Madison, CT Homes

• 

  

  

  /37

  $1,150,000

  • 4 Beds
  • 2.5 Baths
  • 4,019 Sq Ft

  86 Quail Run, Madison, CT 06443

  Mark your calendars! Showings begin on Thursday, May 7th. Welcome home to this beautifully designed 4-bedroom Colonial offering space, style, and an exceptional floor plan! Step into the impressive two-story foyer with elegant marble tile floors that set the tone for what's to come. The formal living room flows seamlessly into a sun-filled family room featuring a charming bay window, vaulted

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  86 Quail Run, Madison, CT 06443
• 

  

  

  /39

  $3,400 Per Month

  • 4 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • House for Rent

  32 Bassett Ln, Madison, CT 06443

  AVAILABLE FROM EARLY SEPTEMBER 2026 TO END OF MAY 2027! Welcome to this enchanting 4 bedroom, 2 full bath home, where the beach is just a half-block stroll away! Located off Neck Road, 1 mile from the heart of Madison, CT, this residence offers the perfect blend of coastal charm and convenience. As you enter, the first floor greets you with a Family Room, through to a Kitchen, then onto the

  Kirsten Adams William Pitt Sotheby's Int'l

  32 Bassett Ln, Madison, CT 06443
• 

  $628,000 Sold Oct 24, 2025

  338 Opening Hill Rd, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 1,792 Sq Ft
  • Built 1968

  Last Sold Summary

  • 7% Above List Price
  • $350/SF
  • 34 Days On Market

  Current Estimated Value $622,005

  Last Listing Agent Barbara Goetsch William Pitt Sotheby's Int'l

  338 Opening Hill Rd, Madison, CT 06443
• 

  Est $463,447 Not Listed For Sale

  31 Samantha Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 2,055 Sq Ft
  • Built 1998

  31 Samantha Ln, Madison, CT 06443

  Last Sold Summary

  • 16% Above List Price
  • $195/SF
  • 2 Days On Market

  • Last Sold Price $400,000
  • Oct 27, 2023

  Last Listing Agent John Campbell Compass Connecticut, LLC
• 

  

  

  /37

  $925,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,976 Sq Ft

  85 Fawn Brook Cir, Madison, CT 06443

  A Shoreline Masterpiece: Custom Cape Cod Living on 1.10 Private Acres Welcome to 85 Fawn Brook Circle, an immaculate Cape Cod retreat nestled at the end of a quiet, picturesque cul-de-sac. This 4-bedroom, with a first floor primary suite; 2.5-bathroom home has been thoughtfully reimagined with a level of detail rarely seen. Rich hardwood floors flow through every room, complemented by crisp

  Colette Harron William Pitt Sotheby's Int'l

  85 Fawn Brook Cir, Madison, CT 06443
• 

  

  /23

  $7,000 Per Month

  • 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 for academic rent September 7th 2026 through mid June 2027 at 7K per month. JULY and AUGUST of 2027 is $35,000 PER MONTH. 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
• 

  $725,000 Sold Aug 25, 2025

  23 Paper Mill Dr, Madison, CT 06443

  • 5 Beds
  • 2.5 Baths
  • 2,323 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Above List Price
  • $312/SF
  • 61 Days On Market

  Current Estimated Value $740,390

  Last Listing Agent Dana Weinstein Coldwell Banker Realty

  23 Paper Mill Dr, Madison, CT 06443
• 

  Est $433,668 Not Listed For Sale

  12 Samantha Ln, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 2,108 Sq Ft
  • Built 1996

  12 Samantha Ln, Madison, CT 06443

  Last Sold Summary

  • 29% Above List Price
  • $159/SF
  • 44 Days On Market

  • Last Sold Price $335,700
  • Jul 10, 2023

  Last Listing Agent Heidi DeRusso Coldwell Banker Realty
• 

  

