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
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Description
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.
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. This description is from July 10, 2024
Home Highlights
Parking
2 Car Garage
Outdoor
Porch
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
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 4 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 April 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
73 19MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $23,000 |
| Assessment | $1,025,400 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$4,491/mo
Comparable Sales for 34 Windward Lane
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
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 | |
0.29 | Single-Family Home | $895,000 | 02/02/26 | 4 | 2.5 | 2,691 | |
0.43 | Single-Family Home | $1,225,000 | 06/19/25 | 4 | 3 | 2,340 | |
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 | |
0.32 | Single-Family Home | $1,175,000 | 03/25/26 | 4 | 2 | 1,692 |
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Assigned Schools
These are the assigned schools for 34 Windward Lane.
- J. Milton Jeffrey Elementary School
- K-3
- Public
- 362 Students
10/10GreatSchools RatingParent Rating AverageExcellent. Jeffrey school IS the place to be!Parent Review8y ago - Daniel Hand High School
- 9-12
- Public
- 828 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
- 354 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 Review2y ago - Walter C. Polson Upper Middle School
- 6-8
- Public
- 520 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.
LGBTQ Local Legal Protections
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
34 Windward Lane, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,756 sqft single-family home built in 1974. 34 Windward Lane is located in Madison Center, Madison. This property is not currently available for sale. 34 Windward Lane was last sold on Jul 25, 2023 for $1,610,000 (7% higher than the asking price of $1,500,000). The current Trulia Estimate for 34 Windward Lane is $1,907,300.