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Single family home for sale at 440 Grand Island Dr, Osterville, MA 02655 | MLS# 22502682 | Listing updated on 2026-09-01
Photo 1 of Single family home for sale at 440 Grand Island Dr, Osterville, MA 02655 | MLS# 22502682 | Listing updated on 2026-09-01
Photo 2 of Single family home for sale at 440 Grand Island Dr, Osterville, MA 02655 | MLS# 22502682 | Listing updated on 2026-09-01
Photo 3 of Single family home for sale at 440 Grand Island Dr, Osterville, MA 02655 | MLS# 22502682 | Listing updated on 2026-09-01
Photo 4 of Single family home for sale at 440 Grand Island Dr, Osterville, MA 02655 | MLS# 22502682 | Listing updated on 2026-09-01
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$7,250,000

Monthly Est:$36,086

  • Beds Icon7 Beds
  • Beds Icon
    11 Baths
  • Beds Icon11,546sqft

440 Grand Island Dr, Osterville, MA 02655

$36,086/moEst:

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  • 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 Cape Cod And Islands MLS-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    2

  • County

    Barnstable County

  • City

    Osterville

  • 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

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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 Golf

Road Maintenance Road Maintenance

Security Guard Security Guard

Beach Beach

deck 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

DateEventPrice

08/31/2026

Source: mls_logoCape Cod And Islands MLS-MA #22502682

Price Increased

$7,295,000 +0.62%

$632/sqft

08/31/2026

Source: mls_logoCape Cod And Islands MLS-MA #22502682

Price Decreased

$7,250,000 -6.45%

$628/sqft

12/19/2025

Source: mls_logoCape Cod And Islands MLS-MA #22502682

Price Decreased

$7,750,000 -3.12%

$671/sqft

06/02/2025

Source: mls_logoCape Cod And Islands MLS-MA #22502682

Listed for Sale

$8,000,000 +90.48%

$693/sqft

10/29/2018

Source: mls_logoCape Cod And Islands MLS-MA #21714810

Sold

$4,200,000 -1.18%

$364/sqft

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Getting Around 440 Grand Island Dr

Bike Score®

Bike Score

Somewhat Bikeable

26/100

Walk Score®

Walk Score

Car-Dependent

9/100

Transit Score®

Transit Score

No Nearby Transit

0/100

Data provided by Redfin

Nearby Homes

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