For Sale
Single family home for sale at 440 Grand Is Dr, Osterville, MA 02655 | MLS# 73383981 | Listing updated on 2026-09-04
Photo 1 of Single family home for sale at 440 Grand Is Dr, Osterville, MA 02655 | MLS# 73383981 | Listing updated on 2026-09-04
Photo 2 of Single family home for sale at 440 Grand Is Dr, Osterville, MA 02655 | MLS# 73383981 | Listing updated on 2026-09-04
Photo 3 of Single family home for sale at 440 Grand Is Dr, Osterville, MA 02655 | MLS# 73383981 | Listing updated on 2026-09-04
Photo 4 of Single family home for sale at 440 Grand Is Dr, Osterville, MA 02655 | MLS# 73383981 | Listing updated on 2026-09-04
38+
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Street View

$7,250,000

Monthly Est:$36,086

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

440 Grand Is Dr, Osterville, MA 02655

$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: 12 hours ago
  • Listing updated: September 4, 2026 at 7:05 am
  • Listing Provided by: Robert Kinlin (508) 648-2739 | Berkshire Hathaway HomeServices Robert Paul Properties (508) 420-1414
  • Source: MLS Property Information Network-MA | MLS#: 73383981 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • 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

    MLS Property Information Network

  • MLS Number

    73383981

  • MLS Status

    Active

  • Days on Market

    488

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Location

HOA Management

N/A

HOA Fees

$4,620/ Annually

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

    Central, Oil, Fireplace(s), Fireplace

  • Flooring

    Wood, Tile, Carpet, Marble, Flooring Wood, Flooring Stone/ceramic Tile, Flooring Wall To Wall Carpet

  • Sewer

    Private Sewer

  • Exterior Features

    Porch, Porch Screened, Patio, Balcony, Pool Inground Heated, Professional Landscaping, Fenced Yard, Guest House, Outdoor Gas Grill Hookup

  • Cooling

    Central Air

  • Appliances

    Range, Oven, Dishwasher, Microwave, Indoor Grill, Refrigerator, Washer, Dryer, Wine Refrigerator, Range Hood, Plumbed For Ice Maker

  • Interior Features

    Cathedral Ceiling(s), Coffered Ceiling(s), Wet Bar, Home Office, Sitting Room, Wine Cellar, Media Room, Bonus Room, Exercise Room, Wet Bar, Elevator

Construction

  • Year Built

    Year Built: 2013

  • Home type

    Single Family Residence

  • Roof

    Wood

  • Architectural Style

    Contemporary

  • Foundation Details

    Concrete Perimeter

Utilities & Energy

  • Pool Features

    Pool Inground Heated

  • Electric

    Generator, Generator Connection

  • Fireplace Features

    Family Room, Living Room, Master Bedroom

  • Utilities

    For Gas Range, For Electric Dryer, Washer Hookup, Icemaker Connection, Generator Connection, Outdoor Gas Grill Hookup

  • Security Features

    Security System

  • Laundry Features

    Closet/cabinets Custom Built, Flooring Marble, Electric Dryer Hookup, Washer Hookup, Sink, First Floor

  • Basement

    Full, Finished, Interior Entry

  • Parking Features

    Attached, Garage Door Opener, Storage, Garage Faces Side, Off Street

  • Water Source

    Public

Other Features

  • Lot Features

    Cleared, Level

  • Community Features

    Shopping, Golf, Conservation Area, House Of Worship, Marina, Private School

  • Patio And Porch Features

    Porch, Screened, Patio

Price History

DateEventPrice

08/31/2026

Source: mls_logoMLS Property Information Network-MA #73383981

Price Increased

$7,295,000 +0.62%

$632/sqft

08/31/2026

Source: mls_logoMLS Property Information Network-MA #73383981

Price Decreased

$7,250,000 -6.45%

$628/sqft

09/05/2025

Source: mls_logoMLS Property Information Network-MA #73383981

Price Decreased

$7,750,000 -3.12%

$671/sqft

06/02/2025

Source: mls_logoMLS Property Information Network-MA #73383981

Listed for Sale

$8,000,000

$693/sqft

Nearby Homes

Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 02, 2026, 09:00AM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.

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