Madison, CT Homes

• 

  $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
• 

  Est $729,937 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,484 Sq Ft

  64 Saint Francis Woods Rd, Madison, CT 06443

  64 Saint Francis Woods Rd, Madison, CT 06443
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  /27

  $154,900 Under Contract

  • 1 Bed
  • 1 Bath
  • 410 Sq Ft

  20 Young's Village, Madison, CT 06443

  Madison CT - $154,900 - THE ABSOLUTE BEST SEASHORE HOME VALUE! Located in desirable Young's Village Madison CT. Seasonal beach house ideal for 1 - 4 persons. Rebuilt in 2003! Turnkey, available furnished! Rare offering is less than a mile walk to toes in the water at Hammonasset Beach St Park, and the sandy shores and glimmering salt waters of Long Island Sound. Walk, bike, car ride to

  Laurie McCann William Pitt Sotheby's Int'l

  20 Young's Village, 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
• 

  Est $719,432 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,121 Sq Ft

  19 Saint Francis Woods Rd, Madison, CT 06443

  19 Saint Francis Woods Rd, Madison, CT 06443
• 

  

  /6

  $249,000 Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  2175 Durham Rd, Madison, CT 06443

  HIGHEST & BEST OFFERS DUE BY 3PM AUGUST 5TH. Opportunity Knocks! The 3-bedroom ranch situated on just under 1 acre offers the perfect chance to create your own vision. With some TLC, this single-level home can be transformed into a cozy and comfortable retreat tailored to your style. Whether you're a first-time buyer or looking to downsize, this property provides a solid foundation in a peaceful

  Nicholas Mastrangelo Coldwell Banker Realty

  2175 Durham 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
• 

  Est $697,670 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,229 Sq Ft

  11 Saint Francis Woods Rd, Madison, CT 06443

  11 Saint Francis Woods Rd, Madison, CT 06443
• 

  

  /36

  $849,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 3,464 Sq Ft

  241 Hunters Trail, Madison, CT 06443

  Tucked away in one of Madison's most desirable subdivisions, this spacious 4-bedroom, 3.5-bath colonial offers the perfect blend of function, flow, and comfort-just minutes to downtown, beaches, the highway, and medical facilities. The heart of the home is the warm and inviting kitchen, complete with rich cherry cabinets, an oversized island, ample storage, and generous counter space-designed for

  Heidi DeRusso Coldwell Banker Realty

  241 Hunters Trail, 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
• 

  Est $692,841 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  53 Country Way, Madison, CT 06443

  53 Country Way, Madison, CT 06443
• 

  

  /40

  $1,325,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,569 Sq Ft

  31 Stanton Ct, Madison, CT 06443

  Highest and Best Offers are due by Sunday, July 27th at 8 pm. Nestled at the end of a quiet cul-de-sac just a short stroll from Madison's sandy Pent Road Beach, this stately Colonial offers the perfect blend of timeless elegance and modern updates. With 4-5 bedrooms and 3 full baths, the home opens to an impressive foyer with a sweeping curved staircase. The spacious living room, with the first

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  31 Stanton Ct, 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
• 

  Est $1,040,253 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,835 Sq Ft

  106 Summer Hill Rd, Madison, CT 06443

  106 Summer Hill Rd, Madison, CT 06443
• 

  

  /40

  $2,799,000 Under Contract

  • 5 Beds
  • 4 Baths
  • 3,397 Sq Ft

  25 Seaview Ave, Madison, CT 06443

  Unique, custom, architecturally designed home in the desirable Seaview Beach area. Situated on a high point of Seaview Ave on a corner lot, with deeded access rights to Long Island Sound. The sandy beach is accessed by a dedicated waterway with cabana. Perfect for a second or summer home, as well as a primary residence. This home was entirely rebuilt in 2010 and boasts numerous amenities &

  Alison Gould Gould Group LLC

  25 Seaview Ave, 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
• 

  Est $848,316 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,974 Sq Ft

  133 Overbrook Rd, Madison, CT 06443

  133 Overbrook Rd, Madison, CT 06443
• 

  

  /38

  $525,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,159 Sq Ft

  9 Madrina Ln, Madison, CT 06443

  Tucked away at the end of a quiet cul-de-sac, this 3-bedroom, 2-bath contemporary style home sits on a private .6-acre lot in a desirable location; just minutes from beaches, Hammonasset State Park, the scenic Shoreline walking trails, and the vibrant center of town. Steps lead up to the front deck and entry foyer, opening to a light-filled, open-concept living space. Cathedral ceilings with

  Rose Ciardiello William Raveis Real Estate

  9 Madrina Ln, 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
• 

  Est $640,699 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  924 Durham Rd, Madison, CT 06443

  924 Durham Rd, Madison, CT 06443
• 

  

  /26

  $725,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,116 Sq Ft

  57 Circle Beach Rd, Madison, CT 06443

  Nestled along the shores of Long Island Sound, this classic 3-bedroom, 1.5-bath, this 1116 sq.ft cottage offers a rare opportunity to own a true waterfront retreat with panoramic views-including Faulkner's Island-and a separate deep water dock on the Neck River just across the street. From the moment you step inside, you're welcomed by sweeping, unobstructed water views and endless potential.

