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

440 Grand Island Drive, Osterville, MA 02655

$7,250,000
Property Type: Residential Bedrooms: 7 Baths: 11 Square Footage: 11,546 Lot Size (sq. ft.): 47,916 Status: Active
Current Price: $7,250,000 List Date: 12/19/2025 Last Modified: 9/01/2026

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 ...

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 ...

Listing Details MLS# 22502682

Contract Info

Original List Price
8000000
List Price/SqFt
627.92

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

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

Sep Living Qtrs Info

Beds
2
Baths - Full
3
Baths - Total
3

DPR Eligibility

DPR Eligible
No

Room Types

Bedroom 2 Level
Second
Bedroom 3 Level
Second
Bedroom 4 Level
Second
Dining Room Level
First
Exercise Room Level
Basement
Game Room Level
Basement
Kitchen Level
First
Laundry Level
First
Living Room Level
First
Office Level
First
Primary Bedroom Level
First
Sunroom Level
First

More Information

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 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 Room Types: Bedroom 2; Bedroom 3; Bedroom 4; Dining Room; Exercise Room; Foyer; Game Room; Kitchen; Laundry; Living Room; Office; Primary Bedroom; Sunroom

Room Information

Room Name Level
Primary Bedroom First
Bedroom 2 Second
Bedroom 3 Second
Bedroom 4 Second
Foyer
Laundry First
Dining Room First
Living Room First
Kitchen First
Exercise Room Basement
Office First
Sunroom First
Game Room Basement
IDX
Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties
Listing Agent: Robert B Kinlin
Source MLS Verified
Last Updated: September - 01 - 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