1,469

Recently Sold Windham County CT Homes

Section Image
  • 140 Groveland Ave, Putnam, CT 06260

    $440,000 Sold May 16, 2025

    140 Groveland Ave, Putnam, CT 06260

    • 3 Beds
    • 3.5 Baths
    • 2,429 Sq Ft
    • Built 2012

    Last Sold Summary

    • $181/SF
    • 13 Days On Market

    Current Estimated Value $469,525

    Last Listing Agent Georgi Morin S.C.E. Real Estate

    140 Groveland Ave, Putnam, CT 06260
  • 153 Bluebird Ln, Brooklyn, CT 06234

    $545,000 Sold Jan 09, 2026

    153 Bluebird Ln, Brooklyn, CT 06234

    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $345/SF
    • 46 Days On Market

    Last Listing Agent Mark Tetreault, II RE/MAX Bell Park Realty

    153 Bluebird Ln, Brooklyn, CT 06234
  • 7 Shelby Cir, Dayville, CT 06241

    $310,000 Sold Feb 13, 2026

    7 Shelby Cir, Dayville, CT 06241

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1989

    Last Sold Summary

    • 5% Below List Price
    • $323/SF
    • 91 Days On Market

    Current Estimated Value $310,249

    Last Listing Agent Carol Ryniewicz CR Premier Properties

    7 Shelby Cir, Dayville, CT 06241
  • 409 Main St, Danielson, CT 06239

    $460,000 Sold Jan 16, 2026

    409 Main St, Danielson, CT 06239

    • 8 Beds
    • 5.5 Baths
    • 4,670 Sq Ft
    • Built 1800

    Last Sold Summary

    • 16% Below List Price
    • $99/SF
    • 56 Days On Market

    Current Estimated Value $459,437

    Last Listing Agent Michael Hvizdo Coldwell Banker Realty

    409 Main St, Danielson, CT 06239
  • 121 Highland View Dr, Windham, CT 06266

    $50,000 Sold Sep 26, 2025

    121 Highland View Dr, Windham, CT 06266

    • Land
    • 0.92 Acre
    • $54,348 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 8 Days On Market

    Last Listing Agent Jeanne Crum Home Selling Team

    121 Highland View Dr, Windham, CT 06266
  • 256 Pine Hill Rd, Sterling, CT 06377

    $135,000 Sold Aug 18, 2025

    256 Pine Hill Rd, Sterling, CT 06377

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft
    • Built 1955

    Last Sold Summary

    • 4% Above List Price
    • $188/SF
    • 5 Days On Market

    Current Estimated Value $145,081

    Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

    256 Pine Hill Rd, Sterling, CT 06377
  • 245 Brooklyn Rd, Canterbury, CT 06331

    $725,000 Sold Jan 23, 2026

    245 Brooklyn Rd, Canterbury, CT 06331

    • 4 Beds
    • 2.5 Baths
    • 3,285 Sq Ft
    • Built 1787

    Last Sold Summary

    • 8% Below List Price
    • $221/SF
    • 64 Days On Market

    Current Estimated Value $719,618

    Last Listing Agent Cary Marcoux RE/MAX Bell Park Realty

    245 Brooklyn Rd, Canterbury, CT 06331
  • 43 Hiawatha Heights, Woodstock Valley, CT 06282

    $789,000 Sold Aug 15, 2025

    43 Hiawatha Heights, Woodstock Valley, CT 06282

    • 2 Beds
    • 2 Baths
    • 1,918 Sq Ft
    • Built 1988

    Last Sold Summary

    • $411/SF
    • 42 Days On Market

    Current Estimated Value $803,500

    Last Listing Agent Jennie Kesselman Berkshire Hathaway NE Prop.

