Imagine stepping into a world of unparalleled luxury, where every detail is crafted for exclusivity and comfort. From the secluded elegance of a custom retreat in Oak Bluffs with soaring 15-foot ceilings to the historic charm of Cotuit’s General Mather House and the modern sophistication of a Winchester estate near Boston, these properties redefine upscale living. Priced between $2,795,000 and $3,125,000, each offers a unique blend of privacy, bespoke design, and timeless appeal, perfect for those seeking a year-round sanctuary or a seasonal escape.
63 Bayes Hill Road | $3,125,000


Casandra Hyland

Casandra Hyland
Situated in a tranquil neighborhood, this custom-designed home offers a sanctuary of privacy and sophistication. The first floor welcomes you with an open-concept layout, seamlessly blending the dining room, kitchen, and living space, while bypass siding doors provide flexible separation. Culinary enthusiasts will appreciate the gourmet kitchen, complete with custom cabinetry, high-end appliances, and expansive granite countertops. The primary bedroom, thoughtfully positioned away from the main living areas, boasts 15-foot ceilings, built-in bookshelves with a charming mid-1800s-style rolling ladder, a private bath, a spacious walk-in closet, and an attached office with access to the back deck. Upstairs, three bedrooms, two full bathrooms, and a versatile extra room await, ideal for an office or entertainment space. The finished basement adds even more potential, featuring a full bath, mudroom, garage access, and room for a game area or gym.
- Price:
- $3,125,000
- Size:
- 5,165 sq ft
- Contact:
- Casandra Hyland, Landmarks At Today Real Estate, 508.560.9901
188 Ocean View Avenue | $2,950,000


Adrienne G Siegel

Adrienne G Siegel
Set against the serene waterfront of Cotuit, the Captain Richard Snow Handy Estate offers a rare glimpse into timeless elegance. Known fondly as the General Mather House and listed on the National Register of Historic Places, this cherished property, held by the same family for 90 years, is a true legacy. Just steps from Riley’s and Loop Beach, it sits at the heart of the village, near the market, library, Kettle Ho, and harbor. Spanning 10 rooms, the home features five bedrooms and 3.5 baths, with each bedroom thoughtfully positioned near a full bathroom. Cozy up by one of several fireplaces or unwind on the secluded screened porch, caressed by summer ocean breezes. The picturesque half-acre lot blooms with rose and grape arbors, framed by mature Linden and Holly trees. Designed for year-round living, this estate invites unforgettable memories across every Cape Cod season.
- Price:
- $2,950,000
- Size:
- 3,740 sq ft
- Contact:
- Adrienne G Siegel, Strawberry Hill Real Estate, 508.775.8000
A Masterpiece Of Design And Craftsmanship | $2,795,000


Candice Macoul

Candice Macoul
Situated in a distinguished neighborhood, this exceptional residence embodies a perfect fusion of timeless elegance and modern sophistication. A grand foyer welcomes you with a striking curved staircase, setting a tone of refined luxury that permeates every corner. Expansive living spaces flow effortlessly, showcasing soaring ceilings, intricate custom millwork, and impeccable finishes. At the heart of the home lies a bespoke chef’s kitchen, equipped with professional-grade appliances, a cozy fireplace, and a practical adjoining mudroom—ideal for both culinary mastery and intimate gatherings. The opulent primary suite offers a resort-like escape with a spa-inspired bath and tranquil views, while three additional en-suite bedrooms ensure comfort for family or guests. Designed for seamless indoor-outdoor living, eight sets of French doors open to a stunning loggia adorned with marble columns, overlooking a sparkling heated saltwater pool. A heated driveway and front walk add thoughtful convenience.
- Price:
- $2,795,000
- Size:
- 5,233 sq ft
- Contact:
- Candice Macoul, Luxury Living Real Estate, 617.877.1998



















