42 Windward Ln, Madison, CT 06443
Property image
Property image
OFF MARKET

$1,755,100

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,255 sqft (on 0.54 acres)

42 Windward Ln, Madison, CT 06443

Madison Center
Refinance Your Home
Currently Off Market - Sold Jun 9, 2017 for $865,000

Home Value

Trulia Estimate
$1.75M
Since last month
Increased$34K (+2%)
Since last year
Increased$22K (+1.3%)
Since last sale
Increased$895K (+103.5%)
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 +101% in the last 10 years
MonthEstimated value
2026
August 2026$1.76M
August 2026$1.75M
July 2026$1.73M
June 2026$1.86M
May 2026$1.81M
April 2026$1.74M
March 2026$1.68M
February 2026$1.67M
January 2026$1.66M
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
0.26
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031
519 Boston Post Road, Madison, CT
0.24
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
55 Island Avenue, Madison, CT
0.17
Single-Family Home
$1,400,000
07/17/26
4
3
3,046
24 Cherry Lane, Madison, CT
0.25
Single-Family Home
$1,186,900
05/08/26
3
2.5
1,712
39 Madison Avenue, Madison, CT
0.45
Single-Family Home
$1,045,000
09/26/25
4
3
1,891
49 Middle Beach Rd, Madison, CT
0.45
Single-Family Home
$750,000
05/12/26
6
3
2,929
584 Boston Post Road, Madison, CT
0.23
Single-Family Home
$1,525,000
10/01/25
5
5.5
6,278
880 Boston Post Road, Madison, CT
0.62
Single-Family Home
$2,145,000
08/17/26
4
3.5
3,697
86B East Wharf Road, Madison, CT
0.53
Single-Family Home
$2,505,000
10/27/25
4
3.5
3,160
36 Cedar Lane, Madison, CT
0.34
Single-Family Home
$2,310,000
07/15/26
4
4
3,926

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
0.06
$1,913,600
3
2.5
2,756
Off Market
24 Windward Lane, Madison, CT 06443
0.10
$1,785,400
3
3.5
3,628
Off Market
15 Windward Lane, Madison, CT 06443
0.14
$1,682,700
4
3.5
2,704
Off Market
79 Island Avenue, Madison, CT 06443
0.16
$2,246,200
4
3.5
3,741
Off Market
57 Island Avenue, Madison, CT 06443
0.16
$1,660,700
4
3.5
3,006
Off Market
45 Island Avenue, Madison, CT 06443
0.17
$3,495,000
5
5
5,657
For Sale
10 Middle Beach Road West, Madison, CT 06443
0.18
$3,775,000
6
6
6,074
Recently Sold
55 Island Avenue, Madison, CT 06443
0.17
$1,400,000
4
3
3,046
Recently Sold
3 Sunset Road, Madison, CT 06443
0.19
$1,268,100
3
2.5
1,980
Off Market
85 Island Avenue, Madison, CT 06443
0.21
$2,340,900
5
4.5
4,472
Off Market
4 Cambridge Drive #4, Madison, CT 06443
0.21
$1,055,600
2
2.5
2,358
Off Market
11 Sunset Road, Madison, CT 06443
0.22
$1,324,300
3
3
2,186
Off Market

Local Information

  • Map ViewExplore the area around 42 Windward Ln.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1977
0.54 acre lot
3,255 sqft
$539/sqft
Garage

About this House

When they talk about LOCATION, LOCATION, LOCATION, this is the house they mean. In a neighborhood--at the end of a cul de sac-- two blocks to Long Island Sound--walking distance to library, concerts on the green--farmers market. We could go on and on. House features a first floor apt with a full bath and galley kitchen and separate exterior entrance. This can be rented or used as a first floor bedroom. Newly installed gas furnace, on demand water heater and central air.
42 Windward Ln, Madison, CT 06443 is a 4 bedroom, 5 bathroom, 3,255 sqft single-family home in Madison Center, built in 1977. It last sold for $865,000 on Jun 9, 2017. More recently, it was listed as a rental in March 2014 with an asking price of $3,600 per month. That rental listing was removed on April 15, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,755,100.

Home Details for 42 Windward Ln

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Interior Details
AtticNumber of Rooms: 10Types of Rooms: Laundry Room
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Hardwood

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Vinyl
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1977
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 0.54 acres

Price and Tax history

DateEventPrice
Jun 9, 2017
Source: Smart MLS #N10201422
Sold
$865,000
Mar 28, 2017
Source: Agent Provided
Pending
$889,889
Mar 4, 2017
Source: Agent Provided
Listed For Sale
$889,889
Jun 21, 2016
Source: Agent Provided
ListingRemoved
$929,000
Mar 2, 2016
Source: Agent Provided
PriceChange
$929,000
Price decreased by 2%

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
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Frequently asked questions about 42 Windward Ln

  • What is 42 Windward Ln estimated to be worth?
    Trulia's estimated value for 42 Windward Ln in Madison, CT is $1,755,100.
  • What is the price history for 42 Windward Ln?
    42 Windward Ln in Madison, CT last sold for $865,000 in June 2017.
  • 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.
  • Does 42 Windward Ln have air conditioning?
    Yes, 42 Windward Ln in Madison, CT has air conditioning.
  • Does 42 Windward Ln have laundry facilities?
    Yes, 42 Windward Ln in Madison, CT has in-unit laundry.

Explore by feature - Pet Friendly

7 pet-friendly rentals in Madison, CT

Explore by feature - Air Conditioning

18 rentals with air conditioning in Madison, CT

Explore by feature - Washer/dryer

21 rentals with a washer/dryer in Madison, CT

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Off Market Homes Near 42 Windward Ln

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