Windsor Real Estate

Welcome to Windsor, Connecticut – a charming town steeped in history and brimming with vibrant community spirit. Nestled in Hartford County, Windsor is the second oldest town in Connecticut, founded in 1633. Its rich heritage is beautifully reflected in the well-preserved architecture and historical sites that dot the landscape, including the famed Windsor Historical Society and the elegant Palisado Green.

Windsor offers a unique blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike. With its picturesque parks, such as the scenic Northwest Park, residents can enjoy outdoor activities ranging from hiking and biking to picnicking amidst nature's beauty. The town's commitment to green spaces fosters a strong sense of community, where neighbors gather for seasonal events and festivals that celebrate local culture.

Conveniently located just a short drive from Hartford, Windsor provides easy access to a wealth of amenities, including shopping, dining, and entertainment options. The local school system is highly regarded, ensuring that families have access to quality education for their children. Additionally, the town's proximity to major highways and the Bradley International Airport makes commuting a breeze.

Whether you're exploring the quaint downtown area filled with charming shops or enjoying a leisurely stroll along the Connecticut River, Windsor embodies the perfect balance of historic charm and modern convenience. Discover the warmth of this inviting community, and see why so many are proud to call Windsor home. Your dream home awaits in this delightful town!

Newest Listings in Windsor

$349,900

3 Beds ⋅ 3 Baths ⋅ 24195542 MLS

Welcome home to a beautifully maintained raised ranch offering the perfect blend of comfort and versatility in Windsor. This 3-bedroom, 2.5-bath home features a layout built for easy everyday living and awaits your final touches. Open floor concept which is perfect for quiet nights in or hosting guests. Looking for more space? The fully finished basement is ready for whatever you need - media room, home gym, or playroom, the choice is yours. Out back, an oversized, cleared, and fenced yard sets the stage for summer entertaining. The home is equipped with oil heat and solar panels to help offset electric costs. Located in the Windsor Public Schools district, known for its impressive 10:1 student-teacher ratio, 67 Sunnyfield also puts you close to Northwest Park, Windsor Meadows State Park, and Keney Golf Course, plus convenient shopping, medical facilities, and the library. Commuters will appreciate quick access to Route 218, I-91, and Bradley International Airport. Schedule your showing today!

67 Sunnyfield Dr, Windsor

$449,000

4 Beds ⋅ 3 Baths ⋅ 24193537 MLS

Welcome to this spacious 4-bedroom, 21/2-bath Colonial located in one of Windsor's established neighborhoods. Offering generous living space, a functional floor plan, and solid bones, this home presents an excellent opportunity for buyers looking to add their own personal style and updates. The main level features a welcoming foyer, a bright living room, formal dining room, a spacious eat-in kitchen, and a comfortable family room that's perfect for everyday living or entertaining. Upstairs, you'll find four generously sized bedrooms, including a primary suite with a private full bath, along with ample closet space throughout. Outside, enjoy a private backyard with plenty of room for outdoor gatherings, gardening, or simply relaxing. An attached two-car garage and full basement provide additional storage and endless possibilities. While the home would benefit from cosmetic updates such as fresh paint, flooring, and modern finishes, it has been well maintained and offers a fantastic opportunity to build equity in a highly desirable Windsor location. Conveniently located near parks, schools, shopping, restaurants, Bradley International Airport, and major highways, this home combines space, location, and value.

46 Lincoln Way, Windsor

$389,900

3 Beds ⋅ 2 Baths ⋅ 24195772 MLS

Welcome home to 437 W.Wolcott. This lovely raised ranch, has been proudly owned by the same family for over 30 years. This charming 3-bedroom, 2-bath home offers warmth and character throughout, featuring beautiful hardwood floors, two cozy fireplaces, and a timeless brick exterior. The inviting layout provides comfortable living spaces perfect for everyday living and entertaining. Step outside to enjoy the spacious deck overlooking a lovely backyard, ideal for relaxing or hosting family and friends. Complete with a 2-car garage and located in a desirable Windsor neighborhood, this home is ready for its next chapter. Don't miss the opportunity to make this well-cared-for property your own!

