1,690

Chester, CT Homes

Section Image
    • 30 Middlesex Ave, Chester, CT 06412

      Est $411,208

      Not Listed For Sale

      30 Middlesex Ave, Chester, CT 06412

      • 2 Beds
      • 1.5 Baths
      • 1,362 Sq Ft
      • Built 1922
      30 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 17% Above List Price
      • $257/SF
      • 73 Days On Market
      • Last Sold Price $350,000
      • Oct 16, 2023

      Last Listing Agent Agota Perry-Hill William Raveis Real Estate

  • 25 Gilbert Hill Rd, Chester, CT 06412

    $1,135,000

    Sold Jun 30, 2025

    25 Gilbert Hill Rd, Chester, CT 06412

    • 4 Beds
    • 4.5 Baths
    • 3,351 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Above List Price
    • $339/SF
    • 16 Days On Market

    Current Estimated Value $1,163,934

    Last Listing Agent Robin Linares William Pitt Sotheby's Int'l

    25 Gilbert Hill Rd, Chester, CT 06412
    • 28 Goose Hill Rd, Chester, CT 06412

      Est $614,184

      Not Listed For Sale

      28 Goose Hill Rd, Chester, CT 06412

      • 3 Beds
      • 3 Baths
      • 2,398 Sq Ft
      • Built 1870
      28 Goose Hill Rd, Chester, CT 06412

      Last Sold Summary

      • 6% Above List Price
      • $243/SF
      • 5 Days On Market
      • Last Sold Price $582,000
      • Nov 21, 2024

      Last Listing Agent Cheryl Bergeron-Lucca LPT Realty - IConn Team

  • 6 Ridge Rd, Chester, CT 06412

    $345,000

    Sold Aug 20, 2025

    6 Ridge Rd, Chester, CT 06412

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Above List Price
    • $234/SF
    • 31 Days On Market

    Current Estimated Value $358,523

    Last Listing Agent Craig Milton Re/Max Valley Shore

    6 Ridge Rd, Chester, CT 06412
    • 109 Main St, Chester, CT 06412

      Est $650,802

      Not Listed For Sale

      109 Main St, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 1,532 Sq Ft
      • Built 1868
      109 Main St, Chester, CT 06412

      Last Sold Summary

      • $424/SF
      • 3 Days On Market
      • Last Sold Price $650,000
      • Jun 01, 2023

      Last Listing Agent Julie Ovian William Pitt

  • 16 Hickory Hill Dr, Chester, CT 06412

    $755,000

    Sold Nov 19, 2025

    16 Hickory Hill Dr, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $398/SF
    • 48 Days On Market

    Current Estimated Value $759,762

    Last Listing Agent Suzanne McConville William Raveis Real Estate

    16 Hickory Hill Dr, Chester, CT 06412
    • 39 Castle View Dr, Chester, CT 06412

      Est $505,567

      Not Listed For Sale

      39 Castle View Dr, Chester, CT 06412

      • 3 Beds
      • 3.5 Baths
      • 2,208 Sq Ft
      • Built 2013
      39 Castle View Dr, Chester, CT 06412

      Last Sold Summary

      • 20% Above List Price
      • $190/SF
      • 95 Days On Market
      • Last Sold Price $419,900
      • Jan 07, 2025

      Last Listing Agent Gene Pica RE/MAX

  • 96 Goose Hill Rd, Chester, CT 06412

    $370,000

    Sold Jul 09, 2025

    96 Goose Hill Rd, Chester, CT 06412

    • 1 Bed
    • 1 Bath
    • 642 Sq Ft
    • Built 2017

    Last Sold Summary

    • 12% Above List Price
    • $576/SF
    • 3 Days On Market

    Current Estimated Value $376,281

    Last Listing Agent Jason Archer PMI Southeast CT

    96 Goose Hill Rd, Chester, CT 06412
    • 8 School Ln, Chester, CT 06412

      Est $524,755

      Not Listed For Sale

      8 School Ln, Chester, CT 06412

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 1986
      8 School Ln, Chester, CT 06412

