20 Windward Ln
Madison, CT 06443
Madison Center
3 Beds
3 Baths
3,174 sqft (on 0.41 acres)
3 Beds
3 Baths
3,174 sqft
(on 0.41 acres)
Local Information
- Map ViewExplore the area around 20 Windward Ln.
- Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Description
This single-family home is located at 20 Windward Ln, Madison, CT. 20 Windward Ln is in the Madison Center neighborhood in Madison, CT and in ZIP code 06443. This property has 3 bedrooms, 3 bathrooms and approximately 3,174 sqft of floor space. This property has a lot size of 0.41 acres and was built in 1979.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 20 Windward Ln
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Heating & Cooling Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2 |
Interior Details Number of Rooms: 8 |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: AsphaltExterior: Wood |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1979 |
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional |
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Lot Area: 0.41 acres |
Price History for 20 Windward Ln
| Date | Price | Event | Source |
|---|---|---|---|
| 07/10/1998 | $388,000 | Sold | N/A |
Market trends in Madison
Last updated May 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
69
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $19,884 |
| Assessment | $886,500 |
Home facts updated by county records
Comparable Sales for 20 Windward Ln
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.34 | Single-Family Home | $487,666 | 12/12/25 | 5 | 2 | 2,436 | |
0.30 | Single-Family Home | $1,186,900 | 05/08/26 | 3 | 2.5 | 1,712 | |
0.35 | Single-Family Home | $1,100,000 | 12/18/25 | 4 | 2.5 | 3,031 | |
0.36 | Single-Family Home | $750,000 | 05/12/26 | 6 | 3 | 2,929 | |
0.34 | Single-Family Home | $895,000 | 02/02/26 | 4 | 2.5 | 2,691 | |
0.40 | Single-Family Home | $1,045,000 | 09/26/25 | 4 | 3 | 1,891 | |
0.28 | Single-Family Home | $1,825,000 | 06/01/26 | 3 | 3 | 1,976 | |
0.31 | Single-Family Home | $1,453,000 | 08/29/25 | 5 | 3.5 | 2,647 | |
0.58 | Single-Family Home | $1,927,500 | 08/19/25 | 3 | 2.5 | 2,700 | |
0.65 | Single-Family Home | $1,710,000 | 06/10/26 | 3 | 2.5 | 2,661 |
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Assigned Schools
These are the assigned schools for 20 Windward Ln.
- J. Milton Jeffrey Elementary School
- K-3
- Public
- 407 Students
10/10GreatSchools RatingParent Rating AverageExcellent. Jeffrey school IS the place to be!Parent Review8y ago - Daniel Hand High School
- 9-12
- Public
- 751 Students
10/10GreatSchools RatingParent Rating AverageI feel very unsafe when in the presence of many school administrators. I wouldn’t wish the experience I’ve had here on my worst enemy. I feel constantly harassed by some teachers but more namely the school administrators, including the Vice principal. Every day I try to come in with a positive attitude about this place, but someone has to ruin it. There are however some teachers that do a great job teaching and making everyone feel safe, but the negatives outweigh this way too much.Student Review1y ago - Dr. Robert H. Brown Middle School
- 4-5
- Public
- 361 Students
9/10GreatSchools RatingParent Rating AverageThe school is great. The teachers help you as much as they can and they want you to have as much fun as possible. At the end of every trimester some related arts classes let parents come to the school to watch there kid (in Xylorythems, Theater arts, Music and Art.) There is some bullying but you can quicky report if someone is bullying you and they will quickly handle it.Student Review3y ago - Walter C. Polson Upper Middle School
- 6-8
- Public
- 541 Students
9/10GreatSchools RatingParent Rating AverageMy kids are currently attending Polson MS and are receiving an excellent education that is preparing them for high school and beyond. The course work is challenging and homework is not lacking, however, the teachers are readily available to the students for extra help before and after school. But even with all the hard work the school has great spirit and the kids have fun either in sports, theater, music or what ever their area of interest is. The schools drew us to Madison and the location has kept us! GREAT TOWN! I believe the parent involvement in the school system is a primary driver for why the school system is so successful.Parent Review14y ago 
Check out schools near 20 Windward Ln.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Madison Center
At least 1 Trulia users voted on each feature.
100 % Say it's walkable to grocery stores
100 % Say it's walkable to restaurants
100 % Say it's dog friendly
100 % Say there's wildlife
100 % Say neighbors are friendly
50 % Say there are community events
50 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
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Off Market Homes Near 20 Windward Ln
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SOLDJUN 15, 2026William Pitt Sotheby's Int'l- See more homes for sale inMadison
20 Windward Ln, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 3,174 sqft single-family home built in 1979. 20 Windward Ln is located in Madison Center, Madison. This property is not currently available for sale. 20 Windward Ln was last sold on Jul 10, 1998 for $388,000. The current Trulia Estimate for 20 Windward Ln is $1,453,000.