8,623

Madison, CT Homes

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  • 31 Meadowbrook Rd, Madison, CT 06443
    31 Meadowbrook Rd, Madison, CT 06443
    31 Meadowbrook Rd, Madison, CT 06443
    /40

    $850,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,360 Sq Ft

    31 Meadowbrook Rd, Madison, CT 06443

    Nestled in a quiet cul-de-sac within the desirable Richborough subdivision, this 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of comfort, convenience, and charm, just minutes from town beaches and the vibrant town center. Step through the front foyer into a light-filled interior featuring hardwood floors, crown molding, and recessed lighting throughout. The eat-in kitchen offers

    Rose Ciardiello William Raveis Real Estate

    31 Meadowbrook Rd, Madison, CT 06443
  • 43 Soundview Ave, Madison, CT 06443
    43 Soundview Ave, Madison, CT 06443
    43 Soundview Ave, Madison, CT 06443
    /31

    $8,949 per month

    • 4 Beds
    • 3 Baths
    • 1,869 Sq Ft
    • House for Rent

    43 Soundview Ave, Madison, CT 06443

    Fabulous academic rental available 10/1 through May 31st 2025. This direct waterfront four bedroom home set on a one of kind property with access to a private beach. Enjoy fabulous views from your deck, large yard and tidal pool. Plenty of space for everyone with a bedroom with full bath on the main level, Primary en suite on the second floor with private balcony and two additional bedrooms with

    Sue Knapp William Pitt Sotheby's Int'l

    43 Soundview Ave, Madison, CT 06443
  • 63 Circle Beach Rd, Madison, CT 06443

    $850,000 Sold May 28, 2025

    • 1,037 Sq Ft
    • $820/SF
    • 38 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1940

    63 Circle Beach Rd, Madison, CT 06443

    Discover the charm of DIRECT WATERFRONT living with this circa 1940 cottage, perfectly situated on a .11-acre sandy beach along the shores of Long Island Sound. Featuring 3 bedrooms and 2 full baths, this 1,000+ SF home offers a seamless blend of coastal charm and modern convenience, including mini split systems for heating and cooling. The open-concept kitchen, dining, and living areas are

    Rose Ciardiello William Raveis Real Estate

    63 Circle Beach Rd, Madison, CT 06443
  • 48 Shepherds Trail, Madison, CT 06443
    48 Shepherds Trail, Madison, CT 06443
    48 Shepherds Trail, Madison, CT 06443
    /40

    $899,000 Under Contract

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

    48 Shepherds Trail, Madison, CT 06443

    Welcome to your private oasis-This one-of-a-kind Contemporary Colonial home offers 4 bedrooms, 2.5 baths, and a versatile floor plan designed for both grand entertaining & everyday comfort. Step into the impressive foyer, where an expansive living room & formal dining area set the stage for elegant gatherings. The kitchen at the heart of the main level gleams with granite countertops,

    Erin Connelly Coldwell Banker Realty

    48 Shepherds Trail, Madison, CT 06443
  • 6 Apple Way, Madison, CT 06443

    $543,800 Sold May 21, 2025

    • 1,932 Sq Ft
    • $281/SF
    • 194 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1994

    6 Apple Way, Madison, CT 06443

    Welcome to the pick of the crop at The Orchards, 6 Apple Way. This in-town stand alone home is being offered for the first time in 28 years. Its ideal location is close to beaches, train station, restaurants and so much more. With newer appliances, less than 5 years old hot water heater, a/c compressors, and Generac generator you will be pleased with the maintenance record. One of the largest

    Julie Ovian William Pitt Sotheby's Int'l

    6 Apple Way, Madison, CT 06443
  • 14 Martleshamheath Ln, Madison, CT 06443
    14 Martleshamheath Ln, Madison, CT 06443
    14 Martleshamheath Ln, Madison, CT 06443
    /40

