Chatham, MA Homes

/6
$250,000
- Land
- 0.72 Acre
- $347,222 per Acre
0 George Ryder Rd Unit 73104629, Chatham, MA 02633

Amazing opportunity to build your dream home in Chatham on this .72-acre, panhandle, private residential lot. Build a 3-bedroom home connected to town sewer, 4-bedroom with approval. (buyer's & buyer's agents verify with Board of Health). The water, gas, electric, cable and sewer are on George Ryder Road. This property is convenient to shopping, seven restaurants, the bike path, a medical office,

Shane Masaschi

Compass

(508) 691-8324

0 George Ryder Rd Unit 73104629, Chatham, MA 02633
/24
$3,500 total monthly price
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
- House for Rent
181 George Ryder Rd, Chatham, MA 02633

Year round rental; 3BR 2BA Cape Cod home in Chatham is available starting Jan 1st, 2026. Larger private lot, gas heat, 1 car garage, full basement. Mass Save insulation upgrade. Near Bike trail giving easy access to other Chatham points of interest. Required: Rents: 1st and last month's plus security with the lease. Full tenant screening required. Available Jan 1st, 2026. List agent is related to

Christopher Coy Realty Executives Cape Cod

181 George Ryder Rd, Chatham, MA 02633
/42
$1,695,000 Sold Oct 31, 2025
- 1,320 Sq Ft
- $1,284/SF
- 40 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1950
34 Sea Mist Ln, South Chatham, MA 02659

Exceptional views of Nantucket Sound and Deeded rights to a private beach just steps away make this fully renovated three bedroom home truly exceptional. Styled with a coastal aesthetic, the interior features designer finishes that evoke the relaxed elegance of oceanside living. Step outside to enjoy an expansive outdoor living area, complete with a natural gas fire table, an outdoor shower and

Rick Smith Gibson Sotheby's International Realty

34 Sea Mist Ln, South Chatham, MA 02659

/30
Not Listed For Sale
- 2 Beds
- 1 Bath
- 772 Sq Ft
25 Bobbie's Ln, Chatham, MA 02659

25 Bobbie's Ln, Chatham, MA 02659

/41
$1,295,000 Pending
- 3 Beds
- 2 Baths
- 1,634 Sq Ft
79 Forest Beach Rd, South Chatham, MA 02659

Endless Summer Awaits at 79 Forest Beach Road, South Chatham! A 3 bed, 2 bath bungalow beauty is the coastal escape you've been waiting for. Tucked just south of Route 28 and only .04 miles to sandy Forest Beach, set on an oversized 42,688 sq ft lot. Inside, you'll love the bright and breezy layout, updated kitchen, and baths, & comfort all year long with a high-efficiency 95% combo 2-zone Rinnai

Shane Masaschi

Compass

(508) 978-3555

79 Forest Beach Rd, South Chatham, MA 02659
/27
$3,200 total monthly price
- 2 Beds
- 2 Baths
- 1,949 Sq Ft
- House for Rent
70 Barn Hill Rd, Chatham, MA 02633

Newly built ready for immediate occupancy!!! This nicely built 2 bedroom 2 bath house comes fully furnished and is located in beautiful Chatham! Featuring an open floor plan with one bedroom and full bath on the first floor along with another bedroom and full bath on the second floor. There are high cathedral ceilings in the main living area featuring large windows for lots of natural light.

Kevin Austin William Raveis Real Estate & Home Services

70 Barn Hill Rd, Chatham, MA 02633
/48
$2,450,000 Sold Oct 31, 2025
- 3,275 Sq Ft
- $748/SF
- 3 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2007
252 N Skyline Dr, Chatham, MA 02633

Catch the breezes atop Great Hill in this centrally located classic Cape with deeded rights to Lovers Lake. Updated with flair, this 8-room home offers 3275 sq ft. of living space & is perfectly nestled on a professionally landscaped lot. The home has a great floor plan that will surprise and delight you with unique & pizazz-y features. Whether year-round, or summer living, this beautifully

Phyllis Power Compass

252 N Skyline Dr, Chatham, MA 02633

/4
Est $2,916,296 Not Listed For Sale
- 3 Beds
- 5.5 Baths
- 4,197 Sq Ft
21 Hunter Rise, Chatham, MA 02633

