Windsor, CT Homes

• 

  $410,000

  Sold May 28, 2026

  36 Pilgrim Dr, Windsor, CT 06095

  • 4 Beds
  • 2 Baths
  • 1,526 Sq Ft
  • Built 1959

  Last Sold Summary

  • 7% Above List Price
  • $269/SF
  • 4 Days On Market

  Current Estimated Value $403,544

  Last Listing Agent Sharon Rispoli Berkshire Hathaway NE Prop.

  36 Pilgrim Dr, Windsor, CT 06095
• 

  Est $292,705

  Not Listed For Sale

  103 Woodland St, Windsor, CT 06095

  • 3 Beds
  • 1 Bath
  • 1,197 Sq Ft
  • Built 1953

  103 Woodland St, Windsor, CT 06095

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Edgar Nava Maple Vale Realty LLC
• 

  

  

  /28

  $279,900

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,826 Sq Ft

  621 Kennedy Rd, Windsor, CT 06095

  Embrace the opportunity to make your dream a reality with this spacious, three bedroom Raised Ranch home and its unlimited potential. Spacious and bright, the kitchen offers the convenience of a dine-in area, a door to the deck and has been updated with new flooring. Inviting and open to the dining room, the living room is highlighted by a wood burning fireplace and a large picture window that

  Sharon Rispoli Berkshire Hathaway NE Prop.

  621 Kennedy Rd, Windsor, CT 06095
• 

  $374,000

  Sold May 22, 2026

  44 Maple Ave, Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft
  • Built 1872

  Last Sold Summary

  • 2% Below List Price
  • $241/SF
  • 10 Days On Market

  Current Estimated Value $374,018

  Last Listing Agent Barbara Clerice Elite Legacy Realty LLC

  44 Maple Ave, Windsor, CT 06095
• 

  Est $291,213

  Not Listed For Sale

  45 Seymour St, Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Built 1940

  45 Seymour St, Windsor, CT 06095

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Raymond Malcolm Cornerstone Homes Plus, Inc.
• 

  

  /40

  $349,000

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  5 Rhodora Terrace Unit 5, Windsor, CT 06095

  Picture your mornings here: coffee in hand on the deck, the kind of quiet that makes you want to linger before the day even starts. Welcome to 5 Rhodora Terrace, a standout townhome in Windsor's sought after neighborhood, offering over 1,500 sq-ft that was built for how you actually want to live. The open living and dining area practically begs for a dinner party, and the kitchen's breakfast nook

  Konrad Krukowski Ryze Realty Group LLC

  5 Rhodora Terrace Unit 5, Windsor, CT 06095
• 

  $330,000

  Sold Sep 19, 2025

  287 Deerfield Rd, Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 1,075 Sq Ft
  • Built 1945

  Last Sold Summary

  • 10% Above List Price
  • $307/SF
  • 7 Days On Market

  Current Estimated Value $320,751

  Last Listing Agent Sharon Rispoli Berkshire Hathaway NE Prop.

  287 Deerfield Rd, Windsor, CT 06095
• 

  Est $326,131

  Not Listed For Sale

  67 Woodland St, Windsor, CT 06095

  • 4 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1950

  67 Woodland St, Windsor, CT 06095

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Donna Genovese Great Estates, CT
• 

  

  /16

  $265,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,138 Sq Ft

  5 David Cir, Windsor, CT 06095

  Opportunity knocks at 5 David Circle in Windsor. This 3-bedroom, 1-bath raised ranch has an attached 1-car garage, and an unfinished lower level with plenty of potential for additional living space, storage, or a workshop. Situated on a quiet cul-de-sac, the home features a spacious backyard, vinyl siding, and a functional layout ready for your vision. The interior is in need of updating and

  Mark Mermelstein eXp Realty

  5 David Cir, Windsor, CT 06095
• 

  $324,900

  Sold Dec 01, 2025

  8 Aramamet St, Windsor, CT 06095

  • 4 Beds
  • 1 Bath
  • 1,305 Sq Ft
  • Built 1920

  Last Sold Summary

  • 7% Below List Price
  • $249/SF
  • 53 Days On Market

  Current Estimated Value $319,929

  Last Listing Agent Gregory Wright Great Estates, CT

  8 Aramamet St, Windsor, CT 06095
• 

  Est $346,118

  Not Listed For Sale

  4 David Cir, Windsor, CT 06095

  • 4 Beds
  • 1.5 Baths
  • 1,638 Sq Ft
  • Built 1978

  4 David Cir, Windsor, CT 06095

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Brian Jackson Elite Team Realty, LLC
• 

