Madison, CT Homes

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  /11

  $1,500,000 Pending

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

  38 Opening Hill Rd, Madison, CT 06443

  2024 is the year to have the home of your dreams! Come see this gorgeous enclave of four to-be-built houses in an ideal location less than 10 minutes from the center of Madison, with restaurants, beaches, shops, and the historic Green all within 5 miles. Surrounded by natural wooded beauty and bordered by Madison Conservation Land, these lots are stunning! Includes all the details you would

  Karen Rosenthal William Raveis Real Estate

  38 Opening Hill Rd, Madison, CT 06443
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  $578,000 Sold Jun 05, 2025

  100 Warpas Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,404 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Above List Price
  • $412/SF
  • 67 Days On Market

  Current Estimated Value $589,633

  Last Listing Agent Erin Connelly Coldwell Banker Realty

  100 Warpas Rd, Madison, CT 06443
• 

  Est $520,849 Not Listed For Sale

  2 Cornfield Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,966 Sq Ft
  • Built 1982

  2 Cornfield Ln, Madison, CT 06443

  Last Sold Summary

  • 3% Above List Price
  • $257/SF
  • 40 Days On Market

  • Last Sold Price $505,000
  • Sep 20, 2024

  Last Listing Agent Shoreline Homes Team William Raveis Real Estate
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  /33

  $539,900

  • 2 Beds
  • 2 Baths
  • 1,360 Sq Ft

  6 Ladshaw Dr, Madison, CT 06443

  Detached stand-alone Ranch home in sought after Kensington Acres South has been beautifully maintained and shows pride of ownership throughout. Enjoy single floor living in your 2 bedroom, 2 bath home which features granite countertops in kitchen & baths, hardwood floors, light & bright open floor plan, natural gas fireplace and a year round heated sunporch surrounded by nature that will be your

  Greg robbins Houlihan Lawrence WD

  6 Ladshaw Dr, Madison, CT 06443
• 

  $437,000 Sold Feb 26, 2026

  1543 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 3,711 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Above List Price
  • $118/SF
  • 31 Days On Market

  Current Estimated Value $435,293

  Last Listing Agent Rob McConville RE/MAX Heritage

  1543 Durham Rd, Madison, CT 06443
• 

  Est $432,917 Not Listed For Sale

  1467 Durham Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 1,611 Sq Ft
  • Built 1961

  1467 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 40% Above List Price
  • $192/SF
  • 70 Days On Market

  • Last Sold Price $310,000
  • Jul 28, 2023

  Last Listing Agent Rose Bevilacqua Coldwell Banker Realty
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  /20

  $174,900

  • 2 Beds
  • 1 Bath
  • 592 Sq Ft

  32 North St, Madison, CT 06443

  32 North Street is calling you home! Set on one of the largest lots in Dud's Village, this lovely cottage is the idyllic seasonal abode. Equipped with 2 bedrooms, 1 full bath, and an outdoor shower, you will surely enjoy your summers along the Madison shoreline here. The recently refreshed kitchen and fresh coat of paint throughout will undoubtedly delight. And let's not forget the new floors in

  Melanie Abbott William Pitt Sotheby's Int'l

  32 North St, Madison, CT 06443
• 

  $1,200,000 Sold Mar 13, 2026

  5 Evarts Ln, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 2,418 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Above List Price
  • $496/SF
  • 33 Days On Market

  Current Estimated Value $1,135,896

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  5 Evarts Ln, Madison, CT 06443
• 

  Est $628,986 Not Listed For Sale

  35 White Cedar Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,150 Sq Ft
  • Built 1984

  35 White Cedar Dr, Madison, CT 06443

  Last Sold Summary

  • 2% Above List Price
  • $286/SF
  • 24 Days On Market

  • Last Sold Price $615,000
  • Nov 25, 2024

  Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty
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  /40

  $699,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,025 Sq Ft

  69 Squires Rd, Madison, CT 06443

  Meticulously reimagined from top to bottom, this stunning contemporary home delivers 2,025 sq ft of turnkey luxury on over an acre of level land. Tucked on a peaceful street, the residence boasts 3 bedrooms and 3 full baths, highlighted by a main-level primary suite with its own fireplace, patio access, and spa-inspired bath. There is a versatile 2nd-floor suite with full bath: perfect for an

