Chatham, MA Homes for Sale with Pool

LIGHTHOUSE BEACH - A Nantucket-inspired coastal home designed and built by Polhemus Savery DaSilva, this residence beautifully blends elegance and comfort. The open floor plan showcases oversized windows and soaring ceilings, allowing natural light to pour in and illuminating the stunning views of the swimming pool, spa, outdoor kitchen, patio, gas fire-pit, outdoor shower, and irrigated

Jack Bohman Gibson Sotheby's International Realty

At the crossroads of coastal elegance and comfort, a rare union of high value features has emerged in a home priced under $975 PSF. Virtually unrivaled at this price point, a 5700+/- SF home consisting of twelve (12) rooms, (6) bedrooms, five (5) baths, two (2) half baths, impressively situated on 1.63+/- acres of private estate like grounds. Mature old world trees were left intact on a parcel

Chris Olson eXp Realty, LLC

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 & Assoc.

Experience luxury, privacy, and convenience in this exceptional new construction by Minglewood Homes, just moments from downtown Chatham. Situated on a 1.34-acre waterfront lot along the Oyster River, this exquisitely designed home features an open-concept layout, high-end finishes, and impeccable craftsmanship. Designed for both comfort and entertaining, it offers five spacious bedrooms, each

Mina O'Keefe Gibson Sotheby's International Realty

Sears Point Development presents another breathtaking home that could be your new year-round residence or the perfect summer escape for 2026. With panoramic water views of the Oyster Pond and Oyster River and deeded access to the Oyster Pond with mooring potential, this stunning Nantucket-style home boasts 4,989 sf of thoughtfully designed living space, featuring 4 BR and 4/2 Baths on town sewer.

Jack Bohman Gibson Sotheby's International Realty

Welcome to a quintessential Cape-Cod lifestyle, this updated home is steps away to one of the prettiest private lakes in Chatham. With deeded rights to Lovers Lake for kayaking, canoeing, swimming & fishing and set back on a gracious lot this 3BR plus home offers privacy and nature at every turn. First floor has granite/stainless kitchen w/ breakfast bar and dining area w/ fireplace, a great room

Janet Stuart Coldwell Banker Realty - Concord

Chatham: where hydrangeas meet the sea and harbors merge into the ocean. A place where cherished memories are created and passed on through generations. If you've been dreaming of living in this storybook town, just a short stroll from sandy beaches and its vibrant Village, you've arrived. Welcome to 150 Barcliff Avenue. Tucked along one of Chatham's most picturesque streets, this updated home

Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and

John DePreaux Corcoran Property Advisors

Experience unparalleled craftsmanship in this remarkably designed contemporary home with commanding views of Pleasant Bay, Bassing Harbor, and Ryder's Cove. This oceanfront property features one of the most picturesque locations offered on the Cape with peaceful evening sunsets to lively 4th of July fireworks over Pleasant Bay. Take the stairs to the water and enjoy your own private beach and

Doug Grattan Christie's International Real Estate Atlantic Brokerage