8,537

Madison, CT Homes

Section Image
  • 24 Railroad Ave, Madison, CT 06443

    $465,000

    Sold Mar 05, 2026

    24 Railroad Ave, Madison, CT 06443

    • 2 Beds
    • 1.5 Baths
    • 1,000 Sq Ft
    • Built 1940

    Last Sold Summary

    • 2% Below List Price
    • $465/SF
    • 75 Days On Market

    Current Estimated Value $480,368

    Last Listing Agent Remi Tremblay William Raveis Real Estate

    24 Railroad Ave, Madison, CT 06443
    • 48 Lenore Dr, Madison, CT 06443

      Est $1,142,589

      Not Listed For Sale

      48 Lenore Dr, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 5,125 Sq Ft
      • Built 2004
      48 Lenore Dr, Madison, CT 06443

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Toni Iandoli William Pitt Sotheby's Int'l

  • 17 Barberry Ln, Madison, CT 06443
    17 Barberry Ln, Madison, CT 06443
    17 Barberry Ln, Madison, CT 06443
    /38

    $2,700,000

    Open Sat 1PM - 3PM $300K PRICE DROP
    • 4 Beds
    • 6 Baths
    • 4,833 Sq Ft

    17 Barberry Ln, Madison, CT 06443

    RARE OPPORTUNITY in the highly sought-after Barberry Farms Association! With only 2 MLS sales since 2021, homes in this premier beach community seldom become available. Enjoy private access to a wonderfully wide & deep sandy beach that has storage bins & an area for kayaks & small sailboats to make life easier. BIG home, BIG rooms. Spanning 4,833 sq ft, this 10 room Colonial features hardwood

    Todd Gould William Pitt Sotheby's Int'l

    17 Barberry Ln, Madison, CT 06443
  • 41 Allison Dr, Madison, CT 06443

    $1,225,000

    Sold Feb 18, 2026

    41 Allison Dr, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 3,609 Sq Ft
    • Built 2003

    Last Sold Summary

    • 5% Below List Price
    • $339/SF
    • 66 Days On Market

    Current Estimated Value $1,264,440

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

    41 Allison Dr, Madison, CT 06443
    • 1201 Durham Rd, Madison, CT 06443

      Est $582,582

      Not Listed For Sale

      1201 Durham Rd, Madison, CT 06443

      • 3 Beds
      • 1.5 Baths
      • 1,649 Sq Ft
      • Built 1976
      1201 Durham Rd, Madison, CT 06443

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Mike 'Mr. Z' Zerbini IMT Realty

  • 77 Hickory Ln, Madison, CT 06443
    77 Hickory Ln, Madison, CT 06443
    77 Hickory Ln, Madison, CT 06443
    /36

    $1,250,000

    Under Contract
    • 4 Beds
    • 4.5 Baths
    • 4,421 Sq Ft

    77 Hickory Ln, Madison, CT 06443

    CUSTOM MADISON ESTATE: Private 2.11-Acre Oasis with Heated Inground Pool. Custom-built in 2001 for the original owners, this exceptional Madison estate offers over 5,400SF of meticulously designed living space set on a private 2.11-acre lot. Designed for both refined daily living and high-end entertaining, the home boasts 4 bedrooms, 4.5 bathrooms, and an ideal layout for modern flexibility. At

    Kirsten Adams William Pitt Sotheby's Int'l

    77 Hickory Ln, Madison, CT 06443
  • 10 Isabell Dr, Madison, CT 06443

    $915,000

    Sold Sep 15, 2026

    10 Isabell Dr, Madison, CT 06443

    • 3 Beds
    • 3.5 Baths
    • 3,536 Sq Ft
    • Built 2001

    Last Sold Summary

    • 8% Below List Price
    • $259/SF
    • 88 Days On Market

    Current Estimated Value $956,342

    Last Listing Agent Claudia O'Connell William Raveis Real Estate

    10 Isabell Dr, Madison, CT 06443
    • 1197 Durham Rd, Madison, CT 06443

      Est $633,806

      Not Listed For Sale

      1197 Durham Rd, Madison, CT 06443

      • 3 Beds
      • 2 Baths
      • 1,494 Sq Ft
      • Built 1976
      1197 Durham Rd, Madison, CT 06443

