- Overview
- Description
- Property Details
- Location
- HOA Management
- Facts & Features
- Getting Around
- Nearby Homes
$7,250,000
Monthly Est:$36,086
7 Beds
- 11 Baths
9 full baths + 2 half baths
11,546sqft
440 Grand Island Dr, Osterville, MA 02655
$7,250,000
$36,086/moEst:
Get Pre-Approved
Single Family Residence
Built in 2013
$385/mo HOA
1.1 acres lot
$628/sq.ft
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 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.
- Houzeo last checked: 10 hours ago
- Listing updated: September 1, 2026 at 12:57 pm
- Listing Provided by: Robert B Kinlin (508) 420-1414204 | Berkshire Hathaway HomeServices Robert Paul Properties (508) 420-1414
- Source: Cape Cod And Islands MLS-MA | MLS#: 22502682

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
2
County
City
Neighborhood
--
Year Built
2013
HOA Fees
$385/mo
Finished Area
11,546 sqft
Lot Size
1.1 acres lot
Basement Area
- sqft
MLS Name
Cape Cod And Islands MLS
MLS Number
22502682
MLS Status
Active
Days on Market
294
Cumulative Days on Market
456

Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Download App
Continue Your Journey in App
Find your dream home, receive real-time updates, and many more!
Location
HOA Management
N/A
HOA Fees
$4,620/ Annually
Amenities
Amenities and services may be covered by one or multiple associations and service providers.
Golf
Road Maintenance
Security Guard
Beach
deck
Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 7
Bathrooms: 11
Interior
Heating
Propane, Forced Air, Oil
Cooling
Central Air
Interior Features
Walk In Closet(s), Linen Closet, Pantry, Recessed Lighting, Wet Bar, Kitchen Island, Breakfast Bar
Flooring
Wood, Tile, Carpet
Exterior Features
Private Yard
Appliances
Water Heater, Wine Cooler, Range Hood, Countertop Range, Dishwasher, Indoor Grill, Microwave, Refrigerator, Wall/oven Cook Top, Washer
Construction
Year Built
Year Built: 2013
Home type
Single Family Residence
Foundation Details
Poured
Construction Materials
Shingle Siding
Roof
Shingle
Utilities & Energy
Pool Features
Covered, Gunite, Heated, In Ground
Basement
Bulkhead Access, Interior Access, Finished, Full
Water Source
Public
Parking Features
Garage Door Opener, Direct Access, Off Street
Laundry Features
Washer Hookup, Electric Dryer Hookup, Electric Dryer
Security Features
Security System
Association Amenities
Boat Dock, Beach Access, Road Maintenance, Security, Golf Course
Other Features
Subdivision Name
Oyster Harbors
Patio And Porch Features
Deck, Patio, Porch
Lot Features
Interior Lot, Cleared, Fenced/enclosed, Level
Price History
| Date | Event | Price |
|---|---|---|
08/31/2026 Source: | Price Increased | $7,295,000 +0.62% $632/sqft |
08/31/2026 Source: | Price Decreased | $7,250,000 -6.45% $628/sqft |
12/19/2025 Source: | Price Decreased | $7,750,000 -3.12% $671/sqft |
06/02/2025 Source: | Listed for Sale | $8,000,000 +90.48% $693/sqft |
10/29/2018 Source: | Sold | $4,200,000 -1.18% $364/sqft |
Show more
Getting Around 440 Grand Island Dr
Bike Score®
Somewhat Bikeable
26/100
Walk Score®
Car-Dependent
9/100
Transit Score®
No Nearby Transit
0/100
Data provided by Redfin
Nearby Homes
Find Homes by Property Features in Osterville, MA
Based on information from the Cape Cod and Islands Multiple Listing Service, Inc. through Oct 09, 2026, 02:30PM. Information is provided exclusively for consumers’ personal, non-commercial use, it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and the data is deemed reliable but is not guaranteed accurate by the MLS. This website may not include listings or property addresses of sellers who have directed their listing brokers to withhold their listing or their property address from display on the Internet. © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
Advertising Broker: Derek Greene | The Greene Realty Group














