440 Grand Island Drive, Osterville, MA 02655 (MLS# 22502682)
440 Grand Island Drive, Osterville, MA 02655
$7,750,000
Property Type:
Residential
Bedrooms:
7
Baths:
11
Square Footage:
11,546
Lot Size (sq. ft.):
47,916
Status:
Active
Current Price:
$7,750,000
List Date:
12/19/2025
Last Modified:
12/19/2025
Description
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
Supplements: 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.
More Information MLS# 22502682
Contract Info
List Price/SqFt: 671.23
Status: Active
Original List Price: 8000000
List Price: $7,750,000
Current Price: $7,750,000
List Date: 2025-06-02
Legal and Taxes
Town: Barnstable
Village: Osterville
Estimated Annual Taxes: 57908
Building Assessments: 4163400
Other Assessments: 592900
Total Assessment: 6978400
Title Reference - Book: C217695
Title Reference - Page: 0
Flood Ins Required: No
Lead Base Paint: Unknown
Mass Use Code: 109 - Residential, multiple houses
Nitrogen Sensitive Area: Yes
Street #: 440
Street Name: Grand Island
Street Suffix: Drive
County: Barnstable
State: MA
Zip Code: 02655
Tax ID: 051-014-002
Tax Year: 2025
General Property Info
Region: Mid-Cape
School District: Barnstable
Zoning: RF-1
Property Sub-Type: Single Family Residence
Renovated: No
Stories: 2
Total Rooms: 16
Field Card SqFt: 6846
Additional Finished Space: 4700
Additional SqFt Source: Plans
Basement: Yes
Baths - Half: 2
Association: Yes
Fee Amount: 4620
Fee Frequency: Annually
Private Dock: No
Private Pool: Yes
Lot Size SqFt: 47916
Leased Land: No
Membership Required: Yes
Lot Size Source: Assessor
Acres: 1.1
Irregular: Yes
Assoc Fee Year: 2025
Garage: Yes
# of Cars: 3
# of Parking Spaces: 6
Year Round: Yes
Separate Living Qtrs: Yes
Golf Course Front: No
Golf Course View: No
Waterfront: No
Waterview: No
Mi. to Beach Comments: Deeded Beach and Dock Rights
Fireplace: Yes
# Fireplaces: 6
Property Includes Recording Devices: Yes
Subdivision: Oyster Harbors
Year Built: 2013
Total Finished Space: 11546
Bedrooms - Total: 7
Baths - Full: 9
Baths - Total: 11
Remarks & Misc
Public Remarks: 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
Directions to Property: Bridge Street to Oyster Harbors Gatehouse.
Street Description
Assoc Maintained: 1
Paved: 1
Special Listing Cond
None: 1
Lot Features
Cleared: 1
Fenced/Enclosed: 1
Interior Lot: 1
Level: 1
Year Built Desc
Actual: 1
Basement Description
Bulkhead Access: 1
Finished: 1
Full: 1
Interior Access: 1
Association Fee Incl
Road Maintenance: 1
Security: 1
Parking Features
Off Street: 1
Architectural Style
Contemporary: 1
Garage Description
Attached: 1
Direct Access: 1
Garage Door Opener: 1
Sep Living Qtrs Info
Baths - Full: 3
Beds: 2
Baths - Total: 3
Neighborhood Amen
Beach Access: 1
Boat Dock: 1
Golf Course: 1
Foundation Details
Poured: 1
Convenient To
Conservation Area: 1
Golf Course: 1
House of Worship: 1
Marina: 1
Public Tennis: 1
School: 1
Shopping: 1
Floors
Carpet: 1
Tile: 1
Wood: 1
Sewer
Private Sewer: 1
Separate Living Qtrs
Detached: 1
First Floor: 1
Second Floor: 1
Fencing
Fenced: 1
Roof Description
Shingle: 1
Siding Description
Shingle: 1
Primary Bedroom
Primary Bedroom Level: First Floor
Flooring: Carpet
Office/Sitting Area: 1
Private Full Bath: 1
Recessed Lighting: 1
Special Door Access: French
Walk-in Closet: 1
Heating
Forced Air: 1
Bedroom 2
Bedroom 2 Level: Second Floor
Closet: 1
Flooring: Carpet
Private Full Bath: 1
Cooling
Central Air: 1
Bedroom 3
Bedroom 3 Level: Second Floor
Closet: 1
Flooring: Carpet
Private Full Bath: 1
Fuel Type
