44 Baileys Path, Chatham, MA 02633
Property image
Property image
PENDING
0.46 ACRES

$2,795,000

  • 3 Beds
  • 3.5 Baths
  • 3,514 sqft (on 0.46 acres)

44 Baileys Path, Chatham, MA 02633

Est. Mortgage $15,798/mo*
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Home Highlights

Single-Family Home
Built in 2013
0.46 acre lot
$795/sqft
2 Car Garage
HOA $125/mo

Local Information

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

About this House

Built by Eastward Companies in 2013, this thoughtfully designed, turnkey home is located in one of Chatham's highly desirable neighborhoods. Offering over 3,500 sq. ft. of beautifully appointed living space, this Cape features 3 bedrooms and 3.5 baths with an open-concept floor plan that seamlessly blends timeless Cape Cod style with modern conveniences. Filled with natural light, the spacious living room showcases cathedral ceilings and a gas fireplace, and flows effortlessly into the well-appointed kitchen and dining area. The first-floor primary suite offers privacy and comfort, while two generously sized second-floor guest bedrooms and large sitting area provide ample space for family and friends. The fully finished basement includes a beautiful in-home gym with a full bath. Quality craftsmanship is evident throughout, with hardwood floors, high-end finishes and attention to detail. Professionally landscaped grounds create a private outdoor retreat, perfect for gardening, relaxing or hosting summer gatherings. Located just moment's from Chatham's beaches, village shops and restaurants, this home offers the perfect combination of luxury, convenience and classic Cape Cod charm.
Last check for updates: about 13 hours ago
Listing courtesy of Chris Rhinesmith, (617) 967-0987
Compass Massachusetts, LLC
Source: CCIMLS, MLS#22603263
Also Listed on MLS PIN, MLS PIN, CCIMLS.

Home Details for 44 Baileys Path

Interior Features

Interior Details
Basement: FullNumber of Rooms: 7
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Appliances & Utilities
Appliances: Countertop Range, Dishwasher, Freezer, Microwave, Refrigerator, Washer, Natural Gas, Water HeaterDishwasherLaundry: Gas DryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas
Windows, Doors, Floors & Walls
Flooring: Wood, Carpet
Levels, Entrance, & Accessibility
Stories: 2Floors: Wood, Carpet

Exterior Features

Exterior Home Features
Roof: Pitched Wood Shingle
Parking & Garage
Number of Garage Spaces: 2Has a GarageHas an Attached GarageParking Spaces: 2Parking: Direct Access,Garage Door Opener,Paved
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 17Days on Market: 68

Property Information

Year Built
Year Built: 2013
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Shingle Siding
Property Information
Parcel Number: CHAT M:0007E B:007H L:00B80

Price & Status

Price
List Price: $2,795,000Price Per Sqft: $795

Active Status

MLS Status: Pending

Location

Direction & Address
City: Chatham

Agent Information

Listing Agent
Listing ID: 22603263

Building

Building Area
Building Area: 3514 Square Feet

HOA

HOA Fee Includes: Common AreaHas an HOAHOA Fee: $1,500/Annually

Lot Information

Lot Area: 0.46 acres

Listing Info

Special Conditions: None

Miscellaneous

BasementMls Number: 22603263Showing Requirements: Appointment Required, Call Listing Agent

Additional Information

HOA Amenities: Tennis Court(s)

