Windsor Historical Properties for Sale

Our website features the best real estate search for historical properties available in Windsor and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Windsor Historical Homes for Sale

$349,900

3 Beds ⋅ 2 Baths ⋅ 24208051 MLS

You will find tremendous charm and character in this inviting, four bedroom Colonial nestled on a fabulous and level .41 acre lot. Timeless details include hardwood flooring throughout, crown molding, built-in shelving and a built-in China cabinet. The kitchen features gorgeous maple cabinetry, a tile backsplash, an abundance of countertops, stainless steel appliances and a pantry. The adjoining dining room offers a built-in hutch and cabinets, creating a welcoming space for meals and social gatherings. The expansive living room is filled with natural light and boasts built-ins and a wood-burning fireplace, creating a warm setting for relaxing or entertaining. A door to the outside brings you to a lovely covered side porch. A flexible main level room, currently used as an office, offers the versatility to serve as a bedroom or additional living space. Upstairs, three comfortable bedrooms and a conveniently located full bath await. Step outside to the brick patio overlooking the yard, complete with a storage shed and space for outdoor dining, gardening or simply enjoying the outdoors. Great value is found in the newer furnace, hot water heater and updated electrical. Ideally situated near schools, a variety of shopping, dining, coffee shops and our lovely town center where the community comes together for summer concerts, holiday events, a seasonal farmers market, a fabulous library and walking trails along the scenic Farmington River. Come on...Let's take a look inside!

21 Laurel Ave, Windsor

$340,000

3 Beds ⋅ 2 Baths ⋅ 24213135 MLS

Welcome to this charming Colonial style home with 3 beds 2.1 bath in historical Windsor. Complete with Hardwood floors throughout. Open concept floor plan, from the oversized Dining room to the fireplaced Living room. A Sitting room/Sunroom/Office with french doors to the living room. Freshly painted. Granite countertop with tile backdrop. While on the 2nd floor you will notice a private outside sitting area near the master bedroom. This home has a 2 car garage just waiting to protect your vehicles from the northeast elements. A level landscaped yard is great for family activities. Nice area for walking, as both sides have sidewalks. Great location-close to shopping, churches, great schools both public and private, and the Recreation Center. Access to Highways to I-91 and I-291 are close by.

24 Giddings Ave, Windsor

$310,000

3 Beds ⋅ 1 Baths ⋅ 24217146 MLS

Price Improvement! With a little TLC, this property could truly shine. Schedule your showing today! This charming 3-bedroom, 1-bath Old Style home offers classic character, some interior upgrades, and so much potential! The fenced-in yard provides a great space for outdoor entertaining, gardening, or simply relaxing. A detached two-car garage adds convenience and extra storage. With a blend of traditional charm and thoughtful improvements, this home offers endless possibilities to add your personal touches and make it truly your own. Whether you're looking for your first home or your next project, this property is full of opportunity. Bring your vision and imagine the possibilities!

794 Matianuck Ave, 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

$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

$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

$349,900

3 Beds ⋅ 2 Baths ⋅ 24212205 MLS

Welcome to 280 Deerfield Road, a beautifully updated 3-bedroom cottage offering 1,534 square feet of comfortable, move-in-ready living space. Thoughtfully renovated throughout, this inviting home blends classic character with modern finishes. Enter through the enclosed front porch and discover a bright, open main level featuring a spacious living room with a charming fireplace and an easy flow into the dining area perfect for everyday living and entertaining. The updated kitchen offers both style and functionality, while two bedrooms and a full bathroom on the first floor provide convenient single-level living. Upstairs, a generously sized third bedroom with a half bathroom creates a flexible space for a private retreat, guest room or home office. Outside, enjoy a level, fenced backyard with a large deck and storage shed. The full walk-out basement includes a laundry area and offers ample storage and additional possibilities. Conveniently located near shopping, dining and major highways, this completely updated Windsor home is ready for its new owner! Back on the Market due to buyer not securing financing.

280 Deerfield Rd, 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

$409,900

3 Beds ⋅ 2 Baths ⋅ 24202592 MLS

Welcome to 15 Barber Street, a beautifully renovated 1930 Windsor home offering fresh finishes, spacious living areas, and plenty of room to enjoy inside and out. Recent updates include new vinyl plank flooring, fresh paint throughout, a newly added half bath, and a refreshed kitchen with new cabinets, countertops, and appliances. The large living room is anchored by a fireplace and offers plenty of space for both everyday living and entertaining. The basement has been gutted, creating a clean slate for storage, workshop space, or future finishing potential. Out back, the generously sized yard provides excellent space for entertaining, gardening, pets, or recreation, especially for a home of this size. With public water and sewer, a Trex deck platform deck, and extensive interior updates already completed, 15 Barber Street offers a move-in-ready opportunity while still retaining the character of its 1930 construction. one of the parties to the LLC has an active real estate license.