  Sue Woods William Pitt Sotheby's Int'l

  69 Squires Rd, Madison, CT 06443
• 

  $690,000 Sold Aug 13, 2025

  41 Sportsman Hill Rd, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 3,120 Sq Ft
  • Built 1966

  Last Sold Summary

  • 10% Above List Price
  • $221/SF
  • 33 Days On Market

  Current Estimated Value $701,581

  Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  41 Sportsman Hill Rd, Madison, CT 06443
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  Est $687,079 Not Listed For Sale

  24 Genesee Ln, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,520 Sq Ft
  • Built 1988

  24 Genesee Ln, Madison, CT 06443

  Last Sold Summary

  • 25% Above List Price
  • $218/SF
  • 126 Days On Market

  • Last Sold Price $550,000
  • May 26, 2023

  Last Listing Agent Cathy Lynch Coldwell Banker Realty
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  /34

  $499,900

  • 4 Beds
  • 2 Baths
  • 2,192 Sq Ft

  1281 Durham Rd, Madison, CT 06443

  SELLER FINANCING AVAILBLE Positioned in a highly desirable Madison location just minutes from town, shoreline beaches, and local shops, 1281 Durham Road delivers space, versatility, and opportunity on approximately half an acre. This property offers a flexible layout rarely found at this value point in the shoreline market. The main level showcases a generously sized living room centered around a

  Michelle Lorenzetti Premier Re Group LLC

  1281 Durham Rd, Madison, CT 06443
• 

  $561,500 Sold Mar 09, 2026

  21 Apple Way, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,414 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Above List Price
  • $397/SF
  • 2 Days On Market

  Current Estimated Value $544,157

  Last Listing Agent Rachel Welch William Raveis Real Estate

  21 Apple Way, Madison, CT 06443
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  Est $891,303 Not Listed For Sale

  145 Genesee Ln, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 4,366 Sq Ft
  • Built 1995

  145 Genesee Ln, Madison, CT 06443

  Last Sold Summary

  • 14% Above List Price
  • $180/SF
  • 0 Days On Market

  • Last Sold Price $785,000
  • Oct 06, 2023

  Last Listing Agent Rose Ciardiello William Raveis Real Estate
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  /40

  $624,900 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,642 Sq Ft

  6 Yankee Peddler Path, Madison, CT 06443

  Light, bright, and full of potential, this appealing home is ideally located close to everything Madison has to offer. Set on a level corner lot, the property offers flexibility, visibility, and multiple possibilities for outdoor living or future enhancements. Just 1-2 miles to everything important that Madison has to offer like East Wharf Beach, I95, the Shoreline Greenway Trail, Hammonasset

  Willard Finkle Coldwell Banker Realty

  6 Yankee Peddler Path, Madison, CT 06443
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  $1,250,000 Sold Apr 21, 2026

  908 Boston Post Rd Unit 908, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,368 Sq Ft
  • Built 2021

  Last Sold Summary

  • 7% Below List Price
  • $528/SF
  • 110 Days On Market

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  908 Boston Post Rd Unit 908, Madison, CT 06443
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  Est $1,238,465 Not Listed For Sale

  546 Summer Hill Rd, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 6,267 Sq Ft
  • Built 2012

  546 Summer Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 1% Above List Price
  • $196/SF
  • 33 Days On Market

  • Last Sold Price $1,230,000
  • Sep 06, 2023

  Last Listing Agent Cathy Lynch Coldwell Banker Realty
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  /37

  $2,349,000

  • 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. Now available with additional closet space and newly finished den/office. 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

  Margaret Muir William Pitt Sotheby's Int'l

  64 Webster Point Rd, Madison, CT 06443
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  $1,400,000 Sold Jul 07, 2025

  36 Manzoni Farm Dr, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 4,936 Sq Ft
  • Built 2001

  Last Sold Summary

  • 8% Above List Price
  • $284/SF
  • 47 Days On Market

  Current Estimated Value $1,449,661

  Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  36 Manzoni Farm Dr, Madison, CT 06443
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  Est $826,592 Not Listed For Sale

  29 Bridle Path Ln, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 3,177 Sq Ft
  • Built 1985

  29 Bridle Path Ln, Madison, CT 06443

  Last Sold Summary

  • 5% Above List Price
  • $247/SF
  • 4 Days On Market

  • Last Sold Price $785,000
  • Aug 31, 2023

  Last Listing Agent Phoebe Schreiner William Pitt
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  /35