    43 Hiawatha Heights, Woodstock Valley, CT 06282
  • 16 Porter Plain Rd, Thompson, CT 06277

    $400,000 Sold Oct 03, 2025

    16 Porter Plain Rd, Thompson, CT 06277

    • 3 Beds
    • 2 Baths
    • 1,960 Sq Ft
    • Built 1974

    Last Sold Summary

    • 5% Above List Price
    • $204/SF
    • 3 Days On Market

    Current Estimated Value $407,474

    Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

    16 Porter Plain Rd, Thompson, CT 06277
  • 5 Chappell St, Chaplin, CT 06235

    $355,000 Sold Jan 14, 2026

    5 Chappell St, Chaplin, CT 06235

    • 3 Beds
    • 2.5 Baths
    • 1,748 Sq Ft
    • Built 1954

    Last Sold Summary

    • 3% Above List Price
    • $203/SF
    • 53 Days On Market

    Current Estimated Value $344,419

    Last Listing Agent Gregory Hanner Garden Realty

    5 Chappell St, Chaplin, CT 06235
  • 50 Crooked Trail, Woodstock, CT 06281

    $395,000 Sold Nov 03, 2025

    50 Crooked Trail, Woodstock, CT 06281

    • 3 Beds
    • 3 Baths
    • 2,339 Sq Ft
    • Built 1993

    Last Sold Summary

    • 6% Below List Price
    • $169/SF
    • 16 Days On Market

    Current Estimated Value $437,451

    Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

    50 Crooked Trail, Woodstock, CT 06281
  • 10 School Street Extension, Plainfield, CT 06374

    $399,000 Sold Feb 20, 2026

    10 School Street Extension, Plainfield, CT 06374

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft
    • Built 2025

    Last Sold Summary

    • 13% Below List Price
    • $219/SF
    • 63 Days On Market

    Last Listing Agent Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    10 School Street Extension, Plainfield, CT 06374
  • 0 Lustig Rd, Ashford, CT 06278

    $80,000 Sold Aug 29, 2025

    0 Lustig Rd, Ashford, CT 06278

    • Land
    • 13.18 Acres
    • $6,070 per Acre

    Last Sold Summary

    • 6% Below List Price
    • 10 Days On Market

    Last Listing Agent Amy Rio Executive Real Estate Inc.

    0 Lustig Rd, Ashford, CT 06278
  • 1 First St, North Grosvenordale, CT 06255

    $365,000 Sold Dec 22, 2025

    1 First St, North Grosvenordale, CT 06255

    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft
    • Built 2025

    Last Sold Summary

    • 9% Below List Price
    • $203/SF
    • 233 Days On Market

    Current Estimated Value $365,267

    Last Listing Agent Amy Brunet Brunet and Company Real Estate

    1 First St, North Grosvenordale, CT 06255
  • 4 Gifford Ave, Willimantic, CT 06226

    $219,900 Sold Jun 02, 2025

    4 Gifford Ave, Willimantic, CT 06226

    • 3 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Built 1971

    Last Sold Summary

    • $212/SF
    • 27 Days On Market

    Current Estimated Value $228,621

    Last Listing Agent Dennis Golden Real Broker CT, LLC

    4 Gifford Ave, Willimantic, CT 06226
  • 5 Mortimer Rd, Moosup, CT 06354

    $305,000 Sold May 29, 2025

    5 Mortimer Rd, Moosup, CT 06354

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft
    • Built 1984

    Last Sold Summary

    • 5% Above List Price
    • $279/SF
    • 3 Days On Market

    Current Estimated Value $317,884

    Last Listing Agent Christine Johnson RE/MAX One

    5 Mortimer Rd, Moosup, CT 06354
  • 1212 Norwich Rd, Plainfield, CT 06374

    $295,000 Sold May 23, 2025

    1212 Norwich Rd, Plainfield, CT 06374

    • 3 Beds
    • 2 Baths
    • 1,519 Sq Ft
    • Built 1807

    Last Sold Summary

    • $194/SF
    • 22 Days On Market

    Current Estimated Value $319,314

    Last Listing Agent Tanya McDermott Berkshire Hathaway NE Prop.

    1212 Norwich Rd, Plainfield, CT 06374
  • 269 Jackson St, Willimantic, CT 06226

    $290,000 Sold Oct 01, 2025

    269 Jackson St, Willimantic, CT 06226

    • 3 Beds
    • 3 Baths
    • 2,382 Sq Ft
    • Built 1910

    Last Sold Summary

    • $122/SF
    • 47 Days On Market

    Current Estimated Value $292,081

    Last Listing Agent Michael A Tarallo Giner Real Estate

    269 Jackson St, Willimantic, CT 06226
  • 25 Route 197 Unit Lot 40, Woodstock, CT 06281

    $26,000 Sold Oct 08, 2025

    25 Route 197 Unit Lot 40, Woodstock, CT 06281

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft
    • Built 1995

    Last Sold Summary

    • 42% Below List Price
    • $87/SF
    • 168 Days On Market

    Last Listing Agent Keri Roy Kazantzis Real Estate, LLC

    25 Route 197 Unit Lot 40, Woodstock, CT 06281
  • 0 Seckar Rd Unit 24034213, Ashford, CT 06278

    $95,000 Sold Sep 24, 2025

    0 Seckar Rd Unit 24034213, Ashford, CT 06278

    • Land
    • 3.68 Acres
    • $25,815 per Acre

    Last Sold Summary

    • 21% Below List Price
    • 420 Days On Market

    Last Listing Agent Jeff Main Berkshire Hathaway NE Prop.

