8,659

Madison, CT Homes

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  • 9 Old Farms Rd, Madison, CT 06443

    $551,000

    Sold Jan 20, 2026

    9 Old Farms Rd, Madison, CT 06443

    • 4 Beds
    • 1.5 Baths
    • 1,828 Sq Ft
    • Built 1973

    Last Sold Summary

    • 4% Below List Price
    • $301/SF
    • 82 Days On Market

    Current Estimated Value $558,700

    Last Listing Agent Luke Florian SSG Real Estate LLC

    9 Old Farms Rd, Madison, CT 06443
  • 38 Opening Hill Rd, Madison, CT 06443
    38 Opening Hill Rd, Madison, CT 06443
    38 Opening Hill Rd, Madison, CT 06443
    /11

    $1,500,000

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

    38 Opening Hill Rd, Madison, CT 06443

    2024 is the year to have the home of your dreams! Come see this gorgeous enclave of four to-be-built houses in an ideal location less than 10 minutes from the center of Madison, with restaurants, beaches, shops, and the historic Green all within 5 miles. Surrounded by natural wooded beauty and bordered by Madison Conservation Land, these lots are stunning! Includes all the details you would

    Karen Rosenthal William Raveis Real Estate

    38 Opening Hill Rd, Madison, CT 06443
  • 35 Bishop Ln, Madison, CT 06443

    $835,000

    Sold Sep 15, 2025

    35 Bishop Ln, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,568 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Above List Price
    • $325/SF
    • 19 Days On Market

    Current Estimated Value $859,012

    Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

    35 Bishop Ln, Madison, CT 06443
  • 6 Ladshaw Dr, Madison, CT 06443
    6 Ladshaw Dr, Madison, CT 06443
    6 Ladshaw Dr, Madison, CT 06443
    /27

    $499,000

    $41K PRICE DROP Under Contract
    • 2 Beds
    • 2 Baths
    • 1,360 Sq Ft

    6 Ladshaw Dr, Madison, CT 06443

    Privacy & convenience are both found within this updated detached stand-alone Ranch home in sought after Kensington Acres. Enjoy this 'tucked away' home yet a short walk to historic downtown Madison with its famed bookstore, shopping, restaurants & retail stores. This home has been beautifully maintained and shows pride of ownership throughout. Enjoy single floor living in your 2 bedroom, 2 bath

    Greg robbins Houlihan Lawrence WD

    6 Ladshaw Dr, Madison, CT 06443
  • 1543 Durham Rd, Madison, CT 06443

    $437,000

    Sold Feb 26, 2026

    1543 Durham Rd, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 3,711 Sq Ft
    • Built 1930

    Last Sold Summary

    • 3% Above List Price
    • $118/SF
    • 31 Days On Market

    Current Estimated Value $439,416

    Last Listing Agent Rob McConville RE/MAX Heritage

    1543 Durham Rd, Madison, CT 06443
  • 32 North St, Madison, CT 06443
    32 North St, Madison, CT 06443
    32 North St, Madison, CT 06443
    /20

    $164,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 592 Sq Ft

    32 North St, Madison, CT 06443

    32 North Street is calling you home! Set on one of the largest lots in Dud's Village, this lovely cottage is the idyllic seasonal abode. Equipped with 2 bedrooms, 1 full bath, and an outdoor shower, you will surely enjoy your summers along the Madison shoreline here. The recently refreshed kitchen and fresh coat of paint throughout will undoubtedly delight. And let's not forget the new floors in

    Melanie Abbott William Pitt Sotheby's Int'l

    32 North St, Madison, CT 06443
  • 5 Evarts Ln, Madison, CT 06443

    $1,200,000

    Sold Mar 13, 2026

    5 Evarts Ln, Madison, CT 06443

    • 2 Beds
    • 2.5 Baths
    • 2,418 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Above List Price
    • $496/SF
    • 33 Days On Market

    Current Estimated Value $1,152,662

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    5 Evarts Ln, Madison, CT 06443
  • 69 Squires Rd, Madison, CT 06443
    69 Squires Rd, Madison, CT 06443
    69 Squires Rd, Madison, CT 06443
    /40

