369 E Orleans Rd, Chatham, MA 02633
Property image
Property image
OFF MARKET

369 E Orleans Rd
Chatham, MA 02633

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

$788,700

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $4,448/mo*
Refinance Your Home

$788,700

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $4,448/mo*
Refinance Your Home
2 Beds
2.5 Baths
2,076 sqft
(on 1.78 acres)

Home Value

Trulia Estimate
$789K
Since last month
Increased$1K (+0.2%)
Since last year
Increased$32K (+4.2%)
Since last sale
Increased$308K (+63.3%)
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 +55% in the last 10 years
MonthEstimated value
2026
August 2026$796K
July 2026$795K
June 2026$801K
May 2026$775K
April 2026$778K
March 2026$782K
February 2026$754K
January 2026$759K
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
288 Fletcher Ln #288, Brewster, MA
5.77
Townhouse
$495,000
09/02/25
2
1.5
1,032
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
287 Fletcher Lane UNIT 287, Brewster, MA
5.93
Townhouse
$450,000
06/12/26
2
1.5
1,032
288 Fletcher Lane, Brewster, MA
6.04
Townhouse
$495,000
09/02/25
2
1.5
1,032
63 Trevor Lane UNIT 63, Brewster, MA
6.04
Townhouse
$480,000
03/05/26
2
1.5
1,032
14 Howland Cir, Brewster, MA
6.04
Townhouse
$555,000
03/26/26
2
2
1,164
14 Howland Circle UNIT 14, Brewster, MA
6.04
Townhouse
$555,000
03/26/26
2
2
1,164
61 Trevor Ln #55, Brewster, MA
6.04
Townhouse
$540,000
06/16/26
2
2
1,063

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
369 E Orleans Rd #A, Chatham, MA 02633
0.01
-
2
2.5
1,283
Off Market
36 Misty Meadow Lane #1, North Chatham, MA 02650
0.05
$561,800
1
1.5
836
Off Market
369 Orleans Road #E, Chatham, MA 02633
0.02
$919,100
2
2.5
1,934
Off Market
36 Misty Meadow Lane #4, North Chatham, MA 02650
0.05
$424,800
2
1.5
930
Off Market
37 Misty Meadow Lane #B, North Chatham, MA 02633
0.05
$1,097,800
2
2.5
1,906
Off Market
39 Misty Meadow Ln, Chatham, MA 02633
0.06
$1,119,900
2
2.5
1,812
Off Market
37 Misty Meadow Lane #43A, Chatham, MA 02633
0.06
$1,238,500
2
2.5
2,060
Off Market
37 Misty Meadow Lane #41A, Chatham, MA 02633
0.06
$1,207,600
2
2.5
2,060
Off Market
108 Misty Meadow Ln #A, North Chatham, MA 02650
0.06
$591,900
2
2
1,489
Off Market
108 Misty Meadow Ln #B, North Chatham, MA 02650
0.06
$688,400
2
2
1,551
Off Market
108 Misty Meadow Lane #XB, North Chatham, MA 02650
0.06
$764,000
2
2
1,551
Off Market
347 Orleans Road, North Chatham, MA 02650
0.06
$1,154,200
3
1.5
1,258
Off Market

Local Information

  • Map ViewExplore the area around 369 E Orleans Rd.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Year Built
1988
Lot Size
1.78 acres
Living Area
2,076 sqft
Price/Sqft
$380
Parking
Garage

About this House

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.
369 E Orleans Rd, Chatham, MA 02633 is a 2 bedroom, 3 bathroom, 2,076 sqft townhouse in North Chatham, built in 1988. It last sold for $487,500 on Apr 23, 2015. It is currently off market. The Trulia Estimate is $788,700, with a rent estimate of $3,634/month.

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 and Tax history

DateEventPrice
Apr 23, 2015
Source: CCIMLS #21409049
Sold
$487,500
Sep 27, 2014
Source: Agent Provided
Listed For Sale
$499,900
Dec 15, 2011
Source: Agent Provided
ListingRemoved
$520,000
Aug 4, 2011
Source: Agent Provided
Listed For Sale
$520,000
Jun 28, 2011
Source: Agent Provided
ListingRemoved
$520,000

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

Neighborhood Overview

North Chatham
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
    "I’m 4th generation living in this neighborhood. Very special highly desirable place. Proud to be a native. "
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 369 E Orleans Rd

  • What is 369 E Orleans Rd estimated to be worth?
    Trulia's estimated value for 369 E Orleans Rd in Chatham, MA is $788,700.
  • What is the price history for 369 E Orleans Rd?
    369 E Orleans Rd in Chatham, MA last sold for $487,500 in April 2015.
  • 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 369 E Orleans Rd have air conditioning?
    Yes, 369 E Orleans Rd in Chatham, MA has air conditioning.
  • Does 369 E Orleans Rd have laundry facilities?
    Yes, 369 E Orleans Rd in Chatham, MA has in-unit laundry.

Explore by feature - Air Conditioning

Explore by feature - Washer/dryer

Apartments for Rent

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Off Market Homes Near 369 E Orleans Rd

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