      Last Sold Summary

      • 17% Above List Price
      • $297/SF
      • 2 Days On Market
      • Last Sold Price $449,000
      • Jul 14, 2023

      Last Listing Agent Ian Sacks Coldwell Banker Realty

  • 4 Sypher Rd, Chester, CT 06412

    $525,000

    Sold Jul 25, 2025

    4 Sypher Rd, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,272 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Above List Price
    • $231/SF
    • 29 Days On Market

    Current Estimated Value $559,195

    Last Listing Agent Kelly Puorro Puorro Realty Group

    4 Sypher Rd, Chester, CT 06412
    • 16 Waterhouse Ln, Chester, CT 06412

      Est $1,316,152

      Not Listed For Sale

      16 Waterhouse Ln, Chester, CT 06412

      • 4 Beds
      • 4.5 Baths
      • 4,661 Sq Ft
      • Built 1988
      16 Waterhouse Ln, Chester, CT 06412

      Last Sold Summary

      • 5% Above List Price
      • $268/SF
      • 24 Days On Market
      • Last Sold Price $1,250,000
      • May 02, 2025

      Last Listing Agent Teri Lewis William Pitt

  • 137 Main St, Chester, CT 06412

    $610,000

    Sold Aug 01, 2025

    137 Main St, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,570 Sq Ft
    • Built 1915

    Last Sold Summary

    • 2% Above List Price
    • $389/SF
    • 15 Days On Market

    Current Estimated Value $612,577

    Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l

    137 Main St, Chester, CT 06412
    • 103 Goose Hill Rd, Chester, CT 06412

      Est $410,331

      Not Listed For Sale

      103 Goose Hill Rd, Chester, CT 06412

      • 3 Beds
      • 1.5 Baths
      • 1,560 Sq Ft
      • Built 1925
      103 Goose Hill Rd, Chester, CT 06412

      Last Sold Summary

      • 3% Above List Price
      • $256/SF
      • 12 Days On Market
      • Last Sold Price $400,000
      • Sep 25, 2024

      Last Listing Agent Amy Graham William Pitt

    • 165 W Main St, Chester, CT 06412

      Est $493,188

      Not Listed For Sale

      165 W Main St, Chester, CT 06412

      • 2 Beds
      • 1 Bath
      • 2,400 Sq Ft
      • Built 1928
      165 W Main St, Chester, CT 06412

      Last Sold Summary

      • 45% Above List Price
      • $142/SF
      • 9 Days On Market
      • Last Sold Price $340,000
      • Mar 20, 2024

      Last Listing Agent Michelle Hodge Innovative Properties

    • 181 Middlesex Ave, Chester, CT 06412

      Est $302,264

      Not Listed For Sale

      181 Middlesex Ave, Chester, CT 06412

      • 3 Beds
      • 1 Bath
      • 1,232 Sq Ft
      • Built 1956
      181 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 34% Above List Price
      • $183/SF
      • 19 Days On Market
      • Last Sold Price $225,000
      • Oct 31, 2023

      Last Listing Agent Sam Robinson William Raveis Real Estate

    • 33 E Liberty St, Chester, CT 06412

      Est $808,172

      Not Listed For Sale

      33 E Liberty St, Chester, CT 06412

      • 3 Beds
      • 1 Bath
      • 21,433 Sq Ft
      • Built 1848
      33 E Liberty St, Chester, CT 06412

      Last Sold Summary

      • 35% Above List Price
      • $28/SF
      • 70 Days On Market
      • Last Sold Price $600,000
      • Dec 01, 2023

      Last Listing Agent Lori Montazella William Pitt

    • 108 Middlesex Ave, Chester, CT 06412

      Est $725,173

      Not Listed For Sale

      108 Middlesex Ave, Chester, CT 06412

      • 4 Beds
      • 4.5 Baths
      • 4,056 Sq Ft
      • Built 2002
      108 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 7% Above List Price
      • $166/SF
      • 65 Days On Market
      • Last Sold Price $675,000
      • May 01, 2025

