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$6,500,000
10 Beds ⋅ 10 Baths ⋅ 73535185 MLS
Landmark Chatham Georgian estate set on 1.3 acres overlooking Oyster Pond, with downtown and beach just moments away. Known as ''Beechwood'', this iconic residence was built in 1948 for Henry Howes, a descendant of one of Chatham's earliest families and showcases exceptional craftsmanship throughout. The stately brick main structure is flanked by two projecting wings. The home offers over 7,500 sq ft with 10 bedrooms and 10 bathrooms. Inside, enjoy hand-painted murals, sweeping water views, curved staircases, intricate woodwork, and beautifully scaled living spaces filled with character. The lower level features a ''speakeasy'', ballroom, workshop, and storage. Outside, expansive terraces, mature gardens, bluestone walkways, towering trees, and rolling lawns create a spectacular setting leading toward the water. The property was divided into three townhouse residences, but has since been used as a single-family home. A rare chance to own one of Chatham's most iconic legacy properties.

150-154 Cross Street, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$5,900,000
6 Beds ⋅ 8 Baths ⋅ 73533378 MLS
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 6000 square feet of living space sited on 1.635 bucolic acres. A first-floor primary wing. Three-car garage. Every bedroom ensuite. An open-concept great room with soaring ceilings anchors the floor-plan, while a fully finished basement provides a complete auxiliary level for guests and entertaining — a depth of program rarely found. Outside, a pool and integrated jacuzzi anchor the aquatic experience, framed by a dramatic firewall feature and wraparound deck purpose-built for outdoor living at scale. Constructed by R.A. Martin — among the most trusted names in Chatham construction — the property offers a rare opportunity to customize finishes to suit. A singular proposition in the Chatham marketplace!

50 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$14,000
6 Beds ⋅ 5 Baths ⋅ 73493755 MLS
**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 bluff, it is the quintessential waterfront location in Chatham. This home's elegant and comfortable furnishings help it stand out from others with a more casual feel. Beautiful water views from every room in the house. Walk down the property stairs to 330 feet of your private beach or walk to the nearby private association beach for a day full of fun. Book this home for a truly memorable vacation.

351 Whidah Rd, Chatham

Listing courtesy of Listing Agent: Anthony Escobedo from Listing Office: Coldwell Banker Realty - Newton.
$4,500,000
6 Beds ⋅ 7 Baths ⋅ 73479712 MLS
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 bespoke new construction residence showcases custom craftsmanship and intentional design, conceived for refined, generational living. Three distinct bedroom wings provide comfort and separation, with each bedroom generously sized and ensuite. At its heart, a breathtaking great room anchored by a custom-designed kitchen rises to 23-foot shiplap ceilings with reclaimed beams and a fireplace, while an 18-foot wall of glass opens to the heated saltwater pool and patio for seamless indoor-outdoor living. A rare offering defined by craftsmanship and presence —modern Cape Cod estate living elevated.

48 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

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