Windsor, CT Homes

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  $359,900

  • 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

  

  Rob Rosa

  Berkshire Hathaway NE Prop.

  (860) 750-9167

  11 Fyler Dr, Windsor, CT 06095
• Explore Windsor

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  $2,000 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 972 Sq Ft
  • House for Rent

  925 High Path Rd, Windsor, CT 06095

  Two-bedroom unit in desirable Chateau Woods Complex. Open living concept - large living/dining room with slider leading out to your private patio with views of nature. This condo features new easy to maintain flooring throughout; Jack and Jill bathroom with two separate half baths on both sides of shower/bath area; lots of closet space including a large walk-in closet. Bedrooms that fit any size

  

  Mavourneen Costello

  NextHome Elite Realty

  (860) 851-4219

  925 High Path Rd, Windsor, CT 06095
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  $500,000 Sold Oct 09, 2025

  464 Prospect Hill Rd, Windsor, CT 06095

  • 4 Beds
  • 3 Baths
  • 2,949 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Above List Price
  • $170/SF
  • 72 Days On Market

  Last Listing Agent Michael Barile Barile Realty Group

  464 Prospect Hill Rd, Windsor, CT 06095
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  Est $457,635 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,722 Sq Ft

  Unlisted Address

  Unlisted Address
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  $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

  

  Jason Kemp

  Five Stars Realty

  (860) 737-9994

  41 Chestnut Dr, Windsor, CT 06095
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  $1,920 - $3,350 total monthly price

  The Preserve at Great Pond

  Studio - 3 Beds

  100 Lexington St, Windsor, CT 06095

  Welcome to The Preserve at Great Pond – where comfort and luxury meet. Embraced by nature, yet close to urban conveniences, our luxury apartments in Windsor, CT, cater to city dwellers and outdoor adventurers alike. Add in the thoughtful collection of services and amenities, and you’ll have everything you expect from a true home.Live the luxury life in any of our studio, one, two, or

  100 Lexington St, Windsor, CT 06095
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  $253,000 Sold Sep 30, 2025

  116 Henry St, Windsor, CT 06095

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft
  • Built 1950

  Last Sold Summary

  • 1% Above List Price
  • $274/SF
  • 42 Days On Market

  Last Listing Agent Laura Armstrong-Gonzalez RE/MAX One

  116 Henry St, Windsor, CT 06095
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  Est $381,658 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft

  33 Mechanic St Unit 305, Windsor, CT 06095

  33 Mechanic St Unit 305, Windsor, CT 06095
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  $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

  

  Raymond Malcolm

  Cornerstone Homes Plus, Inc.

  (860) 730-9967

  1333 Palisado Ave, Windsor, CT 06095
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  $1,600 total monthly price

  • 1 Bed
  • 1.5 Baths
  • 723 Sq Ft
  • Apartment for Rent

  962 High Path Rd, Windsor, CT 06095

  Spacious 1 bedroom, 2 bathroom condo unit for rent in The Chateau Wood Complex in Windsor. Come enjoy the open concept living area, updated kitchen, and community pool. Lower monthly bills with heat and hot water included! Conveniently located near shopping, restaurants, and major highways. Available Feb 1st.

  Marc Krawiec The Bridge Realty Inc

  962 High Path Rd, Windsor, CT 06095
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  $280,000 Sold Oct 15, 2025

  149 Tobey Ave, Windsor, CT 06095

  • 3 Beds
  • 1.5 Baths
  • 1,554 Sq Ft
  • Built 1950

  Last Sold Summary

  • 40% Above List Price
  • $180/SF
  • 4 Days On Market

  Last Listing Agent Sharon Rispoli Berkshire Hathaway NE Prop.

  149 Tobey Ave, Windsor, CT 06095
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  Est $279,252 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,085 Sq Ft

  106 Grove St, Windsor, CT 06095

  106 Grove St, Windsor, CT 06095
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  $259,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,194 Sq Ft

  99 Pepperbush Way, Windsor, CT 06095

  3-bedroom, 2.5-bath raised ranch offering comfort and convenience in a desirable setting. This home features a 2-car attached garage, natural gas heat, and public utilities for ease of living. The lower level offers even more living space with a family room, half bath, laundry, and direct access to the garage. With its functional floor plan and sought-after utilities, this home is ready for its

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 300-2726

  99 Pepperbush Way, Windsor, CT 06095
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  $1,805 - $2,170 per month plus fees

