Madison, CT Homes

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  $3,200,000

  • 5 Beds
  • 6 Baths
  • 4,450 Sq Ft

  77 E Wharf Rd, Madison, CT 06443

  Welcome to 77 East Wharf! This beautifully designed five-bedroom Cape Cod-style home is perfectly situated high on the property to capture breathtaking views of the Long Island Sound and tranquil Fence Creek. Ideal for entertaining or hosting beach-loving visitors, this home also includes a charming one-bedroom apartment over the garage. Begin your experience with a private walkway bordered by a

  Meig Walz Newcomb Coldwell Banker Realty

  77 E Wharf 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 $1,416,127

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

  36 Manzoni Farm Dr, Madison, CT 06443
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  Est $1,339,803 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

  • 9% Above List Price
  • $196/SF
  • 33 Days On Market

  Last Sold Price $1,230,000

  Last Listing Agent Cathy Lynch Coldwell Banker Realty
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  /31

  $675,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 1.5 Baths
  • 1,288 Sq Ft

  42 Neck Rd, Madison, CT 06443

  Live the shoreline lifestyle in the highly sought after beach area of Neck Road. This charming home offers a rare opportunity to enjoy coastal living in a location that truly has it all. An inviting front porch welcomes you in and provides the perfect spot for morning coffee or relaxing at the end of the day. Inside, the spacious living room features beautiful built-in bookshelves and it flows

  Anne-Marie Pagli William Raveis Real Estate

  42 Neck Rd, 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 $782,908

  Last Listing Agent Gary Piccirillo RE/MAX Right Choice

  29 Circle Beach Rd, Madison, CT 06443
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  Est $810,834 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

  • 3% Above List Price
  • $247/SF
  • 4 Days On Market

  Last Sold Price $785,000

  Last Listing Agent Phoebe Schreiner William Pitt
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  $499,000

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

  14 Centre Village Dr, Madison, CT 06443

  Discover the allure of Centre Village in this light-filled one-bedroom, 1.5-bath end unit. Hardwood floors flow through the entry, living room, and dining room, where oversized windows and a gas fireplace create a warm, inviting atmosphere. The bright eat-in kitchen opens to a versatile den with sliders leading to your private deck and stone patio-perfect for indoor-outdoor living. The first

  Sue Knapp William Pitt Sotheby's Int'l

  14 Centre Village Dr, Madison, CT 06443
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  $400,000 Sold Apr 25, 2025

  164 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 1,438 Sq Ft
  • Built 1916

  Last Sold Summary

  • 9% Below List Price
  • $278/SF
  • 43 Days On Market

  Current Estimated Value $435,265

  Last Listing Agent Linda Toscano Coldwell Banker Realty

  164 Durham Rd, Madison, CT 06443
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  Est $901,521 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

  Last Listing Agent Rhonda Mesenbourg Keller Williams Coastal
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  $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
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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 $1,076,052 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

  Last Listing Agent Phoebe Schreiner William Pitt
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  $675,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,640 Sq Ft

  41 Harbor Ave, Madison, CT 06443

  Charming Cape Cod in the Harbor Avenue Beach community, with a short walk to a lovely sandy beach and Long Island Sound. Lots of room for entertaining friends and family, including a large enclosed heated porch surrounded by sliders that lead to a side deck and fenced back yard. Family Room with wood stove. Two bedrooms (one on the first level) and 2 full baths. Some upgrades, including new

  Alison Gould Gould Group LLC

  41 Harbor Ave, 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 $802,948

  Last Listing Agent Erin Connelly Coldwell Banker Realty

  48 Shepherds Trail, Madison, CT 06443
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  Est $576,717 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

  • 20% Above List Price
  • $187/SF
  • 3 Days On Market

  Last Sold Price $482,000

  Last Listing Agent Susan Wagner Berkshire Hathaway Home Services
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  /31

  $1,100,000

  • Land
  • 3.67 Acres
  • $299,728 per Acre

  4 Boston Post Rd, Madison, CT 06443

  Rarely does a Legacy Property, with a "Shovel-Ready" vision, arrive with the hardest yards of coastal development already complete. East River Landing is a fully de-risked, 3.67-acre asset at the Madison/Guilford gateway, combining an extensive marina income opportunity with unprecedented residential scalability. Approved Maritime Asset. Forget proposed plans-this is a fully built, 46-slip marina

