36 Windmill Ln, Chatham, MA 02633
Property image
Property image
OFF MARKET

36 Windmill Ln
Chatham, MA 02633

  • 5 Beds
  • 2 Baths
  • 1,732 sqft (on 1.14 acres)

$4,402,800

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $24,762/mo*
Refinance Your Home

$4,402,800

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $24,762/mo*
Refinance Your Home
5 Beds
2 Baths
1,732 sqft
(on 1.14 acres)

Home Value

Trulia Estimate
$4.4M
Since last month
Increased$32K (+0.7%)
Since last year
Increased$289K (+6.9%)
Since last sale
Increased$2M (+94.2%)
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 +96% in the last 10 years
MonthEstimated value
2026
August 2026$4.47M
July 2026$4.44M
June 2026$4.48M
May 2026$4.38M
April 2026$4.28M
March 2026$4.25M
February 2026$4.23M
January 2026$4.15M
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
32 Sunset Lane, Chatham, MA
0.60
Single-Family Home
$1,622,500
03/09/26
3
2
1,626
213 Main Street, Chatham, MA
0.61
Single-Family Home
$1,800,000
07/31/26
4
2
1,236
150 Main Street, Chatham, MA
0.52
Single-Family Home
$6,000,000
04/14/26
7
2.5
2,552
85 Main Street, Chatham, MA
0.38
Single-Family Home
$4,000,000
10/03/25
3
3.5
2,998
42 Champlain Road, Chatham, MA
0.89
Single-Family Home
$1,510,000
06/11/26
4
2
1,435
80 Tisquantum Road, Chatham, MA
0.77
Single-Family Home
$3,450,000
09/12/25
3
3.5
2,821
298 Chipping Stone Rd, Chatham, MA
0.93
Single-Family Home
$1,050,000
05/15/26
4
2
2,148
85 Cedar Street, Chatham, MA
1.00
Single-Family Home
$4,050,000
07/13/26
5
3.5
3,080
51 Shattuck Place, Chatham, MA
0.85
Single-Family Home
$2,610,000
10/02/25
3
2.5
2,133
330 Champlain Road, Chatham, MA
1.32
Single-Family Home
$2,375,000
08/18/26
4
3
2,520

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
16 Windmill Lane, Chatham, MA 02633
0.04
$2,940,000
4
1.5
1,669
Off Market
101 Morris Island Road, Chatham, MA 02633
0.08
$4,995,000
5
4.5
3,225
For Sale
16 Little Beach Road, Chatham, MA 02633
0.10
$2,209,800
3
3.5
1,863
Off Market
32 Little Beach Road, Chatham, MA 02633
0.14
$2,236,800
5
3.5
1,713
Off Market
0 Seagull Road, Chatham, MA 02633
0.16
-
-
-
-
Off Market
8 Oyster Drive, Chatham, MA 02633
0.21
$1,018,800
3
1
748
Off Market
28 Starfish Lane #28, Chatham, MA 02633
0.22
$1,181,400
2
2
1,089
Off Market
16 Starfish Lane #16, Chatham, MA 02633
0.22
$806,300
2
2
928
Off Market
6 Starfish Lane #6, Chatham, MA 02633
0.22
$661,700
2
1
750
Off Market
4 Starfish Lane #4, Chatham, MA 02633
0.22
$538,900
2
1.5
568
Off Market
16 Starfish Lane, Chatham, MA 02633
0.24
$722,100
2
2
928
Off Market
73 Main St #8, Chatham, MA 02633
0.35
$584,600
1
1
551
Off Market

Local Information

  • Map ViewExplore the area around 36 Windmill Ln.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1953
Lot Size
1.14 acres
Living Area
1,732 sqft
Price/Sqft
$2,542
Parking
Garage

About this House

Enjoy this premier beachfront opportunity in Chatham. With stunning views of South Beach and a short walk to Chatham Lighthouse, this is a classic Cape Cod beach cottage. Affording tastefully renovated interiors and abundant natural light, there are five bedrooms, a casual family room with vaulted ceilings and fireplace, dining room, and a charming kitchen. Most rooms look out on sweeping unspoiled vistas. Additional highlights include a finished room in the basement, a two car garage and Central AC. This is a rare offering.
36 Windmill Ln, Chatham, MA 02633 is a 5 bedroom, 2 bathroom, 1,732 sqft single-family home built in 1953. It last sold for $2,300,000 on Dec 27, 2012. It is currently off market. The Trulia Estimate is $4,402,800, with a rent estimate of $4,696/month.