437 W Wolcott Ave, Windsor

$524,900

3 Beds ⋅ 3 Baths ⋅ 24194078 MLS

Welcome to 22 Settler Circle, this one is sure to impress, the moment you walk in you are welcomed with a warmth living room with a built in fireplace and an amazing spacious kitchen that has been totally redone with new cabinets, countertops , appliances and back splash. Other features includes a brand new deck with mahogany deck boards and PVC railings, central air is sure to be a plus on those hot summer days. New LVP flooring throughout, new lighting and freshly painted throughout.

22 Settler Cir, Windsor

$199,000

2 Beds ⋅ 2 Baths ⋅ 24195154 MLS ⋅ Valley Village BLDG.

Welcome to this well-maintained townhouse-style condominium offering the perfect combination of comfort, convenience, and low-maintenance living. This inviting home features 2 spacious bedrooms, 1 full bath, and 1 half bath, with a functional multi-level layout that provides privacy and separation of living spaces. The bright upper level offers two generously sized bedrooms, each with ample closet space, and a full bathroom. The main living area is warm and welcoming, with easy access to your private patio-an ideal spot for relaxing or entertaining. This home also offers the convenience of an attached one-car garage with an additional assigned parking space directly in front. The furnace was recently replaced along with newer windows, doors and roof.

318 Dunfey Ln Unit 318, Windsor

$419,900

3 Beds ⋅ 3 Baths ⋅ 24195432 MLS

Completely renovated and move-in ready! This stunning 3-bedroom, 2.5-bath raised ranch in Windsor has been thoughtfully updated from top to bottom and offers the perfect blend of modern style and everyday comfort. Step inside to a bright, open-concept main level featuring soaring vaulted ceilings, luxury vinyl plank flooring, and an expansive living and dining area centered around a beautiful brick fireplace. The show-stopping kitchen is designed for both entertaining and daily living, boasting an oversized center island, quartz countertops, custom cabinetry, subway tile backsplash, and stainless steel appliances. Sliding doors lead to the rear deck, making indoor-outdoor gatherings a breeze. The spacious primary suite offers a beautifully updated private bath, while two additional bedrooms and a renovated full bath complete the main level. Downstairs, enjoy a large finished family room with a second brick fireplace, a convenient half bath, and direct access to the attached two-car garage. Situated on a private, tree-lined lot, this home delivers the perfect balance of peaceful surroundings and everyday convenience, with easy access to shopping, dining, parks, schools, and major commuter routes. Every detail has been refreshed, allowing you to simply unpack and enjoy. Don't miss your opportunity to own this turnkey Windsor gem!

99 Pepperbush Way, Windsor

$529,900

4 Beds ⋅ 4 Baths ⋅ 24195383 MLS

Highest and Best Due by 08/02/2026 @ 6pm. SELLER PREFERS ALL OFFERS ON GHAR CONTRACTS ONLY. Welcome to 1 Walters Way, a one-of-a-kind CUSTOM-BUILT, nestled on 2.19 private acres with 95,396 lot sq ft in one of Windsor's most desirable neighborhoods. Beautifully designed and built in 2010 by the current owner's father, this one-owner home reflects pride of ownership, timeless craftsmanship, and lasting quality throughout. Competitively priced, this is a rare opportunity to own a beautiful home with exceptional character and endless potential. From the striking stone facade and grand arched entry to the sun-filled interior, you'll find hardwood floors, elegant archways, and spacious living areas designed for everyday living and entertaining. The open-concept kitchen flows seamlessly into the seating area, while the formal dining room is perfect for gatherings. The expansive primary suite offers a fireplace, sitting area, and spa-inspired bath. Three additional bedrooms provide flexibility for family, guests, or a home office. The unfinished walkout lower level offers incredible potential for a home theater, gym, recreation room, or in-law suite. Conveniently located just minutes from Windsor Center, commuter routes, parks, and the Connecticut River Boat Launch, this home offers privacy, space, and a story all its own. Come experience the warmth, craftsmanship, and opportunity that make 1 Walters Way truly unforgettable.

1 Walters Way, Windsor

$329,900

3 Beds ⋅ 3 Baths ⋅ 24194859 MLS

WELCOME HOME! This 3 Bedroom 2.5 bath Ranch is ready for its new owner. This is the ultimate turn key property. The only thing that it requires is your finishing touch. 1008 N. Worthy has been updated literally from top to bottom. On the exterior, there is a new roof, new windows, new doors, new front steps and new hand railings. The entire interior has new flooring and has been freshly painted. The kitchen is equipped with recess lighting, stainless steel appliances, granite counter tops and new cabinetry. The primary bedroom can accommodate large furniture and has a fully renovated bath attached. The second full bath is also fully renovated and offers a tub and shower option. The basement is partially finished. The walls are freshly painted and there is a half bath for your convenience. There is a new oil tank and furnace in place. The back yard is level and has plenty of potential. There are also new bulkhead doors that lead to the basement. This home is a must see. Schedule your showing today.

