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Windsor, CT Homes for Sale

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  • /30

    $359,900 Open Sat 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
  • /27

    $274,925

    • 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
  • /2

    $104,999

    • Land
    • 1.92 Acres
    • $54,687 per Acre

    1333 Palisado Ave, Windsor, CT 06095

    almost 2 acres of land designated for commercial building

    Agent Photo

    Raymond Malcolm

    Cornerstone Homes Plus, Inc.

    (860) 730-9967

    1333 Palisado Ave, Windsor, CT 06095
  • /32

    $369,900

    • 3 Beds
    • 2 Baths
    • 1,943 Sq Ft

    26 Hickory Dr, Windsor, CT 06095

    Welcome home to this updated ranch set in one of the area's most desirable neighborhoods. This home features 3 bedrooms, 2 full bath. The kitchen has been updated with cherry cabinets, granite counters, newer stainless steel appliances and tile backsplash. Off the kitchen is a multifunctional space which could serve as a mudroom or a sitting room with sliders to the back yard. Living room with

    Jason Donaldson Mulberry Real Estate

    26 Hickory Dr, Windsor, CT 06095
  • /11

    $325,000

    • Land
    • 12.18 Acres
    • $26,683 per Acre

    490 Old Day Hill Rd, Windsor, CT 06095

    Attention Farmers!! This 12+ acre location is strictly for the farmers. With a tobacco barn and newly updated potato barn this piece of property is ready for you to start your farming business. Agents please reach out for the specific guidelines with this property or read the agent notes

    Heather Heeb Keller Williams Realty-Longmdw

    490 Old Day Hill Rd, Windsor, CT 06095
  • /16

    $500,000

    • 4 Beds
    • 4.5 Baths
    • 3,104 Sq Ft

    123 Country Club Dr, Windsor, CT 06095

    4 bedroom, 4.5 bathrooms. 3 bedrooms on 2nd floor and 1 bedroom with full bathroom on main floor for convenience. Family room with French doors leading into the kitchen. Formal dining and formal living room. Den has a fireplace. Basement partially finished with a completely finished bathroom. Beautiful big yard space.

    Peter D'Addeo Commercial Services Realty

    123 Country Club Dr, Windsor, CT 06095
  • /7

    $1,900,000

    • Land
    • 79 Acres
    • $24,051 per Acre

    999 Stone Rd, Windsor, CT 06095

    There are two abutting parcels that offer a total of 79 acres. 999 Stone Road is a 56.7 acre parcel that is zoned Agricultural. 965 Stone Road is a 22.3 acre parcel that is zoned Industrial. The parcels are level and wooded with some open areas. The two parcels combined offer an opportunity for Industrial, Agricultural or potential Residential development. This very convenient location is just

    John Waters Berkshire Hathaway NE Prop.

    999 Stone Rd, Windsor, CT 06095
  • /40

    $359,000

    • 3 Beds
    • 2 Baths
    • 2,128 Sq Ft

    60 Nod Rd, Windsor, CT 06095

    This spacious 3 bedroom/2 full bath colonial is located in a quiet neighborhood at the end of the cul de sac. 1,428 Sq. FT plus almost 700 sq. feet of lower level finished space. The owners have done many wonderful upgrades. All new windows on the 1st floor, new front door, new gutters with leaf guards. Newly remodeled 1st & 2nd floor bathrooms. Beautifully tiled showers, upstairs bath has dual

    Andrea Calvert CENTURY 21 AllPoints Realty

    60 Nod Rd, 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
  • /5

    $579,900 New Construction

    • 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
  • /5

    $289,000

    • Land
    • 18.36 Acres
    • $15,741 per Acre

    25 Matthew Ln, Windsor, CT 06095

    Attention Builders!!! 18.36 acre residential building lot available for a private estate or possible subdivision. Water line brought in 20 ft into the property. Electrical cable and contour map available. Great location at the end of a cul-de-sac. Schedule your lot viewing today!!

    Antoinette Gooley Coldwell Banker Realty

    25 Matthew Ln, Windsor, CT 06095
  • /37

    $579,900 New Construction

    • 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
  • /34

    $420,000

    • 3 Beds
    • 2 Baths
    • 2,448 Sq Ft

    546 Palisado Ave, Windsor, CT 06095

    Welcome to 546 Palisado Avenue, Windsor - a remarkable Samuel Stoughton-built colonial dating back to 1735, where timeless New England charm meets today's modern conveniences. Rich in history and character, this home features working fireplaces, perfect for cozy winter evenings and warm gatherings. The main level offers a spacious formal dining room ideal for entertaining, along with a welcoming