    $699,000

    Pending
    • 3 Beds
    • 3 Baths
    • 2,025 Sq Ft

    69 Squires Rd, Madison, CT 06443

    Meticulously reimagined from top to bottom, this stunning contemporary home delivers 2,025 sq ft of turnkey luxury on over an acre of level land. Tucked on a peaceful street, the residence boasts 3 bedrooms and 3 full baths, highlighted by a main-level primary suite with its own fireplace, patio access, and spa-inspired bath. There is a versatile 2nd-floor suite with full bath: perfect for an

    Sue Woods William Pitt Sotheby's Int'l

    69 Squires Rd, Madison, CT 06443
  • 41 Sportsman Hill Rd, Madison, CT 06443

    $690,000

    Sold Aug 13, 2025

    41 Sportsman Hill Rd, Madison, CT 06443

    • 4 Beds
    • 3.5 Baths
    • 3,120 Sq Ft
    • Built 1966

    Last Sold Summary

    • 10% Above List Price
    • $221/SF
    • 33 Days On Market

    Current Estimated Value $697,582

    Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

    41 Sportsman Hill Rd, Madison, CT 06443
  • 99 Garnet Park Rd, Madison, CT 06443
    99 Garnet Park Rd, Madison, CT 06443
    99 Garnet Park Rd, Madison, CT 06443
    /40

    $1,899,900

    • 4 Beds
    • 2.5 Baths
    • 2,957 Sq Ft

    99 Garnet Park Rd, Madison, CT 06443

    Stunning waterfront home with water views on both sides, offering a rare coastal setting in an upscale neighborhood surrounded by multimillion-dollar properties. Enjoy breathtaking views from the rear of the home and expansive backyard, along with shared waterfront access across the street where a kayak or small boat may be launched at high tide. Designed with flexibility in mind, this home

    Heather Smith Our Home Realty Advisors

    99 Garnet Park Rd, Madison, CT 06443
  • 21 Apple Way, Madison, CT 06443

    $561,500

    Sold Mar 09, 2026

    21 Apple Way, Madison, CT 06443

    • 2 Beds
    • 2.5 Baths
    • 1,414 Sq Ft
    • Built 1994

    Last Sold Summary

    • 2% Above List Price
    • $397/SF
    • 2 Days On Market

    Current Estimated Value $559,141

    Last Listing Agent Rachel Welch William Raveis Real Estate

    21 Apple Way, Madison, CT 06443
  • 4 Aylesbury Cir, Madison, CT 06443
    4 Aylesbury Cir, Madison, CT 06443
    4 Aylesbury Cir, Madison, CT 06443
    /34

    $610,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,644 Sq Ft

    4 Aylesbury Cir, Madison, CT 06443

    Spectacular and elegant 2 bedroom free standing ranch with living room, kitchen, family room/office, dining room, 2 bedrooms, 2 baths and a garage. The kitchen is a show stopper with designer touches, high end appliances, white cabinets some with glass, granite counters, desk, a charming window seat and built ins. The dining room has a gas fireplace, built ins and is quite large for gatherings.

    Judy Libby Berkshire Hathaway NE Prop.

    4 Aylesbury Cir, Madison, CT 06443
  • 908 Boston Post Rd Unit 908, Madison, CT 06443

    $1,250,000

    Sold Apr 21, 2026

    908 Boston Post Rd Unit 908, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 2,368 Sq Ft
    • Built 2021

    Last Sold Summary

    • 7% Below List Price
    • $528/SF
    • 110 Days On Market

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    908 Boston Post Rd Unit 908, Madison, CT 06443
  • 32 Liberty St, Madison, CT 06443
    32 Liberty St, Madison, CT 06443
    32 Liberty St, Madison, CT 06443
    /29

    $1,299,000

    • 3 Beds
    • 3 Baths
    • 1,188 Sq Ft

    32 Liberty St, Madison, CT 06443

    Rare coastal compound opportunity in Madison's highly desirable Seaview Beach area. Situated on approximately one-half acre just moments from the shoreline, this unique property features a main residence and a newer detached accessory dwelling unit, offering flexibility rarely found in one of Connecticut's premier shoreline communities. The main home is clean, functional, and ready for a new