  Cheryl Kebalo ENRG Global Realty, LLC

  57 Circle Beach 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
• 

  Est $654,257 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,186 Sq Ft

  62 Bartlett Dr, Madison, CT 06443

  62 Bartlett Dr, Madison, CT 06443
• 

  

  /31

  $475,000 Under Contract

  • 1 Bed
  • 2.5 Baths
  • 1,569 Sq Ft

  22 Centre Village Dr, Madison, CT 06443

  Welcome to 22 Centre Village Drive, Madison! From the moment you step inside, you'll be captivated by the light-filled, open-concept layout featuring soaring ceilings, oversized windows, and nine skylights with remote-controlled blinds. The spacious living room, centered around a cozy gas fireplace, seamlessly connects to a formal dining area and a dramatic two-story, three-season sunroom-perfect

  Emily Lovejoy William Raveis Real Estate

  22 Centre Village Dr, 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
• 

  Est $1,190,975 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 4,966 Sq Ft

  39 Silo Hill, Madison, CT 06443

  39 Silo Hill, Madison, CT 06443
• 

  

  /33

  $769,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  11 Pent Rd, Madison, CT 06443

  LOCATION!!! One of Madison's most desirable beach neighborhoods awaits you. This charming beach community home has it's own separate cottage! Walk to the beautiful beach or the popular "Greenway Trail" that leads into Hammonasset State Park. Enjoy swimming, paddle boarding, kayaking or just relaxing in the warm Summer sun. The main house boasts a first floor full bath, kitchen, dining area,

  Maggie Bartels Coldwell Banker Realty

  11 Pent Rd, 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
• 

  Est $607,061 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  22 Aileen Dr, Madison, CT 06443

  22 Aileen Dr, Madison, CT 06443
• 

  

  /9

  $1,275,000 Under Contract

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

  454 Horse Pond Rd Unit A, 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 A, 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
• 

  Est $587,120 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,440 Sq Ft

  19 Aileen Dr, Madison, CT 06443

  19 Aileen Dr, Madison, CT 06443
• 

  

  /8

  $213,000 Under Contract

  • Land
  • 2.87 Acres
  • $74,216 per Acre

  983 Boston Post Rd, Madison, CT 06443

  983 Boston Post Road, Madison, CT - Walk to Downtown Madison Center. This is a rare opportunity to build the home of your dreams in Madison - one of the most picturesque communities on the Eastern Connecticut Shoreline! Perfect proximity to town, beaches and schools. Madison is acclaimed for having a top ranked school system. A-2 Survey Map with proposed home and septic location on 2.87ac parcel.

  Jennifer Gurnell William Raveis Real Estate

  983 Boston Post Rd, Madison, CT 06443
• 

  $505,000 Sold May 08, 2025

  • 1,498 Sq Ft
  • $337/SF
  • 9 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1985

  18 Centre Village Dr Unit 18, Madison, CT 06443

  Discover the allure of Centre Village with this sun filled two-bedroom, 2.1-bath end unit, nestled towards the rear for ultimate privacy. Bask in the abundance of natural sunlight that fills each room, complemented by hardwood floors throughout. The living room, a cozy haven, features a charming fireplace and French doors that lead to an expansive deck, perfect for serene outdoor living.

  Sue Knapp William Pitt Sotheby's Int'l

  18 Centre Village Dr Unit 18, Madison, CT 06443
• 

  Est $658,248 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,026 Sq Ft

  62 Granby Dr, Madison, CT 06443

  62 Granby Dr, Madison, CT 06443
• 

  $1,010,000 Sold May 05, 2025

  • 3,123 Sq Ft
  • $323/SF
  • 39 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1991

  100 Quail Run, Madison, CT 06443

  Welcome home to this classic 4-bedroom, 2.5-bath colonial located in the sought-after Neck River Farms neighborhood. The open floor plan includes a fantastic, remodeled kitchen with high-end cabinetry, a center island, double ovens, and granite countertops. The sunny breakfast area leads directly to the inviting family room with a vaulted ceiling and cozy fireplace. While the formal living and

  Cathy Lynch Coldwell Banker Realty

  100 Quail Run, Madison, CT 06443
• 

  Est $730,552 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,532 Sq Ft

  40 Overbrook Rd, Madison, CT 06443

  40 Overbrook Rd, Madison, CT 06443
• 

  $876,000 Sold May 02, 2025

  • 3,137 Sq Ft
  • $279/SF
  • 39 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1995

  46 Kelsey Springs Dr, Madison, CT 06443

  Multiple Offers-Highest/Best due by Monday (3/24) 8pm. Situated in a desirable subdivision close to town, beaches, shopping, and schools, this beautifully maintained center hall Colonial blends timeless charm with modern convenience. The main floor welcomes you with a formal dining room and living room that frame the foyer, creating a sophisticated yet warm ambiance. The eat-in kitchen, complete

  Linda Toscano Coldwell Banker Realty

  46 Kelsey Springs Dr, Madison, CT 06443
• 

  Est $648,568 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,253 Sq Ft

  37 Overbrook Rd, Madison, CT 06443

  37 Overbrook Rd, Madison, CT 06443
• 

  $1,010,000 Sold May 02, 2025

  • 3,787 Sq Ft
  • $267/SF
  • 56 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2008

  62 Lenore Dr, Madison, CT 06443

  Welcome to 62 Lenore Drive, located at the end of a quiet cul-de-sac in one of Madison's most desirable neighborhoods. Offering over 3,700 sq. ft of space, this home is perfect for those looking for room to grow and entertain. Upon entry, you're greeted by formal living and dining rooms, ideal for hosting gatherings. The heart of the home includes a spacious kitchen with high end appliances and

  Phoebe Finch William Pitt Sotheby's Int'l

  62 Lenore Dr, Madison, CT 06443

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