  /40

  $1,275,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 4,910 Sq Ft

  11 Kachina Way, Madison, CT 06443

  Welcome to 11 Kachina Way. A meticulously maintained 4 BR, 2.1 BA, handsome colonial in one of Madison's most desirable neighborhoods. Minutes from Madison schools, beaches and convenient to town centers and commuter routes. Almost 4,000 sq ft of living space, plus an additional 1,100 sq ft of finished bsmt, this lovely home has ample space for all of your needs. The 1st floor is ideal for

  Alison Gould Gould Group LLC

  11 Kachina Way, Madison, CT 06443
• 

  

  /23

  $2,900 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,684 Sq Ft
  • House for Rent

  52 Overshores E, Madison, CT 06443

  FURNISHED RENTAL AVAILABLE - September 15, 2026 to May 31, 2027. Comfortable and nicely decorated, this home has 2 bedrooms upstairs that share a newer renovated full bath. This home is located in a private association with access to the Overshores Beach, one of the nicest association beaches on Neck Road. Recently renovated kitchen, newer mud room, newer first floor full bath, laundry room on

  Kirsten Adams William Pitt Sotheby's Int'l

  52 Overshores E, Madison, CT 06443
• 

  $475,000 Sold Sep 03, 2025

  24 Deepwood Dr, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Above List Price
  • $396/SF
  • 27 Days On Market

  Current Estimated Value $471,967

  Last Listing Agent Carol Mancini William Pitt Sotheby's Int'l

  24 Deepwood Dr, Madison, CT 06443
• 

  Est $423,893 Not Listed For Sale

  4 Stephanie Ct, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1996

  4 Stephanie Ct, Madison, CT 06443

  Last Sold Summary

  • 26% Above List Price
  • $254/SF
  • 24 Days On Market

  • Last Sold Price $335,700
  • Apr 12, 2024

  Last Listing Agent Shoreline Homes Team William Raveis Real Estate
• 

  

  /19

  $899,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,642 Sq Ft

  111 Acorn Rd, Madison, CT 06443

  This impeccably maintained Colonial blends timeless charm with modern sophistication, ideally situated in a desirable family neighborhood on a quiet street just minutes from downtown Madison, scenic walking trails, beaches, and the train station. Nestled on a private lot with a serene backyard setting, the home offers exceptional comfort, style, and everyday livability. The centerpiece of the

  Meig Walz Newcomb Coldwell Banker Realty

  111 Acorn Rd, Madison, CT 06443
• 

  

  /35

  $11,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,065 Sq Ft
  • House for Rent

  33 Grove Ave, Madison, CT 06443

  FULLY FURNISHED SUMMER RENTAL. Dates available 6/29-7/31. Four bedroom colonial just steps from Seaview Beach, a private association beach! Fully furnished, internet is available, TV in 3 rooms. Hardwood floors throughout. Sunroom at back of house, along with a wraparound porch with views of Long Island Sound. Kayak in the photos is available for tenants to use during their stay as well as paddle

  Robert Curry Pearce Real Estate

  33 Grove Ave, Madison, CT 06443
• 

  $1,585,000 Sold Aug 22, 2025

  61 Governors Way, Madison, CT 06443

  • 4 Beds
  • 5 Baths
  • 6,010 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Above List Price
  • $264/SF
  • 73 Days On Market

  Current Estimated Value $1,666,460

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

  61 Governors Way, Madison, CT 06443
• 

  Est $445,343 Not Listed For Sale

  2270 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 1,916 Sq Ft
  • Built 2000

  2270 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • $232/SF
  • 63 Days On Market

  • Last Sold Price $444,000
  • Nov 22, 2024

  Last Listing Agent Linda Toscano Coldwell Banker Realty
• 

  

  /36

  $1,175,000 Under Contract

  • 5 Beds
  • 4.5 Baths
  • 3,194 Sq Ft

  37 Lovers Ln, Madison, CT 06443

  Location, Location, Location!! Timeless elegance meets modern living in this beautifully appointed 5-bedroom Colonial, ideally situated just moments from Madison's beaches and charming town green. Thoughtfully designed for both refined living and effortless entertaining, the home offers expansive gathering spaces, gracious proportions, and seamless indoor-outdoor flow. Inside, sun-filled living

