Madison, CT Homes

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  $1,350,000

  • 3 Beds
  • 2.5 Baths
  • 2,368 Sq Ft

  908 Boston Post Rd Unit 908, Madison, CT 06443

  Experience luxury living in the heart of Madison. This beautifully designed 3-bedroom, 2.5-bath townhouse offers an open layout with 9' ceilings, beautiful, oversized windows, and a gorgeous chef's kitchen equipped with Sub-Zero and Wolf appliances. The light-filled living and dining areas feature a cozy fireplace and seamless flow. The vaulted, south-facing primary suite includes a walk-in

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 354-7246

  908 Boston Post Rd Unit 908, Madison, CT 06443
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  $20,000 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

  (475) 290-6357

  72 Cherry Ln, Madison, CT 06443
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  $1,200,000 Sold Oct 09, 2025

  110 E Wharf Rd, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1930

  Last Sold Summary

  • 7% Below List Price
  • $759/SF
  • 11 Days On Market

  Current Estimated Value $1,204,903

  Last Listing Agent Lisa Daniele William Raveis Real Estate

  110 E Wharf Rd, Madison, CT 06443
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  Est $785,707 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,918 Sq Ft

  32 Lakewood Dr, Madison, CT 06443

  32 Lakewood Dr, Madison, CT 06443
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  $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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  $6,000 total monthly price

  • 4 Beds
  • 3 Baths
  • 3,372 Sq Ft
  • House for Rent

  5 Middle Beach Rd, Madison, CT 06443

  Academic rent available January through June. This gorgeous renovated Victorian offers views of Long Island sound and steps to a sandy beach. The open floor plan makes it an ease for entertaining, a large kitchen island is a heart of the house and great for casual dining. The fireplace is the center of the great room to gather around on chilly nights. Off the great room is a sun filled formal

  Alice Trautman William Raveis Real Estate

  5 Middle Beach Rd, Madison, CT 06443
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  $711,000 Sold Aug 21, 2025

  29 Flintlock Rd, Madison, CT 06443

  • 4 Beds
  • 1.5 Baths
  • 2,458 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Above List Price
  • $289/SF
  • 40 Days On Market

  Current Estimated Value $708,653

  Last Listing Agent Betsy Anderson William Pitt Sotheby's Int'l

  29 Flintlock Rd, Madison, CT 06443
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  Est $201,381 Not Listed For Sale

  2117 Durham Rd, Madison, CT 06443

  2117 Durham Rd, Madison, CT 06443
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  $479,000 Under Contract

  • 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

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 344-7322

  40 Legend Hill Rd, Madison, CT 06443
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  $35,000 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,741 Sq Ft
  • House for Rent

  12 Flower Ave, Madison, CT 06443

  Available from 7/6/2026 to 8/31/2026 for $35K. Owner will also consider renting from 7/6/2026 to 7/31/2026 for 18K or from 8/1/2026 to 8/31/2026 for 20K. This home usually goes REALLY FAST because of it's outstanding location and the amenities it offers. Enjoy a summer vacation in an impeccably maintained 4 bedroom, 2 full bath and one 1/2 bath home that is beautifully furnished and fully stocked

  Susan Clifford Coldwell Banker Realty

  12 Flower Ave, Madison, CT 06443
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  $1,010,000 Sold Jan 09, 2026

  37 Quail Run, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,409 Sq Ft
  • Built 1990

  Last Sold Summary

  • 2% Above List Price
  • $296/SF
  • 28 Days On Market

  Last Listing Agent Nancy Potts Coldwell Banker Realty

  37 Quail Run, Madison, CT 06443
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  Est $2,201,962 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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  $359,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft

  313 Bradley Corners Rd, Madison, CT 06443

  Lots of potential in this 4-bedroom 2 full bath colonial in Madison. Private yard, kitchen with adjoining family room, large screen porch leading to deck and backyard, living room with fireplace and dining room. The upstairs as 4 bedrooms all with hardwood floors. A full basement and 2 car garage. Investors take notice. This home needs updating and is being sold as. Great quiet street. With some

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 941-6912

  313 Bradley Corners Rd, Madison, CT 06443
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  $8,000 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • House for Rent

