Madison, CT Homes

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  /40

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 3,711 Sq Ft

  1543 Durham Rd, Madison, CT 06443

  Bring your imagination! This spacious home offers 3 bedrooms and 2.5 bathrooms, ready for your vision and updates. Featuring classic architectural details, generous room sizes, and a functional floor plan, this property has great bones and endless potential. The main level includes a large living room, formal dining area, and a kitchen ready for redesign. Upstairs, you'll find three comfortable

  

  Rob McConville

  William Pitt Sotheby's Int'l

  (475) 290-6326

  1543 Durham Rd, Madison, CT 06443
• Explore Madison

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  /2

  $22,000 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,511 Sq Ft
  • House for Rent

  72 Cherry Ln, Madison, CT 06443

  Relax and enjoy this summer in a beautiful property situated just 200 yards from West Wharf Beach and 3/10th of a mile from Surf Club Beach. This newly renovated 2500 Sqft house is surrounded by golfing fairways of Madison Country Club and is located on a private lane. The property boasts a fully remodeled and newly decorated family room, dining room, large eat-in kitchen, four bright bedrooms, 2

  

  Bob Yostos

  Coldwell Banker Realty

  (203) 872-5334

  72 Cherry Ln, Madison, CT 06443
• 

  $799,000 Sold Nov 25, 2025

  • 1,382 Sq Ft
  • $578/SF
  • 11 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1850

  52 Copse Rd, Madison, CT 06443

  LOCATION, LOCATION, LOCATION. PRIME MADISON LOCATION IN A NEIGHBORHOOD SETTING WALKING DISTANCE TO TOWN GREEN AND DOWNTOWN. RARE OPPORTUNITY TO OWN THIS PROPERTY ON OVER AN ACRE WITH TWO OUTBUILDING/BARNS ON PROPERTY. WHETHER YOU ARE LOOKING TO REHAB, ADD-ON OR USE AS A BUILDING LOT, THIS PROPERTY OFFERS MULTIPLE USE OPPORTUNITIES. PRESENT OWNER HAS STARTED THE PROCESS AND HAS INVESTED OVER $55K

  Laureen Kennedy Coldwell Banker Realty

  52 Copse Rd, Madison, CT 06443
• 

  Est $903,671 Not Listed For Sale

  2 Grove Ave, Madison, CT 06443

  2 Grove Ave, Madison, CT 06443
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  /40

  $3,000,000

  • 6 Beds
  • 4.5 Baths
  • 6,300 Sq Ft

  37 Lantern Hill Rd, Madison, CT 06443

  Welcome to 37 Lantern Hill Road, a luxurious residence nestled in the heart of Madison's most coveted neighborhood. Just a short stroll from pristine beaches, the charming town center, and the Madison Country Club, this home offers an unparalleled lifestyle of comfort and convenience. Tucked away along picturesque brick-lined sidewalks and illuminated by classic lanterns, this exceptional

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 283-9847

  37 Lantern Hill Rd, Madison, CT 06443
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  /19

  $3,200 per month plus fees

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  69 Garnet Park Rd, Madison, CT 06443

  Property Id: 1428140This is a lovely and well maintained home on a beautiful quiet street which sits across from the water; that has some of the most stunning sunsets. The interior of the home has been styled with an all white canvas with a updated and modern kitchen. The larger bedroom can very easily handle a king bed with a beautiful view of the backyard grounds. Home is on 1 acre.

  69 Garnet Park Rd, Madison, CT 06443
• 

  $620,000 Sold Nov 25, 2025

  • 1,992 Sq Ft
  • $311/SF
  • 32 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1980

  60 Winterhill Rd, Madison, CT 06443

  Welcome to this classic 4-bedroom, 2.1-bath Colonial in Madison, offering a wonderful combination of comfort and potential. Inside, you'll find hardwood floors throughout and a warm, inviting Family Room with a propane fireplace-perfect for cozy evenings at home. The Kitchen and main bath are ready for your personal touches, while the Primary Suite features a beautifully renovated bathroom with a

  Kelly Whiteman William Raveis Real Estate

  60 Winterhill Rd, Madison, CT 06443
• 

  Est $200,339 Not Listed For Sale

  2117 Durham Rd, Madison, CT 06443

  2117 Durham Rd, Madison, CT 06443
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  /23

  $539,000

  • 2 Beds
  • 2.5 Baths
  • 1,879 Sq Ft

  45 Wilshire Rd Unit 45, Madison, CT 06443

  Wonderful Townhouse in Kensington South! Ideally located near Madison's town center, beaches, library, and fantastic restaurants, this two-bedroom townhouse offers easy, comfortable living. The spacious living room leads to an eat-in kitchen that opens to a cozy family room with a fireplace and sliders to a private patio-perfect for relaxing or entertaining. The first floor also features a half