  Michael Barnes Silver and Oak Realty

  4 Boston Post Rd, 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 $343,708

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

  16 Brantwood Dr, Madison, CT 06443
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  Est $594,055 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

  • 22% Above List Price
  • $198/SF
  • 3 Days On Market

  Last Sold Price $485,000

  Last Listing Agent Toni Iandoli William Pitt
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  $734,900

  • 4 Beds
  • 2.5 Baths
  • 3,212 Sq Ft

  174 Concord Dr, Madison, CT 06443

  Step into this exquisitely renovated colonial-style residence, where classic charm seamlessly blends with contemporary sophistication. Gleaming hardwood floors flow throughout the main living spaces, reflecting natural light and enhancing the home's warm ambiance. The heart of the home is a stunning chef's kitchen, thoughtfully designed with state-of-the-art appliances, quartz countertops, and

  Terence Dominick Exceptional Real Estate LLC

  174 Concord Dr, 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 $1,183,906

  Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

  675 Durham Rd, Madison, CT 06443
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  Est $529,344 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

  • 15% Above List Price
  • $219/SF
  • 6 Days On Market

  Last Sold Price $460,000

  Last Listing Agent Kirsten Adams William Pitt
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  $159,900 Under Contract

  • Land
  • 1.43 Acres
  • $111,818 per Acre

  0 Skytop Dr, Madison, CT 06443

  Great opportunity to build in an established neighborhood in the beautiful shoreline community of Madison, CT! Large 1.43 acre rear lot is extremely private and ready for your dream home. Located just a short 1.5mi / 5 minute drive to downtown with easy access to I-95 and a short drive to Hammonasset Beach. Per town will need an updated perc test for final approval. Agent/owner

  Luke Florian SSG Real Estate LLC

  0 Skytop Dr, 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 $811,278

  Last Listing Agent Laureen Kennedy Coldwell Banker Realty

  52 Copse Rd, Madison, CT 06443
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  Est $451,609 Not Listed For Sale

  289 Old Toll Rd, Madison, CT 06443

  • 10 Beds
  • 3 Baths
  • 3,039 Sq Ft
  • Built 1938

  289 Old Toll Rd, Madison, CT 06443

  Last Sold Summary

  • 46% Above List Price
  • $102/SF
  • 3 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Lauren Freedman Coldwell Banker Realty
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  $625,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,656 Sq Ft

  40 Puritan Ln, Madison, CT 06443

  HIGHEST AND BEST DUE BY SUNDAY, JANUARY 18TH AT 3 PM. Recent, significant capital improvements, including a brand new roof and three skylights, plus two new septic tanks, offer immediate peace of mind in this spacious, one-owner home. Ideally situated south of I-95 on a quiet cul-de-sac, this property is just one mile from downtown, combining privacy with exceptional convenience and access to

  Barbara Goetsch William Pitt Sotheby's Int'l

  40 Puritan Ln, Madison, CT 06443
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  $927,000 Sold Mar 14, 2025

  13 Deveron Dr, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 3,523 Sq Ft
  • Built 1998

  Last Sold Summary

  • 18% Above List Price
  • $263/SF
  • 3 Days On Market

  Current Estimated Value $1,017,353

  Last Listing Agent Allison Ciarcia William Raveis Real Estate

  13 Deveron Dr, Madison, CT 06443
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  Est $640,382 Not Listed For Sale

  316 Race Hill Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 2,481 Sq Ft
  • Built 1964

  316 Race Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 11% Above List Price
  • $233/SF
  • 35 Days On Market

  Last Sold Price $577,500

  Last Listing Agent Sheila Tinn-Murphy Berkshire Hathaway Home Services
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  $850,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,982 Sq Ft

  25 Williamsburg Cir, Madison, CT 06443

  Tucked away in one of Madison's most desirable neighborhoods, this beautifully maintained four-bedroom, 3.5-bath Cape-style Colonial offers over 4,000 square feet of living space in a truly serene setting. Surrounded by scenic hiking trails and the picturesque Hammonasset River, the flat, private lot is a nature lover's dream-peaceful, tranquil, and perfect for outdoor enjoyment. Relax by the

  Toni Iandoli William Pitt Sotheby's Int'l

  25 Williamsburg Cir, Madison, CT 06443
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  $1,225,000 Sold Feb 18, 2026