  57 Harbor Ave, Madison, CT 06443

  AVAILABLE June $7,000; July $8,000; August $7,000!...The entire three months, $20,000. You don't want to miss this one... A short walk to a nice sandy beach on Long Island Sound. Cozy and efficient Bungalow in Beach Community. Open Floor Plan. Kitchen with granite counters, hardwood floors throughout, central air conditioning. FIRST FLOOR Master Bedroom with full bath and king bed, and second

  Alison Gould Gould Group LLC

  57 Harbor Ave, Madison, CT 06443
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  $725,000 Sold Dec 22, 2025

  318 Horse Pond Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,622 Sq Ft
  • Built 1994

  Last Sold Summary

  • $277/SF
  • 40 Days On Market

  Last Listing Agent Carol Farmer William Raveis Real Estate

  318 Horse Pond Rd, Madison, CT 06443
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  Est $137,821 Not Listed For Sale

  12 Hathaway Ln, Madison, CT 06443

  12 Hathaway Ln, Madison, CT 06443
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  $995,000 Pending

  • 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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  $6,000 total monthly price

  • 5 Beds
  • 4.5 Baths
  • 3,697 Sq Ft
  • House for Rent

  19 Middle Beach Rd, Madison, CT 06443

  This beautiful waterfront home has unobstructed views of Long Island Sound.This gorgeous home was built in 2012 with all the bells and whistles. Available on February 1st until June 21st of 2026. Ask about pets. 5 bedrooms/4 baths, City Water, Natural Gas and Central Air. Lots of parking.

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  19 Middle Beach Rd, Madison, CT 06443
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  $1,927,500 Sold Aug 19, 2025

  44 E Wharf Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 1924

  Last Sold Summary

  • 2% Above List Price
  • $714/SF
  • 8 Days On Market

  Current Estimated Value $1,878,690

  Last Listing Agent Margaret Muir William Pitt Sotheby's Int'l

  44 E Wharf Rd, Madison, CT 06443
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  Est $3,260,709 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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  $490,000 Coming Soon

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

  1 Wilshire Rd Unit 1D, Madison, CT 06443

  Enjoy coastal living in this beautifully updated 2-bed, 2.5-bath end-unit condo in Madison, perfectly located just a few minutes from downtown Madison and Hammonasset Beach. This move-in-ready home features fully updated bathrooms, gas heat, and abundant storage, including an oversized garage and plentiful attic space both within the home and above the garage. Outside, the property feels like a

  

  Cory Tyler

  Berkshire Hathaway NE Prop.

  (203) 577-5269

  1 Wilshire Rd Unit 1D, Madison, CT 06443
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  $4,250 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,386 Sq Ft
  • Apartment for Rent

  82 Wall St Unit 200, Madison, CT 06443

  Spacious, fully furnished 2nd floor apartment located in the heart of downtown Madison. Light and bright loft like open concept floor plan with granite countertops, stainless appliances, central air and in-unit laundry. Halfway between New York and Boston, minutes from fine dining, specialty shops, town beaches, library, train and I95.

  Rebecca Dowler CMD Realty LLC

  82 Wall St Unit 200, Madison, CT 06443
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  $770,000 Sold Jul 31, 2025

  24 Grouse Ln, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 2,356 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Above List Price
  • $327/SF
  • 13 Days On Market

  Current Estimated Value $774,421

  Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

  24 Grouse Ln, Madison, CT 06443
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  Est $1,094,704 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
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  $574,900 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,828 Sq Ft

  9 Old Farms Rd, Madison, CT 06443

  Discover coastal bliss in this updated 4-bedroom, 1.5-bathroom home, spanning over 1,800 sq. ft. in this serene Madison, CT neighborhood-just a quick 6-minute, 2.7-mile drive to the sun-kissed beaches of Long Island Sound. Ideal for turnkey living with modern comforts and effortless seaside vibes. Enter to gleaming hardwood floors flowing through a semi-open layout, linking the inviting living

  Luke Florian SSG Real Estate LLC

  9 Old Farms Rd, Madison, CT 06443
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  $3,500 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,809 Sq Ft
  • House for Rent

