Chatham, MA Homes

/41
$725,000
- 3 Beds
- 2 Baths
- 1,813 Sq Ft
1996 Main St, Chatham, MA 02633

Welcome to 1996 Main Street in the picturesque town of Chatham, MA! This charming 3-bed, 2-bath ranch style home spans 1,813 square feet & is ready for your vision & creativity. With several essential updates already in place, including a new roof, fresh shingles, & a newer gas heating system, you can focus on adding your personal touch to make this house your dream retreat. The property is

Shane Masaschi

Kinlin Grover Compass

(508) 506-5693

1996 Main St, Chatham, MA 02633
/34
$14,000 per month
- 5 Beds
- 6 Baths
- 4,600 Sq Ft
- House for Rent
351 Whidah Dr, Chatham, MA 02650

**Summer Weekly or Monthly rental, please inquire about availability** Incredible views and exclusive location! Located in North Chatham, with expansive, commanding and sweeping saltwater views of the Atlantic Ocean, Nauset Beach, Strong Island, Bassing Harbor and north to Pleasant Bay and Orleans from this classic Cape Cod home located at end of a quiet road located in Cannon Hill. High on a

Anthony Escobedo Coldwell Banker Realty - Boston

351 Whidah Dr, Chatham, MA 02650
/41
$1,595,000 Pending
- 3 Beds
- 4 Baths
- 2,760 Sq Ft
55 Twine Field Dr, Chatham, MA 02659

2 Acres in Chatham! Invite the outdoors in with this sun-filled home in a serene setting. Large sliding doors from the dining room and owner's suite let you step out onto an expansive deck and patio overlooking a tranquil inground pool, established gardens, and the Twine Field Conservation Land. This backyard oasis is perfect for hosting and relaxing. Continue enjoying Cape Cod nature on the Old

Jen Whitaker Gibson Sotheby's International Realty

55 Twine Field Dr, Chatham, MA 02659

/21
Est $1,347,983 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,393 Sq Ft
32 Wells Hollow Rd, North Chatham, MA 02650

32 Wells Hollow Rd, North Chatham, MA 02650

/40
$1,700,000
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
9 Bettys Path, Chatham, MA 02633

Welcome to 9 Bettys Path, your private hideaway w/panoramic views of nature's finest artwork! This charming 3-bed, 2-bath home is nestled on a 1.8-acre lot, complete with a stunning kettle pond and a lush pastoral backdrop. Renovated in 2014, the home boasts a fresh roof and all the modern comforts. Step inside to find an inviting living room with a cozy fireplace, a dining room that opens onto a

Shane Masaschi

Kinlin Grover Compass

(508) 682-4461

9 Bettys Path, Chatham, MA 02633
/40
$1,117,000 Sold May 01, 2025
- 1,508 Sq Ft
- $741/SF
- 51 Days On Market
- 3 Beds
- 2 Baths
- Built 1996
3 Whiteleys Way, Chatham, MA 02633

Completely renovated home with quality finish work, already on town sewer with the lowest tax rate on the Cape, this Chatham beauty features one level living, a cathedral ceiling in the open concept living area, central air, a garage, and the ability to add a pool. The living area has a gas connection for the fireplace, white oak floors, and plenty of space to make this work for your year round

Tiffany Callahan Greer Real Estate, LLC

3 Whiteleys Way, Chatham, MA 02633

/36
Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,646 Sq Ft
1934 Main St, Chatham, MA 02633

1934 Main St, Chatham, MA 02633

/18
$725,000
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
19 Stoughton Ln, Chatham, MA 2633

Here is your chance to own a slice of seaside Chatham! This prime location is only a short walk or .02 miles to stunning Ridgevale Beach on pristine Nantucket Sound. Included in the sale is a passed 3 bedroom Title V septic inspection report and Board of Health letter, ZBA approval to demolish the existing structure and to build a dwelling with a deck via special permit and Conservation approval.