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

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

Home Value

Trulia Estimate
$2.74M
Since last month
Increased$55K (+2%)
Since last year
Increased$579K (+26.8%)
Since last sale
Increased$2M (+196.1%)
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 +155% in the last 10 years
MonthEstimated value
2026
August 2026$2.74M
August 2026$2.74M
July 2026$2.68M
June 2026$2.33M
May 2026$2.28M
April 2026$2.28M
March 2026$2.31M
February 2026$2.25M
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
0.14
Single-Family Home
$3,025,000
12/19/25
3
3.5
3,544
40 Sam Ryder Road, Chatham, MA
0.28
Single-Family Home
$1,175,000
06/25/26
3
2
1,528
1775 Main St, Chatham, MA
0.19
Single-Family Home
$1,249,000
10/01/25
3
2
1,775
93 Stephen Drive, Chatham, MA
0.35
Single-Family Home
$835,000
10/17/25
3
2
1,144
7 Aunt Matties Road, Chatham, MA
0.13
Single-Family Home
$729,000
08/03/26
2
2
1,563
35 Oakridge Circle, Chatham, MA
0.54
Single-Family Home
$950,000
09/01/26
3
1.5
1,476
2016 Main Street, Chatham, MA
0.35
Single-Family Home
$2,025,000
10/10/25
4
4.5
3,902
20 Jessies Landing, Chatham, MA
0.64
Single-Family Home
$3,200,000
04/30/26
3
3.5
2,940
74 Deering Drive, Chatham, MA
0.76
Single-Family Home
$1,725,000
09/12/25
3
3.5
3,057
1805 Main St, Chatham, MA
0.13
Single-Family Home
$485,000
04/16/26
4
1
1,112

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
0.13
$729,000
2
2
1,563
Recently Sold
7A Malabar Road, Chatham, MA 02633
0.13
-
-
-
-
Off Market
7-7A Malabar Rd, Chatham, MA 02633
0.13
-
-
-
-
Off Market
3 Whiteleys Way, Chatham, MA 02633
0.11
$1,148,500
3
2
1,508
Off Market
23 Malabar Road, Chatham, MA 02633
0.14
$1,002,200
4
2
2,212
Off Market
1805 Main St, Chatham, MA 02633
0.13
$485,000
4
1
1,112
Recently Sold
41 Edgewood Circle, Chatham, MA 02633
0.19
$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
0.14
$3,025,000
3
3.5
3,544
Recently Sold
12 Whiteleys Way, Chatham, MA 02633
0.15
$1,477,700
3
2.5
2,620
Off Market
2 Uncle Zlotis Road, Chatham, MA 02633
0.19
$839,800
2
2
1,356
Off Market
41 Edgewood Rd, Chatham, MA 02633
0.23
$887,300
2
2
1,884
Off Market

Price and Tax history

DateEventPrice
Jul 27, 2026
Source: CCIMLS #22603263
Pending
$2,795,000
Jul 9, 2026
Source: MLS PIN #73544509
Listed For Sale
$2,795,000
Sep 16, 2013
Source: CCIMLS #21302394
Sold
$925,000
Jan 7, 2013
Source: N/A
Sold
$250,000
Oct 31, 2003
Source: N/A
Sold
$350,000

LGBTQ Local Legal Protections

Chris Rhinesmith, Compass Massachusetts, LLC
Agent Phone: (617) 967-0987
All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-09-09 11:13:16 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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Frequently asked questions about 44 Baileys Path

  • What is the estimated monthly payment for 44 Baileys Path?
    Based on a $2,795,000 list price with 20% down at today's rates, the estimated monthly payment for 44 Baileys Path in Chatham, MA is approximately $16,411 (about $14,915 principal & interest, $1,421 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 44 Baileys Path compare to homes in Chatham?
    44 Baileys Path in Chatham, MA is listed at $2,795,000, about 145% above the $1.14M median sale price in Chatham.
  • What do residents say about Chatham?
    Residents describe Chatham, MA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See homes for sale in Chatham, MA.
  • What are the closest schools to 44 Baileys Path?
    The closest schools to 44 Baileys Path in Chatham, MA are Chatham Elementary School (Pre-K, rated 8/10), Monomoy Regional High School (Middle, rated 5/10), Monomoy Regional Middle School (Elementary, rated 7/10).
  • Does 44 Baileys Path have air conditioning?
    Yes, 44 Baileys Path in Chatham, MA has air conditioning.
  • Does 44 Baileys Path have laundry facilities?
    Yes, 44 Baileys Path in Chatham, MA has laundry facilities.
44 Baileys Path, Chatham, MA 02633 is a 3 bedroom, 4 bathroom, 3,514 sqft single-family home built in 2013. This property is currently available for sale and was listed by CCIMLS on Jul 3, 2026. The MLS # for this home is MLS# 22603263.