8,613

Madison, CT Homes

Section Image
    • 263 Legend Hill Rd, Madison, CT 06443

      Est $678,221

      Not Listed For Sale

      263 Legend Hill Rd, Madison, CT 06443

      • 2 Beds
      • 2.5 Baths
      • 2,500 Sq Ft
      • Built 1987
      263 Legend Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Jennifer Trautman Turton William Pitt Sotheby's Int'l

  • 8 Old Route 79, Madison, CT 06443
    8 Old Route 79, Madison, CT 06443
    8 Old Route 79, Madison, CT 06443
    /9

    $1,235,000

    • Land
    • 1.02 Acres
    • $1,210,784 per Acre

    8 Old Route 79, Madison, CT 06443

    Great commercial lot - signalize corner, level and cleared. A rare opportunity for Developers and Investors. Located at the strategic Junction of Old route 79 and Durham Road . One minute to I-95. The property boasts exceptional visibility an accessibility from both north and southbound traffic. Short distance to downtown MADISON, this site is ideal for a variety of commercial ventures, including

    Thomas Simjian Keller Williams Coastal

    8 Old Route 79, Madison, CT 06443
  • 43 Fort Path Rd, Madison, CT 06443

    $503,000

    Sold Jan 30, 2026

    43 Fort Path Rd, Madison, CT 06443

    • 3 Beds
    • 1.5 Baths
    • 1,346 Sq Ft
    • Built 1960

    Last Sold Summary

    • 7% Below List Price
    • $374/SF
    • 40 Days On Market

    Current Estimated Value $525,662

    Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

    43 Fort Path Rd, Madison, CT 06443
    • 279 Legend Hill Rd, Madison, CT 06443

      Est $603,453

      Not Listed For Sale

      279 Legend Hill Rd, Madison, CT 06443

      • 2 Beds
      • 4 Baths
      • 2,476 Sq Ft
      • Built 1985
      279 Legend Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 81 Days On Market

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

  • 45 Island Ave, Madison, CT 06443
    45 Island Ave, Madison, CT 06443
    45 Island Ave, Madison, CT 06443
    /38

    $3,495,000

    $505K 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
  • 129 Acorn Rd, Madison, CT 06443

    $725,000

    Sold Dec 01, 2025

    129 Acorn Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,698 Sq Ft
    • Built 1986

    Last Sold Summary

    • 7% Below List Price
    • $269/SF
    • 103 Days On Market

    Current Estimated Value $759,470

    Last Listing Agent Ann Stewart William Pitt Sotheby's Int'l

    129 Acorn Rd, Madison, CT 06443
    • 75 Legend Hill Rd, Madison, CT 06443

      Est $581,728

      Not Listed For Sale

      75 Legend Hill Rd, Madison, CT 06443

      • 2 Beds
      • 3 Baths
      • 2,140 Sq Ft
      • Built 1985
      75 Legend Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 3 Days On Market

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

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

    $799,000

    Pending
    • 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 Milano Pond Dr, Madison, CT 06443

    $795,000

    Sold Jul 15, 2026

    45 Milano Pond Dr, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 1,908 Sq Ft
    • Built 1991

    Last Sold Summary

    • 10% Above List Price
    • $417/SF
    • 37 Days On Market

    Current Estimated Value $720,499

    Last Listing Agent Rob McConville RE/MAX Heritage

    45 Milano Pond Dr, Madison, CT 06443
    • 22 Legend Hill Rd, Madison, CT 06443

      Est $581,960

      Not Listed For Sale

      22 Legend Hill Rd, Madison, CT 06443

      • 2 Beds
      • 2 Baths
      • 1,946 Sq Ft
      • Built 1984
      22 Legend Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 2 Days On Market

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

  • 476 Summer Hill Rd, Madison, CT 06443
    476 Summer Hill Rd, Madison, CT 06443
    476 Summer Hill Rd, Madison, CT 06443
    /40

    $650,000

    Pending
    • 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
  • 40 Hull Rd, Madison, CT 06443

    $825,000

    Sold May 14, 2026

    40 Hull Rd, Madison, CT 06443

    • 4 Beds
    • 3 Baths
    • 3,462 Sq Ft
    • Built 1963

    Last Sold Summary

    • $238/SF
    • 62 Days On Market

    Current Estimated Value $817,396

    Last Listing Agent Sue Woods William Pitt Sotheby's Int'l

    40 Hull Rd, Madison, CT 06443
    • 105 Legend Hill Rd, Madison, CT 06443

      Est $524,602

      Not Listed For Sale

      105 Legend Hill Rd, Madison, CT 06443

      • 2 Beds
      • 2.5 Baths
      • 1,676 Sq Ft
      • Built 1985
      105 Legend Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Bonnie Fillion Berkshire Hathaway NE Prop.

