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

$115,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189539 MLS

Welcome to this well-maintained 2008 mobile home located in the desirable Stonegate Manor community. This inviting home offers a bright, open floor plan filled with natural light, creating a warm and welcoming atmosphere throughout. The spacious kitchen flows seamlessly into the living room, making it perfect for everyday living and entertaining. Offering three bedrooms and two full baths, this home provides plenty of space for family and guests. The primary suite features a large walk-in closet and a private bath. Step outside to enjoy the nice deck overlooking the backyard, an ideal spot for morning coffee, outdoor dining, or simply relaxing. There's also space for gardening or creating your own outdoor retreat. Conveniently located close to shopping, parks, and other local amenities, this home combines comfort, convenience, and value. Park approval is required. Don't miss this wonderful opportunity to make Stonegate Manor your new home!

37 Pond Way, Windham

$299,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24192959 MLS

Ranch-style home offering the convenience of one-level living just outside the city. Features include hardwood floors, a freshly painted interior, an inviting sunroom with skylights, and a stunning stone fireplace. The level, landscaped yard is fenced in and perfect for outdoor enjoyment. Recent updates include new flooring in the foyer, kitchen, and hallway, plus newly updated bathroom and a new water heater! A partially finished lower level provides extra living space. Conveniently located near Routes 6, 32, and 66 with easy access to Hartford, New London, Worcester, Eastern Connecticut State University, and UConn.

39 Selden St, Windham

$309,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24192676 MLS

Affordable & Move-in ready 4-bedroom, 1.5-bath Cape offering over 1,300 sq. ft. of comfortable living space, with potential to add more sqft in the semi-finished basement. Conveniently located near shopping, dining, and everyday amenities, as well as Eastern Connecticut State University and the University of Connecticut. Eligible for USDA financing, making homeownership more accessible for qualified buyers. Why rent when you can own? Schedule your showing today!

30 Russ Rd, Windham

$399,900

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24192242 MLS

Timeless New England charm meets modern-day opportunity in this impressive 5-bedroom, 3.5-bath antique Colonial, where historic character and spacious living come together on a picturesque setting. Rich in original details, this one-of-a-kind home showcases wide-plank hardwood floors, stunning decorative fireplaces with ornate mantels, oversized windows, and classic architectural craftsmanship throughout. The spacious country kitchen offers ample room for gathering and opens to multiple living and entertaining spaces, including a formal dining room, inviting family room, and generously sized bedrooms filled with natural light. A flexible floor plan provides endless possibilities for today's lifestyle, whether you're looking for space for a home office, guest quarters, or multi-generational living. Outside, the property continues to impress with a welcoming covered front porch, expansive yard, and an oversized detached 2-car garage/barn offering exceptional storage, workshop space, or hobby potential. Surrounded by mature trees and timeless New England scenery, this remarkable property delivers the perfect balance of privacy, history, and functionality. Whether you're drawn to the craftsmanship of a bygone era or looking for a home with room to grow, this exceptional antique Colonial is ready for its next chapter. Schedule your private showing today and experience the character and possibilities this unique property has to offer.

394 Jerusalem Rd, Windham

$499,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24191550 MLS

Experience exceptional craftsmanship in this magnificent timber frame home, thoughtfully designed with quality, comfort, and energy efficiency in mind. The stunning great room features soaring ceilings and an open-concept layout that flows seamlessly into the dining area and custom kitchen, creating an ideal space for everyday living and entertaining. A cozy propane stove adds warmth and ambiance during the winter months. Constructed with Structural Insulated Panels (SIPs) and built with meticulous attention to detail, this home offers outstanding energy performance. Additional features include radiant oil-fired underfloor heating, indirect hot water, an energy recovery ventilator (ERV), quarter-sawn wood flooring, and beautifully crafted custom kitchen cabinetry. Situated on a level, open cul-de-sac lot, the property offers both privacy and space to enjoy the outdoors. An attached screened gazebo provides the perfect setting for relaxing, dining, or entertaining while enjoying the fresh air in comfort. This is an ideal home for the discerning buyer, with quality and efficiency that is at the edge of building technology.

6 Autumn Rdg, Windham

$289,500

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24191945 MLS

Unique property! 1920s Dutch Colonial with many new upgrades. Small private lot that is easy to maintain. Front and rear porches. Adjacent to Amer ican Legion Field and close to Jillson Square. Come take a look! Kitchen cabinet doors are currently off, and are being given a fresh coat of white paint. They will be installed prior to closing.