      Last Listing Agent Trever Smith Chiarito Real Estate LLC

    • 142 Main St, Chester, CT 06412

      Est $567,442

      Not Listed For Sale

      142 Main St, Chester, CT 06412

      • 3 Beds
      • 2 Baths
      • 2,188 Sq Ft
      • Built 1952
      142 Main St, Chester, CT 06412

      Last Sold Summary

      • 6% Above List Price
      • $245/SF
      • 58 Days On Market
      • Last Sold Price $537,000
      • Oct 11, 2024

      Last Listing Agent Theresa Bitondo Berkshire Hathaway Home Services

    • 132 Middlesex Ave, Chester, CT 06412

      Est $310,538

      Not Listed For Sale

      132 Middlesex Ave, Chester, CT 06412

      • 2 Beds
      • 1 Bath
      • 1,001 Sq Ft
      • Built 1927
      132 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 15% Above List Price
      • $270/SF
      • 12 Days On Market
      • Last Sold Price $270,000
      • Mar 22, 2024

      Last Listing Agent Nancy Mesham Coldwell Banker Realty

    • 14 Castle View Dr, Chester, CT 06412

      Est $339,456

      Not Listed For Sale

      14 Castle View Dr, Chester, CT 06412

      • 3 Beds
      • 1 Bath
      • 1,533 Sq Ft
      • Built 1962
      14 Castle View Dr, Chester, CT 06412

      Last Sold Summary

      • 21% Above List Price
      • $183/SF
      • 4 Days On Market
      • Last Sold Price $280,000
      • Dec 14, 2023

      Last Listing Agent Kelly Puorro Puorro Realty Group

    • 54 Straits Rd, Chester, CT 06412

      Est $522,850

      Not Listed For Sale

      54 Straits Rd, Chester, CT 06412

      • 4 Beds
      • 2.5 Baths
      • 2,160 Sq Ft
      • Built 1983
      54 Straits Rd, Chester, CT 06412

      Last Sold Summary

      • 34% Above List Price
      • $180/SF
      • 21 Days On Market
      • Last Sold Price $389,000
      • Jul 28, 2023

      Last Listing Agent Peg Mitchel Coldwell Banker Realty

    • 60 Goose Hill Rd, Chester, CT 06412

      Est $569,146

      Not Listed For Sale

      60 Goose Hill Rd, Chester, CT 06412

      • 3 Beds
      • 2 Baths
      • 2,402 Sq Ft
      • Built 1860
      60 Goose Hill Rd, Chester, CT 06412

      Last Sold Summary

      • 200% Above List Price
      • $79/SF
      • 19 Days On Market
      • Last Sold Price $190,000
      • Dec 28, 2023

      Last Listing Agent Courtney Ciscato RE/MAX

    • 11 Laurel St, Chester, CT 06412

      Est $215,644

      Not Listed For Sale

      11 Laurel St, Chester, CT 06412

      • 2 Beds
      • 1 Bath
      • 616 Sq Ft
      • Built 1946
      11 Laurel St, Chester, CT 06412

      Last Sold Summary

      • 14% Above List Price
      • $308/SF
      • 48 Days On Market
      • Last Sold Price $189,900
      • Nov 08, 2024

      Last Listing Agent Craig Milton RE/MAX

    • 3 Meadow Ln, Chester, CT 06412

      Est $322,438

      Not Listed For Sale

      3 Meadow Ln, Chester, CT 06412

      • 2 Beds
      • 1 Bath
      • 1,032 Sq Ft
      • Built 1956
      3 Meadow Ln, Chester, CT 06412

      Last Sold Summary

      • 12% Above List Price
      • $280/SF
      • 4 Days On Market
      • Last Sold Price $289,000
      • Jun 29, 2023

      Last Listing Agent Cheryl Cook RE/MAX

    • 5 Marina View Dr, Chester, CT 06412

      Est $553,627

      Not Listed For Sale

      5 Marina View Dr, Chester, CT 06412

      • 3 Beds
      • 3.5 Baths
      • 2,037 Sq Ft
      • Built 1993
      5 Marina View Dr, Chester, CT 06412

