244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
SEE ALL PHOTOS
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
244 Awakea Road
For Sale

244 Awakea Road

244 Awakea Road, Kailua, HI 96734

$3,295,000
Rarely available in Kailua Estates, 244 Awakea Rd is a beautifully remodeled plantation-style property on a spacious 10,000 sq ft lot just a short stroll to Kailua Beach and minutes to Kailua Town. Fully renovated in 2019, the property offers approximately 3,150 sq ft of total living space with a versatile multi-dwelling layout ideal for investors, multi-generational living, or those seeking flexible income potential.

The main home features 3 bedrooms, 2 bathrooms plus a den, with vaulted ceilings, hardwood flooring, a walk-in pantry, and seamless indoor-outdoor living. In addition, the property includes a spacious 1-bedroom cottage with high ceilings and a separate 2-bedroom, 1-bath ADU, both beautifully designed and tenant occupied with strong income potential. A dedicated storage and yoga room adds additional flexibility for wellness, workspace, or lifestyle use.

Located in one of Kailua's most desirable beachside neighborhoods, enjoy easy access to Kailua and Lanikai beaches, Kalapawai Market, and local shops and dining. A rare opportunity to own a flexible compound in a prime location offering both lifestyle and income potential.

5/17/2026 2:00PM - 5:00PM HST

6
beds

4
baths

3,150 Sq.Ft. LIVING AREA

10,000 Sq.Ft. lot

Jason Carey

Jason Carey

Features & Amenities

Interior

  • total bedrooms6
  • Total bathrooms4
  • full bathrooms4
  • Flooring Ceramic Tile, Hardwood, Vinyl
  • other interior Features Bedroom on Main Level, Full Bath on Main Level

Area & Lot

  • Status For Sale
  • OPEN HOUSE

    5/17/2026 2:00PM - 5:00PM HST

  • Living Area3,150 Sq.Ft.
  • Total Area3,590 Sq.Ft.
  • Lot Area10,000 Sq.Ft.
  • MLS® ID202608800
  • TypeResidential
  • YEAR BUILT1947
  • NeighborhoodKailua
  • Architecture StylesCottage, Detached, Multiplex
  • View DescriptionGarden
  • Elementary SchoolKainalu
  • Middle SchoolKailua
  • High SchoolKalaheo

Exterior

  • STORIES1
  • water SourcePublic
  • utilitiesAbove Ground Utilities, Electricity Available, High Speed Internet Available, Sewer Available, Water Available
  • PoolNone
  • lot featuresCleared, Other, Level
  • parkingDriveway, Three or more Spaces, On Street
  • security FeaturesKey Card Entry
  • other exterior FeaturesLandscaping

Financial

  • Sales Price$3,295,000
  • Real Estate Tax $6,724/yr

Kailua

Kailua is one of Oʻahu’s most desirable coastal communities, known for its relaxed island lifestyle, world-renowned beaches, and strong sense of community. Located on the Windward side of the island, Kailua offers a rare balance of laid-back charm and everyday convenience, with easy access to Kailua Beach, Lanikai, boutique shopping, dining, and outdoor recreation. Kailua’s real estate landscape includes luxury single-family homes, beachfront estates, and select residential enclaves, many prized for privacy, walkability, and proximity to the ocean. With its family-friendly atmosphere, natural beauty, and enduring appeal, Kailua continues to attract discerning buyers seeking an exceptional quality of life in one of Hawaiʻi’s most iconic beach towns.

Explore

Work With Jason

Whether representing buyers or sellers, Jason continues to help his clients achieve their long term real estate goals through his extensive local market knowledge and professionalism, making him a successful and trusted agent throughout the island of Oahu.