8,622

Madison, CT Homes

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  • 33 North St, Madison, CT 06443
    33 North St, Madison, CT 06443
    33 North St, Madison, CT 06443
    /27

    $165,000

    • 2 Beds
    • 1 Bath
    • 630 Sq Ft

    33 North St, Madison, CT 06443

    Charming Seasonal Cottage in Madison, CT - Steps from the Beach! Welcome to your perfect summer getaway! This cozy and comfortable seasonal cottage offers 629 square feet of well-utilized living space in a family and pet-friendly community, just a short stroll from Hammonasset Beach, a scenic salt pond, and the Hammonasset River. Tucked away in one of Madison's most desirable cottage villages,

    Agent Photo

    Joe Rodorigo

    Keystone Realty, LLC

    (203) 872-6960

    33 North St, Madison, CT 06443
  • 41 Harbor Ave, Madison, CT 06443
    41 Harbor Ave, Madison, CT 06443
    41 Harbor Ave, Madison, CT 06443
    /28

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,640 Sq Ft
    • House for Rent

    41 Harbor Ave, Madison, CT 06443

    ACADEMIC RENTAL, Available APPROX NOVEMBER 1ST TO MAY 31, 2026. Adorable & cozy yearround bungalow in a cul-de-sac, Beach community. 2/3 bedrooms & 2 full baths. Enclosed porch with wrap-around sliders lead out to a deck and nice backyard....freshly painted with some new flooring/carpeting and refreshed bathrooms and kitchen. A sweet place to be. Minutes from Madison Center, commuting routes and

    Alison Gould Gould Group LLC

    41 Harbor Ave, Madison, CT 06443
  • 123 Five Fields Rd, Madison, CT 06443

    $860,000 Sold Aug 29, 2025

    • 3,664 Sq Ft
    • $235/SF
    • 19 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1969

    123 Five Fields Rd, Madison, CT 06443

    Location!!! Welcome to 123 Five Fields Road, tucked away on a peaceful cul-de-sac in one of Madison's most sought-after neighborhoods. This classic 5-bedroom, 2.5-bath Colonial offers a rare blend of privacy, space, and shoreline living. Set on 1.09 acres, the property features an in-ground pool, multiple decks and patios, and direct access to the Hammonasset River-ideal for entertaining or

    Allison Ciarcia William Raveis Real Estate

    123 Five Fields Rd, Madison, CT 06443
  • 40 Legend Hill Rd, Madison, CT 06443
    40 Legend Hill Rd, Madison, CT 06443
    40 Legend Hill Rd, Madison, CT 06443
    /29

    $515,000

    • 2 Beds
    • 2.5 Baths
    • 2,320 Sq Ft

    40 Legend Hill Rd, Madison, CT 06443

    Carefree Living in Madison's Premier Legend Hill Community Set on over 80 acres of beautifully landscaped grounds, Legend Hill offers resort-style amenities including a historic clubhouse, inground pool, and tennis/pickleball courts-all just minutes from Madison's charming town center and sandy beaches. This meticulously maintained ranch style 2-bedroom unit has a lovely kitchen which opens to

    Agent Photo

    Cathy Lynch

    Coldwell Banker Realty

    (203) 779-6103

    40 Legend Hill Rd, Madison, CT 06443
  • 30 Lawson Dr, Madison, CT 06443
    30 Lawson Dr, Madison, CT 06443
    30 Lawson Dr, Madison, CT 06443
    /12

    $5,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,918 Sq Ft
    • House for Rent

    30 Lawson Dr, Madison, CT 06443

    Beautifully furnished 3 bed, 2.1 baths house a short walk from East Wharf Beach. Rebuilt from top to bottom in 2018-19 with an open floor plan. A fenced back yard has a bluestone terrace. The living room features a gas fireplace, a well equipped kitchen has a large pantry and a vaulted ceiling family room provides ample room for all. First floor en-suite primary bedroom. Two spacious bedrooms and

    Margaret Muir William Pitt Sotheby's Int'l

    30 Lawson Dr, Madison, CT 06443
  • 659 Summer Hill Rd, Madison, CT 06443

    $960,000 Sold Aug 29, 2025

    • 2,558 Sq Ft
    • $375/SF
    • 49 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1779

    659 Summer Hill Rd, Madison, CT 06443

    Have Fun! Summer: pool, large deck, fenced yard, and central AC! Winter: Fireplaces, holiday meals, room for guests. Yesterday's charm & all the conveniences of today (new roof, new boiler, new central AC, Updated Kitchen) With wide plank Chestnut floors and 3 fireplaces on the first floor: the vintage house charm with current comfort is inviting! Access to the deck from the Dining Room and

