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For sale
    • $7,750,000

    440 Grand Island Drive, Osterville, MA 02655

    7beds
    11,546sqft
    : 
    $48,159/mo
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    Single Family Residence
    Built in 2013
    1.1 Acres Lot
    $6,962,900 Zestimate®
    $671/sqft
    $385/mo HOA

    What's special

    Resort-style poolCovered front porchInviting sitting roomFinished lower levelFull second kitchenGenerously proportioned en-suite bedroomsLuxurious spa-like bath
    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.
    418 days
    |
    1,075
    |
    32
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Robert B Kinlin rkinlin@robertpaul.com,

    Berkshire Hathaway HomeServices Robert Paul Properties

    Source: CCIMLS,MLS#: 22502682MLS Logo

      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, Wine Cooler, Washer, Wall/Oven Cook Top, Range Hood, Security System, Refrigerator, Microwave, Indoor Grill, Electric Dryer, 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
      • Patio & porch: Deck, Porch, Patio
      • 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
      • Architectural style: Contemporary
      • 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: $671/sqft
      • Tax assessed value: $7,293,500
      • Annual tax amount: $59,471
      • Date on market: 6/2/2025
      • Cumulative days on market: 409 days
      • Road surface type: Paved

        Estimated market value

        $6,962,900

        $6.61M - $7.31M

        $5,518/mo

        Price history

        DateEventPrice
        9/5/2025Price change$7,750,000-3.1%$671/sqft
        Source: CCIMLS #22502682 Report a problem
        6/2/2025Listed for sale$8,000,000+90.5%$693/sqft
        Source: CCIMLS #22502682 Report a problem
        10/29/2018Sold$4,200,000-11.6%$364/sqft
        Source: CCIMLS #21714810 Report a problem
        8/15/2018Price change$4,750,000-5%$411/sqft
        Source: Sotheby's International Realty #21714810 Report a problem
        8/18/2017Listed for sale$5,000,000+31.6%$433/sqft
        Source: Sotheby's International Realty #21714810 Report a problem
        11/6/2014Sold$3,800,000+1.3%$329/sqft
        Source: Public Record Report a problem
        7/1/2010Sold$3,750,000+265.9%$325/sqft
        Source: CCIMLS #21002225 Report a problem
        5/21/2007Sold$1,025,000$89/sqft
        Source: CCIMLS #20603328 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$56,455 +4.9%$6,978,400 +1.2%
        2024$53,832 +11.5%$6,892,700 +19.1%
        2023$48,269 +9.7%$5,787,700 +26.7%
        2022$44,019 +0.8%$4,566,300 +9.7%
        2021$43,654 -4.2%$4,161,500 +0.1%
        2020$45,556 +9.2%$4,156,600 +12.3%
        2019$41,733 -1.5%$3,699,700 -2%
        2018$42,359 +6.6%$3,775,300 +2.2%
        2017$39,745 -2.3%$3,693,800 -1%
        2016$40,688 +8.8%$3,732,800 +8.3%
        2015$37,380 +2%$3,445,200 -0.1%
        2014$36,653 +9.8%$3,448,100 +5.8%
        2013$33,378 +3.4%$3,259,600 -0.5%
        2012$32,272 +56.8%$3,276,300 +49.3%
        2011$20,588 -7.6%$2,194,900 -11%
        2010$22,281 +26%$2,467,400 +11.3%
        2009$17,684 +221%$2,216,000 +351.3%
        2003$5,509 +24.8%$491,000
        2001$4,414 -12.5%$491,000 +17.7%
        1997$5,044 $417,200
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: Osterville

        Getting around

        8 / 100
        Car-Dependent
        26 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • District: Barnstable

        Source: CCIMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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