Kalaheo Hillside Homes with Fee Simple Land tenure

Welcome to Kalaheo Hillside, a stunning neighborhood nestled in the heart of Kailua, Oahu. Known for its breathtaking views and serene atmosphere, Kalaheo Hillside offers a perfect blend of natural beauty and modern living. This charming community is characterized by its lush greenery, gentle rolling hills, and a warm sense of camaraderie among residents, making it an ideal place for families, retirees, and anyone seeking a peaceful Hawaiian lifestyle.

One of the standout features of Kalaheo Hillside is the availability of homes with Fee Simple land tenure. This means homeowners have complete ownership of their property and the land it sits on, providing a sense of security and investment that is highly valued in the real estate market. With a variety of architectural styles, from contemporary designs to classic Hawaiian bungalows, there is a home to suit every taste and preference.

Living in Kalaheo Hillside means easy access to Kailua's pristine beaches, vibrant shopping districts, and a plethora of outdoor recreational activities. Residents can enjoy hiking the nearby trails, kayaking in the turquoise waters, or simply soaking up the sun on the soft sands of Kailua Beach. The community also boasts top-rated schools, parks, and local eateries, ensuring that everything you need is just a stone's throw away.

Whether you’re looking for a tranquil retreat or an active lifestyle, Kalaheo Hillside is the perfect place to call home. Experience the beauty and charm of this remarkable neighborhood, where the spirit of Aloha is felt in every corner.

Newest Kalaheo Hillside Homes with Fee Simple Land tenure

$2,149,000

4 Beds ⋅ 2 Baths ⋅ 202616975 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Fully remodeled in 2024, truly MOVE IN READY! Just a few blocks from Aikahi shopping center and Kailua beach! This 4 bedroom 2,020 SF home has a spacious great room, chef’s kitchen with gas range, pantry, indoor laundry room, & screened in bonus room, perfect for outdoor dining, or flex space. The primary suite is separated from the other 3 bedrooms with a custom closet and lg bathroom w/walk-in shower and freestanding tub. Step out to a sparkling pool, mature landscaping and multiple lanais. The vaulted breezeway leads to the additional bedrooms with a new custom Murphy bed in the middle bedroom. Spacious enough for a built in bar plus a home office. Louvered shutters throughout, solar shades in the kitchen, new fans and designer paint. A 24-panel owned photovoltaic system with battery storage on a new ’24 roof. All new windows and doors framing mountain and mature garden views. Split AC system throughout plus a gas range and two large propane tanks for a VERY energy efficient home! Plans to enclose the carport into a 2 car garage are in the permitting process! Minutes to military base, the beach, H-3, Pali and Likelike and a short stroll to great local schools.

340 Ilimano Street, Kailua

$1,650,000

3 Beds ⋅ 2 Baths ⋅ 202616142 MLS ⋅ FS - Fee Simple Tenure ⋅ 14 DOM

OPEN HOUSE SUNDAY 9/13, 1-4PM!! E komo mai to this charming home in one of Kailua's most sought after neighborhoods with less than a mile walk to beautiful Castles Beach! Located on a quiet street in the award winning Aikahi school district. Recently repainted interior & new luxury vinyl flooring in all bedrooms. This lovely home is single level with open floor plan, light and bright and plenty of privacy. Indoor/outdoor living with huge lanai area and pool perfect for social gatherings and Ohana get-togethers. Move right in or have a blank canvas ready for the most discerning buyer's upgrades, with plenty of room for expansion. Enclosed, private and large rear yard with swimming pool that is regularly serviced and cleaned. There is also a separate fenced area ideal for the pups. Close to all that Kailua has to offer. Home Sweet Home Hawaii. Love where you live!

