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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.
General Information for 440 Grand Island Drive Osterville, MA 02655 |
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Town | Barnstable |
Village | Osterville |
County | Barnstable |
Stories | 2 |
SQFT | 11,546 |
Status | Available |
Listing Number | 22502682 (CCIMLS) |
Rooms Information for 440 Grand Island Drive Osterville, MA 02655 |
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Family Room | 0X0 Fireplace(s): Gas Flooring: Wood Door(s): French Recessed Lighting Cathedral Ceiling(s) |
Kitchen Features | 0X0 Countertop(s): Granite Flooring: Wood Recessed Lighting Breakfast Bar Built-in Features Kitchen Island Pantry |
Dining Room | 0X0 Flooring: Wood Recessed Lighting Built-in Features |
Laundry | Laundry Areas Sink Built-Ins First Floor |
Bedroom | 0X0 Flooring: Carpet Door(s): French Office/Sitting Area Walk-In Closet(s) Recessed Lighting |
Master Bath Features | Private Full Bath |
Bedroom 1 | 0X0 Flooring: Carpet Door(s): French Office/Sitting Area Walk-In Closet(s) Recessed Lighting |
Bedroom 2 | 0X0 Flooring: Carpet Private Full Bath Closet |
Bedroom 3 | 0X0 Flooring: Carpet Private Full Bath Closet |
Bedroom 4 | 0X0 Flooring: Carpet Door(s): French Private Full Bath Closet |
Interior Information for 440 Grand Island Drive Osterville, MA 02655 |
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Basement | Bulkhead Access Interior Entry Full Finished |
Interior Features | Wet Bar Recessed Lighting Pantry Linen Closet |
Fireplace | Yes |
Appliances | Cooktop Washer Wall/Oven Cook Top Refrigerator Microwave Indoor Grill Dishwasher Electric Water Heater |
Exterior Information for 440 Grand Island Drive Osterville, MA 02655 |
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Lot Size | 1.10 acres |
Lot Description | Conservation Area School House of Worship Near Golf Course Shopping Public Tennis Marina Level Cleared |
Construction | Shingle Siding |
Garage | 3 Car Garage |
Parking | Spaces: 6 |
Lot | Conservation Area School House of Worship Near Golf Course Shopping Public Tennis Marina Level Cleared |
Sewer | Private Sewer |
Pool | Pool Cover In Ground Heated Gunite |
Neighborhood Information for 440 Grand Island Drive Osterville, MA 02655 |
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Neighborhood Amenities | Road Maintenance Security |
Schools information for 440 Grand Island Drive Osterville, MA 02655 |
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Elementary | Barnstable |
Middle | Barnstable |
High | Barnstable |
General Area Public, Private School and College Information | |
Miscellaneous Information for 440 Grand Island Drive Osterville, MA 02655 |
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Year Built | 2013 |
Association Fee | 4620 |
Taxes | $57,908 /Yr |
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Condo | Data |
---|---|
Units | 6,954 |
Avg Price | $993,061 |
Avg Days Listed | 96 |
Total New Listings | 0 |
House | Data |
---|---|
Units | 12,521 |
Avg Price | $1,306,878 |
Avg Days Listed | 79 |
Total New Listings | 13 |
Multi-Family | Data |
---|---|
Units | 1,946 |
Avg Price | $1,274,040 |
Avg Days Listed | 105 |
Total New Listings | 0 |
For a more detailed market analyis one of our real estate agents can provide you with a full report.
Address | Closing Date | List Price | Closing Price | % of List Price |
---|---|---|---|---|
42 Pond Street Osterville, MA 02655 |
01/03/2025 | $1,348,000 | $1,300,000 | 96% |
21 Nathans Way Osterville, MA 02655 |
12/16/2024 | $2,950 | $2,950 | 100% |
146 Wintergreen Circle Osterville, MA 02655 |
12/16/2024 | $799,000 | $780,000 | 98% |
3040 Falmouth Rd. A1 Osterville, MA 02655 |
12/15/2024 | $1,800 | $1,800 | 100% |
16 Second Avenue 5A Osterville, MA 02655 |
12/06/2024 | $649,000 | $610,000 | 94% |
920 Main Street 4 Osterville, MA 02655 |
12/05/2024 | $633,000 | $595,000 | 94% |
920A Main Street 17 Osterville, MA 02655 |
11/27/2024 | $85,000 | $75,000 | 88% |
17 Chine Way Osterville, MA 02655 |
11/26/2024 | $1,295,000 | $1,275,000 | 98% |
82 Blanid Road Osterville, MA 02655 |
11/26/2024 | $1,500,000 | $1,500,000 | 100% |
298 Starboard Lane Osterville, MA 02655 |
11/21/2024 | $2,695,000 | $2,500,000 | 93% |
39 Tower Hill Road 1A 1A Osterville, MA 02655 |
11/19/2024 | $630,000 | $610,000 | 97% |
33 Waterfield Road Osterville, MA 02655 |
11/18/2024 | $1,050,000 | $1,050,000 | 100% |
28 Bayview Road Osterville, MA 02655 |
11/15/2024 | $4,150,000 | $4,150,000 | 100% |
34 Rebecca Lane Osterville, MA 02655 |
11/04/2024 | $544,000 | $540,000 | 99% |
201 Old Mill Road Osterville, MA 02655 |
11/01/2024 | $2,399,000 | $2,250,000 | 94% |
92 Concord Lane Osterville, MA 02655 |
10/31/2024 | $3,500 | $3,500 | 100% |
22 Marion Way Osterville, MA 02655 |
10/31/2024 | $850,000 | $845,000 | 99% |
263 Tower Hill Road Osterville, MA 02655 |
10/28/2024 | $1,195,000 | $1,250,000 | 105% |
65 Deerfield Road Osterville, MA 02655 |
10/24/2024 | $940,000 | $890,000 | 95% |
13 South Street Osterville, MA 02655 |
10/20/2024 | $2,500 | $2,500 | 100% |
39 Tower Hill Road 5A Osterville, MA 02655 |
10/11/2024 | $689,000 | $660,000 | 96% |
42 Yawl Road Osterville, MA 02655 |
10/11/2024 | $628,000 | $628,000 | 100% |
812 Main Street Osterville, MA 02655 |
10/07/2024 | $1,000 | $1,000 | 100% |
51 Poplar Drive Osterville, MA 02655 |
10/03/2024 | $749,000 | $749,000 | 100% |
104 Great Bay Road Osterville, MA 02655 |
06/25/2024 | $7,995,000 | $8,250,000 | 103% |
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Listing: 1 of 1 | Updated 14 minutes ago |
Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Kinlin Grover Compass include the name of the listing broker. Neither the listing company nor Kinlin Grover Compass shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
This site was last updated 06/11/2025. All properties are subject to prior sale, changes, or withdrawal.
Kinlin Grover Compass has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.
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