Oil: 1
Propane: 1
Bedroom 4
Bedroom 4 Level: Second Floor
Closet: 1
Flooring: Carpet
Private Full Bath: 1
Special Door Access: French
Water
Public: 1
Hot Water
Water Heater: 1
Foyer
Cathedral Ceiling: 1
Closet: 1
Hot Water Source
Electric: 1
Laundry Room
Laundry Room Level: First Floor
Built-Ins: 1
Flooring: Tile
Laundry Areas: 1
Sink: 1
Living Room
Living Room Level: First Floor
Cathedral Ceiling: 1
Fireplace: Gas
Flooring: Wood
Recessed Lighting: 1
Special Door Access: French
Dining Room
Dining Room Level: First Floor
Built-Ins: 1
Flooring: Wood
Recessed Lighting: 1
Kitchen
Pantry: 1
Kitchen Level: First Floor
Breakfast Bar: 1
Built-Ins: 1
Countertops: Granite
Flooring: Wood
Kitchen Island: 1
Laundry Areas: 1
Recessed Lighting: 1
Other Room 1
Room Type: Exercise Room
Level: Basement
Exterior Features
Private Yard: 1
Other Room 2
Room Type: Home Office
Level: First Floor
Other Room 3
Room Type: Sun Room
Level: First Floor
Other Room 4
Room Type: Game Room
Level: Basement
Appliances
Countertop Range: 1
Dishwasher: 1
Electric Dryer: 1
Indoor Grill: 1
Microwave: 1
Range Hood: 1
Refrigerator: 1
Security System: 1
Wall/Oven Cook Top: 1
Washer: 1
Wine Cooler: 1
Interior Features
Electric Dryer Hookup: 1
Elevator: 1
Linen Closet: 1
Pantry: 1
Recessed Lighting: 1
Walk-In Closet(s): 1
Washer Hookup: 1
Wet Bar: 1
Patio And Porch Features
Deck: 1
Patio: 1
Porch: 1
Private Pool Description
Covered: 1
Gunite: 1
Heated: 1
In Ground: 1
Property Features
Street Description: Assoc Maintained; Paved
Special Listing Cond: None
Architectural Style: Contemporary
Year Built Desc: Actual
Basement Description: Bulkhead Access; Finished; Full; Interior Access
Foundation Details: Poured
Lot Features: Cleared; Fenced/Enclosed; Interior Lot; Level
Association Fee Incl: Road Maintenance; Security
Neighborhood Amen: Beach Access; Boat Dock; Golf Course
Garage Description: Attached; Direct Access; Garage Door Opener
Parking Features: Off Street
Separate Living Qtrs: Detached; First Floor; Second Floor
Convenient To: Conservation Area; Golf Course; House of Worship; Marina; Public Tennis; School; Shopping
Primary Bedroom: Office/Sitting Area; Private Full Bath; Recessed Lighting; Walk-in Closet
Bedroom 2: Closet; Private Full Bath
Bedroom 3: Closet; Private Full Bath
Bedroom 4: Closet; Private Full Bath
Foyer: Cathedral Ceiling; Closet
Laundry Room: Built-Ins; Laundry Areas; Sink
Living Room: Cathedral Ceiling; Recessed Lighting
Dining Room: Built-Ins; Recessed Lighting
Kitchen: Breakfast Bar; Built-Ins; Kitchen Island; Laundry Areas; Pantry; Recessed Lighting
Appliances: Countertop Range; Dishwasher; Electric Dryer; Indoor Grill; Microwave; Range Hood; Refrigerator; Security System; Wall/Oven Cook Top; Washer; Wine Cooler
Floors: Carpet; Tile; Wood
Interior Features: Electric Dryer Hookup; Elevator; Linen Closet; Pantry; Recessed Lighting; Walk-In Closet(s); Washer Hookup; Wet Bar
Patio And Porch Features: Deck; Patio; Porch
Private Pool Description: Covered; Gunite; Heated; In Ground
Exterior Features: Private Yard
Fencing: Fenced
Roof Description: Shingle
Siding Description: Shingle
Sewer: Private Sewer
Heating: Forced Air
Cooling: Central Air
Fuel Type: Oil; Propane
Water: Public
Hot Water: Water Heater
Hot Water Source: Electric
Floor Plan ›
Listing Office:
Berkshire Hathaway HomeServices Robert Paul Properties
Listing Agent:
Robert B Kinlin
Last Updated: December - 19 - 2025
Broker Attribution:
rkinlin@robertpaul.com
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