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$400,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,698 Sq. Ft.
  • 2 Car Garage
  • Updated 13 hours ago
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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 for 44 Winding Rd

General

  • Price: $400,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24197194
  • Updated: 8/6/2026
  • Added to Site: 1 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 2025-June 2026

Disclosures and Reports

  • Property ID: 1159705

Listed 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

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 44 Winding Rd

School District:Madison School District
NameGradesDistance
Kathleen H. Ryerson Elementary School
982 Durham Road, Madison, CT 06443
K-31.1 mi
Dr. Robert H. Brown Middle School
980 Durham Road, Madison, CT 06443
4-51.2 mi
Walter C. Polson Upper Middle School
302 Green Hill Road, Madison, CT 06443
6-83.5 mi
Daniel Hand High School
286 Green Hill Road, Madison, CT 06443
9-123.6 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/06/2026
Listed
$400,000
29.03%
MLS
2/18/2009
Sold
$310,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 44 Winding Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,052
2%
$314,400
—
2023
$6,917
12%
$314,400
53%
2023
$6,150
2%
$205,200
—
2022
$6,035
2%
$205,200
—
2021
$5,920
2%
$205,200
—
2020
$5,817
—
$205,200
—
2019
$5,817
2%
$205,200
1%
2018
$5,706
3%
$203,500
—
2017
$5,556
3%
$203,500
—
2016
$5,391
3%
$203,500
—
2015
$5,242
2%
$203,500
—
2014
$5,122
-3%
$203,500
-22%
2013
$5,287
—
$259,300
—
2010
$5,287
—
$259,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by eXp Realty, Mark Mermelstein

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44 Winding Road, Madison, CT 06443 (MLS# 24197194) is a Single Family property with 4 bedrooms and 2 full bathrooms. 44 Winding Road is currently listed for $400,000 and was received on August 06, 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.

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