Shane Masaschi

Kinlin Grover Compass

(508) 400-2035

19 Stoughton Ln, Chatham, MA 2633
/41
$2,350,000 Sold Apr 30, 2025
- 2,254 Sq Ft
- $1043/SF
- 12 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1977
2519 Main St, South Chatham, MA 02659

Salt waterfront oasis ,sited down a long paved drive offers a year round Chatham paradise. Tastefully renovated 3BR 2.5 bath home offers a flexible floor plan with the addition of a second level media room with hickory floors and lower level overflow/office space. The main level boasts fine finishes and dramatic water views throughout the open floor plan. The living room has black walnut

Lori Fanning Smith Compass Massachusetts, LLC

2519 Main St, South Chatham, MA 02659

/50
Est $1,614,510 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,960 Sq Ft
39 Shady Ln, Chatham, MA 02633

39 Shady Ln, Chatham, MA 02633

/6
$265,500
- Land
- 0.72 Acre
- $368,750 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

Kinlin Grover Compass

(508) 691-8324

0 George Ryder Rd Unit 73104629, Chatham, MA 02633
/50
$1,200,000 Sold Apr 30, 2025
- 2,062 Sq Ft
- $582/SF
- 282 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1970
54 Rowland Dr, North Chatham, MA 02650

Discover coastal charm and scenic views of Ryder's Cove from this spacious 4-bedroom, 3.5-bathroom home nestled in North Chatham. Deeded rights to the water, provide direct access for boating and water activities on this saltwater inlet leading to Pleasant Bay.Inside, hardwood floors and a spacious kitchen create a warm and inviting atmosphere. Complemented by spacious living areas, including

Barbara Garside eXp Realty, LLC

54 Rowland Dr, North Chatham, MA 02650

/12
Not Listed For Sale
140 Happy Valley Rd, Chatham, MA 02633

140 Happy Valley Rd, Chatham, MA 02633

/8
$4,395,000
- 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 Viking appliances. The center

Shane Masaschi

Kinlin Grover Compass

(508) 290-5337

287 Cedar St, Chatham, MA 02633
/77
$4,500,000 Sold Apr 23, 2025
- 3,724 Sq Ft
- $1208/SF
- 3 Days On Market
- 3 Beds
- 5 Baths
- Built 2007
79 Barcliff Ave, Chatham, MA 02633

A property of this caliber rarely comes on the market in such a prime location. This custom-crafted residence, built in 2007, has undergone numerous updates and improvements over the years, ensuring it remains fresh and current. Overlooking Black Pond with views of Chatham Harbor and the Atlantic, this expansive home features three levels of living space. The main floor includes an open concept

Doug Grattan Christie's International Real Estate Atlantic Brokerage

79 Barcliff Ave, Chatham, MA 02633

/4
Est $2,912,250 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

/30
$2,549,000
- 4 Beds
- 2 Baths
- 1,238 Sq Ft
213 Main St, Chatham, MA 02633

Location! Location in the heart of Chatham! Historic Greek Revival circa 1850's in the Old Village, with water views of Chatham Harbor, Andrew Harding's landing and Lighthouse beach & Main St shopping/dining, Band Concerts, nearby! This charming 4 bed/2 bath home has a sunny eat-in beamed family room with sliders to deck, cozy kitchen adjacent and a front Living room with gas fireplace, warm

Phyllis Power Kinlin Grover Compass

213 Main St, Chatham, MA 02633
/44
$1,150,000 Sold Apr 18, 2025
- 2,881 Sq Ft
- $399/SF
- 2 Days On Market
- 4 Beds
- 3 Baths
- Built 1969
15 Wood Valley Rd, Chatham, MA 02633

Open House Cancelled-Discover the perfect blend of charm and modern convenience in this beautiful 4-bedroom, 3-bath Cape-style home in Chatham. Located in a serene setting with access to Lovers Lake, this home is in excellent condition and offers everything you need for comfortable year round or seasonal living. The first floor with refinished hardwood floors has an updated kitchen, living room

Jack Bohman Gibson Sotheby's International Realty

15 Wood Valley Rd, Chatham, MA 02633

/51
Est $3,176,577 Not Listed For Sale
- 6 Beds
- 4 Baths
- 4,449 Sq Ft
114 Main St, Chatham, MA 02633

114 Main St, Chatham, MA 02633

/37
$1,695,000
- 3 Beds
- 2.5 Baths
- 2,340 Sq Ft
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

Phyllis Power Kinlin Grover Compass

307 Riverview Dr, Chatham, MA 02633
/41
$840,000 Sold Apr 16, 2025
- 2,212 Sq Ft
- $380/SF
- 66 Days On Market
- 4 Beds
- 2 Baths
- Built 1964
23 Malabar Rd, Chatham, MA 02633