    $697,900 Open Sat 10AM - 12PM

    • 3 Beds
    • 2.5 Baths
    • 2,762 Sq Ft

    14 Martleshamheath Ln, Madison, CT 06443

    Nestled in Desired Neighborhood Beautiful Updated Colonial on 3.46-acres on a quiet cul-de-sac in Seaside Town of Madison. Open casual living, formal spaces, walkout lower level: Natural light fills this home. 2 story Foyer invites you into a Lovely Home offering Dine in Kitchen, Island, Granite, tile, double stainless sink & appliances, recess lighting: Powder Room, Formal Dining & Living Rooms

    Karen Martin Century 21 AllPoints Realty

    14 Martleshamheath Ln, Madison, CT 06443
  • 875 Boston Post Rd Unit 3, Madison, CT 06443

    $799,000 Sold May 20, 2025

    • 1,513 Sq Ft
    • $528/SF
    • 38 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1900

    875 Boston Post Rd Unit 3, Madison, CT 06443

    Sophisticated, Fully Renovated Condominium in the Heart of Downtown Madison. This beautifully reimagined residence offers the perfect blend of classic charm and modern luxury. Nestled in the vibrant center of Madison, this sun-filled condominium features a thoughtfully designed open-concept floor plan, custom cabinetry, and rich hardwood flooring throughout-all while preserving touches of

    Cathy Lynch Coldwell Banker Realty

    875 Boston Post Rd Unit 3, Madison, CT 06443
  • 3 Essex Ln Unit 3, Madison, CT 06443
    3 Essex Ln Unit 3, Madison, CT 06443
    3 Essex Ln Unit 3, Madison, CT 06443
    /37

    $529,000 Open Sun 11:30AM - 1:30PM

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

    3 Essex Ln Unit 3, Madison, CT 06443

    Charming Ranch Retreat in Kensington Acres North! Tucked away at the end of a quiet cul-de-sac in the sought-after Kensington Acres North community, 3 Essex Lane offers the perfect blend of privacy, comfort, and convenience. This inviting 2-bedroom, 2-bathroom ranch is a rare find, a serene, natural setting-just minutes from Madison's vibrant town center, beaches, and train station. Step inside

    Nancy Bullis Great Estates, CT

    3 Essex Ln Unit 3, Madison, CT 06443
  • 16 Canborne Way Unit 16, Madison, CT 06443

    $620,000 Sold May 20, 2025

    • 1,424 Sq Ft
    • $435/SF
    • 42 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1979

    16 Canborne Way Unit 16, Madison, CT 06443

    Desirable Windermere East with views of the Hammonasset River, a private patio, a FULL basement and BEAUTIFULLY renovated! This ranch is in mint condition with an expanded and fully renovated kitchen with an island, granite counters and stainless steel appliances. The open concept is one of the special features of this unit. Along with the cozy family room with a cathedral ceiling, built-ins, a

    Laurie Mazzeo William Pitt Sotheby's Int'l

    16 Canborne Way Unit 16, Madison, CT 06443
  • 2 Brantwood Dr, Madison, CT 06443
    2 Brantwood Dr, Madison, CT 06443
    2 Brantwood Dr, Madison, CT 06443
    /26

    $325,000 Open Sat 11AM - 1PM

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

    2 Brantwood Dr, Madison, CT 06443

    Welcome to this move in ready townhouse located just a short walk to downtown Madison. Newly installed sidewalks make it convenient to visit everything Madison has to offer - shopping, movie theater, restaurants, farmers market and Sunday evening concerts. This unit offers 2 bedrooms, 1.2 baths with over 1300 s.f. The updated kitchen has shaker cabinets, granite countertops and stainless steel

    Rebecca Ferguson Coldwell Banker Realty

    2 Brantwood Dr, Madison, CT 06443
  • 128 Horse Pond Rd, Madison, CT 06443

    $850,000 Sold May 19, 2025

    • 2,578 Sq Ft
    • $330/SF
    • 62 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1999

    128 Horse Pond Rd, Madison, CT 06443

    Experience the epitome of one-level living in this impeccably maintained home, where pride of ownership shines in every corner. Gracious entry welcomes you into the open & airy floor plan of this bright, classically designed residence. The heart of the home is the great room, bathed in natural light from numerous windows & anchored by an inviting stone, floor-to-ceiling wood-burning fireplace.

