Windham Real Estate

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

With roots dating back to the 17th century, Windham is steeped in history. The town boasts a number of historic sites and landmarks, including the beautiful Windham Historic District, where you can stroll past well-preserved colonial homes and quaint storefronts. The picturesque landscapes, featuring lush parks and serene waterways, provide the perfect backdrop for outdoor enthusiasts. Whether you enjoy hiking, fishing, or simply relaxing in nature, Windham has plenty to offer.

Windham is also home to a diverse and welcoming community, with a variety of local events and festivals throughout the year that bring residents together. From farmers’ markets to seasonal celebrations, there’s always something happening in town. Families will appreciate the strong educational system, with well-regarded schools that prioritize student achievement and community involvement.

In addition to its historical charm and community spirit, Windham offers easy access to major highways, making it convenient for commuters traveling to nearby cities. With a range of housing options, from cozy single-family homes to modern apartments, there’s something for everyone in this delightful town.

Discover the charm of Windham, CT, where history meets community, and make it your next home sweet home!

Newest Listings in Windham

$145,000

3 Beds ⋅ 2 Baths ⋅ 24204778 MLS

This Cute, Clean and Spacious, 3-bedroom, 2 bath home in the Stonegate Manor has 1152 Square Feet of Living Space. Appliances convey. There is an 8x10 Shed that conveys as well. Updates are as follows.... Roof is only 2 years old, and hot water heater only 3-4 years old. New flooring and subflooring in primary bedroom/bath. 2 pets are allowed per park regulations. Park has No age requirement! This home abuts the woods with a Walking Trail leading to the Willimantic Reservoir and surrounding Natchaug River and Mansfield Hollow watershed system. Close to Route 6, Airport, shopping, restaurants and more. Public water and public sewer.

57 Circle Dr, Windham

$634,900

10 Beds ⋅ 5 Baths ⋅ 24204552 MLS

Income producing multi family property offering a strong opportunity for investors or owner occupants alike. One unit is currently not leased, providing immediate leasing potential or flexibility for owner occupancy. Property presents the opportunity to generate rental income with additional upside potential over time. Detached garage offers added utility with potential for storage, workshop space, or future supplemental income opportunities. Conveniently located near Eastern Connecticut State University, downtown Willimantic, shopping, dining, and major commuter routes. Great opportunity to add a multifamily asset to an investment portfolio.

120 North St, Windham

$489,900

3 Beds ⋅ 2 Baths ⋅ 24202685 MLS

Welcome to this beautifully maintained open-concept ranch, built in 2008 and situated on a private, level 3.6-acre lot. Offering 3 bedrooms and 2 full bathrooms, this home combines modern comfort with spacious single-level living. The bright, open floor plan features gleaming hardwood floors, tray and cathedral ceilings and two gas fireplaces. The kitchen boasts stainless steel appliances, granite countertops, tall cabinets and a convenient desk area. You'll find a seamless flow between the kitchen, dining, and living areas, making it ideal for both everyday living and entertaining. A sun-filled sunroom provides the perfect spot to relax and enjoy views of the surrounding property, while the deck offers additional outdoor living space for gatherings or peaceful mornings. Car enthusiasts, hobbyists, and those in need of extra storage will appreciate the impressive 5-car garage capacity, including an attached 3-car garage and a detached 2-car garage. The expansive 2100 sq ft basement presents excellent potential for future finishing with a bath location already plumbed in. The possibilities are endless to create additional living space, a recreation room, home gym, or workshop. Don't miss this opportunity to own a move-in-ready ranch with room to grow both inside and out!

6 Zoldak Dr, Windham

$324,900

3 Beds ⋅ 1 Baths ⋅ 24203041 MLS

Welcome to 14 Tunxis Lane! This well-maintained 3-bedroom, 1-bathroom home is move-in ready and offers a wonderful opportunity for its next owner. Recent improvements include newer windows, a new front entry door, and refreshed landscaping, enhancing both curb appeal and functionality. Situated near a quiet cul-de-sac, the property offers a peaceful and private setting with a spacious back and side yard - a rare find in this area. The home has been thoughtfully maintained over the years and provides a comfortable layout with plenty of opportunity to personalize and make it your own. The lower level offers additional space and potential for a future second bathroom, providing an opportunity to expand the home's functionality and value. Whether you're a first-time buyer, downsizing, or simply looking for a well-cared-for home in a private setting, 14 Tunxis Lane is a rare opportunity you won't want to miss!

