Waterfront Homes for Sale in Chatham, MA

** Pinkwink, Circa 1850** - A beautifully updated antique in Chatham on 1.48 acres. Five bedrooms—four in the main house, one in the two-room guest suite above the detached two-car garage with private deck and screened in porch below. The main house features a large sunlit chef's kitchen with cathedral ceiling and top-tier appliances, wood floors, spacious dining room with fireplace, living room

Tim Bailey John C. Ricotta & Associates, Inc.

Ideally situated just moments from Chatham's Village boutiques and restaurants, this exceptional three bedroom,two bath residence captures the essence of Chatham coastal living. Privately set on a private dead-end street, the property offers tranquility and also convenience in one of Chatham's most desirable settings. Thoughtfully designed for effortless single-level living, the main floor

Chris Rhinesmith Compass

Nestled in Chatham's exclusive Morris Island neighborhood, this home embodies the Cape Cod lifestyle. Situated in the sought-after Quitnesset community, this property is perfect for making lasting memories. Step into a the foyer with a stunning double curved staircase, leading to a vaulted living room with a cozy fireplace and a chef's kitchen designed for entertaining. Enjoy casual meals in the

Sandra Tanco Kinlin Grover Compass

66 Ethelma Drive is a rare pond front opportunity in Chatham, MA, set along the shores of Emery Pond just minutes from downtown Chatham, Cape Cod beaches, restaurants, shops and close to the bike path. This 4-bedroom, 1-bath home offers 1,547 sq ft on approximately half an acre and presents exceptional potential for renovation, reconstruction, or a custom waterfront build. For buyers seeking

Shane Masaschi Compass

Gracefully sited on edge of Frost Fish Creek, a conservation estuary, this custom built 3 bed,2.5 bath Cape is the essence of Cape Cod style & includes extra 20,737 Sq ft building lot. Sunlit wide pine floors & fine bespoke built-ins, accentuate timeless craftsmanship. Formal living room has grand wood-burning FP, open to elegant dining room & brick floored vaulted ceiling sun/great room with gas

Phyllis Power Compass

NEW CONSTRUCTION: Welcome to 287 Cedar Street, an exquisite 3 BR, 4.5 Bath, 3,640 sf retreat ''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 w/walnut

Shane Masaschi Compass

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

Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha's Vineyard Interior Designs. Walls of glass frame sweeping vistas and invite natural light to pour in throughout the home. Indoor and outdoor spaces flow effortlessly, from sun-drenched rooms to generous

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

Located in Chatham's Countryside neighborhood, this three-bedroom, two-bath cape-style ranch gets plenty of natural light and features a primary suite with a private bath and good closet space. Two additional bedrooms can be used for family, guests, or a home office. The living room has a brick fireplace. A one-car garage and large unfinished basement sits below the home, and the property sits on

Tim Bailey John C. Ricotta & Associates, Inc.

Nestled above the shimmering waters of Bassing Harbor, this extraordinary waterfront retreat was conceived through a multi-year collaboration with Salt Architecture, LaBarge Homes, and Martha’s Vineyard Interior Designs. Walls of glass frame sweeping views and fill the home with natural light, while indoor and outdoor spaces flow seamlessly to expansive decks, terraces, and a resort-style pool

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

Set on nearly an acre with commanding views of Stage Harbor, this Stage Island residence combines timeless elegance with modern comfort. The foyer opens to a dramatic living room framed by expansive windows and a stylish kitchen with an island and dining area that extends to a generous deck—perfect for entertaining. The main level also offers a private ensuite bedroom, den, and laundry. Upstairs

Chris Rhinesmith Compass

Co-ownership opportunity. Fox Hill, a spectacular waterfront retreat sited proudly on nearly 3 acres in a coveted North Chatham location! Within steps to a private beach and dock, this custom shingle residence was designed to accommodate large summer gatherings or cozy weekend getaways! Stunning views of Crows Pond, Eastward Ho and Pleasant Bay can be enjoyed throughout the property, while a

Brian Dougherty Corcoran Property Advisors

Tucked within a coveted North Chatham setting of Harbor Coves and offering access to a private association beach, this exceptional Gambrel-style residence currently under construction with Harbor Builders presents a sophisticated coastal retreat.The property offers generous indoor and outdoor living spaces on a half an acre. The main level features an inviting open floor plan where a

Chris Rhinesmith Compass

Professional photos coming soon! Discover the perfect coastal retreat on Bucks Creek, where sweeping water views and breathtaking sunsets set the backdrop for everyday living. This beautifully maintained home offers 3 bedrooms, 3 baths, and a dedicated office, providing flexible space for both relaxation and productivity. Located just moments from Hardings Beach, the property enjoys a coveted

Judith Smith John C Ricotta & Assoc.

