8,613

Madison, CT Homes

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  • 26 Opening Hill Rd, Madison, CT 06443
    26 Opening Hill Rd, Madison, CT 06443
    26 Opening Hill Rd, Madison, CT 06443
    /11

    $1,450,000

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

    26 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

    26 Opening Hill Rd, Madison, CT 06443
  • 146 Chittenden Field Ln, Madison, CT 06443
    146 Chittenden Field Ln, Madison, CT 06443
    146 Chittenden Field Ln, Madison, CT 06443
    /33

    $5,700 Per Month

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft
    • House for Rent

    146 Chittenden Field Ln, Madison, CT 06443

    Available from September 15, 2026, through May 15, 2027, this stunning direct-waterfront academic rental offers an unparalleled coastal lifestyle with breathtaking, panoramic views from almost every room. The bright, sunny interior features an open-concept main level, highlighting a gourmet kitchen with quartz countertops and stainless steel appliances, alongside a generous living and dining area

    Sue Knapp William Pitt Sotheby's Int'l

    146 Chittenden Field Ln, Madison, CT 06443
  • 100 Concord Dr, Madison, CT 06443

    $860,000

    Sold Mar 02, 2026

    100 Concord Dr, Madison, CT 06443

    • 4 Beds
    • 3 Baths
    • 3,517 Sq Ft
    • Built 1978

    Last Sold Summary

    • 1% Above List Price
    • $245/SF
    • 40 Days On Market

    Current Estimated Value $865,757

    Last Listing Agent Amanda Popplewell-Sanson Coldwell Banker Realty

    100 Concord Dr, Madison, CT 06443
    • 35 Lakewood Dr, Madison, CT 06443

      Est $821,113

      Not Listed For Sale

      35 Lakewood Dr, Madison, CT 06443

      • 6 Beds
      • 3.5 Baths
      • 3,146 Sq Ft
      • Built 2001
      35 Lakewood Dr, Madison, CT 06443

      Last Sold Summary

      • 80 Days On Market

      Last Listing Agent Alicia Mahon William Pitt Sotheby's Int'l

  • 177 Warpas Rd, Madison, CT 06443
    177 Warpas Rd, Madison, CT 06443
    177 Warpas Rd, Madison, CT 06443
    /37

    $1,100,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    177 Warpas Rd, Madison, CT 06443

    Welcome to 177 Warpas Road, a beautifully rebuilt 4 bed, 2.1 bath coastal colonial set on 1.84 acres, bordered by 185 acres of protected land trust. A lighted stone column entrance sets the tone for this home where New England style meets thoughtful modern updates. Set well back from the road, enjoy a rare sense of privacy, complemented by a fresh exterior with new windows, siding, entrance

    Margaret Muir William Pitt Sotheby's Int'l

    177 Warpas Rd, Madison, CT 06443
  • 55 Overshores W, Madison, CT 06443
    55 Overshores W, Madison, CT 06443
    55 Overshores W, Madison, CT 06443
    /17

    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft
    • House for Rent

    55 Overshores W, Madison, CT 06443

    AVAILABLE THIS SEPTEMBER 1 TO JUNE 30, 2027. PARTIALLY FURNISHED. PAINTED ALL WHITE. NEWER REFINISHED HARDWOOD FLOORS! NEWER BATHROOM! This open concept 2 bedroom home, hardwood floors, and located in one of the best beach Associations off Neck Road, is perfect for 1-2 people. Fabulous deck off the back of the home provides a perfect place to enjoy a book or glass of wine. Absolutely NO pets, no

    Kirsten Adams William Pitt Sotheby's Int'l

    55 Overshores W, Madison, CT 06443
  • 12 Sportsman Hill Rd, Madison, CT 06443

    $515,000

    Sold Jun 24, 2026

    12 Sportsman Hill Rd, Madison, CT 06443

    • 4 Beds
    • 2 Baths
    • 2,746 Sq Ft
    • Built 1966

    Last Sold Summary

    • 3% Above List Price
    • $188/SF
    • 3 Days On Market

    Current Estimated Value $510,248

    Last Listing Agent Steve Adkins Berkshire Hathaway NE Prop.

