8,614

Madison, CT Homes

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  • 181 Ridge Rd, Madison, CT 06443

    $625,000 Sold Sep 17, 2025

    • 1,921 Sq Ft
    • $325/SF
    • 32 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1973

    181 Ridge Rd, Madison, CT 06443

    Welcome to this beautifully renovated Mid-Century split-level home, thoughtfully updated to offer modern comfort and style throughout. The open-concept layout features gleaming hardwood floors, a granite kitchen with newer SS appliances, and fully remodeled bathrooms. A spacious three-season porch off the dining area provides a versatile bonus space-currently used as a home gym and playroom, can

    Renee Autorino Coldwell Banker Realty

    181 Ridge Rd, Madison, CT 06443
  • 132 Summer Hill Rd, Madison, CT 06443
    132 Summer Hill Rd, Madison, CT 06443
    132 Summer Hill Rd, Madison, CT 06443
    /40

    $2,375,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,637 Sq Ft

    132 Summer Hill Rd, Madison, CT 06443

    Welcome to your dream home, where thoughtful design meets high-end craftsmanship. This newly built four-bedroom, four-and-a-half bathroom house offers the perfect blend of style and comfort. Inside, an open floor plan creates a seamless flow from room to room, anchored by a soaring two-story great room with a stunning gas fireplace. Large oversized doors spill out onto a 580 SF covered deck where

    Diane Dupont William Pitt Sotheby's Int'l

    132 Summer Hill Rd, Madison, CT 06443
  • 35 Bishop Ln, Madison, CT 06443

    $835,000 Sold Sep 15, 2025

    • 2,568 Sq Ft
    • $325/SF
    • 19 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2002

    35 Bishop Ln, Madison, CT 06443

    Welcome to 35 Bishop Ln, Madison-a beautifully remodeled haven that embodies elegance & comfort. Its proximity to town (only 1.7 miles), Madison Beaches (including Hammonasset State Pk only 2.8 miles away) & the local swim & racquet club adds to the appeal, making this property the ultimate retreat. This stunning home offers 2,568sf of refined living space, w/an additional 852sf in the finished

    Lisa Rollins Team Compass Connecticut, LLC

    35 Bishop Ln, Madison, CT 06443
  • 6 Young's Village, Madison, CT 06443
    6 Young's Village, Madison, CT 06443
    6 Young's Village, Madison, CT 06443
    /11

    $259,900 New Construction

    • 2 Beds
    • 1 Bath
    • 612 Sq Ft

    6 Young's Village, Madison, CT 06443

    Brand New Cottage : ) This seasonal cottage located on First Street # 6 in Young's Village next to Hammonasett State Beach Park. Enjoy swimming, coastal walk ways and fabulous restaurants .- all within a hop, skip and jump away! This new cottage offers two bedrooms, walk in closets, a laundry hookup space, and electric fireplace. The kitchen showcases granite countertops, tile floors, stainless

    Jason Saphire www.HomeZu.com

    6 Young's Village, Madison, CT 06443
  • 37 Riverside Terrace, Madison, CT 06443

    $580,000 Sold Sep 15, 2025

    • 1,955 Sq Ft
    • $297/SF
    • 16 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1964

    37 Riverside Terrace, Madison, CT 06443

    This cozy 3-bedroom, 2.5-bath raised ranch sits on a generous lot in a highly sought-after neighborhood, just minutes from schools, I-95, Route One, town conveniences, and the shoreline. A newly installed stone step entrance adds curb appeal and a welcoming touch as you approach the home. The main level welcomes you with a bright and airy atmosphere, enhanced by hardwood floors throughout. A

    Erin Connelly Coldwell Banker Realty

    37 Riverside Terrace, Madison, CT 06443
  • 454 Horse Pond Rd Unit B, Madison, CT 06443
    454 Horse Pond Rd Unit B, Madison, CT 06443
    454 Horse Pond Rd Unit B, Madison, CT 06443
    /9