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 769-9945

  45 Wilshire Rd Unit 45, Madison, CT 06443
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  /33

  $3,500 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,286 Sq Ft
  • House for Rent

  43 Neck Rd, Madison, CT 06443

  Located in the heart of one of Madison's premier beach communities, 43 Neck Road is a darling and meticulously maintained academic or annual rental available as of November 15, 2025. Enjoy this charming home for the Winter and Spring or hang your hat thru the Summer into the Fall. Never before available for this extended timeframe, this sweet house is a catch! You'll appreciate the classic floor

  Phoebe Finch William Pitt Sotheby's Int'l

  43 Neck Rd, Madison, CT 06443
• 

  $1,400,000 Sold Nov 25, 2025

  • 5,779 Sq Ft
  • $242/SF
  • 57 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1988

  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
• 

  Not Listed For Sale

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

  24 Wilshire Rd Unit 24A, Madison, CT 06443

  24 Wilshire Rd Unit 24A, Madison, CT 06443
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  /27

  $589,000

  • 2 Beds
  • 2 Baths
  • 1,374 Sq Ft

  85 Legend Hill Rd Unit 85, Madison, CT 06443

  Bright and inviting end-unit ranch at Legend Hill offering easy one-floor living. Enjoy a sunny kitchen and dining area that opens to a lovely living room with cathedral ceilings and a fireplace, plus a screened-in porch for warm-weather relaxation. The primary suite features a full bath and walk-in closet, with a second bedroom and hall bath completing the main level. Additional highlights

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 693-9073

  85 Legend Hill Rd Unit 85, Madison, CT 06443
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  /14

  $2,500 per month plus fees

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

  49 Cottage Rd, Madison, CT 06443

  Welcome to your ideal rental property in Madison, CT! This charming home offers a wonderful opportunity for comfortable living in a vibrant community. Located just minutes away from several great restaurants and a nearby department store, convenience is at your doorstep. Enjoy the natural beauty of Hammonasset Beach State Park, perfect for leisurely walks and relaxation.While specific

  49 Cottage Rd, Madison, CT 06443
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  $700,000 Sold Nov 21, 2025

  • 2,555 Sq Ft
  • $274/SF
  • 30 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1968

  16 Eastwood Rd, Madison, CT 06443

  Welcome to 16 Eastwood Drive, a beautifully updated raised ranch set on over an acre of land in one of Madison's most peaceful neighborhoods. This spacious 4-bedroom, 3-bathroom home offers over 2,555 square feet of living space with a bright and functional layout. The property has been thoughtfully upgraded throughout, featuring a brand-new roof, all new windows, and completely updated

  Nancy Potts Coldwell Banker Realty

  16 Eastwood Rd, Madison, CT 06443
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  Est $2,228,974 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 4,077 Sq Ft

  11 Alexandra Ln, Madison, CT 06443

  11 Alexandra Ln, Madison, CT 06443
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  /40

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 2,632 Sq Ft

  97 Kelsey Springs Dr, Madison, CT 06443

  Beautiful 4-Bedroom Colonial in a Prime Madison Location! This immaculate home has been thoughtfully upgraded nothing left to do but move in and enjoy. The living room blends contemporary design with classic appeal, while the dedicated office provides the perfect space for working from home. A cozy family room with custom built-ins, a fantastic mud/laundry room, and four spacious bedrooms

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 323-6765

  97 Kelsey Springs Dr, Madison, CT 06443
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  /29

  $12,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,392 Sq Ft
  • House for Rent

  52 Kelsey Place, Madison, CT 06443

  Available for April, May and June at $12,000/mo. Could be available year-round at $7500/mo or Academic at $6500/mo. Discover coveted Madison living on a private beach lane complete with an in-ground pool. Embrace coastal luxury in this stunning 4-bedroom, 5.1-bathroom shoreline retreat. 52 Kelsey Place features a chef-inspired kitchen, central air, 2-car garage, large patio with fire pit and BBQ,

  Diana Hartman William Pitt Sotheby's Int'l

  52 Kelsey Place, Madison, CT 06443
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  $900,000 Sold Nov 17, 2025

  • 2,576 Sq Ft
  • $349/SF
  • 55 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1969

  15 Buttonball Ln, Madison, CT 06443

  Stunning Contemporary Home with Ultimate Outdoor Oasis! This beautifully updated contemporary-style home truly has it all-ideally located in a desirable neighborhood close to town and schools. Inside, you'll find 4 spacious bedrooms and 3 full bathrooms, including a luxurious primary suite featuring a gas fireplace, generous walk-in closets, and a spa-inspired bathroom. The heart of the home is

