Windham has something to offer everyone. The real estate market here is thriving, with properties that not only provide comfort and style but also access to excellent schools, recreational facilities, and local amenities.

Residents enjoy a plethora of outdoor activities, from hiking in the nearby parks to exploring the scenic trails that Windham has to offer. The town is also conveniently located, providing easy access to major highways and nearby cities, making it an ideal spot for commuters.

In Windham, you’ll find a welcoming community with annual events, farmer’s markets, and local shops that highlight the charm of small-town living. If you’re ready to find your dream home in a place that feels like a retreat, explore the homes for sale in Windham and discover the perfect blend of comfort, community, and convenience. Your new adventure awaits!

Newest Windham Homes for Sale

$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

$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

$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

$389,000

3 Beds ⋅ 1 Baths ⋅ 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

$359,000

3 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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

$499,900

4 Beds ⋅ 4 Baths ⋅ 24215433 MLS

Looking for a home with a little extra room to spread out? This beautifully renovated single-family home offers the perfect combination of modern updates, comfort, and flexibility! One of its standout features is the additional first-floor living space, offering added privacy and versatility for a variety of lifestyle needs. This separate area features comfortable finished living space, a full bathroom, and its own laundry area, providing convenience and functionality. The bright, open-concept kitchen, dining, and living areas create a welcoming atmosphere perfect for everyday living and entertaining. A dedicated home office provides additional flexibility, while convenient main-level laundry adds even more functionality. Extensively remodeled throughout, this move-in-ready home showcases beautiful modern updates, including a new roof and new furnace, offering added value and peace of mind. Step outside to enjoy the spacious deck, perfect for relaxing or entertaining. 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 floor plan, additional first-floor living space, and impressive garage accommodations, this property offers more than meets the eye! Enjoy the comfort of single-family living with a little extra space to make your own. Schedule your private showing today!

33 Machine Shop Hill Rd, Windham

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Windham Homes for Sale

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