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Windsor, CT Houses for Sale

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  • /30

    $359,900 Open Sun 11AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,094 Sq Ft

    11 Fyler Dr, Windsor, CT 06095

    Totally renovated and move-in ready, this gorgeous ranch offers effortless one-floor living with quality upgrades throughout. Step into a beautiful, modern kitchen featuring granite countertops, tile backsplash and flooring, new cabinets, and stainless steel appliances. Gleaming hardwood floors flow into the spacious living room, complete with a cozy fireplace, wood stove insert, and a large

    Agent Photo

    Rob Rosa

    Berkshire Hathaway NE Prop.

    (860) 750-9167

    11 Fyler Dr, Windsor, CT 06095
  • /19

    $348,900

    • 4 Beds
    • 1.5 Baths
    • 1,547 Sq Ft

    118 Maple Ave, Windsor, CT 06095

    Full of charm, this unique Colonial offers four spacious bedrooms, one full bath, and one half bath all set on a desirable corner lot with an expansive yard. The main level features a bright and inviting layout boasting natural sunlight, while the upper level offers four bedrooms providing ample space all with hardwood floors throughout. An attached one-car garage adds everyday convenience, along

    Agent Photo

    Mariana DaSilva

    William Raveis Real Estate

    (860) 791-9717

    118 Maple Ave, Windsor, CT 06095
  • /39

    $389,900

    • 3 Beds
    • 2.5 Baths
    • 1,942 Sq Ft

    14 Loren Cir, Windsor, CT 06095

    Tucked at the end of a quiet cul-de-sac, this beautifully maintained raised ranch offers a perfect blend of comfort and modern updates. The bright open layout features gleaming recently refinished hardwood floors, an inviting living and dining area, and a remodeled kitchen with granite countertops, stainless steel appliances, and tile flooring. Upstairs you'll find three spacious bedrooms,

    Agent Photo

    Mike Albert

    RE/MAX RISE

    (959) 215-6076

    14 Loren Cir, Windsor, CT 06095
  • /27

    $314,925

    • 2 Beds
    • 2 Baths
    • 1,452 Sq Ft

    41 Chestnut Dr, Windsor, CT 06095

    Welcome to 41 Chestnut Drive, a charming and well-maintained Cape Cod style home nestled in a quiet Windsor neighborhood, perfect for those seeking comfort, convenience, and classic New England character. This bright and inviting residence has 2 spacious bedrooms with an extra room for either a den or an office, 2 full baths with one being totally renovated, with a flexible floor plan that blends

    Agent Photo

    Jason Kemp

    Five Stars Realty

    (860) 737-9994

    41 Chestnut Dr, Windsor, CT 06095
  • /38

    $529,900

    • 3 Beds
    • 2.5 Baths
    • 2,237 Sq Ft

    16 Landing Cir, Windsor, CT 06095

    Welcome to your dream home! This 3 bedroom, two and half bathroom gem boasts an open-concept layout, perfect for entertaining. The chef's kitchen features granite countertops, marble mosaic back splash and stainless steel appliances, and a large peninsula. The large rear deck is ideal for gatherings or quiet evenings. Located in a Cul De Sac and minutes from highways, shopping, restaurants, this

    Helton Dornelas Golden Rule Realty

    16 Landing Cir, Windsor, CT 06095
  • /30

    $550,000

    • 4 Beds
    • 5 Baths
    • 3,102 Sq Ft

    2080 Poquonock Ave, Windsor, CT 06095

    Looking for an open-concept colonial with 3000+ square feet? Search no further than 2080 Poquonock Ave. Property is located in the sought-after town of Windsor, CT. Interested in curb appeal well this is it. The exterior and interior is a combination of contemporary with a touch of georgian. One step inside and you'll be captivated by the style, elegance, and workmanship. Greet your guests in the

    Alexander Pryor Coldwell Banker Realty

    2080 Poquonock Ave, Windsor, CT 06095
  • /35

    $438,500

    • 4 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    418 Pond Bridge Rd, Windsor, CT 06095

    Nestled in the desirable Walden Woods community is this beautifully remodeled 2,304sf Colonial-style PUD home with 8 spacious rooms and exceptional modern comfort. This 4 bedroom home features a bright, open layout with a large center hallway on each floor, a fireplaced family room, and a stunning updated kitchen that opens to a private deck, perfect for relaxing or entertaining. The first floor