    12 Sportsman Hill Rd, Madison, CT 06443
    • 32 Lakewood Dr, Madison, CT 06443

      Est $824,220

      Not Listed For Sale

      32 Lakewood Dr, Madison, CT 06443

      • 3 Beds
      • 4 Baths
      • 3,918 Sq Ft
      • Built 1987
      32 Lakewood Dr, Madison, CT 06443

      Last Sold Summary

      • 97 Days On Market

      Last Listing Agent Cheryl Bertini Berkshire Hathaway NE Prop.

  • 16 North St, Madison, CT 06443
    16 North St, Madison, CT 06443
    16 North St, Madison, CT 06443
    /25

    $149,000

    $5K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 476 Sq Ft

    16 North St, Madison, CT 06443

    Escape to the Connecticut shoreline with this beautifully maintained seasonal cottage in Dud's Village in Madison-the perfect summer retreat just minutes from the beach. Located less than one mile from Hammonasset Beach State Park, Connecticut's largest shoreline park, this charming getaway offers effortless access to two miles of sandy beaches, scenic walking and biking trails, and endless

    Tricia Farin Real Broker CT, LLC

    16 North St, Madison, CT 06443
  • 32 Tuxis Rd, Madison, CT 06443
    32 Tuxis Rd, Madison, CT 06443
    32 Tuxis Rd, Madison, CT 06443
    /35

    $7,500 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,748 Sq Ft
    • House for Rent

    32 Tuxis Rd, Madison, CT 06443

    Relocating to the area? House hunting and yet to find the perfect home? Perhaps looking to spend the academic year along the gorgeous CT shoreline? Look no further as you've found the perfect spot to hang your hat for the academic year here at 32 Tuxis Road. This home is a beautifully restored, quintessential Madison beach house available for rent from September 8, 2026 - June 30, 2027.

    Phoebe Schreiner William Pitt Sotheby's Int'l

    32 Tuxis Rd, Madison, CT 06443
  • Unlisted Address

    $550,000

    Sold Nov 05, 2025

    Unlisted Address

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

    Last Sold Summary

    • 1% Above List Price
    • $351/SF
    • 19 Days On Market

    Current Estimated Value $560,349

    Last Listing Agent Renee Salafia William Raveis Real Estate

    Unlisted Address
    • 1659 Durham Rd, Madison, CT 06443

      Est $632,801

      Not Listed For Sale

      1659 Durham Rd, Madison, CT 06443

      • 3 Beds
      • 2.5 Baths
      • 2,177 Sq Ft
      • Built 1989
      1659 Durham Rd, Madison, CT 06443

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Greg robbins Houlihan Lawrence WD

  • 27 Pine Ridge Dr, Madison, CT 06443
    27 Pine Ridge Dr, Madison, CT 06443
    27 Pine Ridge Dr, Madison, CT 06443
    /13

    $500,000

    • 4 Beds
    • 2 Baths
    • 2,592 Sq Ft

    27 Pine Ridge Dr, Madison, CT 06443

    Opportunity to make sweat equity, this home needs work. Kitchen, living room, dining room, 4 bedrooms, 2 baths, 2 car garage make up this expanded ranch on a lovely level lot on cul-de-sac. The dining room could be a second family room. Open flow for entertaining. Just minutes to downtown Madison and beaches. Top schools. Owner is not in position to make repairs. Perfect home to update to your

    Judy Libby Berkshire Hathaway NE Prop.

    27 Pine Ridge Dr, Madison, CT 06443
  • 156 Kelsey Place, Madison, CT 06443
    156 Kelsey Place, Madison, CT 06443
    156 Kelsey Place, Madison, CT 06443
    /25

    $6,000 Per Month

    • 5 Beds
    • 3 Baths
    • 2,456 Sq Ft
    • House for Rent

    156 Kelsey Place, Madison, CT 06443

    SEPT '26 - MAY '27 ACADEMIC WATERFRONT RENT Plan ahead. With amazing views out over Long Island Sound & beyond this light & bright Beach Colonial was built in 2006 plus has a recent 3 BR addition! Featuring an open floor plan, all in excellent condition with lots of glass & a wrap around deck to take full advantage of it's setting. Located at the very end of a private street this special home is