    Julie Bushnell CT Comm. Realty & Select Homes

    546 Palisado Ave, Windsor, CT 06095
  • /16

    $344,000

    • 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
  • /21

    $250,000

    • 4 Beds
    • 1.5 Baths
    • 1,921 Sq Ft

    308 Prospect Hill Rd, Windsor, CT 06095

    Windsor's finest! This 1815 antique Colonial offers a true piece of history with endless potential. Situated on a flat corner lot in Windsor's highly desirable Poquonock neighborhood, this home features 4 bedrooms, 1.5 bathrooms, original 12-inch wide hardwood floors and five fireplaces. Newer Gas heating system and plenty of closet space. Enjoy proximity to local parks, Bradley International

    Eli Joseph eXp Realty

    308 Prospect Hill Rd, Windsor, CT 06095
  • /9

    $315,000

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

    27 Fyler Dr, Windsor, CT 06095

    Located on a quiet cul-de-sac in Windsor, this inviting home combines comfort, efficiency, and an exceptional setting. Within walking distance of Sage Park Middle School and Windsor High School, it offers an ideal blend of convenience and community. Hardwood floors, thermal double-pane windows, and enhanced attic insulation support energy-efficient living, while the generous floor plan provides

    Claudia Dixon Weichert Realtors MRG

    27 Fyler Dr, 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
  • /38

    $519,900

    • 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
  • /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
  • /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
  • /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
  • /30

    $389,900

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

    216 Hayden Station Rd, Windsor, CT 06095

    A wonderful opportunity awaits with this classic Colonial set on an expansive and private 7.5-acre lot, offering the perfect blend of space, comfort, and convenience. Ideally located for easy commuting to both Hartford and Springfield, and just a short drive to Bradley International Airport, this property provides a peaceful setting without sacrificing accessibility. The home features a spacious

    Jonathan Gineo Silver and Oak Realty

    216 Hayden Station Rd, 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
  • /32

    $330,000

    • 3 Beds
    • 2.5 Baths
    • 1,508 Sq Ft

    375 Dunfey Ln, Windsor, CT 06095

    375 Dunfey Lane, Windsor, CT Welcome to this beautifully updated townhouse in a quiet Windsor location! Featuring 3 spacious bedrooms, 2 full baths, and 1 half bath, this home blends comfort, convenience, and modern style. The primary suite offers a remodeled full bath in the primary bedroom (September 2025) with beautiful finishes. The home has been freshly painted throughout, offering a clean,

    Hala Hanna KW Legacy Partners

    375 Dunfey Ln, Windsor, CT 06095
  • /6

    $569,900 New Construction

    • 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
  • /17

    $249,900

    • 3 Beds
    • 2.5 Baths
    • 1,390 Sq Ft

    268 High Path Rd Unit 268, Windsor, CT 06095

    You don't want to miss this Unique Spacious and well-maintained 3-bedroom, 2.5-bath townhouse condo in the desirable Chateau Woods community. This home features an open-concept living and dining area, updated kitchen with ample cabinetry, and a private patio perfect for relaxing or entertaining. Upstairs includes three generous bedrooms, including a primary suite with master bath. Additional

    Cynthia Rabb eXp Realty

    268 High Path Rd Unit 268, 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

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.

Frequently Asked Questions

What is the average home price in Windsor, CT?
Homes for sale in Windsor, CT have an average home price of $355,574.
How many homes have sold over the last 12 months in Windsor, CT?
338 homes have sold in Windsor, CT over the last 12 months.
Is Windsor, CT a safe city?
In general, the safest neighborhoods in Windsor, CT with lower crime scores are West Windsor, Hayden and Wilson.
What are the most popular zip codes in Windsor, CT?
The most popular zip codes in Windsor, CT include 06095, 06002, 06096, 06074 and 06088.
What are the most popular neighborhoods in Windsor, CT?
The most popular neighborhoods in Windsor, CT with the most homes for sale are West Windsor, Hayden and Wilson.
How much do you need to make to afford a house in Windsor?
The median home price in Windsor is $349,950. If you put a 20% down payment of $70,000 and had a 30-year fixed mortgage with an interest rate of 6.15%, your estimated principal and interest payment would be $1,710 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $73K a year to afford the median home price in Windsor. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Windsor, CT?
Windsor, CT has highly rated public and private schools. Some of the best schools in Windsor based on Niche Grades are The Loomis Chaffee School, Watkinson School and South Windsor High School. The neighborhoods in Windsor with the highest rated schools are West Windsor, Hayden and Wilson. Browse all the schools in Windsor, CT to learn more.

Home Trends in Windsor, CT

Housing Trends

Median Sale Price
$360,000
Median Single Family Sale Price
$370,000
Median Townhouse Sale Price
$347,450
Median 2 Bedroom Sale Price
$301,000
Median 1 Bedroom Sale Price
$85,500
Average Price Per Sq Ft
$230
Number of Homes for Sale
24
Last 12 months Home Sales
338
Months of Supply
0.90
Median List Price
$349,950
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
1%
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