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16 Properties Available
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$2,295,000
Single Family Home
23 Sheep Pasture Road, Madison, CT 06443
Built by a highly regarded shoreline builder known for uncompromising attention to detail, this residence is designed fo...
Listed by Jillian Wollman of Wollman Realty
$2,290,000
Single Family Home
92 Scotland Avenue, Madison, CT 06443
Less than one mile from downtown Madison, this new construction home offers refined living with white oak floors, custom...
Listed by Jillian Wollman of Wollman Realty
$210,000
Single Family Home
40 East Street, Madison, CT 06443
Enjoy the best the shoreline has to offer in this charming seasonal summer cottage. Bring your swimsuits, sunscreen, and...
Listed by Marissa McCue of William Pitt Sotheby's Int'l
$569,000
Single Family Home
25 Samantha Lane, Madison, CT 06443
Nicely maintained 3-bedroom, 3-full-bath home nestled in a quaint cul-de-sac setting. The home is in very good condition...
Listed by Dee Hasuly of KW Legacy Partners
$450,000
Condo
12 West Sussex Place #12, Madison, CT 06443
Welcome to effortless, low-maintenance living in this beautifully maintained 2-bedroom, 1.5-bath condominium, built in 2...
Listed by Mark McElrath of William Pitt Sotheby's Int'l
$3,950
Single Family Home
153 Middle Beach Road, Madison, CT 06443
Spend your summer by the shore at 153 Middle Beach Road in Madison, a classic coastal retreat available for an academic ...
Listed by Sheila Tinn Murphy of Berkshire Hathaway NE Prop.
$574,000
Condo
250 Legend Hill Road #250, Madison, CT 06443
Welcome to 250 Legend Hill Road, a beautifully maintained townhouse condominium in Madison's sought-after Legend Hill co...
Listed by Kelly Whiteman of William Raveis Real Estate
$635,000
Condo
81 Legend Hill Road #81, Madison, CT 06443
Rarely available, this unit is the largest size Townhouse ("Model D") at Legend Hill. It benefits from a quiet location ...
Listed by Carol Mancini of William Pitt Sotheby's Int'l
$3,500
Single Family Home
1091 Boston Post Road, Madison, CT 06443
ANNUAL UNFURNISHED RENTAL, AVAILABLE IMMEDIATELY. Located between downtown Madison and the Hammonasset State Park Beach,...
Listed by Kirsten Adams of William Pitt Sotheby's Int'l
$880,000
Single Family Home
2415 Durham Road, Madison, CT 06443
Turn down a long, picturesque driveway to a stunning mid-century cape, unseen from the roadway. Note, the spectacular fi...
Listed by Debra Thomas of Sette Real Estate LLC
$2,500
Single Family Home
153 Middle Beach Road, Madison, CT 06443
Spend your summer by the shore at 153 Middle Beach Road in Madison, a classic coastal retreat available for August 2026 ...
Listed by Sheila Tinn Murphy of Berkshire Hathaway NE Prop.
$1,950,000
Single Family Home
26 Bassett Lane, Madison, CT 06443
Completely rebuilt and expanded in 2026, this custom coastal home with deeded beach rights is located in Madison's charm...
Listed by Steven Koleno of Beycome of Connecticut
$149,900
Single Family Home
32 North Street, Madison, CT 06443
With a new roof in process, 32 North Street is calling you home! Set on one of the largest lots in Dud's Village, this l...
Listed by Mel Abbott of William Pitt Sotheby's Int'l
$455,000
Condo
6 Ladshaw Drive #6, Madison, CT 06443
Privacy & convenience are both found within this updated detached stand-alone Ranch home in sought after Kensington Acre...
Listed by Greg Robbins of Houlihan Lawrence WD
$45,000
Single Family Home
118 Middle Beach Road, Madison, CT 06443
Daydreaming about waking up to the sounds of waves and walking to your very own private beach? Make your dreams come tru...
Listed by Mel Abbott of William Pitt Sotheby's Int'l
$3,000
Single Family Home
43 Neck Road, Madison, CT 06443
Annual Furnished Rental. Nestled in the heart of one of Madison's most sought-after beach communities, this charming and...
Listed by Phoebe Finch of William Pitt Sotheby's Int'l
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