    Todd Gould William Pitt Sotheby's Int'l

    156 Kelsey Place, Madison, CT 06443
  • 3 Sandgate Cir, Madison, CT 06443

    $475,000

    Sold Jul 10, 2026

    3 Sandgate Cir, Madison, CT 06443

    • 2 Beds
    • 2.5 Baths
    • 1,853 Sq Ft
    • Built 1979

    Last Sold Summary

    • 13% Below List Price
    • $256/SF
    • 164 Days On Market

    Current Estimated Value $508,184

    Last Listing Agent Doris Fallon William Raveis Real Estate

    3 Sandgate Cir, Madison, CT 06443
    • 69 Mendingwall Cir, Madison, CT 06443

      Est $625,180

      Not Listed For Sale

      69 Mendingwall Cir, Madison, CT 06443

      • 3 Beds
      • 2.5 Baths
      • 2,052 Sq Ft
      • Built 1977
      69 Mendingwall Cir, Madison, CT 06443

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

  • 72 Strawberry Hill Rd, Madison, CT 06443
    72 Strawberry Hill Rd, Madison, CT 06443
    72 Strawberry Hill Rd, Madison, CT 06443
    /40

    $1,100,000

    Pending
    • 3 Beds
    • 4 Baths
    • 4,092 Sq Ft

    72 Strawberry Hill Rd, Madison, CT 06443

    This exceptional ranch-style home is set on a beautifully landscaped lot just minutes from Madison's charming town center and sandy beaches. A semi-circular driveway, classic brick and clapboard exterior, stone walls, and mature plantings create a stunning first impression.Step into the sun-filled two-story foyer and discover elegant finishes throughout, including hardwood floors, crown molding,

    Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

    72 Strawberry Hill Rd, Madison, CT 06443
  • 20 Godman Rd, Madison, CT 06443
    20 Godman Rd, Madison, CT 06443
    20 Godman Rd, Madison, CT 06443
    /29

    $4,000 Per Month

    • 4 Beds
    • 3 Baths
    • 2,140 Sq Ft
    • House for Rent

    20 Godman Rd, Madison, CT 06443

    Beautifully maintained annual rental in one of Madison's most desirable neighborhoods. This fully furnished, turnkey home offers 4-5 bedrooms, 3 newly renovated bathrooms, and approximately 2,100 square feet of thoughtfully designed living space. Combining comfort, convenience, and a peaceful natural setting, this exceptional home is just minutes from downtown Madison, beautiful beaches, and

    Kate Jasko Coldwell Banker Realty

    20 Godman Rd, Madison, CT 06443
  • 9 Monroe Ln, Madison, CT 06443

    $640,000

    Sold Jun 30, 2026

    9 Monroe Ln, Madison, CT 06443

    • 4 Beds
    • 2.5 Baths
    • 1,894 Sq Ft
    • Built 1966

    Last Sold Summary

    • 1% Above List Price
    • $338/SF
    • 63 Days On Market

    Current Estimated Value $637,960

    Last Listing Agent Karen Lee Coldwell Banker Realty

    9 Monroe Ln, Madison, CT 06443
    • 7 Twilight Dr, Madison, CT 06443

      Est $700,252

      Not Listed For Sale

      7 Twilight Dr, Madison, CT 06443

      • 3 Beds
      • 2.5 Baths
      • 2,646 Sq Ft
      • Built 1973
      7 Twilight Dr, Madison, CT 06443

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Emily Lovejoy William Raveis Real Estate

  • 89 Cottage Rd, Madison, CT 06443
    89 Cottage Rd, Madison, CT 06443
    89 Cottage Rd, Madison, CT 06443
    /34

    $350,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 764 Sq Ft

    89 Cottage Rd, Madison, CT 06443

    Highly sought after and rarely available-until now! 89-2 Cottage Road is the seasonal Madison cottage you'll want to run toward. Proudly part of the historic Little Colony community settled by veterans just after World War II, this lovely abode offers two bedrooms and a thoughtfully renovated full bath. The heart of the home is a generous, open-concept living space featuring a beautifully updated