15 Barber St, Windsor

$279,900

3 Beds ⋅ 2 Baths ⋅ 24201599 MLS

Attention Buyers, Investors & Agents! This home offers three bedrooms, one-and-a-half bathrooms, central air, hardwood floors, and an eat-in kitchen. With some TLC, the hardwood floors can be restored and brought back to life, adding character and value while creating an opportunity to build equity. One of the home's standout features is the heated bonus room, filled with natural light and offering flexibility for use as a family room, home office, study, or sunroom. Sliders provide direct access to the deck, which overlooks the rear yard. The rear yard offers plenty of space with a gentle decline and additional land, giving someone willing to put their imagination and tools to work an opportunity. Several sheds and pieces of equipment in the rear yard will convey with the property. The unfinished basement provides even more potential. Bring your tool belt and transform this space into something special-whether for additional living space, a workshop, a recreation area, or storage. The property also offers great front-yard curb appeal and a solid foundation for someone looking to make improvements and create value. The property is being sold AS IS. The buyer will be responsible for removing any remaining contents and personal items left behind. Whether you're an investor looking for your next project, a buyer searching for an affordable home with potential, or an agent representing someone ready to take on a renovation, this property is worth a look. Bring your vision

930 Delilah Dr, Windsor

$270,000

2 Beds ⋅ 1 Baths ⋅ 24201430 MLS

Diamond in the Rough Investors and homeowners, take notice! This 2-bedroom, 1-bath cottage-style home is tucked away in a tranquil setting and offers an incredible opportunity for the right buyer. This property will need an overhaul, but the potential is there to transform it into something truly special. The garage has also been newly remodeled, adding even more value and versatility to the property. Bring your vision, your imagination, and your renovation ideas! Come take a look and see the possibilities for yourself!

342 Mountain Rd, Windsor

$389,000

4 Beds ⋅ 3 Baths ⋅ 24193927 MLS

The sellers are motivated! Its an Autumn sale! Don't miss this beautifully renovated premium ranch,offering modern updates,versatile living space,and peace of mind for years to come!This gorgeous 4-bedroom,3-bath home also features a dedicated office/study,the washer and drier hooks up at the both floors making it ideal for a large or multigenerational family.The main level offers two bedrooms,two full baths,and an office.The inviting living room features updated flooring and flows seamlessly into the completely renovated kitchen,showcasing brand-new appliances,cabinetry, and elegant granite countertops.The stunning new common bath adds a luxurious touch,while the primary bedroom features an updated private bath and spacious closet.A charming sunroom conveniently located off the bedroom provides the perfect space to relax and enjoy the natural surroundings.The lower level offers two additional bedrooms,a full bath, and a spacious living area accessible from both bedrooms-an excellent setup for an in-law suite, guests,or extended family.The walkout leads to a covered patio, creating an inviting space to enjoy the outdoors.The generously sized backyard is surrounded by nature and provides plenty of room for entertaining,gatherings,and enjoying time with family and friends.With extensive updates completed throughout the home,this property is truly move-in ready and has been thoughtfully renovated from top to bottom.A rare opportunity to own a beautifully updated ranch.

1178 Poquonock Ave, Windsor

$315,000

3 Beds ⋅ 2 Baths ⋅ 24192736 MLS

Welcome Home to 284 Deerfield Rd. Nestled in a convenient location, this charming 3-bedroom, 2-bathroom bungalow offers 1,511 sq ft of living space full of potential and ready for your personal touch. Spread across two stories, this home offers a unique layout and comfortable living spaces, giving you the perfect canvas to make it truly your own. Step outside to enjoy a fully fenced-in yard and a large deck - ideal for entertaining, relaxing, or simply enjoying some outdoor space of your own. Location is everything, and this home delivers - with easy access to major highways (91, 291, and 84), you'll enjoy a quick commute in any direction. You're also just minutes from shopping, parks, and a convenient bus route, making everyday errands and outings a breeze. Don't miss your chance to turn this house into your dream home - schedule a showing today!

284 Deerfield Rd, Windsor

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Windsor Historical Properties for Sale

Newest Windsor Historical Homes for Sale

How much is your home worth?

How much is your home worth?