Chatham, MA Homes for Sale with Acreage

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

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

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

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

** 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 & Assoc.

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

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

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