65 Baileys Path, Chatham, MA 02633
OFF MARKET

$2,357,400

Trulia Estimate
  • 3 Beds
  • 4.5 Baths
  • 3,800 sqft (on 0.47 acres)

65 Baileys Path, Chatham, MA 02633

Est. Refi. Payment $13,193/mo*
Refinance Your Home
Currently Off Market - Sold Dec 16, 2011 for $870,000

Home Value

Trulia Estimate
$2.36M
Since last month
Decreased$34K (-1.4%)
Since last year
Increased$218K (+10.2%)
Since last sale
Increased$1M (+171%)
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 +114% in the last 10 years
MonthEstimated value
2026
August 2026$2.36M
August 2026$2.35M
July 2026$2.39M
June 2026$2.38M
May 2026$2.35M
April 2026$2.34M
March 2026$2.28M
February 2026$2.24M
January 2026$2.22M
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
93 Bucks Creek Road, Chatham, MA
0.18
Single-Family Home
$3,025,000
12/19/25
3
3.5
3,544
40 Sam Ryder Road, Chatham, MA
0.30
Single-Family Home
$1,175,000
06/25/26
3
2
1,528
2016 Main Street, Chatham, MA
0.37
Single-Family Home
$2,025,000
10/10/25
4
4.5
3,902
93 Stephen Drive, Chatham, MA
0.40
Single-Family Home
$835,000
10/17/25
3
2
1,144
1775 Main St, Chatham, MA
0.22
Single-Family Home
$1,249,000
10/01/25
3
2
1,775
7 Aunt Matties Road, Chatham, MA
0.14
Single-Family Home
$729,000
08/03/26
2
2
1,563
35 Oakridge Circle, Chatham, MA
0.58
Single-Family Home
$950,000
09/01/26
3
1.5
1,476
20 Jessies Landing, Chatham, MA
0.66
Single-Family Home
$3,200,000
04/30/26
3
3.5
2,940
29 Jessies Landing, Chatham, MA
0.67
Single-Family Home
$3,699,900
06/30/26
3
4.5
4,565
74 Deering Drive, Chatham, MA
0.80
Single-Family Home
$1,725,000
09/12/25
3
3.5
3,057

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
7 Aunt Matties Road, Chatham, MA 02633
0.14
$729,000
2
2
1,563
Recently Sold
7A Malabar Road, Chatham, MA 02633
0.15
-
-
-
-
Off Market
7-7A Malabar Rd, Chatham, MA 02633
0.15
-
-
-
-
Off Market
3 Whiteleys Way, Chatham, MA 02633
0.15
$1,148,500
3
2
1,508
Off Market
23 Malabar Road, Chatham, MA 02633
0.16
$1,002,200
4
2
2,212
Off Market
1805 Main St, Chatham, MA 02633
0.17
$485,000
4
1
1,112
Recently Sold
41 Edgewood Circle, Chatham, MA 02633
0.17
$1,041,800
2
2
1,884
Off Market
8 Uncle Zlotis Road, Chatham, MA 02633
0.19
$989,700
3
1.5
1,890
Off Market
93 Bucks Creek Road, Chatham, MA 02633
0.18
$3,025,000
3
3.5
3,544
Recently Sold
12 Whiteleys Way, Chatham, MA 02633
0.19
$1,477,700
3
2.5
2,620
Off Market
2 Uncle Zlotis Road, Chatham, MA 02633
0.20
$839,800
2
2
1,356
Off Market
1772 Main Street, Chatham, MA 02633
0.20
$699,999
Studio
0.5
600
For Sale

Local Information

  • Map ViewExplore the area around 65 Baileys Path.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2005
Lot Size
0.47 acres
Living Area
3,800 sqft
Price/Sqft
$620
Parking
Garage

About this House

CHATHAM:This Exquisite 3 Bedroom 3.5 Home built by Eastward CO in Baileys Path has unrivaled attention to detail and Cape Cod charm thru out!! The 3200 sq ft Home features 3 fireplaces,Great room with Gourmet Kitchen complete with Viking Stove, Island,& extensive Cabinetry. There are multiple living areas including a private Bonus room with full Bath,Den,& Lovely Sunroom that leads to a deck and patio,all surrounded with mature landscaping that affords much privacy! Private Tennis and walk to the Bike Path! Perfect for a Pool!!$999,950
65 Baileys Path, Chatham, MA 02633 is a 3 bedroom, 5 bathroom, 3,800 sqft single-family home built in 2005. It last sold for $870,000 on Dec 16, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,357,400, with a rent estimate of $6,972/month.

Home Details for 65 Baileys Path

Interior Features

Interior Details
BasementAtticNumber of Rooms: 11Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Recreation Room, Sun 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
FireplaceHot Tub or Spa
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Shingle, WoodLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 5Parking: Garage Attached

Property Information

Year Built
Year Built: 2005Year Updated: 2025
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 0.47 acres

Additional Information

Sport Court

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Dec 16, 2011
Source: CCIMLS #21102562
Sold
$870,000
Jul 20, 2011
Source: Agent Provided
Listed For Sale
$999,950
Oct 5, 2005
Source: N/A
Sold
$900,000

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 65 Baileys Path

  • What is 65 Baileys Path estimated to be worth?
    Trulia's estimated value for 65 Baileys Path in Chatham, MA is $2,357,400.
  • What is the price history for 65 Baileys Path?
    65 Baileys Path in Chatham, MA last sold for $870,000 in December 2011.
  • 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 65 Baileys Path have air conditioning?
    Yes, 65 Baileys Path in Chatham, MA has air conditioning.
  • Does 65 Baileys Path have a pool?
    Yes, 65 Baileys Path in Chatham, MA has a pool.

Explore by feature - Air Conditioning

6 rentals with air conditioning in Chatham, MA

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Chatham, MA

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