5

South Chatham Homes for Sale

Section Image
  • 124 Pleasant St, South Chatham, MA 02659
    124 Pleasant St, South Chatham, MA 02659
    124 Pleasant St, South Chatham, MA 02659
    /60

    $1,495,000

    Open Sat 1:30PM - 3:30PM
    • 3 Beds
    • 3 Baths
    • 1,771 Sq Ft

    124 Pleasant St, South Chatham, MA 02659

    This is the South Chatham beach house everyone is looking for! Fully renovated and turnkey, 124 Pleasant Street is ready for immediate enjoyment -- as a private retreat of your own, or as a proven, guest-favorite rental. A short walk to Pleasant Street Beach, this South Chatham location grows only more desirable year over year. The living room, anchored by a fireplace, flows into the dining room

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    124 Pleasant St, South Chatham, MA 02659
  • 50 Sylvan Way, South Chatham, MA 02659
    50 Sylvan Way, South Chatham, MA 02659
    /2

    $5,900,000

    • 6 Beds
    • 8 Baths
    • 6,183 Sq Ft

    50 Sylvan Way, South Chatham, MA 02659

    The newest release within a private gated enclave in South Chatham's emerging luxury corridor, 50 Sylvan Way is a bespoke custom estate minutes from the Cape's most iconic downtowns, beaches, and dining, yet removed enough to feel like a world apart. Thirteen rooms across over 6000 square feet of living space sited on 1.635 bucolic acres. A first-floor primary wing. Three-car garage. Every

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    50 Sylvan Way, South Chatham, MA 02659
  • 70 Uncle Deane's Rd, Chatham, MA 02659
    70 Uncle Deane's Rd, Chatham, MA 02659
    70 Uncle Deane's Rd, Chatham, MA 02659
    /39

    $1,999,000

    Open Sun 11:30AM - 1PM
    • 3 Beds
    • 3 Baths
    • 3,514 Sq Ft

    70 Uncle Deane's Rd, Chatham, MA 02659

    Unique post-and-beam masterpiece, blending rustic character with modern comfort. This dramatic home showcases soaring cathedral ceilings, exposed timber framing, and an open lofted design with stained glass windows, creating an impressive sense of space and light. Rich wood details and crisp white walls create a timeless balance of warmth, craftsmanship, and coastal elegance. Thoughtfully

    Patrick Davison Shining Sea Realty

    70 Uncle Deane's Rd, Chatham, MA 02659
  • 48 Sylvan Way, South Chatham, MA 02659
    48 Sylvan Way, South Chatham, MA 02659
    48 Sylvan Way, South Chatham, MA 02659
    /72

    $4,750,000

    New Construction Open Tue 4PM - 6PM $500K PRICE DROP
    • 6 Beds
    • 7 Baths
    • 5,721 Sq Ft

    48 Sylvan Way, South Chatham, MA 02659

    Set within a private gated enclave in South Chatham's emerging luxury corridor, 48 Sylvan Way is a singular estate retreat discreetly positioned just moments from the Cape's most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational potential, the property offers rare privacy, scale, and versatility in one of Chatham's most compelling

    Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

    48 Sylvan Way, South Chatham, MA 02659
  • 22 Country Ln, South Chatham, MA 02659
    22 Country Ln, South Chatham, MA 02659
    22 Country Ln, South Chatham, MA 02659
    /39

    $699,900

    • 2 Beds
    • 1 Bath
    • 572 Sq Ft

    22 Country Ln, South Chatham, MA 02659

    Just 0.4 miles from the sandy shores of Pleasant Street Beach, this enchanting South Chatham Cape-style cottage captures the timeless charm of Cape Cod living. Set down a private lane on a tree-lined lot, this storybook home is filled with warmth and character. The sun-filled interior features an open living and dining area heated by a cozy natural gas stove, a cheerful kitchen with a butcher

    Laurie Miller Sotheby's International Realty, Inc.

    22 Country Ln, South Chatham, MA 02659
Massachusetts Barnstable County Chatham

Real Estate & Homes for Sale in South Chatham, Chatham

Why Live in South Chatham
South Chatham sits at the bottom of the “elbow” of Cape Cod, with the landform’s northward turn in one direction and the vast expanse of the Atlantic Ocean to the other. Homes are interwoven with small ponds, and some are walking distance from ...
Learn more about living in South Chatham

South Chatham Home Prices vs. Nearby Chatham, MA Neighborhoods

South Chatham North Chatham Orleans
Median Home Price
$1,250,000
$1,495,000
$1,000,000
Median Sale Price
$1,100,000
-23% YoY
$1,330,000
-1% YoY
$821,250
-15% YoY
Median Single Family Price
$1,125,000
$1,495,000
$1,250,000
Median Townhouse Price
$1,500,000
$349,999
--
Median Condo Price
$1,695,000
$989,450
$360,000
Total Active Listings
10 listings
24 listings
59 listings
Market Conditions
2 Months of Supply
Seller's Market
3 Months of Supply
Seller's Market
4 Months of Supply
Balanced Market

Frequently Asked Questions

Is South Chatham a good place to live?
South Chatham is a good place to live. South Chatham is considered very car-dependent and somewhat bikeable with minimal transit options. South Chatham is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. It has a median age of 61. The average household income is $112,884 which is above the national average. College graduates make up 56.9% of residents. A majority of residents in South Chatham are home owners, with 14% of residents renting and 86% of residents owning their home. A local real estate agent serving South Chatham can help you decide if this neighborhood is the right one for you. Learn more on our South Chatham neighborhood guide.
Is South Chatham, MA a safe neighborhood?
South Chatham, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in South Chatham?
The median home price in South Chatham is $1,250,000. If you put a 20% down payment of $250,000 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $6,430 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $276K a year to afford the median home price in South Chatham. Learn how much home you can afford with our Home Affordability Calculator. The average household income in South Chatham is $113K.
What are the best public schools in South Chatham?
The best public schools that serve South Chatham are:
What are the most popular zip codes in South Chatham, Chatham, MA?
The most popular zip codes in South Chatham, Chatham, MA include 02659, 02645, 02633, 02646 and 02650.
What are the most popular neighborhoods near South Chatham, Chatham, MA?
The most popular neighborhoods near South Chatham, Chatham, MA are Harwich Port, West Chatham, East Harwich, North Chatham and Chatham Village.
Are home prices dropping in South Chatham?
Yes, home prices in South Chatham are down 15% in the last 12 months.
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group