    $1,375,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 4,357 Sq Ft

    454 Horse Pond Rd Unit B, Madison, CT 06443

    2025 is the year to have the home of your dreams! Come see this gorgeous enclave of five to-be-built houses on a private road in the charming coastal town of Madison. Ideally located just two hours from both NYC and Boston, Madison is beloved for its award-winning schools, restaurants, shops, and of course, beautiful beaches! Constructed by a well-established local Madison builder, these houses

    Karen Rosenthal William Raveis Real Estate

    454 Horse Pond Rd Unit B, Madison, CT 06443
  • 123 Legend Hill Rd Unit 123, Madison, CT 06443

    $455,000 Sold Sep 12, 2025

    • 1,280 Sq Ft
    • $355/SF
    • 128 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1984

    123 Legend Hill Rd Unit 123, Madison, CT 06443

    Welcome to Legend Hill, where the sunsets from this 2-bedroom 2.5 bath condominium are unsurpassed! You will be in the town of Madison with its private beaches, quaint boutiques, and summer farmers markets on the town green. What a great place to call home! This recently renovated condo has crown molding, engineered hardwood floors, and a gas fireplace, adding warmth and ambiance on those chilly

    Scott Penna William Raveis Real Estate

    123 Legend Hill Rd Unit 123, Madison, CT 06443
  • 454 Horse Pond Rd Unit C, Madison, CT 06443
    454 Horse Pond Rd Unit C, Madison, CT 06443
    454 Horse Pond Rd Unit C, Madison, CT 06443
    /9

    $1,350,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,568 Sq Ft

    454 Horse Pond Rd Unit C, Madison, CT 06443

    2025 is the year to have the home of your dreams! Come see this gorgeous enclave of five to-be-built houses on a private road in the charming coastal town of Madison. Ideally located just two hours from both NYC and Boston, Madison is beloved for its award-winning schools, restaurants, shops, and of course, beautiful beaches! Constructed by a well-established local Madison builder, these houses

    Karen Rosenthal William Raveis Real Estate

    454 Horse Pond Rd Unit C, Madison, CT 06443
  • 45 Kaiser Ln, Madison, CT 06443

    $1,425,000 Sold Sep 12, 2025

    • 4,232 Sq Ft
    • $337/SF
    • 94 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2024

    45 Kaiser Ln, Madison, CT 06443

    Stunning to-be-built home in Madison located at the end of a lovely cul-de-sac in the sought after Century Oak community! Have it all with this new construction situated on a beautiful and peaceful lot that borders open space and is only 5 minutes to the heart of downtown Madison, including beaches, shopping, and the train station. Gorgeous kitchen with breakfast bar leads into living room with

    Karen Rosenthal William Raveis Real Estate

    45 Kaiser Ln, Madison, CT 06443
  • 318 Horse Pond Rd, Madison, CT 06443
    318 Horse Pond Rd, Madison, CT 06443
    318 Horse Pond Rd, Madison, CT 06443
    /38

    $725,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,622 Sq Ft

    318 Horse Pond Rd, Madison, CT 06443

    Set on a private lot just minutes from town, top-rated schools, recreational facilities and beautiful beaches, this elegant 4-bedroom Colonial offers both charm and convenience. The spacious first floor features a beautifully updated kitchen with white cabinetry, granite countertops, and a pretty backsplash. The Gedney kitchen flows seamlessly into a warm and inviting family room - perfect for

    Carol Farmer William Raveis Real Estate

    318 Horse Pond Rd, Madison, CT 06443
  • 28 1st St, Madison, CT 06443

    $187,000 Sold Sep 12, 2025

    • 470 Sq Ft
    • $398/SF
    • 110 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1950

    28 1st St, Madison, CT 06443

    Delightful seasonal(4/1-10/31)storybook cottage located in a vintage beach community nestled on leased land located in the picturesque coastal town of Madison Ct. This unique village is on 6 acres situated adjacent to the sandy stretch of Long Island Sounds Hammonassett State Park, Salt Meadow Park (includes dog park) & the Greenway trail. You will be greeted by a freshly painted (exterior)home

