Windsor Real Estate

Welcome to Windsor, Connecticut—a charming town nestled in Hartford County that beautifully blends rich history with modern living. Established in 1633, Windsor is one of the oldest towns in the state, steeped in colonial heritage and vibrant community spirit. With its picturesque landscapes, scenic parks, and inviting neighborhoods, Windsor offers a serene escape while being conveniently located just a short drive from the bustling city of Hartford.

Windsor boasts a variety of outdoor recreational opportunities, including the stunning Northwest Park, which features walking trails, picnic areas, and a beautiful nature center. For those who enjoy water activities, the Connecticut River offers kayaking, fishing, and breathtaking views. The town is also home to several historical landmarks, such as the Windsor Historical Society and the Oliver Ellsworth Homestead, where you can immerse yourself in the rich tapestry of the town’s past.

The community is known for its excellent schools, making it an ideal place for families. Windsor’s diverse neighborhoods cater to a range of lifestyles, from charming historic homes to contemporary developments. Residents enjoy a close-knit community feel, with local events, farmers' markets, and seasonal festivals that bring everyone together.

With its unique blend of history, culture, and natural beauty, Windsor is not just a place to live—it's a place to thrive. Whether you're looking for your first home or seeking to relocate, Windsor offers a welcoming atmosphere and a promising future. Come discover the charm of Windsor, where every corner tells a story and every day feels like home.

Newest Listings in Windsor

$340,000

24216875 MLS

# PRIME DEVELOPMENT OPPORTUNITY ## 459 Windsor Avenue, Windsor, Connecticut **Approximately 2 Acres | Mixed-Use Residential & Commercial Development** An exceptional development and investment opportunity featuring approximately **2 acres of land** strategically located at 459 Windsor Avenue in Windsor, Connecticut. The property offers significant flexibility for a variety of residential, commercial, retail, hospitality, and entertainment uses. Its mixed-use development potential makes it an attractive opportunity for investors and developers seeking to capitalize on the demand for housing, retail, and commercial space in the Greater Hartford area. ### Potential Development Uses - **Mixed-Use Residential & Retail:** Ground-floor retail or commercial space with up to 40 residential apartment units on the upper floors. - **Retail Shopping Center:** Retail stores, storefronts, neighborhood services, and commercial establishments. - **Office & Professional Buildings:** General business offices, medical offices, and professional services. - **Restaurants & Hospitality:** Restaurants, cafes, banquet halls, and event facilities. - **Hotel Development:** Boutique or limited-service hotel accommodations. - **Entertainment & Recreation:** Bowling alley, indoor entertainment center, or other recreational facilities. *All proposed uses are subject to applicable zoning regulations, site plan review, and municipal approvals.*

459 Windsor Ave, Windsor

$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

$250,000

3 Beds ⋅ 2 Baths ⋅ 24214034 MLS

**HIGHEST AND BEST DUE BY SUNDAY 10/25 BY 12PM MIDNIGHT**Welcome to 281 Deerfield Road, a charming Cape Cod-style home in Windsor that's full of character and just waiting for its next owner's personal touch! With its classic exterior, inviting layout, and plenty of opportunity to make it your own, this home offers a wonderful canvas for bringing your ideas to life. Step inside to find hardwood flooring throughout much of the home, adding warmth and character to the living spaces. The living room features a cozy fireplace that serves as a natural focal point, while the separate dining room provides a welcoming space for gathering around the table. The generously sized kitchen offers plenty of room to work with and the opportunity to create something truly special. With 3 bedrooms and 1.5 bathrooms, the home offers a flexible layout that includes two bedrooms on the main level, making everyday living convenient while leaving additional space upstairs. The unfinished basement is another area full of untapped potential, whether you envision additional storage, a workshop, or the possibility of creating more usable space down the road. New mechanicals add an important update to the home, allowing the next owner to focus on making the cosmetic improvements that reflect their own style.

281 Deerfield Rd, Windsor

$650,000

1 Baths ⋅ 24211455 MLS

This Wine & Liquor Store is across from New Apartments and located in the Center of Town. This is a confidential listing. Please have Confidentiality Agreement Signed. An original loan officer has pre-qualified the property if there is a financially secure owner operator buyer to purchase the business simultaneously for $330,000 plus liquor inventory estimated at approximately $150,000. The store has new gondola clean metal shelving throughout and newer ceiling tiles. The Endless Refrigerated Display case was installed as a used unit but is very clean with glass doors and back storage. There is a kitchenette and shower in the back of the store. Customers can enter from the massive back parking lot and front spaces. The Owner of the Building is operating since taking over in 2023 as Absentee. There is a manager in place. Please do not speak to the Sales Staff. If you would like to send a client as a customer to browse, please give them proper instructions. This is a Building Opportunity to purchase the business for additional money and operate as a retail store. Your client will need to apply for licenses to continue with the operation and comply with the CT Liquor Commission.

