41 Windward Ln, Madison, CT 06443
OFF MARKET

41 Windward Ln
Madison, CT 06443

Madison Center
  • 5 Beds
  • 5 Baths
  • 3,336 sqft (on 0.78 acres)

$1,604,700

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $11,130/mo*
Refinance Your Home

$1,604,700

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $11,130/mo*
Refinance Your Home
5 Beds
5 Baths
3,336 sqft
(on 0.78 acres)

Home Value

Trulia Estimate
$1.6M
Since last month
Increased$18K (+1.2%)
Since last year
Decreased$1K (-0.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +64% in the last 10 years
MonthEstimated value
2026
August 2026$1.6M
July 2026$1.58M
June 2026$1.71M
May 2026$1.68M
April 2026$1.59M
March 2026$1.57M
February 2026$1.55M
January 2026$1.55M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
55 Island Avenue, Madison, CT
0.21
Single-Family Home
$1,400,000
07/17/26
4
3
3,046
32 Park Ave, Madison, CT
0.38
Single-Family Home
$146,000
06/01/26
5
5
5,472
519 Boston Post Road, Madison, CT
0.22
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
584 Boston Post Road, Madison, CT
0.26
Single-Family Home
$1,525,000
10/01/25
5
5.5
6,278
513 Boston Post Road, Madison, CT
0.24
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031
20 Cherry Lane, Madison, CT
0.23
Single-Family Home
$1,453,000
08/29/25
5
3.5
2,647
10 Middle Beach Road West, Madison, CT
0.17
Single-Family Home
$3,775,000
05/19/26
6
6
6,074
52 East Wharf Road, Madison, CT
0.61
Single-Family Home
$1,940,000
08/17/26
5
3
2,920
36 Cedar Lane, Madison, CT
0.37
Single-Family Home
$2,310,000
07/15/26
4
4
3,926
395 Boston Post Road, Madison, CT
0.68
Single-Family Home
$1,400,000
05/01/26
4
5
3,779

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
34 Windward Lane, Madison, CT 06443
0.07
$1,938,300
3
2.5
2,756
Off Market
24 Windward Lane, Madison, CT 06443
0.10
$1,786,000
3
3.5
3,628
Off Market
15 Windward Lane, Madison, CT 06443
0.14
$1,696,800
4
3.5
2,704
Off Market
10 Middle Beach Road West, Madison, CT 06443
0.17
$3,775,000
6
6
6,074
Recently Sold
79 Island Avenue, Madison, CT 06443
0.18
$2,256,200
4
3.5
3,741
Off Market
24 Cherry Lane, Madison, CT 06443
0.22
$1,186,900
3
2.5
1,712
Recently Sold
57 Island Avenue, Madison, CT 06443
0.19
$1,679,100
4
3.5
3,006
Off Market
20 Cherry Lane, Madison, CT 06443
0.23
$1,676,500
5
3.5
2,647
Off Market
3 Sunset Road, Madison, CT 06443
0.20
$1,272,100
3
2.5
1,980
Off Market
45 Island Avenue, Madison, CT 06443
0.20
$3,495,000
5
5
5,657
For Sale
519 Boston Post Road, Madison, CT 06443
0.22
$895,000
4
2.5
2,691
Recently Sold
55 Island Avenue, Madison, CT 06443
0.21
$1,400,000
4
3
3,046
Recently Sold

Local Information

  • Map ViewExplore the area around 41 Windward Ln.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1976
Lot Size
0.78 acres
Living Area
3,336 sqft
Price/Sqft
$481

About this House

This single-family home is located at 41 Windward Ln, Madison, CT. 41 Windward Ln is in the Madison Center neighborhood in Madison, CT and in ZIP code 06443. This property has 5 bedrooms, 5 bathrooms and approximately 3,336 sqft of floor space. This property has a lot size of 0.78 acres and was built in 1976.
41 Windward Ln, Madison, CT 06443 is a 5 bedroom, 5 bathroom, 3,336 sqft single-family home in Madison Center, built in 1976. It is currently off market. The Trulia Estimate is $1,604,700, with a rent estimate of $5,889/month.

Home Details for 41 Windward Ln

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 10

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other

Property Information

Year Built
Year Built: 1976
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Lot Information

Lot Area: 0.78 acres

Price and Tax history

YearProperty taxTax assessment
2025
$22,269
$992,800
Home facts updated by county records

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$710K
$53.67KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$334
$7MoM
Available listings
63
8MoM

Around this home

Neighborhood Overview

Madison Center
See Local Highlights
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.
  • Nancy Bussiere
    "My commute to work is under 15mins. I love the easy access to highways. There is public transportation available but I haven’t used it as of yet"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 41 Windward Ln

  • What is 41 Windward Ln estimated to be worth?
    Trulia's estimated value for 41 Windward Ln in Madison, CT is $1,604,700.
  • Is Madison a buyer's or seller's market?
    Madison is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $710K. That is down $53.67K from the prior month.
  • What are the closest schools to 41 Windward Ln?
    The closest schools to 41 Windward Ln in Madison, CT are Daniel Hand High School (rated 10/10), Dr. Robert H. Brown Middle School (Elementary, rated 9/10), J. Milton Jeffrey Elementary School (rated 10/10).
  • How big is the lot at 41 Windward Ln?
    The lot at 41 Windward Ln in Madison, CT is about 0.78 acres (33,976 sq ft).

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