Hawaii Living

314 Cook Pine Dr (Kapalua)

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314 Cook Pine Dr, Lahaina
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Description
Magnificent 5 bedroom, 5 1/2 bath home with the finest craftsmanship and materials in this very distinctive home behind the gates at Pineapple Hill at Kapalua. Sprawled across 2 lots and meticulously maintained, the former home of one of music's all time favorite musicians is now available for you to enjoy. Property also includes an approximately 464 square foot building ideal for workouts or to use as an office. Beautiful pool with cascading hot tub and private landscaped area for yoga and meditation. Main level with no steps are where you will find the 4 en suite guest bedrooms plus powder room, kitchen, dining area, entertainment room, and office. The master bedroom is accessed with beautifully curved stairway with huge master bath and master closet.
Past Activity
  • Aug 25, 2022 Sold for $7,900,000
  • Aug 12, 2022 Under Contract
  • Aug 17, 2021 Listed at $7,900,000
More Details
  • Owner, Tax & Resale History
  • Price / ft²: $1,093
  • Zoning: R-1
  • View: Ocean
  • Security Features: Security System, Smoke Detector(s)
  • TMK: 2420030770000
  • Courtesy: Coldwell Banker Island Prop-KP / 808-870-7060
  • MLS: 392686
About Pineapple Hill Kapalua
Pineapple Hill is an established, exclusive gated community within Kapalua Resort that has a unique blend of luxury living and stunning scenery. First developed in 1989, this sought-after neighborhood provides residents with privacy, exceptional amenities, and direct access to the Kapalua lifestyle.

The land Pineapple Hill occupies was part of an 1855 Royal Grant given to missionary Dr. Dwight Baldwin for his service to the Hawaiian people. Initially used for ranching and various crops, his son later focused cultivation on pineapple as the industry boomed. This agricultural use persevered i

  ... Read more
The MLS properties are based on information from the Multiple Listing Service of REALTORS® Association of Maui. Listings last updated on December 25, 2025.Information is deemed reliable but not guaranteed.
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  • Sold 8/25/22 at $7,900,000
    (List Price: $7,900,000)
Description
Magnificent 5 bedroom, 5 1/2 bath home with the finest craftsmanship and materials in this very distinctive home behind the gates at Pineapple Hill at Kapalua. Sprawled across 2 lots and meticulously maintained, the former home of one of music's all time favorite musicians is now available for you to enjoy. Property also includes an approximately 464 square foot building ideal for workouts or to use as an office. Beautiful pool with cascading hot tub and private landscaped area for yoga and meditation. Main level with no steps are where you will find the 4 en suite guest bedrooms plus powder room, kitchen, dining area, entertainment room, and office. The master bedroom is accessed with beautifully curved stairway with huge master bath and master closet.
    The MLS properties are based on information from the Multiple Listing Service of REALTORS® Association of Maui. Listings last updated on December 25, 2025.Information is deemed reliable but not guaranteed.
    • Aug 25, 2022 Sold for $7,900,000
    • Aug 12, 2022 Under Contract
    • Aug 17, 2021 Listed at $7,900,000
    Pineapple Hill is an established, exclusive gated community within Kapalua Resort that has a unique blend of luxury living and stunning scenery. First developed in 1989, this sought-after neighborhood provides residents with privacy, exceptional amenities, and direct access to the Kapalua lifestyle.

    The land Pineapple Hill occupies was part of an 1855 Royal Grant given to missionary Dr. Dwight Baldwin for his service to the Hawaiian people. Initially used for ranching and various crops, his son later focused cultivation on pineapple as the industry boomed. This agricultural use persevered i

      ... Read more
    Other Kapalua Homes
    $8,800,000
    710 Mahana Ridge St#Lot 46
    5 Bds | 6 Ba
    4,103 ft²
    $9,800,000
    94 Keoawa Pl
    5 Bds | 5.5 Ba
    7,199 ft²
    $5,950,000
    300 Mahana Ridge St
    4 Bds | 4.5 Ba
    3,156 ft²
    $9,900,000
    223 Plantation Club Dr#14
    3 Bds | 3.5 Ba
    5,366 ft²
     
    You do not own the land, but have the right to use the land until an expiration year. At expiration the ownership typically reverts back to the land owner.
    Buyer and Seller have reached an agreement and are under contract. The sale may be subject to one or more contingencies.
    We have handled many transactions for clients who purchase Hawaii real estate without visiting. By request, our network of agents can prepare thorough property videos to ensure you are familiar with every detail necessary. All documents can be signed remotely.
    Buyer and Seller have reached an agreement and are under contract. The sale is expected to close / record soon.
    We will be happy to work with you as a Buyer's agent. Call us to learn more: 808-943-9000.
    Note: A Seller's agent has a fiduciary responsibility towards the Seller. Working with a Buyer's agent objectives and goals are aligned, at no cost to you, the Buyer.
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    Includes estimated monthly mortgage payment, maintenance / HOA fees & property taxes. The estimate does not include insurance premiums.