Windsor

$439,900

4 Beds ⋅ 3 Baths ⋅ 24214027 MLS ⋅ Walden Woods BLDG.

Welcome to Walden Woods, one of Windsor's most desirable communities! This beautiful 4-bedroom Colonial-style PUD is tucked away on a quiet cul-de-sac, offering the perfect blend of elegance, comfort, and tranquility. Step inside to a dramatic two-story foyer that sets the tone for this inviting home. The beautifully remodeled designer kitchen, updated approximately 8 years ago, features exquisite granite countertops, a center island, generous cabinet space, and an eat-in dining area that opens seamlessly to the den with a cozy gas fireplace. The open floor plan is perfect for everyday living and entertaining! Newer wood flooring adds a touch of sophistication throughout. A formal living room and dining room provide additional space for hosting gatherings and holiday celebrations, just in time for Thanksgiving! Upstairs, retreat to the spacious primary bedroom suite featuring a private bath and a versatile adjoining sitting room, ideal for a dressing room, reading retreat, or home office. Three additional bedrooms offer plenty of space and flexibility. The expansive basement provides an abundance of storage space or wonderful possibilities to finish at your leisure and create additional living space to suit your needs. Enjoy peace of mind with several significant improvements, including a roof approximately 6 years old and newer heating and central air , 7-8 years old.

412 Pond Bridge Rd Unit 412, Windsor

$439,900

4 Beds ⋅ 3 Baths ⋅ 24213810 MLS

412 Pond Bridge Rd Unit 412, 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

$429,900

4 Beds ⋅ 2 Baths ⋅ 24207370 MLS

**HIGHEST ABD BEST OFFERS DUE FRIDAY OCTOBER 16TH 5PM**Step back in time while enjoying the comforts & flexibility of today in this exceptional antique home,originally built in 1775, nestled in the historic Poquonock section of Windsor.Rich w/ vintage character & charm,this distinctive property gives the rare opportunity to own a piece of Windsor history while providing an incredibly versatile living arrangement.Currently being enjoyed as a single-family home,it is easily convertible back to its original 2 family configuration,making it ideal for multi-generational living,owner-occupied investment,or those seeking additional living space.With4 bedrooms,2 full baths,2 sets of utilities, and separate living areas, it provides tremendous flexibility for today's lifestyle.Outside,nearly 1 acre of beautifully manicured grounds creates a private,picturesque setting. A charming bridge crosses a meandering brook, adding an enchanting touch to the already spectacular landscape.2 decks provide wonderful spaces for relaxing,entertaining,& taking in the peaceful surroundings.A fabulous family room overlooks the gorgeous backyard; a perfect gathering space that brings the beauty of the property indoors. Additional features include ample parking, a 2 car garage, and gas heat.This is a truly special property where history, character, nature, and versatility come together. This Windsor treasure offers possibilities that are rarely found in todays market.

1355 Poquonock Ave, Windsor

$429,900

5 Beds ⋅ 2 Baths ⋅ 24207372 MLS

**HIGHEST ABD BEST OFFERS DUE FRIDAY OCTOBER 16TH 5PM**Step back in time while enjoying the comforts & flexibility of today in this exceptional antique home,originally built in 1775, nestled in the historic Poquonock section of Windsor.Rich w/ vintage character & charm,this distinctive property gives the rare opportunity to own a piece of Windsor history while providing an incredibly versatile living arrangement.With4 bedrooms,2 full baths,2 sets of utilities, and separate living areas, it provides tremendous flexibility for today's lifestyle.Outside,nearly 1 acre of beautifully manicured grounds creates a private,picturesque setting. A charming bridge crosses a meandering brook, adding an enchanting touch to the already spectacular landscape.2 decks provide wonderful spaces for relaxing,entertaining,& taking in the peaceful surroundings.A fabulous family room overlooks the gorgeous backyard; a perfect gathering space that brings the beauty of the property indoors. Additional features include ample parking, a 2 car garage, and gas heat.This is a truly special property where history, character, nature, and versatility come together. This Windsor treasure offers possibilities that are rarely found in todays market.

1355 Poquonock Ave, Windsor

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Windsor Real Estate

Newest Listings in Windsor

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