  $1,450,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 1,999 Sq Ft

  115 Harbor Ave, Madison, CT 06443

  Live the shoreline lifestyle in this beautifully updated 4-6 bedroom, 3-bath Colonial, just 88 steps from your very own private beach. Perfectly designed for both everyday living and entertaining, the open-concept main level flows seamlessly from dining to living, anchored by a cozy fireplace and filled with natural light. A screened-in porch with sweeping water views sets the stage for morning

  Alan Spotlow William Raveis Real Estate

  115 Harbor Ave, Madison, CT 06443
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  $693,000 Sold Jan 30, 2026

  29 Circle Beach Rd, Madison, CT 06443

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1935

  Last Sold Summary

  • 1% Below List Price
  • $962/SF
  • 5 Days On Market

  Current Estimated Value $708,113

  Last Listing Agent Gary Piccirillo RE/MAX Right Choice

  29 Circle Beach Rd, Madison, CT 06443
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  Est $878,399 Not Listed For Sale

  20 Northwood Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,575 Sq Ft
  • Built 1993

  20 Northwood Rd, Madison, CT 06443

  Last Sold Summary

  • 6% Above List Price
  • $231/SF
  • 33 Days On Market

  • Last Sold Price $825,000
  • Apr 17, 2025

  Last Listing Agent Kirsten Adams William Pitt
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  /13

  $85,000

  • 1 Bed
  • 0.5 Baths
  • 540 Sq Ft

  15 North St, Madison, CT 06443

  seasonal cottage, must be purchased with CASH. The cottage is charming and a close walk to the beach and all that the town of Madison has to offer. Hammonassett Beach is a quick drive away. Conveniant to Route #1 and the local restaurants and shops. The cottage is one bedroom and one bathroom. This cottage is a perfect weekend destination or summer getaway, this is what coastal living in Madison

  Alan Barberino Alan Barberino Real Estate LLC

  15 North St, Madison, CT 06443
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  $692,000 Sold Aug 08, 2025

  00 Stone Rd, Madison, CT 06443

  • Land
  • 1 Acre
  • $692,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 156 Days On Market

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

  00 Stone Rd, Madison, CT 06443
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  Est $902,329 Not Listed For Sale

  22 Northwood Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,765 Sq Ft
  • Built 1994

  22 Northwood Rd, Madison, CT 06443

  Last Sold Summary

  • 17% Above List Price
  • $205/SF
  • 124 Days On Market

  • Last Sold Price $770,000
  • Jan 03, 2024

  Last Listing Agent Rhonda Mesenbourg Keller Williams Coastal
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  /39

  $2,375,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 4,517 Sq Ft

  132 Summer Hill Rd, Madison, CT 06443

  PRISTINE NEW CONSTRUCTION where thoughtful design meets high end craftsmanship. This newly built four-bedroom, four-and-a-half bathroom home 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
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  $775,000 Sold Jan 16, 2026

  48 Shepherds Trail, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 4,879 Sq Ft
  • Built 1991

  Last Sold Summary

  • 9% Below List Price
  • $159/SF
  • 170 Days On Market

  Current Estimated Value $822,523

  Last Listing Agent Erin Connelly Coldwell Banker Realty

  48 Shepherds Trail, Madison, CT 06443
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  Est $1,076,082 Not Listed For Sale

  20 Hidden Springs Rd, Madison, CT 06443

  • 5 Beds
  • 3.5 Baths
  • 4,881 Sq Ft
  • Built 1988

  20 Hidden Springs Rd, Madison, CT 06443

  Last Sold Summary

  • 19% Above List Price
  • $185/SF
  • 41 Days On Market

  • Last Sold Price $901,000
  • Jun 23, 2023

  Last Listing Agent Phoebe Schreiner William Pitt
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  /40

  $3,795,000 Pending

  • 4 Beds
  • 5 Baths
  • 4,505 Sq Ft

  98 Island Ave, Madison, CT 06443

  Welcome to 98 Island Avenue in Madison, a stunning coastal residence just a short walk to the beach and town. Custom built in 2016 w/extraordinary attention to detail, this home combines timeless elegance with modern convenience. Inside, you'll find soaring 9-foot ceilings, 8-foot doors, hurricane-rated Andersen windows, & polished nickel Baldwin hardware throughout. The chef's kitchen is a

