Windsor Historical Properties for Sale

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Newest Windsor Historical Homes for Sale

$269,900

2 Beds ⋅ 1 Baths ⋅ 24202276 MLS

This pristine and charming Bungalow beautifully blends classic character with gorgeous updates and offers comfortable and beautiful living space. From the moment you enter, you will appreciate the warmth and character throughout, including beautifully refinished hardwood flooring that flows throughout the home. The updated and stunning kitchen features crisp white cabinetry as well as new lighting and new flooring, creating a bright and welcoming space for everyday living. Just off the kitchen, the dining room is ideal for serving guests or hosting holiday gatherings, complete with a lovely, built-in China cabinet. The spacious living room is filled with natural light, creating a warm and inviting setting for relaxing or entertaining. Two comfortable bedrooms and a full updated bath are tucked down the hall. Step outside to the back deck overlooking the fully fenced yard, a wonderful setting for outdoor dining, gardening, or simply enjoying a peaceful afternoon. The new railings on the deck provide a fresh, updated touch. With its timeless appeal, pristine presentation and inviting outdoor space, this delightful Bungalow is a wonderful place to call home. There is tremendous value in the brand new roof, (house and shed), refinished hardwood floors, enclosed front porch, thermal pane windows, freshly painted interior, updated bathroom, new lighting, new kitchen flooring, new electrical panel, oil tank and low maintenance vinyl siding. Come on...Let's take a look inside!

26 Highland Ave, Windsor

$624,900

4 Beds ⋅ 3 Baths ⋅ 24119748 MLS

Built by Dr. Elisha Sill, this 1800 clapboard, central-hall Georgian style home, boasts a mid-to-late 19th century English barn and a brick carriage house listed on the National Register of Historic Places. Rich in character and architectural detail, this spacious ten room residence boasts over $300,000 in upgrades and offers four bedrooms, two full and one half baths. A grand central hall welcomes you inside and sets the tone for the home's classic elegance. The remodeled kitchen features original wide board flooring, stainless steel appliances, and an expansive pantry, blending modern convenience with historic appeal. The formal dining room and inviting living room showcase beautiful and original wide board flooring and are the perfect area for entertaining. The second level offers four generously sized bedrooms with wide board flooring and two full baths. Set on approximately four picturesque acres, the property includes a carriage house, barn, and abundant space for gardens, outdoor recreation, or hobby farming. A rare opportunity to own a piece of Windsor history while enjoying the convenience of living near the center of town. There is tremendous value in the fresh interior paint (2026), fresh exterior paint and new garage doors (2025), new roof on the home (2024), new roof on the barn (2023), furnace and hot water heater (2023), central air (2023), remodeled kitchen (2015), and two story attached garage with studio (2010). Come on let's take a look inside

209 Palisado Ave, Windsor

$199,900

2 Beds ⋅ 2 Baths ⋅ 24204640 MLS

Bring your vision and unlock the potential of this two-bedroom, two-bath brick-sided Cape! Offering a functional layout, a one-car garage, and the convenience of public utilities, this home provides a solid foundation for renovation and customization. The property needs updating and repairs but presents an excellent opportunity for buyers, investors, or contractors looking to build equity and create a home tailored to their style. With some imagination and improvements, this diamond in the rough could truly shine! Items will be left at sellers discretion. Sold As Is Where Is

16 Lyme St, Windsor

$429,900

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.

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

$284,000

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

$269,900

2 Beds ⋅ 2 Baths ⋅ 24200267 MLS

Welcome Home! This charming, move-in-ready 2-bedroom, 1.5-bath Cape offers the perfect blend of comfort, character, and outdoor living. Ideally positioned on a desirable corner lot, the home features a spacious backyard and an oversized deck-perfect for summer entertaining, relaxing with friends and family, or simply enjoying your own private outdoor retreat. A generous paved parking area provides ample room for up to 6 vehicles, making everyday living and hosting guests a breeze. With its inviting charm, functional layout, and exceptional outdoor space, this wonderful home is ready for its next chapter. Come see all it has to offer!

539 Bloomfield Ave, Windsor

$330,000

4 Beds ⋅ 2 Baths ⋅ 24183615 MLS

Welcome to this charming 4-bedroom, 2 full bath residence has been lovingly owned for 47 years and features original artwork that truly reflects pride of ownership. You'll appreciate the solid construction and well-maintained features, including updated mechanicals such as the water heater, oil tanks, furnace, roof, and windows. Enjoy extra living space with a comfortable family room, the tandem bedrooms with full bath can serve as in-law space and it includes a bright 3-season sunroom, plus the added benefit of solar panels. While it does require some updating, this is a great opportunity to make it your own and it's full of potential, with plenty of storage throughout. Corner lot location that connects to a quiet cul-de-sac. This home offers a peaceful setting while staying close to schools, the highway, the library, shopping, and more.

94 Park Ave, Windsor

$250,000

3 Beds ⋅ 1 Baths ⋅ 24194927 MLS

Welcome to 128 Woodland Street, located in Windsor's desirable Deerfield neighborhood! Looks are deceiving with this adorable 1920s bungalow offering plenty of room, character, and endless potential. Spanning 1,144 sq ft this home features 3 bedrooms and 1 full bath. Highlights include a charming enclosed front porch, a spacious living room and dining room with hardwood floors, a breakfast nook, and a convenient first-floor primary complete with a walk-in closet. Looking for extra space? You'll find an additional bedroom and sitting area in the finished walk-up attic. Large lower-level walkout with expansion potential awaiting your finishing touches. Outside, enjoy your private rear patio and large level yard. Don't miss the opportunity to call this home!

128 Woodland St, Windsor

$399,000

4 Beds ⋅ 3 Baths ⋅ 24193927 MLS

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 with flexible living arrangements and space for everyone!

1178 Poquonock Ave, Windsor

$385,000

5 Beds ⋅ 5 Baths ⋅ 24181019 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

$295,000

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 Home Also Features Hardwood Floors Throughout, A Decent Sized Level Back Yard Great for Summertime Entertaining, Newer Boiler, & New Roof.

28 Skitchewaug St, Windsor

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