  • 44 Sterling Park, Madison, CT 06443
    44 Sterling Park, Madison, CT 06443
    44 Sterling Park, Madison, CT 06443
    /30

    $755,000

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 2,317 Sq Ft

    44 Sterling Park, Madison, CT 06443

    Move right into this meticulously maintained home, proudly offered for sale for the very first time by its original owners. This distinctive contemporary 3-bedroom home welcomes you with an inviting natural setting surrounded by mature trees, charming stone walls, and striking rock outcroppings. Inside, abundant natural light fills the thoughtfully designed living spaces, including a formal

    Joanne Combs Dan Combs Real Estate

    44 Sterling Park, Madison, CT 06443
  • 181 Ridge Rd, Madison, CT 06443

    $625,000

    Sold Sep 17, 2025

    181 Ridge Rd, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 1,921 Sq Ft
    • Built 1973

    Last Sold Summary

    • 9% Above List Price
    • $325/SF
    • 32 Days On Market

    Current Estimated Value $639,379

    Last Listing Agent Renee Autorino Coldwell Banker Realty

    181 Ridge Rd, Madison, CT 06443
    • 1086 Durham Rd, Madison, CT 06443

      Est $622,751

      Not Listed For Sale

      1086 Durham Rd, Madison, CT 06443

      • 4 Beds
      • 2 Baths
      • 1,977 Sq Ft
      • Built 1789
      1086 Durham Rd, Madison, CT 06443

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Kimberly O'Donnell William Raveis Real Estate

  • 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
  • 34 Wildcat Springs Dr, Madison, CT 06443

    $1,665,000

    Sold Jul 07, 2026

    34 Wildcat Springs Dr, Madison, CT 06443

    • 5 Beds
    • 5.5 Baths
    • 5,380 Sq Ft
    • Built 1981

    Last Sold Summary

    • 11% Above List Price
    • $309/SF
    • 15 Days On Market

    Current Estimated Value $1,461,500

    Last Listing Agent Rebecca Ellsley Higgins Group Bedford Square

    34 Wildcat Springs Dr, Madison, CT 06443
    • 90 Joshua Trail, Madison, CT 06443

      Est $1,194,638

      Not Listed For Sale

      90 Joshua Trail, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 3,879 Sq Ft
      • Built 1986
      90 Joshua Trail, Madison, CT 06443

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Bob Yostos Coldwell Banker Realty

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

    $769,000

    $20K PRICE DROP Under Contract
    • 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
  • 15D Yankee Glen Rd Unit 15D, Madison, CT 06443

    $415,000

    Sold Sep 26, 2025

    15D Yankee Glen Rd Unit 15D, Madison, CT 06443

    • 2 Beds
    • 2.5 Baths
    • 1,434 Sq Ft
    • Built 1979

    Last Sold Summary

    • 10% Above List Price
    • $289/SF
    • 16 Days On Market

    Current Estimated Value $511,070

    Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

    15D Yankee Glen Rd Unit 15D, Madison, CT 06443
    • 4 Sheffield Ln, Madison, CT 06443

      Est $765,314

      Not Listed For Sale

      4 Sheffield Ln, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,312 Sq Ft
      • Built 1983
      4 Sheffield Ln, Madison, CT 06443

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Kelly Whiteman William Raveis Real Estate

  • 34 Canborne Way, Madison, CT 06443
    34 Canborne Way, Madison, CT 06443
    34 Canborne Way, Madison, CT 06443
    /30

    $485,900

    Pending
    • 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
  • 0 River Rd, Madison, CT 06443

    $2,500,000

    Sold Apr 24, 2026

    0 River Rd, Madison, CT 06443

    • Land
    • 5.56 Acres
    • $449,640 per Acre

    Last Sold Summary

    • 2 Days On Market

    Last Listing Agent Todd Gould William Pitt Sotheby's Int'l

    0 River Rd, Madison, CT 06443
    • 173 Bradley Corners Rd, Madison, CT 06443

      Est $614,820

      Not Listed For Sale

      173 Bradley Corners Rd, Madison, CT 06443

      • 2 Beds
      • 2 Baths
      • 1,383 Sq Ft
      • Built 1987
      173 Bradley Corners Rd, Madison, CT 06443

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Cathy Lynch Coldwell Banker Realty

  • 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 Under Contract
    • 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
  • 110 E Wharf Rd, Madison, CT 06443

    $1,200,000

    Sold Oct 09, 2025

    110 E Wharf Rd, Madison, CT 06443

    • 4 Beds
    • 2 Baths
    • 1,580 Sq Ft
    • Built 1930

    Last Sold Summary

    • 7% Below List Price
    • $759/SF
    • 11 Days On Market

    Current Estimated Value $1,205,726

    Last Listing Agent Lisa Daniele William Raveis Real Estate

    110 E Wharf Rd, Madison, CT 06443
    • 158 Saint Francis Woods Rd, Madison, CT 06443

      Est $786,506

      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

      • 47 Days On Market

      Last Listing Agent Jane Cardarelli William Raveis Real Estate

  • 49 Cottage Rd Unit 3, Madison, CT 06443
    49 Cottage Rd Unit 3, Madison, CT 06443
    49 Cottage Rd Unit 3, Madison, CT 06443
    /27