  Susan Clifford Coldwell Banker Realty

  98 Island Ave, Madison, CT 06443
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  $325,000 Sold Aug 29, 2025

  16 Brantwood Dr, Madison, CT 06443

  • 2 Beds
  • 3 Baths
  • 1,332 Sq Ft
  • Built 1986

  Last Sold Summary

  • 13% Below List Price
  • $244/SF
  • 210 Days On Market

  Current Estimated Value $340,425

  Last Listing Agent Bette Zollshan William Pitt Sotheby's Int'l

  16 Brantwood Dr, Madison, CT 06443
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  Est $590,205 Not Listed For Sale

  26 Princess Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,582 Sq Ft
  • Built 1965

  26 Princess Dr, Madison, CT 06443

  Last Sold Summary

  • 22% Above List Price
  • $187/SF
  • 3 Days On Market

  • Last Sold Price $482,000
  • Jun 02, 2023

  Last Listing Agent Susan Wagner Berkshire Hathaway Home Services
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  /40

  $2,495,000

  • 3 Beds
  • 3.5 Baths
  • 3,306 Sq Ft

  61 Hartford Ave, Madison, CT 06443

  Own an architectural masterpiece with waterviews! Rarely is a Robert Page (AIA) designed coastal home available and this is one of his most compelling. A collaboration with master builders Baldwin and Baldwin and executed with precision, this 3300 sf home with three exterior decks, (including a "Skydeck"), unfolds over four levels. Finished in 2010, this 3(+) bedroom, 3.1 bath gem offers 3300

  Margaret Muir William Pitt Sotheby's Int'l

  61 Hartford Ave, Madison, CT 06443
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  $1,125,000 Sold Jun 25, 2025

  675 Durham Rd, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 3,435 Sq Ft
  • Built 2020

  Last Sold Summary

  • 6% Below List Price
  • $328/SF
  • 106 Days On Market

  Current Estimated Value $1,198,080

  Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

  675 Durham Rd, Madison, CT 06443
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  Est $586,390 Not Listed For Sale

  160 Princess Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,455 Sq Ft
  • Built 1972

  160 Princess Dr, Madison, CT 06443

  Last Sold Summary

  • 21% Above List Price
  • $198/SF
  • 3 Days On Market

  • Last Sold Price $485,000
  • Jul 21, 2023

  Last Listing Agent Toni Iandoli William Pitt
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  /39

  $825,000 Pending

  • 3 Beds
  • 4 Baths
  • 3,766 Sq Ft

  50 Overbrook Rd, Madison, CT 06443

  Welcome to a beautiful Cape Cod-Contemporary retreat that perfectly blends modern updates with a comfortable, inviting atmosphere. The heart of this home is the stunning chef's kitchen, featuring a large center island with seating for 4, professional gas cooking, high-end appliances, and an incredible amount of pantry and storage space. It flows naturally into the dining room, where a cozy gas

  Kate Esposito William Pitt Sotheby's Int'l

  50 Overbrook Rd, Madison, CT 06443
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  $799,000 Sold Nov 25, 2025

  52 Copse Rd, Madison, CT 06443

  • 3 Beds
  • 1 Bath
  • 1,382 Sq Ft
  • Built 1850

  Last Sold Summary

  • $578/SF
  • 11 Days On Market

  Current Estimated Value $795,939

  Last Listing Agent Laureen Kennedy Coldwell Banker Realty

  52 Copse Rd, Madison, CT 06443
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  Est $540,025 Not Listed For Sale

  51 Princess Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1969

  51 Princess Dr, Madison, CT 06443

  Last Sold Summary

  • 17% Above List Price
  • $219/SF
  • 6 Days On Market

  • Last Sold Price $460,000
  • Jun 29, 2023

  Last Listing Agent Kirsten Adams William Pitt
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  /38

  $2,875,000

  • 5 Beds
  • 5.5 Baths
  • 7,139 Sq Ft

  37 Lantern Hill Rd, Madison, CT 06443

  An unbeatable location, 37 Lantern Hill is set in one of Madison's most desirable in-town neighborhoods. Close to sandy beaches, charming town center and the Madison Country Club, recreation and everyday conveniences are right at your doorstep. Traditional by design with ten foot ceilings, abundant natural light and generously scaled rooms that create an airy feel, ideal for relaxing or

  Margaret Muir William Pitt Sotheby's Int'l

  37 Lantern Hill Rd, Madison, CT 06443

Showing Results 161 - 200, Page 5 of 18