21 Hunter Rise, Chatham, MA 02633

/16
$605,000 Pending
- Land
- 0.7 Acre
- $864,286 per Acre
Lot 6 Bobbie's Ln, Chatham, MA 02659

Build your Cape Cod Dream! Opportunity awaits on picturesque Bobbies Lane. This generously sized 30,150 sq ft building lot, located south of Route 28, offers the perfect canvas for your Cape Cod getaway or year-round residence. Just 0.4 miles to stunning Forest Beach, you'll enjoy easy strolls to one of the most scenic and serene beaches on Nantucket Sound. Imagine building a charming 3-bedroom

Shane Masaschi

Compass

(508) 738-3104

Lot 6 Bobbie's Ln, Chatham, MA 02659
/19
$4,950 total monthly price
- 4 Beds
- 2 Baths
- 2,000 Sq Ft
- House for Rent
101 Monomoyic Way, Chatham, MA 02633

Available furnished rental September 15 - April 30! Relax with the whole family at this peaceful place to stay. A stunning, fresh, contemporary home in Chatham! Perched upon a gentle hill at the very end of a cul-de-sac in Riverbay Estates, this home has undergone a total makeover. Airy and open, with soaring ceilings, designer Tala lights and a dramatic limestone gas fireplace that accentuate

Steven Cohen Team Keller Williams Realty Boston-Metro | Back Bay

101 Monomoyic Way, Chatham, MA 02633
/34
$674,000 Sold Oct 31, 2025
- 1,244 Sq Ft
- $542/SF
- 6 Days On Market
- 2 Beds
- 1 Bath
- Built 1982
38 Andover Dr, Chatham, MA 02633

Don't miss this lovely 2 Bedroom, 1 Bath Cape-style ranch in well-groomed residential neighborhood near town. As part of Great Hills Estates, this property has deeded rights to Lover's Lake including water access, picnic & BBQ area, and kayak racks. Enjoy sidewalk access to Town, easy proximity to the Chatham Bike Path, and a location just 2 miles to Hardings Beach. Inside, the main level offers

Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

38 Andover Dr, Chatham, MA 02633

/54
Est $3,892,357 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,751 Sq Ft
110 Sea Shells Dr, South Chatham, MA 02659

110 Sea Shells Dr, South Chatham, MA 02659

/32
$799,900 Open Sat 1PM - 3PM
- 2 Beds
- 2 Baths
- 868 Sq Ft
47 Cranberry Way, South Chatham, MA 2659

Tucked away on a picturesque side street off Cockle Cove Road in Chatham, this delightful 2-bedroom, 2-bath home is full of coastal charm.Step through the front door into a warm, inviting living room complete with wood floors and a cozy fireplace -- perfect for relaxing evenings. Just off the living area, there's space for a dining nook, while the kitchen sits at the back of the home, offering

William Raye

Gibson Sotheby's International Realty

(508) 432-7856

47 Cranberry Way, South Chatham, MA 2659
/76
$3,675,000 Sold Oct 31, 2025
- 4,908 Sq Ft
- $749/SF
- 455 Days On Market
- 4 Beds
- 5.5 Baths
- Built 2025
45 Meadow View Rd S, Chatham, MA 02633

New construction and a deeded boat slip in the Oyster River Hills private neighborhood marina. Another magnificent home by Sears Point Residential, move-in ready. 4 BR, 5.5 Bath, 4,908 sf classic shingle-style Cape. The home's axis is a chef's kitchen featuring Thermador appliances and a large center island with Quartz countertops. The open floor plan flows seamlessly from the living room to the

Jack Bohman Gibson Sotheby's International Realty

45 Meadow View Rd S, Chatham, MA 02633

/51
Est $2,897,101 Not Listed For Sale
- 6 Beds
- 4 Baths
- 4,449 Sq Ft
114 Main St, Chatham, MA 02633

114 Main St, Chatham, MA 02633

/34
$799,900 Open Sat 1PM - 3PM
- 2 Beds
- 2 Baths
- 868 Sq Ft
47 Cranberry Way, Chatham, MA 02659

