This is the South Chatham beach house everyone is looking for! Fully renovated and turnkey, 124 Pleasant Street is ready for immediate enjoyment -- as a private retreat of your own, or as a proven, guest-favorite rental. A short walk to Pleasant Street Beach, this South Chatham location grows only more desirable year over year. The living room, anchored by a fireplace, flows into the dining room and a well-finished kitchen with updated appliances, with first-floor laundry for convenience. Four well-appointed bedrooms offer easy privacy for family, friends, or guests, including an enchanting staircase leading to a second-floor hideaway all its own. A vaulted, screened sunroom connects indoors to out, and a side porch sets the stage for al fresco dining. Outside, the opportunity multiplies: an expansive backyard with ample room for a pool, and two existing structures -- main house plus a detached two-car garage -- laying the groundwork for a true compound-style setup, whether that means a future guest suite, studio, or pool house. This is a rare chance to secure a compound-style property with ideal proximity to the beach and town!
Just 0.4 miles from the sandy shores of Pleasant Street Beach, this enchanting South Chatham Cape-style cottage captures the timeless charm of Cape Cod living. Set down a private lane on a tree-lined lot, this storybook home is filled with warmth and character. The sun-filled interior features an open living and dining area heated by a cozy natural gas stove, a cheerful kitchen with a butcher block island, two inviting bedrooms, one full bath, and an easy single-level floor plan. Step outside to discover your own secluded oasis, where a brick patio, outdoor shower, fire pit tucked beneath the trees, colorful hydrangeas, and raised garden beds create the perfect setting for relaxing and entertaining after a day at the beach. Whether you're searching for a charming year-round residence or a treasured Cape Cod retreat, this special home offers the perfect setting to enjoy everything that defines life in Chatham, from beach days and strolls along Main Street to boutique shopping, waterfront dining, and beloved summer band concerts. Offered fully furnished.
Unique post-and-beam masterpiece, blending rustic character with modern comfort. This dramatic home showcases soaring cathedral ceilings, exposed timber framing, and an open lofted design with stained glass windows, creating an impressive sense of space and light. Rich wood details and crisp white walls create a timeless balance of warmth, craftsmanship, and coastal elegance. Thoughtfully designed for gathering, relaxing, and entertaining, this one-of-a-kind property offers the charm of a custom retreat with the functionality of today's living. Ideally located close to beaches, shopping and restaurants. With deeded rights to the private beach just steps away, a beautiful landing to launch your kayaks. This is a truly distinctive home with architectural character, inviting spaces, and an unforgettable sense of place. (Moorings should be available on Taylor's Pond with a relatively short waitlist, check with the Harbormaster!)
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 locations. Spanning 5,700 square feet across twelve rooms, this bespoke new construction residence showcases custom craftsmanship and intentional design throughout, conceived for refined, generational living. Three distinct bedroom wings-including two separate upper-level guest wings-provide exceptional comfort and separation, with each bedroom generously proportioned and ensuite. At its heart, a breathtaking great room anchored by a custom-designed kitchen rises to 23-foot ceilings adorned with shiplap ceilings, reclaimed beams and a fireplace, while an 18-foot wall of glass opens seamlessly to the heated saltwater pool and patio for effortless indoor-outdoor living. A rare offering defined by craftsmanship, presence, and intention-modern Cape Cod estate living at its most elevated.

South Chatham is located in Massachusetts. South Chatham, Massachusetts has a population of 1,030. South Chatham is more family-centric than the surrounding county with 31.87% of the households containing married families with children. The county average for households married with children is 19.97%.
The median household income in South Chatham, Massachusetts is $61,302. The median household income for the surrounding county is $82,619 compared to the national median of $69,021. The median age of people living in South Chatham is 52.8 years.
The average high temperature in July is 77.7 degrees, with an average low temperature in January of 23.4 degrees. The average rainfall is approximately 47.6 inches per year, with 23.1 inches of snow per year.