    $175,000

    Pending
    • 1 Bed
    • 1 Bath
    • 320 Sq Ft

    49 Cottage Rd Unit 3, Madison, CT 06443

    Ever wanted your own perfect summer beach getaway?! This countrycute singlefamily cottage in Madison's Seabreeze Community gives you exactly what you've been dreaming of - a charming, lowkey retreat just minutes from the beach and all the fun of the shoreline. With its cozy, relaxed feel, simple, easyliving layout, and a lovely private patio for morning coffee or evening drinks, it's an ideal

    Kevin Rockoff Rockoff Realty

    49 Cottage Rd Unit 3, Madison, CT 06443
  • 310 Opening Hill Rd, Madison, CT 06443

    $705,000

    Sold Aug 22, 2025

    310 Opening Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft
    • Built 1968

    Last Sold Summary

    • 1% Above List Price
    • $291/SF
    • 5 Days On Market

    Current Estimated Value $739,088

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

    310 Opening Hill Rd, Madison, CT 06443
    • 141 Saint Francis Woods Rd, Madison, CT 06443

      Est $658,750

      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

      • 93 Days On Market

      Last Listing Agent Emily Lovejoy William Raveis Real Estate

  • 81 Legend Hill Rd Unit 81, Madison, CT 06443
    81 Legend Hill Rd Unit 81, Madison, CT 06443
    81 Legend Hill Rd Unit 81, Madison, CT 06443
    /40

    $665,000

    • 2 Beds
    • 2.5 Baths
    • 2,604 Sq Ft

    81 Legend Hill Rd Unit 81, Madison, CT 06443

    Rarely available, this unit is the largest size Townhouse ("Model D") at Legend Hill. It benefits from a quiet location in the complex away from the main road. This unit has been well maintained with excellent natural light and updated neutral decor. Since purchasing, these owners have installed all new flooring throughout first level, in addition to new carpets on second level. Also recently

    Carol Mancini William Pitt Sotheby's Int'l

    81 Legend Hill Rd Unit 81, Madison, CT 06443
  • 983 Boston Post Rd, Madison, CT 06443

    $185,000

    Sold Feb 02, 2026

    983 Boston Post Rd, Madison, CT 06443

    • Land
    • 2.87 Acres
    • $64,460 per Acre

    Last Sold Summary

    • 13% Below List Price
    • 959 Days On Market

    Current Estimated Value $193,115

    Last Listing Agent Jennifer Gurnell William Raveis Real Estate

    983 Boston Post Rd, Madison, CT 06443
    • 115 Saint Francis Woods Rd, Madison, CT 06443

      Est $774,924

      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

      • 73 Days On Market

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

  • 706 Green Hill Rd, Madison, CT 06443
    706 Green Hill Rd, Madison, CT 06443
    706 Green Hill Rd, Madison, CT 06443
    /33

    $925,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 4,191 Sq Ft

    706 Green Hill Rd, Madison, CT 06443

    Situated on over an acre of manicured grounds, this custom-built Colonial blends traditional charm and modern convenience. An inviting front porch welcomes you into a thoughtfully designed floor plan. The main floor flows effortlessly from each room to the next. The eat-in kitchen features an island and sliders to a rear deck. A see-through wood-burning fireplace creates a focal point between the

    Kayla Chasse Compass Connecticut, LLC

    706 Green Hill Rd, Madison, CT 06443
  • 190 Wildcat Rd, Madison, CT 06443

    $1,260,444

    Sold Aug 07, 2026

    190 Wildcat Rd, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 2,451 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Above List Price
    • $514/SF
    • 28 Days On Market

    Current Estimated Value $1,180,267

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    190 Wildcat Rd, Madison, CT 06443
    • 23 Williamsburg Cir, Madison, CT 06443

      Est $886,790

      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

      • 58 Days On Market

      Last Listing Agent Lynne Hubbard Coldwell Banker Realty

  • 50 East St, Madison, CT 06443

    $190,000

    Sold Jul 08, 2026

    50 East St, Madison, CT 06443

    • 2 Beds
    • 1 Bath
    • 480 Sq Ft
    • Built 1961

    Last Sold Summary

    • 5% Below List Price
    • $396/SF
    • 51 Days On Market

    Last Listing Agent Tom Clancy William Pitt Sotheby's Int'l

    50 East St, Madison, CT 06443
    • 195 Summer Hill Rd, Madison, CT 06443

      Est $703,721

      Not Listed For Sale

      195 Summer Hill Rd, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,511 Sq Ft
      • Built 1977
      195 Summer Hill Rd, Madison, CT 06443

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Kelley Vanacore Century 21 AllPoints Realty

  • 48 Allison Dr, Madison, CT 06443

    $1,300,000

    Sold Jul 30, 2026

    48 Allison Dr, Madison, CT 06443

    • 4 Beds
    • 3.5 Baths
    • 3,820 Sq Ft
    • Built 2013

    Last Sold Summary

    • $340/SF
    • 122 Days On Market

    Current Estimated Value $1,393,464

    Last Listing Agent Susan Santoro William Pitt Sotheby's Int'l

    48 Allison Dr, Madison, CT 06443

Showing Results 281 - 320, Page 8 of 18

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