440 Grand Island Dr Osterville, MA 02655
Osterville NeighborhoodEstimated payment $45,736/month
Highlights
- Marina
- Guest House
- Deeded access to the beach
- West Villages Elementary School Rated A-
- Golf Course Community
- Wine Cellar
About This Home
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 2-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. Inside, refined architectural detail defines elegant living and entertaining spaces, from the chef’s kitchen with granite islands and fireside sitting room to the spectacular sunroom with a bar, kitchen, and retractable screens. The main-level primary suite is a serene retreat, while four additional en-suite bedrooms and a sitting room await upstairs. The lower level includes a wine cellar, media room, gym, and game room. Outside, lush landscaping surrounds the resort-style pool and expansive lounging areas. Complete with beach and dock rights, this estate is an extraordinary offering in one of Cape Cod’s most prestigious settings.
Listing Agent
Berkshire Hathaway HomeServices Robert Paul Properties Listed on: 06/02/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $56,455
Year Built
- Built in 2013
Lot Details
- 1.1 Acre Lot
- Fenced Yard
- Landscaped Professionally
- Level Lot
- Cleared Lot
- Property is zoned RF
HOA Fees
- $385 Monthly HOA Fees
Parking
- 3 Car Attached Garage
- Parking Storage or Cabinetry
- Side Facing Garage
- Garage Door Opener
- Off-Street Parking
Home Design
- Contemporary Architecture
- Wood Roof
- Concrete Perimeter Foundation
Interior Spaces
- Wet Bar
- Coffered Ceiling
- Cathedral Ceiling
- Recessed Lighting
- French Doors
- Wine Cellar
- Family Room with Fireplace
- 7 Fireplaces
- Living Room with Fireplace
- Sitting Room
- Media Room
- Home Office
- Bonus Room
- Screened Porch
- Home Gym
- Home Security System
Kitchen
- Breakfast Bar
- Oven
- Indoor Grill
- Range with Range Hood
- Microwave
- Plumbed For Ice Maker
- Second Dishwasher
- Wine Refrigerator
- Kitchen Island
- Upgraded Countertops
Flooring
- Wood
- Wall to Wall Carpet
- Marble
- Ceramic Tile
Bedrooms and Bathrooms
- 7 Bedrooms
- Primary Bedroom on Main
- Fireplace in Primary Bedroom
- Custom Closet System
- Walk-In Closet
- Dual Vanity Sinks in Primary Bathroom
Laundry
- Laundry on main level
- Dryer
- Washer
- Sink Near Laundry
Finished Basement
- Basement Fills Entire Space Under The House
- Interior Basement Entry
Outdoor Features
- Heated In Ground Pool
- Deeded access to the beach
- Balcony
- Patio
- Outdoor Gas Grill
Utilities
- Central Heating and Cooling System
- Heating System Uses Oil
- Generator Hookup
- Power Generator
- Private Sewer
Additional Features
- Energy-Efficient Thermostat
- Guest House
- Property is near schools
Listing and Financial Details
- Assessor Parcel Number M:051 L:014002,2231336
Community Details
Overview
- Near Conservation Area
Amenities
- Shops
Recreation
- Marina
- Golf Course Community
Map
Home Values in the Area
Average Home Value in this Area
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 09/05/2025 09/05/25 | Price Changed | $7,750,000 | -3.1% | $671 / Sq Ft | |
| 06/02/2025 06/02/25 | For Sale | $8,000,000 | +90.5% | $693 / Sq Ft | |
| 10/29/2018 10/29/18 | Sold | $4,200,000 | -16.0% | $404 / Sq Ft | View Prior Sale |
| 09/06/2018 09/06/18 | Pending | -- | -- | -- | |
| 08/18/2017 08/18/17 | For Sale | $5,000,000 | -- | $481 / Sq Ft |
Source: MLS Property Information Network (MLS PIN)
MLS Number: 73383981
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