Madison, CT Homes

• 

  Est $594,433

  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
• 

  

  

  /40

  $2,675,000

  Coming Soon

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

  373 Boston Post Rd, Madison, CT 06443

  Set back and sited high on a hill overlooking 1.6 aces of estate-like grounds with seasonal views of Long Island Sound and Madison Country Club's 18-hole golf course, this residence was constructed by one of the town's most esteemed builders as his own home, and it shows in every detail. Nine-foot ceilings and abundant light define the first floor, which includes a living/dining room and elegant

  Margaret Muir William Pitt Sotheby's Int'l

  373 Boston Post Rd, 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 $1,006,118

  Last Listing Agent Greg robbins Houlihan Lawrence WD

  166 Bishop Ln, Madison, CT 06443
• 

  Est $666,277

  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.
• 

  

  

  /37

  $1,080,000

  Open Sun 1:30PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 2,208 Sq Ft

  15 Cambridge Dr, Madison, CT 06443

  Introducing 15 Cambridge Drive, an exceptional Madison Townhouse style Condo in the heart of it all. Accessible, yet private this residence is a rare find. Tucked away at the end of Cambridge Dr, right off Island Ave this 2,200+ square foot townhouse is an unexpected combination of polished elegance, charm and thoughtfulness in renovation and design. The sophisticated Living and Dining room are

  Phoebe Schreiner William Pitt Sotheby's Int'l

  15 Cambridge Dr, 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 $561,835

  Last Listing Agent Jaime Lettieri Coldwell Banker Realty

  3 Essex Ln Unit 3, Madison, CT 06443
• 

  Est $728,816

  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
• 

  

  /38

  $999,000

  $201K PRICE DROP

  • 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
• 

  $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 $1,207,427

  Last Listing Agent Rose Ciardiello William Raveis Real Estate

  11 Tuxis Rd, Madison, CT 06443
• 

  Est $676,192

  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
• 

  

  /9

  $1,235,000

  • Land
  • 1.02 Acres
  • $1,210,784 per Acre

  8 Old Route 79, Madison, CT 06443

  Great commercial lot - signalize corner, level and cleared. A rare opportunity for Developers and Investors. Located at the strategic Junction of Old route 79 and Durham Road . One minute to I-95. The property boasts exceptional visibility an accessibility from both north and southbound traffic. Short distance to downtown MADISON, this site is ideal for a variety of commercial ventures, including

  Thomas Simjian Keller Williams Coastal

  8 Old Route 79, 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 $647,686

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

  7 Derenthal Dr, Madison, CT 06443
• 

  Est $822,495

  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
• 

  

  /38

  $3,000,000

  $1M PRICE DROP

  • 5 Beds
  • 6 Baths
  • 5,657 Sq Ft

  45 Island Ave, Madison, CT 06443

  Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight

  Meig Walz Newcomb Coldwell Banker Realty

  45 Island Ave, Madison, CT 06443
• 

  $575,000

  Sold Sep 01, 2026

  141 Duck Hole Rd, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 1,186 Sq Ft
  • Built 1914

  Last Sold Summary

  • 5% Above List Price
  • $485/SF
  • 43 Days On Market

  Current Estimated Value $542,072

  Last Listing Agent Meig Walz Newcomb Coldwell Banker Realty

  141 Duck Hole Rd, Madison, CT 06443
• 

  Est $969,517

  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.
• 

  

  /34

  $735,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,614 Sq Ft

  450 County Rd, Madison, CT 06443

  DESIRABLE 4 BEDROOM NORTH MADISON HOME. Nestled on 2.62 peaceful, tree-lined acres in desirable North Madison, this classic yellow Colonial combines timeless New England charm with spacious, modern comfort. Offering 2,600+ square feet of beautifully appointed living space, the four-bedroom, 2.5 bath home is anchored by rich hardwood floors throughout the home. The front Living Room is spacious,

  Kirsten Adams William Pitt Sotheby's Int'l

  450 County 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 $917,729

  Last Listing Agent Dylan Walter William Raveis Real Estate

  23 Horsebarn Ln, Madison, CT 06443
• 

  Est $680,270

  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
• 

  

  /32

  $449,000

  Under Contract

  • 1 Bed
  • 1.5 Baths
  • 1,944 Sq Ft

  5 W Sussex Place Unit 5, Madison, CT 06443

  End-unit townhouse condominium in Madison, Connecticut - open-concept living,attached garage, plus a finished lower level! Built in 2006 at West Sussex Place, this move-in ready home features hardwood floors, a kitchen with granite countertops and stainless steel appliances, and a light-filled living and dining area on the main level. Primary bedroom, Loft (or 2nd bed) and the full bath are on

