4 beds1,698 sqft$236/sqft
44 Winding Rd, Madison, CT 06443
Est: $2,621/moGet pre-approved

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....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 UPDATED: 08/06/2026 06:44 PM

  1. Listed by Mark Mermelstein • eXp Realty
    P: (347)-634-2123 C: (347)-634-2123 mmerms@gmail.com

Property Details for 44 Winding Road

Status
MLS #
24197194
Days on Market
1
Taxes
$7,052 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
MLS Type
Residential
Year Built
1968
Lot Size
1.62 AC / 70,567 SF
Basement Description
Full
Direct Waterfront
No
Garages Number
2
Neighborhood
N/A
Style
Ranch
Garage Parking Info
Attached Garage
Swimming Pool
No

Location

Listing Courtesy of eXp Realty, Mark Mermelstein
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Building Information for 44 Winding Road

Stories-Year Built1968Building Size-Lot Size1.62 AC / 70,567 SF

Payment Calculator

$2,621 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,033

Property Taxes

$588

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 44 Winding Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: GPS Friendly
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.340376
  • Longitude: -72.646714
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $7,052
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator
  • Attic Description: Access Via Hatch
  • Cooling System: None
  • Heat Type: Baseboard
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Rooms Total: 7
Room 1
  • Room Entry Order: 1
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Main
  • Room Type: Bedroom
Room 5
  • Listing Key: 5855443476AAAF4CE063E201100A4C79
  • Room Entry Order: 5
  • Room Level: Main
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Level: Main
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Shingle
  • Year Built: 1968
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 1698
Lot Information
  • Lot Description: N/A
  • Parcel Number: 1159705
  • Sq Ft Est Heated Above Grade: 1698.0
  • Sq Ft Total: 1698.0
  • Zoning: RU-1
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: 40 Gallon Tank
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 44 Winding Road

DateEvent & SourcePriceAppreciation
Feb 18, 2009

Closed (Public Record)

Public Record #764109848

$310,000
Feb 18, 2009

Closed (Public Record)

Public Record #264109848

$310,000

+3.9% / yr

Apr 27, 1993

Closed (Public Record)

Public Record #92240740

$170,000
DateEvent & SourcePrice
02/18/2009

Closed (Public Record)

Public Record #764109848

$310,000
02/18/2009

Closed (Public Record)

Public Record #264109848

$310,000

+3.9% / yr

04/27/1993

Closed (Public Record)

Public Record #92240740

$170,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 44 Winding Road

Taxable ValueLand$123,300Additions$191,100Total$314,400
Tax Record2025$7,052 ($588 / month)
Home Facts
Beds4Baths2Total Finished SqFt1,698 SqFtAbove Grade Finished SqFt1,698 SqFtStories1Lot Size70,567 SqFtStyleSingle Family ResidenceYear Built1968Year Renovated1968ZoningRU-1CountySOUTH CENTRAL CONNECTICUAPNMADI M:115 B:39

Schools near 44 Winding Road

This home is within Madison School District.
Rating
School
Type
Grades
Distance
Public - 4 to 5
Public - 6 to 8
Public - 9 to 12
Public - K to 4
Rating
School
Distance
Dr. Robert H. Brown Middle School
Public4 to 5

Walter C. Polson Upper Middle School
Public6 to 8

Daniel Hand High School
Public9 to 12

Island Avenue Elementary School
PublicK to 4

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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44 Winding Road is a single family home for sale in Madison, CT 06443. This listing's school district is Madison School District. Nearby schools include Dr. Robert H. Brown Middle School, Walter C. Polson Upper Middle School and Daniel Hand High School. 44 Winding Road is a 4-bed, 2-bath, 1,698 sqft single family home built in 1968.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of eXp Realty, Mark Mermelstein

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.