  Melanie Scull William Pitt Sotheby's Int'l

  37 Lovers Ln, Madison, CT 06443
• 

  

  /18

  $5,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft
  • House for Rent

  2203 Durham Rd, Madison, CT 06443

  JULY &/OR AUGUST ~ Enjoy One or Two Months in Madison for 2026 at a Price you can't beat !! Summers in Madison are what they're cracked up to be !! Spend your Days one of 3 Local Manicured Sandy Beaches (East Wharf, West Wharf or the Surf Club) all located Directly on Long Island Sound. When the day is done, head Back Home for the Tranquility of this Country Cape on a Private and Secluded

  Tom Clancy William Pitt Sotheby's Int'l

  2203 Durham Rd, Madison, CT 06443
• 

  $530,000 Sold Oct 17, 2025

  9 Madrina Ln, Madison, CT 06443

  • 3 Beds
  • 2 Baths
  • 2,159 Sq Ft
  • Built 1975

  Last Sold Summary

  • 8% Below List Price
  • $245/SF
  • 83 Days On Market

  Current Estimated Value $546,622

  Last Listing Agent Rose Ciardiello William Raveis Real Estate

  9 Madrina Ln, Madison, CT 06443
• 

  Est $454,061 Not Listed For Sale

  26 Tibbals Bridge Rd, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1997

  26 Tibbals Bridge Rd, Madison, CT 06443

  Last Sold Summary

  • 1% Above List Price
  • $358/SF
  • 63 Days On Market

  • Last Sold Price $450,000
  • Aug 30, 2024

  Last Listing Agent David Cretella Coldwell Banker Realty
• 

  

  /40

  $699,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,627 Sq Ft

  258 Opening Hill Rd, Madison, CT 06443

  Beautifully renovated 4 bedroom, 2.5 bath Colonial set on 1.28 private acres in the highly desirable Madison community. The main level of this home offers two spacious and versatile living areas, a formal dining room, an open-concept kitchen with granite countertops and stainless steel appliances, plus a bright four-season sunroom filled with natural light. A convenient half bath completes the

  Gillian Conlin Seabury Hill REALTORS

  258 Opening Hill Rd, Madison, CT 06443
• 

  

  /34

  $12,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,382 Sq Ft
  • House for Rent

  509 Boston Post Rd, Madison, CT 06443

  Sneak away from the hustle and bustle and spend the month of August at Captain Eber Judd House (circa 1740). This historical gem, reminiscent of Nantucket and Essex Whaling Captain's homes, oozes charm with its stunning wide plank floors, beams, and original fireplaces. Located in the heart of downtown Madison, it's just steps from the gorgeous beach, the quintessential downtown, and the Friday

  Phoebe Schreiner William Pitt Sotheby's Int'l

  509 Boston Post Rd, Madison, CT 06443
• 

  $1,230,000 Sold Jul 02, 2025

  66 Beekman Place, Madison, CT 06443

  • 4 Beds
  • 2.5 Baths
  • 4,203 Sq Ft
  • Built 1991

  Last Sold Summary

  • 12% Above List Price
  • $293/SF
  • 17 Days On Market

  Current Estimated Value $1,256,950

  Last Listing Agent Lisa Daniele William Raveis Real Estate

  66 Beekman Place, Madison, CT 06443
• 

  Est $443,595 Not Listed For Sale

  17 Jasper Ln, Madison, CT 06443

  • 2 Beds
  • 2 Baths
  • 2,177 Sq Ft
  • Built 1993

  17 Jasper Ln, Madison, CT 06443

  Last Sold Summary

  • 6% Above List Price
  • $193/SF
  • 151 Days On Market

  • Last Sold Price $420,000
  • Mar 20, 2024

  Last Listing Agent Jules Gaughran - Etes William Pitt
• 

  

  /21

  $729,500 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  96 Winterhill Rd, Madison, CT 06443

  Beautiful home with fully finished basement, hardwood on main and upper levels, CAir, kitchen with new cabinets and granite counters, new windows and siding in 2021, newly tiled lower level 2021, new front sidewalk 2021.