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Debra Pardales William Pitt Sotheby's Int'l

  • 3 Arrowhead Rd, Madison, CT 06443
    3 Arrowhead Rd, Madison, CT 06443
    3 Arrowhead Rd, Madison, CT 06443
    /40

    $875,000

    $50K PRICE INCREASE Pending
    • 3 Beds
    • 4 Baths
    • 2,160 Sq Ft

    3 Arrowhead Rd, Madison, CT 06443

    Embrace the enchantment of Shoreline Living at its finest with this sun-drenched haven at 3 Arrowhead, a jewel nestled in a quaint community with the river at your doorstep. As you step into this radiant abode, you're welcomed by a symphony of natural light and the serene melodies of local birdsong. The home's design harmoniously blends the outdoors with the indoors, creating a tranquil retreat.

    Diana Hartman William Pitt Sotheby's Int'l

    3 Arrowhead Rd, Madison, CT 06443
  • 268 Durham Rd, Madison, CT 06443

    $265,000

    Sold Feb 19, 2026

    268 Durham Rd, Madison, CT 06443

    • Land
    • 2.29 Acres
    • $115,721 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 24 Days On Market

    Current Estimated Value $273,994

    Last Listing Agent Kirsten Adams William Pitt Sotheby's Int'l

    268 Durham Rd, Madison, CT 06443
    • 50 Copperfield Dr, Madison, CT 06443

      Est $1,437,885

      Not Listed For Sale

      50 Copperfield Dr, Madison, CT 06443

      • 5 Beds
      • 3.5 Baths
      • 4,374 Sq Ft
      • Built 1988
      50 Copperfield Dr, Madison, CT 06443

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Pam Kadamus William Pitt Sotheby's Int'l

  • 22 Pine Ridge Dr, Madison, CT 06443
    22 Pine Ridge Dr, Madison, CT 06443
    22 Pine Ridge Dr, Madison, CT 06443
    /7

    $350,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,004 Sq Ft

    22 Pine Ridge Dr, Madison, CT 06443

    Super opportunity to buy a home in Madison at a reasonable price! Needs work but well worth the effort. Owner suspects mold may be present in the basement but has received quotes for remediation and contents have been removed. The attached release and indemnification form must be signed prior to access being granted. This is a very rare and special property just waiting for you to make your own!

    Rick Allen William Raveis Real Estate

    22 Pine Ridge Dr, Madison, CT 06443
  • 198 Green Hill Rd, Madison, CT 06443

    $885,000

    Sold Mar 19, 2026

    198 Green Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,663 Sq Ft
    • Built 2013

    Last Sold Summary

    • 1% Above List Price
    • $332/SF
    • 19 Days On Market

    Current Estimated Value $904,777

    Last Listing Agent Kayla Chasse Compass Connecticut, LLC

    198 Green Hill Rd, Madison, CT 06443
    • 59 Copperfield Dr, Madison, CT 06443

      Est $1,286,306

      Not Listed For Sale

      59 Copperfield Dr, Madison, CT 06443

      • 4 Beds
      • 3.5 Baths
      • 4,442 Sq Ft
      • Built 1992
      59 Copperfield Dr, Madison, CT 06443

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Cathy Lynch Coldwell Banker Realty

  • 441 Opening Hill Rd, Madison, CT 06443
    441 Opening Hill Rd, Madison, CT 06443
    441 Opening Hill Rd, Madison, CT 06443
    /33

    $1,975,000

    • 4 Beds
    • 2 Baths
    • 3,882 Sq Ft

    441 Opening Hill Rd, Madison, CT 06443

    Updated 4 bedroom 2 Full bath Cape on 15+ Acres of rolling Meadows and woods bordering State Forest and over 800 feet of frontage on Opening Hill. Extensive updating includes new windows and doors, original wide-board refinishing in the original building. A new kitchen in the cathedral ceilinged family room addition with deck that commands beautiful views of two spring fed, stocked ponds below

    Steve Adkins Berkshire Hathaway NE Prop.

