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209 Palisado 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

400 Old Day Hill Rd, Windsor
$529,900
4 Beds ⋅ 4 Baths ⋅ 24200628 MLS
Welcome to 400 Old Day Hill Rd, a spacious Colonial tucked away in a secluded private setting. Perfect for those who value peace, privacy, and room to spread out. Set on an expansive .99-acre lot, this 4-bedroom, 3.5-bath home offers plenty of space for everyday living and entertaining. The fully finished walk-out basement adds valuable living and recreation space and comes complete with its very own pool table, creating the perfect spot for game nights, gatherings, or relaxing with family and friends. With generous living areas, a private setting, and a spacious lot. This home offers the opportunity to enjoy comfort, space, and a little escape from the everyday while still being conveniently located. Come see all that this Colonial has to offer!

400 Old Day Hill Rd, Windsor

2050 Poquonock Ave, Windsor
$519,900
4 Beds ⋅ 3 Baths ⋅ 24178931 MLS
Welcome to 2050 Poquonock Avenue, a beautifully maintained ranch-style home offering the perfect blend of comfort, privacy, and flexibility. The stunning open-concept great room features cathedral ceilings, hardwood floors, abundant natural light, and a charming wood-burning stove. The spacious kitchen with custom cabinetry and center island flows seamlessly into the dining and living areas, making it ideal for entertaining. The primary suite offers deck access, a walk-in closet, and private bath, while two additional bedrooms, a full bath, and main-level laundry complete the first floor. The finished lower level with private entrance, full bath, bedroom, living area, and flex space is ideal for guests, multigenerational living, or a home office. Set on over an acre of park-like grounds with a large deck, 2-car garage, and ample storage throughout. Don't miss your opportunity to make this exceptional property your next home.

2050 Poquonock Ave, Windsor

33 Milo Peck Ln, Windsor
$465,000
4 Beds ⋅ 3 Baths ⋅ 24208861 MLS
Nestled in a quiet, highly sought-after neighborhood in the coveted Poquonock section of Windsor, this beautiful 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of classic elegance and modern comfort. When you pull into the driveway, the curb appeal and professional landscaping set the stage for what awaits inside. The main level features a floor plan designed for both entertaining and everyday living. At the heart of the home is a spacious eat-in kitchen boasting quartz countertops and access to a stunning Trex deck-the ideal setup for summer barbecues and seamless indoor-outdoor dining. Host holiday gatherings in the formal dining room, greet guests in the formal living room, or get cozy by the fireplace in the inviting family room. Downstairs, the partially finished basement provides fantastic bonus space for a recreation room, home office, or gym. It even features a built-in professional woodworker's bench, ready for the next hobbyist or craftsman. Key Features: Brand new windows throughout the home, complete with a transferable warranty for the new owners. Outdoor Oasis: A low-maintenance Trex deck overlooking the professionally landscaped yard. Ample Space: 4 generously sized bedrooms and 2.5 baths. This lovely home is a gem in one of Windsor's most coveted neighborhoods.

33 Milo Peck Ln, Windsor

412 Pond Bridge Rd Unit 412, 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

412 Pond Bridge Rd Unit 412, Windsor
$439,900
4 Beds ⋅ 3 Baths ⋅ 24213810 MLS
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

134 Pleasant St, Windsor
$439,900
3 Beds ⋅ 2 Baths ⋅ 24196966 MLS
Opportunity awaits with this charming 3-bedroom, 2.5-bath single-family home nestled on over 2 beautiful acres of land. Offering a wonderful combination of space, character, and privacy, this property is perfect for buyers looking to create a home that reflects their own personal style. Step inside and discover a home filled with potential. While it is ready for some TLC and updating, it offers a functional layout with generous living spaces and endless opportunities to make it your own. One of the home's standout features is the inviting sunroom, providing the perfect place to enjoy your morning coffee, unwind with a good book, or simply take in the peaceful views of the surrounding property throughout the changing seasons. Outside, you'll appreciate the expansive yard with plenty of room to enjoy the outdoors. Whether you envision gardening, hosting family gatherings, or simply enjoying the open space, this property offers the setting to do so. Tucked behind the home is a detached barn that is in need of lots of TLC but offers plenty of potential for the next owner to restore and reimagine.