Charming Coastal Retreat...Tucked away on a picturesque side street off Cockle Cove Road, this delightful 2-bedroom, 2-bath home is full of coastal charm! Step through the front door and into a warm, inviting living room complete with wood floors and a cozy fireplace — perfect for relaxing evenings. Just off the living area, there's space for a dining nook, while the well-appointed kitchen sits

William Raye

Gibson Sotheby's International Realty

(508) 290-7066

47 Cranberry Way, Chatham, MA 02659
/41
$898,000 Sold Oct 30, 2025
- 1,680 Sq Ft
- $535/SF
- 14 Days On Market
- 4 Beds
- 2 Baths
- Built 1966
306 Old Queen Anne Rd, Chatham, MA 02633

Cape Cod living made easy in this beautifully updated 4-bedroom, 2-bathroom Cape nestled in the desirable Great Hill Estates neighborhood, less than a mile from downtown Chatham. Thoughtfully renovated throughout, this home blends modern updates with timeless Cape charm.The inviting floor plan features a bright living area, a well-appointed kitchen with quality finishes, and four comfortable

Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

306 Old Queen Anne Rd, Chatham, MA 02633

/42
Est $8,180,808 Not Listed For Sale
- 8 Beds
- 5.5 Baths
- 4,859 Sq Ft
504 Old Harbor Rd, North Chatham, MA 02650

504 Old Harbor Rd, North Chatham, MA 02650

/55
$3,200,000 Open Sat 12:30PM - 2PM
- 3 Beds
- 3.5 Baths
- 3,544 Sq Ft
93 Bucks Creek Rd, Chatham, MA 02633

Welcome to 93 Bucks Creek Rd, where luxury meets coastal elegance. This architecturally stunning, custom-built home offers an unparalleled resort-style experience boasting a heated, saltwater pool and membership to the exclusive Hardings Hills Association, featuring a private dock, kayak storage, & picnic area. Nestled just 3/10ths of a mile from the pristine sands of Hardings Beach, this

Shane Masaschi

Compass

(508) 571-0968

93 Bucks Creek Rd, Chatham, MA 02633
/42
$2,325,000 Sold Oct 30, 2025
- 3,226 Sq Ft
- $721/SF
- 13 Days On Market
- 3 Beds
- 4 Baths
- Built 2014
94 Ocean Port Ln, Chatham, MA 02633

Built in 2014, this beautifully designed home offers 3 bedrooms, 4 full baths, and over 3,400 sq. ft. of living space, including a finished basement and a bonus room above the detached garage. Hardwood floors flow throughout the open layout, where you'll find a chef ready kitchen, sun-filled living room with coffered ceilings and gas fireplace. The first floor is completed by a full bath, laundry

The Bohman Hartung Group Gibson Sotheby's International Realty

94 Ocean Port Ln, Chatham, MA 02633

/37
Est $2,525,894 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,203 Sq Ft
47 Gladen Ln, Chatham, MA 02633

47 Gladen Ln, Chatham, MA 02633

/81
$4,900,000
- 4 Beds
- 4.5 Baths
- 2,850 Sq Ft
346 Morris Island Rd, Chatham, MA 02633

Views, Views, Views!! Sun splashed Stage Harbor waterfront offering and ever-changing vista out to Nantucket Sound and beyond. This four bedroom, 4.5 bath residence blends exquisite taste with timeless coastal elegance. Thoughtfully renovated, the home is designed to showcase wide, sweeping views of the harbor from nearly every room. Light-filled interiors pair refined finishes with a relaxed

Barbara Garside

eXp Realty, LLC

(508) 401-8501

346 Morris Island Rd, Chatham, MA 02633
/40
$2,400,000 Sold Oct 30, 2025
- 3,603 Sq Ft
- $666/SF
- 246 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2005
290 Old Comers Rd, Chatham, MA 02633

''On Pink Wink Pond'' embodies the essence of Cape Cod. A startling entrance of Belgian blocks with carriage lighted and stone pillars greets the visitor. Ascending the farmers porch and upon entry, an illuminated tile mural of Pink Wink Pond boasts the home's attention to artistic detail. The two-story windowed great room is surrounded by crystal blue shiplap and offers a gas fireplace. Sub-Zero