    441 Opening Hill Rd, Madison, CT 06443
  • 67 Boston Post Rd Unit 8, Madison, CT 06443

    $587,500

    Sold Mar 31, 2026

    67 Boston Post Rd Unit 8, Madison, CT 06443

    • 2 Beds
    • 2.5 Baths
    • 1,816 Sq Ft
    • Built 2018

    Last Sold Summary

    • 1% Below List Price
    • $324/SF
    • 56 Days On Market

    Current Estimated Value $584,989

    Last Listing Agent Dana Weinstein Coldwell Banker Realty

    67 Boston Post Rd Unit 8, Madison, CT 06443
    • 5 Michele Ln, Madison, CT 06443

      Est $1,186,049

      Not Listed For Sale

      5 Michele Ln, Madison, CT 06443

      • 4 Beds
      • 6 Baths
      • 5,220 Sq Ft
      • Built 1987
      5 Michele Ln, Madison, CT 06443

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Barbara Goetsch William Pitt Sotheby's Int'l

  • 38 Church Ln, Madison, CT 06443
    38 Church Ln, Madison, CT 06443
    38 Church Ln, Madison, CT 06443
    /40

    $699,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 2,750 Sq Ft

    38 Church Ln, Madison, CT 06443

    Welcome to 38 Church Lane, where exceptional custom renovations meet a captivating Madison setting. Perched high on a large corner lot surrounded by mature trees, this thoughtfully updated 4-bedroom, 2.5 bath home offers sophisticated finishes, a flexible floor plan ideal for multi-generational living and privacy just minutes from Madison's town center and shoreline. The stunning kitchen,

    Sue Woods William Pitt Sotheby's Int'l

    38 Church Ln, Madison, CT 06443
  • 13 Longview Terrace, Madison, CT 06443

    $779,000

    Sold Feb 03, 2026

    13 Longview Terrace, Madison, CT 06443

    • 3 Beds
    • 3.5 Baths
    • 3,772 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $207/SF
    • 69 Days On Market

    Current Estimated Value $813,675

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

    13 Longview Terrace, Madison, CT 06443
    • 739 Opening Hill Rd, Madison, CT 06443

      Est $460,299

      Not Listed For Sale

      739 Opening Hill Rd, Madison, CT 06443

      • 2 Beds
      • 3 Baths
      • 1,192 Sq Ft
      • Built 1930
      739 Opening Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 114 Days On Market

      Last Listing Agent Amanda Popplewell-Sanson Coldwell Banker Realty

  • 343 Horse Pond Rd, Madison, CT 06443
    343 Horse Pond Rd, Madison, CT 06443
    343 Horse Pond Rd, Madison, CT 06443
    /40

    $675,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 3 Baths
    • 2,138 Sq Ft

    343 Horse Pond Rd, Madison, CT 06443

    This sun-drenched and beautifully updated Cape offers a rare blend of charm, versatility, and an exceptional shoreline location. With two distinct living spaces, the property presents an outstanding opportunity for multigenerational living or a compelling investment property. The main residence features a stylishly renovated kitchen opening to a spacious dining area, two bedrooms-including an

    Melanie Scull William Pitt Sotheby's Int'l

    343 Horse Pond Rd, Madison, CT 06443
  • 22 Centre Village Dr, Madison, CT 06443

    $470,000

    Sold Oct 01, 2025

    22 Centre Village Dr, Madison, CT 06443

    • 1 Bed
    • 2.5 Baths
    • 1,569 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Below List Price
    • $300/SF
    • 126 Days On Market

    Current Estimated Value $475,762

    Last Listing Agent Emily Lovejoy William Raveis Real Estate

    22 Centre Village Dr, Madison, CT 06443
    • 730 Opening Hill Rd, Madison, CT 06443

      Est $614,113

      Not Listed For Sale

      730 Opening Hill Rd, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1966
      730 Opening Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent David Aurigemma Regency Real Estate, LLC

  • 262 Mungertown Rd, Madison, CT 06443
    262 Mungertown Rd, Madison, CT 06443
    262 Mungertown Rd, Madison, CT 06443
    /23

    $1,750,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,913 Sq Ft

    262 Mungertown Rd, Madison, CT 06443

    Build your custom dream home in South Madison! Welcome to this incredible opportunity in a prime location! Set on a level, treed, 2.32-acre lot on the hidden, more secluded end of Mungertown Road, offering PRIVACY and GREAT CONVENIENCE. Just THREE MILES to town and beaches, ONE MILE to Hand and Polson schools, and .25 MILES to the state-of-the-art Neck River Elementary, opened in 2025. Enjoy

