Is parking easy in North Chatham, Chatham, MA?

As of early 2026, 100% of users say parking is easy

Would people walk alone at night in North Chatham, Chatham, MA?

As of early 2026, 100% of users say people would walk alone at night

Is a car needed in North Chatham, Chatham, MA?

As of early 2026, 100% of users say car is needed

Is North Chatham, Chatham, MA dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Is there wildlife in North Chatham, Chatham, MA?

As of early 2026, 83% of users say there's wildlife

Are neighbors friendly in North Chatham, Chatham, MA?

As of early 2026, 75% of users say neighbors are friendly

Are yards well-kept in North Chatham, Chatham, MA?

As of early 2026, 75% of users say yards are well-kept

Do residents of North Chatham, Chatham, MA plan to stay at least 5 years?

As of early 2026, 71% of users say they plan to stay for at least 5 years

Does North Chatham, Chatham, MA show holiday spirit?

As of early 2026, 60% of users say there's holiday spirit

Is North Chatham, Chatham, MA quiet?

As of early 2026, 50% of users say it's quiet

Does North Chatham, Chatham, MA have sidewalks?

As of early 2026, 50% of users say there are sidewalks

Do kids play outside in North Chatham, Chatham, MA?

As of early 2026, 40% of users say kids play outside

Is North Chatham, Chatham, MA walkable to restaurants?

As of early 2026, 29% of users say it's walkable to restaurants

Are there community events in North Chatham, Chatham, MA?

As of early 2026, 14% of users say there are community events

OFF MARKET

369 E Orleans Rd
Chatham, MA 02633

North Chatham

2 Beds
2.5 Baths
2,076 sqft (on 1.78 acres)

$782,400

Trulia Estimate

as of May 26, 2026

Est. Refi. Payment $4,384/mo*

Refinance Your Home

$782,400

Trulia Estimate

as of May 26, 2026

Est. Refi. Payment $4,384/mo*

Refinance Your Home

2 Beds

2.5 Baths

2,076 sqft

(on 1.78 acres)

Local Information

-- mins to

Commute Destination

Description

Exceptional Ryder Hollow townhome condominium! This immaculate and inviting home has been completely redone and well worth viewing with many high end finishes and security system added in 2015. The property has been professionally landscaped and maintained. When you enter the home you immediately will see how light and bright it is. Perfect floor plan that has a large sized combination living/dining room with hardwood floors, cathedral ceiling and gas log fireplace. Living area opens to an oversized deck with new awning for the relaxing while you take in the picuresque 'treehouse like' view. First and second floor master bedrooms with full private baths. The lower walkout level has been finished into a large family room space with a gas fireplace and lots of windows. There is a garage for your car plus additional parking right in front. Gas FHA heat and central a/c for comfort. One of the best Townhouse condominium values in Chatham.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

Garage

Outdoor

Deck

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

No Info

Home Details for 369 E Orleans Rd

Interior Features
Interior Details BasementAtticNumber of Rooms: 8Types of Rooms: Dining Room, Family Room, Master Bath, Recreation RoomCeiling Fan
Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 3Floors: Carpet, Hardwood
Appliances & Utilities Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace
Security Security System

Exterior Features
Exterior Home Features Roof: AsphaltDeckSprinkler System
Parking & Garage GarageParking: Garage Attached, Off Street

Property Information
Year Built Year Built: 1988Year Updated: 2015
Property Type / Style Property Type: TownhouseArchitecture: Cape Cod

Community
Units in Building: 1

Lot Information
Lot Area: 1.78 acres

Price History for 369 E Orleans Rd

Date	Price	Event	Source
04/23/2015	$487,500	Sold	CCIMLS #21409049
Recording Date 04/23/2015 County Transfer Tax N/A Total Transfer Tax N/A
09/27/2014	$499,900	Listed For Sale	Agent Provided

12/15/2011	$520,000	ListingRemoved	Agent Provided

08/04/2011	$520,000	Listed For Sale	Agent Provided

06/28/2011	$520,000	ListingRemoved	Agent Provided

10/30/2010	$520,000	Listed For Sale	Agent Provided

03/15/2006	$475,000	Sold	N/A
Recording Date 03/15/2006 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$1,850
Assessment	$533,100

