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

$1,391,400

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,092 sqft (on 0.52 acres)

37 Windward Ln, Madison, CT 06443

Madison Center
Est. Refi. Payment $9,625/mo*
Refinance Your Home
Currently Off Market - Sold Apr 19, 2018 for $685,000

Home Value

Trulia Estimate
$1.39M
Since last month
Decreased$7K (-0.5%)
Since last year
Increased$52K (+3.9%)
Since last sale
Increased$706K (+103.1%)
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 +107% in the last 10 years
MonthEstimated value
2026
August 2026$1.39M
July 2026$1.4M
June 2026$1.42M
May 2026$1.39M
April 2026$1.35M
March 2026$1.32M
February 2026$1.3M
January 2026$1.32M
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
24 Cherry Lane, Madison, CT
0.23
Single-Family Home
$1,186,900
05/08/26
3
2.5
1,712
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
0.25
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
73 Middle Beach Rd W, Madison, CT
0.35
Single-Family Home
$487,666
12/12/25
5
2
2,436
39 Madison Avenue, Madison, CT
0.46
Single-Family Home
$1,045,000
09/26/25
4
3
1,891
55 Island Avenue, Madison, CT
0.21
Single-Family Home
$1,400,000
07/17/26
4
3
3,046
86A East Wharf Road, Madison, CT
0.61
Single-Family Home
$1,615,000
08/12/26
3
2
1,824
20 Cherry Lane, Madison, CT
0.24
Single-Family Home
$1,453,000
08/29/25
5
3.5
2,647
11 Middle Beach Road, Madison, CT
0.37
Single-Family Home
$1,825,000
06/01/26
3
3
1,976
43 Burcam Drive, Madison, CT
0.60
Single-Family Home
$941,000
10/01/25
3
3
2,393

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
0.05
$1,921,400
3
2.5
2,756
Off Market
24 Windward Lane, Madison, CT 06443
0.07
$1,788,200
3
3.5
3,628
Off Market
15 Windward Lane, Madison, CT 06443
0.11
$1,682,700
4
3.5
2,704
Off Market
10 Middle Beach Road West, Madison, CT 06443
0.14
$3,775,000
6
6
6,074
Recently Sold
79 Island Avenue, Madison, CT 06443
0.16
$2,247,100
4
3.5
3,741
Off Market
24 Cherry Lane, Madison, CT 06443
0.23
$1,186,900
3
2.5
1,712
Recently Sold
57 Island Avenue, Madison, CT 06443
0.19
$1,667,700
4
3.5
3,006
Off Market
20 Cherry Lane, Madison, CT 06443
0.24
$1,688,400
5
3.5
2,647
Off Market
3 Sunset Road, Madison, CT 06443
0.18
$1,272,100
3
2.5
1,980
Off Market
45 Island Avenue, Madison, CT 06443
0.21
$3,495,000
5
5
5,657
For Sale
519 Boston Post Road, Madison, CT 06443
0.25
$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 37 Windward Ln.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1968
Lot Size
0.52 acres
Living Area
2,092 sqft
Price/Sqft
$665
Parking
Garage

About this House

It's not just a location. It's a lifestyle. One of the best locations in Madison south of Boston Post Road. This 3 bedroom/2 full bath colonial is located on a quiet cul-de-sac. Hardwood floors throughout, central air and the option for a first or second floor master bedroom. Natural gas is available on the street. Walk to the village, the green, town beaches, Madison Country Club, Madison Beach Club, and local restaurants. Enjoy life by the water. This home is an easy commute to New Haven, Middletown or Hartford. An ideal year round home or an easy train ride to New York or Boston. Come and vacation where you live!
37 Windward Ln, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,092 sqft single-family home in Madison Center, built in 1968. It last sold for $685,000 on Apr 19, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,391,400, with a rent estimate of $4,530/month.

Home Details for 37 Windward Ln

Interior Features

Heating & Cooling
Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
AtticNumber of Rooms: 7Types of Rooms: Walk In Closet, Mud RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodGardenLawnPatio
Parking & Garage
GarageParking Spaces: 8Parking: Garage Attached

Property Information

Year Built
Year Built: 1968Year Updated: 2018
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 0.52 acres

Price and Tax history

DateEventPrice
Apr 19, 2018
Source: Smart MLS #170059057
Sold
$685,000
Mar 15, 2018
Source: Agent Provided
Pending
$699,900
Mar 10, 2018
Source: Agent Provided
Listed For Sale
$699,900

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 37 Windward Ln

  • What is 37 Windward Ln estimated to be worth?
    Trulia's estimated value for 37 Windward Ln in Madison, CT is $1,391,400.
  • What is the price history for 37 Windward Ln?
    37 Windward Ln in Madison, CT last sold for $685,000 in April 2018.
  • 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 37 Windward Ln have air conditioning?
    Yes, 37 Windward Ln in Madison, CT has air conditioning.
  • Does 37 Windward Ln have laundry facilities?
    Yes, 37 Windward Ln in Madison, CT has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Washer/dryer

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Off Market Homes Near 37 Windward Ln

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