Perfectly positioned on a corner lot in a quiet neighborhood, this beautifully maintained home offers peaceful living just moments from everything Chatham has to offer. Less than a mile from downtown, it provides easy access to shops, restaurants, beaches, and landmarks including the Fish Pier, Veterans Field, Seaside Links, and Chatham Bars Inn. The home offers two levels of living with updates

Tom Riley Compass

Zoned Gb3, this great commercial, multi-use property consists of 2 buildings. The first building built in1995 has 948 sf with a multi-use space, an office and full bath. There is a Viessman heating and hot water system and the full basement is waiting to be finished. The second building has1,638 sf built in 2003 with 2 bays and a carport. One bay has a gas heater and the second floor is ready to

Judith Smith John C. Ricotta & Associates, Inc.

Stunning brand new construction from The Young Companies at 230 Barcliff Ave is well underway and ready for Summer 2026. Architecturally pleasing 4BR 5.5 bath shingled home will offer impeccable details ,finish work, detached two car garage and unbeatable walk to town location. Enjoy walking to Chatham's summer league baseball games, iconic fish pier and exclusive Chatham Bars Inn. The 5300 sf

Lori Fanning Smith Compass

Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfront setting. The property offers four bedrooms and 3.5 baths, each room oriented to the scenery beyond. The residence pairs a classic seaside character with an elevated aesthetic. The main living level is bright and welcoming with a high-end kitchen, generous living room and dining area overlooking the water

Chris Rhinesmith Compass Massachusetts, LLC

Tucked into a sought-after neighborhood just moments from town, shopping, dining, beaches, Veteran's Field, and the bike path, this three-bedroom, two-bath home offers an exceptional opportunity in a prime Chatham location. Built in 1994, the 1,802 square foot property includes a one-car garage and full basement, providing a strong foundation for your vision. Additional features include wood

Shane Masaschi Compass

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

This private oasis in North Chatham , hidden by a long and winding lane, takes you into the past. A spectacular historic setting including natural vegetation rests on one of the last large water front parcels in Chatham. Surrounded by over 1.5 acres, with opportunities for a family compound on a fabulous bluff overlooking, and ownership of, prime beach front on Chatham Harbor, Pleasant Bay, and

John Burke William Raveis Real Estate & Home Services

This two-bedroom, three bath condominium, part of the historic Christopher Ryder House, blends timeless architecture with elegant design. The residence features high ceilings, wood floors, large windows, and generously scaled rooms. The foyer opens to a grand living room with gas fireplace flowing into the dining area and adjoining pantry, with views into the chef’s kitchen featuring a Thermador

Chris Rhinesmith Compass

Professional photos coming soon!Just moments from Hardings Beach, this inviting three-bedroom, two-bath home offers the perfect coastal getaway. Enjoy the benefits of a sought-after association featuring a dock, kayak storage, and a lovely picnic area overlooking the water. Take in beautiful water views and unforgettable sunsets, with private stairs leading down to the water's edge of Bucks Creek

Judith Smith John C Ricotta & Assoc.

Set within the prestigious Harbor Coves enclave of Oyster Harbors, overlooking Ryders Cove, this spectacular North Chatham waterfront residence offers refined coastal living. A dramatic entry opens to a showstopping living room with cathedral ceilings and walls of glass framing panoramic water views. Light-filled interiors flow seamlessly for entertaining and everyday living. The kitchen features

Chris Rhinesmith Compass

NEW CONSTRUCTION - NORTH CHATHAM, 02650. Zillow’s February 2026 data showed just 6 homes for sale in the coveted 02650 North Chatham market, with 50% higher average home values at $1,933,566, compared to 29 homes for sale and a 50% lower average home value of $1,282,193 in 02633. As someone who lives and works in Chatham, I can tell you this kind of difference matters. Buyers at the luxury level

Shane Masaschi Compass

Elevated on a .57 acre lot in a serene North Chatham setting within Ryder's Cove Landing Association, this privately situated 3 bedroom, 3.5 bath home offers three levels of living. The main level features an inviting eat-in kitchen with island, a welcoming living room with fireplace, and a three-season sunroom with TV overlooking peaceful surroundings. The primary suite includes a private bath

Chris Rhinesmith Compass