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44 Winding Road, Madison, CT 06443

Single Family For Sale

$400,000
$236/sqft
44 Winding Road, Madison, CT
Active
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4
Bedrooms
2
Bathrooms
1,698
Sq Ft
1.62
Acres
1968
Year Built

About This Home

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.

Listed by Mark Mermelstein (347) 634-2123 with eXp Realty (866) 828-3951

Listing Snapshot

Price $400,000 Days on Our Site 0 days
Property Tax $7,052/yr Style Ranch
Year Built 1968 Total Sq Ft 1,698
Lot Size 1.62 acres HOA Fees N/A
Bedrooms 4 Full Bathrooms 2
Total Rooms 7 Half Baths 0

Key Features

Appliances
  • Oven/Range
  • Refrigerator

Structure & Parking

Construction Frame
Roof Shingle
Garage Spaces 2
Garage Type Attached Garage

Systems & Utilities

Heat Baseboard
Fuel Oil
Cooling None
Hot Water 40 Gallon Tank
Water Private Well
Sewer Septic

Schools

Elem Per Board of Ed
High Per Board of Ed

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $588/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Aug 6, 2026 Listed $400,000

Frequently Asked Questions

How much does 44 Winding Road in Madison, CT cost?
This property is listed at $400,000, which works out to $236 per square foot.
How many bedrooms does 44 Winding Road have?
This home has 4 bedrooms and 2 bathrooms.
What is the square footage of 44 Winding Road?
The home is 1,698 square feet, situated on 1.62 acres.
When was 44 Winding Road in Madison built?
This property was built in 1968.
Is 44 Winding Road, Madison, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 44 Winding Road, Madison in?
This home is served by the Madison public school system, with Per Board of Ed as the elementary school and Per Board of Ed as the high school.
How do I schedule a tour of 44 Winding Road, Madison, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Mark Mermelstein · (347) 634-2123

eXp Realty · (866) 828-3951

MLS# 24197194 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Aug 6, 2026 6:44 PM UTC