  

  /40

  $569,900

  Under Contract

  • 6 Beds
  • 3.5 Baths
  • 4,643 Sq Ft

  117 Hollow Brook Rd, Windsor, CT 06095

  Welcome to 117 Hollow Brook Road, an exceptional Colonial nestled in the highly desirable Poquonock section of Windsor. Offering over 4,200 square feet of thoughtfully designed living space, this beautifully maintained home combines comfort, versatility and a rare opportunity for multi-generational living. Freshly painted throughout, the home welcomes you with a bright inviting interior. The

  Gail Gene Mercey Berkshire Hathaway NE Prop.

  117 Hollow Brook Rd, Windsor, CT 06095
• 

  $290,000

  Sold Apr 02, 2026

  1035 N Worthy St, Windsor, CT 06095

  • 3 Beds
  • 1 Bath
  • 1,085 Sq Ft
  • Built 1951

  Last Sold Summary

  • $267/SF
  • 33 Days On Market

  Current Estimated Value $290,226

  Last Listing Agent Raymond Romero Five Stars Realty

  1035 N Worthy St, Windsor, CT 06095
• 

  Est $294,449

  Not Listed For Sale

  34 Woodland St, Windsor, CT 06095

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1952

  34 Woodland St, Windsor, CT 06095

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Rose Elias Coldwell Banker Realty
• 

  

  /21

  $339,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,415 Sq Ft

  632 Locksmith Unit 632, Windsor, CT 06095

  Welcome to Stockbridge, one of Windsor's best-kept secrets! Nestled within a beautifully maintained community featuring a variety of thoughtfully designed condominium styles, this exceptional ranch offers the ease of one-floor living without sacrificing space or comfort. Step inside to discover soaring ceilings, an inviting open floor plan, and an abundance of natural light that creates a warm,

  Stephanie Stone William Raveis/First Town RE

  632 Locksmith Unit 632, Windsor, CT 06095
• 

  $610,000

  Sold May 06, 2026

  24 Mary Catherine Cir, Windsor, CT 06095

  • 4 Beds
  • 3.5 Baths
  • 2,878 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Above List Price
  • $212/SF
  • 48 Days On Market

  Current Estimated Value $613,021

  Last Listing Agent Susan Wiley Berkshire Hathaway NE Prop.

  24 Mary Catherine Cir, Windsor, CT 06095
• 

  Est $279,477

  Not Listed For Sale

  48 Highland Ave, Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 989 Sq Ft
  • Built 1950

  48 Highland Ave, Windsor, CT 06095

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent John Laplante William Raveis Real Estate
• 

  

  /25

  $389,900

  • 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
• 

  $540,000

  Sold Dec 19, 2025

  225 Rollingbrook, Windsor, CT 06095

  • 4 Beds
  • 2.5 Baths
  • 2,838 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Above List Price
  • $190/SF
  • 7 Days On Market

  Current Estimated Value $545,977

  Last Listing Agent Sharon Rispoli Berkshire Hathaway NE Prop.

  225 Rollingbrook, Windsor, CT 06095
• 

  Est $330,270

  Not Listed For Sale

  155 Deerfield Rd, Windsor, CT 06095

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft
  • Built 1954

  155 Deerfield Rd, Windsor, CT 06095

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Michael Zizzamia William Raveis Real Estate
• 

  

  /38

  $635,000

  New Construction

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

  823 Stone Rd, Windsor, CT 06095

  Imagine pulling into your driveway, greeted by open fields and the quiet charm of farmland - yet knowing you're just minutes from Bradley International Airport and major highways. Here, you can enjoy peaceful country living while staying under 30 minutes to Hartford and Springfield, and within two hours of Boston and New York City. Step inside the home you helped design, built by Fauteux

  Gina McDonald William Raveis Real Estate

  823 Stone Rd, Windsor, CT 06095
• 

  $450,000

  Sold Nov 07, 2025

  322 Deerfield Rd, Windsor, CT 06095

  • 5 Beds
  • 2 Baths
  • 2,709 Sq Ft
  • Built 1933

  Last Sold Summary

  • $166/SF
  • 46 Days On Market

  Current Estimated Value $450,101

  Last Listing Agent Shari Jones Coldwell Banker Realty

  322 Deerfield Rd, Windsor, CT 06095
• 

  Est $276,719

  Not Listed For Sale

  1920 Logans Way, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,328 Sq Ft
  • Built 2003

  1920 Logans Way, Windsor, CT 06095

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Sharon Rispoli Berkshire Hathaway NE Prop.
• 

