440 Grand Island Drive, Osterville, MA 02655 (MLS# 22502682)

440 Grand Island Drive, Osterville, MA 02655

$7,750,000

Virtual Tour

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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: 4/08/2026

Overview

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 w ... (Read more)

Listing Details MLS# 22502682

Contract Info

Original List Price: 8000000
List Price/SqFt: 671.23

Legal and Taxes

Street #: 440
Street Name: Grand Island
Street Suffix: Drive
County: Barnstable
Town: Barnstable
Village: Osterville
State: MA
Zip Code: 02655
Tax ID: 051-014-002
Estimated Annual Taxes: 59471
Tax Year: 2026
Building Assessments: 5010900
Total Assessment: 7293500
Title Reference - Book: C217695
Lead Base Paint: Unknown
Flood Ins Required: No
Mass Use Code: 109 - Residential, multiple houses
Nitrogen Sensitive Area: Yes
Other Assessments: 0
Title Reference - Page: No

General Property Info

Region: Mid-Cape
Subdivision: Oyster Harbors
School District: Barnstable
Zoning: RF-1
Property Sub-Type: Single Family Residence
Year Built: 2013
Renovated: No
Total Finished Space: 11546
Field Card SqFt: 6846
Additional Finished Space: 4700
Additional SqFt Source: Plans
Total Rooms: 16
Stories: 2
Private Pool: Yes
Private Dock: No
Leased Land: No
Lot Size SqFt: 47916
Lot Size Source: Assessor
Acres: 1.1
Irregular: Yes
Association: Yes
Fee Amount: 4620
Fee Frequency: Annually
Membership Required: Yes
Assoc Fee Year: 2025
Garage: Yes
# of Cars: 3
# of Parking Spaces: 6
Year Round: Yes
Bedrooms - Total: 7
Baths - Full: 9
Baths - Half: 2
Baths - Total: 11
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
Device Records: Video
Basement: Yes

Sep Living Qtrs Info

Beds: 2
Baths - Full: 3
Baths - Total: 3

Primary Bedroom

Primary Bedroom Level: First Floor
Special Door Access: French
Flooring: Carpet
Office/Sitting Area: Yes
Private Full Bath: Yes
Recessed Lighting: Yes
Walk-in Closet: Yes

Bedroom 2

Bedroom 2 Level: Second Floor
Flooring: Carpet
Closet: Yes
Private Full Bath: Yes

More Information

Bedroom 3

Bedroom 3 Level: Second Floor
Flooring: Carpet
Closet: Yes
Private Full Bath: Yes

Bedroom 4

Bedroom 4 Level: Second Floor
Flooring: Carpet
Special Door Access: French
Closet: Yes
Private Full Bath: Yes

Laundry Room

Laundry Room Level: First Floor
Flooring: Tile
Built-Ins: Yes
Laundry Areas: Yes
Sink: Yes

Living Room

Living Room Level: First Floor
Fireplace: Gas
Flooring: Wood
Special Door Access: French
Cathedral Ceiling: Yes
Recessed Lighting: Yes

Dining Room

Dining Room Level: First Floor
Flooring: Wood
Built-Ins: Yes
Recessed Lighting: Yes

Kitchen

Kitchen Level: First Floor
Countertops: Granite
Flooring: Wood
Pantry: Yes
Breakfast Bar: Yes
Built-Ins: Yes
Kitchen Island: Yes
Laundry Areas: Yes
Recessed Lighting: Yes

Other Room 1

Room Type: Exercise Room
Level: Basement

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

DPR Eligibility

DPR Eligible: No

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: Yes
Paved: Yes

Special Listing Cond

None: Yes

Lot Features

Cleared: Yes
Fenced/Enclosed: Yes
Interior Lot: Yes
Level: Yes

Year Built Desc

Actual: Yes

Basement Description

Bulkhead Access: Yes
Finished: Yes
Full: Yes
Interior Access: Yes

Association Fee Incl

Road Maintenance: Yes
Security: Yes

Parking Features

Off Street: Yes

Architectural Style

Contemporary: Yes

Garage Description

Attached: Yes
Direct Access: Yes
Garage Door Opener: Yes

Neighborhood Amen

Beach Access: Yes
Boat Dock: Yes
Golf Course: Yes

Foundation Details

Poured: Yes

Convenient To

Conservation Area: Yes
Golf Course: Yes
House of Worship: Yes
Marina: Yes
Public Tennis: Yes
School: Yes
Shopping: Yes

Floors

Carpet: Yes
Tile: Yes
Wood: Yes

Sewer

Private Sewer: Yes

Separate Living Qtrs

Detached: Yes
First Floor: Yes
Second Floor: Yes

Fencing

Fenced: Yes

Roof Description

Shingle: Yes

Siding Description

Shingle: Yes

Heating

Forced Air: Yes

Cooling

Central Air: Yes

Fuel Type

Oil: Yes
Propane: Yes

Water

Public: Yes

Hot Water

Water Heater: Yes

Foyer

Cathedral Ceiling: Yes
Closet: Yes

Hot Water Source

Electric: Yes

Exterior Features

Private Yard: Yes

Appliances

Countertop Range: Yes
Dishwasher: Yes
Electric Dryer: Yes
Indoor Grill: Yes
Microwave: Yes
Range Hood: Yes
Refrigerator: Yes
Security System: Yes
Wall/Oven Cook Top: Yes
Washer: Yes
Wine Cooler: Yes

Interior Features

Electric Dryer Hookup: Yes
Elevator: Yes
Linen Closet: Yes
Pantry: Yes
Recessed Lighting: Yes
Walk-In Closet(s): Yes
Washer Hookup: Yes
Wet Bar: Yes

Patio And Porch Features

Deck: Yes
Patio: Yes
Porch: Yes

Private Pool Description

Covered: Yes
Gunite: Yes
Heated: Yes
In Ground: Yes

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

Documents

Floor Plan ›

Property Details ›

Home Inspection Disclosure ›

Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties

Listing Agent: Robert B Kinlin

Last Updated: April - 08 - 2026

Broker Attribution: rkinlin@robertpaul.com

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 CC&I Assoc. of REALTORS, Inc include the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS, Inc 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. This site was last updated 02/14/2017. All properties are subject to prior sale, changes, or withdrawal. Copyright 2020© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved

440 Grand Island Drive, Osterville, MA 02655 (MLS# 22502682)