    Michael Ferris eXp Realty

    418 Pond Bridge Rd, Windsor, CT 06095
  • /40

    $499,900

    • 5 Beds
    • 2.5 Baths
    • 2,719 Sq Ft

    31 Parkwood Dr, Windsor, CT 06095

    Looking for space, privacy, and a connection to nature? Look no further than 31 Parkwood Drive - a 5-bedroom Garrison Colonial tucked at the end of a peaceful cul-de-sac. This special home offers joy and tranquility whether you're entertaining guests indoors or relaxing outside on the patio or in the "serenity grotto." Enjoy your morning coffee while listening to the birds in their sanctuary or

    Mary Beth Welsh Century 21 AllPoints Realty

    31 Parkwood Dr, Windsor, CT 06095
  • /39

    $539,998

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft

    400 Old Day Hill Rd, Windsor, CT 06095

    Tucked away in one of Windsor's most desirable and secluded neighborhoods, this beautiful single-family home blends modern living with timeless charm. The property features a spacious open-concept layout with a large kitchen island, updated cabinetry, and sliding doors leading to an oversized deck perfect for outdoor entertaining. Each bedroom is generously sized, and the bathrooms have been

    Garey Allen Gallagher Real Estate

    400 Old Day Hill Rd, Windsor, CT 06095
  • /23

    $449,999

    • 4 Beds
    • 3.5 Baths
    • 2,290 Sq Ft

    45 Timothy Terrace, Windsor, CT 06095

    Prime location!! A MUST SEE!! Well maintained beautiful colonial on quiet street with gleaming wood floors. Two master bedrooms with private bathrooms. Large sun filled family room with cozy fireplace. Open kitchen with brand new granite countertop. Massive backyard, great place to host summer gets together. Owner related to agent.

    Camtu Nguyen William Raveis/First Town RE

    45 Timothy Terrace, Windsor, CT 06095
  • /28

    $429,900

    • 3 Beds
    • 3 Baths
    • 1,848 Sq Ft

    680 Kennedy Rd, Windsor, CT 06095

    Welcome Home to a Stunning, freshly renovated ranch that combines modern style with classic comfort. This move-in-ready home features a brand-new roof and siding, offering excellent curb appeal and peace of mind for years to come. Inside, you'll find a bright and airy layout with new flooring, fresh paint, and thoughtful finishes throughout. The updated kitchen boasts sleek countertops, stainless

    Timothy Faucher eXp Realty

    680 Kennedy Rd, Windsor, CT 06095
  • /36

    $449,900

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    29 Quail Hollow Dr, Windsor, CT 06095

    Welcome home! This beautifully maintained Raised Ranch offers the perfect blend of comfort, style, and outdoor luxury. When you step outside, prepare to be wowed! A two-tiered deck overlooks a fully fenced-in, expansive backyard designed for pure enjoyment. Take a dip in the heated in-ground saltwater pool, unwind in the hot tub, or host unforgettable gatherings on the stamped concrete pool deck

    Michael Zizzamia William Raveis Real Estate

    29 Quail Hollow Dr, Windsor, CT 06095
  • /40

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,360 Sq Ft

    10 Cleary Ln, Windsor, CT 06095

    Nestled on a quiet cul-de-sac, this beautiful 4-bedroom, 2.1-bath ranch offers over 2,300 sq. ft. of stylish living space. The sunken living room is a true showstopper, featuring dramatic floor-to-ceiling windows that flood the space with natural light. A spacious dining room overlooks the living area, creating an open and inviting layout perfect for gatherings. The master suite and family room

    Tammy Ferrauola Eagle Eye Realty PLLC

    10 Cleary Ln, Windsor, CT 06095
  • /30

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,715 Sq Ft

    16 Hilltop Rd, Windsor, CT 06095

    LOOKING FOR A QUIET AREA TO LIVE IN ? This updated Raised Ranch on 0.75 Acres in Windsor might be the one you looking for. Beautifully remodeled in 2017 and meticulously maintained, this 3-bedroom, 2-bath Raised Ranch offers move-in-ready comfort with all major updates complete. The main level features an open-concept layout with a remodeled kitchen showcasing granite countertops, an island, and

    Joe Coelho Coldwell Banker Realty

    16 Hilltop Rd, Windsor, CT 06095
  • /36

    $436,000

    • 3 Beds
    • 2.5 Baths
    • 1,952 Sq Ft

    58 Amanda Cir, Windsor, CT 06095

    PRICED TO SELL: MAJOR DISCOUNT & FLEXIBLE PRICING! Seller is relocating out of state and wants a FAST closing! A great deal on a HEALTHY home. Key Features and Upgrades: -Solid and Move-In Ready: Roof has 15+ years of life remaining, heating system recently serviced, and all appliances in great condition. -Energy Efficient and Secure: Solar panels with backup solar generator, real-time monitored