    Karen Bruno Roos Williams Real Estate

    28 1st St, Madison, CT 06443
  • 20 Strawberry Hill Rd, Madison, CT 06443
    20 Strawberry Hill Rd, Madison, CT 06443
    20 Strawberry Hill Rd, Madison, CT 06443
    /18

    $549,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,138 Sq Ft

    20 Strawberry Hill Rd, Madison, CT 06443

    This original owner, 1960's built, 3 bedroom, 2 bath single family residence is nestled in an established, sought-after area and offers unlimited possibilities. Whether you are a first-time homebuyer, investor or renovation enthusiast, this property is your chance to customize a home that reflects your vision and style in a location that truly delivers. Bring your vision and unlock the

    Pam Kadamus William Pitt Sotheby's Int'l

    20 Strawberry Hill Rd, Madison, CT 06443
  • 48 East St, Madison, CT 06443

    $182,000 Sold Sep 08, 2025

    • 480 Sq Ft
    • $379/SF
    • 26 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1961

    48 East St, Madison, CT 06443

    Situated in the Coastal Charm of Madison, this Seasonal Cottage is your Escape you can plan on Every Summer !! Enjoy all that Madison has to offer w/ Concert's on the Green, Farmers Markets, Restaurants and Beaches. It's a Long Summer too ~ Residence can stay from April 1st all the way through October 31st., a Full 7-Months. Home is perfectly set at the End of East Street (minimal traffic) on an

    Tom Clancy William Pitt Sotheby's Int'l

    48 East St, Madison, CT 06443
  • 33 Seaview Ave, Madison, CT 06443
    33 Seaview Ave, Madison, CT 06443
    33 Seaview Ave, Madison, CT 06443
    /40

    $4,500,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 4,613 Sq Ft

    33 Seaview Ave, Madison, CT 06443

    Stunning one-of-a-kind residence designed by Robert Page, AIA. Set directly on coveted private assoc. Seaview Beach, this iconic 4-level 4,600+ sq. ft. coastal retreat offers an unparalleled blend of modern sensibility and timeless craftmanship. Largely renovated in 2023, no detail was overlooked in this luxurious sanctuary for those who want the exceptional in coastal living. No flood insurance

    Margaret Muir William Pitt Sotheby's Int'l

    33 Seaview Ave, Madison, CT 06443
  • 108 Sandlewood Dr, Madison, CT 06443

    $475,000 Sold Sep 05, 2025

    • 2,640 Sq Ft
    • $180/SF
    • 72 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1968

    108 Sandlewood Dr, Madison, CT 06443

    Welcome to easy living with this delightful one-story home in Madison, CT. Located 2.5 miles from the scenic Madison Surf Club! This oversized ranch offers a seamless blend of comfort and potential. Picture yourself unwinding by the fireplace in the cozy living room or enjoying the versatility of the expansive den with plenty of room for flex space or entertaining. This home offers three

    Jennifer Bordonaro William Pitt Sotheby's Int'l

    108 Sandlewood Dr, 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 Pending

    • 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
  • 24 Deepwood Dr, Madison, CT 06443

    $475,000 Sold Sep 03, 2025

    • 1,200 Sq Ft
    • $396/SF
    • 27 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1962

    24 Deepwood Dr, Madison, CT 06443

    Great Opportunity To Live In Madison for a reasonable price. This three level split home on a level, treed lot in established neighborhood is ready to be your next home. Hardwood throughout living room and all 3 bedrooms. Enjoy the oversized 3 season screen porch this Fall and cozy up in front of the raised hearth fireplace this Winter. Just under one full acre, this home is private and set on a

    Carol Mancini William Pitt Sotheby's Int'l

    24 Deepwood Dr, Madison, CT 06443
  • 28 Aylesbury Cir Unit 28, Madison, CT 06443
    28 Aylesbury Cir Unit 28, Madison, CT 06443
    28 Aylesbury Cir Unit 28, Madison, CT 06443
    /3