    Melanie Abbott William Pitt Sotheby's Int'l

    89 Cottage Rd, Madison, CT 06443
  • 137 Liberty St, Madison, CT 06443

    $2,200,000

    Sold Aug 06, 2026

    137 Liberty St, Madison, CT 06443

    • 5 Beds
    • 5.5 Baths
    • 5,543 Sq Ft
    • Built 1816

    Last Sold Summary

    • 15% Below List Price
    • $397/SF
    • 110 Days On Market

    Last Listing Agent Alison Gould Gould Group LLC

    137 Liberty St, Madison, CT 06443
    • 1474 Durham Rd, Madison, CT 06443

      Est $611,175

      Not Listed For Sale

      1474 Durham Rd, Madison, CT 06443

      • 4 Beds
      • 3.5 Baths
      • 2,740 Sq Ft
      • Built 1984
      1474 Durham Rd, Madison, CT 06443

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Alicia Mahon William Pitt Sotheby's Int'l

  • 238 Scotland Rd, Madison, CT 06443
    238 Scotland Rd, Madison, CT 06443
    238 Scotland Rd, Madison, CT 06443
    /40

    $725,000

    $50K PRICE DROP Pending
    • 5 Beds
    • 4 Baths
    • 3,224 Sq Ft

    238 Scotland Rd, Madison, CT 06443

    Welcome to 238 Scotland Road, a rare 5-bedroom home with private in-law accommodations, pool, situated on nearly an acre of privacy. A lovingly cared-for home offering exceptional space, comfort, and versatility. Features include hardwood floors throughout, central air conditioning, and a beautiful new primary suite designed for relaxation and convenience. The heart of the home is the updated

    Debra Pardales William Pitt Sotheby's Int'l

    238 Scotland Rd, Madison, CT 06443
  • 15 Buttonball Ln, Madison, CT 06443

    $900,000

    Sold Nov 17, 2025

    15 Buttonball Ln, Madison, CT 06443

    • 4 Beds
    • 3 Baths
    • 2,576 Sq Ft
    • Built 1969

    Last Sold Summary

    • 6% Above List Price
    • $349/SF
    • 55 Days On Market

    Current Estimated Value $901,055

    Last Listing Agent Cathy Lynch Coldwell Banker Realty

    15 Buttonball Ln, Madison, CT 06443
    • 2 Cornfield Ln, Madison, CT 06443

      Est $558,195

      Not Listed For Sale

      2 Cornfield Ln, Madison, CT 06443

      • 3 Beds
      • 2.5 Baths
      • 1,966 Sq Ft
      • Built 1982
      2 Cornfield Ln, Madison, CT 06443

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Shoreline Homes Team William Raveis Real Estate

  • 36 Devonshire Ln, Madison, CT 06443
    36 Devonshire Ln, Madison, CT 06443
    36 Devonshire Ln, Madison, CT 06443
    /40

    $799,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,472 Sq Ft

    36 Devonshire Ln, Madison, CT 06443

    Welcome to this exquisite 4-bedroom, 2.5-bath colonial home, where classic design meets modern luxury. This property offers an ideal combination of space, style, and comfort. Enter an inviting entryway into a spacious foyer with beautiful hardwood floors, that flow throughout the main level. The formal living room with large windows and French doors allows for natural light, while the formal

    Robert Sacco Coldwell Banker Realty

    36 Devonshire Ln, Madison, CT 06443
  • 148 Country Way, Madison, CT 06443

    $1,077,000

    Sold Dec 05, 2025

    148 Country Way, Madison, CT 06443

    • 5 Beds
    • 2.5 Baths
    • 3,136 Sq Ft
    • Built 1996

    Last Sold Summary

    • 5% Above List Price
    • $343/SF
    • 62 Days On Market

    Current Estimated Value $1,104,208

    Last Listing Agent Janet Peckinpaugh William Pitt Sotheby's Int'l

    148 Country Way, Madison, CT 06443
    • 24 Pond View Ln, Madison, CT 06443

      Est $637,797

      Not Listed For Sale

      24 Pond View Ln, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,426 Sq Ft
      • Built 1985
      24 Pond View Ln, Madison, CT 06443

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Jonathan Gineo Silver and Oak Realty

  • 44 Winding Rd, Madison, CT 06443
    44 Winding Rd, Madison, CT 06443
    44 Winding Rd, Madison, CT 06443
    /22

