29

Windsor, CT Homes for Sale under $500,000

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  • /32

    $324,900

    • 3 Beds
    • 2 Baths
    • 1,533 Sq Ft

    1943 Logans Way, Windsor, CT 06095

    Welcome to desirable Mills Landing, a 55+ Planned Unit Development (PUD) in Windsor's sought-after Deerfield section, offering a limited community of just 12 units. This well-maintained half-duplex home is ideally situated on a quiet cul-de-sac and features 1,533 square feet of comfortable living space with 3 bedrooms, 2 full baths, and an attached 1-car garage. The main level offers an inviting

    Agent Photo

    Ryzard Villa

    Premier Properties of CT

    1943 Logans Way, Windsor, CT 06095
  • /17

    $239,900

    $20K PRICE DROP
    • 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

    Agent Photo

    Cynthia Rabb

    eXp Realty

    268 High Path Rd Unit 268, Windsor, CT 06095
  • /40

    $419,900

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,694 Sq Ft

    99 Pepperbush Way, Windsor, CT 06095

    Completely renovated and move-in ready! This stunning 3-bedroom, 2.5-bath raised ranch in Windsor has been thoughtfully updated from top to bottom and offers the perfect blend of modern style and everyday comfort. Step inside to a bright, open-concept main level featuring soaring vaulted ceilings, luxury vinyl plank flooring, and an expansive living and dining area centered around a beautiful

    Agent Photo

    Amy Rio

    Better Homes and Gardens Real Estate Executive Real Estate

    99 Pepperbush Way, Windsor, CT 06095
  • /40

    $385,000

    $15K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 2,812 Sq Ft

    521 W Wolcott Ave, Windsor, CT 06095

    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

    Kiara Rusconi William Raveis Real Estate

    521 W Wolcott Ave, 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
  • /39

    $449,900

    Open Sat 11AM - 12:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,743 Sq Ft

    40 Eastview Dr, Windsor, CT 06095

    Nestled in a quiet neighborhood, this spacious 4-bedroom, 2.5-bath home offers the perfect blend of comfort, character, and opportunity. Freshly painted throughout, this home is a blank slate ready for its next owner to make it their own. The inviting floor plan features hardwood floors, a dramatic vaulted-ceiling living room, and a large rec room with exposed wood beams and a beautiful Vermont

    Dawn Gagliardi Serhant Connecticut, LLC

    40 Eastview Dr, Windsor, CT 06095
  • /23

    $315,000

    Pre-Foreclosure
    • 3 Beds
    • 2 Baths
    • 1,229 Sq Ft

    36 Woodybrook Rd, Windsor, CT 06095

    Welcome to Windsor! This well-maintained home offers a bright, functional layout with comfortable living spaces, an open kitchen, and generously sized bedrooms. Enjoy a private backyard perfect for relaxing, entertaining, or gardening. Conveniently located near parks, shopping, dining, schools, and major highways, this home combines everyday comfort with easy access to everything Windsor has to

    Richard Dale Realty ONE Group Connect

    36 Woodybrook Rd, Windsor, CT 06095
  • /31

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,511 Sq Ft

    284 Deerfield Rd, Windsor, CT 06095

    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

    Jill Menard Realty One Group Cutting Edge

    284 Deerfield Rd, Windsor, CT 06095
  • /10

    $499,900

    $35K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,984 Sq Ft

    30 Parkwood Dr, Windsor, CT 06095

    Space abounds!! Possible 6 or more bedrooms, possible 1st-floor bedroom. Possible in-law situation. Cul-de-sac location adjacent to a park in the center of town. Ample space! Home office, Game room, room to grow!3 fireplaces, a garden area. Needs some Love and Light.

    Kimberly Coccomo Berkshire Hathaway NE Prop.

    30 Parkwood Dr, Windsor, CT 06095
  • /32

    $324,999

    $35K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,841 Sq Ft

    76 Sinclair St, Windsor, CT 06095

    Not your grandmother's Cape. This one lives like a Colonial! In 2010 the upper floor was removed and replaced with two spectacular bedrooms, a sitting area and a full bath, all with level 8' ceilings. Plumbing and electrical systems were upgraded as part of that ambitious project. Central Air was added in 2018. On the main level, walls have been removed to create the sought-after Open Floorplan.

