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

$1,930,100

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,215 sqft (on 0.55 acres)

27 Windward Ln, Madison, CT 06443

Madison Center
Est. Refi. Payment $13,712/mo*
Refinance Your Home
Currently Off Market - Sold Dec 16, 2021 for $1,375,000

Home Value

Trulia Estimate
$1.93M
Since last month
Decreased$9K (-0.5%)
Since last year
Increased$100K (+5.5%)
Since last sale
Increased$559K (+40.7%)
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 +34% in the last 10 years
MonthEstimated value
2026
August 2026$1.93M
August 2026$1.92M
July 2026$1.94M
June 2026$1.96M
May 2026$1.93M
April 2026$1.89M
March 2026$1.87M
February 2026$1.84M
January 2026$1.85M
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
0.30
Single-Family Home
$1,100,000
12/18/25
4
2.5
3,031
55 Island Avenue, Madison, CT
0.23
Single-Family Home
$1,400,000
07/17/26
4
3
3,046
519 Boston Post Road, Madison, CT
0.29
Single-Family Home
$895,000
02/02/26
4
2.5
2,691
24 Cherry Lane, Madison, CT
0.24
Single-Family Home
$1,186,900
05/08/26
3
2.5
1,712
86B East Wharf Road, Madison, CT
0.55
Single-Family Home
$2,505,000
10/27/25
4
3.5
3,160
584 Boston Post Road, Madison, CT
0.32
Single-Family Home
$1,525,000
10/01/25
5
5.5
6,278
39 Madison Avenue, Madison, CT
0.45
Single-Family Home
$1,045,000
09/26/25
4
3
1,891
880 Boston Post Road, Madison, CT
0.68
Single-Family Home
$2,145,000
08/17/26
4
3.5
3,697
36 Cedar Lane, Madison, CT
0.36
Single-Family Home
$2,310,000
07/15/26
4
4
3,926
86 E Wharf Rd, Madison, CT
0.61
Single-Family Home
$2,505,000
10/28/25
4
3.5
3,168

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
24 Windward Lane, Madison, CT 06443
0.05
$1,785,400
3
3.5
3,628
Off Market
34 Windward Lane, Madison, CT 06443
0.05
$1,913,600
3
2.5
2,756
Off Market
15 Windward Lane, Madison, CT 06443
0.07
$1,682,700
4
3.5
2,704
Off Market
10 Middle Beach Road West, Madison, CT 06443
0.11
$3,775,000
6
6
6,074
Recently Sold
79 Island Avenue, Madison, CT 06443
0.14
$2,246,200
4
3.5
3,741
Off Market
3 Sunset Road, Madison, CT 06443
0.15
$1,268,100
3
2.5
1,980
Off Market
11 Sunset Road, Madison, CT 06443
0.18
$1,324,300
3
3
2,186
Off Market
85 Island Avenue, Madison, CT 06443
0.19
$2,340,900
5
4.5
4,472
Off Market
57 Island Avenue, Madison, CT 06443
0.19
$1,660,700
4
3.5
3,006
Off Market
24 Cherry Lane, Madison, CT 06443
0.24
$1,186,900
3
2.5
1,712
Recently Sold
35 West Wharf Road, Madison, CT 06443
0.25
$1,489,300
3
2.5
1,698
Off Market
55 Island Avenue, Madison, CT 06443
0.23
$1,400,000
4
3
3,046
Recently Sold

Local Information

  • Map ViewExplore the area around 27 Windward Ln.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1968
0.55 acre lot
3,215 sqft
$600/sqft
Garage

About this House

No need to drive to the beaches from home, just walk to the Madison Beach Club or the Village Green! This builders personal residence, located on a quiet cul-de-sac, has been recently renovated with care, quality and great taste. With just under 3300 square feet of living area, this is an impressive home with sunny and spacious rooms. A stone walkway leads to the main foyer, graced with hardwood floors, an open stairway and a vaulted ceiling all clues to the thoughtful attention to design and materials throughout this home. The main level is anchored by a great room ready for cozy fire-side stories or watching sports games on Sunday afternoons, and, by the eat-in kitchen which includes granite countertops, an island for 4+, a wine cooler, warming oven and impressive wood cabinetry. Formal living and dining rooms invite entertaining. French doors, vaulted ceilings, exposed beams, wainscoting, and recessed lighting add a contemporary flair to the classic appeal. Attached is a 2-car garage for more than your cars. Youll want your bikes, snowboards, water gear and gardening supplies here. The property includes acre of level lawn defined by mature trees and plenty of space for gardening, a swing-set, badminton and baseball, or a cook-out after a day at the beach! Light fixture in dining room and blown glass light fixture in kitchen not included in sale.
27 Windward Ln, Madison, CT 06443 is a 4 bedroom, 4 bathroom, 3,215 sqft single-family home in Madison Center, built in 1968. It last sold for $1,375,000 on Dec 16, 2021. More recently, it was listed as a rental in December 2019 with an asking price of $5,500 per month. That rental listing was removed on December 30, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,930,100, with a rent estimate of $7,329/month.

Home Details for 27 Windward Ln

Interior Features

Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Shingle Not Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

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

Lot Information

Lot Area: 0.55 acres

Price and Tax history

DateEventPrice
Dec 16, 2021
Source: Smart MLS #170396894
Sold
$1,375,000
Oct 30, 2021
Source: Smart MLS #170396894
Contingent
$1,385,000
Sep 22, 2021
Source: William Raveis Real Estate, Mortgage & Insurance #170396894
Pending
$1,385,000
May 6, 2021
Source: Smart MLS #170396894
Listed For Sale
$1,385,000
Sep 21, 2020
Source: Agent Provided
ListingRemoved
$1,399,000

Market trends in Madison

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$716K
$6.67KMoM
Sale-to-List Price
101.8%
0.2%MoM
Price per sq ft
$337
$3MoM
Available listings
59
4MoM

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 27 Windward Ln

  • What is 27 Windward Ln estimated to be worth?
    Trulia's estimated value for 27 Windward Ln in Madison, CT is $1,930,100.
  • What is the price history for 27 Windward Ln?
    27 Windward Ln in Madison, CT last sold for $1,375,000 in December 2021.
  • 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 $716K. That is up $6.67K from the prior month.
  • Does 27 Windward Ln have air conditioning?
    Yes, 27 Windward Ln in Madison, CT has air conditioning.
  • Does 27 Windward Ln have laundry facilities?
    Yes, 27 Windward Ln in Madison, CT has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 27 Windward Ln

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