Windham County, CT Real Estate Search

Windham County, CT Single Family Homes for Sale

Our website features the best real estate search for single family homes available in Windham County, CT and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Windham County, CT real estate market? Sign up for a  Windham County, CT Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Windham County, CT Single Family Homes for Sale

692 Chestnut Hill Rd, Killingly
$350,000
3 Beds ⋅ 1 Baths ⋅ 24215273 MLS
Charming Ranch in Scenic Killingly, Connecticut! Discover the beauty of country living in this inviting 3-bedroom, 1-full-bath ranch, offering 1,008 square feet of comfortable single-level living on a spacious .46-acre lot. Nestled along the picturesque back roads of Killingly, Connecticut, this property offers a wonderful combination of peaceful surroundings, natural beauty, and everyday convenience. Enjoy the outdoors complete with an oversized back deck, perfect for entertaining, outdoor dining, relaxing, or simply taking in the beautiful New England scenery. An additional outbuilding provides valuable storage space for outdoor equipment, tools, and seasonal belongings. Surrounded by scenic rivers, winding country roads, and vibrant landscapes, this location offers the opportunity to experience the beauty of all four New England seasons. Conveniently situated for an easy commute to both Rhode Island and Massachusetts, this property offers the perfect balance of tranquil country living and accessibility. Whether you're searching for your first home, looking to downsize, or simply seeking a peaceful place to call your own, this charming Killingly ranch is full of possibilities. Your opportunity to own a piece of Connecticut's beautiful Quiet Corner is here! With its desirable single-level layout, generous outdoor space, and convenient location, this property is one you'll want to see for yourself. Don't just imagine the possibilities-come

692 Chestnut Hill Rd, Killingly

Plainfield
$900,000
5 Beds ⋅ 5 Baths ⋅ 24215278 MLS
Welcome to this extraordinary contemporary masterpiece, where architectural elegance meets a semi secluded natural paradise. Perfectly situated on a private wooded lot complete with picket fence that lines driveway. This beautiful 5-bedroom, 4-bathroom home offers the ultimate retreat for modern living and sophisticated entertaining. Step inside to a dramatic, floor plan highlighted by soaring vaulted ceilings and an exquisite stone fireplace that anchors the main living space. Loads of natural light that seamlessly bring the outdoors in. The gourmet, beautifully updated kitchen is a chef's dream, featuring a massive built-in pantry, sleek countertops, and stainless steel appliances. Just above the main living area, a spectacular open loft provides a flexible space ideal for a home office, library, or studio. With five generously sized bedrooms and four completely remodeled bathrooms, there is no shortage of space or comfort. The luxurious primary suite serves as a private oasis within the home, complete with elegant soaking tub and peaceful views of the surrounding tree line. The massive, finished basement expands your living space exponentially. It boasts a massive rec room, offering the perfect setup for a home theater, game room, or private gym. Step outside into your large yard with a pool and large deck. Surrounded by nature and tranquility. A wonderful retreat that is close to major highway. Come see for yourself.

Plainfield

33 Machine Shop Hill 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

30 Hilltop Dr, Woodstock
$350,000
2 Beds ⋅ 1 Baths ⋅ 24214889 MLS
Charming Home on Beautiful Bunggee Lake Experience the beauty of lakeside living in Connecticut's picturesque Quiet Corner! Welcome to this inviting and spacious 2-bedroom ranch, nestled in the beautiful town of Woodstock, Connecticut, along the desirable Bunggee Lake. Whether you're searching for a peaceful year-round residence, a relaxing weekend retreat, or the perfect place to enjoy all four New England seasons, this property offers a wonderful opportunity to embrace the lake lifestyle. Step inside and discover a warm, welcoming home featuring convenient one-level living. The main floor offers two generously sized bedrooms, a full bathroom, a spacious living room, and a comfortable kitchen, providing plenty of room for everyday living and entertaining. The expansive lower level presents incredible potential for additional living space! With its generous size and convenient walkout access, this area offers endless possibilities for a future in-law suite, guest accommodations, recreation room, home office, or additional finished living area. Outside, enjoy the privacy of your own yard and driveway, creating a peaceful setting to relax, entertain, or simply appreciate the natural beauty surrounding you. Imagine experiencing all four seasons in this beautiful lakeside community - warm summer days enjoying the lake, breathtaking autumn foliage, peaceful winter scenery, and the refreshing beauty of spring. Located in Woodstock, one of