    Dan Babich REMAX Revolution

    76 Sinclair St, Windsor, CT 06095
  • /25

    $275,000

    Coming Soon
    • 3 Beds
    • 1.5 Baths
    • 1,150 Sq Ft

    15 Bina Ave, Windsor, CT 06095

    Welcome to 15 Bina Avenue! Offering 1,150 square feet of endless potential, this Windsor home is a exceptional opportunity for buyers or investors looking to customize, add updates, and build immediate equity. The main level features a functional living layout with great natural light and effortless flow. Upstairs, you will find three bedrooms complete with original hardwood floors and 1.5

    Anna Laurie Coldwell Banker Realty

    15 Bina Ave, Windsor, CT 06095
  • /33

    $379,000

    Open Sun 1PM - 3PM
    • 2 Beds
    • 2 Baths
    • 1,184 Sq Ft

    34 Eastview Dr, Windsor, CT 06095

    Welcome home to this charming and well-maintained 3-bedroom, 2-bath residence located in a desirable Windsor neighborhood. Thoughtfully updated to maximize comfort and functionality, the current owner has transformed one of the bedrooms into a spacious walk-in closet, creating a luxurious primary suite experience. The room can easily be converted back to a third bedroom, home office, or nursery

    Kristel Bolden-Gray eXp Realty

    34 Eastview Dr, Windsor, CT 06095
  • /13

    $449,000

    • 4 Beds
    • 2.5 Baths
    • 1,928 Sq Ft

    46 Lincoln Way, Windsor, CT 06095

    Welcome to this spacious 4-bedroom, 21/2-bath Colonial located in one of Windsor's established neighborhoods. Offering generous living space, a functional floor plan, and solid bones, this home presents an excellent opportunity for buyers looking to add their own personal style and updates. The main level features a welcoming foyer, a bright living room, formal dining room, a spacious eat-in

    John Grubiak Surf Realty LLC

    46 Lincoln Way, Windsor, CT 06095
  • /36

    $329,900

    Open Sun 1PM - 3PM
    • 3 Beds
    • 2.5 Baths
    • 1,168 Sq Ft

    1008 N Worthy St, Windsor, CT 06095

    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.

    Davone Biggins Berkshire Hathaway NE Prop.

    1008 N Worthy St, Windsor, CT 06095
  • /38

    $439,900

    • 3 Beds
    • 2.5 Baths
    • 2,599 Sq Ft

    28 Somerset Dr, Windsor, CT 06095

    Move right in and enjoy this beautiful three bedroom, two full and one half bath Colonial home, offering inviting living spaces and a sought after floor plan. The stunning and well appointed kitchen boasts an abundance of beautiful maple cabinetry, granite countertops and breakfast bar, stainless steel appliances, pendant lighting, tile backsplash and a sunny dine-in area. The heart of the home

    Sharon Rispoli Berkshire Hathaway NE Prop.

    28 Somerset Dr, Windsor, CT 06095
  • /36

    $449,000

    $12K PRICE DROP
    • 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
  • /9

    $265,000

    $84K PRICE DROP
    • Land
    • 13.3 Acres
    • $19,925 per Acre

    0 Walnut and Larch Dr, Windsor, CT 06095

    This 13.3 acre property consists of high-quality farmland that has naturally regenerated into a forest of white pine and mixed hardwoods. The land was originally created as 16 individual lots as part of an adjacent subdivision that was never completed and has since been combined into one contiguous parcel. Most of the property is now zoned Agricultural, with a few acres at the north end remaining

    Keith Ross Landvest, Inc

    0 Walnut and Larch Dr, Windsor, CT 06095
  • /36

    $390,000

    $10K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,818 Sq Ft

    27 Eagleton Dr, Windsor, CT 06095

    Welcome to 27 Eagleton Drive, a charming home tucked away on a quiet cul-de-sac in a peaceful neighborhood setting. This property offers a 1/2 acre level lot and a spacious backyard, perfect for outdoor enjoyment, entertaining, gardening, or simply relaxing in a private setting. One of the standout features is the freshly painted, screened-in back porch, providing a comfortable space to enjoy the

    John Brewer Exceptional Real Estate LLC

    27 Eagleton Dr, 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
  • /25

    $389,900

    Open Sun 1PM - 3PM
    • 3 Beds
    • 1.5 Baths
    • 1,346 Sq Ft

    437 W Wolcott Ave, Windsor, CT 06095

    Welcome home to 437 W.Wolcott. This lovely raised ranch, has been proudly owned by the same family for over 30 years. This charming 3-bedroom, 2-bath home offers warmth and character throughout, featuring beautiful hardwood floors, two cozy fireplaces, and a timeless brick exterior. The inviting layout provides comfortable living spaces perfect for everyday living and entertaining. Step outside

    Yvonne Wilson Toro Real Estate LLC

    437 W Wolcott Ave, Windsor, CT 06095
  • /35

    $339,900

    • 2 Beds
    • 2 Baths
    • 1,263 Sq Ft

    310 Kings Landing Unit 310, Windsor, CT 06095

    Welcome to Kings Landing, a phenomenal 55+ community where you can enjoy effortless condo living in this beautifully refreshed two-bedroom, two-full-bath home. Freshly and professionally painted throughout, the interior offers a pristine, bright feel from the moment that you walk in the front door. Upon entering the lovely and bright foyer, the home's immaculate condition is unmistakable. One's

    Sharon Rispoli Berkshire Hathaway NE Prop.