    Leigh Whiteman William Raveis Real Estate

    659 Summer Hill Rd, Madison, CT 06443
  • 728 Durham Rd, Madison, CT 06443
    728 Durham Rd, Madison, CT 06443
    728 Durham Rd, Madison, CT 06443
    /15

    $173,500

    • Land
    • 1.55 Acres
    • $111,935 per Acre

    728 Durham Rd, Madison, CT 06443

    Imagine building your dream home on this picturesque 1.55-acre lot in Madison, Connecticut, offering seasonal views of the serene Hog Pond. Throughout the year, enjoy the changing scenery and abundant wildlife, with opportunities for ice skating and hockey on the pond during winter months. The property includes a recent survey with topographical details and a septic design, pending only perc

    Agent Photo

    Gene Pica

    RE/MAX Alliance

    (475) 290-6060

    728 Durham Rd, Madison, CT 06443
  • 14 Neptune Ave, Madison, CT 06443
    14 Neptune Ave, Madison, CT 06443
    14 Neptune Ave, Madison, CT 06443
    /34

    $7,000 per month

    • 4 Beds
    • 3 Baths
    • 2,757 Sq Ft
    • House for Rent

    14 Neptune Ave, Madison, CT 06443

    FANTASTIC LOCATION! This 4 bedroom Cape Style home sits on Neptune Ave, just off Liberty Street, with easy access to the private Barberry Farms Assoc Beach and downtown Madison. The first floor hosts a Living Room with fireplace, Dining Room, Den, Sunroom, Primary Bedroom (ensuite) and another bedroom with full bath access. The 2nd floor offers 2 bedrooms, a full bath and oversized Attic /

    Kirsten Adams William Pitt Sotheby's Int'l

    14 Neptune Ave, Madison, CT 06443
  • 20 Cherry Ln, Madison, CT 06443

    $1,453,000 Sold Aug 29, 2025

    • 2,647 Sq Ft
    • $549/SF
    • 76 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1968

    20 Cherry Ln, Madison, CT 06443

    The best of all worlds awaits in this year-round 5-bedroom, 3-bath home located on a private, quiet road across from the third hole of the Madison Country Club. Walk downtown or stroll to the beach to enjoy sandy shores and breathtaking sunsets. Perfect for entertaining, the layout features a bright living room that opens to the dining area. The galley-style kitchen, thoughtfully designed by

    Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

    20 Cherry Ln, Madison, CT 06443
  • 110 Randi Dr, Madison, CT 06443
    110 Randi Dr, Madison, CT 06443
    110 Randi Dr, Madison, CT 06443
    /40

    $1,485,000

    • 5 Beds
    • 5 Baths
    • 5,779 Sq Ft

    110 Randi Dr, Madison, CT 06443

    A stately circular driveway ushers you into a realm of elegance & comfort. This grand & classic 5,779 sf residence is a testament to luxurious living, offering a harmonious blend of expansive open areas. Step through the front door and be greeted by a formal living room adorned w/ French doors & the first of 3 fireplaces, a space that could effortlessly transition into a distinguished home

    Amy Kirst William Pitt Sotheby's Int'l

    110 Randi Dr, Madison, CT 06443
  • 22 Durham Rd Unit B2, Madison, CT 06443
    22 Durham Rd Unit B2, Madison, CT 06443
    22 Durham Rd Unit B2, Madison, CT 06443
    /18

    $2,250 per month

    • 1 Bed
    • 1.5 Baths
    • 1,005 Sq Ft
    • Townhouse for Rent

    22 Durham Rd Unit B2, Madison, CT 06443

    Newer carpet, shutters and paint! This spectacular in-town luxury townhouse located near Tuxis Pond in the Station Square complex, is just steps from the village of Madison and the Connecticut Commuter Train Station, along with Ring's End and multiple specialty stores. Sited along the scenic marsh with a balcony views and a town maintained path, this 1BR 1.5BA second floor duplex is in like new

    Mary Jane Burt Citi Atlas Real Estate Co LLC

    22 Durham Rd Unit B2, Madison, CT 06443
  • 76 Neck Rd, Madison, CT 06443

    $720,000 Sold Aug 29, 2025

    • 1,459 Sq Ft
    • $493/SF
    • 85 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1824