Home Details for 36 Windmill Ln

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Interior Details
Number of Rooms: 8

Exterior Features

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

Property Information

Year Built
Year Built: 1953Year Updated: 2003
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 1.14 acres

Price and Tax history

DateEventPrice
Dec 27, 2012
Source: CCIMLS #21210390
Sold
$2,300,000
Dec 12, 2012
Source: Agent Provided
Listed For Sale
$2,495,000
Mar 6, 2009
Source: CCIMLS #20809038
Sold
$1,800,000
Jan 7, 2000
Source: N/A
Sold
$977,850

Market trends in Chatham

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.14M
Sale-to-List Price
97.9%
Price per sq ft
$704
Available listings
72
3MoM

Around this home

What Locals Say about Chatham

At least 40 Trulia users voted on each feature.

  • 88 % Say there's wildlife

  • 87 % Say parking is easy

  • 83 % Say there's holiday spirit

  • 83 % Say yards are well-kept

  • 83 % Say it's dog friendly

  • 82 % Say people would walk alone at night

  • 82 % Say car is needed

  • 73 % Say it's quiet

  • 72 % Say they plan to stay for at least 5 years

  • 59 % Say neighbors are friendly

  • 48 % Say it's walkable to restaurants

  • 47 % Say kids play outside

  • 38 % Say there are community events

  • 33 % Say there are sidewalks

  • 21 % Say streets are well-lit

  • 20 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Snbrinc
    "I’m 4th generation living in this neighborhood. Very special highly desirable place. Proud to be a native. "
    1
    Flag
  • Lilsweeti56
    "Lots of farms. Stop and shop is also close by along with cvs and some banks. Close by to highway. Most people are friendly"
    1
    Flag
  • Virginia S.
    "It’s beautiful, near stores, beach, highways. Quiet and neighbors mind their own business. Lake at end of our street."
    0
    Flag
  • Pmil
    "They would like that most people keep their dog on a leash. They would not like the coyotes in winter"
    1
    Flag
  • Mil
    "Most dogs are on leashes, and in some areas they have doggie poop bags, they have a lot of green. Peomost people pick up after their pets. In winter be careful, foxes and coyotes, deer and wild turkeys are found"
    2
    Flag
  • George G.
    "Easy because it is a small place in the Cape Cod and I love it here because it is also a older community "
    0
    Flag
  • Tuscansun83
    "It's such a peaceful place Chatham is one of the best towns to live in year round or part time it's just beautiful"
    0
    Flag
  • jandesmar
    "I love that it is so close to the boat landing that we can walk to it and watch the activity with our grandchildren. We can also walk to the beach which is a mile away to swim and watch the sunsets,"
    0
    Flag
  • Nancy P.
    "Safe small town with beautiful beaches and a strong sense of community. I love living here. Great place to grow up and raise children "
    1
    Flag
  • Jack D. B.
    "I grew up nearby and can attest to what a great location this is - an easy walk to town, yet just far enough from the peak summer hustle and bustle. "
    0
    Flag
  • mwff1
    "Wonderful, convenient, yet very private area! Conservation and park areas prevalent nearby"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 36 Windmill Ln

  • What is 36 Windmill Ln estimated to be worth?
    Trulia's estimated value for 36 Windmill Ln in Chatham, MA is $4,402,800.
  • What is the price history for 36 Windmill Ln?
    36 Windmill Ln in Chatham, MA last sold for $2,300,000 in December 2012.
  • Is Chatham a buyer's or seller's market?
    Chatham is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Chatham?
    The median sale price in Chatham is $1.14M.
  • Does 36 Windmill Ln have air conditioning?
    Yes, 36 Windmill Ln in Chatham, MA has air conditioning.
  • How big is the lot at 36 Windmill Ln?
    The lot at 36 Windmill Ln in Chatham, MA is about 1.1 acres.

Explore by feature - Air Conditioning

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