1008 N Worthy St, Windsor

$250,000

2 Beds ⋅ 3 Baths ⋅ 24194889 MLS ⋅ Dunfey Lane,Valley Village BLDG.

Welcome to this beautifully updated townhouse offering 2 bedrooms, 2.5 baths, and the perfect blend of comfort and convenience. The bright, inviting layout features spacious living areas and a partially finished basement adding approximately 150 square feet of versatile space-ideal for a family room, home office, gym, or playroom. Major mechanical updates provide peace of mind, including a new furnace & central air conditioning (2014) and water heater(2023). With generous bedrooms, ample storage, and low-maintenance living, this home is move-in ready and designed for today's lifestyle. Conveniently located in Windsor with easy access to I-91, Bradley International Airport, Hartford, shopping, restaurants, and everyday amenities, commuting is a breeze. Outdoor enthusiasts will enjoy nearby Northwest Park, the Farmington River, and Windsor's scenic parks and walking trails, while Windsor Center offers local dining, shops, community events, and the historic town green. Whether you're a first-time buyer, downsizing, or looking for a home with flexible living space in a prime location, this well-maintained property checks all the boxes. Don't miss this opportunity to enjoy comfortable condo living with modern updates and an unbeatable location.

323 Dunfey Ln Unit 323, Windsor

$275,000

3 Beds ⋅ 2 Baths ⋅ 24192993 MLS

Welcome to 15 Bina Avenue! Offering 1,150 square feet of endless potential, this Windsor home is a exceptional opportunity for buyers or investors looking to customize, add updates, and build immediate equity. The main level features a functional living layout with great natural light and effortless flow. Upstairs, you will find three bedrooms complete with original hardwood floors and 1.5 bathrooms. The full basement provides excellent additional storage or potential for future finished space, while the detached 2-car garage offers ample room for vehicles, extra storage, or a workshop. Conveniently located in a quiet Windsor neighborhood with quick access to local shopping, dining, parks, and major highways for an easy commute. Bring your design ideas and make this property your own-schedule your showing today!

15 Bina Ave, Windsor

$449,900

4 Beds ⋅ 3 Baths ⋅ 24193773 MLS

Nestled in a quiet neighborhood, this spacious 4-bedroom, 2.5-bath home offers the perfect blend of comfort, character, and opportunity. Freshly painted throughout, this home is a blank slate ready for its next owner to make it their own. The inviting floor plan features hardwood floors, a dramatic vaulted-ceiling living room, and a large rec room with exposed wood beams and a beautiful Vermont soapstone wood stove, creating a warm and welcoming space for relaxing or entertaining. The primary suite includes a private en suite bath, while the flexible layout provides plenty of room for family, guests, or a home office. The finished lower level offers even more space to fit your needs. Step outside to a large deck with a pergola overlooking a picturesque backyard complete with a peaceful brook and a large storage shed, offering the perfect setting to enjoy nature and outdoor gatherings. Additional highlights include a full-house propane generator, newer roof (approximately 2 to 3 years old), newer central air conditioning, a two-car garage, and a recently resealed driveway. With generous living space, a desirable location, and endless possibilities to personalize, this is a wonderful opportunity to create the home you've always envisioned.

40 Eastview Dr, Windsor

$425,000

5 Beds ⋅ 2 Baths ⋅ 24192829 MLS

Open house schedule- 7/31: 4pm-7pm. & 8/1: 11am-2pm Windsor's finest ! This amazing 2 family is the perfect property for investors or owner occupants! Featuring 3 bedrooms and 1 bathroom on the first floor and 2 bedrooms and 1 bathroom on the second floor. Can easily maximize your cash flow. Remodeled units throughout. Newer gas heating systems, Newer Roof, Newer Siding, electrical and windows as well. Spacious basement can be used for additional living space. Plenty of storage and closet space. On and off street parking. Easy access to bus lines, parks and restaurants. Come check this property out!

23 Lyme St, Windsor

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