Windsor, CT Homes

• 

  $380,000

  Sold Aug 22, 2025

  650 Pigeon Hill Rd, Windsor, CT 06095

  • 3 Beds
  • 1.5 Baths
  • 1,504 Sq Ft
  • Built 1950

  Last Sold Summary

  • 22% Below List Price
  • $253/SF
  • 215 Days On Market

  Current Estimated Value $384,115

  Last Listing Agent Andy Johnson Century 21 AllPoints Realty

  650 Pigeon Hill Rd, Windsor, CT 06095
• 

  Est $446,514

  Not Listed For Sale

  Unlisted Address

  • 5 Beds
  • 2 Baths
  • 2,722 Sq Ft
  • Built 1925

  Unlisted Address

  Last Sold Summary

  • 47 Days On Market
• 

  

  

  /30

  $599,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  318 Capen St, Windsor, CT 06095

  **TO BE BUILT**Fabulous Hopscotch Model New Construction offering a flexible, Open Floor Plan with Modern Finishes throughout. Enjoy 2,160 SF of living space with additional 560 SF of finished lower-level family room or office space-perfect for work-from-home, a media room, or extra living area. The Kitchen features Granite Countertops, a Center Island, Pantry, and Stainless-steel appliances,

  Lori Gabriel Coldwell Banker Realty

  318 Capen St, Windsor, CT 06095
• 

  $303,000

  Sold Jul 22, 2025

  29 Early Dawn Cir, Windsor, CT 06095

  • 2 Beds
  • 1.5 Baths
  • 1,193 Sq Ft
  • Built 1982

  Last Sold Summary

  • 10% Above List Price
  • $254/SF
  • 9 Days On Market

  Current Estimated Value $303,265

  Last Listing Agent Sharon Rispoli Berkshire Hathaway NE Prop.

  29 Early Dawn Cir, Windsor, CT 06095
• 

  Est $383,563

  Not Listed For Sale

  1200 Windsor Ave, Windsor, CT 06095

  • 3 Beds
  • 1.5 Baths
  • 1,644 Sq Ft
  • Built 1915

  1200 Windsor Ave, Windsor, CT 06095

  Last Sold Summary

  • 12 Days On Market
• 

  

  /36

  $269,900

  Pending

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  121 E Barber St, Windsor, CT 06095

  Welcome to 121 E Barber St in desirable Windsor, CT - a beautifully remodeled home offering the perfect blend of comfort, convenience, and family-friendly living. Located right around the corner from a newly updated park, this home is ideal for families looking for both indoor and outdoor space to enjoy. Inside, you'll find recent renovations throughout with stylish new finishes, updated

  Nicholas Burrus Roundtree Realty LLC

  121 E Barber St, Windsor, CT 06095
• 

  $175,000

  Sold Mar 17, 2026

  58 High Path Rd Unit 58, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft
  • Built 1972

  Last Sold Summary

  • $182/SF
  • 6 Days On Market

  Current Estimated Value $177,947

  Last Listing Agent Jacquelyn Santini Ardent Trust Property Mngmnt

  58 High Path Rd Unit 58, Windsor, CT 06095
• 

  Est $284,418

  Not Listed For Sale

  76 N Meadow Rd, Windsor, CT 06095

  • 2 Beds
  • 1 Bath
  • 1,905 Sq Ft
  • Built 1786

  76 N Meadow Rd, Windsor, CT 06095

  Last Sold Summary

  • 48 Days On Market
• 

  

  /40

  $520,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,926 Sq Ft

  86 Carriage Way, Windsor, CT 06095

  Ready to start the new season in your new home? 86 Carriage Way is exactly what you've been looking for. Located in the robust town of Windsor, this traditional colonial meets all your must-haves. Tucked away from the busy road in a tranquil setting, with recent upgrades to the exterior and interior, you will feel right at home. This four-bed, 2.5-bath boost over 2100 sqft with highlights

  Alexander Pryor Coldwell Banker Realty

  86 Carriage Way, Windsor, CT 06095
• 

  $260,000

  Sold Jun 27, 2025

  80 Green Manor Ave, Windsor, CT 06095

  • 3 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Built 1954

  Last Sold Summary

  • 18% Above List Price
  • $236/SF
  • 6 Days On Market

  Current Estimated Value $263,368

  Last Listing Agent Sharon Rispoli Berkshire Hathaway NE Prop.

