8,659

Madison, CT Homes

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  • 15 Highland Terrace, Madison, CT 06443
    15 Highland Terrace, Madison, CT 06443
    15 Highland Terrace, Madison, CT 06443
    /40

    $2,195,000

    Open Sat 1PM - 4PM
    • 5 Beds
    • 3 Baths
    • 3,172 Sq Ft

    15 Highland Terrace, Madison, CT 06443

    COME SEE THIS ONE OF KIND FULLY RENOVATED MADISON HOME WITH PRIVATE BEACH RIGHTS!!! Just 300 feet from the sand, this home was once a traditional raised ranch and now has been brilliantly redesigned into a spacious 'elevated ranch' with an open-concept floor plan that feels airy, bright, and made for entertaining! Step into coastal luxury with this fully reimagined Madison home, where every

    John Cronin Century 21 AllPoints Realty

    15 Highland Terrace, Madison, CT 06443
  • 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
  • 45 Island Ave, Madison, CT 06443
    45 Island Ave, Madison, CT 06443
    45 Island Ave, Madison, CT 06443
    /38

    $3,750,000

    $250K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 5,657 Sq Ft

    45 Island Ave, Madison, CT 06443

    Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight

    Meig Walz Newcomb Coldwell Banker Realty

    45 Island Ave, 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 $171,166

    Last Listing Agent Gene Pica RE/MAX Alliance

    728 Durham Rd, Madison, CT 06443
  • 49 Hammonassett Meadows Rd, Madison, CT 06443
    49 Hammonassett Meadows Rd, Madison, CT 06443
    49 Hammonassett Meadows Rd, Madison, CT 06443
    /31

    $799,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,260 Sq Ft

    49 Hammonassett Meadows Rd, Madison, CT 06443

    LOCATION, LOCATION...This 4BR, 2.5 Bath home is in absolutely pristine condition. Meticulously maintained by the original owner, this home has been loved and cared for and it really shows! Located in the very desirable neighborhood, Hammonassett Meadows, and situated on a 1.45 acre lot. The home features upgraded Pella replacement windows, beautiful hardwood floors throughout, newer A/C spit

    Susan Clifford Coldwell Banker Realty

    49 Hammonassett Meadows Rd, Madison, CT 06443
  • 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 $512,022

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    45 Wilshire Rd Unit 45, Madison, CT 06443
  • 476 Summer Hill Rd, Madison, CT 06443
    476 Summer Hill Rd, Madison, CT 06443
    476 Summer Hill Rd, Madison, CT 06443
    /40

    $650,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,057 Sq Ft

    476 Summer Hill Rd, Madison, CT 06443

    This turnkey, sun-filled Colonial situated south of Route 80 in Madison perfectly blends meticulous maintenance with smart, modern updates. The gracious main level features elegant French doors opening to a bright living room, a generous formal dining room- a perfect place for family gatherings and a cozy family room centered around a classic wood-burning fireplace. The heart of the home is the

    Amy Kirst William Pitt Sotheby's Int'l

    476 Summer Hill Rd, Madison, CT 06443
  • 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 $710,617

    Last Listing Agent Kim Fetera Coldwell Banker Realty

    86 Winterhill Rd, Madison, CT 06443
    • 24 Lyle Dr, Madison, CT 06443

      Est $706,997

      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

      • 14 Days On Market

  • 23 Hampshire Rd Unit 23, Madison, CT 06443
    23 Hampshire Rd Unit 23, Madison, CT 06443
    23 Hampshire Rd Unit 23, Madison, CT 06443
    /39

    $545,000

    Under Contract
    • 2 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    23 Hampshire Rd Unit 23, Madison, CT 06443

    Welcome to Kensington North, a highly desirable condo community in the heart of Madison. This well-located unit offers a wonderful opportunity to create your ideal home in a sought-after setting. The main level features a spacious living and dining area, perfect for everyday living and entertaining. The eat-in kitchen offers great potential with sliders to the sunroom and patio as well as being

    Laurie Mazzeo William Pitt Sotheby's Int'l

    23 Hampshire Rd Unit 23, Madison, CT 06443
  • 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 $2,950,666

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

    144 Middle Beach Rd, Madison, CT 06443
    • 17 Lyle Dr, Madison, CT 06443

      Est $725,556

      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

      • 53 Days On Market

  • 42 Wildcat Rd, Madison, CT 06443
    42 Wildcat Rd, Madison, CT 06443
    42 Wildcat Rd, Madison, CT 06443
    /12

    $325,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,080 Sq Ft

    42 Wildcat Rd, Madison, CT 06443

    Ranch-style single-family home situated on 1 acre, just 5 minutes from Hammonasset State Beach. The property features classic New England stone walls surrounding much of the land, along with a detached two-car garage. Inside, has nice looking exposed beams! Then living room, kitchen, three bedrooms, and one bathroom-all on the main floor. Full unfinished basement with an exterior hatch. The

    Ethan Maddalena Berkshire Hathaway NE Prop.