    $650,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,476 Sq Ft

    28 Aylesbury Cir Unit 28, Madison, CT 06443

    Large ranch unit with views of the Hammonassett River from several rooms and the brick-walled patio. Full basement, partially finished with huge amount of storage. Open floor plan living room and dining area, leading to the family room with gas fireplace & built-ins. Family room has sliders to 3 season porch with supplemental electric heat, which leads to a lovely brick walled patio overlooking

    Alison Gould Gould Group LLC

    28 Aylesbury Cir Unit 28, Madison, CT 06443
  • 299 Warpas Rd, Madison, CT 06443

    $1,610,000 Sold Sep 03, 2025

    • 4,762 Sq Ft
    • $338/SF
    • 5 Days On Market
    • 4 Beds
    • 7 Baths
    • Built 2008

    299 Warpas Rd, Madison, CT 06443

    Nestled on a private 3.3-acre estate, this meticulously maintained residence offers unparalleled luxury and comfort. Originally constructed in 2008 and completed in 2009, this 4-bedroom, 5-bathroom home has been thoughtfully updated to meet the highest standards. The spacious bedrooms each feature en-suite bathrooms, providing ultimate privacy and convenience. The fully finished lower level

    Cathy Lynch Coldwell Banker Realty

    299 Warpas Rd, Madison, CT 06443
  • 129 Acorn Rd, Madison, CT 06443
    129 Acorn Rd, Madison, CT 06443
    129 Acorn Rd, Madison, CT 06443
    /33

    $739,900 Pending

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

    129 Acorn Rd, Madison, CT 06443

    A stone's throw away from the heart of Madison Village, perfectly positioned at 1.4 miles from the bustling center, with beaches, recreational fields, and the renowned Bookstore. Shopping, dining, and are all conveniently close, making this an ideal location for those seeking both tranquility and community amenities. Occupying a generous .74-acre level lot, the low-maintenance garden and an

    Ann Stewart William Pitt Sotheby's Int'l

    129 Acorn Rd, 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
  • 37 Pine Dr, Madison, CT 06443
    37 Pine Dr, Madison, CT 06443
    37 Pine Dr, Madison, CT 06443
    /37

    $695,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,390 Sq Ft

    37 Pine Dr, Madison, CT 06443

    Never before offered to the public. A Local respected builder's own home blends contemporary mid century elements reminiscent of Franklin Lloyd Wright's "organic" design. Wooden interior textures, expansive windows invite the exterior landscape offering a place of solitude and refuge. Warm wood tones and naturalistic design of the vaulted wood ceilings, floor to ceiling fireplaces envelop you;

    Heather Clinton Berkshire Hathaway NE Prop.

    37 Pine 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
  • 29 Circle Beach Rd, Madison, CT 06443
    29 Circle Beach Rd, Madison, CT 06443
    29 Circle Beach Rd, Madison, CT 06443
    /32

    $699,000 Pending

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft

    29 Circle Beach Rd, Madison, CT 06443

    A little piece of paradise awaits you in this direct, waterfront cottage. Perfectly situated with unobstructed views of Long Island Sound. Shoreline living at its best in this beautiful beach community! So much potential and options to make this 2-bedroom gem your own. Re-model to your taste or utilize the walk-up attic, to build up, for additional living space. Enjoy your private beach or the

    Gary Piccirillo RE/MAX Right Choice

    29 Circle Beach Rd, 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
  • 462 Horse Pond Rd, Madison, CT 06443
    462 Horse Pond Rd, Madison, CT 06443
    462 Horse Pond Rd, Madison, CT 06443
    /12

    $1,375,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 4,357 Sq Ft

    462 Horse Pond Rd, Madison, CT 06443

    2025 is the year to have the home of your dreams! Come see this gorgeous enclave of five to-be-built houses on a private road in the charming coastal town of Madison. Ideally located just two hours from both NYC and Boston, Madison is beloved for its award-winning schools, restaurants, shops, and of course, beautiful beaches! Constructed by a well-established local Madison builder, these houses

    Karen Rosenthal William Raveis Real Estate

    462 Horse Pond Rd, 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

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