Chatham, MA Homes for Sale with Pool

In one of Chatham's most storied and visually captivating settings, adjacent to the iconic Mitchell River wooden drawbridge, this extraordinary waterfront estate--masterfully crafted by the renowned Eastward Companies--represents a rare convergence of architectural distinction, coastal heritage, and modern luxury. Spanning more than 6,200 square feet across three impeccably designed levels, the

The Grattan Group Christie's International Real Estate Atlantic Brokerage

This 5-bedroom, 5.5-bath, 5,620-square-foot home on 40,000 + square foot lot sits along Chatham's popular walking loop, just steps from Stage Harbor, public town landing and the Yacht Club. Ideal for entertaining or relaxing, it features a large deck, swimming pool and hot tub. Inside, hardwood floors and tall ceilings create a bright, open feel. The kitchen offers granite countertops, generous

Tim Bailey John C. Ricotta & Associates, Inc.

Brand-new and sun-filled, this exceptional shingle-style Gambrel is privately set on nearly an acre of professionally landscaped, level grounds just off coveted Shore Road, less than a block from the ocean. A refined coastal retreat, the 4-bedroom, 4.5-bath residence pairs exceptional craftsmanship with effortless luxury and gracious indoor-outdoor living. Beautiful millwork and 9' ceilings

Jill Boudreau eXp Realty LLC - Corporate Office

Spectacular custom-built Chatham home designed for effortless entertaining, offering three bedrooms, two bonus rooms, inviting living spaces on all three levels, and a picture-perfect backyard pool setting. A charming front porch welcomes you into a light-filled interior rich with coastal character. The main living room features custom built-ins, shiplap detail, and a wood-burning fireplace,

Chris Rhinesmith Compass Massachusetts, LLC

Shore Road is more than an address. It's a feeling. The moment you turn onto it, the mood quietly shifts. Clipped hedges, impossibly pretty gardens, sparkling water views, and the grand Chatham Bars Inn create a storybook setting. Offered for the first time in almost four decades, ''Offshore'' encompasses more than an acre on Shore Road - an exceptional combination of land, privacy, and

Sarah Keith eXp Realty, LLC

A distinguished new residence by Eastward Companies, this exceptional home seamlessly blends timeless architecture with modern luxury, all within walking distance to Chatham Village, Oyster Pond, and renowned dining. Thoughtfully designed and impeccably crafted, the home spans over 5,800 square feet across three finished levels. The main level offers an elegant yet inviting floor plan, featuring

The Grattan Group Christie's International Real Estate Atlantic Brokerage

Set within a private gated enclave in South Chatham’s emerging luxury corridor, 48 Sylvan Way is a singular estate moments from the Cape’s most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational, the property offers rare privacy and scale in one of Chatham’s most compelling settings. Spanning 5,700 square feet across twelve rooms, this

Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

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 6,000 square feet of living space sited on 1.635 bucolic acres -- a sanctuary setting with the scale and usability to

Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

The ultimate Chatham compound! Set high on a bluff with views of Hardings Beach and Nantucket Sound, this impressive property features a 4,100+ sqft main house, oversized two-car garage with private guest suite above, and a resort-style backyard with an expansive patio and pool. Inside, ten-foot ceilings, custom built-ins, abundant natural light, and generous living spaces set the tone. The grand

Chris Rhinesmith Compass Massachusetts, LLC

This exceptional 1.84 acre property offers a unique combination of space, privacy, versatility, and quintessential Cape Cod living. Surrounded by beautifully landscaped grounds and abutting conservation land, the property is a secluded retreat complete with a renovated main residence, in-ground swimming pool, detached two-car garage with a one-bedroom apartment above, and deeded access to Lovers

The Grattan Group Christie's International Real Estate Atlantic Brokerage

Wonderful ranch house on 7/10's of an acre lot in Ryder's Cove Landing in North Chatham. All living on one floor just a quick walk away from the large inground pool, tennis court, beach, and a DOCK that all compliment this area and are reserved for the homeowners in the association. Partially finished lower level serves as a bonus room and second living area. Town field card has 3 bedrooms and

John Burke William Raveis Chatham

New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. Fox Hill sits on 2.74 acres in Chatham, a renovated coastal estate with sweeping views of Crows Pond, Eastward Ho and Pleasant Bay from nearly every angle. The shingle-style exterior is substantial and classic Cape Cod, with a two-car garage and a private boat dock giving direct access to the

Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

This exceptional 1.84 acre property offers a unique combination of space, privacy, versatility, and quintessential Cape Cod living. Surrounded by beautifully landscaped grounds and abutting conservation land, the property is a secluded retreat complete with a renovated main residence, in-ground swimming pool, detached two-car garage with a one-bedroom apartment above, and deeded access to Lovers

Andrew Grattan Christie's International Real Estate Atlantic Brokerage