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Back 44 Winding Road
Off Market

44 Winding Road

Madison CT 06443

4
2
2
1698 sq. ft.
1.62 ac.
Single-Family
Last sold for $405,000
Menachem MermelsteinMenachem Mermelstein, last sold this property on 16 September 2026 after 40 days on market.

Overview

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.

Features

4 bedrooms
2 bathrooms
2 carspaces
2 garage spaces
1698 sq. ft. floor area
1.62 ac. lot size
Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Madison over the last 12 months, the estimated median property value of 44 Winding Road is $855k.

Median value
$855k
Estimated value range
$300k - $3.4m
Median days on market
10
Estimated value trend
9%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Madison. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 44 Winding Road

2026
Sold
$405,000
16 Sep 2026 by Menachem Mermelstein

Happy sellers in Madison

87%
87% of sellers in Madison reported that their sale price either exceeded or met their price expectations.

Madison stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 3 reviews in Madison over the last 12 months.

Local market activity for 4 bedroom single-family properties in Madison

In the last 12 months, 103 four-bedroom single-family properties similar to 44 Winding Road, have been sold.

This represents a 4% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Madison

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Kelly Whiteman

Kelly Whiteman is a recommended agent for Madison.  They have 3 local sales and collected 2 local reviews across the last 12 months.

  •   5   (11 reviews)
  •  2 Reviews in Madison
  •  3 Sales in Madison
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Rose Ciardiello

Rose Ciardiello is a recommended agent for Madison.  They have 12 local sales and collected 1 local review across the last 12 months.

  •   5   (10 reviews)
  •  1 Review in Madison
  •  12 Sales in Madison
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Rob McConville

Rob McConville is a recommended agent for Madison.  They have 6 local sales and collected 1 local review across the last 12 months.

  •   5   (3 reviews)
  •  1 Review in Madison
  •  6 Sales in Madison
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Cathy Lynch

Cathy Lynch is a recommended agent for Madison.  They have 31 local sales across the last 12 months.

  •  31 Sales in Madison
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