    76 Neck Rd, Madison, CT 06443

    LOVERS OF ANTIQUE HOUSES REJOICE! The Augustus Peck House c.1824. Beautiful, wide board chestnut floors, multiple fireplaces, exposed beams, a first floor primary bedroom and bath, an updated country kitchen/family room, a charming living room, an office and a large (21' x15') four season sunroom make for easy first floor living. Upstairs are two bedrooms which share a full bath, a small sitting

    Margaret Muir William Pitt Sotheby's Int'l

    76 Neck Rd, Madison, CT 06443
  • 30 Renees Way, Madison, CT 06443
    30 Renees Way, Madison, CT 06443
    30 Renees Way, Madison, CT 06443
    /40

    $898,000

    • 4 Beds
    • 3.5 Baths
    • 4,944 Sq Ft

    30 Renees Way, Madison, CT 06443

    Welcome home to your very own peaceful retreat. Nestled on a classic cul-de-sac in one of the area's most desired neighborhoods. Ideal for multi-generational living, this home features an additional 1100 sf walk out lower level, ready to be utilized as an in-law suite, home gym, recreation space or even an at-home office. The private backyard oasis, features an in-ground pool, hot tub, charming

    Shoreline Homes Team William Raveis Real Estate

    30 Renees Way, Madison, CT 06443
  • 15 Willard Ave, Madison, CT 06443
    15 Willard Ave, Madison, CT 06443
    15 Willard Ave, Madison, CT 06443
    /4

    $3,500 per month

    • 4 Beds
    • 2.5 Baths
    • 2,484 Sq Ft
    • House for Rent

    15 Willard Ave, Madison, CT 06443

    Spend the winter in this charming well maintained colonial in Seaview Association. Enjoy the large eat-in kitchen and the welcoming gathering rooms. The spacious bedrooms provide room for everyone.

    Meig Walz Newcomb Coldwell Banker Realty

    15 Willard Ave, Madison, CT 06443
  • 16 Brantwood Dr, Madison, CT 06443

    $325,000 Sold Aug 29, 2025

    • 1,332 Sq Ft
    • $244/SF
    • 210 Days On Market
    • 2 Beds
    • 3 Baths
    • Built 1986

    16 Brantwood Dr, Madison, CT 06443

    This 2 bedroom/1.2 bath townhouse condo is located in Brantwood, close to I-95 and Madison's lively town center, historic green, beaches, train station, and bus routes. New sidewalks on adjacent streets enhance the convenience of Brantwood. The condo's first floor features an open floor plan living/dining room and eat-in kitchen and slider to the new patio plus a powder room. Upstairs, there are

    Bette Zollshan William Pitt Sotheby's Int'l

    16 Brantwood Dr, Madison, CT 06443
  • 18 Kelsey Springs Dr, Madison, CT 06443
    18 Kelsey Springs Dr, Madison, CT 06443
    18 Kelsey Springs Dr, Madison, CT 06443
    /23

    $789,900 Open Sun 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 2,805 Sq Ft

    18 Kelsey Springs Dr, Madison, CT 06443

    Charming colonial home nestled on 0.96 acres in a desirable neighborhood just minutes from the town beach, shopping, and highway. This beautiful 2800 square foot home boasts an open floor plan perfect for entertaining, with vaulted ceilings and a cozy fireplace. The spacious layout includes four bedrooms, two full baths, and one half bath, partial finished walk out basement and 2 car garage.

    Joanne Fowler Bishop, Edward & Roberts, LLC

    18 Kelsey Springs Dr, Madison, CT 06443
  • 76 High Hill Cir, Madison, CT 06443
    76 High Hill Cir, Madison, CT 06443
    76 High Hill Cir, Madison, CT 06443
    /38

    $9,500 per month

    • 5 Beds
    • 4.5 Baths
    • 5,575 Sq Ft
    • House for Rent

    76 High Hill Cir, Madison, CT 06443

    Perched above a quiet cul-de-sac, in one of Madison's most prestigious communities, this stately five bedroom Colonial is minutes from I-95 and Madison's Town Green and beaches. The home boasts a renovated chef's kitchen with dining area; adjacent to the home's covered deck overlooking an inviting in-ground heated pool. A private office is adjacent to a spacious family room. The second floor

    John Campbell Compass Connecticut, LLC

    76 High Hill Cir, Madison, CT 06443
  • 273 Legend Hill Rd, Madison, CT 06443

    $540,000 Sold Aug 28, 2025

    • 1,598 Sq Ft
    • $338/SF
    • 28 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1985

