The Escapes

Dennis, MA —
The Perfect Cape Cod Village Center

Intricate traces of our nation’s history can be found all over the village of Dennis. Even the street names, Whig St., Pilgrim Road, Nobscusset Road, to name a few, tell a story. Around every bend there seems to be some relic, whether it’s the 300-year-old Josiah Dennis Manse, home of the town’s namesake, or the 300 million year old Hokum Rock named after the Native Americans who lived here.

Featured Listings

18 Wendy Way, Dennis (West Dennis), MA

$4,275,000
Sited at the tip of one of the coveted West Dennis Fingers, this renovated waterfront home offers unobstructed, 180-degree water views that capture the feel of looking out from the deck of your private ship. Designed in an L-shape to ensure quiet, view-filled spaces, the home is a true private sanctuary at the water's edge where you can watch the sunrise, sunset & passing boats against the backdrop of Bass River & Nantucket Sound. Deep-water dockage includes a 72-foot dock on the protected lagoon side, plus a rare license & permit for a second dock on the river side. Extensive updates over the last five years feature new steel framing, a brand-new kitchen, refreshed baths, new wood floors, HVAC, whole-house generator and a custom seawall. The flexible floor plan offers primary suites on both the main & upper levels, plus a dedicated guest wing. Complete with a spacious two-car garage, seaside fire pit, and seamless ocean access, this is an extraordinary opportunity to establish your family's Cape Cod legacy.

1005 Main Street, Dennis, MA

$4,250,000
An iconic estate at 1005 Main St in Dennis Village, this lakefront sanctuary was the vision of Joseph Carr, founder of Josh Cellars Winery, and wife Deirdre. Inspired by classic Nantucket architecture with a Hudson River Valley/NYC flair, the home was designed by Mark Zebrat and built by Gable Bulding, both of Chatham. It offers universally functional interiors tailored just as well for grand galas as for intimate gatherings. The sprawling front lawn has hosted rousing white parties and lawn games, while a winding, wooded path leads to the shores of Scargo Lake, complete with a hidden lakeside living room. Inside, enjoy wide King Pine floors, a custom La Cornue range, Italian Carrara marble, and a secret wine tasting room. Featured across top publications, the property includes a new two-story, two-car garage withan executive office, plus a separate "salon" outbuilding that seats up to 14 for an al fresco dinner party. Built along historic Route 6A where early sea captains intentionally settled, this tranquil retreat offers private and warm freshwater swimming with the famous Dennis bayside beaches just around the corner.

64 Wingfoot Drive, Barnstable (Cummaquid), MA

$1,499,000
Life at 64 Wingfoot Drive starts with a spectacular sunrises over the 17th fairway of Cummaquid Golf Course. This isn't just a place to live; it's a spacious, welcoming base for family holidays, summer weekends, and effortless entertaining. Inside, the home breathes luxury without the pretense. Soaring ceilings throughout the main living areas and kitchen create an airy, expansive feel, anchored by the warmth of both wood-burning and gas fireplaces. When you aren't on the course, the sunroom is the perfect spot for morning coffee, while the primary suite offers a true retreat featuring a deep, standalone soaking tub. Outside, the property transitions into a private backyard club of your own. You can tend to the garden, unwind in the hot tub, or gather generations around the outdoor fire pit for post-golf cocktails under the stars. Complete with generous storage for all your gear, this property perfectly captures that elusive balance of sophisticated country club proximity and relaxed, comfortable Cape Cod living.

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