Home facts updated by county records

Comparable Sales for 369 E Orleans Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
369 E Orleans Rd #A, Chatham, MA	0.01	Townhouse	$615,300	05/27/25	2	2.5	1,283
369 Orleans Road #A, North Chatham, MA	0.51	Townhouse	$615,300	05/27/25	2	2.5	1,283
1082 Main St #1082, Chatham, MA	1.00	Townhouse	$950,000	08/07/25	2	3	2,399
158 Eaton Lane, Brewster, MA	5.64	Townhouse	$350,000	07/25/25	2	2	935
288 Fletcher Ln #288, Brewster, MA	5.77	Townhouse	$495,000	09/02/25	2	1.5	1,032
258 Fletcher Lane, Brewster, MA	5.80	Townhouse	$515,000	08/06/25	2	2	1,164
258 Fletcher Ln #15, Brewster, MA	5.80	Townhouse	$515,000	08/06/25	2	2	1,164
286 Fletcher Ln #286, Brewster, MA	5.77	Townhouse	$525,000	08/29/25	2	2	1,063
286 Fletcher Lane, Brewster, MA	5.79	Townhouse	$525,000	08/29/25	2	2	1,063
290 Fletcher Ln #290, Brewster, MA	5.77	Townhouse	$670,000	08/29/25	2	2	1,164

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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FOR SALE
NEW - 2 DAYS AGO
3D VIEW
0.47 ACRES
$1,349,000
3 bd
3 ba
2,268 sqft
36 Pursel Drive,
North Chatham, MA 02650
Gibson Sotheby's International Realty
FOR SALE
NEW - 2 DAYS AGO
0.36 ACRES
$1,199,900
2 bd
1.5 ba
1,324 sqft
99 Shane Drive,
Chatham, MA 02633
Christie's International Real Estate Atlantic Brokerage
FOR SALE
0.37 ACRES
$900,000
2 bd
1 ba
864 sqft
66 Snow Lane,
Chatham, MA 02633
Compass
FOR SALE
$2,350,000
3 bd
3 ba
2,212 sqft
320 Old Harbor Road,
Chatham, MA 02633
Berkshire Hathaway HomeServices Robert Paul Properties
FOR SALE
0.5 ACRES
$4,595,000
5 bd
3.5 ba
2,659 sqft
92 Barcliff Avenue,
Chatham, MA 02633
Gibson Sotheby's International Realty
FOR SALE
$1,289,900
2 bd
2.5 ba
3,094 sqft
41 Misty Meadow Lane UNIT B,
North Chatham, MA 02650
Tom Hester Real Estate
FOR SALE
0.32 ACRES
$4,950,000
4 bd
4.5 ba
5,371 sqft
15 Bay Lane,
Chatham, MA 02633
Compass Massachusetts, LLC
FOR SALE
$899,000
2 bd
2 ba
2,127 sqft
1068 Main St #1068,
Chatham, MA 02633
Kristin Coletti, William Raveis R.E. & Home Services
FOR SALE
0.5 ACRES
$3,695,000
3 bd
4.5 ba
5,154 sqft
83 Old Mail Road,
North Chatham, MA 02650
Compass Massachusetts, LLC
FOR SALE
0.5 ACRES
$865,900
2 bd
2 ba
1,688 sqft
61 Oak Hill Road,
Chatham, MA 02633
Christie's International Real Estate Atlantic Brokerage
FOR SALE
0.67 ACRES
$1,650,000
3 bd
2 ba
2,169 sqft
48 Glover Square,
Chatham, MA 02633
Gibson Sotheby's International Realty
SOLD
APR 29, 2026
$1,400,000
3 bd
2 ba
1,420 sqft
1239 Main Street UNIT 18,
Chatham, MA 02633
Berkshire Hathaway HomeServices Robert Paul Properties

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Additional Cost

Assigned Schools

These are the assigned schools for 369 E Orleans Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

North Chatham

10 Homes For You
Buy: $475k - $13m

See Local Highlights

Neighborhood stats provided by third party data sources.

What Locals Say about North Chatham

At least 2 Trulia users voted on each feature.

