44 Winding Road
Madison, CT 06443
4
Bed
2
Bath
1,698Sqft
1.62Acres(Lot)
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.
Property Details
Map
Map
What's Nearby
Nearby Areas
Features
-
Bedroom Information
Total beds: 4Bathroom Information
Total Baths: 2 Full Baths: 2Room Information
Rooms Total: 7 Has Basement: Yes Basement: Full -
Roofing Information
Shingle -
Interior Features
Roof: Shingle Appliances: Range, Oven, Refrigerator -
Heating & Cooling
Has Heating: Yes Heating: Oil, Baseboard Cooling: None
-
Building Information
Year Built: 1968 Building Area Total: 1698 Construction Materials: Vinyl Siding, Frame Private Pool: No
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Lot Information
Lot Size Acres: 1.62
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Listing Price Information
Listing Price: $400000
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Tax Information
Parcel Number: 1159705 Annual Tax: $7052
-
Parking Information
AttachedGarage Information
Has Garage: Yes Has Attached Garage: Yes Garage Space: 2
-
School Information
Elementary School: Per Board of EdJunior High School:Senior High School: Per Board of Ed -
Location Information
Direction: GPS Friendly WaterSource: Well
How much is this property worth?
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Nearby Home Value
| Address | Estimate | Bed | Bath | Sq. Ft | Lot Size |
|---|---|---|---|---|---|
| 32 North Street, Madison, CT, 06443 | $149,900 | 2 | 1 | 592 | 592 SqFt |
| 40 East Street, Madison, CT, 06443 | $235,000 | 1 | 1 | 732 | 732 SqFt |
| 92 Fourth Avenue, Madison, CT, 06443 | $142,900 | 2 | 1 | 396 | 396 SqFt |
| 16 North Street, Madison, CT, 06443 | $138,000 | 1 | 1 | 476 | 476 SqFt |
| 89-2 Cottage Road, Madison, CT, 06443 | $350,000 | 2 | 1 | 764 | 764 SqFt |
| 3 Longview Terrace #3, Madison, CT, 06443 | $925,000 | 3 | 4 | 3,234 | 3,234 SqFt |
| 44 Pent Road, Madison, CT, 06443 | $1,199,000 | 2 | 2 | 1,010 | 1,010 SqFt |
| 25 Knob Hill Road, Madison, CT, 06443 | $875,000 | 4 | 3 | 2,974 | 2,974 SqFt |
| 20 Forest Hills Drive, Madison, CT, 06443 | $739,000 | 3 | 2 | 1,913 | 1,913 SqFt |
| 141 Duck Hole Road, Madison, CT, 06443 | $550,000 | 3 | 2 | 1,186 | 1,186 SqFt |
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ByOwner last updated this listing 08/16/2026 @ 03:59
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