23 Windward Ln
Madison, CT 06443
Madison Center
3 Beds
2.5 Baths
2,152 sqft (on 0.57 acres)
3 Beds
2.5 Baths
2,152 sqft
(on 0.57 acres)
Local Information
- Map ViewExplore the area around 23 Windward Ln.
- Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1967
Lot Size
0.57 acres
Living Area
2,152 sqft
Price/Sqft
$672
Parking
Garage
About this House
PERFECT LOCATION. Located on a cul-de-sac off Island Ave, this home is close to water/beaches, library, book store, and downtown Madison. Original owners have lovingly cared for this home. Enjoy the updated kitchen. Living room features a wood burning fireplace while the family room has cozy gas fireplace. Dive into your in-ground pool, stay cool under the covered patio, or relax in your glass enclosed porch. Convenient outside shower. Extras include newer roof, underground sprinkler system, shed, and central air on second level. First level has ductless wall unit in kitchen/family room. Hardwood floors throughout. Gas available in the street.
DON'T SETTLE FOR LESS
DON'T SETTLE FOR LESS
23 Windward Ln, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,152 sqft single-family home in Madison Center, built in 1967. It last sold for $775,000 on Aug 10, 2018. It is currently off market. The Trulia Estimate is $1,446,400, with a rent estimate of $4,830/month.
Home Details for 23 Windward Ln
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Heating & Cooling Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood |
Interior Details AtticNumber of Rooms: 7Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Sun RoomCeiling Fan |
Appliances & Utilities Cable ReadyRefrigerator |
Fireplace & Spa Fireplace |
Security Security System |
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Exterior Home Features Roof: AsphaltExterior: Shingle, WoodGardenLawnPatioSprinkler System |
Pool Pool |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Year Built Year Built: 1967Year Updated: 2021 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Lot Area: 0.57 acres |
Price History for 23 Windward Ln
| Date | Price | Event | Source |
|---|---|---|---|
| 08/10/2018 | $775,000 | Sold | Smart MLS #170099436 |
| 06/28/2018 | $769,900 | Listed For Sale | Agent Provided |
Market trends in Madison
Last updated June 2026
Avg. sale price
$763K
Sale-to-List Price
100.7%
Price per sq ft
$327
Available listings
71
2MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $18,837 |
| Assessment | $839,800 |
Home facts updated by county records
Comparable Sales for 23 Windward Ln
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.25 | Single-Family Home | $1,186,900 | 05/08/26 | 3 | 2.5 | 1,712 | |
0.31 | Single-Family Home | $1,100,000 | 12/18/25 | 4 | 2.5 | 3,031 | |
0.30 | Single-Family Home | $895,000 | 02/02/26 | 4 | 2.5 | 2,691 | |
0.24 | Single-Family Home | $1,400,000 | 07/17/26 | 4 | 3 | 3,046 | |
0.45 | Single-Family Home | $1,045,000 | 09/26/25 | 4 | 3 | 1,891 | |
0.31 | Single-Family Home | $487,666 | 12/12/25 | 5 | 2 | 2,436 | |
0.31 | Single-Family Home | $1,825,000 | 06/01/26 | 3 | 3 | 1,976 | |
0.27 | Single-Family Home | $1,453,000 | 08/29/25 | 5 | 3.5 | 2,647 | |
0.40 | Single-Family Home | $750,000 | 05/12/26 | 6 | 3 | 2,929 | |
0.65 | Single-Family Home | $941,000 | 10/01/25 | 3 | 3 | 2,393 |
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Assigned Schools
These are the assigned schools for 23 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 23 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 23 Windward Ln
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SOLDJUL 22, 2026William Pitt Sotheby's Int'l- SOLDJUL 17, 2026William Pitt Sotheby's Int'l
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SOLDJUL 9, 2026William Raveis Real Estate
SOLDJUL 8, 2026Yellowbrick Real Estate LLC
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