  80 Green Manor Ave, Windsor, CT 06095
• 

  Est $360,139

  Not Listed For Sale

  33 Mechanic St Unit 312, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,566 Sq Ft
  • Built 2007

  33 Mechanic St Unit 312, Windsor, CT 06095

  Last Sold Summary

  • 25 Days On Market
• 

  

  /24

  $394,499

  • 2 Beds
  • 3 Baths
  • 1,622 Sq Ft

  33 Mechanic St Unit 203, Windsor, CT 06095

  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 features.

  Hawwa Djuned Maria Acuna Real Estate

  33 Mechanic St Unit 203, Windsor, CT 06095
• 

  $385,000

  Sold May 21, 2026

  94 Ludlow Rd, Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 1,578 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Above List Price
  • $244/SF
  • 35 Days On Market

  Current Estimated Value $371,967

  Last Listing Agent Michael Ferris eXp Realty

  94 Ludlow Rd, Windsor, CT 06095
• 

  Est $295,256

  Not Listed For Sale

  33 Mechanic St Unit 311, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,107 Sq Ft
  • Built 2007

  33 Mechanic St Unit 311, Windsor, CT 06095

  Last Sold Summary

  • 2 Days On Market
• 

  

  /36

  $317,500

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,266 Sq Ft

  304 Rood Ave, Windsor, CT 06095

  Picturesque and charming, this three bedroom Cape is nestled on a manicured lot and excudes amazing curb appeal. The southwest orientation of this home brings in a tremedous amount of natural light. Pride of ownership is quite evident and this property is trully in move in condition. A spacious kitchen offers an abundace of cabinets, a built-in hutch and a large dining area. The first flloor

  John Waters Berkshire Hathaway NE Prop.

  304 Rood Ave, Windsor, CT 06095
• 

  $570,000

  Sold Jul 17, 2025

  5 Crabapple Rd, Windsor, CT 06095

  • 4 Beds
  • 4 Baths
  • 2,000 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Above List Price
  • $285/SF
  • 3 Days On Market

  Current Estimated Value $560,204

  Last Listing Agent Diane Kendrick Coldwell Banker Realty

  5 Crabapple Rd, Windsor, CT 06095
• 

  Est $299,092

  Not Listed For Sale

  33 Mechanic St Unit 310, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,107 Sq Ft
  • Built 2007

  33 Mechanic St Unit 310, Windsor, CT 06095

  Last Sold Summary

  • 11 Days On Market
• 

  

  /34

  $354,900

  Pending

  • 3 Beds
  • 2 Baths
  • 1,901 Sq Ft

  167 East St, Windsor, CT 06095

  Welcome to this stunning Contemporary home that features fantastic curb appeal. This fine property offers a versatile flloor plan that accommodates the many living requirements of today's buyers. Upon entering the foyer you will find a very appealing fireplaced living room that offers hardwood floors and a dramatic 18' vaulted ceiling. Flowing off the living room is a large kitchen that features

  John Waters Berkshire Hathaway NE Prop.

  167 East St, Windsor, CT 06095
• 

  $560,000

  Sold Feb 13, 2026

  21 Derek Ln, Windsor, CT 06095

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Below List Price
  • $215/SF
  • 45 Days On Market

  Current Estimated Value $569,780

  Last Listing Agent Allysa DeRosa Mapleridge Realty

  21 Derek Ln, Windsor, CT 06095
• 

  Est $304,112

  Not Listed For Sale

  33 Mechanic St Unit 307, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,111 Sq Ft
  • Built 2007

  33 Mechanic St Unit 307, Windsor, CT 06095

  Last Sold Summary

  • 49 Days On Market
• 

  