Catherine Baran Berkshire Hathaway HomeServices Robert Paul Properties

290 Old Comers Rd, Chatham, MA 02633

/12
Est $6,270,619 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,286 Sq Ft
486 Shore Rd, Chatham, MA 02633

486 Shore Rd, Chatham, MA 02633

/50
$5,495,000
- 6 Beds
- 7 Baths
- 5,721 Sq Ft
48 Sylvan Way, South Chatham, MA 02659

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel of

Chris Olson

eXp Realty, LLC

(508) 715-6571

48 Sylvan Way, South Chatham, MA 02659
/36
$1,195,000 Sold Oct 26, 2025
- 1,708 Sq Ft
- $700/SF
- 16 Days On Market
- 3 Beds
- 2 Baths
- Built 1971
56 Riverview Dr, Chatham, MA 02633

Located in Chatham's sought after Riverbay Estates, known for its treelined streets and community vibe, this residence is nicely sitauated near two scenic ponds for fishing and paddleboarding - and Jackknife Cove Beach is a short drive away. Elevated above the road for privacy, this sundrenched one level home offers open living spaces that blend effortlessly into expansive back yard.The home

Chris Rhinesmith Compass Massachusetts, LLC

56 Riverview Dr, Chatham, MA 02633

/42
Est $3,931,195 Not Listed For Sale
- 7 Beds
- 5 Baths
- 3,203 Sq Ft
38 Sandy Shoes Ln, Chatham, MA 02633

38 Sandy Shoes Ln, Chatham, MA 02633

/24
$5,900,000
- 2 Beds
- 2.5 Baths
- 1,850 Sq Ft
99 Uncle Alberts Drive Extension, Chatham, MA 2633

Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future

Shane Masaschi

Compass

(508) 400-2035

99 Uncle Alberts Drive Extension, Chatham, MA 2633
/41
$2,500,000 Sold Oct 24, 2025
- 3,834 Sq Ft
- $652/SF
- 152 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1987
106 Stage Neck Rd, Chatham, MA 02633

Nestled on just over an acre of meticulously landscaped grounds with a private well for irrigation near the Oyster River, this 4-bedroom, 3.5-bath home offers a rare opportunity to create your dream space. With deeded access to a small, shared boathouse, it provides a serene and sophisticated lifestyle. Built in 1987 and lovingly cared for, the home retains its classic charm and is ready for your

Jen Graham Christie's International Real Estate Atlantic Brokerage

106 Stage Neck Rd, Chatham, MA 02633

/26
Est $1,893,879 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
393 Main St, Chatham, MA 02633

393 Main St, Chatham, MA 02633

/42
$7,900,000
- 7 Beds
- 6.5 Baths
- 6,521 Sq Ft
44 Buena Vista Rd, Chatham, MA 02633

Chatham Waterfront Masterpiece. A private estate on Cape Cod's most coveted coastline in one of New England's most prestigious coastal communities. 44 Buena Vista Road is an extraordinary waterfront estate, a rare offering blending timeless elegance with resort-style amenities. Designed for both grand entertaining and intimate family living, this residence offers sweeping ocean views,

Shane Masaschi

Compass

(508) 501-9618

44 Buena Vista Rd, Chatham, MA 02633
/45
$1,350,000 Sold Oct 23, 2025
- 1,861 Sq Ft
- $725/SF
- 106 Days On Market
- 2 Beds
- 3 Baths
- Built 2015
116 Happy Valley Rd, Chatham, MA 02633

Located off a private way to Ridgevale Beach overlooking a majestic cranberry bog sits this cozy colonial paradise. Built in 2015 by an award winning design/build company is this very private getaway. 1st level open plan features brk bar & dining/living area with views to the bog pond. Door to south facing deck setup for dining & and all day sun. 2 entry kitchen with granite counters & stainless

Ward Brown William Raveis Real Estate & Home Services

116 Happy Valley Rd, Chatham, MA 02633

/26
Est $2,439,748 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,174 Sq Ft
10 Mill Hill Ln, Chatham, MA 02633

10 Mill Hill Ln, Chatham, MA 02633

/2
$619,000
- Land
- 1.01 Acres
- $612,871 per Acre
1761 Main St, Chatham, MA 02633

