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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!

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

$1,435,000

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.

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

$2,069,427

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!

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

$1,515,000

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.

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

$1,399,000

Live steps from world-famous Kailua Beach in this rarely available 2-bedroom, 3-bath residence at The Windsurfer. Located directly across from soft white sand and turquoise waters, this home offers a serene retreat just minutes from Kailua Town and away from the hustle and bustle of Honolulu. Inside, you’ll find an inviting open kitchen with granite countertops, hardwood cabinetry, and a newly installed split A/C system throughout. The flexible split level layout features two bedrooms—each with its own full bath—plus a third full guest bath on the main level. A bonus loft adds even more versatility for office, or additional sleeping quarters. Your fenced front courtyard allows space for outdoor furniture and potted plants with a large closet where you can store gardening tools or recreational equipment. Relax on the spacious back lanai or take a short stroll to Kailua Beach Park, Lanikai Beach, Buzz’s Steakhouse, or Kalapawai Market. The Windsurfer is an intimate, boutique 10-unit community perfectly positioned for beach lovers and outdoor enthusiasts, with paddling, hiking, and windsurfing all close by. Experience the best of Kailua living—your own piece of paradise awaits.

2 Beds ⋅ 3 Baths ⋅ 202525037 MLS ⋅ FS - Fee Simple Tenure ⋅ 123 DOM ⋅ Windsurfer BLDG.

Live steps from world-famous Kailua Beach in this rarely available 2-bedroom, 3-bath residence at The Windsurfer. Located directly across from soft white sand and turquoise waters, this home offers a serene retreat just minutes from Kailua Town and away from the hustle and bustle of Honolulu. Inside, you’ll find an inviting open kitchen with granite countertops, hardwood cabinetry, and a newly installed split A/C system throughout. The flexible split level layout features two bedrooms—each with its own full bath—plus a third full guest bath on the main level. A bonus loft adds even more versatility for office, or additional sleeping quarters. Your fenced front courtyard allows space for outdoor furniture and potted plants with a large closet where you can store gardening tools or recreational equipment. Relax on the spacious back lanai or take a short stroll to Kailua Beach Park, Lanikai Beach, Buzz’s Steakhouse, or Kalapawai Market. The Windsurfer is an intimate, boutique 10-unit community perfectly positioned for beach lovers and outdoor enthusiasts, with paddling, hiking, and windsurfing all close by. Experience the best of Kailua living—your own piece of paradise awaits.

445 Kawailoa Road Unit 8, Kailua

$1,350,000

The Windsurfer at Kalilua Beach Park is one of the more exclusive locations in Kailua, as it is across the street from the Kailua Beach Park. This location affords you walks on the beach to watch the sunrise behind the Mokulua Islands, without getting in a car or looking for parking. With the extra guest parking spaces, you will love inviting your friends to your house to enjoy the beach! Walk or ride your bike to the Kalapawai Market (est 1935) or to Island Snow (great shave ice!), or to the kayak rental store. Walk to Buzzes Restaurant in a few minutes. The bike path across the street takes you Lanikai, for a fun bike ride or walk. Life at the Windsurfer allows you to fully enjoy a relaxed Hawaii lifestyle. The highly-rated Lanikai Charter School is around the corner from the Windsurfer

2 Beds ⋅ 3 Baths ⋅ 202524947 MLS ⋅ FS - Fee Simple Tenure ⋅ 36 DOM ⋅ Windsurfer BLDG.

The Windsurfer at Kalilua Beach Park is one of the more exclusive locations in Kailua, as it is across the street from the Kailua Beach Park. This location affords you walks on the beach to watch the sunrise behind the Mokulua Islands, without getting in a car or looking for parking. With the extra guest parking spaces, you will love inviting your friends to your house to enjoy the beach! Walk or ride your bike to the Kalapawai Market (est 1935) or to Island Snow (great shave ice!), or to the kayak rental store. Walk to Buzzes Restaurant in a few minutes. The bike path across the street takes you Lanikai, for a fun bike ride or walk. Life at the Windsurfer allows you to fully enjoy a relaxed Hawaii lifestyle. The highly-rated Lanikai Charter School is around the corner from the Windsurfer

