Windham County Real Estate

Welcome to Windham County, Connecticut – a hidden gem nestled in the heart of New England! Known for its rich history, vibrant communities, and stunning natural landscapes, Windham County offers a unique blend of rural charm and modern conveniences, making it an ideal place to call home.

With its picturesque towns such as Willimantic, Putnam, and Killingly, Windham County boasts a variety of attractions for residents and visitors alike. The area is steeped in history, featuring beautifully preserved architecture, quaint Main Streets lined with local shops, and a thriving arts scene. Explore the historic Willimantic Thread Mill, once a hub of textile production, or take a stroll through the charming parks and riverfront areas that showcase the county's natural beauty.

Outdoor enthusiasts will find plenty to love in Windham County. With numerous hiking trails, state parks, and recreational areas, including the scenic Mansfield Hollow State Park and the serene Natchaug State Forest, adventure awaits at every turn. Whether you enjoy hiking, biking, or simply soaking in the beauty of nature, this county offers endless opportunities for exploration.

Windham County is also home to a range of educational institutions, including Eastern Connecticut State University, which adds to the vibrant, youthful atmosphere of the area. The community is known for its friendly residents, making it easy to feel at home here.

Whether you’re looking for a cozy cottage, a spacious family home, or a charming historic property, Windham County has something for everyone. Come discover the warmth and charm of Windham County, where your dream home awaits!

Newest Listings in Windham County

$289,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24194880 MLS

Pride of ownership shines throughout this beautifully updated 3-bedroom, 1.1 bath ranch, ideally situated in a convenient neighborhood setting. The bright, freshly painted interior features gleaming hardwood floors, newer carpeting in all three bedrooms, freshly painted doors with updated hardware, custom window treatments, and stylish new lighting throughout. The updated kitchen offers newer tile flooring, refreshed countertops, a double sink, stainless steel appliances, plus a brand-new dishwasher and range hood (July 2026), making it as functional as it is attractive. Major improvements provide peace of mind, including a new roof (October 2024), central air conditioning, newer windows, and newer gutters with leaf guards. The heated lower level adds approximately 575 square feet of finished living space and includes a convenient half bath, creating the perfect space for a family room, home office, guest area, recreation room, or flexible everyday living. A separate laundry area is equipped with a newer washer and dryer. Step outside to enjoy a private backyard bordered by mature woods, offering a peaceful retreat for relaxing or entertaining. A storage shed provides additional space for lawn equipment, gardening tools, and seasonal storage, adding even more functionality to the property. Conveniently located near Routes 6 and 32, this home provides easy access to UConn, Eastern Connecticut State University, shopping, dining, and a variety of everyday amenities.

143 Southridge Dr, Windham

$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

$350,000

3 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24168798 MLS

Move right into this well-maintained 3-bedroom, 1-bath ranch in the heart of Canterbury! Offering a total of 1,764 sq. ft. per town records (1008 up and 756 in lower level), this home features beautiful flooring on main level, fresh interior paint, and a spacious, well-kept kitchen with abundant cabinet storage. All kitchen appliances were replaced in July 2025. 3 standard size bedrooms and an updated full bath complete the main level. The finished lower level provides 2 flex spaces perfect for a home office, gym, playroom, or guest area, plus a pantry/storage closet. You'll also find the laundry area, a furnace installed in 2022, and an additional refrigerator and shelving that will remain with the home. A French drain system was professionally installed around the home to keep the basement dry. Additional highlights include central air, a whole-house generator installed in 2024, a roof approximately 10-11 years old, new storm doors added in 2022 (front) and 2024 (side), and a beautifully constructed retaining wall that enhances the home's curb appeal. The basement features durable concrete floors, offering the opportunity to customize with your preferred flooring. Situated on a level 0.66-acre lot, this property also includes leased solar installed in 2016 with a 20-year PPA. The seller currently pays an average of approximately $160/month for solar plus $23.75/month to Eversource. This move-in ready home has been very well maintained.

38 Ayers Dr, Canterbury

$399,900

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24195054 MLS

Welcome home to this beautiful, move-in ready Cape Cod nestled on a peaceful 1.80-acre lot. This charming home offers 3 bedrooms and 2 full bathrooms with a bright, open floor plan that seamlessly connects the kitchen, dining area, and living room-perfect for everyday living and entertaining. The spacious living room features vaulted ceilings and a cozy wood-burning stove, creating the perfect gathering space on chilly New England evenings. The main level also includes a convenient laundry area, a full bathroom, and one bedroom, offering flexible living options. Upstairs, you'll find the primary bedroom, a third bedroom, and the second full bathroom, providing privacy and comfort. Step outside to enjoy the brand-new composite deck overlooking the peaceful backyard, along with a new storage shed for all your outdoor equipment. The roof is only two years old, giving you added peace of mind. Don't miss your opportunity to own this well-maintained home that combines comfort, charm, and a serene country setting.

49 Parsonage Rd, Hampton

$699,900

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24189180 MLS

Step back in time while enjoying the comforts of today at this remarkable circa-1770 property, where timeless New England charm meets modern convenience. Set on nearly 4 private acres, this one-of-a-kind estate offers endless possibilities for multi-generational living, rental income, a hobby farm, or the perfect retreat. The beautifully maintained main residence showcases the character and craftsmanship of the 18th century while benefiting from numerous thoughtful renovations and updates throughout. An attached apartment provides excellent flexibility for extended family, guests, or additional income potential. Adding even more value, a separate building on the property offers additional living or occupancy opportunities, making this an exceptional property for those seeking space and versatility. Outside, you'll find an impressive collection of amenities including your own private dock, multiple garage spaces, several outbuildings, and charming sheds that are ideal for entertaining, gatherings, workshops, or creative spaces. The expansive grounds offer room to relax, garden, explore, and enjoy the peaceful surroundings. Whether you're searching for a unique historic home, an investment opportunity, or a private country estate with endless possibilities, this extraordinary property is truly unlike anything else on the market.