  Bonnie Fillion Berkshire Hathaway NE Prop.

  96 Winterhill Rd, Madison, CT 06443
• 

  

  /39

  $15,000 Per Month

  • 4 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • House for Rent

  147 Overshores W, Madison, CT 06443

  WATERVIEW SUMMER RENTAL AVAILABLE FOR JULY ONLY as August is now rented. This quintessential Seasonal Beach Cottage with WATER VIEWS is special The views out over Long Island Sound AND a wonderful wraparound South facing Open Porch to catch the summer breezes are both part of this charming Cottage, located directly across from the very desirable private Overshore (SANDY) Beach Association with

  Todd Gould William Pitt Sotheby's Int'l

  147 Overshores W, Madison, CT 06443
• 

  $475,000 Sold Sep 05, 2025

  108 Sandlewood Dr, Madison, CT 06443

  • 3 Beds
  • 3 Baths
  • 2,640 Sq Ft
  • Built 1968

  Last Sold Summary

  • 14% Below List Price
  • $180/SF
  • 72 Days On Market

  Current Estimated Value $500,507

  Last Listing Agent Jennifer Bordonaro William Pitt Sotheby's Int'l

  108 Sandlewood Dr, Madison, CT 06443
• 

  Est $487,272 Not Listed For Sale

  2313 Durham Rd, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 2,336 Sq Ft
  • Built 1940

  2313 Durham Rd, Madison, CT 06443

  Last Sold Summary

  • 27% Above List Price
  • $165/SF
  • 41 Days On Market

  • Last Sold Price $385,000
  • Jul 21, 2023

  Last Listing Agent Emily Lovejoy William Raveis Real Estate
• 

  

  /40

  $3,950,000 Pending

  • 6 Beds
  • 7 Baths
  • 6,074 Sq Ft

  10 Middle Beach Rd W, Madison, CT 06443

  PRIVATE AND PEACEFUL WITH DEEDED BEACH ACCESS! Panoramic views of LI Sound are enjoyed from almost every room of this gracious,very private home with ample room for family & lucky guests. Sited back from Middle Beach Road West and overlooking the ever changing salt marsh, enter the inviting double height foyer to discover spacious, high ceilinged and light filled rooms that are throughout the

  Margaret Muir William Pitt Sotheby's Int'l

  10 Middle Beach Rd W, Madison, CT 06443
• 

  

  /28

  $45,000 Per Month

  • 7 Beds
  • 7 Baths
  • 5,075 Sq Ft
  • House for Rent

  118 Middle Beach Rd, Madison, CT 06443

  Daydreaming about waking up to the sounds of waves and walking to your very own private beach? Make your dreams come true at 118 Middle Beach Road! With 7 bedrooms, 5 full baths, and 2 half baths, this iconic property comfortably accommodates up to 14 guests. The main level is an entertainer's paradise featuring an oversized kitchen, formal dining area, living room with views from every angle,

  Melanie Abbott William Pitt Sotheby's Int'l

  118 Middle Beach Rd, Madison, CT 06443
• 

  $510,000 Sold Jul 03, 2025

  1201 Durham Rd, Madison, CT 06443

  • 3 Beds
  • 1.5 Baths
  • 1,649 Sq Ft
  • Built 1976

  Last Sold Summary

  • 15% Below List Price
  • $309/SF
  • 47 Days On Market

  Current Estimated Value $535,082

  Last Listing Agent Mike 'Mr. Z' Zerbini IMT Realty

  1201 Durham Rd, Madison, CT 06443
• 

  Est $1,202,986 Not Listed For Sale

  217 Devonshire Ln, Madison, CT 06443

  • 4 Beds
  • 6 Baths
  • 5,865 Sq Ft
  • Built 2001

  217 Devonshire Ln, Madison, CT 06443

  Last Sold Summary

  • 7% Below List Price
  • $222/SF
  • 41 Days On Market

  • Last Sold Price $1,300,000
  • Mar 25, 2024

  Last Listing Agent Phoebe Schreiner William Pitt
• 

  