453 Iliaina Street, Kailua

$2,185,000

4 Beds ⋅ 3 Baths ⋅ 202614657 MLS ⋅ FS - Fee Simple Tenure ⋅ 41 DOM

This is the one you have been waiting for! This home, in the desirable Kalaheo Hillside neighborhood, is strategically positioned on a large 10,000 sq. ft. lot to allow the cool ocean breezes to flow through. Large front windows overlook a welcoming tropical garden. There’s something for everyone! A large gourmet kitchen, open floor plan, sparkling tiled pool, indoor laundry, attached garage with workshop area, 4 bedrooms and three full bathrooms. Included in the 4 bedrooms is a studio with private entrance, kitchen, washer/dryer and ensuite bathroom totally separate from the rest of the house! Room for all and great for multi-generational living or long-term rental income. Ideally located with close proximity to Aikahi elementary school, Kalaheo High School, Aikahi Shopping Center, Kaneohe Marine Corp Base, H-3, Kailua Beach and mere minutes from Kailua town. Outside, a shower is conveniently located for washing off the beach sand and toys. The grounds surrounding the house are filled with beautiful Hawaiian flora, green grass lawn and mango, avacado and starfruit trees. On a quiet night you can even hear the sound of the breaking waves!

361 Iliaina Street, Kailua

$1,690,000

4 Beds ⋅ 3 Baths ⋅ 202614340 MLS ⋅ FS - Fee Simple Tenure ⋅ 48 DOM

Experience elevated island living in this fully remodeled, single-level home in the heart of Kailua. Renovated from top to bottom, this property feels virtually new and offers the perfect blend of modern design and everyday comfort. The home features a 3-bedroom, 2-bath main residence plus a connected 1-bedroom, 1-bath suite with a kitchenette, providing exceptional flexibility for extended family, guests, a home office, or potential rental income. Inside, a bright open-concept floor plan seamlessly connects the kitchen, living, and dining areas, creating an inviting space for both entertaining and daily living. The bedrooms feature premium DuChâteau hardwood flooring, adding warmth and an elegant finish throughout. A thoughtfully designed hidden laundry room enhances functionality while maintaining clean lines and a spacious feel. Outside, enjoy a fully fenced, oversized backyard—perfect for entertaining, pets, or relaxing in your own private retreat—along with a generous front yard that enhances the home's curb appeal. Turnkey and move-in ready, this exceptional property offers modern island living in one of Oahu's most desirable beach communities.

1225 Mokapu Boulevard, Kailua

$1,725,000

202610580 MLS ⋅ FS - Fee Simple Tenure ⋅ 105 DOM

Nestled within one of Kailua’s favorite neighborhoods, Kalaheo Hillside, 315 Iliaina Street is filled with potential and island charm. The property includes two separate structures --- a cute, detached cottage studio with a full bath and kitchenette, plus a classic home offering 3 bedrooms, 2 full baths, a great open floor plan, and a separate dining area with large windows looking out to the backyard. Much of the home remains in its original condition, including beautiful koa kitchen cabinet doors that could shine again with restoration. The spacious yard features a large in-ground pool and plenty of room to reimagine the outdoor spaces! Split ACs in each room. Owned PV panels with net metering. Just minutes from Aikahi Shopping Center, Aikahi Elementary School, Kailua’s beaches, shopping, dining opportunities, markets, and so much more! Also close to MCBH Kaneohe, H-3, and Likelike Highway access, this property combines location, flexibility, and opportunity in one of Kailua’s most convenient neighborhoods. (Also listed as MLS#202609716)

315 Iliaina Street, Kailua

$1,725,000

3 Beds ⋅ 3 Baths ⋅ 202609716 MLS ⋅ FS - Fee Simple Tenure ⋅ 105 DOM

Nestled within one of Kailua’s favorite neighborhoods, Kalaheo Hillside, 315 Iliaina Street is filled with potential and island charm. The property includes two separate structures --- a cute, detached cottage studio with a full bath and kitchenette, plus a classic home offering 3 bedrooms, 2 full baths, a great open floor plan, and a separate dining area with large windows looking out to the backyard. Much of the home remains in its original condition, including beautiful koa kitchen cabinet doors that could shine again with restoration. The spacious yard features a large in-ground pool and plenty of room to reimagine the outdoor spaces! Just minutes from Aikahi Shopping Center, Aikahi Elementary School, Kailua’s beaches, shopping, dining opportunities, markets, and so much more! Also close to MCBH Kaneohe, H-3, and Likelike Highway access, this property combines location, flexibility, and opportunity in one of Kailua’s most convenient neighborhoods. Split ACs in each room. PV panels on net metering.

315 Iliaina Street, Kailua

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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.