    $400,000

    • 4 Beds
    • 2 Baths
    • 1,698 Sq Ft

    44 Winding Rd, Madison, CT 06443

    Situated on 1.62 acres, this 4-bedroom, 2-bath ranch offers endless potential for investors, contractors, or buyers looking to create their dream home. The expansive backyard, once used as a sports field, provides an incredible amount of usable outdoor space that's rarely found. Inside, you'll find hardwood floors in many rooms, a spacious living room with a fireplace, a 2-car attached garage,

    Mark Mermelstein eXp Realty

    44 Winding Rd, Madison, CT 06443
  • 2 Esterly Farms Rd, Madison, CT 06443

    $400,000

    Sold Mar 27, 2026

    2 Esterly Farms Rd, Madison, CT 06443

    • 1 Bed
    • 1.5 Baths
    • 1,344 Sq Ft
    • Built 1985

    Last Sold Summary

    • $298/SF
    • 52 Days On Market

    Current Estimated Value $402,413

    Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

    2 Esterly Farms Rd, Madison, CT 06443
    • 68 White Cedar Dr, Madison, CT 06443

      Est $695,762

      Not Listed For Sale

      68 White Cedar Dr, Madison, CT 06443

      • 3 Beds
      • 2.5 Baths
      • 2,030 Sq Ft
      • Built 1983
      68 White Cedar Dr, Madison, CT 06443

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

  • 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
  • 28 Riverside Ln, Madison, CT 06443

    $1,600,000

    Sold Jan 23, 2026

    28 Riverside Ln, Madison, CT 06443

    • 3 Beds
    • 2.5 Baths
    • 2,398 Sq Ft
    • Built 2003

    Last Sold Summary

    • $667/SF
    • 14 Days On Market

    Current Estimated Value $1,544,381

    Last Listing Agent Diana Hartman William Pitt Sotheby's Int'l

    28 Riverside Ln, Madison, CT 06443
    • 35 White Cedar Dr, Madison, CT 06443

      Est $679,496

      Not Listed For Sale

      35 White Cedar Dr, Madison, CT 06443

      • 4 Beds
      • 2.5 Baths
      • 2,150 Sq Ft
      • Built 1984
      35 White Cedar Dr, Madison, CT 06443

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

  • 6 Ladshaw Dr, Madison, CT 06443
    6 Ladshaw Dr, Madison, CT 06443
    6 Ladshaw Dr, Madison, CT 06443
    /27

    $487,000

    $53K PRICE DROP
    • 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
  • 247 C Old Toll Rd, Madison, CT 06443

    $220,000

    Sold Mar 25, 2026

    247 C Old Toll Rd, Madison, CT 06443

    • Land
    • 26.2 Acres
    • $8,397 per Acre

    Last Sold Summary

    • 43% Below List Price
    • 106 Days On Market

    Last Listing Agent Allyson Cotton William Pitt Sotheby's Int'l

    247 C Old Toll Rd, Madison, CT 06443
    • 145 Genesee Ln, Madison, CT 06443

      Est $951,207

      Not Listed For Sale

      145 Genesee Ln, Madison, CT 06443

      • 4 Beds
      • 3.5 Baths
      • 4,366 Sq Ft
      • Built 1995
      145 Genesee Ln, Madison, CT 06443

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Rose Ciardiello William Raveis Real Estate

  • 32 North St, Madison, CT 06443
    32 North St, Madison, CT 06443
    32 North St, Madison, CT 06443
    /20

    $149,900

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 592 Sq Ft

    32 North St, Madison, CT 06443

    With a new roof in process, 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

    Melanie Abbott William Pitt Sotheby's Int'l

    32 North St, Madison, CT 06443
  • 109 Boston Post Rd, Madison, CT 06443

    $935,570

    Sold Aug 14, 2025

    109 Boston Post Rd, Madison, CT 06443

    • 3 Beds
    • 3 Baths
    • 2,728 Sq Ft
    • Built 1854

    Last Sold Summary

    • 6% Below List Price
    • $343/SF
    • 42 Days On Market

    Current Estimated Value $1,001,742

    Last Listing Agent John Hill Seabury Hill REALTORS

    109 Boston Post Rd, Madison, CT 06443

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