Windsor City CT Real Estate, Homes, Condos for Sale

Not your grandmother's Cape. This one lives like a Colonial! In 2010 the upper floor was removed and replaced with two spectacular bedrooms, a sitting area and a full bath, all with level 8' ceilings. Plumbing and electrical systems were upgraded as part of that ambitious project. Central Air was added in 2018. On the main level, walls have been removed to create the sought-after Open Floorplan. The large, eat-in Kitchen opens to a Den, Full Bath and a first-floor Bedroom. An adjacent living room completes the plan. What was once a dingy lower-level space has been stripped and partially remodeled to create the potential for a great walk-out Rec Room, Work Shop. etc. The level back yard is enveloped in mature trees, creating a tranquil respite from the hectic world. The network of quiet streets in this neighborhood provides a great opportunity for walks or bike rides. Just a few blocks away, Deerfield Park offers a great playground and basketball court plus open fields for outdoor games. Nearby Stroh Park includes Goslee Pool, across from Windsor Shopping Center. This location provides easy access to I-91 and I-291 to get anywhere in CT. Just a couple miles away, you'll love to explore Windsor Center with a plethora of shopping, dining and entertainment venues. Schedule a visit soon before this one slips away.

76 Sinclair St, Windsor

$439,900

3 Beds ⋅ 3 Baths ⋅ 24178374 MLS

OFFER DEADLINE SUNDAY, 6/14 at 6PM. From the moment you pull up, the meticulous curb appeal sets the tone for the rest of your visit and exuding extreme pride of ownership. Tucked away on a quiet cul-de-sac, this home will check off every box! Inside, the open-concept main level is designed for real living - an eat-in kitchen with Electrolux appliances, granite countertops, and an island flows into a great room with vaulted ceilings and sliders to a brand-new Trex deck (2025 $20k). Share meals in the dining room, then step down to the front living room where a wood-burning fireplace makes it the natural spot to unwind at the end of the day. A half bath in the foyer completes the first floor. Upstairs, the primary suite offers a walk-in closet and renovated private bath. Two additional bedrooms and a skylit updated full bath complete the level. A new cooling system (2023 $20k) - central air upstairs, ductless on the main floor - keeps things comfortable year-round. The basement is already ahead of the game: two framed and carpeted rooms ready to become a home office, rec room, or gym. Out back, the oversized deck overlooks a park-like yard, ideal for entertaining, morning coffee, impromptu bocce tournament or just running and giggles. Windows, roof & slider replaced within the last 7 years. 1st floor hardwoods refinished in the last year. U'ground sprinklers in front & side yards. This one is as close to move-in, maintenance-free as it gets.

22 Pebblebrook, Windsor

$509,000

3 Beds ⋅ 3 Baths ⋅ 24176590 MLS

Welcome to 35 Hollow Brook Road, where space, privacy, and comfort come together in one of Windsor's most coveted and established neighborhoods. Set on a private 0.61-acre lot, this bright and well-maintained 4 bedroom, 3.5 bathroom Colonial offers almost 2100 sq. ft. of functional living space ideal for both everyday living and entertaining. Step inside to a sun-filled living room with gleaming hardwood floors and a cozy fireplace, flowing into a formal dining area, perfect for gatherings or quiet nights at home. The kitchen features a functional layout with stainless steel appliances. Upstairs, you'll find generously sized bedrooms, including a primary suite with a full bath, walk-in closet and fireplace. Hardwood flooring and abundant natural light throughout enhance the home's warm and inviting feel. Outside, the expansive backyard with a large in-ground pool creates the ultimate outdoor escape-ideal for summer entertaining, grilling on the patio, or relaxing by the firepit. Additional highlights include a generously sized attached 2 garage and ample off-street parking. Conveniently located just minutes from I-91, major highways, and close to Bradley International Airport, this home offers the perfect balance of privacy and commuter convenience, with nearby parks, trails, shopping, and dining nearby.