1530 Hartford Pike, Killingly

$529,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194850 MLS

Tucked away in desirable East Putnam in a park-like setting, this beautifully maintained split-level home offers 2,197 square feet of thoughtfully designed living space.The main level welcomes you with a spacious living room centered around a cozy gas fireplace, creating the perfect gathering space. The dining room flows into the well-appointed kitchen featuring a distinctive hammered copper sink, & an oversized pantry for exceptional storage. A full bath and large coat closet add convenience to the main floor. The stunning four-season sunroom is sure to become your favorite room in the house. Featuring French doors, tongue-and-groove ceilings, wide pine floors, abundant natural light, and sliding doors leading outside, this inviting space offers seamless indoor-outdoor living throughout the year. The upper level features a spacious primary complete with custom built-in bookshelves, a mini-split system for efficient air conditioning, and a remodeled bath (2013) offering double sinks, tile flooring, and conveniently located laundry. Two additional bedrooms complete the upper level.The lower level provides outstanding flexibility with a dedicated office, additional bonus room, and large workshop for the hobbyist. Plus, an abundance of storage space. Step outside to enjoy professionally landscaped grounds highlighted by a tranquil koi pond, beautiful stone walls, perennial gardens, creating a picturesque outdoor setting with plenty of room to garden, relax, or entertain.

39 Fox Rd, Putnam

$599,999

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24194870 MLS

Offered for the first time, this lovingly maintained one-owner Cape is nestled in a peaceful country setting surrounded by mature trees and natural beauty. Built in 2003, this spacious home offers 2700 square feet. The main level features a private primary suite with its own deck, oversized walk-in closet/dressing room, and ensuite bath with soaking tub and separate shower. The inviting layout flows from the foyer to the living room, formal dining room, and eat-in kitchen with peninsula seating. A first-floor laundry room includes a small office and additional storage. Upstairs, two generously sized bedrooms share a Jack-and-Jill bath. One bedroom features a large walk-in closet, while the other offers two walk-in closets for exceptional storage. The attached three-bay garage provides interior access to unfinished space above, offering excellent potential for a home office, recreation room, or guest suite. Outside, enjoy a welcoming wraparound farmer's porch, rear deck overlooking the tranquil backyard, and a convenient storage shed. With just a few cosmetic updates, this well-built home offers a wonderful opportunity to add your personal style while enjoying the peace and privacy of country living.

109 Starkweather Rd, Plainfield

$349,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24194783 MLS

Built in 2006, this 3-bedroom Cape offers an excellent opportunity to own a well-designed home on a quiet residential street in Brooklyn. The spacious second-floor bedrooms provide more room than many homes of this style, while the functional floor plan makes everyday living comfortable and practical. Recent updates include replacement flooring throughout much of the home, and the full Partially finished basement offers great potential for additional living space. With public water and sewer, a manageable yard, and convenient access to schools, shopping, restaurants, and major commuting routes, this home is well suited for first-time buyers, downsizers, or anyone looking for an affordable home with the opportunity to add value over time. Eligible for FHA, VA, USDA, and conventional financing, this home offers a great combination of affordability, potential, and location. Schedule your private showing today!

10 Russell Ave, Brooklyn

$265,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24194523 MLS

Check out this home with great potential! With a little vision and sweat equity this house could be transformed into the home of your dreams. The backyard is spacious, private, and ready for you to relax in. Subject to probate court approval.

39 Sterling Hill Rd, Plainfield

$330,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24194578 MLS

Don't miss this adorable, move-in-ready ranch! Offering just over 1,200 square feet of comfortable living space, this charming two-bedroom home features an inviting open floor plan filled with natural light and hardwood floors throughout much of the home. The spacious layout is perfect for everyday living and entertaining alike. Step outside to a generous backyard with a deck, ideal for summer barbecues, relaxing, or enjoying your morning coffee. A newer roof provides added peace of mind, while the attached garage adds everyday convenience. This home is also equipped with solar, providing added energy efficiency and the potential for long-term utility savings. Combining charm, comfort, and a fantastic location close to shopping, dining, parks, and major commuter routes, this home is ready for its next owner to move in and make it their own!

517 Davis Rd, Killingly

$439,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194589 MLS

Welcome to country living at its finest! Nestled on 5.16 private acres, this impeccably maintained custom ranch offers the perfect blend of comfort, quality, and timeless appeal. Built in 2001, this move-in ready home features 1,582 square feet of thoughtfully designed one-level living with gleaming hardwood floors, central air, first-floor laundry, and an attached two-car garage. The spacious kitchen is the heart of the home, boasting granite countertops, abundant cabinetry, a breakfast bar, and an open layout overlooking the dining area with sliders leading outside. Entertain with ease in the formal dining room or unwind in the living room, filled with natural light. The generous primary suite and second bedroom are complemented by two full baths, while the existing three-bedroom septic system offers valuable flexibility for future expansion. Surrounded by mature trees and beautifully maintained grounds, this property provides exceptional privacy without sacrificing convenience. Every room reflects true pride of ownership, making this a rare opportunity to own a meticulously cared-for home where quality, tranquility, and country charm come together.

313 Lisbon Rd, Canterbury

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