8,645

Madison, CT Homes

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  • 395 Boston Post Rd, Madison, CT 06443

    $1,400,000 Sold May 01, 2026

    395 Boston Post Rd, Madison, CT 06443

    • 4 Beds
    • 5 Baths
    • 3,779 Sq Ft
    • Built 1828

    Last Sold Summary

    • 3% Below List Price
    • $370/SF
    • 7 Days On Market

    Current Estimated Value $1,442,706

    Last Listing Agent Laurie Mazzeo William Pitt Sotheby's Int'l

    395 Boston Post Rd, Madison, CT 06443
    • 33 Deepwood Dr, Madison, CT 06443

      Est $500,437 Not Listed For Sale

      33 Deepwood Dr, Madison, CT 06443

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1962
      33 Deepwood Dr, Madison, CT 06443

      Last Sold Summary

      • 14% Above List Price
      • $293/SF
      • 6 Days On Market
      • Last Sold Price $439,900
      • May 18, 2023

      Last Listing Agent Joel Berntsen BHGRE Gaetano Marra Homes

  • 18 Riverside Terrace, Madison, CT 06443
    18 Riverside Terrace, Madison, CT 06443
    18 Riverside Terrace, Madison, CT 06443
    /40

    $699,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,532 Sq Ft

    18 Riverside Terrace, Madison, CT 06443

    Offering 3,532 sq ft of well-designed living space, this 4-bedroom, 3.5-bath home combines comfort, functionality, and room to grow. The upper level features beautiful hardwood floors and a well-appointed primary suite set privately apart, complete with cathedral ceilings, a walk-in closet, and a large en-suite bath with a soaking tub. There are three additional bedrooms on this level. The main

    Emily Lovejoy William Raveis Real Estate

    18 Riverside Terrace, Madison, CT 06443
  • 728 Durham Rd, Madison, CT 06443

    $170,000 Sold Mar 06, 2026

    728 Durham Rd, Madison, CT 06443

    • Land
    • 1.55 Acres
    • $109,677 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 256 Days On Market

    Current Estimated Value $176,667

    Last Listing Agent Gene Pica RE/MAX Alliance

    728 Durham Rd, Madison, CT 06443
    • 4 Thames Way, Madison, CT 06443

      Est $654,013 Not Listed For Sale

      4 Thames Way, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,472 Sq Ft
      • Built 1986
      4 Thames Way, Madison, CT 06443

      Last Sold Summary

      • 33% Above List Price
      • $199/SF
      • 12 Days On Market
      • Last Sold Price $493,000
      • Jun 12, 2023

      Last Listing Agent Carol Farmer William Raveis Real Estate

  • 51 Brantwood Dr, Madison, CT 06443

    $250,000 Sold May 30, 2025

    51 Brantwood Dr, Madison, CT 06443

    • 1 Bed
    • 1 Bath
    • 764 Sq Ft
    • Built 1986

    Last Sold Summary

    • $327/SF
    • 4 Days On Market

    Current Estimated Value $246,550

    Last Listing Agent Rob McConville RE/MAX Heritage

    51 Brantwood Dr, Madison, CT 06443
    • 158 Saint Francis Woods Rd, Madison, CT 06443

      Est $721,109 Not Listed For Sale

      158 Saint Francis Woods Rd, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 3,101 Sq Ft
      • Built 1980
      158 Saint Francis Woods Rd, Madison, CT 06443

      Last Sold Summary

      • 4% Above List Price
      • $224/SF
      • 47 Days On Market
      • Last Sold Price $695,000
      • Jan 21, 2025

      Last Listing Agent Jane Cardarelli William Raveis Real Estate

  • 45 Wilshire Rd Unit 45, Madison, CT 06443

    $511,920 Sold Apr 16, 2026

    45 Wilshire Rd Unit 45, Madison, CT 06443

    • 2 Beds
    • 2.5 Baths
    • 1,879 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Above List Price
    • $272/SF
    • 45 Days On Market