35 Hollow Brook Rd, Windsor

$425,000

4 Beds ⋅ 2 Baths ⋅ 24174583 MLS

Beautifully renovated 4-bedroom Cape offering the perfect blend of charm, comfort, and modern updates. This move-in ready home features an inviting open-concept floor plan with spacious living and dining areas, ideal for everyday living and entertaining. The stunning fully applianced kitchen has been tastefully updated with quartz countertops, new cabinetry, and modern finishes that flow seamlessly throughout the home. Relax year-round in the bright and airy sunroom overlooking the backyard, or enjoy cozy evenings by the gas-fired fireplace. The home also offers two beautifully renovated bathrooms, gas heat, vinyl siding, and numerous quality upgrades throughout. Step outside onto the spacious Trex deck, perfect for outdoor gatherings, grilling, or simply unwinding. Completing the property is an oversized detached 2-car garage offering ample storage and workspace possibilities. A truly turnkey property with style, functionality, and so much more to offer.

675 Palisado Ave, Windsor

$317,500

3 Beds ⋅ 3 Baths ⋅ 24174219 MLS

Opportunity knocks! This spacious colonial sits at the end of the cul-de-sac on a private wooded lot in an established neighborhood. Minutes to I-91, Bradley International Airport and all the amenities, yet set away from all the hustle and bustle. This home will need plenty of updates and work, but offers so much potential for just the right buyer! Personal property may remain. As-is.

18 Chelsea Ln, Windsor

$279,000

4 Beds ⋅ 2 Baths ⋅ 24173587 MLS

INVESTOR SPECIAL. Welcome to 120 Basswood Rd, a deceptively spacious home offering 2,441 sqft of flexibility and opportunity. This 4-bedroom, 2 full bath property features central air, solar panels for added efficiency, a two-car garage, and a fantastic backyard perfect for entertaining, summer BBQs, or simply relaxing. One of the home's standout features is the expansive bonus room, ideal for a movie theater, home office, playroom, media room, or additional living space. With generous room to grow and the opportunity to add your own personal touches, this home is packed with potential. Roof needs replacement. Basement is a dirt floor crawl space. CASH OR HARD MONEY PREFERRED!

120 Basswood Rd, Windsor

$650,000

3 Beds ⋅ 3 Baths ⋅ 24170111 MLS

Discover the perfect blend of comfort, convenience, and modern design in this stunning new construction Colonial set on nearly 1.5 acres in a peaceful Farming area. Ideally located near major highways and an international airport, this home offers effortless access to everything you need-just 30 minutes to Hartford, 20 minutes to Springfield, MA, 1.5 hours to Boston, and 2 hours to New York City. This thoughtfully designed 3-bedroom, 2.5-bath home features a spacious and functional layout with stylish finishes throughout. Enjoy luxury vinyl flooring across the main living areas, complemented by cozy carpeting in the bedrooms. The second-floor laundry room adds everyday convenience, while the attached two-car garage with automatic doors enhances ease of living. The kitchen comes fully equipped with all appliances included, opening to a bright dining area that leads out to a low-maintenance Trex deck-perfect for relaxing or entertaining. The home is also framed for a future fireplace insert in the family room, offering an opportunity to customize your living space. Built with efficiency in mind, this home includes propane gas heat, central air conditioning, and a hybrid hot water heater with a built-in dehumidifier. The basement is ready to be finished, and the home is already framed for a potential 4th bedroom, den, rec room & exercise room. Public water & septic system designed for four bedrooms add flexibility for future expansion. Enjoy tranquility of a private setting-

857 Stone Rd, Windsor

$339,000

4 Beds ⋅ 2 Baths ⋅ 24163643 MLS

Welcome to this spacious 4-bedroom, 2-bathroom Contemporary home on a cul-de-sac. The open floor plan includes over 2400 sq ft with a grand entrance view of the upper loft. Features include a primary bedroom suite with a walk-in closet, 1st floor and 2nd floor bedrooms, a large extra room with woodstove and slider leading to the private level back yard. Enjoy the CAir on these hot summer days. Newer hot water tank, updated electrical. Convenient to highways and shopping. Being sold "As Is".

39 Loren Cir, Windsor

$499,900

5 Beds ⋅ 3 Baths ⋅ 24163440 MLS

Space abounds!! Possible 6 or more bedrooms, possible 1st-floor bedroom. Possible in-law situation. Cul-de-sac location adjacent to a park in the center of town. Ample space! Home office, Game room, room to grow!3 fireplaces, a garden area. Needs some Love and Light.

