Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 2 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 3 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 4 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 5 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 6 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 7 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 8 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 9 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 10 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 11 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 12 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 13 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 14 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 15 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 16 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 17 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 18 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 19 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 20 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 21 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 22 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 23 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 24 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 25 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 26 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 27 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 28 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 29 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 30 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 31 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 32 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 33 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 34 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 35 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 36 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 37 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 38 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 39 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 40 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 41 of 42
Single Family Residence at 5 Kingsbury Way, Chatham MA 02633, Chatham, photo 42 of 42
42 photos

$2,995,000

5 Kingsbury Way, Chatham MA 02633
Chatham, MA 02633
Listed by Guthrie Schofield Group
Bedrooms
3
Bathrooms
3.5
Living area
2,405 sqft
Year built
1994

About this home

Set along the shores of Oyster Pond, this beautifully renovated residence embodies the timeless character of a Chatham colonial while offering the ease and comfort today's most discerning buyers expect. Wood floors, a wood-burning fireplace, and a chef's eat-in kitchen anchored by a quartz island and sunlit breakfast nook define interiors that balance heritage with refinement. A first-floor primary suite affords effortless one-level living, complemented upstairs by a second primary suite with its own ensuite bath. An additional bedroom, office, and bathroom complete the upstairs. Oyster Pond unfolds at the front of the property, while the historic Orpheum Theater comes into view from the rear, with immediate access to Main Street just steps away. Here, too, stands a rare and singular asset: the "Beach Bungalow," presently configured as additional living and entertaining space, and an invitation to bring your own imagination and vision to its continued potential. Offered in move-in condition yet rich with possibility, this is an exceptional property in an exceptional location, rewarding both the buyer seeking immediate enjoyment and the one seeking to elevate it further.

Highlights

Fireplace

Property details

MLS #
73571785
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
22
On market date
September 2, 2026
Stories
N/A
Total bathrooms
3.5
Garage spaces
N/A
Parking spaces
6
Lot size
0.44 acres
Loading map…

Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Chatham Elementary School
0.37 mi away · Grades 0-4
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
145
Student:teacher ratio
8.5:1
District
Monomoy Regional School District
Middle
Monomoy Regional Middle School
1.05 mi away · Grades 5-7
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
456
Student:teacher ratio
10.9:1
District
Monomoy Regional School District
High
Monomoy Regional High School
5.48 mi away · Grades 8-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
670
Student:teacher ratio
11.0:1
District
Monomoy Regional School District

Walkability

Blended score for Chatham's center: EPA's National Walkability Index (street network, transit, land-use mix) combined with nearby-amenity density. EPA National Walkability Index only -- nearby-amenity data not cached yet for this area.

41
Somewhat walkable
out of 100
EPA National Walkability Index
8.2 / 20 -- Below average walkable

Market position

How this listing compares to current activity in Chatham, from live MLS data.

On the market 22 days -- 109 fewer days than Chatham's current average of 131 days.
For reference, the median list price across 87 active listings in Chatham right now is $2,150,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$18,186/mo
$599,000 down
$2,396,000 loan
Principal & interest$15,540
Property tax (est.)$2,496
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 21 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.