luxury waterfront houses for sale Manchester-by-the-Sea, United States

Majestically sited atop a beautifully landscaped bluff overlooking Buzzards Bay, Stony Beach, and Penzance Point, this iconic Woods Hole residence is a rare expression of timeless coastal living. Beloved by the same family for more than 40 years, the home retains an unmistakable sense of authenticity, with hardwood floors throughout, rich wood paneling, and gracious rooms that reflect generations of summers by the sea. The main level offers a kitchen, den, dining room, living room, and a series of inviting porches and outdoor spaces, each designed to capture the extraordinary setting and sweeping water views. A charming waterfront cabana creates a private perch above the bay, while a separate walkway and deck wrap along the seawall, offering yet another remarkable vantage point from which to experience the coastline. Upstairs, five bedrooms and multiple baths provide generous accommodations for family and guests. Surrounded by established landscaping and set high above the water, this extraordinary property embodies the enduring character, beauty, and understated elegance that have long defined Woods Hole.

Set on more than 2.5 acres with over 300 feet of private waterfront with western views, 156 High Winds Drive captures westerly views across Broad Cove toward Casco Bay. Located within the prestigious High Winds neighborhood, with walking trails and shared access to a dock and float, this exceptional setting offers the quintessential coastal Maine lifestyleboating, fishing, swimming, and spectacular sunsets. Custom built in 2019, the residence was thoughtfully designed to embrace its waterfront setting, with water views from nearly every room. Handcrafted millwork and 5-inch quarter-sawn oak floors showcase the quality throughout. The beautifully appointed kitchen features Thermador appliances, a generous island, and walk-in pantry, opening to a spacious family room with gas fireplace and a light-filled dining area overlooking the lawn and waterfront. Four ensuite bedrooms offer exceptional flexibility. A first-floor suite with fireplace can serve as a primary bedroom, private guest quarters, or home office. Upstairs, three additional suites include a second primary option. Both primary suites feature fireplaces, walk-in closets, and beautifully appointed baths with radiant heat. A finished daylight lower level adds flexible space for media, recreation, fitness, or entertaining. Custom landscaping and hardscaping lead toward the waterfront, while a detached barn with private guest suite above provides additional space for visitors, extended family, or a studio. On-demand generators serve both buildings. Remarkably private yet just 10 minutes from Yarmouth Village and convenient to Portland, 156 High Winds Drive combines substantial private waterfront, coveted western exposure, and exceptional craftsmanship in an extraordinary coastal Maine setting.

Waterfront Living on the North Fork- Wake up to breathtaking views of the Peconic Bay, where sunlight dances across the water, birds soar above the neighboring nature preserve, and a tranquil deep-water inlet stretches beyond your deck. This charming beach cottage offers a rare opportunity to experience the very best of North Fork waterfront living. Featuring 3 bedrooms and 2 baths, the home offers a comfortable, open-concept layout connecting the waterside living room, dining room, kitchen, and entertainment areas—perfect for relaxed summer mornings, afternoon gatherings, and memorable evenings with family and friends. Step outside onto the spacious wraparound deck and take in 120 feet of pristine waterfront. Spend your days swimming, kayaking, sunbathing, or simply enjoying the ever-changing beauty of the bay. The property is extremely private and peaceful, yet just steps from the private sandy association beach. A rare and special waterfront retreat, this quintessential cottage captures the effortless beauty of North Fork living—a place where every day feels like summer.