44 Sears Rd, Chatham, MA 02633
Post and Beam Construction
Mudroom
OFF MARKET

44 Sears Rd
Chatham, MA 02633

  • 4 Beds
  • 3.5 Baths
  • 3,800 sqft (on 0.92 acres)

$2,954,300

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $16,531/mo*
Refinance Your Home

$2,954,300

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $16,531/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,800 sqft
(on 0.92 acres)

Home Value

Trulia Estimate
$2.95M
Since last month
Decreased$20K (-0.7%)
Since last year
Increased$104K (+3.7%)
Since last sale
Increased$1M (+85.1%)
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 +91% in the last 10 years
MonthEstimated value
2026
August 2026$2.96M
July 2026$2.98M
June 2026$2.98M
May 2026$2.9M
April 2026$2.88M
March 2026$2.88M
February 2026$2.81M
January 2026$2.79M
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
330 Champlain Road, Chatham, MA
0.12
Single-Family Home
$2,375,000
08/18/26
4
3
2,520
106 Stage Neck Road, Chatham, MA
0.27
Single-Family Home
$2,500,000
10/24/25
4
3.5
3,834
86 Champlain Road, Chatham, MA
0.47
Single-Family Home
$2,830,000
01/30/26
3
4.5
4,361
7 Squanto Drive, Chatham, MA
0.62
Single-Family Home
$2,940,000
07/28/26
3
3.5
3,014
20 Hardings Beach Road, Chatham, MA
0.81
Single-Family Home
$1,975,000
10/08/25
4
3.5
2,770
87 Squanto Drive, Chatham, MA
0.57
Single-Family Home
$3,250,000
08/06/26
3
3.5
3,902
404 Stage Harbor Road, Chatham, MA
0.64
Single-Family Home
$3,020,000
01/15/26
4
3.5
2,905
42 Champlain Road, Chatham, MA
0.55
Single-Family Home
$1,510,000
06/11/26
4
2
1,435
13 Captain Knowles Way, Chatham, MA
0.41
Single-Family Home
$6,995,000
11/21/25
5
6
5,700
55 Meadowview Road S, Chatham, MA
0.82
Single-Family Home
$2,000,000
09/08/25
4
3
1,897

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
0 Sears Road, Chatham, MA 02633
0.03
-
-
-
-
Off Market
0 Harbor Hill, Chatham, MA 02633
0.06
-
-
-
-
Off Market
25 Harbor Hill, Chatham, MA 02633
0.05
$2,483,400
4
3
2,331
Off Market
36 Sears Point, Chatham, MA 02633
0.03
$9,662,900
10
4
4,421
Off Market
16 Sears Pt, Chatham, MA 02633
0.07
$2,660,000
3
2.5
1,872
Off Market
60 Harbor Hill Road, Chatham, MA 02633
0.08
$2,950,000
4
3.5
3,978
For Sale
1 sears, Chatham, MA 02633
0.10
$4,270,100
4
3.5
4,000
Off Market
36 Sears Point-Lot B, Chatham, MA 02633
0.16
$2,680,800
2
2
1,550
Off Market
330 Champlain Road, Chatham, MA 02633
0.12
$2,375,000
4
3
2,520
Recently Sold
189 Moonpenny Lane, Chatham, MA 02633
0.21
$5,386,600
6
4.5
2,919
Off Market
371 Cedar Street, Chatham, MA 02633
0.23
$1,818,900
3
2.5
1,840
Off Market
70 Sears Pt Lane, Chatham, MA 02633
0.29
$6,180,400
5
3
2,992
Off Market

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
2004
Lot Size
0.92 acres
Living Area
3,800 sqft
Price/Sqft
$777

About this House

New! This is a must-see house! Located just off "the loop" on a dead-end street this shingle-style home offers privacy and bright sunny rooms. The open floor plan and large deck create easy indoor/outdoor living spaces. Boasting 4 bedrooms (including 1st and 2nd floor master suites with private decks) and 3.5 bathrooms, this 3800 sf home also has a chef's kitchen (Sub-Zero and Wolf) with soapstone counter-tops throughout. Two office spaces, a theater room, built-in indoor/outdoor stereo system, large laundry room, outdoor shower, and a basement gym round out the many features of this house. Outdoors, take a glass of wine up to the roof deck for a bird’s eye view of Stage Harbor and the South Beach break while the teenagers roast marshmallows at the fire pit nestled among mature perennials and the kids and/or dogs run and play in the yard.
A 3 min walk away, Stage Harbor offers protected boating and access to Nantucket Sound, miles of secluded beaches, warmer water for swimming. . . no sharks! If you would prefer to swim in a pool, there is room in the back yard for one!
Listed below Town and Bank appraisals (1,813k and 1,850k, respectively) by more than 125K, you will want to see this one sooner rather than later! Just image: Cocktails on the deck on the 4th of July!
44 Sears Rd, Chatham, MA 02633 is a 4 bedroom, 4 bathroom, 3,800 sqft single-family home built in 2004. It last sold for $1,597,500 on May 1, 2017. It is currently off market. The Trulia Estimate is $2,954,300, with a rent estimate of $6,908/month.

Home Details for 44 Sears Rd

Interior Features

Heating & Cooling
Heating: Forced Air, Radiant, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 4

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: ShingleLawnPatioPorchSprinkler System
Parking & Garage
Parking Spaces: 2Parking: Carport, Off Street

Property Information

Year Built
Year Built: 2004Year Updated: 2006
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.92 acres

Price and Tax history

DateEventPrice
Mar 24, 2021
Source: N/A
ListingRemoved
May 1, 2017
Source: N/A
Sold
$1,597,500
Apr 4, 2017
Source: N/A
Pending
$1,679,000
Feb 28, 2017
Source: N/A
Listed For Sale
$1,679,000
Nov 29, 2016
Source: N/A
ListingRemoved
$1,695,000

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 Sears Rd

  • What is 44 Sears Rd estimated to be worth?
    Trulia's estimated value for 44 Sears Rd in Chatham, MA is $2,954,300.
  • What is the price history for 44 Sears Rd?
    44 Sears Rd in Chatham, MA last sold for $1,597,500 in May 2017.
  • 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 44 Sears Rd have air conditioning?
    Yes, 44 Sears Rd in Chatham, MA has air conditioning.
  • How big is the lot at 44 Sears Rd?
    The lot at 44 Sears Rd in Chatham, MA is about 0.92 acres (40,075 sq ft).

Apartments for Rent

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Off Market Homes Near 44 Sears Rd

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