  

  /28

  $320,000

  $30K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 4,585 Sq Ft

  245 Deerfield Rd, Windsor, CT 06095

  Price Improvement! Own a piece of history in this 1796 colonial, built by Elisha Moore, a 4-unit investment property on .77 acre. Included a one-car garage with bay, a loft above the garage that can be used for crafting, office, man's cave, storage, or additional income, with plenty of parking for tenants/guests. This current owner started renovations, but could not complete them. When the home

  Maria Aubey Silver and Oak Realty

  245 Deerfield Rd, Windsor, CT 06095
• 

  $370,000

  Sold Oct 17, 2025

  33 Nod Rd, Windsor, CT 06095

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft
  • Built 1957

  Last Sold Summary

  • 6% Above List Price
  • $222/SF
  • 6 Days On Market

  Current Estimated Value $368,393

  Last Listing Agent Catherine Rockoff Rockoff Realty

  33 Nod Rd, Windsor, CT 06095
• 

  Est $254,556

  Not Listed For Sale

  144 Midian Ave, Windsor, CT 06095

  • 3 Beds
  • 1 Bath
  • 1,222 Sq Ft
  • Built 1934

  144 Midian Ave, Windsor, CT 06095

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Martha Calciano Century 21 AllPoints Realty
• 

  

  /25

  $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
• 

  $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 $385,296

  Last Listing Agent Andy Johnson Century 21 AllPoints Realty

  650 Pigeon Hill Rd, Windsor, CT 06095
• 

  Est $205,702

  Not Listed For Sale

  32 Midian Ave, Windsor, CT 06095

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

  32 Midian Ave, Windsor, CT 06095

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Will Gonzalez iVision Real Estate
• 

  

  /21

  $389,900

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,525 Sq Ft

  135 East St, Windsor, CT 06095

  What an amazing home that is move in ready, enjoy new kitchen and bathrooms, windows, new flooring throughout and much more.

  Helton Dornelas Golden Rule Realty

  135 East St, Windsor, CT 06095
• 

  $375,000

  Sold Jul 30, 2026

  141 Rood Ave, Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Above List Price
  • $287/SF
  • 25 Days On Market

  Current Estimated Value $369,408

  Last Listing Agent Shy Grahame Berkshire Hathaway NE Prop.

  141 Rood Ave, Windsor, CT 06095
• 

  Est $474,668

  Not Listed For Sale

  88 Joshua Hill, Windsor, CT 06095

  • 3 Beds
  • 3 Baths
  • 2,343 Sq Ft
  • Built 2000

  88 Joshua Hill, Windsor, CT 06095

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Darlene Arter Berkshire Hathaway NE Prop.
• 

  

  /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
• 

  $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 $177,235

  Last Listing Agent Jacquelyn Santini Ardent Trust Property Mngmnt

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

  Est $430,061

  Not Listed For Sale

  211 Portman St, Windsor, CT 06095

  • 4 Beds
  • 2 Baths
  • 2,094 Sq Ft
  • Built 1954

  211 Portman St, Windsor, CT 06095

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Begum Abadin eXp Realty
• 

  

  /29

  $425,000

  • 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
• 

  $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 $379,299

  Last Listing Agent Michael Ferris eXp Realty

  94 Ludlow Rd, Windsor, CT 06095
• 

  Est $433,756

  Not Listed For Sale

  32 Joshua Hill, Windsor, CT 06095

  • 3 Beds
  • 2 Baths
  • 1,976 Sq Ft
  • Built 1991

  32 Joshua Hill, Windsor, CT 06095

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Katrina Pratt Rainbow Realty
• 

  

  /38

  $435,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  66 Country Club Dr, Windsor, CT 06095

  This well-maintained 4-bedroom, 2.5-bath Colonial sits on nearly half an acre, offering a spacious and level backyard perfect for outdoor enjoyment. A deck off the rear of the home provides an ideal space for relaxing or entertaining. Inside, the first floor features a thoughtfully designed layout with a bright eat-in kitchen, along with a comfortable living room, formal dining room, and a

  Andy Johnson Century 21 AllPoints Realty

  66 Country Club Dr, 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 $569,410

  Last Listing Agent Allysa DeRosa Mapleridge Realty

  21 Derek Ln, Windsor, CT 06095

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