30 Parkwood Dr, Windsor

$290,000

3 Beds ⋅ 2 Baths ⋅ 24162590 MLS

Welcome Home To This Lovely 1,472 Square Feet, 3 Bedroom, 1.5 Bath, Colonial House! Conveniently Located in A Peaceful Area Next To Parks, Several Hiking/Walking Trails Near the Connecticut River, A Nature Center, An Animal Barn, Highways, Libraries, Shopping, And Restaurants. This Well-Maintained Home Also Features Hardwood Floors Throughout, A Full-Size Deck, A Decent Sized Level Back Yard Great for Summertime Entertaining, Newer Boiler, New Roof, And More! Please Come See for Yourself!!!!!

28 Skitchewaug St, Windsor

$635,000

3 Beds ⋅ 3 Baths ⋅ 24156238 MLS

Imagine pulling into your driveway, greeted by open fields and the quiet charm of farmland - yet knowing you're just minutes from Bradley International Airport and major highways. Here, you can enjoy peaceful country living while staying under 30 minutes to Hartford and Springfield, and within two hours of Boston and New York City. Step inside the home you helped design, built by Fauteux Construction. The first floor welcomes you with crown molding details, a bright living room that could easily serve as a private office or den, and a warm family room anchored by a gas fireplace. The dining area flows effortlessly into an eat-in kitchen with a breakfast bar, where sliding glass doors frame views of your expansive backyard. Just beyond, a two-car garage connects conveniently to the kitchen for everyday ease. Upstairs, all bedrooms are thoughtfully placed for privacy, along with a centrally located laundry closet that simplifies daily routines. Tiled bathrooms, beautiful finishes, and the opportunity to select your own flooring, colors, and materials allow you to create a home that truly reflects your style. You may even bring your own plans for consideration, ensuring every detail fits your vision. This is more than new construction - it's your chance to build a custom home in a setting that offers rural serenity without sacrificing location or convenience. Lead time is approximately six months from time of contract. Your plans or builders~ Finally, get what you want!

823 Stone Rd, Windsor

$729,000

4 Beds ⋅ 3 Baths ⋅ 24156249 MLS

Imagine pulling into your driveway, greeted by open fields and the quiet charm of farmland - yet knowing you're just minutes from Bradley International Airport and major highways. Here, you can enjoy peaceful country living while staying under 30 minutes to Hartford and Springfield, and within two hours of Boston and New York City. Step inside the home you helped design, built by Fauteux Construction. The first floor welcomes you with crown molding details, a bright living room that could easily serve as a private office or den, and a warm family room anchored by a gas fireplace. The dining area flows effortlessly into an eat-in kitchen with a breakfast bar, where sliding glass doors frame views of your expansive backyard. Just beyond, a two-car garage connects conveniently to the kitchen for everyday ease. Upstairs, all bedrooms are thoughtfully placed for privacy, along with a centrally located laundry closet that simplifies daily routines. Tiled bathrooms, beautiful finishes, and the opportunity to select your own flooring, colors, and materials allow you to create a home that truly reflects your style. You may even bring your own plans for consideration, ensuring every detail fits your vision. This is more than new construction - it's your chance to build a custom home in a setting that offers rural serenity without sacrificing location or convenience. Lead time is approximately six months from time of contract. Your plans or builders~ Finally, get what you want!

823a Stone Rd, Windsor

$599,900

3 Beds ⋅ 3 Baths ⋅ 24154187 MLS

**TO BE BUILT**Fabulous Hopscotch Model New Construction offering a flexible, Open Floor Plan with Modern Finishes throughout. Enjoy 2,160 SF of living space with additional 560 SF of finished lower-level family room or office space-perfect for work-from-home, a media room, or extra living area. The Kitchen features Granite Countertops, a Center Island, Pantry, and Stainless-steel appliances, opening seamlessly to the Living and Dining areas for easy entertaining. You'll also love the convenient mudroom entry from the garage, a main-level laundry room with half bath, and a dedicated study/office on the first floor open or can be separate room if desired. Upstairs, the spacious Primary Suite includes a walk-in closet and full bath, along with two additional Bedrooms and a full main bath. There's also room for future expansion-add a primary suite over the garage for the potential of 4 bedrooms and 2.5 or 3.5 baths. Highlights include great cabinet choices with soft-close hinges, full-extension drawers, Modern Lighting and Flooring, Granite in the Kitchen and Baths, Central air, Architectural roof, and Thermopane tilt-in Windows, 200Amp Electrical, plus a welcoming Covered Front Porch. A Great Opportunity under $600K-don't wait!