    Steven Koleno Beycome of Connecticut

    58 Amanda Cir, Windsor, CT 06095
  • /28

    $421,000

    • 4 Beds
    • 3 Baths
    • 2,738 Sq Ft

    957 Palisado Ave, Windsor, CT 06095

    Welcome to this charming 1773 center chimney colonial in the highly desirable town of Windsor ,CT built on over an acre of land. This classic property blends old-world charm with modern conveniences. Upon arrival you will enter a spacious, updated eat-in country kitchen with a beehive oven for family gatherings. French doors open from the kitchen out onto a large slate patio with a beautiful

    Steven Koleno Beycome of Connecticut

    957 Palisado Ave, Windsor, CT 06095
  • /26

    $350,000

    • 3 Beds
    • 1.5 Baths
    • 1,720 Sq Ft

    5 Eagleton Dr, Windsor, CT 06095

    Immaculately kept raised ranch on nearly 1/2 acre mature lawn. Corner lot in a desirable neighborhood. Three bedrooms and a full bath on the main level along with the kitchen with new countertops and a spacious living room and dining room. The finished lower level with a working fireplace and 1/2 bath adds 576 square feet of additional living space- perfect for a family room or office. Sliders

    Frank Booth Berkshire Hathaway NE Prop.

    5 Eagleton Dr, Windsor, CT 06095
  • /37

    $299,100

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    100 Hayden Station Rd, Windsor, CT 06095

    Welcome to a spacious colonial with many updates. This home has large, sunny rooms. There are many updates - NEW paint, light fixtures, kitchen floor, living room carpet, bathroom vanity, boiler 2014, electrical 2011, siding 2004, roof 2021. There are hardwood floors throughout the home. The kitchen has a large walk-in pantry. Charming screened in porch. The 1-acre lot has lots of room for

    Susan King Berkshire Hathaway NE Prop.

    100 Hayden Station Rd, Windsor, CT 06095
  • /40

    $349,000

    • 3 Beds
    • 2.5 Baths
    • 1,986 Sq Ft

    9 Alford Dr, Windsor, CT 06095

    Opportunity awaits with this solid split-level home nestled at the end of a cul-de-sac in a desirable location! High value updates completed in 2025 include New Siding and Central AC! Vinyl Clad Windows throughout most of the home! Featuring a Master Bedroom with a Full Bath and Walk-In Closet. Two additional Bedrooms and another Full Bath complete the upper level. The spacious Living Room on the

    Rachel Uhlig Lion's Head Real Estate Group

    9 Alford Dr, Windsor, CT 06095
  • /38

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,874 Sq Ft

    10 Oxcart Dr, Windsor, CT 06095

    Immaculate raised ranch with a cleared and level rear lot featuring spacious sized rooms with hardwood flooring, central air, a refreshed kitchen with double ovens, new flooring, countertop and sink. All the main floor interior walls have been recently repainted. The family room in the expansive lower level has a fireplace, separate laundry room and a half bath. The solar lease is $100.52 per

    Elaine Smith Century 21 AllPoints Realty

    10 Oxcart Dr, Windsor, CT 06095
  • /25

    $225,000

    • 3 Beds
    • 3 Baths
    • 1,534 Sq Ft

    280 Deerfield Rd, Windsor, CT 06095

    Welcome to 280 Deerfield Road, where comfort and convenience come together in this inviting residence. Step inside through the enclosed front porch and into a bright, open main level featuring a spacious living room that flows seamlessly into the dining area, highlighted by a charming fireplace. The kitchen offers great potential and functionality, while the main level also includes two bedrooms

    Jonathan Gineo Silver and Oak Realty

    280 Deerfield Rd, Windsor, CT 06095
  • /16

    $399,900

    • 3 Beds
    • 1.5 Baths
    • 1,578 Sq Ft

    20 Tobey Ave, Windsor, CT 06095

    updated inside and outside. This is a unique home. Newer roof, gutters, siding , windows. Furnace , oil tank . 4Th bedrm/family room on second floor. Walk-up attic. Great location.

