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Designed by renowned architect Royal Barry Wills, this magnificent Oyster Harbors residence combines timeless elegance with a coveted resort lifestyle in one of Cape Cod's most sought-after communities. The stately white brick facade and lush plantings set the stage immediately upon approach, hinting at the inimitable architectural and design details throughout. Sophisticated yet refined interiors retain many original design elements by the late Richard FitzGerald and complement sweeping views of the Donald Ross-designed golf course that are captured from nearly every room. Across the first level, French doors seamlessly connect to multiple outdoor living areas, including a swimming pool, hot tub, brick patio, and expansive bluestone terrace overlooking the golf course. At the heart of the home, a Smallbone kitchen with a butler's pantry effortlessly flows into the adjacent sunroom, formal dining room, and living room. Offering the utmost privacy and convenience, the first-floor primary suite enjoys its own private patio, as well as a fireplace, walk-in closet, and luxurious bath. The second level includes two well-appointed bedrooms, an office, and two full baths. Perfect for staff or guests, an attached in-law suite above the garage provides two additional bedrooms with a kitchenette and living room. A true legacy property set behind the gates of Oyster Harbors, this extraordinary residence delivers the best of Cape Cod living.
General Information for 245 North Bay Road Osterville, MA 02655 |
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| Town | Barnstable |
| Village | Osterville |
| County | Barnstable |
| Stories | 2 |
| Style | Cape Cod |
| SQFT | 4,637 |
| Status | Available |
| Listing Number | 22504570 (CCIMLS) |
Rooms Information for 245 North Bay Road Osterville, MA 02655 |
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| Family Room | 0X0 |
| Kitchen Features | 0X0 |
| Dining Room | 0X0 |
| Bedroom | 0X0 |
| Bedroom 1 | 0X0 |
| Bedroom 2 | 0X0 |
| Bedroom 3 | 0X0 |
| Bedroom 4 | 0X0 |
Interior Information for 245 North Bay Road Osterville, MA 02655 |
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| Basement | Partial |
| Fireplace | Yes |
Exterior Information for 245 North Bay Road Osterville, MA 02655 |
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| Lot Size | 1.01 acres |
| Lot Description | Marina School Near Golf Course Shopping South of Route 28 |
| Construction | Brick Clapboard |
| Garage | 2 Car Garage |
| Parking | Spaces: 4 |
| Lot | Marina School Near Golf Course Shopping South of Route 28 |
| Sewer | Septic Tank |
| Exterior Features | Outdoor Shower |
| Pool | Heated In Ground |
Neighborhood Information for 245 North Bay Road Osterville, MA 02655 |
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| Neighborhood Amenities | Road Maintenance Security |
Schools information for 245 North Bay Road Osterville, MA 02655 |
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| Elementary | Barnstable |
| Middle | Barnstable |
| High | Barnstable |
| General Area Public, Private School and College Information | |
Miscellaneous Information for 245 North Bay Road Osterville, MA 02655 |
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| Year Built | 1988 |
| Association Fee | 4620 |
| Taxes | $29,644 /Yr |
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| Condo | Data |
|---|---|
| Units | 6,780 |
| Avg Price | $934,215 |
| Avg Days Listed | 99 |
| Total New Listings | 2 |
| House | Data |
|---|---|
| Units | 12,283 |
| Avg Price | $1,263,989 |
| Avg Days Listed | 83 |
| Total New Listings | 22 |
| Multi-Family | Data |
|---|---|
| Units | 2,096 |
| Avg Price | $1,305,403 |
| Avg Days Listed | 107 |
| 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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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 09/17/2025. All properties are subject to prior sale, changes, or withdrawal.
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