      Last Sold Summary

      • 11% Above List Price
      • $245/SF
      • 81 Days On Market
      • Last Sold Price $500,000
      • Jan 17, 2025

      Last Listing Agent Susan Malan William Pitt

    • 96 Middlesex Ave, Chester, CT 06412

      Est $1,236,996

      Not Listed For Sale

      96 Middlesex Ave, Chester, CT 06412

      • 4 Beds
      • 3.5 Baths
      • 3,153 Sq Ft
      • Built 1830
      96 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 5% Below List Price
      • $412/SF
      • 162 Days On Market
      • Last Sold Price $1,300,000
      • Jan 31, 2025

      Last Listing Agent Susan Malan William Pitt

    • 11 Bishop Rd, Chester, CT 06412

      Est $366,389

      Not Listed For Sale

      11 Bishop Rd, Chester, CT 06412

      • 3 Beds
      • 1.5 Baths
      • 1,188 Sq Ft
      • Built 1964
      11 Bishop Rd, Chester, CT 06412

      Last Sold Summary

      • 5% Above List Price
      • $295/SF
      • 6 Days On Market
      • Last Sold Price $350,000
      • Apr 07, 2025

      Last Listing Agent Craig Milton RE/MAX

    • 65 Bokum Rd, Chester, CT 06412

      Not Listed For Sale

      65 Bokum Rd, Chester, CT 06412

      • 4 Beds
      • 4 Baths
      • 3,926 Sq Ft
      • Built 1979
      65 Bokum Rd, Chester, CT 06412

      Last Sold Summary

      • $204/SF
      • 92 Days On Market
      • Last Sold Price $800,000
      • Aug 31, 2023

      Last Listing Agent Philip Warner William Pitt

    • 75 Cedar Lake Rd, Chester, CT 06412

      Est $1,182,233

      Not Listed For Sale

      75 Cedar Lake Rd, Chester, CT 06412

      • 4 Beds
      • 3.5 Baths
      • 3,690 Sq Ft
      • Built 2016
      75 Cedar Lake Rd, Chester, CT 06412

      Last Sold Summary

      • 3% Below List Price
      • $329/SF
      • 62 Days On Market
      • Last Sold Price $1,214,000
      • Jul 05, 2023

      Last Listing Agent Bill Heenan William Raveis Real Estate

    • 43 Liberty St, Chester, CT 06412

      Not Listed For Sale

      43 Liberty St, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 1,901 Sq Ft
      • Built 1826
      43 Liberty St, Chester, CT 06412

      Last Sold Summary

      • $631/SF
      • 109 Days On Market
      • Last Sold Price $1,200,000
      • Apr 23, 2024

      Last Listing Agent Sacha Armstrong William Pitt Sotheby's International Realty

    • 8 Bokum Rd, Chester, CT 06412

      Est $465,139

      Not Listed For Sale

      8 Bokum Rd, Chester, CT 06412

      • 3 Beds
      • 1.5 Baths
      • 1,738 Sq Ft
      • Built 1859
      8 Bokum Rd, Chester, CT 06412

      Last Sold Summary

      • 15% Above List Price
      • $233/SF
      • 7 Days On Market
      • Last Sold Price $405,000
      • Jul 31, 2024

      Last Listing Agent Kimberly McHugh Puorro Realty Group

    • 81 Spring St, Chester, CT 06412

      Est $419,727

      Not Listed For Sale

      81 Spring St, Chester, CT 06412

      • 5 Beds
      • 2 Baths
      • 2,064 Sq Ft
      • Built 1920
      81 Spring St, Chester, CT 06412

      Last Sold Summary

      • 14% Above List Price
      • $178/SF
      • 12 Days On Market
      • Last Sold Price $368,000
      • Dec 27, 2023

      Last Listing Agent Kimberly McHugh Puorro Realty Group

    • 15 Kirtland Terrace, Chester, CT 06412

      Est $242,520

      Not Listed For Sale

      15 Kirtland Terrace, Chester, CT 06412

      • 3 Beds
      • 1.5 Baths
      • 1,170 Sq Ft
      • Built 1951
      15 Kirtland Terrace, Chester, CT 06412

