Situated on 1.62 acres, this 4-bedroom, 2-bath ranch offers endless potential for investors, contractors, or buyers looking to create their dream home. The expansive backyard, once used as a sports field, provides an incredible amount of usable outdoor space that’s rarely found. Inside, you’ll find hardwood floors in many rooms, a spacious living room with a fireplace, a 2-car attached garage, and a bright sunroom/family room just off the kitchen featuring walls of windows overlooking the backyard. The home does require significant updating and repairs, but the layout, lot, and location provide an exceptional opportunity to add value. Conveniently located close to downtown shops, restaurants, and commuter routes.
Listing Provided Courtesy of Mark Mermelstein at eXp Realty
Property Details
Price:
$400,000
MLS #:
24197194
Status:
Active
Beds:
4
Baths:
2
Type:
Single Family
Neighborhood:
na
Listed Date:
Aug 6, 2026
Finished Sq Ft:
1,698
Lot Size:
70,567 sqft / 1.62 acres (approx)
Year Built:
1968
See this Listing
Schools
Elementary School:
Per Board of Ed
High School:
Per Board of Ed
Interior
Exterior
Financial
Map
Community
- Address44 Winding Madison CT
- NeighborhoodN/A
- CityMadison
- CountyNew Haven
- Zip Code06443
Subdivisions in Madison
Market Summary
Current real estate data for Single Family in Madison as of Aug 08, 2026
71
Single Family Listed
129
Avg DOM
461
Avg $ / SqFt
$1,268,861
Avg List Price
Property Summary
- 44 Winding Madison CT is a Single Family for sale in Madison, CT, 06443. It is listed for $400,000 and features 4 beds, 2 baths, and has approximately 1,698 square feet of living space, and was originally constructed in 1968. The current price per square foot is $236. The average price per square foot for Single Family listings in Madison is $461. The average listing price for Single Family in Madison is $1,268,861. To schedule a showing of MLS#24197194 at 44 Winding in Madison, CT, contact your Century 21 AllPoints Realty agent at (203) 802-7252.
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44 Winding
Madison, CT