    Current Estimated Value $499,886

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    45 Wilshire Rd Unit 45, Madison, CT 06443
    • 141 Saint Francis Woods Rd, Madison, CT 06443

      Est $613,479 Not Listed For Sale

      141 Saint Francis Woods Rd, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 1,980 Sq Ft
      • Built 1977
      141 Saint Francis Woods Rd, Madison, CT 06443

      Last Sold Summary

      • 18% Above List Price
      • $262/SF
      • 93 Days On Market
      • Last Sold Price $519,000
      • Mar 04, 2024

      Last Listing Agent Emily Lovejoy William Raveis Real Estate

  • 86 Winterhill Rd, Madison, CT 06443

    $703,500 Sold Sep 30, 2025

    86 Winterhill Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,330 Sq Ft
    • Built 1979

    Last Sold Summary

    • 2% Above List Price
    • $302/SF
    • 50 Days On Market

    Current Estimated Value $716,653

    Last Listing Agent Kim Fetera Coldwell Banker Realty

    86 Winterhill Rd, Madison, CT 06443
    • 115 Saint Francis Woods Rd, Madison, CT 06443

      Est $701,854 Not Listed For Sale

      115 Saint Francis Woods Rd, Madison, CT 06443

      • 4 Beds
      • 2 Baths
      • 2,172 Sq Ft
      • Built 1973
      115 Saint Francis Woods Rd, Madison, CT 06443

      Last Sold Summary

      • 8% Above List Price
      • $299/SF
      • 73 Days On Market
      • Last Sold Price $650,000
      • Nov 21, 2023

      Last Listing Agent Kirsten Adams William Pitt

  • 144 Middle Beach Rd, Madison, CT 06443

    $3,100,000 Sold May 07, 2026

    144 Middle Beach Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 3,127 Sq Ft
    • Built 1910

    Last Sold Summary

    • $991/SF
    • 70 Days On Market

    Current Estimated Value $2,854,227

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

    144 Middle Beach Rd, Madison, CT 06443
    • 7 Williamsburg Cir, Madison, CT 06443

      Est $736,708 Not Listed For Sale

      7 Williamsburg Cir, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 3,180 Sq Ft
      • Built 1982
      7 Williamsburg Cir, Madison, CT 06443

      Last Sold Summary

      • 26% Above List Price
      • $184/SF
      • 4 Days On Market
      • Last Sold Price $585,000
      • Jul 24, 2023

      Last Listing Agent Lynne Hubbard Coldwell Banker Realty

  • 93 Race Hill Rd, Madison, CT 06443

    $595,000 Sold Jul 08, 2025

    93 Race Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,604 Sq Ft
    • Built 1987

    Last Sold Summary

    • $228/SF
    • 73 Days On Market

    Current Estimated Value $624,597

    Last Listing Agent Heather Dacey William Raveis Real Estate

    93 Race Hill Rd, Madison, CT 06443
    • 23 Williamsburg Cir, Madison, CT 06443

      Est $800,957 Not Listed For Sale

      23 Williamsburg Cir, Madison, CT 06443

      • 3 Beds
      • 2.5 Baths
      • 3,126 Sq Ft
      • Built 1979
      23 Williamsburg Cir, Madison, CT 06443

      Last Sold Summary

      • 3% Above List Price
      • $248/SF
      • 58 Days On Market
      • Last Sold Price $775,000
      • Nov 13, 2024

      Last Listing Agent Lynne Hubbard Coldwell Banker Realty

  • 173 Wildwood Ave, Madison, CT 06443

    $760,000 Sold Apr 13, 2026

    173 Wildwood Ave, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,118 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Above List Price
    • $359/SF
    • 69 Days On Market

    Current Estimated Value $714,268

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    173 Wildwood Ave, Madison, CT 06443
    • 24 Lyle Dr, Madison, CT 06443