    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 are 2 rooms in lower level (one room is heated)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
  • 64 Webster Point Rd, Madison, CT 06443
    64 Webster Point Rd, Madison, CT 06443
    64 Webster Point Rd, Madison, CT 06443
    /39

    $2,395,000

    • 4 Beds
    • 3.5 Baths
    • 4,010 Sq Ft

    64 Webster Point Rd, Madison, CT 06443

    GRACIOUS, SPACIOUS AND GRAND Sited one house from Long Island Sound on a quiet cul de sac, 64 Webster Point is a private, classic Colonial with spacious, high ceilinged (10' on the first floor), light filled rooms and beautiful hardwood floors throughout the house. A double height foyer flows into the large living room highlighted by a handsome, wood burning fireplace. Adjacent is the formal

    Margaret Muir William Pitt Sotheby's Int'l

    64 Webster Point Rd, Madison, CT 06443
  • 79 Hartford Ave, Madison, CT 06443
    79 Hartford Ave, Madison, CT 06443
    79 Hartford Ave, Madison, CT 06443
    /26

    $4,800 per month

    • 4 Beds
    • 3 Baths
    • 2,622 Sq Ft
    • House for Rent

    79 Hartford Ave, Madison, CT 06443

    4 Bedroom Renovated Beach House across from Private Beach in Bucolic Madison, Connecticut Available Oct 1- May 31 but flex term. This sunny 4 bedroom/3 bath house with home office and water views is located at the end of a quiet road across from coveted Hartford Avenue beach. The main floor has a large, renovated eat-in-kitchen, spacious living room with gas fireplace, substantial dining area,

    Pamela D'Arc William Pitt Sotheby's Int'l

    79 Hartford Ave, Madison, CT 06443
  • 71 Old Toll Rd, Madison, CT 06443

    $505,000 Sold Aug 28, 2025

    • 2,092 Sq Ft
    • $241/SF
    • 58 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1810

    71 Old Toll Rd, Madison, CT 06443

    1810 Antique ~ lovingly Restored by present owner over the last 7 years. This picturesque home sits on 2.79 Acres and actually owns half of "Shelly Lake". Enjoy the tranquil water views from the newly Glassed in heated rear porch. Or if you prefer, grab a book and pull up a chair to any one of the 4 Wood Burning Fireplaces. Main Kitchen has been remodeled with Granite, Stainless Steel and a

    Tom Clancy William Pitt Sotheby's Int'l

    71 Old Toll Rd, Madison, CT 06443
  • 513 Boston Post Rd, Madison, CT 06443
    513 Boston Post Rd, Madison, CT 06443
    513 Boston Post Rd, Madison, CT 06443
    /28

    $1,300,000

    • 4 Beds
    • 2.5 Baths
    • 3,031 Sq Ft

    513 Boston Post Rd, Madison, CT 06443

    Nestled in the heart of Madison Village, this exquisite Greek Revival-style home offers unparalleled privacy. Tucked behind a grove of trees this is a rare find in downtown Madison. Just a short stroll to the Green, downtown shops, golf course and the beaches, this impeccably maintained antique home blends classic charm with modern convenience. Inside, you'll find an open kitchen that flows into

    Meig Walz Newcomb Coldwell Banker Realty

    513 Boston Post Rd, Madison, CT 06443
  • 49 Cottage Rd Unit 20, Madison, CT 06443
    49 Cottage Rd Unit 20, Madison, CT 06443
    49 Cottage Rd Unit 20, Madison, CT 06443
    /14

    $2,000 per month

    • 1 Bed
    • 1 Bath
    • 512 Sq Ft
    • House for Rent

    49 Cottage Rd Unit 20, Madison, CT 06443

    Charming 1-Bedroom Fully Furnished Apartment in Madison, CT - Walk to the Beach & Restaurants! This bright and beautifully maintained 1-bedroom, 1-bathroom fully furnished apartment is perfectly located in the heart of Madison, CT-just 1 mile from Hammonasset Beach and walking distance to local favorites. Enjoy a comfortable living space with hardwood floors throughout and a sunny dining area. A

    Abbey Nakano Houlihan Lawrence WD

    49 Cottage Rd Unit 20, Madison, CT 06443
  • 31 Meadowbrook Rd, Madison, CT 06443

    $1,005,000 Sold Aug 28, 2025

    • 3,360 Sq Ft
    • $299/SF
    • 4 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1986