This is a wonderful opportunity in Chatham to purchase a four-bedroom, two-bath home with a beautiful backyard. The 8-room house totals 2,212 sq ft of finished living space, 1,547 sq ft on the first two floors, and an additional 665 sq ft of finished basement. Highlights include an open living room/kitchen floor plan, two bedrooms and a full bath on the first floor, and two large bedrooms and a

23 Malabar Rd, Chatham, MA 02633

/8
Est $4,561,566 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,446 Sq Ft
58 Whistler Ln, North Chatham, MA 02650

58 Whistler Ln, North Chatham, MA 02650

/42
$2,500,000 Open Sat 10AM - 12PM
- 4 Beds
- 3.5 Baths
- 3,865 Sq Ft
25 Menekish Ln, Chatham, MA 02633

Tucked away on a private lane in North Chatham, 25 Menekish Lane offers a rare blend of privacy and proximity—just steps from Cow Yard Beach, Chatham Bars Inn, the Fish Pier, and Main Street. Built in 2006, the nearly 4,000 sq ft home blends timeless Cape charm with modern ease: soaring ceilings, abundant natural light, and a flowing floor plan ideal for entertaining. A chef’s kitchen with island

25 Menekish Ln, Chatham, MA 02633
/48
$820,000 Sold Apr 14, 2025
- 1,975 Sq Ft
- $415/SF
- 11 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1999
84 Middle Rd, South Chatham, MA 02659

Lovely Chatham Cape style home enjoyed by one happy family & now ready for a new chapter. First floor main bedroom with attached bath and laundry, large family room with gas stove, southern sunny exposure, slider to deck and patio. Traditional living room with cathedral ceiling and fireplace, open dining & kitchen with SS appliances, granite counters new in 2018, 2 grand bedrooms and bath

Michael Hall William Raveis Real Estate & Home Services

84 Middle Rd, South Chatham, MA 02659

/32
Est $3,174,428 Not Listed For Sale
- 6 Beds
- 4 Baths
- 2,527 Sq Ft
119 Scatteree Rd, North Chatham, MA 02650

119 Scatteree Rd, North Chatham, MA 02650

/58
$1,750,000
- 4 Beds
- 3 Baths
- 1,990 Sq Ft
235 Training Field Rd, Chatham, MA 02633

Tucked away from the road in desirable Riverbay, this charming ranch offers comfortable living with three bedrooms and two full baths. A standout feature is the spacious one-bedroom ancillary apartment with its own private entrance, a cozy kitchenette, and a fully accessible handicapped bathroom--perfect for guests, extended family, or rental income.The home features a fireplaced living room, a

Keith Bradley Gibson Sotheby's International Realty

235 Training Field Rd, Chatham, MA 02633
/56
$1,675,000 Sold Apr 01, 2025
- 1,600 Sq Ft
- $1047/SF
- 26 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1959
51 Bucks Creek Rd, Chatham, MA 02633

Experience coastal refinement in this meticulously renovated 3-bedroom ranch, created by an interior designer and custom craftsman. Designed as a forever home, this residence combines timeless design with superior craftsmanship.The gourmet kitchen features custom cabinetry and chef-grade appliances, exemplifying a thoughtful approach to both form and function. Every detail has been upgraded, from

Dawn Lee Gibson Sotheby's International Realty

51 Bucks Creek Rd, Chatham, MA 02633

/38
Est $2,209,313 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,008 Sq Ft
671 Old Harbor Rd, North Chatham, MA 02650

671 Old Harbor Rd, North Chatham, MA 02650

/33
$2,750,000
- 4 Beds
- 3.5 Baths
- 3,834 Sq Ft
106 Stage Neck Rd, Chatham, MA 02633

Nestled on just over an acre of meticulously landscaped grounds 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 shared boathouse, it provides a serene and sophisticated lifestyle. Built in 1987 and well cared for by its original owner, the home retains its classic charm and is ready for your updates. Designed for

Jen Graham Christie's International Real Estate Atlantic Brokerage

106 Stage Neck Rd, Chatham, MA 02633
/5
$1,900,000 Sold Mar 20, 2025
- 1,724 Sq Ft
- $1102/SF
- 2 Days On Market
- 5 Beds
- 3 Baths
- Built 1900
172 Barcliff Ave, Chatham, MA 02633

Attention buyers, builders, contractors! Rare opportunity to complete the renovation of this 5-bed, 3-bath home situated on a sprawling 27,355 sq. ft. lot in a highly desirable location. Imagine designing your dream home; this property offers the perfect canvas to bring your vision to life. The majority of the interior has been demoed down to the studs, but the framework is already in place,