    42 Wildcat Rd, Madison, CT 06443
  • 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 $621,791

    Last Listing Agent Heather Dacey William Raveis Real Estate

    93 Race Hill Rd, Madison, CT 06443
  • 89 Summer Hill Rd, Madison, CT 06443
    89 Summer Hill Rd, Madison, CT 06443
    89 Summer Hill Rd, Madison, CT 06443
    /39

    $789,000

    • 4 Beds
    • 2.5 Baths
    • 2,647 Sq Ft

    89 Summer Hill Rd, Madison, CT 06443

    Set on a beautiful, private 1.25-acre lot in one of Madison's sought-after neighborhoods, this spacious, well maintained Colonial offers exceptional flexibility and comfort with nine rooms plus an additional sunroom. The kitchen is updated with granite countertops and newer appliances. Bathrooms have all been updated with tile and granite. The floors are hardwood throughout the home. Thoughtfully

    Susan Wagner Berkshire Hathaway NE Prop.

    89 Summer Hill Rd, Madison, CT 06443
  • 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 $746,926

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    173 Wildwood Ave, Madison, CT 06443
  • 34 Canborne Way, Madison, CT 06443
    34 Canborne Way, Madison, CT 06443
    34 Canborne Way, Madison, CT 06443
    /30

    $485,900

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

    34 Canborne Way, Madison, CT 06443

    Nestled quietly at the rear of the Windemere Complex, this freestanding ranch-style unit delivers seamless, one-level living in a highly desirable location. Minutes from Hammonasset State Park, Madison's charming town center, and pristine town beaches, this home perfectly balances convenience and tranquility. Inside, newly installed flooring stretches across an inviting open floor plan. The

    Amy Kirst William Pitt Sotheby's Int'l

    34 Canborne Way, Madison, CT 06443
  • 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
    • 22 Scenic Rd, Madison, CT 06443

      Est $668,867

      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

      • 22 Days On Market

  • 880 Boston Post Rd, Madison, CT 06443
    880 Boston Post Rd, Madison, CT 06443
    880 Boston Post Rd, Madison, CT 06443
    /40

    $2,295,000

    $180K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,697 Sq Ft

    880 Boston Post Rd, Madison, CT 06443

    The historic c. 1904 Scranton Homestead, described as a Colonial Revival gem, has come to the market! This much admired 3700 sf in town landmark offers an estate feel on a large, beautifully landscaped lot providing both privacy and convenience, moments from the village center and East Wharf Beach. With four bedrooms, this residence borrows from classic forms, with window styles, columns and

    Margaret Muir William Pitt Sotheby's Int'l

    880 Boston Post Rd, Madison, CT 06443
  • 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 $578,667

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

    60 Robin Ridge Dr, Madison, CT 06443
  • 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
  • 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 $977,096

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

    71 Madison Springs Dr, Madison, CT 06443
  • 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 $763,341

    Last Listing Agent Jane Cardarelli William Raveis Real Estate

    37 Sheffield Ln, Madison, CT 06443
  • 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 $707,400

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

    29 Flintlock Rd, Madison, CT 06443
  • 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 $571,879

    Last Listing Agent Diandra Shafer mygoodagent

    97 Mungertown Rd, Madison, CT 06443
  • 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 $477,592

    Last Listing Agent Anne Marie Straka Compass Connecticut, LLC

    20 Robin Ridge Dr, Madison, CT 06443
    • 26 Jenda Way, Madison, CT 06443

      Est $722,239

      Not Listed For Sale

      26 Jenda Way, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,147 Sq Ft
      • Built 1987
      26 Jenda Way, Madison, CT 06443

      Last Sold Summary

      • 35 Days On Market

  • 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 $617,405

    Last Listing Agent Elise Palacios eXp Realty

    26 Farm View Dr, Madison, CT 06443

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