  Cathy Lynch Coldwell Banker Realty

  15 Buttonball Ln, Madison, CT 06443
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  Est $136,923 Not Listed For Sale

  12 Hathaway Ln, Madison, CT 06443

  12 Hathaway Ln, 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

  

  Gene Pica

  RE/MAX Alliance

  (475) 290-6060

  728 Durham Rd, Madison, CT 06443
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  /18

  $2,500 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,552 Sq Ft
  • House for Rent

  53 Liberty St Unit A, Madison, CT 06443

  Charming Guest House in Madison, CT - Available for Academic Year Rental. Tucked back on historical Liberty Street with access to private Seaview beach association, this cottage features two levels of living space. First floor is open concept with a sitting area. Appliances include washer/dryer, gas stove, microwave and refrigerator. Large windows open to a garden view. Second floor greets you

  Kira Coon William Raveis Real Estate

  53 Liberty St Unit A, Madison, CT 06443
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  $900,000 Sold Nov 14, 2025

  • 2,968 Sq Ft
  • $303/SF
  • 27 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1983

  166 Bishop Ln, Madison, CT 06443

  Custom built and first time on the market! A solid and well cared for home that exudes pride of ownership. An exceptional opportunity to enjoy the best of shoreline living in one of Madison's most desirable locations. A beautifully designed 3 bedroom, 3 bath ranch style home. Nearly 3,000 square feet of single floor living on almost an acre of land. A home loaded with upgrades that include 2

  Greg robbins Houlihan Lawrence WD

  166 Bishop Ln, Madison, CT 06443
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  Est $3,267,559 Not Listed For Sale

  • 5 Beds
  • 9 Baths
  • 6,598 Sq Ft

  61 Lantern Hill, Madison, CT 06443

  61 Lantern Hill, Madison, CT 06443
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  /40

  $1,995,000

  • 5 Beds
  • 3.5 Baths
  • 3,912 Sq Ft

  30 Meeting House Ln, Madison, CT 06443

  Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the neighboring Congregational Church, the home

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 442-9594

  30 Meeting House Ln, Madison, CT 06443
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  /25

  $2,800 total monthly price

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • Apartment for Rent

  856 Boston Post Rd Unit 1, Madison, CT 06443

  One bedroom, unfurnished apartment of approx 900 sq ft on estate-like grounds in the heart of downtown Madison. ALL UTILITIES INCLUDED, JUST BRING YOUR CELL PHONE! Interior, private lot. French doors in living room and kitchen open up onto a large porch overlooking a beautiful garden. Eat-in kitchen, laundry room, full bath. A garden path takes one to the entrance.. Owner agent, 6 month to 1 year

  Faith Whitehead William Raveis Real Estate

  856 Boston Post Rd Unit 1, Madison, CT 06443
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  $665,000 Sold Nov 14, 2025

  • 1,260 Sq Ft
  • $528/SF
  • 44 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  18 Kelsey Place, Madison, CT 06443

  Enjoy endless beach days from this charming 3-bedroom, 2-bathroom Cape retreat. Entertaining is easy with the open floor plan design, large patio, and generous yard space ideal for outdoor gatherings. The primary bedroom is conveniently set on the main floor, and 2 additional bedrooms and one full bath are upstairs. Perfectly suited for one-level living, seasonal getaways, or a permanent

  Betsy Anderson William Pitt Sotheby's Int'l

  18 Kelsey Place, Madison, CT 06443
• 

  Est $1,095,422 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,197 Sq Ft

  30 Governors Way, Madison, CT 06443

  30 Governors Way, Madison, CT 06443
• 

  

  /28

  $325,000 Pending

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

  17 Eagle Meadow Rd, Madison, CT 06443

  Located in Eagle Meadow neighborhood, this 2 bedroom 2 bathroom home is full of potential. Currently sits as two single bedroom apartments above a 3 bay garage on 1.93 acres in a wonderful neighborhood. Ideal for an investor anyone needing workshop space, or someone looking to create their dream home in cul de sac neighborhood just north of the Madison circle. Can be sold individually or with MLS

  

  Rob McConville

  William Pitt Sotheby's Int'l

  (203) 779-6248

  17 Eagle Meadow Rd, Madison, CT 06443
• 

  

  /22

  $3,500 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,051 Sq Ft
  • House for Rent

  84 Kelsey Place, Madison, CT 06443

  Immaculate, completely updated charming home available December 1st as an Annual furnished rental. Hardwood floors, stainless appliances, skylights, large windows, light and bright throughout. Just a short walk to a private, sandy beach. Wonderful, large front deck, small side deck and an outdoor shower! Recent improvements include: new stove, refrigerator, washer and dryer and hot water heater.