Windham

$215,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24190308 MLS ⋅ Elm Tree Village BLDG.

Move-in ready 2-bedroom, 1.5-bath townhouse-style condo offering comfortable, low-maintenance living in a desirable community. The main level features a spacious living room, a kitchen with updated appliances, designated dining area and a convenient half bath. Upstairs are two generously sized bedrooms and a full bathroom. The full basement provides abundant storage, washer and dryer hookups, and potential for additional finished living space. Major mechanical updates include a new heating system, central air conditioning, and water heater, all replaced within the past year. Additional highlights include an attached one-car garage, driveway parking for two vehicles, and access to community tennis courts. Conveniently located near shopping, restaurants, and major routes while offering a quiet residential setting. A great opportunity for owner-occupants or investors alike.

29 Kathleen Dr Unit 5C, Windham

$299,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24190236 MLS

Located in the highly desirable Upper Hills neighborhood of Willimantic, just a short distance to Eastern Connecticut State University, this charming Colonial blends timeless character with an unbeatable location. Offering over 2,000 square feet of living space, this home features four spacious bedrooms, one and a half bathrooms, soaring ceilings, original hardwood floors throughout and a classic wood-burning fireplace that creates a warm and inviting atmosphere. The oversized rooms provide exceptional flexibility. Outside, enjoy relaxing on the covered front porch or entertaining on the beautiful bluestone paver patio. Additional highlights include newer replacement windows, a one-car detached garage and mature landscaping that enhances the home's curb appeal. This property presents an excellent opportunity seeking a home with income potential. Conveniently located near Eastern Connecticut State University, shopping, restaurants, parks and major commuter routes, this is a rare opportunity to own a classic Colonial in one of Willimantic's most sought-after neighborhoods.

232 North St, Windham

$269,000

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24190067 MLS

Do you need an IN-LAW apartment? A Home business? May even be a possible 2 family. It's Possible with this home. Check the Town Hall for all possibilities. VERY LARGE single-family home with 5 bedrooms and 1 1/2 bathrooms. Nice yard, HUGE Dining room, Large Kitchen, a dramatic entrance to the second level!!! Two separate decks, bay windows with lots of natural light. Property needs some work, but the elbow grease will make you TONS of equity. Come look and make an offer!!!

1008 Windham Rd, Windham

$229,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189211 MLS ⋅ Windham Oaks BLDG.

End unit condo in one of the most sought-after complexes in Nice. Features include a modern kitchen with granite countertops, tile backsplash, and ample cabinet storage. The open-concept living and dining area boasts vaulted ceilings and an abundance of natural light from large windows. Main-level half bath for convenience. Upstairs, the spacious primary bedroom offers vaulted ceilings, a skylight, and plenty of sunlight. Full bathroom with tub and shower combo. Enjoy a prime location-just a short walk to town, with access to parks, dining, shopping, and more. Lower level can be finished for additional living space.

366 Ash St Unit 1, Windham

$299,900

6 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24187426 MLS

Excellent opportunity to own a spacious 2-family home with great flexibility for investors or owner-occupants. The first unit offers 2 bedrooms and 1 full bath, while the second unit features a generous 4-bedroom, 2-bath layout, providing plenty of space for larger households or strong rental potential. A 2-car garage adds valuable parking and storage, making this property even more attractive. Whether you're looking to expand your investment portfolio, live in one unit and rent the other, or accommodate extended living arrangements, this multi-family home offers versatility, functionality, and long-term value. Sold as is where is. Needs work

14 Carey St, Windham

$315,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24181796 MLS

Investors and owner-occupants take notice! Well-maintained fully rented, with tenants in place, two-family home situated on a quiet dead-end street. Each unit offers 2 bedrooms, 1 full bath, and approximately 1,000 square feet of living space, providing spacious layouts and strong rental appeal. Separate utilities make management simple, while laundry hookups in the basement add convenience for tenants. Situated on nearly a half-acre lot, the property offers plenty of outdoor space, Large front porch and an abundance of off-street parking. Conveniently located close to shopping, dining, schools, and major routes. Whether you're looking to expand your investment portfolio or secure a future owner-occupied opportunity, this versatile multi-family property is not to be missed.

11 Type Rd, Windham

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