  Jules Gaughran - Etes William Pitt Sotheby's Int'l

  5 W Sussex Place Unit 5, 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 $520,359

  Last Listing Agent Suzanne McConville William Raveis Real Estate

  1 Wilshire Rd Unit B, Madison, CT 06443
• 

  Est $501,623

  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

  $755,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,317 Sq Ft

  44 Sterling Park, Madison, CT 06443

  Move right into this meticulously maintained home, proudly offered for sale for the very first time by its original owners. This distinctive contemporary 3-bedroom home welcomes you with an inviting natural setting surrounded by mature trees, charming stone walls, and striking rock outcroppings. Inside, abundant natural light fills the thoughtfully designed living spaces, including a formal

  Joanne Combs Dan Combs Real Estate

  44 Sterling Park, Madison, CT 06443
• 

  $220,000

  Sold Jul 01, 2026

  26 North St, Madison, CT 06443

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

  Last Sold Summary

  • 12% Below List Price
  • $340/SF
  • 84 Days On Market

  Last Listing Agent Karen Floriano William Raveis Real Estate

  26 North St, Madison, CT 06443
• 

  Est $665,961

  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
• 

  

  /12

  $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
• 

  $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 $1,776,170

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

  11 Middle Beach Rd, Madison, CT 06443
• 

  Est $613,986

  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

  $849,000

  Open Sun 11AM - 12:30PM Coming Soon Pre-Foreclosure

  • 4 Beds
  • 3 Baths
  • 2,792 Sq Ft

  150 Race Hill Rd, Madison, CT 06443

  A rare and remarkably charming Antique in one of Madison's most picturesque settings. Set on 7+ acres along quiet Race Hill Rd, this beautifully preserved circa-1764 Cape blends centuries of character with thoughtful updates and the ease of modern living. Originally restored to the studs in 1996, the 2,091 sq.ft. main house retains an extraordinary amount of its original character, including

  Phoebe Schreiner William Pitt Sotheby's Int'l

  150 Race Hill Rd, Madison, CT 06443
• 

  $503,000

  Sold Jan 30, 2026

  43 Fort Path Rd, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 1,346 Sq Ft
  • Built 1960

  Last Sold Summary

  • 7% Below List Price
  • $374/SF
  • 40 Days On Market

  Current Estimated Value $535,755

  Last Listing Agent Lisa Rollins Team Compass Connecticut, LLC

  43 Fort Path Rd, Madison, CT 06443
• 

  Est $568,135

  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
• 

  

  /40

  $635,000

  Open Sat 11AM - 1PM $30K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,604 Sq Ft

  81 Legend Hill Rd Unit 81, Madison, CT 06443

  Rarely available, this unit is the largest size Townhouse ("Model D") at Legend Hill. It benefits from a quiet location in the complex away from the main road. This unit has been well maintained with excellent natural light and updated neutral decor. Since purchasing, these owners have installed all new flooring throughout first level, in addition to new carpets on second level. Also recently

  Carol Mancini William Pitt Sotheby's Int'l

  81 Legend Hill Rd Unit 81, Madison, CT 06443
• 

  $725,000

  Sold Dec 01, 2025

  129 Acorn Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $269/SF
  • 103 Days On Market

  Current Estimated Value $779,204

  Last Listing Agent Ann Stewart William Pitt Sotheby's Int'l

  129 Acorn Rd, Madison, CT 06443
• 

  Est $552,446

  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
• 

  $795,000

  Sold Jul 15, 2026

  45 Milano Pond Dr, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft
  • Built 1991

  Last Sold Summary

  • 10% Above List Price
  • $417/SF
  • 37 Days On Market

  Current Estimated Value $773,721

  Last Listing Agent Rob McConville RE/MAX Heritage

  45 Milano Pond Dr, Madison, CT 06443
• 

  Est $650,051

  Not Listed For Sale

  263 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1987

  263 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 15 Days On Market

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

  $825,000

  Sold May 14, 2026

  40 Hull Rd, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 3,462 Sq Ft
  • Built 1963

  Last Sold Summary

  • $238/SF
  • 62 Days On Market

  Current Estimated Value $829,471

  Last Listing Agent Sue Woods William Pitt Sotheby's Int'l

  40 Hull Rd, Madison, CT 06443
• 

  Est $594,734

  Not Listed For Sale

  279 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 4 Baths
  • 2,476 Sq Ft
  • Built 1985

  279 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 81 Days On Market

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

  $1,665,000

  Sold Jul 07, 2026

  34 Wildcat Springs Dr, Madison, CT 06443

  • 5 Beds
  • 5.5 Baths
  • 5,380 Sq Ft
  • Built 1981

  Last Sold Summary

  • 11% Above List Price
  • $309/SF
  • 15 Days On Market

  Current Estimated Value $1,456,710

  Last Listing Agent Rebecca Ellsley Higgins Group Bedford Square

  34 Wildcat Springs Dr, Madison, CT 06443
• 

  Est $581,486

  Not Listed For Sale

  75 Legend Hill Rd, Madison, CT 06443

  • 2 Beds
  • 3 Baths
  • 2,140 Sq Ft
  • Built 1985

  75 Legend Hill Rd, Madison, CT 06443

  Last Sold Summary

  • 3 Days On Market

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

Showing Results 241 - 280, Page 7 of 18