34 Windward Lane
Madison, CT 06443
Madison Center
3 Beds
2.5 Baths
2,756 sqft (on 0.44 acres)
3 Beds
2.5 Baths
2,756 sqft
(on 0.44 acres)
Local Information
- Map ViewExplore the area around 34 Windward Lane.
- Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1974
Lot Size
0.44 acres
Living Area
2,756 sqft
Price/Sqft
$704
Parking
2 Car Garage
About this House
Windward by the Sea. Amazing home situated on a quiet cul-de-sac street South of the Boston Post Rd, walking distance to the Village of Madison and its beautiful sandy beaches. Remodeled by renowned builder, Skip Broom, this home displays optimum in workmanship, and materials. Perfect for entertaining. Custom kitchen with large island opens to family room with fireplace. Gracious living room with fireplace. Light and bright enclosed sun porch. Finished lower level. Perfectly landscaped lot with both a deck and a stone patio. 4-bedroom septic system so expansion may be possible.
34 Windward Lane, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,756 sqft single-family home in Madison Center, built in 1974. It last sold for $1,610,000 on Jul 25, 2023 (7% above the $1,500,000 asking price). It is currently off market. The Trulia Estimate is $1,940,400, with a rent estimate of $6,475/month.
Home Details for 34 Windward Lane
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Interior Details Basement: Full,FinishedNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Sun Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2756 Square Feet |
Appliances & Utilities Utilities: Underground UtilitiesAppliances: Gas Range, Oven, Subzero, Dishwasher, Washer, Dryer, Wine Cooler, Gas Water HeaterDishwasherDryerLaundry: Main LevelWasher |
Heating & Cooling Heating: Forced Air,Gas In StreetHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 2Has a Fireplace |
Windows, Doors, Floors & Walls Window: Thermopane Windows |
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Exterior Home Features Roof: AsphaltPatio / Porch: Porch, EnclosedExterior: Awning(s)Foundation: Concrete PerimeterNo Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Attached,Paved |
Frontage Waterfront: Water Community, Walk to WaterNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 2756 Square Feet |
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Year Built Year Built: 1974 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Clapboard, HardiPlank TypeNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 1154762 |
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Price List Price: $1,500,000 |
Status Change & Dates Off Market Date: Sun May 14 2023Possession Timing: Negiotiable |
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MLS Status: Closed |
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Direction & Address City: Madison |
School Information Elementary School: JM JeffreyJr High / Middle School: PolsonHigh School: Daniel Hand |
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Building Area Building Area: 2756 Square Feet |
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Community Features: Golf, Medical Facilities, Playground |
Other Playground |
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No HOA |
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Lot Area: 0.44 acres |
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Energy Efficiency Features: Thermostat, Windows |
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BasementMls Number: 170567826Attic: Walk-up, StorageAbove Grade Unfinished Area: 2756 |
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GolfMedical FacilitiesPlayground |
Last check for updates: about 2 hours ago
Listed by Cathy Lynch, (203) 627-2331
Coldwell Banker Realty, (203) 245-4700
Bought with: John Cuozzo, (203) 288-1900, Press/Cuozzo Realtors, (203) 288-1900
Source: Smart MLS, MLS#170567826
Price History for 34 Windward Lane
| Date | Price | Event | Source |
|---|---|---|---|
| 07/25/2023 | $1,610,000 | Sold | Smart MLS #170567826 |
| 07/10/2023 | $1,500,000 | Pending | Smart MLS #170567826 |
| 06/25/2023 | $1,500,000 | Contingent | Smart MLS #170567826 |
| 05/12/2023 | $1,500,000 | Listed For Sale | Smart MLS #170567826 |
| 10/04/2004 | $1,100,000 | Sold | Smart MLS #M9080175 |
| 07/07/2000 | $529,900 | Sold | Smart MLS #M9057807 |
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 | $23,000 |
| Assessment | $1,025,400 |
Home facts updated by county records
Comparable Sales for 34 Windward Lane
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.18 | Single-Family Home | $1,400,000 | 07/17/26 | 4 | 3 | 3,046 | |
0.28 | 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 | |
0.29 | Single-Family Home | $1,453,000 | 08/29/25 | 5 | 3.5 | 2,647 | |
0.56 | Single-Family Home | $1,927,500 | 08/19/25 | 3 | 2.5 | 2,700 | |
0.34 | Single-Family Home | $1,825,000 | 06/01/26 | 3 | 3 | 1,976 | |
0.65 | Single-Family Home | $1,710,000 | 06/10/26 | 3 | 2.5 | 2,661 | |
0.29 | Single-Family Home | $895,000 | 02/02/26 | 4 | 2.5 | 2,691 | |
0.42 | Single-Family Home | $1,045,000 | 09/26/25 | 4 | 3 | 1,891 | |
0.51 | Single-Family Home | $2,505,000 | 10/27/25 | 4 | 3.5 | 3,160 |
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Assigned Schools
These are the assigned schools for 34 Windward Lane.
- 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 34 Windward Lane.
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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