    0 Seckar Rd Unit 24034213, Ashford, CT 06278
  • 100 South St, Willimantic, CT 06226

    $300,000 Sold Nov 13, 2025

    100 South St, Willimantic, CT 06226

    • 6 Beds
    • 2 Baths
    • 1,932 Sq Ft
    • Built 1914

    Last Sold Summary

    • $155/SF
    • 85 Days On Market

    Current Estimated Value $305,891

    Last Listing Agent Amber Jones KW Legacy Partners

    100 South St, Willimantic, CT 06226
  • 69 Peckham Ln, Danielson, CT 06239

    $330,000 Sold Jan 23, 2026

    69 Peckham Ln, Danielson, CT 06239

    • 4 Beds
    • 3.5 Baths
    • 3,523 Sq Ft
    • Built 1930

    Last Sold Summary

    • 10% Above List Price
    • $94/SF
    • 112 Days On Market

    Current Estimated Value $337,564

    Last Listing Agent Mary Collins Berkshire Hathaway NE Prop.

    69 Peckham Ln, Danielson, CT 06239
  • 19 Harrison St, Putnam, CT 06260

    $320,000 Sold Jun 25, 2025

    19 Harrison St, Putnam, CT 06260

    • 3 Beds
    • 1 Bath
    • 1,224 Sq Ft
    • Built 1977

    Last Sold Summary

    • 2% Above List Price
    • $261/SF
    • 5 Days On Market

    Current Estimated Value $333,130

    Last Listing Agent Tanya McDermott Berkshire Hathaway NE Prop.

    19 Harrison St, Putnam, CT 06260
  • 93 Jericho Rd, Pomfret Center, CT 06259

    $504,700 Sold Jan 05, 2026

    93 Jericho Rd, Pomfret Center, CT 06259

    • 3 Beds
    • 2 Baths
    • 1,884 Sq Ft
    • Built 1975

    Last Sold Summary

    • 1% Below List Price
    • $268/SF
    • 16 Days On Market

    Current Estimated Value $499,927

    Last Listing Agent Ryan LaJoie Johnston & Associates Real Estate, LLC

    93 Jericho Rd, Pomfret Center, CT 06259
  • 287 N Sterling Rd, Sterling, CT 06377

    $610,000 Sold Jul 11, 2025

    287 N Sterling Rd, Sterling, CT 06377

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 2022

    Last Sold Summary

    • 19% Below List Price
    • $434/SF
    • 10 Days On Market

    Current Estimated Value $612,402

    Last Listing Agent Daniel Deojay RE/MAX Bell Park Realty

    287 N Sterling Rd, Sterling, CT 06377
  • 170 Lyon Hill Rd, Woodstock, CT 06281

    $700,000 Sold Nov 19, 2025

    170 Lyon Hill Rd, Woodstock, CT 06281

    • 3 Beds
    • 2.5 Baths
    • 2,960 Sq Ft
    • Built 1811

    Last Sold Summary

    • 3% Above List Price
    • $236/SF
    • 2 Days On Market

    Current Estimated Value $701,790

    Last Listing Agent Mary Ellen Barnett William Pitt Sotheby's Int'l

    170 Lyon Hill Rd, Woodstock, CT 06281
  • 156 Quaddick Rd, Thompson, CT 06277

    $470,000 Sold Sep 12, 2025

    156 Quaddick Rd, Thompson, CT 06277

    • 3 Beds
    • 2 Baths
    • 1,836 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Above List Price
    • $256/SF
    • 10 Days On Market

    Current Estimated Value $464,974

    Last Listing Agent Ryan LaJoie Johnston & Associates Real Estate, LLC

    156 Quaddick Rd, Thompson, CT 06277
  • 449 E Thompson Rd, Thompson, CT 06277

    $560,000 Sold Jul 01, 2025

    449 E Thompson Rd, Thompson, CT 06277

    • 3 Beds
    • 2.5 Baths
    • 2,132 Sq Ft
    • Built 1989

    Last Sold Summary

    • 2% Below List Price
    • $263/SF
    • 12 Days On Market

    Current Estimated Value $548,605

    Last Listing Agent Rachel Sposato Berkshire Hathaway NE Prop.

    449 E Thompson Rd, Thompson, CT 06277
  • 80 Ventura Dr, Brooklyn, CT 06234

    $350,000 Sold Dec 17, 2025

    80 Ventura Dr, Brooklyn, CT 06234

    • 2 Beds
    • 2 Baths
    • 1,908 Sq Ft
    • Built 1982

    Last Sold Summary

    • 8% Below List Price
    • $183/SF
    • 155 Days On Market

    Current Estimated Value $350,843

    Last Listing Agent Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    80 Ventura Dr, Brooklyn, CT 06234
  • 23 Little Bungee Hill Rd, Woodstock Valley, CT 06282

    $559,000 Sold Feb 02, 2026

    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282

    • 4 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1960

    Last Sold Summary

    • 11% Below List Price
    • $259/SF
    • 198 Days On Market

    Current Estimated Value $544,197

    Last Listing Agent Alan Berman Signature Properties of N.E.