  /25

  $290,000

  Under Contract

  • 2 Beds
  • 1 Bath
  • 1,104 Sq Ft

  15 Scarborough Rd, Windsor, CT 06095

  Welcome home to this charming ranch, ideally situated at the end of a quiet cul-de-sac in a desirable Windsor neighborhood. This 2-bedroom, 1-bath home offers comfortable single-level living with numerous recent improvements throughout. Enjoy an updated kitchen, new bamboo flooring throughout most of the home, updated lighting fixtures, and new windows that bring in abundant natural light. Energy

  Carol Parda-Ziolko Carl Guild & Associates

  15 Scarborough Rd, Windsor, CT 06095
• 

  $231,000

  Sold Apr 24, 2026

  39 Warham St, Windsor, CT 06095

  • 3 Beds
  • 1.5 Baths
  • 1,253 Sq Ft
  • Built 1910

  Last Sold Summary

  • 8% Below List Price
  • $184/SF
  • 141 Days On Market

  Current Estimated Value $234,570

  Last Listing Agent Mark Mermelstein eXp Realty

  39 Warham St, Windsor, CT 06095
• 

  Not Listed For Sale

  33 Mechanic St Unit 306, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,597 Sq Ft
  • Built 2007

  33 Mechanic St Unit 306, Windsor, CT 06095

  Last Sold Summary

  • 53 Days On Market
• 

  

  /38

  $375,000

  $10K PRICE DROP Pending

  • 1 Bed
  • 1.5 Baths
  • 1,868 Sq Ft

  66 Maple Ave, Windsor, CT 06095

  Welcome to a truly unique residential opportunity offering the perfect blend of living and flexible workspace. This well-maintained home features a private upstairs apartment designed for everyday living, space you need to feel right at home. On the main level, you'll find four generously sized rooms currently configured as professional offices, along with a spacious waiting area. Whether you

  Diane Cordiliko Realty One Group Cutting Edge

  66 Maple Ave, Windsor, CT 06095
• 

  $337,000

  Sold Dec 09, 2025

  107 Sunnyfield Dr, Windsor, CT 06095

  • 3 Beds
  • 2.5 Baths
  • 1,352 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Above List Price
  • $249/SF
  • 33 Days On Market

  Current Estimated Value $354,105

  Last Listing Agent Ben Castonguay Sentry Real Estate

  107 Sunnyfield Dr, Windsor, CT 06095
• 

  Est $361,445

  Not Listed For Sale

  33 Mechanic St Unit 305, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,579 Sq Ft
  • Built 2006

  33 Mechanic St Unit 305, Windsor, CT 06095

  Last Sold Summary

  • 4 Days On Market
• 

  

  /16

  $339,000

  Under Contract

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

  39 Loren Cir, Windsor, CT 06095

  Welcome to this 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.

  Lavasha Bester CENTURY 21 AllPoints Realty

  39 Loren Cir, Windsor, CT 06095
• 

  $370,000

  Sold Sep 22, 2025

  19 Cardston Cir, Windsor, CT 06095

  • 5 Beds
  • 3 Baths
  • 2,406 Sq Ft
  • Built 1970

  Last Sold Summary

  • 5% Below List Price
  • $154/SF
  • 76 Days On Market

  Current Estimated Value $394,445

  Last Listing Agent Benita Reaves Berkshire Hathaway NE Prop.

  19 Cardston Cir, Windsor, CT 06095
• 

  Est $312,563

  Not Listed For Sale

  33 Mechanic St Unit 303, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 2006

  33 Mechanic St Unit 303, Windsor, CT 06095

  Last Sold Summary

  • 31 Days On Market
• 

  

  /6

  $569,900

  New Construction Under Contract

  • 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
• 

  $520,500

  Sold May 22, 2026

  453 Tributary Ln, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,863 Sq Ft
  • Built 2008

  Last Sold Summary

  • 17% Above List Price
  • $279/SF
  • 4 Days On Market

  Current Estimated Value $440,745

  Last Listing Agent Sharon Rispoli Berkshire Hathaway NE Prop.

