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$2,000,000
3 Beds ⋅ 3 Baths ⋅ 731801 MLS ⋅ ['Fee Simple'] Tenure
Perched along the coveted ridge of Omao Road, this classic island-style custom home offers breathtaking panoramic views, timeless craftsmanship, and exceptional privacy. From the moment you step through the handcrafted solid koa entry doors, you’ll appreciate the quality and character that define this one-of-a-kind residence. The dramatic great room features soaring cathedral ceilings and expansive walls of glass that fill the home with natural light while framing approximately 160-degree views of the Haupu and Kahili Mountain ranges. Homes on the prestigious Omao Road ridge are rarely offered for sale, and this exceptional property is coming to the market for the very first time. Designed to embrace Kauai’s indoor-outdoor lifestyle, the private pool area is surrounded by lush tropical landscaping and enjoys peaceful mountain vistas, creating a tranquil retreat for relaxing or entertaining. The meticulously curated gardens reflect years of thoughtful care and feature an impressive collection of rare exotic plants along with assorted heirloom palm trees.Throughout the home, exquisite genuine koa wood showcases the craftsmanship and warmth of Hawaii, including custom doors, window frames, baseboards, a built-in koa desk, bookshelves, and remarkable oversized koa pieces beneath the dining room chandelier—materials that are virtually impossible to source today. Downstairs rooms with private entrance are an added bonus! Recent improvements include: Beautifully remodeled primary bathroom Fresh interior and exterior paint Updated lighting fixtures and ceiling fans throughout New pool pump and filter wiring (July 2026) Sand pool filter installed in 2021 by Puni Nani Pools Additional features include: Built-in hurricane shelter Generator shed with tested KIUC electrical hookup Property professionally termite tented in March 2026 A short drive takes you to historic Koloa Town and then Poipu beaches with all of the amenities you need!

4100 Omao Rd, KOLOA

Listing courtesy of Hawaii Life.

$1,299,995
730680 MLS ⋅ ['Fee Simple'] Tenure
Rare opportunity to own 7.46 acres of vacant land off Omao Road on Kauaʻi’s South Shore. Conveniently located near Historic Kōloa Town, Poʻipū beaches, shopping, dining, and recreational activities, this property offers the perfect blend of privacy and accessibility. - Zoned Open with a portion Zoned R-2 - Property may allow for Three (3) Units. Buyer to verify with the appropriate County of Kauai agencies. A wide access approach leads to the larger portion of the property tucked away from the road, ideal for creating a private estate, farming, grazing, or multi-generational living. A stream borders much of the western boundary, adding to the peaceful rural charm of this unique property. The information herein may contain inaccuracies and is provided without warranty or guaranty of any kind. Agents and Buyers must independently verify with, but not limited to, the County of Kauai, licensed Inspectors, a HI real estate attorney, any and all information which Agents and Buyers deem potentially material or important to the Buyers’ purchase. Building square footage should be confirmed by a licensed Appraiser. Land square footage should be confirmed by a licensed Surveyor.

Omao Rd, KOLOA

Listing courtesy of Kauai Realty, Inc..

$2,125,000
5 Beds ⋅ 4 Baths ⋅ 730824 MLS ⋅ ['Fee Simple'] Tenure
Located in the desirable Omao neighborhood on Kauai's South Shore, this five-bedroom, four-bath residence offers a rare combination of privacy, flexibility, and island living less than ten minutes from Poipu's beaches, dining, golf, and shopping. Set on nearly half an acre of beautifully landscaped grounds, the property offers a private setting while remaining close to the area's most sought-after amenities. Centered around a sparkling swimming pool, covered lanai, and expansive outdoor living spaces, the home embraces Kauai's year-round indoor-outdoor lifestyle. Vaulted ceilings, hardwood floors, and abundant natural light create a warm and inviting atmosphere throughout the main residence. The updated kitchen features granite countertops, stainless steel appliances, and generous cabinetry, while the adjoining living and dining spaces are designed for both everyday living and entertaining. A spacious primary suite offers comfort and privacy, while the flexible floor plan provides room for guests, family, or changing lifestyle needs. Adding to the home's versatility, a separate two-bedroom wing connected by a breezeway offers exceptional flexibility as guest accommodations, a home office, creative studio, or multigenerational living space. Additional features include a 30-panel solar system, fully fenced grounds, mature fruit trees, exterior workshop and storage space, potting area, outdoor fitness space, and a two-car garage. Opportunities to own a private retreat with usable land, flexible living spaces, and resort-style amenities mere minutes from Poipu are exceedingly rare. This property offers the space, privacy, and lifestyle that make island living so special. If you would like to tour this property there are two videos for you, copy and paste this links into a new browser window: Property Overview https://bit.ly/4186UpaRoad Virtual Walk Through https://bit.ly/4186-tour

4186 Upa Rd, KOLOA

Listing courtesy of Hawaii Life.

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX 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.