    Tarek Ambia Realty Center, LLC

    20 Tobey Ave, Windsor, CT 06095
  • /33

    $314,999

    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    211 MacKtown Rd, Windsor, CT 06095

    Spacious 4-bedroom, 2.5-bath Raised Ranch offering over 1,800 sq ft of living space, set on a generous 0.65-acre lot in one of Windsor's most sought-after neighborhoods. This home features a flexible layout with great potential, including a walk-out lower level with a cozy fireplace in the family room, a bedroom, and a half bath - ideal for an in-law suite or multi-generational living. Currently

    Carla Juvencio RE/MAX Precision Realty

    211 MacKtown Rd, Windsor, CT 06095
  • /40

    $319,900

    • 3 Beds
    • 1 Bath
    • 1,670 Sq Ft

    25 Maude Cir, Windsor, CT 06095

    MOVE-IN READY 3-BEDROOM RANCH with SOLAR SAVINGS! Tucked in on a quiet Cul-de-sac, this turnkey Windsor home features hardwood floors, a sunny three-season porch, and leased solar panels for near-zero electric bills. Main-level living offers 1,152 sq ft with an additional 518 sq ft in the partially finished basement - perfect for a home office, gym, or playroom. Freshly painted common areas flow

    Sharon Fox Carl Guild & Associates

    25 Maude Cir, Windsor, CT 06095
  • /36

    $370,000

    • 3 Beds
    • 2.5 Baths
    • 1,189 Sq Ft

    145 Park Ave, Windsor, CT 06095

    Look no Further! As this Move in Ready, meticulously maintained beautiful raised Ranch home with stunning curb appeal, carefully designed opened concept floor plan, is a great home for you!.This wonderful Home boasts 3 spacious bedrooms, with each room having lots of closet space.The main Bedroom features it's own bathroom,Home has 2.5 beautiful and fully renovated baths, gleaming Hardwood floors

    Dadrie Broderick Coldwell Banker Realty

    145 Park Ave, Windsor, CT 06095
  • /38

    $299,994

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    552 Stone Rd, Windsor, CT 06095

    Welcome to this charming 3-bedroom ranch located in Windsor, CT! Set in a peaceful semi-rural neighborhood yet just minutes from Route 20 and I-91, this home offers the perfect balance of comfort and convenience. Located right around the corner from Rainbow Reservoir, offering opportunities for boating, fishing, kayaking, paddleboarding, or jet skiing. Inside, you'll find original hardwood floors

    Eric Tellier Trend 2000 Real Estate

    552 Stone Rd, Windsor, CT 06095
  • /31

    $574,900

    • 6 Beds
    • 4 Baths
    • 2,984 Sq Ft

    30 Parkwood Dr, Windsor, CT 06095

    Welcome to 30 Parkwood Drive, an expansive and beautifully Dutch colonial home offering 6 bedrooms, 2 full baths, and 2 half baths sitting at the end of a cul de sac in Windsor. This versatile and spacious layout is perfect for today's lifestyles whether you need multiple home offices, guest rooms, or space for extended guest. Step inside to find sun-filled living areas and a kitchen featuring

    Kervin Figaro Five Stars Realty

    30 Parkwood Dr, Windsor, CT 06095
  • /16

    $344,900

    • 4 Beds
    • 2 Baths
    • 2,402 Sq Ft

    39 Loren Cir, Windsor, CT 06095

    Spacious 4-bedroom, 2-bathroom Contemporary home on a cul-de-sac. The open floor plan includes over 2400 sq ft with a grand entrance view of the upper loft. Features include a primary bedroom suite with a walk-in closet, 1st floor and 2nd floor bedrooms, a large extra room with woodstove and slider leading to the private level back yard. Enjoy the CAir on these hot summer days. Newer hot water

    Lavasha Bester CENTURY 21 AllPoints Realty

    39 Loren Cir, Windsor, CT 06095
  • /37

    $579,900 Open Sun 1PM - 2:30PM

    • 3 Beds
    • 2 Baths
    • 1,880 Sq Ft

    318 Capen St, Windsor, CT 06095

    COOK HILL - Windsor Development! "The Cindy Lou MODEL!" Gorgeous Ranch style home w/covered front porch and back porch. Open Kitchen, Living Room and Dining Room w/Cathedral ceilings. Unique second suite and office. Large mudroom with Laundry, Master suite w/Cathedral ceilings and Huge walk-in closet. Wonderful Open Floor Plan, Rare Find with plentiful Living space, granite countertops in

    Lori Gabriel Coldwell Banker Realty

    318 Capen St, Windsor, CT 06095
  • /6

    $569,900 Open Sun 1PM - 2:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    342 Capen St, Windsor, CT 06095

