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.
For sale
$8,000,000
440 Grand Island Drive, Osterville, MA 02655
7beds
11,546sqft
Est.:
Single Family Residence
Built in 2013
1.1 Acres Lot
$7,289,100 Zestimate®
$693/sqft
$385/mo HOA
What's special
Resort-style poolCovered front porchInviting sitting roomFull second kitchenGenerously proportioned en-suite bedroomsLuxurious spa-like bathRefined home office
- 68 days
- on Zillow |
- 1,329 |
- 52 |
Zillow last checked: 7 hours ago
Listing updated: June 03, 2025 at 11:29am
Listed by:
Robert B Kinlin rkinlin@robertpaul.com,
Berkshire Hathaway HomeServices Robert Paul Properties
Source: CCIMLS,MLS#: 22502682

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 7
- Bathrooms: 11
- Full bathrooms: 9
- 1/2 bathrooms: 2
Primary bedroom
- Description: Flooring: Carpet,Door(s): French
- Features: Office/Sitting Area, Walk-In Closet(s), Recessed Lighting
- Level: First
Bedroom 2
- Description: Flooring: Carpet
- Features: Private Full Bath, Closet
- Level: Second
Bedroom 3
- Description: Flooring: Carpet
- Features: Private Full Bath, Closet
- Level: Second
Bedroom 4
- Description: Flooring: Carpet,Door(s): French
- Features: Private Full Bath, Closet
- Level: Second
Primary bathroom
- Features: Private Full Bath
Dining room
- Description: Flooring: Wood
- Features: Recessed Lighting, Built-in Features
- Level: First
Kitchen
- Description: Countertop(s): Granite,Flooring: Wood
- Features: Recessed Lighting, Breakfast Bar, Built-in Features, Kitchen Island, Pantry
- Level: First
Living room
- Description: Fireplace(s): Gas,Flooring: Wood,Door(s): French
- Features: Recessed Lighting, Cathedral Ceiling(s)
- Level: First
Heating
- Has Heating (Unspecified Type)
Cooling
- Central Air
Appliances
- Included: Cooktop, Washer, Wall/Oven Cook Top, Refrigerator, Microwave, Indoor Grill, Dishwasher, Electric Water Heater
- Laundry: Laundry Areas, Sink, Built-Ins, First Floor
Features
- Wet Bar, Recessed Lighting, Pantry, Linen Closet
- Flooring: Wood, Carpet, Tile
- Doors: French Doors
- Basement: Bulkhead Access,Interior Entry,Full,Finished
- Number of fireplaces: 6
- Fireplace features: Gas
Interior area
- Total structure area: 11,546
- Total interior livable area: 11,546 sqft
Video & virtual tour
Property
Parking
- Total spaces: 6
- Parking features: Garage - Attached
- Attached garage spaces: 3
Features
- Stories: 2
- Has private pool: Yes
- Pool features: Pool Cover, In Ground, Heated, Gunite
- Fencing: Fenced
Lot
- Size: 1.1 Acres
- Features: Conservation Area, School, House of Worship, Near Golf Course, Shopping, Public Tennis, Marina, Level, Cleared
Details
- Parcel number: 051014002
- Zoning: RF-1
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Foundation: Poured
- Roof: Shingle
Condition
- Actual
- New construction: No
- Year built: 2013
Utilities & green energy
- Sewer: Private Sewer
Community & HOA
Community
- Features: Golf
- Subdivision: Oyster Harbors
HOA
- Has HOA: Yes
- Amenities included: Road Maintenance, Security
- HOA fee: $4,620 annually
Location
- Region: Osterville
Financial & listing details
- Price per square foot: $693/sqft
- Tax assessed value: $6,978,400
- Annual tax amount: $57,908
- Date on market: 6/2/2025
- Road surface type: Paved
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