Windsor Homes under $400,000

Welcome to Windsor, Connecticut—a charming town nestled in Hartford County, where history meets modern living. With its picturesque landscapes, vibrant community, and rich heritage, Windsor offers a delightful blend of suburban tranquility and urban convenience. Known for its beautiful parks, historic sites, and friendly neighborhoods, it’s no wonder that families, young professionals, and retirees alike are drawn to this welcoming enclave.

Windsor boasts a variety of homes that cater to diverse lifestyles, and the best part? You can find wonderful options available for under $400,000. Whether you’re searching for a cozy single-family home, a stylish townhouse, or a spacious condo, Windsor has something for everyone. These homes often feature charming architectural details, modern amenities, and lovely outdoor spaces, perfect for enjoying the beautiful New England seasons.

The town is also conveniently located near major highways and public transportation, making it easy to commute to nearby cities like Hartford and Springfield. Residents can enjoy a wealth of recreational opportunities, including walking trails, parks, and the scenic Connecticut River, all while being part of a close-knit community that hosts various events throughout the year.

With its affordable housing options and inviting atmosphere, Windsor is truly a hidden gem in Connecticut. If you’re looking to settle down in a place that offers both charm and convenience, explore the homes available in Windsor today and discover the perfect place to call home!

Newest Windsor Homes under $400,000

$235,000

3 Beds ⋅ 1 Baths ⋅ 24216610 MLS

Discover the potential at 17 Windbrook Drive in Windsor! This property presents an excellent investment opportunity for buyers looking to bring their vision to life and add value. Whether you're expanding your investment portfolio or searching for your next project, this is an opportunity worth exploring. Property is being sold AS IS. Schedule your private showing today!

17 Windbrook Dr, Windsor

$385,000

5 Beds ⋅ 5 Baths ⋅ 24216568 MLS

SPACIOUS COLONIAL WITH EXCEPTIONAL FLEXIBILITY & IN-LAW POTENTIAL! Set on a generously sized lot in convenient location, this expansive 2,812sf home offers a rare combination of size, versatility, & opportunity. Originally designed as a ranch & thoughtfully expanded w/substantial addition (1990's), the home features 5 bedrooms, 4.5 bathrooms, providing an abundance of living space easily accommodating multigenerational living, extended family, guests, home office needs, or potential in-law arrangement. Welcoming front entry opens to living room highlighted by hardwood floors & classic wood burning fireplace. Spacious kitchen w/large center island, ample cabinet & countertops, & new SS refrigerator. A screened porch provides a wonderful extension of living space. The main level features 2 bedrooms, multiple full baths, & expansive family room/living room addition that offer tremendous potential for a private guest suite, first floor primary bedroom living, or a future in-law setup. The upper level is devoted to retreats, including 3 additional bedrooms & a spacious primary suite, featuring new LVP flooring, ensuite full bath, & private balcony. Additional upper level bedrooms are generously proportioned & serviced by well-placed full bathrooms. Major capital improvements & infrastructure already in place including - Brand New Roof (2025), New Solar System (2025), updated 200-amp electrical system (2025), generator hookup, & natural gas boiler (2010). ***CONTINUED***

521 W Wolcott Ave, Windsor

$379,900

2 Beds ⋅ 2 Baths ⋅ 24215160 MLS ⋅ Walden Woods BLDG.

Welcome to 144 Morning Glory Court, a bright and beautifully maintained 2BR, 2BA condo offering 1,506 square feet of comfortable single-level living in the desirable Walden Woods community. Vacant and move-in ready, this inviting home is ready for its next owner! The open-concept living and dining area features soaring ceilings and expansive windows that fill the space with natural light, creating an airy and welcoming feel. The kitchen is conveniently located near the first-floor laundry and offers direct access to the spacious two-car garage. Step outside to enjoy brand-new, premium Trex deck overlooking a charming fenced-in garden area-a lovely spot for morning coffee, outdoor dining or simply unwinding at the end of the day. The spacious primary suite offers a peaceful retreat, with a large walk-in closet and private full bath featuring a separate soaking tub and walk-in shower. A second bedroom provides a comfortable space for guests, hobbies or home office. Downstairs, a partially finished basement offers flexible bonus space, ideal for a media room, workout room, home office, or additional storage. Enjoy the ease of low-maintenance living with The Walden Woods Association taking care of the exterior grounds and snow removal. The monthly HOA also covers landscaping, mulching, trimming and tree care.