  Sue Knapp William Pitt Sotheby's Int'l

  84 Kelsey Place, Madison, CT 06443
• 

  $563,000 Sold Nov 14, 2025

  • 1,593 Sq Ft
  • $353/SF
  • 70 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1985

  87 Legend Hill Rd Unit 87, Madison, CT 06443

  Welcome to 87 Legend Hill Road at Legend Hill in Madison, CT! This bright and beautiful 2 bedroom, 2.5 bath ranch townhome features an open floor plan with hardwood floors and vaulted, 9+ foot ceilings throughout the living and dining room. Right off the dining room is the gorgeous sunroom to sip your morning coffee or tea. The kitchen features ample counter space and cabinets, with an eating

  Tyler Della Valle Dow Della Valle

  87 Legend Hill Rd Unit 87, Madison, CT 06443
• 

  Est $475,460 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,055 Sq Ft

  31 Samantha Ln, Madison, CT 06443

  31 Samantha Ln, Madison, CT 06443
• 

  

  /40

  $875,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 3,972 Sq Ft

  23 Horsebarn Ln, Madison, CT 06443

  Welcome to 23 Horsebarn Lane, one of the most versatile homes you will find on the market. From the newly renovated kitchen to the expansive open layout, to the first floor master suite with fireplace, this home will check all the boxes for even the most discerning buyers. The expansive 2 story foyer creates a dramatic entry while also offering easy access to everything the home offers, like the

  

  Dylan Walter

  William Raveis Real Estate

  (203) 594-8451

  23 Horsebarn Ln, Madison, CT 06443
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  /33

  $3,500 total monthly price

  • 5 Beds
  • 4 Baths
  • 2,523 Sq Ft
  • House for Rent

  6 Signal Hill Rd, Madison, CT 06443

  Welcome to the heart of Madison's downtown neighborhood. This charming four-bedroom colonial features beautifully refinished pine wood floors-completely carpet-free-and a renovated kitchen with new cabinetry and a modern oven. The spacious first floor offers a graceful hallway, inviting family room, and elegant dining area. A convenient half bathroom with laundry adds functionality, and a

  Sang Jee William Raveis Real Estate

  6 Signal Hill Rd, Madison, CT 06443
• 

  $135,000 Sold Nov 14, 2025

  • 523 Sq Ft
  • $258/SF
  • 19 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1938

  73 South St, Madison, CT 06443

  Madison-beach property! Dreaming of sunny beach days and enjoying all the shoreline lifestyle offers? Then this one is for you! Fully turnkey renovated seasonal cottage directly bordering Hammonasset Beach State Park. Enjoy the park's two miles of sandy beaches, secluded coves, picnic areas, wildlife sanctuary and 936 acres of protected waterfront lands all easily accessible from your quaint

  Rick Loranger Coldwell Banker Realty

  73 South St, Madison, CT 06443
• 

  Est $450,766 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,108 Sq Ft

  12 Samantha Ln, Madison, CT 06443

  12 Samantha Ln, Madison, CT 06443
• 

  

  /40

  $1,785,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 4,988 Sq Ft

  123 Liberty St, Madison, CT 06443

  Welcome to Liberty Street - One of Madison's Most Sought-After Addresses. This exceptional custom-built home combines timeless elegance with masterful craftsmanship, showcasing exquisite millwork and refined finishes throughout. Spend warm summer evenings on the inviting covered front porch, or step inside to find a beautifully designed interior featuring coffered ceilings in the dining room, a

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 260-9240

  123 Liberty St, Madison, CT 06443
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  /10

  $1,900 total monthly price

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

  7 Brantwood Dr Unit 7, Madison, CT 06443

  Light and bright, one bedroom apartment close to town. This unit is almost 900 sq. ft. and has a back deck, loads of storage, washer/dryer in the unit, and plenty of parking. Welcome to downtown Madison!

  Bonnie Fillion Berkshire Hathaway NE Prop.

  7 Brantwood Dr Unit 7, Madison, CT 06443
• 

  $1,080,000 Sold Nov 14, 2025

  • 3,660 Sq Ft
  • $295/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1974

  62 Wellsweep Dr, Madison, CT 06443

  An Exceptional Home in the Tall Oaks subdivision... This meticulously maintained and constantly upgraded private home in the cul-de-sac Wellsweep neighborhood is absolutely turnkey. Set on a hill, among tall oaks and beautiful landscaping, this 3-4 bedroom unique Colonial style home exudes charm with all the extra modern features, and then some. Every room is spacious and airy with hardwood

  Alison Gould Gould Group LLC

  62 Wellsweep Dr, Madison, CT 06443
• 

  Est $411,270 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  4 Stephanie Ct, Madison, CT 06443

  4 Stephanie Ct, Madison, CT 06443

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