    Karina Ukhnitska Real Broker CT, LLC

    32 Liberty St, Madison, CT 06443
  • 36 Manzoni Farm Dr, Madison, CT 06443

    $1,400,000

    Sold Jul 07, 2025

    36 Manzoni Farm Dr, Madison, CT 06443

    • 4 Beds
    • 3.5 Baths
    • 4,936 Sq Ft
    • Built 2001

    Last Sold Summary

    • 8% Above List Price
    • $284/SF
    • 47 Days On Market

    Current Estimated Value $1,460,572

    Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

    36 Manzoni Farm Dr, Madison, CT 06443
  • 64 Webster Point Rd, Madison, CT 06443
    64 Webster Point Rd, Madison, CT 06443
    64 Webster Point Rd, Madison, CT 06443
    /37

    $2,195,000

    $154K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 4,010 Sq Ft

    64 Webster Point Rd, Madison, CT 06443

    NEW PRICE BELOW RECENT APPRAISAL. One house from L.I. Sound on a quiet Webster Point Road cul-de-sac, this 4000+ sf house delivers the ideal shoreline life: deeded beach access, multi-level panoramic water views, walkable distance to the Hammonasset Trail, and a spacious interior perfect for both large gatherings & cozy family life. A double-height foyer opens the house and leads into

    Margaret Muir William Pitt Sotheby's Int'l

    64 Webster Point Rd, Madison, CT 06443
  • 29 Circle Beach Rd, Madison, CT 06443

    $693,000

    Sold Jan 30, 2026

    29 Circle Beach Rd, Madison, CT 06443

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1935

    Last Sold Summary

    • 1% Below List Price
    • $962/SF
    • 5 Days On Market

    Current Estimated Value $693,945

    Last Listing Agent Gary Piccirillo RE/MAX Right Choice

    29 Circle Beach Rd, Madison, CT 06443
  • 53 Summer Hill Rd, Madison, CT 06443
    53 Summer Hill Rd, Madison, CT 06443
    53 Summer Hill Rd, Madison, CT 06443
    /29

    $799,000

    Open Sat 12PM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 2,024 Sq Ft

    53 Summer Hill Rd, Madison, CT 06443

    Wake up to pure tranquility in this stunning 4-bedroom, 2.5-bath contemporary home. Perfectly positioned across from the Hammonasset River, the setting is nothing short of amazing-complete with mature trees, bird song, and beautiful multi-tiered stone landscaping. Boasting modern lines and an incredible connection to its natural surroundings, this home offers a private retreat like no other.

    Pam Kadamus William Pitt Sotheby's Int'l

    53 Summer Hill Rd, Madison, CT 06443
  • 00 Stone Rd, Madison, CT 06443

    $692,000

    Sold Aug 08, 2025

    00 Stone Rd, Madison, CT 06443

    • Land
    • 1 Acre
    • $692,000 per Acre

    Last Sold Summary

    • 8% Below List Price
    • 156 Days On Market

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

    00 Stone Rd, Madison, CT 06443
  • 0 Bushnell Ln, Madison, CT 06443
    0 Bushnell Ln, Madison, CT 06443
    0 Bushnell Ln, Madison, CT 06443
    /6

    $1,250,000

    New Construction Pending
    • 2 Beds
    • 3.5 Baths
    • 2,000 Sq Ft

    0 Bushnell Ln, Madison, CT 06443

    Location, location, location! Build your home in the shoreline town of Madison! This proposed 2000sf modern farmhouse style home has a first floor primary bedroom, 3 full baths with additional space for an office, a rec room and an open floor plan. Vaulted ceilings, lots of natural light and energy efficiency make this build stand out. The proposed design can be modified to meet your needs.