    310 Kings Landing Unit 310, Windsor, CT 06095
  • /29

    $425,000

    Open Sat 11AM - 2PM
    • 5 Beds
    • 2 Baths
    • 2,329 Sq Ft

    23 Lyme St, Windsor, CT 06095

    Open house schedule- 7/31: 4pm-7pm. & 8/1: 11am-2pm Windsor's finest ! This amazing 2 family is the perfect property for investors or owner occupants! Featuring 3 bedrooms and 1 bathroom on the first floor and 2 bedrooms and 1 bathroom on the second floor. Can easily maximize your cash flow. Remodeled units throughout. Newer gas heating systems, Newer Roof, Newer Siding, electrical and windows as

    Eli Joseph eXp Realty

    23 Lyme St, Windsor, CT 06095
  • /24

    $389,999

    $5K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,622 Sq Ft

    33 Mechanic St Unit 203, Windsor, CT 06095

    Price Drop! An artist's dream! This beautiful, spacious urban sanctuary nestled in the heart of downtown Windsor. Perfectly located between nature and convenience, with only steps from trails, the Amtrak station, coffee shops and quaint restaurants. Unlike any other unit in the complex, this 2 BR plus DEN (currently used as a bedroom) boasts 2 additional loft living spaces, and many other unique

    Hawwa Djuned Maria Acuna Real Estate

    33 Mechanic St Unit 203, Windsor, CT 06095
  • /30

    $300,000

    • 2 Beds
    • 1.5 Baths
    • 1,193 Sq Ft

    283 Strawberry Cir, Windsor, CT 06095

    Move right into this spacious and well maintained 2 bedroom and 1.5 bath townhome in Strawberry Hills that offers central air and gas heat. Step inside to discover a stylish main level, large dining room/living room combo with hardwood floors and remodeled kitchen with stainless steel appliances. Sliders to your private deck to relax or have a BBQ. The upper level has 2 good size bedrooms and

    Jeffrey King Carl Guild & Associates

    283 Strawberry Cir, Windsor, CT 06095
  • /37

    $379,900

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    124 Grove St, Windsor, CT 06095

    REMODELED JUST A FEW YEARS AGO!! Incredible kitchen with white cabinets, subway tile backsplash, granite counters & all newer appliances! There is a PRIMARY BEDROOM SUITE with a FULLY REMODELED BATHROOM! The second full bathroom in the hallway is also fully remodeled with a navy blue vanity, tile shower with tub and tile floor. Also done in 2024, the roof, the vinyl siding, new 100amp electrical

    Tracy Wagner Rockoff Realty

    124 Grove St, Windsor, CT 06095
  • /36

    $250,000

    Open Sun 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 1,260 Sq Ft

    323 Dunfey Ln, Windsor, CT 06095

    Welcome to this beautifully updated townhouse offering 2 bedrooms, 2.5 baths, and the perfect blend of comfort and convenience. The bright, inviting layout features spacious living areas and a partially finished basement adding approximately 150 square feet of versatile space-ideal for a family room, home office, gym, or playroom. Major mechanical updates provide peace of mind, including a new

    Jessica Starr Starr Team at LPT Realty

    323 Dunfey Ln, Windsor, CT 06095
  • /36

    $469,900

    • 4 Beds
    • 3 Baths
    • 2,027 Sq Ft

    9 Washington Rd, Windsor, CT 06095

    Wonderfully updated 4 Bedroom Ranch house with all bedrooms on the main floor. The master bedroom has two closets and a full bathroom. Property has 3 full Bathrooms with one located in the lower level which could allow for an in-law apartment. There is a door that allows access to the basement/lower level from the exterior of the house and access from the interior also. The lower level is heated

    Terrence Durrant Douglas & Tinker Realty

    9 Washington Rd, Windsor, CT 06095
  • /14

    $290,000

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,472 Sq Ft

    28 Skitchewaug St, Windsor, CT 06095

    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 Well-Maintained Home Also Features Hardwood Floors Throughout, A Full-Size Deck, A Decent Sized Level Back Yard

    Craig Ings Hill Top Real Estate, LLC

    28 Skitchewaug St, Windsor, CT 06095
  • /3

    $395,000

    • Land
    • 11.8 Acres
    • $33,475 per Acre

    2627 Day Hill Rd, Bloomfield, CT 06002

    Unique opportunity on the Bloomfield/Windsor line with easy access the the highway. Unique opportunity for single family home on a large parcel or possibly several homes with town approval. Bloomfield is located in Central Connecticut, just 10 minutes west of the state capitol, Hartford. It is easily accessible to Bradley International Airport and interstates 84 and 91. The Town encompasses 26.4

    Kris Barnett Berkshire Hathaway NE Prop.

    2627 Day Hill Rd, Bloomfield, CT 06002

Home Price Trends

Median Sale Price
$375,000
Median Single Family Sale Price
$386,500
Median Townhouse Sale Price
$255,000
Median 2 Bedroom Sale Price
$300,000
Median 1 Bedroom Sale Price
$89,500
Average Price Per Sq Ft
$238
Number of Homes for Sale
29
Last 12 months Home Sales
323
Months of Supply
1.10
Median List Price
$369,900
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
5%
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