585 Main St, Chatham, MA 02633
OFF MARKET

$1,860,000

Trulia Estimate
  • Studio

585 Main St, Chatham, MA 02633

Est. Refi. Payment $10,456/mo*
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Home Value

Trulia Estimate
$1.86M
Since last month
Increased$54K (+3%)
Since last year
Increased$222K (+13.6%)
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 +9% in the last 10 years
MonthEstimated value
2026
August 2026$1.86M
August 2026$1.86M
July 2026$1.81M
June 2026$1.82M
May 2026$1.77M
April 2026$1.82M
March 2026$1.73M
February 2026$1.79M
January 2026$1.82M
2025
2024
2023

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
8 Kingsbury Way, Chatham, MA
0.15
Single-Family Home
$2,199,900
04/29/26
3
2.5
1,651
24 Shattuck Pl, Chatham, MA
0.21
Single-Family Home
$1,785,000
11/24/25
4
2.5
1,514
745-747 Main Street, Chatham, MA
0.11
Single-Family Home
$1,375,000
02/19/26
6
3
2,257
51 Shattuck Place, Chatham, MA
0.24
Single-Family Home
$2,610,000
10/02/25
3
2.5
2,133
292 Stage Harbor Road, Chatham, MA
0.55
Single-Family Home
$1,875,000
03/24/26
3
4.5
1,834
101 Oyster Pond Furlong Street, Chatham, MA
0.46
Single-Family Home
$2,650,000
03/17/26
4
2
2,057
92 Hitching Post Road, Chatham, MA
0.48
Single-Family Home
$1,335,000
07/15/26
4
1.5
1,951
605 Main St, Chatham, MA
0.05
Single-Family Home
$726,750
03/04/26
1
827
121 Queen Anne Road, Chatham, MA
0.29
Single-Family Home
$5,400,000
03/31/26
4
5.5
3,702
32 Sunset Lane, Chatham, MA
0.53
Single-Family Home
$1,622,500
03/09/26
3
2
1,626

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
36 Bearses By-Way, Chatham, MA 02633
0.05
$1,436,500
3
2.5
1,671
Off Market
595 Main Street #37, Chatham, MA 02633
0.05
$2,168,700
3
3
2,148
Off Market
26 Bearses By-Way, Chatham, MA 02633
0.05
$1,121,500
2
2.5
1,300
Off Market
595 Main Street #X37, Chatham, MA 02633
0.05
$1,978,000
3
3
2,148
Off Market
33 Cross St #4, Chatham, MA 02633
0.10
$202,200
1
1
450
Off Market
435-F Main Street, Chatham, MA 02633
0.11
$482,300
2
1
616
Off Market
745-747 Main Street, Chatham, MA 02633
0.11
$1,375,000
6
3
2,257
Recently Sold
5 Kingsbury Way, Chatham, MA 02633
0.13
$2,995,000
3
3.5
2,405
For Sale
39 Seaview Terrace, Chatham, MA 02633
0.18
$4,183,000
4
6.5
3,533
Off Market
8 Kingsbury Way, Chatham, MA 02633
0.15
$2,199,900
3
2.5
1,651
Recently Sold
109 Seaview Street #3, Chatham, MA 02633
0.20
$1,170,500
2
2.5
1,160
Off Market
30 Fairway Drive, Chatham, MA 02633
0.22
$7,478,900
5
7
6,128
Off Market

Local Information

  • Map ViewExplore the area around 585 Main St.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home

About this House

This single-family home is located at 585 Main St, Chatham, MA. 585 Main St is in Chatham, MA and in ZIP code 02633. This property has a lot size of 5662 sqft.
585 Main St, Chatham, MA 02633 is a studio single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,860,000, with a rent estimate of $4,870/month.

Home Details for 585 Main St

Property Information

Property Type / Style
Property Type: Single Family Home

Interior Features

Heating & Cooling
Air Conditioning

Lot Information

Lot Area: 5662 sqft

Price and Tax history

YearProperty taxTax assessment
2025
$5,238
$1,509,500
Home facts updated by county records

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 585 Main St

  • What is 585 Main St estimated to be worth?
    Trulia's estimated value for 585 Main St in Chatham, MA is $1,860,000.
  • 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.
  • What do residents say about Chatham?
    Residents describe Chatham, MA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Chatham, MA.
  • How big is the lot at 585 Main St?
    The lot at 585 Main St in Chatham, MA is about 0.13 acres (5,662 sq ft).

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