Ad #6250809
MLS #22502682
Privately sited within the prestigious Oyster Harbors golf
440 Grand Island Dr, Osterville, MA 02655
$7,750,000
7Beds
10Baths
11,546Sqft
1.1Acres
About this property
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 entertainingpleting 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.
Property Features
7 Beds
10 Baths
11,546 Sqft
Built in 2013
1.1 Acres
2 Stories
Oyster Harbors Club
On Golf Course
Open, Off Street
Siding: Shingle Siding
Shingle Roof
Has Swimming Pool
Has Fireplace
Propane (Heating), Oil, Forced Air
$59,471 / yr property tax
Barnstable County
Oyster Harbors Community
Additional Photos
Contact Information
Robert B Kinlin
Robert Paul Properties, Inc.
508-420-1414
Location
Listing Agent: Robert B Kinlin 508-420-1414
Broker: Robert Paul Properties, Inc. 508-863-4663 Listing Site
Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Robert Paul Properties, Inc. 508-863-4663 Listing Site
Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
GolfHomes.com
Printed Aug 11, 2026
Photo Gallery
$7,750,000
7
Beds
10
Baths
11,546
Sqft
440 Grand Island Dr, Osterville, MA 02655
By contacting this agent you agree to these Terms and Conditions.
MLS# 22502682
Privately sited within the prestigious Oyster Harbors golf
$7,750,000
440 Grand Island Dr, Osterville, MA 02655
7
Beds
10
Baths
11,546
Sqft
1.1
Acres
$7,750,000
440 Grand Island Dr, Osterville, MA 02655
7 Beds
10 Baths
11,546 Sqft
1.1 Acres
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 entertainingpleting 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.
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Property Details
HOME DETAILS
7 Beds
10 Baths
11,546 Sqft
Built in 2013
1.1 Acres
2 Stories
GOLF COURSE & VIEW
Oyster Harbors Club
On Golf Course
EXTERIOR
Open, Off Street
Siding: Shingle Siding
Shingle Roof
Has Swimming Pool
INTERIOR
Has Fireplace
Propane (Heating), Oil, Forced Air
FINANCIAL & COMMUNITY
$59,471 / yr property tax
Barnstable County
Oyster Harbors Community
See More Details
Location
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Ad Statistics
Ad Number
6250809
Viewed
969 times
Listing Status
Active
Added
Jun 02, 2025
Last Refreshed
Jul 03, 2026 06:17:28 PM
Listing Information
Data Source
Cape Cod & Islands Association of REALTORS®, Inc.
Source Property ID
22502682
Listing Agent: Robert B Kinlin 508-420-1414
Broker: Robert Paul Properties, Inc. 508-863-4663 Listing Site
Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Robert Paul Properties, Inc. 508-863-4663 Listing Site
Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
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