44 Pine Dr, Chatham, MA 02633
OFF MARKET

44 Pine Dr
Chatham, MA 02633

  • 2 Beds
  • 1 Bath
  • 700 sqft

$777,600

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $4,435/mo*
Refinance Your Home

$777,600

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $4,435/mo*
Refinance Your Home
2 Beds
1 Bath
700 sqft

Home Value

Trulia Estimate
$778K
Since last month
Increased$7K (+0.9%)
Since last year
Increased$98K (+14.2%)
Since last sale
Increased$638K (+428.2%)
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 +113% in the last 10 years
MonthEstimated value
2026
August 2026$787K
July 2026$780K
June 2026$788K
May 2026$756K
April 2026$735K
March 2026$743K
February 2026$735K
January 2026$727K
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
22 Pine Knoll Ave, Chatham, MA
0.14
Single-Family Home
$510,000
01/22/26
3
0.5
532
17 Bog Way, Chatham, MA
0.14
Single-Family Home
$1,500,000
10/03/25
2
1
1,633
17 Bog Way Road, Chatham, MA
0.14
Single-Family Home
$1,500,000
10/03/25
2
1
1,633
19 Stoughton Lane, Chatham, MA
0.05
Single-Family Home
$575,000
09/25/25
3
2
1,356
291 Ridgevale Road, Chatham, MA
0.13
Single-Family Home
$1,495,000
12/15/25
3
1.5
1,424
65 Lantern Lane, South Chatham, MA
0.50
Single-Family Home
$825,000
10/08/25
3
1
1,251
47 Cranberry Way, South Chatham, MA
0.56
Single-Family Home
$765,000
12/18/25
2
2
868
26 Pine Tree Rd, Chatham, MA
0.75
Single-Family Home
$692,500
07/08/26
2
1
1,080
26 Pine Tree Rd, South Chatham, MA
0.75
Single-Family Home
$692,500
07/08/26
2
1
1,080
116 Happy Valley Road, Chatham, MA
0.38
Single-Family Home
$1,350,000
10/23/25
2
3
1,861

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
27 Stoughton Lane, Chatham, MA 02633
0.03
$1,738,300
2
3
2,675
Off Market
19 Stoughton Lane, Chatham, MA 02633
0.05
$892,000
3
2
1,356
Off Market
27 Patterson Road, Chatham, MA 02633
0.07
$3,354,000
4
3.5
3,224
Off Market
57 Whitman Avenue #B, South Chatham, MA 02659
0.09
$726,400
2
2
1,000
Off Market
57 Whitman Avenue #A, South Chatham, MA 02659
0.09
$561,600
2
2
1,000
Off Market
57 Whitman Avenue UNIT A, Chatham, MA 02633
0.09
$699,000
2
2
900
For Sale
58 Diane Drive, Chatham, MA 02633
0.10
$987,600
2
1
1,331
Off Market
291 Ridgevale Road, Chatham, MA 02633
0.13
$1,495,000
3
1.5
1,424
Recently Sold
17 Bog Way, Chatham, MA 02633
0.14
$1,502,700
2
1
1,633
Off Market
17 Bog Way Road, Chatham, MA 02633
0.14
$1,497,100
2
1
1,633
Off Market
22 Pine Knoll Ave, Chatham, MA 02633
0.14
$510,000
3
0.5
532
Recently Sold
0 S Ridgevale Road, Chatham, MA 02633
0.16
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 44 Pine Dr.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1962
Living Area
700 sqft
Price/Sqft
$1,111

About this House

This single-family home is located at 44 Pine Dr, Chatham, MA. 44 Pine Dr is in Chatham, MA and in ZIP code 02633. This property has 2 bedrooms, 1 bathroom and approximately 700 sqft of floor space. This property has a lot size of 7840 sqft and was built in 1962.
44 Pine Dr, Chatham, MA 02633 is a 2 bedroom, 1 bathroom, 700 sqft single-family home built in 1962. It last sold for $149,000 on Oct 12, 2007. It is currently off market. The Trulia Estimate is $777,600, with a rent estimate of $2,547/month.

Home Details for 44 Pine Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 4

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1962Year Updated: 1969
Property Type / Style
Property Type: Single Family HomeArchitecture: cottage

Community

Units in Building: 1

Lot Information

Lot Area: 7840 sqft

Price and Tax history

DateEventPrice
Oct 12, 2007
Source: N/A
Sold
$149,000

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 44 Pine Dr

  • What is 44 Pine Dr estimated to be worth?
    Trulia's estimated value for 44 Pine Dr in Chatham, MA is $777,600.
  • What is the price history for 44 Pine Dr?
    44 Pine Dr in Chatham, MA last sold for $149,000 in October 2007.
  • 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.
  • How big is the lot at 44 Pine Dr?
    The lot at 44 Pine Dr in Chatham, MA is about 0.18 acres (7,840 sq ft).

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