Louise Coakley Better Homes and Gardens Real Estate - The Shanahan Group

172 Barcliff Ave, Chatham, MA 02633

/56
Est $6,990,145 Not Listed For Sale
- 4 Beds
- 5.5 Baths
- 5,528 Sq Ft
444 Old Harbor Rd, Chatham, MA 02633

444 Old Harbor Rd, Chatham, MA 02633

/65
$3,495,000
- 4 Beds
- 3.5 Baths
- 4,857 Sq Ft
36 Moonbeam Ln, Chatham, MA 02633

This expansive Cape with timeless curb appeal is located in an exclusive Chatham neighborhood, and includes deeded rights to the Oyster Pond River. Immaculate and lightly used, you'll find 4,857 square feet of comfortable, casual elegance in a thoughtfully-designed floor plan. There are 4 spacious bedrooms including a lovely first-floor primary En-suite. Bright granite & stainless kitchen opens

Lori Jurkowski Christie's International Real Estate Atlantic Brokerage

36 Moonbeam Ln, Chatham, MA 02633
/16
$485,000 Sold Mar 18, 2025
- 1,013 Sq Ft
- $479/SF
- 134 Days On Market
- 2 Beds
- 2 Baths
- Built 1987
407 Orleans Rd Unit B, Chatham, MA 2633

RENOVATED IN 2023..LIke new 2 bedroom, 2 bath condominium of over 1013 square feet.... New windows, new flooring, new kitchen cabinets, granite counter tops and stainless steel appliances,. Bathrooms have custom tile and new vanities and all new fixtures. Small private deck and inside parking in a carport.......Located close to everything Chatham has to offer: Town, shopping, restaurants, and

John Burke William Raveis Chatham

407 Orleans Rd Unit B, Chatham, MA 2633

/12
Est $5,793,929 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

/42
$3,250,000
- 4 Beds
- 4.5 Baths
- 3,603 Sq Ft
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
/22
$435,000 Sold Mar 14, 2025
- 1,013 Sq Ft
- $429/SF
- 6 Days On Market
- 2 Beds
- 1 Bath
- Built 1987
409 Orleans Rd Unit B, North Chatham, MA 02650

Welcome to Quail Run, nestled off-the-beaten-path in beautiful North Chatham-yet convenient, easy access to all! This immaculate, delightful unit opens into a spacious, warm and welcoming living room with vaulted ceiling, hardwood floors, and new picture window overlooking a peaceful wooded area; the dining room has built-ins and the same wooded views; the efficient kitchen offers good storage,

Debra Bassett Cape Cod Associates R E

409 Orleans Rd Unit B, North Chatham, MA 02650

/36
Est $2,074,955 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,999 Sq Ft
32 Gladen Ln, Chatham, MA 02633

32 Gladen Ln, Chatham, MA 02633

/61
$2,100,000
- 3 Beds
- 2 Baths
- 2,366 Sq Ft
10 Pursel Dr, North Chatham, MA 02650

Perched on a bluff in one of Chatham's most coveted locations, Summer Wind is an expanded Cape Cod classic offering the perfect blend of traditional charm and modern amenities. With deeded access to picturesque Ryder's Cove, the luxury of an association beach, and the convenience of deep-water access to Pleasant Bay and the Atlantic beyond. As you approach the property, a circular drive and

Doug Grattan Christie's International Real Estate Atlantic Brokerage

10 Pursel Dr, North Chatham, MA 02650
/36
$2,000,000 Sold Mar 14, 2025
- 2,884 Sq Ft
- $693/SF
- 133 Days On Market
- 3 Beds
- 4 Baths
- Built 2002
53 Ocean Port Ln, Chatham, MA 02633

South of 28 and situated on a quiet sandy lane in West Chatham, this home is the perfect beach house just a short distance to both Barn Hill Landing and Hardings Beach. Recently renovated, the home exudes coastal style living and offers superbly designed indoor and outdoor spaces. The house welcomes with an open concept great room with cathedral ceilings, abundant light and a fireplace with

Chris Rhinesmith Compass

53 Ocean Port Ln, Chatham, MA 02633

/26
Est $1,859,786 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
393 Main St, Chatham, MA 02633

393 Main St, Chatham, MA 02633

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