    Desirable Cook Hill - Don't Miss Out! "The Darlene Model" Offers 1,800SF of thoughtfully designed Living with 3 Bedrooms, 2.5 Baths, a 2-Car Garage, second-floor Laundry, and a versatile Office Nook. Each home features a Ready-Finish Basement/Foundation, making it easy to finish the lower level for a future Mancave, Family room, or extra Living space. Built for Energy Efficiency and modern

    Lori Gabriel Coldwell Banker Realty

    342 Capen St, Windsor, CT 06095
  • /5

    $579,900 Open Sun 1PM - 2:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    26 Cook Hill Rd, Windsor, CT 06095

    NEW CONSTRUCTION COLONIAL! Don't miss this RARE OPPORTNITY to own the Brand-new Darlene Model in the highly sought-after Cook Hill neighborhood! This thoughtfully designed 1,800 SF home offers 3 spacious Bedrooms, 2.5 Baths, a 2-Car Garage, 2nd-floor Laundry, and a versatile large Office Nook/Loft, perfect for modern Family living or remote work. Inside, you'll find Modern Lighting, white doors

    Lori Gabriel Coldwell Banker Realty

    26 Cook Hill Rd, Windsor, CT 06095
  • /36

    $489,999 Pre-Foreclosure

    • 4 Beds
    • 2.5 Baths
    • 2,184 Sq Ft

    9 Milo Peck Ln, Windsor, CT 06095

    Welcome to this beautiful colonial set in a quiet, sought-after neighborhood. This well-maintained home offers 4 spacious bedrooms, all with gleaming hardwood floors. The inviting primary suite features a private, fully tiled bath with a walk-in shower. With a total of 2.5 baths, comfort and convenience are throughout. The first floor boasts a large, light-filled family room with a fireplace that

    Carla Juvencio RE/MAX Precision Realty

    9 Milo Peck Ln, Windsor, CT 06095
  • /9

    $315,000 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,295 Sq Ft

    27 Fyler Dr, Windsor, CT 06095

    A cheerful retreat on a quiet Windsor cul-de-sac, this home puts Sage Park Middle School and Windsor High School just a breezy stroll away. Inside, hardwood floors and thermal double-pane windows team up with 15 inches of attic insulation to keep things comfortable and efficient, while the roomy layout gives everyone space to stretch. Out back, a generous 1/2-acre lot opens to private woodlands

    Anthony Marriott Weichert Realtors MRG

    27 Fyler Dr, Windsor, CT 06095
  • /11

    $990,000

    • 2 Beds
    • 3 Baths
    • 1,974 Sq Ft

    49 Seymour Rd, East Granby, CT 06026

    A Equestrian lovers delight- a unique opportunity to own 32 acres complete with renovated colonial style home and 15 stall barn with second story finished loft. This 1,925 square foot single family home has 2 bedrooms extra room that can be used as an extra bedroom and 3.0 bathrooms with a 2 car garage. There is a separate apartment above stalls and a room to add half bath in stall area. Large

    George Agnelli Agnelli Real Estate

    49 Seymour Rd, East Granby, CT 06026

Why Live in Windsor

Windsor, Connecticut, known for its historical significance as one of the first towns in the state, offers a mix of established and new homes, including Cape Cod, Colonial Revival, and ranch-style designs. The community is conveniently located near major highways like I-91 and I-291, providing easy access to New York and Hartford. Windsor's downtown features diverse dining options such as Dom’s for breakfast, Windsor Asian Bistro for Asian cuisine, and Union Street Tavern, a converted firehouse pub that hosts charity events. Residents enjoy various things to do, including summer concerts at the Town Green and Halloween festivities like Nightmare on Broad Street. Windsor Public Schools are highly rated, with John F. Kennedy School, Sage Park Middle School, Windsor High School, and Oliver Ellsworth School all earning commendable grades. Recreational opportunities abound with the Keney Park Golf Course and Windsor Meadows State Park offering outdoor activities. The city is well-connected with CT Transit bus lines, a local train station, and proximity to Bradley International Airport. Homes in Windsor range from historical properties to contemporary builds, often situated on spacious lots without sidewalks.

Home Trends in Windsor, CT

Housing Trends

Median Sale Price
$360,000
Median Single Family Sale Price
$370,000
Median Townhouse Sale Price
$348,725
Median 2 Bedroom Sale Price
$323,900
Median 1 Bedroom Sale Price
$115,000
Average Price Per Sq Ft
$231
Number of Homes for Sale
37
Last 12 months Home Sales
332
Months of Supply
1.30
Median List Price
$350,000
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
1%
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