44 Winding Road
Madison, Connecticut 06443
- Beds
- 4
- Baths
- 2
- SqFt
- 1,698
- Acres
- 1.62
- Year Built
- 1968
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
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.
Key Facts
- City/Town
- Madison
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch
- Year Built
- 1968
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,698 sq ft
- Lot Size
- 1.62 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,052 / Annually
Market Snapshot
The Madison Market
Single Family · trailing 12 months
Active Listings
28
45 under contract
Median List Price
$1.30M
28 active listings
Median Closed Price
$730,000
221 sales
Median Days on Market
54
28 active listings
Median $ / Sq Ft
$500
28 active listings
Sale-to-List Ratio
100.0%
221 sales
How this home compares
List Price
$400,000
vs $1.30M median
69.2% below median
Price / Sq Ft
$236
vs $500 median
52.8% below median
Days on Market
0 days
vs 54 days median
54 days fresher than median
Based on 28 active and 221 closed sales (trailing 12 mo) of single family in Madison. Source: SmartMLS · As of August 6, 2026.
Location
44 Winding Road, Madison, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 30, 2026per month
- Principal & Interest$2,056
- Property Taxes$588
- Insurance$133
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Madison
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1968
- New Construction
- No/Resale
- Living Area
- 1,698 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- Oil
- Cooling
- None
- Appliances
- Oven/RangeRefrigerator
- Basement
- Full
Exterior & Lot
- Lot Size
- 1.62 acres
- Zoning
- RU-1
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Shingle
- Foundation
- Concrete
- Lot Description
- N/A
Listing & Financials
- Property Taxes
- $7,052 / Annually
- Days on Market
- 0
- MLS #
- 24197194
- MLS Status
- Active
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/6/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 8/6/2026 at 11:20 PM UTC.