    Lisa Rollins Team Compass Connecticut, LLC

    262 Mungertown Rd, Madison, CT 06443
  • 81 Bartlett Dr, Madison, CT 06443

    $630,000

    Sold Dec 12, 2025

    81 Bartlett Dr, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,088 Sq Ft
    • Built 1971

    Last Sold Summary

    • 3% Below List Price
    • $302/SF
    • 119 Days On Market

    Current Estimated Value $659,757

    Last Listing Agent Lauren Freedman Coldwell Banker Realty

    81 Bartlett Dr, Madison, CT 06443
    • 53 Copperfield Dr, Madison, CT 06443

      Est $1,094,495

      Not Listed For Sale

      53 Copperfield Dr, Madison, CT 06443

      • 5 Beds
      • 2.5 Baths
      • 3,595 Sq Ft
      • Built 1990
      53 Copperfield Dr, Madison, CT 06443

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Nikki Travaglino William Pitt Sotheby's Int'l

  • 462 Horse Pond Rd, Madison, CT 06443
    462 Horse Pond Rd, Madison, CT 06443
    462 Horse Pond Rd, Madison, CT 06443
    /12

    $1,375,000

    New Construction Pending
    • 4 Beds
    • 3.5 Baths
    • 4,357 Sq Ft

    462 Horse Pond Rd, Madison, CT 06443

    2025 is the year to have the home of your dreams! Come see this gorgeous enclave of five to-be-built houses on a private road in the charming coastal town of Madison. Ideally located just two hours from both NYC and Boston, Madison is beloved for its award-winning schools, restaurants, shops, and of course, beautiful beaches! Constructed by a well-established local Madison builder, these houses

    Karen Rosenthal William Raveis Real Estate

    462 Horse Pond Rd, Madison, CT 06443
  • 531 Green Hill Rd, Madison, CT 06443

    $565,000

    Sold Sep 29, 2025

    531 Green Hill Rd, Madison, CT 06443

    • 3 Beds
    • 1.5 Baths
    • 1,905 Sq Ft
    • Built 1964

    Last Sold Summary

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

    Current Estimated Value $590,082

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

    531 Green Hill Rd, Madison, CT 06443
    • 114 Squires Rd, Madison, CT 06443

      Est $628,123

      Not Listed For Sale

      114 Squires Rd, Madison, CT 06443

      • 3 Beds
      • 3 Baths
      • 2,325 Sq Ft
      • Built 1972
      114 Squires Rd, Madison, CT 06443

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Joseph Cominsky Houlihan Lawrence WD

  • 29 Wilshire Rd Unit 29, Madison, CT 06443
    29 Wilshire Rd Unit 29, Madison, CT 06443
    29 Wilshire Rd Unit 29, Madison, CT 06443
    /24

    $565,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft

    29 Wilshire Rd Unit 29, Madison, CT 06443

    Experience true WIDE OPEN SPACES in highly sought-after Kensington Acres South! With condos, it is all about LOCATION. This desirable completely detached standalone Ranch is not attached along the corners like some other units. Flooded w/ bright natural light, the home boasts peaceful, expansive lawn views from your private enclosed Sun Room, a perfect spot for morning coffee. A flat, level &

    Todd Gould William Pitt Sotheby's Int'l

    29 Wilshire Rd Unit 29, Madison, CT 06443
  • 16 Forest Hills Dr, Madison, CT 06443

    $815,000

    Sold Mar 26, 2026

    16 Forest Hills Dr, Madison, CT 06443

    • 5 Beds
    • 3 Baths
    • 3,992 Sq Ft
    • Built 1965

    Last Sold Summary

    • 7% Below List Price
    • $204/SF
    • 160 Days On Market

    Current Estimated Value $901,357

    Last Listing Agent Rod Cross Coldwell Banker Realty

    16 Forest Hills Dr, Madison, CT 06443
    • 88 Hickory Ln, Madison, CT 06443

      Est $1,386,577

      Not Listed For Sale

      88 Hickory Ln, Madison, CT 06443

      • 4 Beds
      • 5 Baths
      • 5,780 Sq Ft
      • Built 2001
      88 Hickory Ln, Madison, CT 06443

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Nicole White William Raveis Real Estate

