Windham Homes with Colonial Style

Welcome to Windham County, Connecticut, a hidden gem nestled in the heart of New England. This picturesque region is celebrated for its rich history, charming small towns, and stunning natural landscapes. With its rolling hills, serene lakes, and lush forests, Windham offers a peaceful retreat for those seeking a harmonious blend of rural charm and modern amenities. The county is home to a vibrant community, featuring local farmers' markets, unique shops, and delightful dining options that showcase the best of Connecticut’s culinary scene.

One of Windham County's most enchanting features is its array of Colonial-style homes. These timeless residences exude character and charm, often characterized by their symmetrical facades, gabled roofs, and classic white picket fences. Colonial homes in this area often come with spacious interiors, hardwood floors, and beautifully landscaped yards, making them perfect for families and individuals alike. Imagine sipping your morning coffee on a quaint porch or hosting gatherings in a grand living room filled with natural light.

Living in Windham County means immersing yourself in a community that values tradition while embracing modern living. The area boasts excellent schools, abundant recreational opportunities, and a strong sense of community spirit. Whether you’re exploring the scenic trails of the nearby state parks or enjoying a cultural event in one of the charming towns, Windham County truly has something for everyone.

If you’re looking for a home that embodies history and elegance, the Colonial-style residences in Windham County are sure to capture your heart. Come discover the allure of this beautiful region and find your perfect home today!

Newest Windham Homes with Colonial Style

$399,600

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24195021 MLS

CHARMING 1752 QUINTESSENTIAL CENTER CHIMNEY COLONIAL ON NEARLY 2 ACRES OF PRETTY LANDSCAPE. LOVINGLY MAINTAINED FOR OVER 40 YEARS THIS CAPTIVATING CLASSIC FEATURES ORIGINAL PERIOD DETAILS HIGHLIGHTING 5 WORKING FIREPLACES WOW, FUNCTIONAL BEEHIVE OVEN, ORIGINAL BUTTERY, WONDERFUL CHESTNUT AND PINE WIDE BOARD FLOORS AND 2 STAIRCASES. SPACIOUS EAT-IN-KITCHEN WITH UPDATED STAINLESS APPLIANCES, CORIAN COUNTEROPS AND FARMHOUSE SINK SIT BY THE FIRPLACE AND ENJOY! THE KITCHEN OPENS TO A KEEPING ROOM WHERE YOU CAN GATHER AROUND THE BEEHIVE OVEN AND HEARTH. THE MAIN LEVEL CONTINUES WITH THE FORMAL DINING ROOM, PINK PARLOR AND DEN WHICH LEADS TO RELAXING TIME IN THE SCREENED IN PORCH. THE SECOND FLOOR BOASTS AN ELEGANT PRIMARY BEDROOM WITH FIREPLACE AND 2-3 ADDITIONAL VERSATILE BEDOOMS COULD ALSO BE USED FOR AN OFFICE, EXTRA CLOSET OR PLAYROOM. FABULOUS 2ND FLOOR LAUNDRY ROOM. ATTIC SPACE SURPRISES. 3 CAR GARAGE. SHED/MANCAVE. NUMEROUS UPGRADED MECHANICALS INCLUDING NEWER DRILLED WELL, OIL TANK AND MORE. CANTERBURY IS RICH IN LOCAL HISTORY AND THIS HOME IS A TRUE GEM!

11 N Canterbury Rd, Canterbury

$365,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24195071 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

$429,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192043 MLS

Welcome home to the heart of Connecticut's beautiful Quiet Corner, where peaceful country living meets modern comfort. Nestled on a quiet street in Killingly, CT, this well maintained 3-bedroom, 2.5-bath home sits on over half an acre of land, offering privacy, space, and a wonderful setting to enjoy all the area has to offer. Step inside to discover a thoughtfully designed floor plan featuring a formal living room, dining room, and a spacious family room just off the kitchen-the perfect gathering place for everyday living and entertaining. The family room offers brand new sliding doors out to the back deck. The house was recently fitted with brand new Anderson windows, new shower walls, 200 amp service, and professionally installed gutter leaf guards. Downstairs, the full basement includes a finished bonus room that offers endless possibilities as a home office, fitness room, craft studio, playroom, or media room. Designed with both convenience and sustainability in mind, this home features an attached two-car garage, energy-saving solar panels, and a Tesla backup battery system, providing increased efficiency and peace of mind during power outages. If you've been searching for a home that combines classic charm, modern updates, exceptional energy efficiency, and a peaceful setting, 40 Taft Street is ready to welcome you home.