  41 Allison Dr, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 3,609 Sq Ft
  • Built 2003

  Last Sold Summary

  • 5% Below List Price
  • $339/SF
  • 66 Days On Market

  Current Estimated Value $1,288,022

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

  41 Allison Dr, Madison, CT 06443
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  Est $562,025 Not Listed For Sale

  138 Squires Rd, Madison, CT 06443

  • 4 Beds
  • 1.5 Baths
  • 1,868 Sq Ft
  • Built 1972

  138 Squires Rd, Madison, CT 06443

  Last Sold Summary

  • 4% Above List Price
  • $289/SF
  • 28 Days On Market

  Last Sold Price $540,000

  Last Listing Agent Samantha Celentano Coldwell Banker Realty
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  $325,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  42 Wildcat Rd, Madison, CT 06443

  Ranch-style single-family home situated on 1 acre, just 5 minutes from Hammonasset State Beach. The property features classic New England stone walls surrounding much of the land, along with a detached two-car garage. Inside, has nice looking exposed beams! Then living room, kitchen, three bedrooms, and one bathroom-all on the main floor. Full unfinished basement with an exterior hatch. The

  Ethan Maddalena Berkshire Hathaway NE Prop.

  42 Wildcat Rd, Madison, CT 06443
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  $212,000 Sold Aug 15, 2025

  26 North St, Madison, CT 06443

  • 2 Beds
  • 1 Bath
  • 647 Sq Ft
  • Built 1960

  Last Sold Summary

  • $328/SF
  • 19 Days On Market

  Last Listing Agent Laurie McCann William Pitt Sotheby's Int'l

  26 North St, Madison, CT 06443
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  Est $847,419 Not Listed For Sale

  30 Georgetown Cir, Madison, CT 06443

  • 5 Beds
  • 3 Baths
  • 3,594 Sq Ft
  • Built 1978

  30 Georgetown Cir, Madison, CT 06443

  Last Sold Summary

  • 16% Above List Price
  • $203/SF
  • 2 Days On Market

  Last Sold Price $728,000

  Last Listing Agent Phoebe Schreiner William Pitt
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  $265,000 Sold Feb 19, 2026

  268 Durham Rd, Madison, CT 06443

  • Land
  • 2.29 Acres
  • $115,721 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 24 Days On Market

  Current Estimated Value $273,112

  Last Listing Agent Kirsten Adams William Pitt Sotheby's Int'l

  268 Durham Rd, Madison, CT 06443
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  Est $997,074 Not Listed For Sale

  35 Georgetown Cir, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 3,004 Sq Ft
  • Built 1978

  35 Georgetown Cir, Madison, CT 06443

  Last Sold Summary

  • 5% Above List Price
  • $315/SF
  • 1 Day On Market

  Last Sold Price $947,000

  Last Listing Agent Julie Bedell Compass Connecticut, LLC
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  $815,000 Sold Jul 11, 2025

  27 Hammonassett Meadows Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Above List Price
  • $358/SF
  • 3 Days On Market

  Current Estimated Value $818,802

  Last Listing Agent Leigh Whiteman William Raveis Real Estate

  27 Hammonassett Meadows Rd, Madison, CT 06443
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  Est $855,521 Not Listed For Sale

  21 Heatherwood Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,712 Sq Ft
  • Built 1976

  21 Heatherwood Dr, Madison, CT 06443

  Last Sold Summary

  • 4% Above List Price
  • $302/SF
  • 22 Days On Market

  Last Sold Price $820,000

  Last Listing Agent Dana Weinstein Coldwell Banker Realty
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  $605,000 Sold Mar 24, 2025

  11 Aylesbury Cir, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1979

  Last Sold Summary

  • 10% Above List Price
  • $473/SF
  • 26 Days On Market

  Current Estimated Value $584,426

  Last Listing Agent Kirsten Adams William Pitt Sotheby's Int'l

  11 Aylesbury Cir, Madison, CT 06443
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  Est $1,721,917 Not Listed For Sale

  51 Buck Hill Rd, Madison, CT 06443

  • 5 Beds
  • 7 Baths
  • 4,994 Sq Ft
  • Built 2006

  51 Buck Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 8% Above List Price
  • $320/SF
  • 263 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Margaret Muir William Pitt
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  $779,000 Sold Feb 03, 2026

  13 Longview Terrace, Madison, CT 06443

  • 3 Beds
  • 3.5 Baths
  • 3,772 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Below List Price
  • $207/SF
  • 69 Days On Market

  Current Estimated Value $810,876

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

  13 Longview Terrace, Madison, CT 06443

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