144 Morning Glory Ct Unit 144, Windsor

$325,000

3 Beds ⋅ 2 Baths ⋅ 24211093 MLS

There's something about a New England Cape that makes coming home feel a little sweeter. Picture arriving after a busy day, setting your bags down, and letting the evening take shape at your own pace. Maybe dinner is a favorite recipe, maybe it's takeout and a movie, or maybe friends stop by and a quick visit turns into hours of good conversation. This three-bedroom, two-bath home in Windsor offers a place to settle into all of those everyday moments and make them your own. Mornings might begin with coffee and a few quiet minutes before the day gets moving. Weekends leave room for sleeping in, tackling a project, or heading out to explore Windsor before coming home to recharge. Three bedrooms give you options for how you live: a comfortable place to rest, room for overnight guests, or a dedicated space for working, creating, or pursuing whatever you love. Two bathrooms add convenience to daily routines, whether you're getting ready for the day or hosting company for the weekend. The appeal of Cape living is easy to imagine: familiar New England character, rooms made personal with all your favorite things, and a home that becomes part of your story over time. Think cozy evenings when the weather turns cool, a meal shared with people you love, and the satisfaction of having a place that feels like your own. Whether your next chapter calls for a fresh start, more flexibility, or simply a change of scenery, this Windsor Cape invites you to picture the life you could build here.

140 Matianuck Ave, Windsor

$279,000

3 Beds ⋅ 2 Baths ⋅ 24212833 MLS

Cozy three-bedroom ranch nestled on a quiet dead-end street in Windsor, offering added privacy and minimal through traffic. This inviting home features hardwood floors throughout, a private driveway with ample space for multiple vehicles, and a full basement with exterior access. The basement provides excellent potential for additional storage, a workshop, or future expansion. A comfortable and conveniently located home with plenty of opportunity to make it your own.

28 Nod Rd, Windsor

$329,900

3 Beds ⋅ 2 Baths ⋅ 24212093 MLS

CLASSIC COLONIAL LIVING W/THOUGHTFUL UPDATES & EXCEPTIONAL SETTING! Set against the open fields of Clover Street School & positioned on a level .26 acre lot, this 3 bedroom home offers approximately 2,130sf of comfortable living space. Inside, the home unfolds w/gracious living spaces that make a traditional colonial so enduring. The front-to-back living room features hardwood flooring & an abundance of natural light, while the dining room is distinguished by crown & wall molding. The kitchen has been refreshed w/new stainless steel range & refrigerator, & a charming sunroom provides a delightful transition to the outdoors, opening to the rear patio & a mature pear tree that produces fruit seasonally. A convenient half bath completes the main level. Upstairs, the primary bedroom offers a generous walk-in closet, accompanied by 2 additional bedrooms & a full bath. New luxury vinyl plank flooring enhances the stairs & upper level, w/original hardwood floors preserved beneath. The finished lower level adds remarkable flexibility, offering a recreation room w/dry bar, finished laundry area w/utility sink & built-in cabinetry, & extensive storage. Whether envisioned as a casual gathering space, home gym, office, or media room, it provides valuable additional living space. Outside, the paved driveway leads to a detached 1-car garage w/a generous carport overhang, providing covered parking or an inviting shaded setting for outdoor entertaining. ***CONTINUED***