  • 26 Bassett Ln, Madison, CT 06443
    26 Bassett Ln, Madison, CT 06443
    26 Bassett Ln, Madison, CT 06443
    /40

    $1,950,000

    $300K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,160 Sq Ft

    26 Bassett Ln, Madison, CT 06443

    Completely rebuilt and expanded in 2026, this custom coastal home with deeded beach rights is located in Madison's charming Seafields Association. Thoughtfully designed with designer details throughout, the home provides elevated shoreline living with glimpses of Long Island Sound, state-of-the-art appliances, high-end finishes, a bright, open layout, mudroom, butler's pantry with laundry, and a

    Steven Koleno Beycome of Connecticut

    26 Bassett Ln, Madison, CT 06443
  • 21 Little Hollow Rd, Madison, CT 06443

    $725,000

    Sold Apr 09, 2026

    21 Little Hollow Rd, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 1,589 Sq Ft
    • Built 1977

    Last Sold Summary

    • 1% Above List Price
    • $456/SF
    • 14 Days On Market

    Current Estimated Value $722,994

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    21 Little Hollow Rd, Madison, CT 06443
    • 126 Hickory Ln, Madison, CT 06443

      Est $1,347,112

      Not Listed For Sale

      126 Hickory Ln, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 4,430 Sq Ft
      • Built 2002
      126 Hickory Ln, Madison, CT 06443

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Judy Libby Berkshire Hathaway NE Prop.

  • 885 Boston Post Rd, Madison, CT 06443
    885 Boston Post Rd, Madison, CT 06443
    885 Boston Post Rd, Madison, CT 06443
    /22

    $599,900

    $149K PRICE DROP
    • Land
    • 8,276 Sq Ft
    • $3,157,368 per Acre

    885 Boston Post Rd, Madison, CT 06443

    Fully approved and ready to go, this exceptional commercial lot is situated in the heart of vibrant downtown Madison. Boasting approvals for a 5,000 square foot building the property includes a brand-new septic system, 13 designated parking spaces with additional parking options, and unbeatable proximity to restaurants, shopping, the train station, and I-95. Imagine welcoming clients or customers

    Michael Hvizdo Coldwell Banker Realty

    885 Boston Post Rd, Madison, CT 06443
  • 19 Green Acres Dr, Madison, CT 06443

    $660,000

    Sold May 04, 2026

    19 Green Acres Dr, Madison, CT 06443

    • 4 Beds
    • 2 Baths
    • 1,903 Sq Ft
    • Built 1957

    Last Sold Summary

    • 7% Above List Price
    • $347/SF
    • 5 Days On Market

    Current Estimated Value $655,147

    Last Listing Agent Amy Kirst William Pitt Sotheby's Int'l

    19 Green Acres Dr, Madison, CT 06443
    • 119 Squires Rd, Madison, CT 06443

      Est $640,420

      Not Listed For Sale

      119 Squires Rd, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 1,624 Sq Ft
      • Built 1972
      119 Squires Rd, Madison, CT 06443

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent George Sznaj DB Associates of CT, LLC

  • 0 Skytop Dr, Madison, CT 06443
    0 Skytop Dr, Madison, CT 06443
    /2

    $159,900

    Under Contract
    • Land
    • 1.43 Acres
    • $111,818 per Acre

    0 Skytop Dr, Madison, CT 06443

    Great opportunity to build in an established neighborhood in the beautiful shoreline community of Madison, CT! Large 1.43 acre rear lot is extremely private and ready for your dream home. Located just a short 1.5mi / 5 minute drive to downtown with easy access to I-95 and a short drive to Hammonasset Beach. Per town will need an updated perc test for final approval. Agent/owner

    Luke Florian SSG Real Estate LLC

    0 Skytop Dr, Madison, CT 06443
  • 20C Yankee Glen Rd Unit 20C, Madison, CT 06443

    $343,000

    Sold Jan 16, 2026

    20C Yankee Glen Rd Unit 20C, Madison, CT 06443

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1979

    Last Sold Summary

    • 11% Below List Price
    • $307/SF
    • 95 Days On Market

    Current Estimated Value $445,374

    Last Listing Agent Dallas Davis Dalvis Realty

    20C Yankee Glen Rd Unit 20C, Madison, CT 06443

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