19 Windward Ln, Madison, CT 06443
OFF MARKET

$1,453,800

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,910 sqft (on 0.51 acres)

19 Windward Ln, Madison, CT 06443

Madison Center
Est. Refi. Payment $10,083/mo*
Refinance Your Home

Home Value

Trulia Estimate
$1.45M
Since last month
Decreased$7K (-0.5%)
Since last year
Increased$45K (+3.2%)
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 +72% in the last 10 years
MonthEstimated value
2026
August 2026$1.46M
July 2026$1.46M
June 2026$1.48M
May 2026$1.45M
April 2026$1.4M
March 2026$1.39M
February 2026$1.37M
January 2026$1.36M
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
513 Boston Post Road, Madison, CT
0.33
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031
55 Island Avenue, Madison, CT
0.25
Single-Family Home
$1,400,000
07/17/26
4
3
3,046
519 Boston Post Road, Madison, CT
0.33
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
24 Cherry Lane, Madison, CT
0.27
Single-Family Home
$1,186,900
05/08/26
3
2.5
1,712
39 Madison Avenue, Madison, CT
0.44
Single-Family Home
$1,045,000
09/26/25
4
3
1,891
73 Middle Beach Rd W, Madison, CT
0.30
Single-Family Home
$487,666
12/12/25
5
2
2,436
49 Middle Beach Rd, Madison, CT
0.39
Single-Family Home
$750,000
05/12/26
6
3
2,929
81A Middle Beach Road, Madison, CT
0.47
Single-Family Home
$2,495,000
08/17/26
4
2.5
3,321
11 Middle Beach Road, Madison, CT
0.29
Single-Family Home
$1,825,000
06/01/26
3
3
1,976
52 East Wharf Road, Madison, CT
0.63
Single-Family Home
$1,940,000
08/17/26
5
3
2,920

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
15 Windward Lane, Madison, CT 06443
0.03
$1,682,700
4
3.5
2,704
Off Market
10 Middle Beach Road West, Madison, CT 06443
0.07
$3,775,000
6
6
6,074
Recently Sold
24 Windward Lane, Madison, CT 06443
0.05
$1,779,800
3
3.5
3,628
Off Market
14 Middle Beach Road West, Madison, CT 06443
0.12
$4,499,000
6
6.5
5,817
For Sale
34 Windward Lane, Madison, CT 06443
0.08
$1,921,400
3
2.5
2,756
Off Market
3 Sunset Road, Madison, CT 06443
0.13
$1,272,100
3
2.5
1,980
Off Market
79 Island Avenue, Madison, CT 06443
0.13
$2,254,500
4
3.5
3,741
Off Market
11 Sunset Road, Madison, CT 06443
0.17
$1,324,300
3
3
2,186
Off Market
85 Island Avenue, Madison, CT 06443
0.17
$2,352,600
5
4.5
4,472
Off Market
57 Island Avenue, Madison, CT 06443
0.20
$1,667,700
4
3.5
3,006
Off Market
57 West Wharf Road, Madison, CT 06443
0.25
$1,806,100
4
3.5
2,772
Off Market
63 West Wharf Road, Madison, CT 06443
0.25
$1,307,400
3
3
2,051
Off Market

Local Information

  • Map ViewExplore the area around 19 Windward Ln.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1972
Lot Size
0.51 acres
Living Area
2,910 sqft
Price/Sqft
$500

About this House

This single-family home is located at 19 Windward Ln, Madison, CT. 19 Windward Ln is in the Madison Center neighborhood in Madison, CT and in ZIP code 06443. This property has 4 bedrooms, 3 bathrooms and approximately 2,910 sqft of floor space. This property has a lot size of 0.51 acres and was built in 1972.
19 Windward Ln, Madison, CT 06443 is a 4 bedroom, 3 bathroom, 2,910 sqft single-family home in Madison Center, built in 1972. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,453,800, with a rent estimate of $5,563/month.

Home Details for 19 Windward Ln

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1972
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 0.51 acres

Price and Tax history

YearProperty taxTax assessment
2025
$19,332
$861,900
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

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Frequently asked questions about 19 Windward Ln

  • What is 19 Windward Ln estimated to be worth?
    Trulia's estimated value for 19 Windward Ln in Madison, CT is $1,453,800.
  • 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 19 Windward Ln?
    The closest schools to 19 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 19 Windward Ln?
    The lot at 19 Windward Ln in Madison, CT is about 0.51 acres (22,215 sq ft).

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