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465 Kawailoa Road Unit C, Kailua
$2,069,427
2 Beds ⋅ 3 Baths ⋅ 202606786 MLS ⋅ FS - Fee Simple Tenure ⋅ 105 DOM
Huge Price Improvement! Must see in person(photos don’t do it justice)-the WOW factor is real! Located in a highly coveted neighborhood across from Kailua Beach, this one-of-a-kind tropical retreat offers expansive indoor-outdoor living with multi-generational potential! Fully updated & impeccably maintained, it features a beautiful 2024 kitchen remodel, spacious primary suite w/stunning ensuite, 2nd garden bedroom & 2 additional stylish baths. Natural light pours through walls of windows highlighting high ceilings, custom flooring, artistic details & open-concept living, dining & kitchen spaces designed for comfort & entertaining. Step outside to professionally landscaped fully enclosed gardens w/lush greenery, flowering plants, fruit trees & songbirds-your own peaceful private oasis. Entertain at the incredible Tiki bar & BBQ/sitting areas—perfect for magical twilight evenings & unforgettable gatherings. Extras include 20 owned PV panels, hot/cold outdoor shower, solar water heater, enclosed lanai, boat parking & much more. Tucked on a private road near Kailua Town in desirable Ka’ohao School District, this home feels secluded yet just minutes from the beach & daily conveniences!

465 Kawailoa Road Unit C, Kailua
461 Kawailoa Road Unit B, Kailua
$1,515,000
3 Beds ⋅ 1 Baths ⋅ 202610888 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM
Tucked away on a private lane just one home from the Kailua Beach Park and sandy beach, 461B Kawailoa Road offers a rare opportunity to create your ideal beachside retreat. Set on a level lot, the property features an original home in average condition with a newer roof—providing a solid starting point for renovation or redevelopment. The property includes a 4618sf level lot, 856 sf 3 bed / 1 bath home with a 192 covered lanai, plus a 320sf carport. Whether you choose to update the existing residence or build a new home, the potential is exceptional. The property is situated in a desirable Kailua location, within the Ka'ohao School public charter school district, and offers convenient access to beaches, parks, hiking trails, and everyday amenities. Nearby favorites include the Mid Pacific Country Club, Buzz's Original Steak House, Kalapawai Market, Bob's Pizza, The Sunrise Shack and more. A unique opportunity to secure a prime location and bring your vision to life.

461 Kawailoa Road Unit B, Kailua
29 Alala Road, Kailua
$1,435,000
2 Beds ⋅ 2 Baths ⋅ 202519242 MLS ⋅ FS - Fee Simple Tenure ⋅ 335 DOM
Your gateway to turquoise waters, soft white sand, and the quintessential island lifestyle! Waking up to ocean breezes and a stroll across the street to world-famous Kailua Beach, this charming 2-bedroom, 2-bath cottage makes every day feel like vacation. A cozy size set on a low-maintenance parcel, it lives comfortably larger—providing all the benefits of a single-family home without the maintenance fees of a condo. Enjoy park and partial ocean views from multiple rooms, and dining al fresco on your private lanai. Wander a few minutes to Kailua or Lanikai Beach for paddleboarding, kite boarding, kayaking, snorkeling, or open-water swims. With bike paths out your front door, a restaurant a stroll away, a public charter school just up the road, and a private country club nearby, this cottage places you in the heart of Kailua’s active, outdoor lifestyle.

29 Alala Road, Kailua
445 Kawailoa Road Unit 4, Kailua
$1,425,000
3 Beds ⋅ 3 Baths ⋅ 202607704 MLS ⋅ FS - Fee Simple Tenure ⋅ 125 DOM ⋅ Windsurfer BLDG.
Experience the quintessential Kailua LIFESTYLE at The WINDSURFER, a boutique 10-unit townhome community situated directly across from Kailua Beach. LOCATION. This part of Kailua Beach has Oahu's BEST KITESURFING; it's heaven! The Windsurfers Unit #4 Is the Special Unit that sits right on the lily pond, a happy and serene spot to reflect the days activities.  This RARELY AVAILABLE residence features a freshly painted interior, loft, new washer and dryer, and updated kitchen and bathrooms from a 2018 renovation. The versatile layout can accommodate either three bedrooms, or two bedrooms with a flex space and a half bath. The large tiled private patio offers many opportunities, entertaining, dining, outdoor living room and is has a lighted walk in storage closet for bikes, tools, and equipment. 2 reserved and excellent parking spaces right outside your door and guest parking is available for your friends. Most importantly ... Yes, PET FRIENDLY! Located just steps from world-class windsurfing, Kalapawai Market, and BUZZ'S Steakhouse, this serene retreat offers a welcome escape from the bustle of Honolulu.  CALL today to learn all about the outstanding lifestyle at the Windsurfer!

445 Kawailoa Road Unit 4, Kailua

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.