      Est $725,751 Not Listed For Sale

      24 Lyle Dr, Madison, CT 06443

      • 3 Beds
      • 2.5 Baths
      • 1,938 Sq Ft
      • Built 1995
      24 Lyle Dr, Madison, CT 06443

      Last Sold Summary

      • 19% Above List Price
      • $315/SF
      • 14 Days On Market
      • Last Sold Price $610,000
      • Oct 27, 2023

      Last Listing Agent Marcy Noiseux Coldwell Banker Realty

  • 45 East St, Madison, CT 06443

    $210,000 Sold Jul 22, 2025

    45 East St, Madison, CT 06443

    • 2 Beds
    • 1 Bath
    • 604 Sq Ft
    • Built 1960

    Last Sold Summary

    • 7% Below List Price
    • $348/SF
    • 27 Days On Market

    Last Listing Agent Melanie Abbott William Pitt Sotheby's Int'l

    45 East St, Madison, CT 06443
    • 17 Lyle Dr, Madison, CT 06443

      Est $764,572 Not Listed For Sale

      17 Lyle Dr, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,862 Sq Ft
      • Built 1995
      17 Lyle Dr, Madison, CT 06443

      Last Sold Summary

      • 5% Above List Price
      • $255/SF
      • 53 Days On Market
      • Last Sold Price $731,000
      • Apr 09, 2025

      Last Listing Agent Emily Lovejoy William Raveis Real Estate

  • 60 Robin Ridge Dr, Madison, CT 06443

    $575,000 Sold Jan 09, 2026

    60 Robin Ridge Dr, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 1,992 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Below List Price
    • $289/SF
    • 73 Days On Market

    Current Estimated Value $588,732

    Last Listing Agent Phoebe Schreiner William Pitt Sotheby's Int'l

    60 Robin Ridge Dr, Madison, CT 06443
    • 524 Opening Hill Rd, Madison, CT 06443

      Est $703,323 Not Listed For Sale

      524 Opening Hill Rd, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,004 Sq Ft
      • Built 1994
      524 Opening Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 17% Above List Price
      • $299/SF
      • 41 Days On Market
      • Last Sold Price $600,000
      • Nov 30, 2023

      Last Listing Agent Phoebe Schreiner William Pitt

  • 71 Madison Springs Dr, Madison, CT 06443

    $975,000 Sold Dec 17, 2025

    71 Madison Springs Dr, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 3,333 Sq Ft
    • Built 1981

    Last Sold Summary

    • 8% Above List Price
    • $293/SF
    • 3 Days On Market

    Current Estimated Value $967,040

    Last Listing Agent Jules Gaughran - Etes William Pitt Sotheby's Int'l

    71 Madison Springs Dr, Madison, CT 06443
    • 579 Opening Hill Rd, Madison, CT 06443

      Est $737,392 Not Listed For Sale

      579 Opening Hill Rd, Madison, CT 06443

      • 5 Beds
      • 3.5 Baths
      • 2,380 Sq Ft
      • Built 1972
      579 Opening Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 8% Above List Price
      • $286/SF
      • 74 Days On Market
      • Last Sold Price $680,000
      • Mar 19, 2024

      Last Listing Agent Shane Khan William Raveis Real Estate

  • 9 Evarts Ln, Madison, CT 06443

    $1,050,000 Sold Jun 17, 2025

    9 Evarts Ln, Madison, CT 06443

    • 2 Beds
    • 2.5 Baths
    • 2,820 Sq Ft
    • Built 2004

    Last Sold Summary

    • 4% Below List Price
    • $372/SF
    • 27 Days On Market

    Current Estimated Value $1,185,692

    Last Listing Agent Jamie Lombardy William Pitt Sotheby's Int'l

    9 Evarts Ln, Madison, CT 06443
    • 22 Scenic Rd, Madison, CT 06443

      Est $627,731 Not Listed For Sale

      22 Scenic Rd, Madison, CT 06443

      • 4 Beds
      • 3 Baths
      • 2,628 Sq Ft
      • Built 1969
      22 Scenic Rd, Madison, CT 06443