30 Hilltop Dr, Woodstock

15 Chaplin St, Chaplin
$469,900
3 Beds ⋅ 2 Baths ⋅ 24214543 MLS
-Step back in time and experience the timeless charm of this distinctive antique brick Colonial, set on approximately 3 acres of beautifully cultivated grounds. Blending historic character with thoughtful modern updates, this 3-bedroom, 2-full-bath home offers inviting living spaces, multiple fireplaces, and an exceptional chef's kitchen featuring an oversized island, stone countertops, new appliances, a large basin sink, and a convenient pantry. The kitchen overlooks the spectacular outdoor setting, where nearly 1,100 square feet of newly laid bluestone patio provides the perfect backdrop for entertaining, outdoor dining, or simply enjoying the surrounding gardens. The main level also features a bedroom, full bathroom, additional sitting room or formal dining room, and a grand living room rich with character. Upstairs, two generously sized bedrooms include a walk-in closet and dressing room, with an additional full bathroom completing the second floor. Modern comforts include Mitsubishi heating and cooling splits, a main-level pellet stove, and a high-end Biasi B10 Series boiler. The grounds are equally impressive, offering a thoughtfully established homestead with seven apple trees, three plum trees, two cherry trees, two peach trees, two fig trees, established hydrangeas, perennial flower gardens, specialty ornamental trees, and three large garden areas, all enhanced by beautiful stone walls. A partially unfinished rear section currently used for storage adds a

15 Chaplin St, Chaplin

524 Wauregan Rd, Brooklyn
$699,000
3 Beds ⋅ 4 Baths ⋅ 24214629 MLS
Welcome to this exceptional, custom built brick home, set on a stunning piece of property where quality, craftsmanship, and timeless design come together beautifully. From the moment you step inside, you will appreciate the vaulted ceilings, open layout, and impressive mix of hardwood, marble and tile flooring. The heart of the home features a beautifully designed kitchen with quartz countertops, custom built cupboards, 2 ovens, trash compactor and more! The dining room features a wood-burning fireplace that's never been used! With enough room for the largest table. Off the kitchen, enjoy a heated sunroom that offers peaceful views overlooking the inground pool and hot tub, create a perfect space to relax year-round. The main level offers a spacious primary suite with a separate sitting room, custom walk in closet. The en suite features a soaking tub and walk in shower with a heated lamp, double sink vanity and marble countertops. An office on the main floor provides flexibility for working from home or additional living space. Convenient first floor laundry with a half bath adds every day practicality. Upstairs you'll find two additional bedrooms and a full bathroom. The heated basement has an additional half bathroom and offers endless possibilities for recreation, wood shop, storage, gym, or finished space. Additional features include a four car garage, central air, Buderus, furnace, water softener, 200 amp, electrical service, and security system. This is a rare opportuni

524 Wauregan Rd, Brooklyn

54 Westford Rd, Eastford
$574,900
3 Beds ⋅ 2 Baths ⋅ 24212900 MLS
Step onto this property and you are immediately taken with its beauty. Mature landscaping filled with ornamental and native trees including 1000's of spring bulbs, summer lilies, and other perennials surrounded by the stone walls that characterize so much of New England charm. This 1900's home has been carefully updated to highlight its character and history with all the conveniences we have learned to love. The entry way welcomes you with vintage cherry floors, The kitchen has been completely remodeled with new cabinets, quartz countertops, and new appliances. The back ell consists of a walk-in pantry, an oversized mud room with laundry and new 3/4 bath as well as an office with private entrance on the first floor. Spacious Dining room, featuring Washington fir floors is right off the kitchen. The large living room with fireplace, is open to sunroom/family room with ample space for you to spread out and enjoy entertaining. A beautiful staircase leads to three bedrooms, all with wood flooring and remodeled full bathroom. There are possibilities for an in-law suite with not too much effort. Refinished plaster walls and fresh paint throughout. Almost 4 acres gives you room to spread your wings. Open field, perfect for grazing your animals. Concrete pad, ready for your new garage or barn. Most windows replaced; roof on the ell of the house is brand new. Mechanicals are up to date. Ready to for you to move right in!

54 Westford Rd, Eastford

367 Mashentuck Rd, Killingly
$655,000
4 Beds ⋅ 4 Baths ⋅ 24212443 MLS
Welcome home to this impressive 4-5 BD, 3.5 BA custom Colonial set on 1.85 acres in desirable Killingly setting! Offering generous living space, exceptional versatility, & outdoor amenities, this home is designed for comfortable living & entertaining. Step inside to discover beautiful hdwds throughout dining room, great room, & den. Spacious kitchen is sure to impress with granite, stainless appliances, & breakfast bar-perfect for morning coffee, casual meals, & gathering with family & friends. Gas FP adds warmth & ambiance, while the expansive great room features a vaulted ceiling & sliders leading to a large deck with pergola overlooking the inviting in-ground pool with new liner. Primary suite offers a relaxing retreat with an ensuite bath featuring whirlpool tub, double sink vanity & walk-in closet. Three additional light-filled bdrms provide room for family, guests, or a home office. One of this home's standout features is the large bonus room above the garage with its own private entrance & full bath-ideal for extended-stay guests, teen hangout, or flexible living space. Outside, enjoy your own private retreat with a fenced yard, firepit, & raised garden beds. Three storage sheds, with electricity, provide space for equipment & storage. RV pad with 30-amp electric. 2-car heated garage with multiple shelves & cabinets. C/A, oil heat, generator ready, new well pump tank, new washer & dryer, & mounted TVs & surround sound system. Make this exceptional home yours!

367 Mashentuck Rd, Killingly

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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.

How much is your home worth?

Get instant property value now!