  Founders Square

  Studio - 1 Bed

  150 Broad St, Windsor, CT 06095

  NOW TOURING AND LEASING!! Come find your new home at Founders Square - Where Timeless Charm Meets Modern Living.Located just steps from the heart of Windsor Center, Founders Square offers more than 120 studio and one-bedroom apartments, along with 10,000 square feet of local retail. Here, classic New England architecture blends beautifully with modern art and sophisticated design,

  150 Broad St, Windsor, CT 06095
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  $360,000 Sold May 30, 2025

  11 Merli Rd, Windsor, CT 06095

  • 3 Beds
  • 1.5 Baths
  • 1,710 Sq Ft
  • Built 1995

  Last Sold Summary

  • 6% Above List Price
  • $211/SF
  • 2 Days On Market

  Current Estimated Value $372,801

  Last Listing Agent Maureen Bohrer Howard Hanna Rand Realty

  11 Merli Rd, Windsor, CT 06095
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  Est $375,136 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,344 Sq Ft

  33 Remington Rd, Windsor, CT 06095

  33 Remington Rd, Windsor, CT 06095
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  $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,

  

  Mike Albert

  RE/MAX RISE

  (959) 215-6076

  14 Loren Cir, Windsor, CT 06095
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  $1,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Apartment for Rent

  338 Dunfey Ln Unit D, Windsor, CT 06095

  Welcome home to this beautiful condo, a hidden gem nestled right in the heart of Windsor. Just off Exit 37 on I-91, this spacious unit boasts two large bedrooms, a generous dining room, and stunning hardwood floors throughout. Indulge in cooking in the updated kitchen and enjoy the convenience of a shared basement with laundry facilities. Take a relaxing stroll around this peaceful,

  Naihommy Colon Rainbow Realty

  338 Dunfey Ln Unit D, Windsor, CT 06095
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  $395,000 Sold Aug 15, 2025

  33 Mechanic St Unit 204, Windsor, CT 06095

  • 2 Beds
  • 3 Baths
  • 1,677 Sq Ft
  • Built 2006

  Last Sold Summary

  • $236/SF
  • 35 Days On Market

  Current Estimated Value $396,024

  Last Listing Agent Amy Manning William Pitt Sotheby's International Realty

  33 Mechanic St Unit 204, Windsor, CT 06095
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  Est $306,121 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,142 Sq Ft

  7 Lennox Ave, Windsor, CT 06095

  7 Lennox Ave, Windsor, CT 06095
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  $348,900

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

  118 Maple Ave, Windsor, CT 06095

  Welcome to this charming Cape perfectly positioned across from East Rock Park and the Pardee Rose Gardens, offering the ideal blend of comfort, convenience, and natural beauty. As you enter, you will find freshly refinished hardwood floors throughout and a beautifully updated kitchen featuring brand new cabinets, granite countertops, and stainless steel appliances, all filled with natural

  

  Mariana DaSilva

  William Raveis Real Estate

  (860) 791-9717

  118 Maple Ave, Windsor, CT 06095
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  $1,630 - $2,587 total monthly price

  Windsor Station

  Studio - 1 Bed

  69 Mechanic St, Windsor, CT 06095

  Windsor Station is a beloved property located in the heart of Windsor CT . We are walking distance to restaurants, shopping, and entertainment. Hop on the Amtrak or the new CT Rail train right outside of our community doorsteps! We are pet friendly, offering a private dog park for residents with access to the Windsor River Trail and views of the famous Windsor pond. Our unique fitness center has

  69 Mechanic St, Windsor, CT 06095
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  $360,000 Sold Aug 29, 2025

  49 Remington Rd, Windsor, CT 06095

  • 3 Beds
  • 1.5 Baths
  • 1,741 Sq Ft
  • Built 1950

  Last Sold Summary

  • 24% Above List Price
  • $207/SF
  • 3 Days On Market

  Current Estimated Value $350,374

  Last Listing Agent Bonnie Farmer Berkshire Hathaway NE Prop.

  49 Remington Rd, Windsor, CT 06095
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  Est $375,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,465 Sq Ft

  56 Robin Rd, Windsor, CT 06095

  56 Robin Rd, Windsor, CT 06095
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  $299,994 Under Contract

  • 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
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  /22

  $1,900 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 1,020 Sq Ft
  • Apartment for Rent

  244 High Path Rd Unit 244, Windsor, CT 06095

  This 2 bedroom, 2.5 bathroom condominium is available for immediate move-in. The property is located in an end unit within a cul-de-sac in a residential community. On the main level, the unit offers a living area, a dining room, and a half bathroom. The kitchen is equipped with an electric stovetop, refrigerator, and dishwasher. The upper level includes two bedrooms, with the primary bedroom

  Nicole Allen Ardent Trust Property Mngmnt

  244 High Path Rd Unit 244, Windsor, CT 06095
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  $125,000 Sold Oct 02, 2025