37 Clover St, Windsor

$275,000

3 Beds ⋅ 2 Baths ⋅ 24210521 MLS

Nestled in Windsor, this inviting 3-bedroom, 2-full-bath home offers a wonderful opportunity to create a space that is distinctly your own. The home's comfortable living spaces provide the perfect backdrop for everyday living, entertaining, or simply relaxing at the end of the day. Three bedrooms offer flexibility for family, guests, a home office, or creative space, while two full bathrooms provide added convenience. Step outside from a deck off the kitchen and a fenced in yard and envision summer gatherings, gardening, playtime, or quiet mornings enjoying your own outdoor space. With room to personalize and add your own style, this home offers an exciting opportunity for buyers looking to create a space that feels uniquely theirs. Conveniently located in Windsor with access to shopping, dining, major routes, and the many amenities the area has to offer

110 Matianuck Ave, Windsor

$359,900

3 Beds ⋅ 2 Baths ⋅ 24208636 MLS

Welcome home to this charming split-level featuring 3 bedrooms and 1.5 bathrooms, beautifully situated on a manicured corner lot. From the driveway, step into a bright, welcoming family room (or office) filled with natural light. This versatile space offers built-ins, a huge closet, a cozy wood stove, and the added convenience of a half bath. The home offers generously sized, sun-filled bedrooms and beautiful wood floors throughout. You can also enter through the front door into the inviting L-shaped living and dining rooms, featuring a wood-burning fireplace and French doors that open to a heated sunroom - the perfect spot to relax, enjoy your morning coffee, or take in the views of the lovely yard. The kitchen features Corian countertops and stainless-steel appliances, offering both style and functionality. A two-car garage with a large workshop provides plenty of room for parking, hobbies, projects, and storage. Conveniently located close to Highway 91, shopping, restaurants, and the center of town, this home offers a wonderful combination of comfort, character, and convenience. Come see all it has to offer!

1128 Poqunock Ave, Windsor

$249,900

2 Beds ⋅ 3 Baths ⋅ 24206741 MLS ⋅ Chateau Woods BLDG.

Beautiful location,well maintained condo,walking distance for grocery store.Highway is very close.Ready to move in condition.

40 High Path Rd Unit 40, Windsor

$299,900

3 Beds ⋅ 3 Baths ⋅ 24209779 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

$299,900

2 Beds ⋅ 1 Baths ⋅ 24209540 MLS

Bright and sunny two-bedroom Cape style home with three season back covered porch, detached garage all on a pleasant level lot. Spacious living room with gleaming hardwood floors. sunny dining room With French door to the den. Large kitchen with 5 x 9 pantry. 2nd floor has 2 bedrooms and a full bath that has a 5-foot stall shower. The three-season porch is located in the back the home and has jalousie style windows. Fireplace in three season Rome is not functional at this time. Conveniently located only minutes from highways

19 Portman St, Windsor

$349,900

4 Beds ⋅ 2 Baths ⋅ 24209051 MLS

Step into timeless charm and classic New England character at this well maintained home on desirable Poquonock Avenue. Rich in historic appeal, this residence showcases architectural details that reflect Windsor's heritage while offering the comfort and functionality today's homeowners seek. Inside, you'll find beautiful hardwood floors flowing throughout the home, creating warmth, elegance, and a seamless feel from room to room. Natural light fills the inviting living spaces, highlighting the home's distinctive character and craftsmanship. Ideally located, this property offers convenient access to Windsor's many amenities, including parks, shopping, dining, schools, golf courses, and major commuter routes. Enjoy the charm of a neighborhood steeped in history while remaining just minutes from Bradley International Airport, downtown Hartford, and Windsor's vibrant town center. Whether you're relaxing at home or exploring everything the area has to offer, 1476 Poquannock Avenue provides a unique opportunity to own a home that beautifully blends historic character, an exceptional location, and timeless hardwood flooring throughout. Both attic and basement can be finished fully to give additional living space.

1476 Poquonock Ave, Windsor

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Windsor Homes under $400,000

Newest Windsor Homes under $400,000

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