    Amy Kirst William Pitt Sotheby's Int'l

    128 Horse Pond Rd, Madison, CT 06443
  • 273 Legend Hill Rd, Madison, CT 06443
    273 Legend Hill Rd, Madison, CT 06443
    273 Legend Hill Rd, Madison, CT 06443
    /33

    $545,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,922 Sq Ft

    273 Legend Hill Rd, Madison, CT 06443

    Meticulous condo freshly painted, new hardwood floors, carpeting and more. 2 bedrooms on the main level, living room with gas fireplace, dining area, large kitchen with newer dishwasher, family room with many windows and a distant view of Long Island Sound on a clear day. There is additional sf in the 2 rooms in lower level and a large storage area. Walk over to the pool, enjoy the historic

    Judy Libby Berkshire Hathaway NE Prop.

    273 Legend Hill Rd, Madison, CT 06443
  • 23 Blueberry Hill Dr, Madison, CT 06443

    $850,000 Sold May 16, 2025

    • 3,692 Sq Ft
    • $230/SF
    • 61 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2001

    23 Blueberry Hill Dr, Madison, CT 06443

    This lovingly kept home is is being offered for the first time by its original owner. Set on a cul-de-sac in an established neighborhood, this property offers unparalleled privacy with nearly 3 acres of land, further enhanced by Madison Land Conservation which almost completely surrounds this interior lot. The expansive yard and 25x12 deck provide perfect spots to sit and enjoy the nature around

    Cortney Emshwiller-Swokla Coldwell Banker Realty

    23 Blueberry Hill Dr, Madison, CT 06443
  • 73 Legend Hill Rd, Madison, CT 06443
    73 Legend Hill Rd, Madison, CT 06443
    73 Legend Hill Rd, Madison, CT 06443
    /33

    $580,000 Open Sat 11AM - 12:30PM

    • 2 Beds
    • 2.5 Baths
    • 2,256 Sq Ft

    73 Legend Hill Rd, Madison, CT 06443

    Welcome to this beautifully maintained two-bedroom, 2.1-bath townhouse condominium in Madison's sought-after Legend Hill community. Set within an 88-acre private enclave of 90 homes, Legend Hill is rich in history and charm, with residences thoughtfully arranged around the historic Northam Manor. Perched on one of the highest elevations between Boston and the New York shoreline, the community

    Dana Weinstein Coldwell Banker Realty

    73 Legend Hill Rd, Madison, CT 06443
  • 24 Kingsbridge Way Unit 24, Madison, CT 06443

    $655,000 Sold May 16, 2025

    • 2,538 Sq Ft
    • $258/SF
    • 36 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1988

    24 Kingsbridge Way Unit 24, Madison, CT 06443

    PRICE REDUCED!!! Make your move NOW! A secluded community with a sanctuary feel awaits you at highly desirable Strathmore Farms, a private enclave of 23 free-standing homes bordering the Hammonasset River & salt meadow. Located just a few short minutes to downtown Madison, this gracious home offers amazing outdoor and indoor space, large banquet sized rooms and unlimited potential! 9 foot

    Sarah David Higgins Group Real Estate

    24 Kingsbridge Way Unit 24, Madison, CT 06443
  • 118 Flintlock Rd, Madison, CT 06443
    118 Flintlock Rd, Madison, CT 06443
    118 Flintlock Rd, Madison, CT 06443
    /29

    $725,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    118 Flintlock Rd, Madison, CT 06443

    Mid century modern, custom designed and built expanded ranch surrounded by many mature plantings provides sought after one level living. Wonderful open floor plan with picture windows in the living room and eat-in kitchen/dining area look onto the lovely rolling front lawn. A large bar is conveniently located in the kitchen designed for more casual dining. Six rooms, 3 bedrooms and 2 full baths.