40 Taft St, Killingly

$270,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193116 MLS

Welcome to this charming 3-bedroom, 2-bath Colonial offering 1,836 square feet of living space. Filled with character and potential, this home is ready for its next owner to make it their own. Whether you're looking for a primary residence or a great investment opportunity, this property offers endless possibilities. Conveniently located near downtown Putnam, you'll enjoy easy access to local restaurants, shopping, parks, and other everyday amenities. With public water and public sewer, the home offers added convenience and strong appeal for both homeowners and investors alike.

9 Hammond St, Putnam

$500,000

3 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24193333 MLS

Welcome to 17 Tripp Hollow Road in Brooklyn, Connecticut, where the charm of country living meets the comfort of a thoughtfully maintained home. Tucked away on a quiet scenic road, this Colonial, built in 2005, offers 2,100 square feet of living space with three bedrooms, two full bathrooms, one half bath, and an attached two-car garage. Step inside to discover a spacious, functional layout designed for both everyday living and entertaining. The home's inviting floor plan offers comfortable gathering spaces while providing the flexibility to accommodate a variety of needs. Whether you're hosting guests or enjoying a quiet evening at home, you'll appreciate the balance of space and warmth throughout. Outside, the beautifully landscaped grounds are a true highlight. Set on just under 1.8 acres, the property is accented by an impressive collection of established flowering plants that provide vibrant color from season to season. The expansive yard offers plenty of room for gardening, outdoor activities, or simply unwinding while taking in the peaceful surroundings and the privacy that makes this setting so special. Located just a short drive from local shopping, dining, schools, and other everyday conveniences, this property offers the opportunity to enjoy a quieter pace of life without sacrificing accessibility. Combining newer construction, a desirable layout, and exceptional value, 17 Tripp Hollow Road is ready for you.

17 Tripp Hollow Rd, Brooklyn

$850,000

5 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24176144 MLS

Welcome to your own retreat on more than 5 acres along 5 Mile River. Offering over 5,000 square feet of living space, this custom Colonial combines timeless craftsmanship with modern conveniences. The heart of the home is a chef's kitchen featuring granite countertops, a six-burner Viking gas range with integrated charbroiler, an eat-in dining area, and direct access to the backyard patio. The main level also includes a formal dining room, home office, first-floor laundry, and an impressive living room with soaring cathedral ceilings, hardwood floors, and a custom solid stone gas fireplace. The spacious first-floor primary suite features cathedral ceilings, custom wood-burning fireplace, a walk-in closet, spa-inspired bath with jetted tub, and private patio access. Upstairs is a second full bathroom and four generously sized bedrooms, one of which offers a walk-in closet. The finished space above the three-car garage provides exceptional space for entertaining, recreation, or guests. Conveniences include central air, an oil heating system that can be supplemented by an efficient whole-house wood-burning furnace, generator hookup, hot tub hookup, tanning bed hookup, and numerous smart home features including connected lighting, ceiling fans, Nest thermostat, automatic door locks, video doorbell integrated with the home's phone system, driveway sensor alerts, and bathroom humidity sensors.

56 River Rd, Killingly

$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

$349,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24191927 MLS

Move right into this beautifully refreshed Colonial, offering the perfect blend of comfort, space, and value! Featuring 3 bedrooms, 1.5 bathrooms and a finished basement, this home is ideal for first-time homebuyers, growing families, or anyone seeking extra room to live, work, and entertain. Recent updates include a new roof (approximately 3 years old), new flooring, and fresh interior paint, giving the home a clean, modern feel. The bright kitchen is equipped with stainless steel appliances and offers direct access to a rear a large deck overlooking the spacious backyard-perfect for summer barbecues, outdoor gatherings, or relaxing evenings. The finished basement with baseboard heat provides valuable additional living space, ideal for a family room, home office, gym, or playroom. Outside, you'll find a generous backyard with an above-ground pool that offers potential for restoration or removal based on the buyer's preference. Conveniently located near schools, shopping, restaurants, and major commuter routes, this move-in-ready home presents an exceptional opportunity to build equity and make lasting memories. Don't miss your chance to make this wonderful property your own! Sale contingent upon contract owners ability to take title (no title issues).

