44 Winding Road, Madison, CT 06443 - Photo 1

1/1

$405,000

Sold
Closed
Single Family
4 Beds
2 Full Baths
1,698 Sq. Ft.
2 Car Garage
Updated 5 days ago

1/1

Property Description

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.

Full Property Details

Full Property Details for 44 Winding Rd

General

Sold For: $405,000
Taxes: (July 2026-June 2027)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24197194
Added to Site: 51 day(s) ago

Interior

Number of Rooms: 7
Appliances: Oven/Range, Refrigerator

Rooms

Bathrooms

Total Bathrooms: 2
Full Bathrooms: 2

Bedrooms

Total Bedrooms: 4
Primary Bedroom: Primary Bedroom, Main
Bedroom 1: Bedroom, Main
Bedroom 2: Bedroom, Main
Bedroom 3: Bedroom, Main

Other Rooms

Living Room: Living Room, Main
Dining Room: Dining Room, Main

Parking

Garage: Yes
Attached garage: Yes
Garage Spaces: 2
Parking: Attached Garage

Location

County: New Haven
Driving Directions: GPS Friendly

School Information

Elementary School: Per Board of Ed
High School: Per Board of Ed

Heating & Cooling

Cooling Type: None
Heating Type: Baseboard, Oil
Heating Fuel: Oil
Water Heater: 40 Gallon Tank

Utilities

Sewer: Septic
Water: Private Well

Structural Information

Architectural Style: Ranch
Construction Status: No/Resale
Exterior Const.: Vinyl Siding
Basement Desc.: Full
Roof: Shingle
Attic: Yes
Square Feet: 1,698
Above Ground: 1,698 Sq. Ft.
Year Built: 1968

Lot Features

Lot Size (Acres): 1.62
Zoning: RU-1
Lot Description: N/A

Financial Considerations

Assessment Amount: $314,400
Tax Year: July 2026-June 2027

Disclosures and Reports

Property ID: 1159705

Listed and Sold by eXp Realty, Mark Mermelstein

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Listing agent

— 44 Winding Rd —

Mark Mermelstein

eXp Realty

Agent Contact: (347) 634-2123 Office Contact: (866) 828-3951

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NMLS#: 1598647

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Schools

Schools serving 44 Winding Rd

School District:Madison School District

Name	Grades	Distance
Kathleen H. Ryerson Elementary School 982 Durham Road, Madison, CT 06443	K-3	1.1 mi
Dr. Robert H. Brown Middle School 980 Durham Road, Madison, CT 06443	4-5	1.2 mi
Walter C. Polson Upper Middle School 302 Green Hill Road, Madison, CT 06443	6-8	3.5 mi
Daniel Hand High School 286 Green Hill Road, Madison, CT 06443	9-12	3.6 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 44 Winding Rd

Date

Details

Price

Change

Source

9/16/2026

Sold

$405,000

1.25%

MLS

8/06/2026

Listed

$400,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Active
Updated 22 hours ago

3
Beds
2
Total Baths
1,622
Sq. Ft.

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Just Listed

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Updated 2 days ago

3
Beds
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Total Baths
1,431
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Just Listed

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3
Beds
2
Total Baths
1,954
Sq. Ft.

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Just Listed

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Single Family
Active
Updated 5 days ago

2
Beds
2
Total Baths
1,549
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Price Reduced

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Single Family
Active
Updated 4 days ago

4
Beds
3
Total Baths
2,151
Sq. Ft.

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Price Reduced

-$26,000 (-3.27%)

$769,000

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Single Family
Active
Updated 5 days ago

3
Beds
3
Total Baths
2,547
Sq. Ft.

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Price Reduced

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$227,500

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Active
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2
Beds
2
Total Baths
924
Sq. Ft.

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Price Reduced

-$50,000 (-10.44%)

$429,000

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Single Family
Active
Updated 2 days ago

2
Beds
2
Total Baths
1,126
Sq. Ft.

Listed by William Raveis Real Estate

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Sold

$460,000

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Single Family
Closed

4
Beds
3
Total Baths
2,024
Sq. Ft.

Listed by William Pitt Sotheby's Int'l
Sold by Whitestone Real Estate Group

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Sold

$434,000

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Single Family
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3
Beds
3
Total Baths
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Sold

$440,000

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Single Family
Closed

2
Beds
1
Total Bath
864
Sq. Ft.

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Sold

$450,000

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Townhouse
Closed

1
Bed
2
Total Baths
1,372
Sq. Ft.

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Sold by Cathy Lynch & Team

44 Winding Road, Madison, CT 06443 (MLS# 24197194) is a Single Family property that was sold at $405,000 on September 16, 2026. Want to learn more about 44 Winding Road? Do you have questions about finding other Single Family real estate for sale in Madison? You can browse all Madison real estate or contact a Coldwell Banker agent to request more information.

44 Winding Rd Madison, CT 06443