      Last Sold Summary

      • 4% Above List Price
      • $229/SF
      • 22 Days On Market
      • Last Sold Price $601,000
      • Nov 18, 2024

      Last Listing Agent Susan Santoro William Pitt

  • 37 Sheffield Ln, Madison, CT 06443

    $761,000 Sold Aug 14, 2025

    37 Sheffield Ln, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,989 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Below List Price
    • $255/SF
    • 46 Days On Market

    Current Estimated Value $770,279

    Last Listing Agent Jane Cardarelli William Raveis Real Estate

    37 Sheffield Ln, Madison, CT 06443
    • 596 Opening Hill Rd, Madison, CT 06443

      Est $895,844 Not Listed For Sale

      596 Opening Hill Rd, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,678 Sq Ft
      • Built 1999
      596 Opening Hill Rd, Madison, CT 06443

      Last Sold Summary

      • $336/SF
      • 21 Days On Market
      • Last Sold Price $900,000
      • Jun 20, 2024

      Last Listing Agent Melanie Gunn Coldwell Banker Realty

  • 29 Flintlock Rd, Madison, CT 06443

    $711,000 Sold Aug 21, 2025

    29 Flintlock Rd, Madison, CT 06443

    • 4 Beds
    • 1.5 Baths
    • 2,458 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Above List Price
    • $289/SF
    • 40 Days On Market

    Current Estimated Value $718,852

    Last Listing Agent Betsy Anderson William Pitt Sotheby's Int'l

    29 Flintlock Rd, Madison, CT 06443
    • 101 Winding Rd, Madison, CT 06443

      Est $536,410 Not Listed For Sale

      101 Winding Rd, Madison, CT 06443

      • 4 Beds
      • 2 Baths
      • 1,848 Sq Ft
      • Built 1971
      101 Winding Rd, Madison, CT 06443

      Last Sold Summary

      • 22% Above List Price
      • $238/SF
      • 118 Days On Market
      • Last Sold Price $440,000
      • Nov 03, 2023

      Last Listing Agent Emily Lovejoy William Raveis Real Estate

  • 20 Robin Ridge Dr, Madison, CT 06443

    $456,500 Sold Aug 20, 2025

    20 Robin Ridge Dr, Madison, CT 06443

    • 3 Beds
    • 1.5 Baths
    • 1,468 Sq Ft
    • Built 1958

    Last Sold Summary

    • 2% Below List Price
    • $311/SF
    • 39 Days On Market

    Current Estimated Value $480,797

    Last Listing Agent Anne Marie Straka Compass Connecticut, LLC

    20 Robin Ridge Dr, Madison, CT 06443
    • 123 Deepwood Dr, Madison, CT 06443

      Est $447,648 Not Listed For Sale

      123 Deepwood Dr, Madison, CT 06443

      • 3 Beds
      • 1.5 Baths
      • 1,884 Sq Ft
      • Built 1964
      123 Deepwood Dr, Madison, CT 06443

      Last Sold Summary

      • 19% Above List Price
      • $199/SF
      • 63 Days On Market
      • Last Sold Price $375,000
      • Mar 15, 2024

      Last Listing Agent Nicholas Mastrangelo Coldwell Banker Realty

  • 97 Mungertown Rd, Madison, CT 06443

    $565,000 Sold Jul 15, 2025

    97 Mungertown Rd, Madison, CT 06443

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 1961

    Last Sold Summary

    • 3% Above List Price
    • $353/SF
    • 39 Days On Market

    Current Estimated Value $566,323

    Last Listing Agent Diandra Shafer mygoodagent

    97 Mungertown Rd, Madison, CT 06443
    • 105 Deepwood Dr, Madison, CT 06443

      Est $474,596 Not Listed For Sale

      105 Deepwood Dr, Madison, CT 06443

      • 3 Beds
      • 2 Baths
      • 1,832 Sq Ft
      • Built 1964
      105 Deepwood Dr, Madison, CT 06443