    Faith Whitehead William Raveis Real Estate

    118 Flintlock Rd, Madison, CT 06443
  • 52 Allison Dr, Madison, CT 06443

    $1,300,000 Sold May 16, 2025

    • 4,295 Sq Ft
    • $303/SF
    • 179 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 2009

    52 Allison Dr, Madison, CT 06443

    Exceptional 4 bedroom 3 bath professionally landscaped 4295 square foot Colonial located in Madison's desirable Southwick neighborhood. A grand two story foyer with a chandelier featuring a curved stairway welcomes you! A chefs delight gourmet island kitchen with granite counters, top of the line stainless steel appliances with gas cook top is ideal for entertaining. The living room with a stone

    Vincent Engingro William Raveis Real Estate

    52 Allison Dr, Madison, CT 06443
  • 77 E Wharf Rd, Madison, CT 06443
    77 E Wharf Rd, Madison, CT 06443
    77 E Wharf Rd, Madison, CT 06443
    /38

    $4,000,000

    • 5 Beds
    • 6.5 Baths
    • 4,450 Sq Ft

    77 E Wharf Rd, Madison, CT 06443

    Welcome to 77 East Wharf! This beautifully designed five-bedroom Cape Cod-style home is perfectly situated high on the property to capture breathtaking views of the Long Island Sound and tranquil Fence Creek. Ideal for entertaining or hosting beach-loving visitors, this home also includes a charming one-bedroom apartment over the garage. Begin your experience with a private walkway bordered by a

    Meig Walz Newcomb Coldwell Banker Realty

    77 E Wharf Rd, Madison, CT 06443
  • 26 Jenda Way, Madison, CT 06443

    $705,000 Sold May 15, 2025

    • 2,147 Sq Ft
    • $328/SF
    • 35 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1987

    26 Jenda Way, Madison, CT 06443

    Discover the perfect blend of comfort and elegance in the sought-after Milano Pond neighborhood. This classic New England home, nestled at the end of a peaceful cul-de-sac, boasts an inviting open-concept design with gleaming hardwood floors that seamlessly connect the living and family rooms to the tiled kitchen and dining area. The kitchen, the hub of the home, is outfitted with crisp, white

    Sue Knapp William Pitt Sotheby's Int'l

    26 Jenda Way, Madison, CT 06443
  • 37 Sheffield Ln, Madison, CT 06443
    37 Sheffield Ln, Madison, CT 06443
    37 Sheffield Ln, Madison, CT 06443
    /40

    $770,000

    • 4 Beds
    • 2.5 Baths
    • 2,989 Sq Ft

    37 Sheffield Ln, Madison, CT 06443

    Welcome home! This lovingly maintained 4-bedroom colonial is Located at the end of a beautiful cul-de-sac neighborhood only 15 minutes to the quaint Madison downtown and its beaches. Plenty of room for everyone including the family dog in this 2377 square foot home with finished walkout basement and invisible fence. Hardwood floors throughout with a lovely woodburning woodstove in the family

    Jane Cardarelli William Raveis Real Estate

    37 Sheffield Ln, Madison, CT 06443
  • 1928 Durham Rd, Madison, CT 06443

    $512,000 Sold May 15, 2025

    • 1,608 Sq Ft
    • $318/SF
    • 56 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1747

    1928 Durham Rd, Madison, CT 06443

    Step into this one-of-a-kind 1747 post-and-beam modern farmhouse that blends historic charm with contemporary luxury. Nestled on a serene and private 1.2-acre lot, this property offers the perfect retreat while being thoughtfully updated for modern living. The interior boasts beautifully preserved, original hardwood floors that exude timeless character throughout the home. A fully renovated

    Tom Vanacore Century 21 AllPoints Realty

    1928 Durham Rd, Madison, CT 06443
  • 28 Brantwood Dr, Madison, CT 06443
    28 Brantwood Dr, Madison, CT 06443
    28 Brantwood Dr, Madison, CT 06443
    /29

    $250,000

    • 1 Bed
    • 1 Bath
    • 863 Sq Ft

    28 Brantwood Dr, Madison, CT 06443

    Charming 1-Bedroom Condo with Spacious Layout in Prime Madison Location! Welcome to this beautifully designed 1-bedroom, 1-bath condo offering a thoughtfully laid-out living space with an open and airy feel. Step into a bright and expansive living room, perfect for entertaining or relaxing, with plenty of space for both lounging and dining. The kitchen features a functional layout with generous

    Jules Gaughran - Etes William Pitt Sotheby's Int'l

    28 Brantwood Dr, Madison, CT 06443
  • 7 Wildcat Rd, Madison, CT 06443

    $870,000 Sold May 13, 2025

    • 3,258 Sq Ft
    • $267/SF
    • 26 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2007

