440 Grand Island Drive, Osterville, MA 02655 (MLS # 22502682)
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Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and casual seating area at one end and a full second kitchen with custom built-in grill and dining area at the other, all enclosed by retractable screens for effortless seasonal enjoyment. Tucked away on the main level, the primary suite offers a private sanctuary, with its own fireplace, luxurious spa-like bath, and refined home office. The comfort and sophistication continue on the second level with four generously proportioned en-suite bedrooms and an inviting sitting room. Designed for comfort and connection, the finished lower level offers a wine cellar, media room, game room, and fitness space. This lavish interior flows effortlessly to an equally impressive exterior, where lush landscaping surrounds a resort-style pool framed by expansive lounging areas-perfect for everything from quiet afternoons to grand entertaining. Completing this offering is a beautiful two-bedroom guest house providing privacy and comfort for visiting guests. Set within a prestigious gated enclave with coveted beach and dock rights, this remarkable estate is the perfect fusion of architectural sophistication and everyday warmth - an extraordinary offering in one of Cape Cod's most prestigious settings. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.
| DAYS ON MARKET | 276 | LAST UPDATED | 9/5/2025 |
|---|---|---|---|
| TRACT | Oyster Harbors | YEAR BUILT | 2013 |
| COMMUNITY | Mid-Cape | GARAGE SPACES | 3.0 |
| COUNTY | Barnstable | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| PRICE HISTORY | |
| Prior to Sep 5, '25 | $8,000,000 |
|---|---|
| Sep 5, '25 - Today | $7,750,000 |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Cooktop, Dishwasher, Dryer, Electric Water Heater, Indoor Grill, Microwave, Range Hood, Refrigerator, Washer, Wine Cooler |
| AREA | Mid-Cape |
| BASEMENT | Finished, Full, Interior Entry, Yes |
| CONSTRUCTION | Shingle Siding |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HOA DUES | 4620|Annually |
| INTERIOR | Breakfast Bar, Pantry, Recessed Lighting, Walk-in closet(s), Wet Bar |
| LOT | 1.1 acre(s) |
| LOT DESCRIPTION | Cleared, Level, Near Golf Course, On Golf Course |
| PARKING | Attached |
| POOL | Yes |
| POOL DESCRIPTION | Pool Cover, In Ground, Heated, Gunite, Private |
| SEWER | Private Sewer |
| STORIES | 2 |
| STYLE | Contemporary |
| SUBDIVISION | Oyster Harbors |
| TAXES | 59471 |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listed with Berkshire Hathaway HomeServices Robert Paul Properties
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