Oceanfront Options – Kailua Beach – Hawaii Real Estate – A complete listing of Hawaii Homes on Oahu Honolulu
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Oceanfront Options – Kailua Beach

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A classic, “Old Hawaii”-style beach-front estate with 96 linear feet of frontage on one of the most desirable sections of Kailua Beach has been placed on the market by LIST Sotheby’s International Realty. The property consists of two homes on two separate lots which are being sold together for $12,500,000. The main house, situated on a 28,917 square foot oceanfront lot, is priced at $9,850,000. The house fronting Kaapuni Drive, with a 12,438 square foot lot, is priced at $2,650,000 and is available for purchase either together with the main house, or after the main house is sold.

Occupied by the same kamaaina family since 1963, the property originally included a cottage which the owners lived in while planning and building their dream home. They collaborated with noted Hawaii architectural firm Hogan and Chapman on the design of the main house. This timeless, spacious beach-front home was completed in 1966 and remodeled several times over the years. Its 3,452 interior square footage is augmented by an additional 520 square feet of useable lanai space.

Architecturally, the home takes full advantage of the features of the site, commanding a sweeping view of Kailua Bay, the coastline, the offshore islands, and the sunrise. The manicured lawn is bordered by tropical plants, coco palms, and a naupaka hedge along the shoreline.

The main living area opens to the lanais and views of the ocean and gardens and connects to a two-story structure with the kitchen and dining room at ground level and the master suite on the upper level. A wraparound lanai and walk-in shower can be accessed from the lower level by an exterior stairway. On the opposite side, a second single-level wing includes an office/library and another bedroom and bath. Attached to the three-car garage are a workshop and studio with kitchen and bath, which can serve as a guest house or caretaker’s quarters.

In 1973, the owners built the second home on the property, a 2,377 square foot single-level structure with three bedrooms, three baths, a large kitchen, and a main living area that opens to outdoor lanais, a courtyard, and fenced gardens. The home also has ocean views and access to the sandy beach. An attached garage provides parking for two cars.

The newer structure repeats the “Old Hawaii” design motifs of the main house with shake roofing, hardwood flooring and trim, paved courtyards, and a fireplace.

“The homes my parents built on Kailua Beach reflect their love of the ocean and their appreciation of the spectacular natural beauty of the area,” said Gerrit Osborne. “They swam nearly every day and in age-group competition nationally. My mother was from a kamaaina family, but my father first came to Hawaii as captain of the Yale swimming team. He returned after serving in the Navy and worked with Hawaiian Dredging during construction of the Ala Moana Shopping Center. One of the unique features of the home is a concrete piling from the project which was laid horizontally and supports the roof of the mauka lanai.

“Another unique feature of the property is a flagpole originally erected just off the beach by my father. The home is commonly referred to by surfers and sailors in the area as ‘Flagpole Beach.’ It flies the American flag with the Hawaiian flag on the cross arms. When my parents were entertaining, which they did often, they would fly the guest’s flag of origin…and sometimes in the evening the cocktail flag. Raising and lowering the flag was a family ritual.”

The property is being shown by appointment by listing Realtors Mary Worrall and Kala Judd.

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