    7 Wildcat Rd, Madison, CT 06443

    Nestled in the desirable Century Oak subdivision, this meticulously maintained home exudes charm and modern convenience. With its elegant crown molding and soaring 9-foot ceilings, every room feels spacious and airy. The gleaming hardwood floors throughout add a touch of warmth and sophistication, enhancing the home's overall appeal. The open floor plan seamlessly connects the living, dining, and

    Cathy Lynch Coldwell Banker Realty

    7 Wildcat Rd, Madison, CT 06443
  • 1281 Durham Rd, Madison, CT 06443
    1281 Durham Rd, Madison, CT 06443
    1281 Durham Rd, Madison, CT 06443
    /27

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 2,192 Sq Ft

    1281 Durham Rd, Madison, CT 06443

    CHARMING LARGE MADISON MOTHER /DAUGHTER 2 BEDROOMS LARGE MODERN CHEFS KITCHEN LIVING ROOM WITH FIREPLACE LARGE BATH LAUNDRY AND BONUSROOM EXTENDING THE WIDTH OF THE HOUSE UPSTAIRS ALL NEW A LARGE LIVING ROOM KITCHEN BATH 2 BEDROOMS AND A PRIVATE ENCLOSED BALCONY OVERLOOKING THE BEAUTIFUL JUST SHY 1/2 ACRE PRIVATE YARD. AND GARAGE. A MUST SEE A TRUE FAMILY HOME !!!

    Dan Rocano Exit Realty Everyday

    1281 Durham Rd, Madison, CT 06443
  • 31 Governors Way, Madison, CT 06443

    $1,600,000 Sold May 12, 2025

    • 4,350 Sq Ft
    • $368/SF
    • 40 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 2006

    31 Governors Way, Madison, CT 06443

    Nantucket elegance in the heart of Madison and quite simply, in a class of its own! This thoughtfully crafted home was custom built in 2006 with every detail in mind and a style reminiscent of those you would find on the Cape & Islands. The building lot was selected for it's prominence in the neighborhood, sited on the highest elevation. The professionally landscaped grounds were designed to

    Phoebe Finch William Pitt Sotheby's Int'l

    31 Governors Way, Madison, CT 06443
  • 94 Boston Post Rd, Madison, CT 06443
    94 Boston Post Rd, Madison, CT 06443
    94 Boston Post Rd, Madison, CT 06443
    /31

    $658,000

    • 2 Beds
    • 2.5 Baths
    • 1,668 Sq Ft

    94 Boston Post Rd, Madison, CT 06443

    UNIQUE CONTEMPORARY HOME SURROUNDED BY NATURE. CONVENIENTLY LOCATED IN SMALL ENCLAVE OF THREE HOMES, SET BACK OFF THE BOSTON POST ROAD. COMPLETELY RENOVATED IN 2013-2015. NEW ROOF, KITCHEN, BATHS, FLOORING, HEATING, A/C, WINDOWS, STAIRCASE, LIGHTING,ELECTRICAL , TONGUE AND GROOVE PINE VAULTED CEILING, AND MORE. LIKE WALKING IN ARCHITECTAUL DIGEST MAGAIZINE! FIRST FLOOR MASTERBEDROOM WITH GORGEOUS

    Camille Ackermann Berkshire Hathaway NE Prop.

    94 Boston Post Rd, Madison, CT 06443
  • 16 Harkness Dr, Madison, CT 06443

    $546,000 Sold May 09, 2025

    • 1,596 Sq Ft
    • $342/SF
    • 36 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2003

    16 Harkness Dr, Madison, CT 06443

    A special retreat enveloped into the landscape. Tucked into a wooded lot with a meandering brook. Gardens and stonewalls abound with a show of soft lighting after dusk. This home was custom designed with a contemporary cottage feel. The Nordic design and quality of the Rais wood burning stove rests proudly in front of native wooden slabs adding to the organic design. Screened porches run the

    Heather Clinton Berkshire Hathaway NE Prop.

    16 Harkness Dr, Madison, CT 06443

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