    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
  • 146 Chittenden Field Ln, Madison, CT 06443
    146 Chittenden Field Ln, Madison, CT 06443
    146 Chittenden Field Ln, Madison, CT 06443
    /33

    $1,950,000

    • 3 Beds
    • 2 Baths
    • 1,824 Sq Ft

    146 Chittenden Field Ln, Madison, CT 06443

    Just Steps from the Sand - Your Coastal Retreat Awaits! Wake up in your 3-bedroom beach house to the sound of waves rolling onto your private beach. Bright, open living spaces bring the ocean right inside, while each room offers serene, million-dollar views and the soothing rhythm of the sea. This is more than home - it's your slice of paradise. Enjoy panoramic ocean views from every room, walls

    Lori Bartone William Raveis Real Estate

    146 Chittenden Field Ln, Madison, CT 06443
  • 3 Apple Way, Madison, CT 06443
    3 Apple Way, Madison, CT 06443
    3 Apple Way, Madison, CT 06443
    /31

    $3,850 per month

    • 3 Beds
    • 2.5 Baths
    • 1,414 Sq Ft
    • House for Rent

    3 Apple Way, Madison, CT 06443

    Yearly Lease! 3 Apple Way is ready to be leased!! You can't beat the location-just minutes to downtown Madison, the beaches, and I-95 for a quick and easy commute. Inside, this charming and well-kept home is perfect for professionals, families, or anyone looking to enjoy the shoreline lifestyle. This unique opportunity offers flexibility-it can come tastefully furnished or completely empty to

    Paige Slocum William Raveis Real Estate

    3 Apple Way, Madison, CT 06443
  • 42 Lake Dr, Madison, CT 06443

    $454,000 Sold Aug 28, 2025

    • 2,036 Sq Ft
    • $223/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1973

    42 Lake Dr, Madison, CT 06443

    Charming 4-Bedroom Colonial in Serene Neighborhood Setting Step into timeless colonial charm with this spacious 4-bedroom, 2.5-bath home, nestled in a peaceful neighborhood surrounded by nature. Inside, you'll find wide plank hardwood floors in the living room, complemented by a cozy fireplace-perfect for relaxing evenings. The main level offers the convenience of a laundry room and a layout

    Roberta Whalen LAER Realty Partners

    42 Lake Dr, Madison, CT 06443
  • 125 Wildcat Rd, Madison, CT 06443
    125 Wildcat Rd, Madison, CT 06443
    125 Wildcat Rd, Madison, CT 06443
    /26

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 3,909 Sq Ft

    125 Wildcat Rd, Madison, CT 06443

    Nestled just minutes from the heart of downtown Madison, this exceptional property offers the perfect blend of convenience, privacy, and year-round beauty. Loved by the same family for 34 years, at the end of a long circular driveway you will find this home that sits on a professionally landscaped lot that blooms with color in every season, attracting songbirds from spring through fall. Inside,

    Meig Walz Newcomb Coldwell Banker Realty

    125 Wildcat Rd, Madison, CT 06443
  • 66 Oak Ave, Madison, CT 06443
    66 Oak Ave, Madison, CT 06443
    66 Oak Ave, Madison, CT 06443
    /19

    $3,250 per month

    • 3 Beds
    • 1.5 Baths
    • 1,296 Sq Ft
    • House for Rent

    66 Oak Ave, Madison, CT 06443

    Academic Rental September-June. Classic Farm house colonial sits directly on the waterfront! The home embodies peace and tranquility with a nod to simpler times when nature was the forefront of relaxation. Enjoy your private beach and yard and take in those glorious sunsets that Madison is known for. Enjoy a classic floor plan with a galley style kitchen, dining room, living room and a sunny

    Mary Edeen Berkshire Hathaway NE Prop.

    66 Oak Ave, Madison, CT 06443
  • 23 Paper Mill Dr, Madison, CT 06443

    $725,000 Sold Aug 25, 2025

    • 2,323 Sq Ft
    • $312/SF
    • 61 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1979

    23 Paper Mill Dr, Madison, CT 06443

    Welcome to 23 Paper Mill Drive - a timeless Colonial nestled in a quiet cul-de-sac neighborhood. This lovely 5-bedroom, 2.5-bath home offers 2,323 square feet of comfortable living space, plus a full unfinished walk-out basement with endless potential. Step inside to discover beautiful hardwood floors, a remodeled kitchen, all new windows, and classic touches throughout. The main level features a

    Dana Weinstein Coldwell Banker Realty

    23 Paper Mill Dr, Madison, CT 06443

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