Madison, CT Homes

• 

  $141,500

  Sold Sep 20, 2025

  20 Young's Village, Madison, CT 06443

  • 1 Bed
  • 1 Bath
  • 410 Sq Ft
  • Built 1950

  Last Sold Summary

  • 9% Below List Price
  • $345/SF
  • 54 Days On Market

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

  20 Young's Village, Madison, CT 06443
• 

  Est $624,890

  Not Listed For Sale

  119 Squires Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 1,624 Sq Ft
  • Built 1972

  119 Squires Rd, Madison, CT 06443

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent George Sznaj DB Associates of CT, LLC
• 

  

  

  /39

  $475,000

  Pending

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

  20 Centre Village Dr Unit 20, Madison, CT 06443

  Enjoy easy, low-maintenance condo living in one of Madison's most desirable locations, just steps from the Town Green, downtown shops, restaurants, and beaches. Tucked within a small, well-maintained complex of only 22 units, this light-filled home offers an open floor plan enhanced by soaring vaulted ceilings, skylights, oversized windows, and beautiful hardwood and tile flooring throughout. The

  Rose Ciardiello William Raveis Real Estate

  20 Centre Village Dr Unit 20, Madison, CT 06443
• 

  $815,000

  Sold Mar 26, 2026

  16 Forest Hills Dr, Madison, CT 06443

  • 5 Beds
  • 3 Baths
  • 3,992 Sq Ft
  • Built 1965

  Last Sold Summary

  • 7% Below List Price
  • $204/SF
  • 160 Days On Market

  Current Estimated Value $870,658

  Last Listing Agent Rod Cross Coldwell Banker Realty

  16 Forest Hills Dr, Madison, CT 06443
• 

  Est $583,789

  Not Listed For Sale

  83 Squires Rd, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 2,200 Sq Ft
  • Built 1969

  83 Squires Rd, Madison, CT 06443

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Stacey Wyeth William Pitt Sotheby's Int'l
• 

  

  /12

  $1,375,000

  New Construction 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
• 

  $725,000

  Sold Apr 09, 2026

  21 Little Hollow Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,589 Sq Ft
  • Built 1977

  Last Sold Summary

  • 1% Above List Price
  • $456/SF
  • 14 Days On Market

  Current Estimated Value $716,362

  Last Listing Agent Cathy Lynch Coldwell Banker Realty

  21 Little Hollow Rd, Madison, CT 06443
• 

  Est $641,502

  Not Listed For Sale

  57 Squires Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,324 Sq Ft
  • Built 1970

  57 Squires Rd, Madison, CT 06443

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Linda Talmadge Berkshire Hathaway NE Prop.
• 

  

  /24

  $565,000

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

  29 Wilshire Rd Unit 29, Madison, CT 06443

  Experience true WIDE OPEN SPACES in highly sought-after Kensington Acres South! With condos, it is all about LOCATION. This desirable completely detached standalone Ranch is not attached along the corners like some other units. Flooded w/ bright natural light, the home boasts peaceful, expansive lawn views from your private enclosed Sun Room, a perfect spot for morning coffee. A flat, level &

  Todd Gould William Pitt Sotheby's Int'l

  29 Wilshire Rd Unit 29, Madison, CT 06443
• 

  $670,000

  Sold Aug 21, 2025

  5 Dover Ln, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,096 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Above List Price
  • $320/SF
  • 97 Days On Market

  Current Estimated Value $698,562

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

  5 Dover Ln, Madison, CT 06443
• 

  Est $713,839

  Not Listed For Sale

  37 Squires Rd, Madison, CT 06443

  • 3 Beds
  • 3.5 Baths
  • 2,636 Sq Ft
  • Built 1970

  37 Squires Rd, Madison, CT 06443

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Patsy Metcalf Compass Connecticut, LLC
• 

  

  /40

  $2,800,000

  Pending

  • 4 Beds
  • 6 Baths
  • 4,854 Sq Ft

  85 Garnet Park Rd, Madison, CT 06443

  A home that captures you-and doesn't let go. Nestled along the quiet edge of the Neck River, this is one of those rare offerings where design, setting and detail immediately leave an impression. From the moment you arrive, the front porch sets the tone for what unfolds beyond it. Inside, every space feels considered. A true designer's home where nothing is overlooked and nothing is left to

  Nicole White William Raveis Real Estate

  85 Garnet Park Rd, Madison, CT 06443
• 

  $660,000

  Sold May 04, 2026

  19 Green Acres Dr, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 1,903 Sq Ft
  • Built 1957

  Last Sold Summary

  • 7% Above List Price
  • $347/SF
  • 5 Days On Market

  Current Estimated Value $646,351

  Last Listing Agent Amy Kirst William Pitt Sotheby's Int'l

  19 Green Acres Dr, Madison, CT 06443
• 

  Est $643,563

  Not Listed For Sale

  93 Race Hill Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,604 Sq Ft
  • Built 1987

  93 Race Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 73 Days On Market

  Last Listing Agent Heather Dacey William Raveis Real Estate
• 

  