  156 Concord Dr, Madison, CT 06443

  Quintessential New England Cape on over an acre, situated perfectly to enjoy the serene natural beauty of North Madison, while being only minutes from downtown or Madison beaches. Main level of the house features hardwood floors throughout an incredibly versatile floorplan with multiple living areas, large newly updated kitchen, dining room (or den) and convenient half bath... as well as 2 wood

  Jared Verrillo Seabury Hill REALTORS

  156 Concord Dr, Madison, CT 06443
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  $1,045,000 Sold Sep 26, 2025

  39 Madison Ave, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 1,891 Sq Ft
  • Built 1957

  Last Sold Summary

  • 10% Above List Price
  • $553/SF
  • 13 Days On Market

  Current Estimated Value $1,045,983

  Last Listing Agent Phoebe Finch William Pitt Sotheby's Int'l

  39 Madison Ave, Madison, CT 06443
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  Est $466,785 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
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  $2,495,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,565 Sq Ft

  31 Stony Lane Lot 3 Rd, Madison, CT 06443

  Indulge in refined living at our Barberry Farm Open Space subdivision with Waterside Building and Development. Your bespoke home, spanning 3,000 to 4,000+ sq ft, promises not just spacious elegance but high-end finishes and meticulous craftsmanship. Situated within walking distance to Madison beaches and a golf course, this enclave blends luxury with convenience. Revel in the exquisite details of

  Lindsay Greenberg William Raveis Real Estate

  31 Stony Lane Lot 3 Rd, Madison, CT 06443
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  $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 rental. You'll appreciate the classic floor plan highlighted on the 1st floor by the kitchen, family room, living room, sun porch, powder room and office. Upstairs you'll find two nicely sized bedrooms and a full bath. The kitchen has a wonderful vintage vibe with a blend of

  Phoebe Finch William Pitt Sotheby's Int'l

  43 Neck Rd, Madison, CT 06443
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  $590,000 Sold Sep 29, 2025

  7 Downing Way, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,853 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $318/SF
  • 24 Days On Market

  Current Estimated Value $615,684

  Last Listing Agent Margaret Muir William Pitt Sotheby's Int'l

  7 Downing Way, Madison, CT 06443
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  Est $433,653 Not Listed For Sale

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

  12 Samantha Ln, Madison, CT 06443

  12 Samantha Ln, Madison, CT 06443
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  $2,295,000

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

  64 Webster Point Rd, Madison, CT 06443

  Spacious with amazing waterfront quality views, sited one house from Long Island Sound on a quiet cul de sac. Offering privacy and timeless appeal, the home features light filled rooms, 10-foot ceilings on the first floor 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

  Margaret Muir William Pitt Sotheby's Int'l

  64 Webster Point Rd, Madison, CT 06443
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  $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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  $730,000 Sold Dec 23, 2025

  677 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • Built 2022

  Last Sold Summary

  • 9% Below List Price
  • $346/SF
  • 145 Days On Market

  Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

  677 Durham Rd, Madison, CT 06443
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  Est $413,858 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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  $670,000

  • 4 Beds
  • 2.5 Baths
  • 3,057 Sq Ft

  39 Stepping Stone Ln, Madison, CT 06443

  New price and $20,000 seller credit offered. Set on over 2 private acres at the end of a quiet cul de sac, this classic Madison Colonial offers space, privacy, and flexible living options. The kitchen features stainless steel appliances and a pantry, and new flooring throughout the main level significantly enhances the home's feel. A screened in porch extends the living space outdoors,

  Cindy Breckheimer Forever Homes Real Estate LLC

  39 Stepping Stone Ln, Madison, CT 06443
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  $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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  $550,000 Sold Jun 23, 2025

  67 New Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • Built 1960

  Last Sold Summary

  • $349/SF
  • 201 Days On Market

  Current Estimated Value $569,317

  Last Listing Agent Nancy Potts Coldwell Banker Realty

  67 New Rd, Madison, CT 06443
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  Est $455,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,916 Sq Ft

  2270 Durham Rd, Madison, CT 06443

  2270 Durham Rd, Madison, CT 06443

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