134 Pleasant St, Windsor

1355 Poquonock 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

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

20 Marble Faun Ln Unit 20, Windsor
$429,900
3 Beds ⋅ 3 Baths ⋅ 24208451 MLS ⋅ Walden Woods BLDG.
Welcome to 20 Marble Faun Lane, a spacious end unit home offering a comfortable, low maintenance lifestyle in Windsor's desirable Walden Woods community. The bright and inviting main level features hardwood flooring and an open layout with plenty of space for entertaining. The kitchen has been refreshed with newly painted cabinetry and new stainless-steel appliances creating a crisp updated feel. A first-floor primary suite offers the convenience of main level living, while a separate study provides an ideal home office or den. Upstairs you'll find two additional generously sized bedrooms, a full bath and a versatile loft area. Step outside to enjoy a newer deck perfect for relaxing. A full basement provides abundant storage and the potential for additional living space while an attached two car garage keeps you out of the elements. Walden Woods offers an exceptional array of amenities including a swimming pool, clubhouse, pickleball and tennis courts and a scenic community pond. Enjoy the ease of community living while still having the space and feel of a single-family home.

20 Marble Faun Ln Unit 20, Windsor

49 Green Manor Ave, Windsor
$424,900
3 Beds ⋅ 3 Baths ⋅ 24209642 MLS
Welcome to this beautifully updated 3-bedroom, 2-bath ranch offering comfortable one-level living with stylish updates throughout. Built from the ground up in 2009, no detail was left undone.Lovely laminate flooring flows through the home, while both bathrooms have been tastefully renovated.The main bath features a double-sink vanity with granite counters and gorgeous stone tile throughout.The updated kitchen opens seamlessly to the living room and features rich cherry cabinetry, a huge center island, double oven, induction flat-top stove, and stone backsplash and flooring.Just off the living room is a spacious office, while the dining room provides an inviting space for meals and entertaining.A large family room/media room takes movie nights to the next level with a screen and 3D movie projector included.A huge laundry room and large two-car garage provide plenty of storage and everyday convenience.Step outside to your own private retreat featuring a covered patio, firepit, above-ground pool, swing set, and three storage sheds,perfect for entertaining, relaxing, and enjoying the outdoors.Numerous additional updates add comfort and peace of mind, including a whole-house water filtration system, heated roof with gutter guards to help prevent ice dams, generator hookup, three attic fans, and central air.With its thoughtful updates, versatile living spaces, and exceptional outdoor amenities, this ranch is ready to welcome you home.A must see!

49 Green Manor Ave, Windsor

707 Old Village Cir, Windsor
$399,900
3 Beds ⋅ 3 Baths ⋅ 24212983 MLS ⋅ Riverside Village,The Villages At Poquonock BLDG.
Beautiful, move-in-ready townhome at The Villages at Poquonock! This rarely available home offers approximately 1,800 square feet of inviting living space, an open floor plan, gleaming hardwood floors, and custom window shades throughout. The main level features a bright, spacious living room, dining area, half bath, and a primary bedroom with a bathroom featuring a walk-in shower. Access to the backyard patio makes outdoor relaxation easy. The stunning kitchen showcases a vaulted ceiling, abundant cabinetry, quartz countertops, a center island, and fingerprint-resistant stainless steel appliances. A washer and dryer are included, along with a Pure Wash Pro X2 system that enhances cold-water washing with oxygen. Upstairs, two generously sized bedrooms offer ample closet space and share a full bathroom. Additional conveniences include an attached one-car garage, central air, a high-efficiency A. O. Smith gas tankless water heater, and public water and sewer. Enjoy the amenities of this sought-after, 64-acre community, including walking trails, a private park with a pond, an in-ground pool, and a playscape. The clubhouse offers a fitness room, kitchen, dining area, and covered outdoor picnic space. Conveniently located near shopping, restaurants, schools, and Northwest Park's 473 acres of trails and outdoor recreation, this lovely home offers comfort, convenience, and a welcoming community.

707 Old Village Cir, Windsor

50 Hollow Brook Rd, Windsor
$398,000
3 Beds ⋅ 3 Baths ⋅ 24208844 MLS
Beautifully maintained with a level of care evident throughout, 50 Hollow Brook Road elevates the classic raised ranch with rich hardwood floors, tasteful updates, and an impressive amount of finished living space on a generous .64-acre corner lot. The main level opens to a connected living and dining area, where hardwood flooring brings warmth and character. The adjoining white kitchen pairs black granite countertops with updated stainless steel appliances and abundant cabinetry for exceptional storage. The primary bedroom features its own private half bath, while two additional bedrooms and a full bath complete the main level. Hardwood flooring continues throughout the bedrooms. Downstairs, the finished and heated lower level is anchored by a wood-burning fireplace, creating an inviting second living area or den. A second half bath and dedicated laundry area add convenience, while the mechanical room provides additional space for a workshop, organized storage, or both. Direct access to the attached one-car garage completes this level. Outside, the level corner lot offers generous backyard space. Convenient to Windsor schools, shopping, local amenities, and major highways, this home pairs enduring finishes and expanded living space with a beautifully maintained property in an established Windsor neighborhood.

