242 Sheep Pond Dr
Brewster, MA 02631

''The Best View of Sheep Pond.'' That's what the neighbors say-and once you see it, you'll understand why. Tucked down a long, private driveway sits this five-bedroom, two-bath classic, owned by one family for 58 years. The home blends warmth, natural light, and timeless character with a layout designed for generations to enjoy. A cathedral-ceilinged living room, the dining area, and the kitchen all look out toward the pond. Downstairs, a sprawling walk-out basement offers incredible flexibility, complete with a second fireplace, a spacious den, and a fully functional second kitchen. The outdoor living space is just as compelling. You've got your own little piece of Sheep Pond with a private beach. The expansive Azek deck and enormous patio are perfect for hosting sunset dinners on the pond, or quiet mornings with coffee and a Brewster Bun. You'll also find a large outdoor shower, mature plantings, a 200-amp electrical panel, a generator, and a charming garden shed. With its irreplaceable setting, private beach access, and rich family history, this is a rare opportunity to own a legacy property on Sheep Pond in Brewster. Buyers & agents should confirm all information. Welcome to your personal piece of Brewster history, perched above the iconic Sheep Pond, named for the flocks of early settlers who once led their sheep here to drink. Centuries later, a man with his own kind of vision carved out a private 9-hole golf course in the area. When that dream faded, and the land became available, the current owner saw what few others did: a place with promise. He claimed his lot and, over nearly six decades, cultivated a haven defined by warmth, light, love, and memories. Today, you have a rare chance to inherit not just a home, but the spirit of this very special place. From the moment you arrive, the approach sets the tone. Flanked by towering evergreens and mature plantings, the long private driveway points you towards home and the pond. At the end of it, a sunny yellow home greets you, warm, welcoming, and brimming with character. Step inside and discover five bedrooms, two full bathrooms, an unexpectedly modern layout that prioritizes light, openness, and flow, and a huge walkout basement and patio. Speaking of the basement, there's an extra kitchen that dazzles you with, you guessed it, yellow! While the home invites updating, its fundamentals are all in place, and they are strong. You'll find a generator for those intense Cape storms, an upgraded 200 AMP electrical service, two heat pumps and central air in the primary suite. With its irreplaceable setting, private beach access, and rich family history, this is more than just a home; it's a story, a sanctuary, and a rare opportunity to own a legacy property on Sheep Pond in Brewster. This home is charming, strong, and unique. Update: Sunday, September 28. Open house is cancelled. If you still want to see the house, contact me.