  /38

  $899,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,303 Sq Ft

  98 Bishop Ln, Madison, CT 06443

  Set gracefully on a beautifully landscaped property framed by classic New England stone walls, this timeless Colonial has been thoughtfully refreshed and offers the perfect balance of warmth, charm, and modern comfort. A welcoming covered front porch opens an inviting interior with a classic, smart floor plan. At the heart of the home is the Kitchen featuring honed granite, GE Monogram stainless

  Phoebe Schreiner William Pitt Sotheby's Int'l

  98 Bishop Ln, Madison, CT 06443
• 

  $343,000

  Sold Jan 16, 2026

  20C Yankee Glen Rd Unit 20C, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1979

  Last Sold Summary

  • 11% Below List Price
  • $307/SF
  • 95 Days On Market

  Current Estimated Value $428,013

  Last Listing Agent Dallas Davis Dalvis Realty

  20C Yankee Glen Rd Unit 20C, Madison, CT 06443
• 

  Est $842,352

  Not Listed For Sale

  68 Old Toll Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,753 Sq Ft
  • Built 1999

  68 Old Toll Rd, Madison, CT 06443

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent David Mayhew Pearce Real Estate
• 

  

  /40

  $1,950,000

  $300K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,160 Sq Ft

  26 Bassett Ln, Madison, CT 06443

  Completely rebuilt and expanded in 2026, this custom coastal home with deeded beach rights is located in Madison's charming Seafields Association. Thoughtfully designed with designer details throughout, the home provides elevated shoreline living with glimpses of Long Island Sound, state-of-the-art appliances, high-end finishes, a bright, open layout, mudroom, butler's pantry with laundry, and a

  Steven Koleno Beycome of Connecticut

  26 Bassett Ln, Madison, CT 06443
• 

  $900,000

  Sold Nov 14, 2025

  166 Bishop Ln, Madison, CT 06443

  • 3 Beds
  • 3 Baths
  • 2,968 Sq Ft
  • Built 1983

  Last Sold Summary

  • 6% Above List Price
  • $303/SF
  • 27 Days On Market

  Current Estimated Value $984,038

  Last Listing Agent Greg robbins Houlihan Lawrence WD

  166 Bishop Ln, Madison, CT 06443
• 

  Est $947,268

  Not Listed For Sale

  177 Concord Dr, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 3,004 Sq Ft
  • Built 2015

  177 Concord Dr, Madison, CT 06443

  Last Sold Summary

  • 41 Days On Market

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

  

  /22

  $749,000

  • Land
  • 8,276 Sq Ft
  • $3,942,105 per Acre

  885 Boston Post Rd, Madison, CT 06443

  Fully approved and ready to go, this exceptional commercial lot is situated in the heart of vibrant downtown Madison. Boasting approvals for a 5,000 square foot building the property includes a brand-new septic system, 13 designated parking spaces with additional parking options, and unbeatable proximity to restaurants, shopping, the train station, and I-95. Imagine welcoming clients or customers

  Michael Hvizdo Coldwell Banker Realty

  885 Boston Post Rd, Madison, CT 06443
• 

  $565,000

  Sold Jan 20, 2026

  3 Essex Ln Unit 3, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1977

  Last Sold Summary

  • 1% Below List Price
  • $441/SF
  • 50 Days On Market

  Current Estimated Value $558,192

  Last Listing Agent Jaime Lettieri Coldwell Banker Realty

  3 Essex Ln Unit 3, Madison, CT 06443
• 

  Est $672,318

  Not Listed For Sale

  53 Heatherwood Dr, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,129 Sq Ft
  • Built 1977

  53 Heatherwood Dr, Madison, CT 06443

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Cathy Lynch Coldwell Banker Realty
• 

  /2

  $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
• 

  $1,175,000

  Sold Mar 25, 2026

  11 Tuxis Rd, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft
  • Built 1900

  Last Sold Summary

  • $694/SF
  • 10 Days On Market

  Current Estimated Value $1,197,870

  Last Listing Agent Rose Ciardiello William Raveis Real Estate

  11 Tuxis Rd, Madison, CT 06443
• 

  Est $486,606

  Not Listed For Sale

  309 Summer Hill Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Built 1968

  309 Summer Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Allison Bonito William Pitt Sotheby's Int'l
• 

  

  /33

  $570,000

  Open Sun 1PM - 3PM $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,476 Sq Ft

  28 Downing Way Unit 28, Madison, CT 06443

  Nicely updated 1476 sf condo with family room, plus 3 season sunporch and full basement. Largest style at Windermere. Living room and dining room are open and have nice hardwood floors. The home has all new windows! Newer kitchen with maple cabinetry. Cozy family room with fireplace opens to a 3 season porch. Off the sunporch is a private patio. There are 2 good sized bedrooms and 2 lovely newer

  Judy Libby Berkshire Hathaway NE Prop.