445 Kawailoa Road Unit 5, Kailua

$2,945,000

Steps from Kailua Beach, this craftsman style beach house has a separate duplex with strong rental income potential. Live in the vaulted ceiling, dutch door, gorgeous 1 bedroom 1 bath home and rent out the two 3 bed 2 bath units! One more bonus is the converted garage on the cottage which has been modified into a cute 1 bed 1 bath space. This self-contained space offers additional flexibility, whether you wish to host guests, create a private office, or rent it out for additional income. With separate lanai spaces for all 4 living areas, there is privacy for each one. If you would like your own beautiful beach house to call home and enjoy long term income from the other areas, this is what you have been waiting for. The location is unbeatable—just steps from Kailua Beach, where you can enjoy morning sunrises, pristine waters, wind surfing, canoe club, volleyball and year-round activities. In addition, you’re close to local favorites such as Buzz’s Steakhouse, Kalapawai Market, Bob's Pizza and more. Whether you plan to live in the cottage and rent out the duplex or make the entire property a part of your investment portfolio, this Kailua gem offers endless possibilities.

8 Beds ⋅ 6 Baths ⋅ 202519459 MLS ⋅ FS - Fee Simple Tenure ⋅ 93 DOM

Steps from Kailua Beach, this craftsman style beach house has a separate duplex with strong rental income potential. Live in the vaulted ceiling, dutch door, gorgeous 1 bedroom 1 bath home and rent out the two 3 bed 2 bath units! One more bonus is the converted garage on the cottage which has been modified into a cute 1 bed 1 bath space. This self-contained space offers additional flexibility, whether you wish to host guests, create a private office, or rent it out for additional income. With separate lanai spaces for all 4 living areas, there is privacy for each one. If you would like your own beautiful beach house to call home and enjoy long term income from the other areas, this is what you have been waiting for. The location is unbeatable—just steps from Kailua Beach, where you can enjoy morning sunrises, pristine waters, wind surfing, canoe club, volleyball and year-round activities. In addition, you’re close to local favorites such as Buzz’s Steakhouse, Kalapawai Market, Bob's Pizza and more. Whether you plan to live in the cottage and rent out the duplex or make the entire property a part of your investment portfolio, this Kailua gem offers endless possibilities.

507 Kawailoa Road Unit B, Kailua

$1,861,020

Welcome to 368 S Kalaheo Ave—a rare chance to own a true piece of paradise, literally just steps from world-renowned Kailua Beach. The thoughtfully designed floor plan features 3 bedrooms and a full bath on the main level, while the expansive second-story addition transforms the home into a private retreat. Upstairs, you'll find a luxurious primary suite with a spa-inspired en-suite bathroom, a walk-in closet room, a dedicated study/office, and a private balcony overlooking the canal with ocean views—perfect for morning coffee or sunset relaxation. Significant upgrades include 24 solar panels paired with 2 Tesla Powerwall batteries, ensuring energy efficiency and peace of mind. Whether you’re entertaining guests at sunset or enjoying a quiet evening under the stars, this home offers an unparalleled lifestyle of ease, elegance, and adventure. Nestled along one of Kailua’s most desirable avenues, you’re just moments away from boutique shops, dining, and a vibrant local community—all while embracing the serenity of beachside living. *Sellers are offering VA assumable loan @ 2.25%* Check out this exceptional home minutes from Kailua Beach!

4 Beds ⋅ 2 Baths ⋅ 202516944 MLS ⋅ FS - Fee Simple Tenure ⋅ 85 DOM

Welcome to 368 S Kalaheo Ave—a rare chance to own a true piece of paradise, literally just steps from world-renowned Kailua Beach. The thoughtfully designed floor plan features 3 bedrooms and a full bath on the main level, while the expansive second-story addition transforms the home into a private retreat. Upstairs, you'll find a luxurious primary suite with a spa-inspired en-suite bathroom, a walk-in closet room, a dedicated study/office, and a private balcony overlooking the canal with ocean views—perfect for morning coffee or sunset relaxation. Significant upgrades include 24 solar panels paired with 2 Tesla Powerwall batteries, ensuring energy efficiency and peace of mind. Whether you’re entertaining guests at sunset or enjoying a quiet evening under the stars, this home offers an unparalleled lifestyle of ease, elegance, and adventure. Nestled along one of Kailua’s most desirable avenues, you’re just moments away from boutique shops, dining, and a vibrant local community—all while embracing the serenity of beachside living. *Sellers are offering VA assumable loan @ 2.25%* Check out this exceptional home minutes from Kailua Beach!

368 S Kalaheo Avenue, Kailua