  453 Tributary Ln, Windsor, CT 06095
• 

  Est $373,772

  Not Listed For Sale

  33 Mechanic St Unit 206, Windsor, CT 06095

  • 2 Beds
  • 3 Baths
  • 1,745 Sq Ft
  • Built 2006

  33 Mechanic St Unit 206, Windsor, CT 06095

  Last Sold Summary

  • 47 Days On Market
• 

  

  /37

  $317,500

  $33K PRICE DROP Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,828 Sq Ft

  18 Chelsea Ln, Windsor, CT 06095

  Opportunity knocks! This spacious colonial sits at the end of the cul-de-sac on a private wooded lot in an established neighborhood. Minutes to I-91, Bradley International Airport and all the amenities, yet set away from all the hustle and bustle. This home will need plenty of updates and work, but offers so much potential for just the right buyer! Personal property may remain. As-is.

  Minna Reid Reid Real Estate Group

  18 Chelsea Ln, Windsor, CT 06095
• 

  $420,000

  Sold Apr 15, 2026

  105 Trent Dr, Windsor, CT 06095

  • 4 Beds
  • 2.5 Baths
  • 1,960 Sq Ft
  • Built 1969

  Last Sold Summary

  • 1% Below List Price
  • $214/SF
  • 6 Days On Market

  Current Estimated Value $422,217

  Last Listing Agent William Eidt Realty One Group Cutting Edge

  105 Trent Dr, Windsor, CT 06095
• 

  Est $376,674

  Not Listed For Sale

  33 Mechanic St Unit 201, Windsor, CT 06095

  • 2 Beds
  • 3 Baths
  • 1,700 Sq Ft
  • Built 2006

  33 Mechanic St Unit 201, Windsor, CT 06095

  Last Sold Summary

  • 21 Days On Market
• 

  

  /33

  $374,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,515 Sq Ft

  10 Scherer Ln, Windsor, CT 06095

  HIGHEST & BEST - Monday 6/15 @ 11:59 p.m. (midnight). Welcome to Scherer Ridge Estates, Windsor's sought-after 55+ community! This well maintained 3-bedroom, 2-full-bath ranch offers comfortable one-level living with an oversized attached 2-car garage and a bright, open floor plan enhanced by an abundance of windows. The eat-in kitchen features a newer stainless-steel refrigerator and dishwasher

  Jacqueline Grier William Raveis Real Estate

  10 Scherer Ln, Windsor, CT 06095
• 

  $343,000

  Sold Jun 23, 2026

  249 Preston St, Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Above List Price
  • $297/SF
  • 63 Days On Market

  Current Estimated Value $337,078

  Last Listing Agent Michelle Grant Coldwell Banker Premier Real Estate

  249 Preston St, Windsor, CT 06095
• 

  Est $353,940

  Not Listed For Sale

  33 Mechanic St Unit 117, Windsor, CT 06095

  • 2 Beds
  • 2.5 Baths
  • 1,575 Sq Ft
  • Built 2007

  33 Mechanic St Unit 117, Windsor, CT 06095

  Last Sold Summary

  • 27 Days On Market
• 

  

  /33

  $650,000

  New Construction Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,914 Sq Ft

  857 Stone Rd, Windsor, CT 06095

  Discover the perfect blend of comfort, convenience, and modern design in this stunning new construction Colonial set on nearly 1.5 acres in a peaceful Farming area. Ideally located near major highways and an international airport, this home offers effortless access to everything you need-just 30 minutes to Hartford, 20 minutes to Springfield, MA, 1.5 hours to Boston, and 2 hours to New York City.

  Gina McDonald William Raveis Real Estate

  857 Stone Rd, Windsor, CT 06095
• 

  $338,000

  Sold Feb 09, 2026

  14 Sage Park Rd, Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 1,578 Sq Ft
  • Built 1945

  Last Sold Summary

  • 1% Below List Price
  • $214/SF
  • 12 Days On Market

  Current Estimated Value $337,419

  Last Listing Agent Clyde Crosby Inventive Realty LLC

  14 Sage Park Rd, Windsor, CT 06095

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