      Last Sold Summary

      • 13% Below List Price
      • $239/SF
      • 3 Days On Market
      • Last Sold Price $280,000
      • Mar 07, 2025

      Last Listing Agent Kristina Quinones William Pitt

    • 21 Castle View Dr, Chester, CT 06412

      Est $350,683

      Not Listed For Sale

      21 Castle View Dr, Chester, CT 06412

      • 3 Beds
      • 1 Bath
      • 1,274 Sq Ft
      • Built 1966
      21 Castle View Dr, Chester, CT 06412

      Last Sold Summary

      • 6% Above List Price
      • $259/SF
      • 52 Days On Market
      • Last Sold Price $330,000
      • Jan 12, 2024

      Last Listing Agent Kimberly Blackman William Pitt

    • 3 Johnson Rd, Chester, CT 06412

      Est $361,173

      Not Listed For Sale

      3 Johnson Rd, Chester, CT 06412

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1925
      3 Johnson Rd, Chester, CT 06412

      Last Sold Summary

      • 64% Above List Price
      • $176/SF
      • 88 Days On Market
      • Last Sold Price $220,000
      • Dec 22, 2023

      Last Listing Agent George Sznaj DB Associates of CT, LLC

    • 40 Gilbert Hill Rd, Chester, CT 06412

      Est $538,760

      Not Listed For Sale

      40 Gilbert Hill Rd, Chester, CT 06412

      • 2 Beds
      • 3 Baths
      • 1,395 Sq Ft
      • Built 1998
      40 Gilbert Hill Rd, Chester, CT 06412

      Last Sold Summary

      • 4% Below List Price
      • $403/SF
      • 6 Days On Market
      • Last Sold Price $562,000
      • Jul 31, 2024

      Last Listing Agent Cara Bernard Coldwell Banker Realty

    • 26 Middlesex Ave, Chester, CT 06412

      Est $448,209

      Not Listed For Sale

      26 Middlesex Ave, Chester, CT 06412

      • 4 Beds
      • 1.5 Baths
      • 1,496 Sq Ft
      • Built 1920
      26 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 12% Above List Price
      • $267/SF
      • 50 Days On Market
      • Last Sold Price $399,900
      • Jun 30, 2023

      Last Listing Agent Craig Milton RE/MAX

    • 9 Gilbert Hill Rd, Chester, CT 06412

      Est $404,550

      Not Listed For Sale

      9 Gilbert Hill Rd, Chester, CT 06412

      • 2 Beds
      • 1.5 Baths
      • 2,008 Sq Ft
      • Built 1971
      9 Gilbert Hill Rd, Chester, CT 06412

      Last Sold Summary

      • 1% Above List Price
      • $199/SF
      • 60 Days On Market
      • Last Sold Price $400,000
      • Oct 09, 2024

      Last Listing Agent Shane Bonanno William Raveis Real Estate

    • 6 Old County Rd, Chester, CT 06412

      Est $1,018,921

      Not Listed For Sale

      6 Old County Rd, Chester, CT 06412

      • 4 Beds
      • 2.5 Baths
      • 2,680 Sq Ft
      • Built 2002
      6 Old County Rd, Chester, CT 06412

      Last Sold Summary

      • 5% Above List Price
      • $364/SF
      • 5 Days On Market
      • Last Sold Price $975,000
      • Apr 30, 2025

      Last Listing Agent Susan Malan William Pitt

    • 10 Old County Rd, Chester, CT 06412

      Est $857,808

      Not Listed For Sale

      10 Old County Rd, Chester, CT 06412

      • 4 Beds
      • 3.5 Baths
      • 2,755 Sq Ft
      • Built 1998
      10 Old County Rd, Chester, CT 06412

      Last Sold Summary

      • 5% Below List Price
      • $327/SF
      • 26 Days On Market
      • Last Sold Price $900,000
      • Mar 24, 2025

      Last Listing Agent Susan Malan William Pitt

Showing Results 81 - 120, Page 3 of 18

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