14 Tunxis Ln, Windham

$289,900

4 Beds ⋅ 2 Baths ⋅ 24202429 MLS

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 back yard is home to a screened in gazebo, a carefree detached garage, a storage shed and an unbelievable two story barn which has electric and insulated on lower level (WAIT until you see this barn!! Possible make it an ADU or second living space. THIS IS THE ONE YOU HAVE BEEN LOOKING FOR!!!! Priced to be VERY COMPETETIVE. Just a short walk to park springs or a little bit longer walk to center of town.

41 Ashland St, Windham

$315,000

5 Beds ⋅ 3 Baths ⋅ 24202946 MLS ⋅ Oak Forest Village BLDG.

Welcome to desirable Oak Forest Village. This move-in-ready home offers one of the most spacious floor plans in the complex, with 3 bedrooms on the main floor and 2 on the lower level for ample room to spread out. With two and a half baths, enjoy the privacy of a primary bedroom with an en suite full bath. The open-concept living space features a remodeled kitchen with modern two-tone cabinets, stainless steel appliances, granite countertops and a breakfast bar, along with a designated dining area and a spacious living room with a vaulted ceiling. Perfect for both quiet nights in and holiday hosting. The hardwood floors were just refinished in preparation for the sale, and the half bath in the finished lower level was recently remodeled as well. A 2-car garage with automatic openers offers easy access and additional storage, while the deck and backyard provide space for gatherings, gardening, and outdoor relaxation. You're conveniently close to many amenities, including shopping, dining, golf, ECSU plus the Charles H. Barrows STEM Academy right on Tuckie Rd, and walking trails right behind the neighborhood. All ready and waiting for you!

18 Hilltop Dr Unit 18, Windham

$315,000

5 Beds ⋅ 3 Baths ⋅ 24202822 MLS

18 Hilltop Dr Unit 18, Windham

$239,000

2 Beds ⋅ 1 Baths ⋅ 24202236 MLS

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.

18 Laurel Ln, Windham

$152,000

3 Beds ⋅ 2 Baths ⋅ 24202840 MLS

Welcome to 6 Circle Drive, a spacious 3-bedroom, 2-full-bath mobile home located in North Windham's Stonegate Manor mobile home park. Situated on a corner lot, this home features a large kitchen, generously sized bedrooms, and decent closet space throughout. The primary bedroom includes an en-suite bath with a relaxing jacuzzi soaking tub. Enjoy approximately 340 sq. ft. of side decking, perfect for outdoor entertaining or relaxing. Conveniently located near shopping plazas, restaurants, and other local amenities. A great opportunity for comfortable, and practical living!

6 Circle Dr, Windham

$290,000

4 Beds ⋅ 2 Baths ⋅ 24201649 MLS

INVESTOR OPPORTUNITY IN WILLIMANTIC! Bring your vision to 86 Chestnut Street, an approximately 1,560 SF multifamily property. Originally built in 1887, the property offers timeless architectural character and charm rarely found in newer construction. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shops, restaurants, services, and major area routes. Offered AS-IS, providing an opportunity to renovate and customize to your investment strategy. The property's character, layout, location, and value-add potential make this an excellent opportunity for an investor or owner-occupant. Cash or conventional financing only. No government financing. Buyer to conduct their own due diligence regarding condition, zoning, intended use, and renovation potential.

86 Chestnut St, Windham

$362,500

6 Beds ⋅ 2 Baths ⋅ 24200868 MLS

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 surprisingly spacious yard with plenty of room to enjoy the outdoors. Located just steps from Eastern Connecticut State University and close to shopping, dining, and major commuter routes, this property combines space, convenience, and versatility in one unique package. Whether you're searching for a spacious primary residence or a property with strong income potential, this home is full of opportunity.

371 Prospect St, Windham

$199,000

4 Beds ⋅ 2 Baths ⋅ 24201064 MLS

Bring your vision to this four-bedroom home in Willimantic's Hill Section. With approximately 1,807 square feet of living space, the property features generously sized rooms, tall windows, original woodwork, and period details throughout. 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 11 Bellevue Street, located behind the property, creating the possibility of a package purchase.

15 Bellevue St, Windham

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