$7,750,000
440 Grand Island Drive, Osterville, MA 02655
7 Beds
9 Full Baths
2 Half Baths
11,546 Sq Ft
1.10 acres
3 Car Garage
MLS# 22502682 · Residential / (Single Family Residence)
Listed: 06/02/25 (listing data as of 07/30/26 at 3:09 pm)
Listed: 06/02/25 (listing data as of 07/30/26 at 3:09 pm)
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
Property Details
Property TypeResidential
(Single Family Residence)
(Single Family Residence)
StatusActive
MLS Number22502682
Year Built2013
Annual Taxes$59,471 (2026)
Total Assessment$7,293,500
Square Footage11,546
Price/Sq Ft$671/sq ft
Separate Living QuartersYes
Additional Finished Space4,700 sqft
Lot Size1.10 acres
Bedrooms7
Full Baths9
Half Baths2
Heat Source
Forced Air, Oil, Propane
Add'l Heating
Forced Air
Cooling A/C
Central Air
Association Fee
$4,620.00 (Annually)
Association Fee Includes
Road Maintenance, Security
Garage Spaces3
Days on Market423
WaterfrontNo
Private PoolYes
Private Pool Description
Covered, Gunite, Heated, In Ground
Fireplaces6
Lot Features
Cleared, Fenced/Enclosed, Interior Lot, Level
Bedroom Details
Primary Bedroom
- First Floor
- Carpet Flooring
- Office/Sitting Area
- Private Full Bath
- Recessed Lighting
- French Door Access
- Walk-in Closet
Bedroom 2
- Second Floor
- Closet
- Carpet Flooring
- Private Full Bath
Bedroom 3
- Second Floor
- Closet
- Carpet Flooring
- Private Full Bath
Bedroom 4
- Second Floor
- Closet
- Carpet Flooring
- Private Full Bath
- French Door Access
Living Area Details
Living Room
- First Floor
- Cathedral Ceiling
- Gas Fireplace
- Wood Flooring
- Recessed Lighting
- French Door Access
Dining Room
- First Floor
- Built-Ins
- Wood Flooring
- Recessed Lighting
Kitchen
- Pantry
- First Floor
- Breakfast Bar
- Built-Ins
- Wood Flooring
- Laundry Areas
- Recessed Lighting
Appliances
- Countertop Range
- Dishwasher
- Electric Dryer
- Indoor Grill
- Microwave
- Range Hood
- Refrigerator
- Security System
- Wall/Oven Cook Top
- Washer
- Wine Cooler
Exercise Room
- Basement
Home Office
- First Floor
Sun Room
- First Floor
Laundry Room
- First Floor
- Built-Ins
- Tile Flooring
- Laundry Areas
- Sink
Sep Living Qtrs Info
Baths - Full
3
Beds
2
Baths - Total
3
Convenient To
- Conservation Area
- Golf Course
- House of Worship
- Marina
- Public Tennis
- School
- Shopping
Exterior Features
- Private Yard
Interior Features
- Electric Dryer Hookup
- Elevator
- Linen Closet
- Pantry
- Recessed Lighting
- Walk-In Closet(s)
- Washer Hookup
- Wet Bar