318 Capen St, Windsor

$265,000

24152589 MLS

This 13.3 acre property consists of high-quality farmland that has naturally regenerated into a forest of white pine and mixed hardwoods. The land was originally created as 16 individual lots as part of an adjacent subdivision that was never completed and has since been combined into one contiguous parcel. Most of the property is now zoned Agricultural, with a few acres at the north end remaining in the R-10 Residential District, and it lies within the Agricultural District, which allows for one single-family residence, barns, and structures supporting agricultural uses. Electric service is available at the street, while water and septic systems are private. The property is conveniently located near Bradley International Airport, and the paper roads originally planned to serve the subdivision were never constructed. The underlying soils are Windsor Loamy Sand (0-3 per cent slopes), a highly regarded agricultural soil type known for excellent drainage and suitability for high-value crops, including wrapper-grade tobacco, making this property particularly attractive for agricultural use, homesteading, or long-term investment.

Walnut And Larch Dr, Windsor

$500,000

4 Beds ⋅ 5 Baths ⋅ 24145144 MLS

4 bedroom, 4.5 bathrooms. 3 bedrooms on 2nd floor and 1 bedroom (Den) with full bathroom on main floor for convenience. Large Family room with French doors leading into the kitchen. Formal dining and formal living room. Bedroom/Den has a fireplace. Basement partially finished with a completely finished bathroom. Situated on Large pool-size lot with Storage Shed.

123 Country Club Dr, Windsor

$400,000

3 Beds ⋅ 4 Baths ⋅ 24132692 MLS

Back on Market! Tucked away on a quiet cul-de-sac, this expansive contemporary home offers incredible potential. Featuring a spacious layout, soaring ceilings, and an abundance of natural light, the property boasts strong bones and a flexible floor plan ready for your vision. Whether you're looking to modernize, renovate, or create your dream home, the possibilities here are truly endless. A rare opportunity to bring new life to a substantial home in a desirable Windsor location. UPDATE: Multiple offers, Highest and Best to be called Thursday. 3/26/2026 by 5:00pm

1 Deanne Lynn Cir, Windsor

$325,000

24101408 MLS

Attention Farmers!! This 12+ acre location is strictly for the farmers. With a tobacco barn and newly updated potato barn this piece of property is ready for you to start your farming business. Agents please reach out for the specific guidelines with this property or read the agent notes

490 Old Day Hill Rd, Windsor

$1,900,000

24099936 MLS

There are two abutting parcels that offer a total of 79 acres. 999 Stone Road is a 56.7 acre parcel that is zoned Agricultural. 965 Stone Road is a 22.3 acre parcel that is zoned Industrial. The parcels are level and wooded with some open areas. The two parcels combined offer an opportunity for Industrial, Agricultural or potential Residential development. This very convenient location is just minutes away from Bradley International Airport, Route 20 and I-91.

999 Stone Rd, Windsor

$449,000

3 Beds ⋅ 3 Baths ⋅ 24098749 MLS

PRICED TO SELL: MAJOR DISCOUNT & FLEXIBLE PRICING! Seller is relocating out of state and wants a FAST closing! A great deal on a HEALTHY home. Key Features and Upgrades: -Solid and Move-In Ready: Roof has 15+ years of life remaining, heating system recently serviced, and all appliances in great condition. -Energy Efficient and Secure: Solar panels with backup solar generator, real-time monitored water and electricity usage, and security cameras. -Spacious and Bright: High ceilings, two grand bay windows, and all-carpet flooring (friendly for little ones). -Upgraded Kitchen: Powerful 800 CFM exhaust fan. -Ample Storage: Custom shelving in garage (without sacrificing parking). Location Location and Location, that is the only thing you won't be able to change: * Exceptionally low radon levels (0.16 pCi/L long-term average) , rare in CT! * Continuous monitoring for 26 years confirms safety for your family, esp the little ones!

58 Amanda Cir, Windsor

Browse All Windsor City CT Properties for Sale

Windsor City Real Estate