100 % Say parking is easy
100 % Say people would walk alone at night
100 % Say car is needed
100 % Say it's dog friendly
83 % Say there's wildlife
75 % Say neighbors are friendly
75 % Say yards are well-kept
71 % Say they plan to stay for at least 5 years
60 % Say there's holiday spirit
50 % Say it's quiet
50 % Say there are sidewalks
40 % Say kids play outside
29 % Say it's walkable to restaurants
14 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Snbrinc
Resident
2y ago
"I’m 4th generation living in this neighborhood. Very special highly desirable place. Proud to be a native. "
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Apartments for Rent

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Contact for price
1-2 bd
1-2 ba
390 Orleans Rd #776f18ccb,
North Chatham, MA 02650
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Chatham
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Homes for sale near 369 E Orleans Rd

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$899,000
2 bd
2 ba
2,127 sqft
1068 Main St #1068,
Chatham, MA 02633
Kristin Coletti, William Raveis R.E. & Home Services
$449,000
2 bd
2.5 ba
1,121 sqft
724 Route 28 APT 2D,
Harwich Port, MA 02646
LPT Realty
$795,000
2 bd
1.5 ba
1,253 sqft
4 Center Place UNIT 11,
Orleans, MA 02653
William Raveis Real Estate & Home Services
$499,000
2 bd
2 ba
1,063 sqft
210 Billington Lane UNIT 210,
Brewster, MA 02631
Keller Williams Realty
$419,000
2 bd
1.5 ba
1,296 sqft
81 Woodview Drive UNIT 81,
Brewster, MA 02631
Keller Williams Realty
See more homes for sale in
Chatham
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Off Market Homes Near 369 E Orleans Rd

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SOLD
MAY 22, 2026
$1,150,000
3 bd
2.5 ba
2,866 sqft
63 Idle Way,
Harwich, MA 02645
Corcoran Property Advisors
SOLD
MAY 21, 2026
$660,000
3 bd
2 ba
1,192 sqft
62 Continental Drive,
Harwich, MA 02645
Kinlin Grover Compass
SOLD
MAY 20, 2026
$562,000
3 bd
1 ba
1,404 sqft
1157 Orleans-Harwich Road,
Harwich, MA 02645
Compass
SOLD
MAY 18, 2026
$889,000
4 bd
2 ba
2,004 sqft
25 Wood Valley Road,
Chatham, MA 02633
Christie's International Real Estate Atlantic Brokerage
SOLD
MAY 18, 2026
$1,150,000
3 bd
3 ba
2,212 sqft
122 Evelyn's Drive,
Brewster, MA 02631
Compass
SOLD
MAY 15, 2026
$1,050,000
4 bd
2 ba
2,148 sqft
298 Chippingstone Road,
Chatham, MA 02633
Keller Williams Realty
SOLD
MAY 15, 2026
$995,000
3 bd
3 ba
2,067 sqft
2084 Route 28 Head Of The Bay Road,
Harwich, MA 02645
Gibson Sotheby's International Realty
SOLD
MAY 15, 2026
$995,000
3 bd
3 ba
2,067 sqft
2084 Highway 28,
Harwich, MA 02645
Jean Piazza, Gibson Sotheby's International Realty
SOLD
MAY 15, 2026
$1,050,000
4 bd
2 ba
2,148 sqft
298 Chipping Stone Rd,
Chatham, MA 02633
Robert Bantick, Keller Williams Realty
SOLD
MAY 8, 2026
$865,000
3 bd
2 ba
1,999 sqft
54 Marthas Lane,
Harwich, MA 02645
Gibson Sotheby's International Realty
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Chatham
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Homes for rent near 369 E Orleans Rd

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$20,000/mo
Fees may apply
4 bd
2 ba
2,000 sqft
101A Monomoyic Way,
Chatham, MA 02633
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Chatham
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369 E Orleans Rd, Chatham, MA 02633 is a 2 bedroom, 3 bathroom, 2,076 sqft townhouse built in 1988. 369 E Orleans Rd is located in North Chatham, Chatham. This property is not currently available for sale. 369 E Orleans Rd was last sold on Apr 23, 2015 for $487,500. The current Trulia Estimate for 369 E Orleans Rd is $782,400.

369 E Orleans Rd
Chatham, MA 02633

$782,400

$782,400

Local Information