    Justin Bradley Coldwell Banker Realty

    0 Bushnell Ln, Madison, CT 06443
  • 48 Shepherds Trail, Madison, CT 06443

    $775,000

    Sold Jan 16, 2026

    48 Shepherds Trail, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 4,879 Sq Ft
    • Built 1991

    Last Sold Summary

    • 9% Below List Price
    • $159/SF
    • 170 Days On Market

    Current Estimated Value $828,349

    Last Listing Agent Erin Connelly Coldwell Banker Realty

    48 Shepherds Trail, Madison, CT 06443
  • 55 Island Ave, Madison, CT 06443
    55 Island Ave, Madison, CT 06443
    55 Island Ave, Madison, CT 06443
    /34

    $1,400,000

    Pending
    • 4 Beds
    • 3 Baths
    • 3,046 Sq Ft

    55 Island Ave, Madison, CT 06443

    A rare offering in one of Madison's coveted shoreline neighborhoods, this custom-built Cape has been impeccably preserved since 1972, presenting a remarkable opportunity to own a home of enduring quality, character, and potential. Set on a private 1.02 acre lot with an Island address and easy access off Cambridge, the location offers exceptional privacy while remaining a quick walk to town, the

    Phoebe Schreiner William Pitt Sotheby's Int'l

    55 Island Ave, Madison, CT 06443
  • 16 Brantwood Dr, Madison, CT 06443

    $325,000

    Sold Aug 29, 2025

    16 Brantwood Dr, Madison, CT 06443

    • 2 Beds
    • 3 Baths
    • 1,332 Sq Ft
    • Built 1986

    Last Sold Summary

    • 13% Below List Price
    • $244/SF
    • 210 Days On Market

    Current Estimated Value $338,703

    Last Listing Agent Bette Zollshan William Pitt Sotheby's Int'l

    16 Brantwood Dr, Madison, CT 06443
  • 61 Hartford Ave, Madison, CT 06443
    61 Hartford Ave, Madison, CT 06443
    61 Hartford Ave, Madison, CT 06443
    /40

    $2,295,000

    $200K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,306 Sq Ft

    61 Hartford Ave, Madison, CT 06443

    Own an architectural masterpiece with waterviews! Rarely is a Robert Page (AIA) designed coastal home available and this is one of his most compelling. A collaboration with master builders Baldwin and Baldwin and executed with precision, this 3300 sf home with three exterior decks, (including a "Skydeck"), unfolds over four levels. Finished in 2010, this 3(+) bedroom, 3.1 bath gem offers 3300

    Margaret Muir William Pitt Sotheby's Int'l

    61 Hartford Ave, Madison, CT 06443
  • 52 Copse Rd, Madison, CT 06443

    $799,000

    Sold Nov 25, 2025

    52 Copse Rd, Madison, CT 06443

    • 3 Beds
    • 1 Bath
    • 1,382 Sq Ft
    • Built 1850

    Last Sold Summary

    • $578/SF
    • 11 Days On Market

    Current Estimated Value $803,186

    Last Listing Agent Laureen Kennedy Coldwell Banker Realty

    52 Copse Rd, Madison, CT 06443
  • 37 Lantern Hill Rd, Madison, CT 06443
    37 Lantern Hill Rd, Madison, CT 06443
    37 Lantern Hill Rd, Madison, CT 06443
    /38

    $2,875,000

    Pending
    • 5 Beds
    • 5.5 Baths
    • 7,139 Sq Ft

    37 Lantern Hill Rd, Madison, CT 06443

    An unbeatable location, 37 Lantern Hill is set in one of Madison's most desirable in-town neighborhoods. Close to sandy beaches, charming town center and the Madison Country Club, recreation and everyday conveniences are right at your doorstep. Traditional by design with ten foot ceilings, abundant natural light and generously scaled rooms that create an airy feel, ideal for relaxing or

    Margaret Muir William Pitt Sotheby's Int'l

    37 Lantern Hill Rd, Madison, CT 06443
  • 30 Church Ln, Madison, CT 06443

    $700,000

    Sold May 01, 2026

    30 Church Ln, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,908 Sq Ft
    • Built 1972

    Last Sold Summary

    • 17% Above List Price
    • $241/SF
    • 28 Days On Market

    Current Estimated Value $640,390

    Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

    30 Church Ln, Madison, CT 06443

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