  28 Downing Way Unit 28, Madison, CT 06443
• 

  $960,000

  Sold Aug 29, 2025

  659 Summer Hill Rd, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,558 Sq Ft
  • Built 1779

  Last Sold Summary

  • 3% Below List Price
  • $375/SF
  • 49 Days On Market

  Current Estimated Value $986,650

  Last Listing Agent Leigh Whiteman William Raveis Real Estate

  659 Summer Hill Rd, Madison, CT 06443
• 

  Est $663,765

  Not Listed For Sale

  307 Summer Hill Rd, Madison, CT 06443

  • 4 Beds
  • 3.5 Baths
  • 3,261 Sq Ft
  • Built 1980

  307 Summer Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Jennifer Trautman Turton William Pitt Sotheby's Int'l
• 

  

  /35

  $615,000

  Pending

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

  15 Hampshire Rd Unit 15, Madison, CT 06443

  One-level living at its best. A pristine two-bedroom residence situated directly across from beautiful Hummer's Pond in one of Madison's most conveniently located communities. Just moments from the beach, town center, and all town amenities, this peaceful home is ideal as a full-time residence or a weekend retreat. Freshly painted throughout, the home features an updated kitchen that opens to the

  Susan Malan William Pitt Sotheby's Int'l

  15 Hampshire Rd Unit 15, Madison, CT 06443
• 

  $640,000

  Sold Nov 04, 2025

  7 Derenthal Dr, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Built 1966

  Last Sold Summary

  • 8% Below List Price
  • $338/SF
  • 126 Days On Market

  Current Estimated Value $643,394

  Last Listing Agent Susan Warner-Lambert Carbutti & Co., Realtors

  7 Derenthal Dr, Madison, CT 06443
• 

  Est $606,890

  Not Listed For Sale

  1065 Durham Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 1,764 Sq Ft
  • Built 1973

  1065 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Donald Schilder Houlihan Lawrence WD
• 

  

  /40

  $2,150,000

  • 4 Beds
  • 2 Baths
  • 2,251 Sq Ft

  153 Middle Beach Rd, Madison, CT 06443

  Rare opportunity to own a Nantucket-style coastal retreat on coveted Middle Beach Road in Madison. Just moments from East Wharf Beach and downtown, this distinctive property offers timeless shoreline charm, a huge porch, breathtaking tidal marsh views, and glimpses of Long Island Sound from the second floor. Filled with character and reminiscent of a 1920s seaside cottage, the sun-filled main

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  153 Middle Beach Rd, Madison, CT 06443
• 

  $855,000

  Sold Feb 02, 2026

  23 Horsebarn Ln, Madison, CT 06443

  • 4 Beds
  • 4 Baths
  • 3,972 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 105 Days On Market

  Current Estimated Value $890,144

  Last Listing Agent Dylan Walter William Raveis Real Estate

  23 Horsebarn Ln, Madison, CT 06443
• 

  Est $573,149

  Not Listed For Sale

  46 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • Built 1987

  46 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Meg Farmer RE/MAX Heritage
• 

  

  /38

  $1,200,000

  • 5 Beds
  • 5.5 Baths
  • 3,832 Sq Ft

  1209 Durham Rd, Madison, CT 06443

  Private.Pastoral.Purposeful. Available for the first time in decades. This rare 4-acre compound offers a Farmhouse style home, a guest house, 3-car garage with additional storage, and attached in-home gym, office equipped with bathroom, and artist's studio. This legacy property delivers both on location and acreage offering a one-of-a-kind sequestered compound that simply cannot be replicated.

  Heather Clinton Berkshire Hathaway NE Prop.

  1209 Durham Rd, Madison, CT 06443
• 

  $520,000

  Sold May 15, 2026

  1 Wilshire Rd Unit B, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 1,296 Sq Ft
  • Built 1974

  Last Sold Summary

  • $401/SF
  • 2 Days On Market

  Current Estimated Value $520,995

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  1 Wilshire Rd Unit B, Madison, CT 06443
• 

  Est $564,438

  Not Listed For Sale

  32 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 1,877 Sq Ft
  • Built 1985

  32 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Jane Cardarelli William Raveis Real Estate
• 

  

  /34

  $550,000

  Coming Soon

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

  12 Essex Ln, Madison, CT 06443

  Coming Soon! Goes Live August 14th! Schedule your private showing today - before it's too late! Welcome to Unit 12 at Kensington North Condominium, a 2 bedroom, 2 bathroom, well-maintained residence at 12 Essex Lane that balances quality updates with a practical layout. This end unit backs up to private open space, offering seclusion and tranquility. The interior features hardwood floors

  Lisa Rollins Team Compass Connecticut, LLC

  12 Essex Ln, Madison, CT 06443
• 

  $1,825,000

  Sold Jun 01, 2026

  11 Middle Beach Rd, Madison, CT 06443

  • 3 Beds
  • 3 Baths
  • 1,976 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Above List Price
  • $924/SF
  • 2 Days On Market

  Current Estimated Value $1,727,994

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

  11 Middle Beach Rd, Madison, CT 06443

Showing Results 241 - 280, Page 7 of 18