  297 High Path Rd Unit 297, Windsor, CT 06095

  • 1 Bed
  • 1.5 Baths
  • 736 Sq Ft
  • Built 1972

  Last Sold Summary

  • 17% Below List Price
  • $170/SF
  • 16 Days On Market

  Last Listing Agent Jessamyn Davila Coldwell Banker Realty

  297 High Path Rd Unit 297, Windsor, CT 06095
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  Est $357,472 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,056 Sq Ft

  15 Stratford Ct, Windsor, CT 06095

  15 Stratford Ct, Windsor, CT 06095
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  $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
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  $1,614 - $2,483 total monthly price

  Rivers Bend

  1 - 2 Beds

  One Phaeton St, Windsor, CT 06095

  River’s Bend Apartments in Windsor, Connecticut sits on a gorgeous 88-acre riverfront. The open spaces, quiet walkways, and picnic spaces add to the comfortable small-town atmosphere. Enjoy the warm sunny days in the resort-style outdoor pool. Farmington River Park is right next door and is a favorite amongst our residents. Last but certainly not least, our central location is close to a

  One Phaeton St, Windsor, CT 06095
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  $430,000 Sold Aug 07, 2025

  30 Holly Cir, Windsor, CT 06095

  • 4 Beds
  • 2.5 Baths
  • 2,522 Sq Ft
  • Built 1966

  Last Sold Summary

  • 1% Above List Price
  • $170/SF
  • 29 Days On Market

  Current Estimated Value $434,302

  Last Listing Agent Michael Price KW Legacy Partners

  30 Holly Cir, Windsor, CT 06095
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  Est $495,911 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,342 Sq Ft

  52 Stage Coach Rd, Windsor, CT 06095

  52 Stage Coach Rd, Windsor, CT 06095
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  /31

  $319,900 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,836 Sq Ft

  55 Foster Ln, Windsor, CT 06095

  Ideally located on a quiet and peaceful cul-de-sac, classic New England charm meets single-level living in this lovely Ranch home. The kitchen features an abundance of white cabinetry, new flooring, an expansive and open dining area, new lighting, and a tile backsplash. Enjoy relaxing while entertaining your guests beside the warmth and glow from the wood burning fireplace in the living room,

  Sharon Rispoli Berkshire Hathaway NE Prop.

  55 Foster Ln, Windsor, CT 06095
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  $1,375 total monthly price

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • House for Rent

  121 Pleasant St, Windsor, CT 06095

  Remodeled apartment in 4 family home. Heat and hot water, water, sewer and trash are included in rent. Tenant responsible for electricity. Must have good credit. 2 months security is requested. 1 cat is ok with pet fee. Owner is related to listing agent.

  Angela Ploszaj Berkshire Hathaway NE Prop.

  121 Pleasant St, Windsor, CT 06095
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  $301,000 Sold May 29, 2025

  185 MacKtown Rd, Windsor, CT 06095

  • 2 Beds
  • 1.5 Baths
  • 1,159 Sq Ft
  • Built 1920

  Last Sold Summary

  • 9% Above List Price
  • $260/SF
  • 1 Day On Market

  Current Estimated Value $307,017

  Last Listing Agent Margaret Douglas William Pitt Sotheby's Int'l

  185 MacKtown Rd, Windsor, CT 06095
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  Est $380,259 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,737 Sq Ft

  2 Haskins Rd, Windsor, CT 06095

  2 Haskins Rd, Windsor, CT 06095
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  $545,000

  • 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
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  /20

  $2,200 per month plus fees

  • 2 Beds
  • 2.5 Baths
  • 1,020 Sq Ft
  • Townhouse for Rent

  266 High Path Rd, Windsor, CT 06095

  Property Id: 2247514Welcome home to this charming 2 bedroom, 2.5 bathroom townhouse in Windsor, CT. Built in 1972, this property features modern amenities such as a dishwasher, washer, and dryer. Enjoy off-street parking, a swimming pool, and on-site laundry. Water, sewage, and garbage included. Don't miss out on this gem! Available starting 11/23/2025 for $2200/month and $3,000 security

  266 High Path Rd, Windsor, CT 06095
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  $452,000 Sold Oct 14, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft
  • Built 1991

  Last Sold Summary

  • 8% Above List Price
  • $231/SF
  • 4 Days On Market

  Last Listing Agent Melissa Rothman eXp Realty

  Unlisted Address
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  Est $420,544 Not Listed For Sale

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

  406 Old Village Cir Unit 406, Windsor, CT 06095

  406 Old Village Cir Unit 406, Windsor, CT 06095

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