36 Labossiere Ln, Putnam

$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

$560,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24189241 MLS

Introducing this beautifully crafted 3-bedroom, 2.5 bath Colonial style home offering 1,872 square feet of thoughtfully designed living space set on a spacious 2 acre lot in Eastford, CT. Scheduled for occupancy in early summer, this is the perfect opportunity to secure new construction just in time for the 2026 summer months. This classical Colonial design blends timeless curb appeal with modern finishes. The open concept main level features hardwood flooring throughout the primary living areas and a bright, well appointed kitchen complete with center island, quartz countertops, and ample cabinetry, ideal for entertaining and everyday living. Bathrooms and laundry room feature durable ceramic tile, while plush carpeting provides comfort in all bedrooms. The spacious primary suite includes a private full bath and walk in closet creating a comfortable retreat. Built for year round efficiency and comfort, the home includes forced hot air powered by propane with central air conditioning. Exterior features include low-maintenance vinyl siding, asphalt shingle roof, a 24x24 attached garage, full basement offering future expansion potential, and composite deck perfect for outdoor enjoyment. Set on a generous 2 acre lot, this property provides privacy and space while maintaining convenient access to surrounding towns and amenities. Secure your new home now and move in just in time to enjoy summer in beautiful Eastford.

41 Weeks Rd W, Eastford

$499,900

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24189915 MLS

This beautifully crafted post-and-beam Saltbox home blends timeless character with modern functionality. 6.51 level acres! Designed with sustainability in mind, the home features solar power, well water, and an oil and wood burning furnace. With beautiful wide pine floors throughout, the open-concept living and dining area creates an inviting space for everyday living and entertaining, anchored by a cozy fireplace with wood stove perfect for winter evenings. The study on the main floor offers a quiet retreat with a convenient half bath that completes the first level. Upstairs, you'll find two comfortable bedrooms, each with its own fireplace, and a full bath, offering a peaceful and practical layout. The lower level offers a rec room, laundry room and full bath. This home features a large 24'x40' attached work shop ideal for a wood shop or art studio. Outside this property truly shines. Set back from the home is a 36'x24' barn suitable for 3 horse stalls or other animals, providing excellent flexibility for homesteading or equestrian use. This unique property offers space, craftsmanship, and versatility-perfect for those seeking a blend of rural charm, self-sufficiency, and thoughtful design. Located at the end of a quiet street, the property is bordered on three sides by a scout camp and is definitely a must see for those seeking privacy. Home could use some TLC but so much potential awaits! Possibly subdividable, buyer to do due diligence.

133 Fitts Rd, Ashford

$699,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191051 MLS

Welcome to this beautifully renovated home in desirable Pomfret CT! Offering the perfect blend of modern updates, flexible living space, and country charm, this impressive property is ready for its next owners. Inside, you'll find five spacious bedrooms and three full bathrooms, providing plenty of room for family, guests, or multi-generational living. The massive dining and flex space, offers endless possibilities for entertaining, hosting holiday gatherings, creating a home office, playroom, or additional living area. A convenient mudroom helps keep everyday life organized, and a large storage room provides abundant space for seasonal items, hobbies, and more. Comfort and efficiency are top priorities with mini-split systems throughout the home and a cozy pellet stove that creates a warm and inviting atmosphere during New England winters. Car enthusiasts, hobbyists, and those in need of extra workspace will appreciate the detached three-car garage with ample room for vehicles, equipment, and storage. Whether you're looking for room to grow, space to entertain, or a property with exceptional flexibility and future possibilities, this turnkey Pomfret home delivers it all. Don't miss your opportunity to own this rare offering in one of Northeastern Connecticuts most desirable communities.

250 Killingly Rd, Pomfret

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