      Last Sold Summary

      • 3% Above List Price
      • $251/SF
      • 2 Days On Market
      • Last Sold Price $460,000
      • Jun 26, 2024

      Last Listing Agent Steven Elek RE/MAX Heritage

  • 26 Farm View Dr, Madison, CT 06443

    $630,000 Sold Feb 19, 2026

    26 Farm View Dr, Madison, CT 06443

    • 4 Beds
    • 2 Baths
    • 1,573 Sq Ft
    • Built 1981

    Last Sold Summary

    • 7% Above List Price
    • $401/SF
    • 5 Days On Market

    Current Estimated Value $602,605

    Last Listing Agent Elise Palacios eXp Realty

    26 Farm View Dr, Madison, CT 06443
    • 99 Deepwood Dr, Madison, CT 06443

      Est $487,323 Not Listed For Sale

      99 Deepwood Dr, Madison, CT 06443

      • 3 Beds
      • 1.5 Baths
      • 1,432 Sq Ft
      • Built 1965
      99 Deepwood Dr, Madison, CT 06443

      Last Sold Summary

      • 20% Above List Price
      • $283/SF
      • 72 Days On Market
      • Last Sold Price $405,000
      • May 10, 2023

      Last Listing Agent Lisa Daniele William Raveis Real Estate

  • 273 Legend Hill Rd, Madison, CT 06443

    $540,000 Sold Aug 28, 2025

    273 Legend Hill Rd, Madison, CT 06443

    • 2 Beds
    • 2 Baths
    • 1,598 Sq Ft
    • Built 1985

    Last Sold Summary

    • 1% Below List Price
    • $338/SF
    • 28 Days On Market

    Current Estimated Value $554,383

    Last Listing Agent Judy Libby Berkshire Hathaway NE Prop.

    273 Legend Hill Rd, Madison, CT 06443
    • 29 Milano Pond Dr, Madison, CT 06443

      Est $712,803 Not Listed For Sale

      29 Milano Pond Dr, Madison, CT 06443

      • 3 Beds
      • 2.5 Baths
      • 1,993 Sq Ft
      • Built 1990
      29 Milano Pond Dr, Madison, CT 06443

      Last Sold Summary

      • 74% Above List Price
      • $206/SF
      • 18 Days On Market
      • Last Sold Price $410,000
      • Mar 08, 2024

      Last Listing Agent Lori Miko Coldwell Banker Realty

  • 7 Madrina Ln, Madison, CT 06443

    $500,000 Sold Jan 26, 2026

    7 Madrina Ln, Madison, CT 06443

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1978

    Last Sold Summary

    • 5% Below List Price
    • $437/SF
    • 107 Days On Market

    Current Estimated Value $500,274

    Last Listing Agent Kayla Chasse Compass Connecticut, LLC

    7 Madrina Ln, Madison, CT 06443
    • 106 Bradley Corners Rd, Madison, CT 06443

      Est $589,495 Not Listed For Sale

      106 Bradley Corners Rd, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,080 Sq Ft
      • Built 1987
      106 Bradley Corners Rd, Madison, CT 06443

      Last Sold Summary

      • 16% Above List Price
      • $245/SF
      • 49 Days On Market
      • Last Sold Price $510,000
      • Dec 30, 2024

      Last Listing Agent Mary O'Neill Eagle Eye Realty PLLC

  • 286 Opening Hill Rd, Madison, CT 06443

    $610,000 Sold Mar 27, 2026

    286 Opening Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 1,870 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Above List Price
    • $326/SF
    • 50 Days On Market

    Current Estimated Value $595,355

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    286 Opening Hill Rd, Madison, CT 06443

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