  /5

  $900,000

  • Land
  • 2.42 Acres
  • $371,901 per Acre

  0 Mill Rd, Madison, CT 06443

  A RARE & VERSATILE REAL ESTATE OPPORTUNITY! For a limited time, discover this truly unique 2.42 acre corner parcel that perfectly balances natural beauty with massive investment potential. Featuring a picturesque mix of mature trees & diverse topography, the land offers a slight, wooded hill on one end (ideal for an elevated, private homesite) and a sweeping flat open area on the other. A classic

  Todd Gould William Pitt Sotheby's Int'l

  0 Mill Rd, Madison, CT 06443
• 

  $960,000 Sold Jun 30, 2025

  218 Neck Rd, Madison, CT 06443

  • 4 Beds
  • 2 Baths
  • 2,047 Sq Ft
  • Built 1967

  Last Sold Summary

  • 4% Above List Price
  • $469/SF
  • 6 Days On Market

  Current Estimated Value $1,017,743

  Last Listing Agent Michelle Drobot Coldwell Banker Realty

  218 Neck Rd, Madison, CT 06443
• 

  Est $714,453 Not Listed For Sale

  98 Dorset Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 3,607 Sq Ft
  • Built 1994

  98 Dorset Ln, Madison, CT 06443

  Last Sold Summary

  • 8% Above List Price
  • $184/SF
  • 36 Days On Market

  • Last Sold Price $662,500
  • Apr 23, 2024

  Last Listing Agent Antonio Stella eXp Realty
• 

  

  /24

  $499,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,746 Sq Ft

  12 Sportsman Hill Rd, Madison, CT 06443

  4 Bedroom 2.5 Bath traditional Colonial, 1 car attached garage on quiet road near town and beaches. Solid home, Dry. Roof is 13 years old. Investors and flippers and DIY's this one is for you! Hot Madison Market! Full unfinished walk out basement.Raised Hearth Fireplace in Family room, and Raised Hearth fireplace in Living Room with Built ins alongside. Terrific location as house is set back

  Steve Adkins Berkshire Hathaway NE Prop.

  12 Sportsman Hill Rd, Madison, CT 06443
• 

  $543,800 Sold May 21, 2025

  6 Apple Way, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 1,932 Sq Ft
  • Built 1994

  Last Sold Summary

  • 5% Below List Price
  • $281/SF
  • 179 Days On Market

  Current Estimated Value $599,249

  Last Listing Agent Julie Ovian William Pitt Sotheby's Int'l

  6 Apple Way, Madison, CT 06443
• 

  Est $693,150 Not Listed For Sale

  201 Dorset Ln, Madison, CT 06443

  • 3 Beds
  • 2.5 Baths
  • 3,156 Sq Ft
  • Built 1994

  201 Dorset Ln, Madison, CT 06443

  Last Sold Summary

  • 7% Above List Price
  • $206/SF
  • 67 Days On Market

  • Last Sold Price $650,000
  • Jul 08, 2024

  Last Listing Agent Christina King Connecticut Real Estate Group LLC
• 

  

  /36

  $499,999

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

  3 Sandgate Cir, Madison, CT 06443

  Welcome to this 1,853 sq. ft. townhouse in desirable Windermere. A five-minute drive will take you to the center of town, where one will find a variety of specialty stores, as well as the famous local bookstore, where a leisurely lunch can be enjoyed in its cafe. The Library, several restaurants, a cinema, where classic films are shown, are also popular attractions. During the warmer months, it

  Doris Fallon William Raveis Real Estate

  3 Sandgate Cir, Madison, CT 06443
• 

  $860,000 Sold Mar 02, 2026

  100 Concord Dr, Madison, CT 06443

  • 4 Beds
  • 3 Baths
  • 3,517 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Above List Price
  • $245/SF
  • 40 Days On Market

  Current Estimated Value $846,108

  Last Listing Agent Amanda Popplewell-Sanson Coldwell Banker Realty

  100 Concord Dr, Madison, CT 06443

Showing Results 81 - 120, Page 3 of 18