50 Hollow Brook Rd, Windsor

11 Rhodora Ter Unit 11, Windsor
$359,900
2 Beds ⋅ 3 Baths ⋅ 24206424 MLS ⋅ Walden Woods BLDG.
Absolutely pristine! Welcome to the sought after Walden Woods community, where peaceful surroundings and beautiful natural scenery combine to create an idyllic setting. From the covered entryway, step inside this absolutely stunning two bedroom, two full and one half bath home offering comfort, style and thoughtful updates throughout. The beautiful kitchen features an abundance of gorgeous cabinetry, a pantry, new granite countertops, stainless steel appliances and a spacious dining area. Open to the kitchen, the elegant dining room, with a new chandelier, and inviting living room showcase gleaming hardwood flooring and a fireplace, perfect for special evenings. A half bath completes the first level. Upstairs, two generously sized bedrooms include a spacious primary suite with cathedral ceilings, a large walk-in closet, an updated full bath featuring a tile-surround, walk-in shower and double vanity. A second bedroom and full bath and a separate laundry room complete the upper level. The finished walk-out lower level (2021) offers versatile space for a fabulous family room, home office, hobby area, and has separate additional storage. There is tremendous value in the newer furnace and hot water heater, central air, nine foot ceilings and gorgeous hardwood flooring. Walden Woods is recognized for its meticulous grounds, saltwater in-ground pool, community gardens, pickle ball courts, a fabulous club house and an outstanding community. Come on...Let's take a look inside

11 Rhodora Ter Unit 11, Windsor

280 Deerfield Rd, 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!

280 Deerfield Rd, Windsor

34 Grande Ave, Windsor
$349,000
3 Beds ⋅ 2 Baths ⋅ 24209219 MLS
Welcome to 34 Grande Avenue, a beautifully remodeled 3-bedroom, 2-full-bath split-level situated on a corner lot in a desirable Windsor neighborhood! Updated from top to bottom, this home combines turnkey condition with the versatility that makes split-level living so popular. The main level features a bright, open-concept layout where the living room, dining area and gorgeous newly remodeled kitchen flow seamlessly together-perfect for family time and entertaining. Upstairs, the bedrooms offer ample closet space, while the primary bedroom features a walk-in closet and its own beautifully updated full bath. The finished lower level provides even more living space, ideal for a playroom, exercise area, home office or media room, with additional room for a workshop and storage. Step outside to a delightful backyard that's private, level and ready for everything from cookouts and games to gardening and relaxation. Mini-splits provide efficient cooling, while town water and sewer add everyday convenience. Beautifully updated, exceptionally maintained and truly move-in ready-come see 34 Grande Avenue before someone else calls it home!

34 Grande Ave, Windsor

94 Park 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

37 Clover St, 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

245 Deerfield Rd, Windsor
$320,000
6 Beds ⋅ 5 Baths ⋅ 24185539 MLS
Price Improvement! Own a piece of history in this 1796 colonial, built by Elisha Moore, a 4-unit investment property on .77 acre. Included a one-car garage with bay, a loft above the garage that can be used for crafting, office, man's cave, storage, or additional income, with plenty of parking for tenants/guests. This current owner started renovations, but could not complete them. When the home was purchased in 2021, the main unit consisted of ~2200 sqft with 3 bedrooms & 2 baths with separate entrances from the rest of the house. The front building is divided into 3 separate units, each with a kitchen, Living area, one bedroom & bath. Live in the main unit and rent the other 3. There is a brick outbuilding that can also be used as additional storage. Two of the units have been gutted/partially reframed and the floors removed, and never completed. You can change the floor plan. With a stand-up attic possibly be expanded with additional rooms. Great property for an investor looking to restore a priceless piece of history. A lot of potential for someone creative, patient, and accepts a rewarding challenge. The home is being sold AS-IS. Home inspections for informational purposes only. Plumbing does not work. A hold harmless is required for all showings. "Back on market-buyer financing collapsed."

245 Deerfield Rd, Windsor

1008 N Worthy St, 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

930 Delilah Dr, 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

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