Nestled in the picturesque town of Chatham, expansive one-acre lot presents a rare opportunity to craft your dream home in a serene setting. Backing up to a tranquil cranberry bog, this unique property offers privacy and natural beauty, providing an idyllic backdrop for your future residence.With ample space and potential, this versatile lot may accommodate two homes, making it perfect for those

Kimberly Clark

Bayside Realty Consultants

(508) 719-6244

1761 Main St, Chatham, MA 02633
/37
$1,500,000 Sold Oct 22, 2025
- 2,340 Sq Ft
- $641/SF
- 134 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1971
307 Riverview Dr, Chatham, MA 02633

Discover luxury and comfort in this stunning Riverbay home nestled with beautiful landscaping on Riverbay Drive. This meticulously renovated 7 room ranch offers 2340 sq. ft of elegant living space, featuring 3 spacious bedrooms, including a sunny primary suite, 2.5 baths with double sink vanities. The inviting foyer introduces you to the warmth of the formal living room with fireplace, open plan

Phyllis Power Compass

307 Riverview Dr, Chatham, MA 02633

/44
Est $3,306,559 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,422 Sq Ft
50 Chase St, Chatham, MA 02633

50 Chase St, Chatham, MA 02633

/74
$2,295,000
- 4 Beds
- 3.5 Baths
- 4,072 Sq Ft
55 Winterset Dr, Chatham, MA 02633

Welcome to your dream retreat at 55 Winterset Drive in Great Hill Estates, one of Chatham's most desirable neighborhoods. This custom built 4 bedroom, 3.5 bath home offers 4000 sq ft of warm & inviting living space on just under 2 acres of park-like grounds with deeded rights to crystal clear Lover's Lake, making it the perfect home for unwinding & entertaining. Two cathedral great rooms, 4 brick

Tara Schiffmann Brown

Bayview Real Estate

(508) 388-5284

55 Winterset Dr, Chatham, MA 02633
/43
$846,000 Sold Oct 21, 2025
- 1,536 Sq Ft
- $551/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 1977
29 Wilfred Rd, Chatham, MA 02633

OPEN HOUSE CANCELLED-Don't miss this 3-bedroom, 2-bath, lovingly cared for home offering 1,536 sq. ft. of inviting living space including a large open great room and living room with fireplace. Beautiful hardwood floors run throughout. Ideally located in a quiet neighborhood, the house is situated on the bike path and a short distance to White Pond for kayaking and swimming . Relax on the

Jack Bohman Gibson Sotheby's International Realty

29 Wilfred Rd, Chatham, MA 02633

/4
Est $3,262,626 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,016 Sq Ft
35 Mill Hill Ln, Chatham, MA 02633

35 Mill Hill Ln, Chatham, MA 02633

/69
$3,850,000 Open Sat 10:30AM - 12PM
- 3 Beds
- 4.5 Baths
- 3,640 Sq Ft
287 Cedar St, Chatham, MA 02633

NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat nestled ''On the Loop'' in Chatham. This elegant residence showcases exceptional craftsmanship & luxurious finishes, making it a true masterpiece of coastal living. The gourmet kitchen w/Quartz countertops is a chef's dream, featuring top-of-the-line Subzero, Miele, and Wolf appliances. The center island

Shane Masaschi

Compass

(508) 952-9486

287 Cedar St, Chatham, MA 02633

Showing Results 1 - 40, Page 1 of 18

Massachusetts Barnstable County Chatham

Home Trends in Chatham, MA

On average, homes in Chatham, MA sell after 77 days on the market compared to the national average of 53 days. The median sale price for homes in Chatham, MA over the last 12 months is $1,500,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,500,000

Median Single Family Sale Price

$1,975,000

Median Townhouse Sale Price

$4,125,000

Median 2 Bedroom Sale Price

$485,000

Median 1 Bedroom Sale Price

$447,000

Average Price Per Sq Ft

$936

Number of Homes for Sale

Last 12 months Home Sales

218

Months of Supply

2.80

Median List Price

$1,872,500

Median Change From 1st List Price

Median Home Sale Price YoY Change

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