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44 Winding Road, 
Madison, CT 06443

$400,000

4

Beds

2

Baths

1,698

Sq Ft

Single Family

Pending

Listed by

Mark Mermelstein, (347) 634-2123

eXp Realty, (866) 828-3951

(866) 828-3951

Last updated:

August 25, 2026, 07:52 AM

MLS#

24197194

Source:

CT

About This Home

44 Winding Road

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.

Home Facts

Single Family

2 Baths

4 Bedrooms

Built in 1968

Price Summary

400,000

$235 per Sq. Ft.

MLS #:

24197194

Last Updated:

August 25, 2026, 07:52 AM

Added:

19 day(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

1,698 Sq. Ft.

Structure

Structure

Architectural Style:

Ranch

Building Area:

1,698 Sq. Ft.

Year Built:

1968

Lot

Lot Size (Sq. Ft):

70,567

Finances & Disclosures

Finances

Price:

$400,000

Price per Sq. Ft:

$235 per Sq. Ft.

Source:CT
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.