    23 Little Bungee Hill Rd, Woodstock Valley, CT 06282
  • 11 Stone House Dr, Plainfield, CT 06374

    $425,000 Sold Feb 27, 2026

    11 Stone House Dr, Plainfield, CT 06374

    • 3 Beds
    • 2 Baths
    • 1,832 Sq Ft
    • Built 2017

    Last Sold Summary

    • 2% Below List Price
    • $232/SF
    • 80 Days On Market

    Last Listing Agent Joan Casey RE/MAX Legends

    11 Stone House Dr, Plainfield, CT 06374
  • 625 Riverside Dr, North Grosvenordale, CT 06255

    $430,000 Sold Jun 30, 2025

    625 Riverside Dr, North Grosvenordale, CT 06255

    • 4 Beds
    • 2 Baths
    • 2,271 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Above List Price
    • $189/SF
    • 8 Days On Market

    Current Estimated Value $437,620

    Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

    625 Riverside Dr, North Grosvenordale, CT 06255
  • 72 Old Canterbury Rd, Hampton, CT 06247

    $430,000 Sold Aug 21, 2025

    72 Old Canterbury Rd, Hampton, CT 06247

    • 3 Beds
    • 2 Baths
    • 2,508 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Below List Price
    • $171/SF
    • 82 Days On Market

    Current Estimated Value $440,376

    Last Listing Agent Jennifer Lehto Kazantzis Real Estate, LLC

    72 Old Canterbury Rd, Hampton, CT 06247
  • 10 Ralph St, Moosup, CT 06354

    $335,000 Sold Nov 21, 2025

    10 Ralph St, Moosup, CT 06354

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1962

    Last Sold Summary

    • 7% Below List Price
    • $317/SF
    • 17 Days On Market

    Current Estimated Value $336,553

    Last Listing Agent Ashley Walker Kazantzis Real Estate, LLC

    10 Ralph St, Moosup, CT 06354
  • 7 Lockwood St, Brooklyn, CT 06234

    $338,000 Sold Mar 06, 2026

    7 Lockwood St, Brooklyn, CT 06234

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft
    • Built 1959

    Last Sold Summary

    • 2% Above List Price
    • $241/SF
    • 49 Days On Market

    Current Estimated Value $326,967

    Last Listing Agent Shawn Mercer Coldwell Banker Realty

    7 Lockwood St, Brooklyn, CT 06234
  • 35-37 N Chestnut St, Plainfield, CT 06374

    $367,000 Sold Jun 02, 2025

    35-37 N Chestnut St, Plainfield, CT 06374

    • 6 Beds
    • 2 Baths
    • 2,331 Sq Ft
    • Built 1860

    Last Sold Summary

    • 2% Above List Price
    • $157/SF
    • 27 Days On Market

    Current Estimated Value $372,031

    Last Listing Agent Karly Worth Call It Closed Realty

    35-37 N Chestnut St, Plainfield, CT 06374
  • 47 Insalaco Dr, Windham, CT 06280

    $379,900 Sold Dec 09, 2025

    47 Insalaco Dr, Windham, CT 06280

    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft
    • Built 1970

    Last Sold Summary

    • $180/SF
    • 30 Days On Market

    Current Estimated Value $380,325

    Last Listing Agent Karan Garewal Winwin Realty

    47 Insalaco Dr, Windham, CT 06280
  • Unlisted Address

    $160,000 Sold May 20, 2025

    Unlisted Address

    • Land
    • 16.75 Acres
    • $9,552 per Acre

    Last Sold Summary

    • 54% Below List Price
    • 241 Days On Market

    Last Listing Agent Clarence Russ Home Selling Team

    Unlisted Address
  • 10 Tiffany St, Brooklyn, CT 06234

    $279,900 Sold Aug 25, 2025

    10 Tiffany St, Brooklyn, CT 06234

    • 4 Beds
    • 2.5 Baths
    • 1,520 Sq Ft
    • Built 1920

    Last Sold Summary

    • $184/SF
    • 10 Days On Market

    Current Estimated Value $276,116

    Last Listing Agent Christine Johnson RE/MAX One

    10 Tiffany St, Brooklyn, CT 06234
  • 44 Woodland Dr, Windham, CT 06280

    $310,000 Sold Oct 08, 2025

    44 Woodland Dr, Windham, CT 06280

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft
    • Built 1956

    Last Sold Summary

    • 7% Above List Price
    • $203/SF
    • 104 Days On Market

    Current Estimated Value $302,949

    Last Listing Agent Kelley Vanacore Century 21 AllPoints Realty

    44 Woodland Dr, Windham, CT 06280

Showing Results 81 - 120, Page 3 of 18

Connecticut Windham County

Recently Sold Real Estate & Homes in Windham County, CT

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group