Kalaheo Hillside Homes with Garden View

Welcome to Kalaheo Hillside, a hidden gem nestled in the picturesque town of Kailua on the beautiful island of Oahu, Hawaii. This charming neighborhood is renowned for its stunning natural beauty, offering residents a serene lifestyle surrounded by lush greenery and breathtaking mountain views. With its warm, tropical climate and gentle trade winds, Kalaheo Hillside is the perfect place to call home.

One of the standout features of this enchanting community is the abundance of homes with captivating garden views. Imagine waking up each morning to the soothing sights and sounds of nature, with vibrant flowers and lush foliage just outside your window. Many properties in Kalaheo Hillside boast spacious yards, perfect for gardening enthusiasts or families looking to enjoy outdoor activities. The meticulously landscaped gardens create a tranquil oasis that enhances the overall ambiance of the neighborhood.

Kalaheo Hillside is not only about beautiful homes; it also offers a strong sense of community. Residents enjoy easy access to local parks, hiking trails, and pristine beaches, making it an ideal location for outdoor enthusiasts. The vibrant Kailua town center, with its boutique shops, delightful cafes, and farmer's markets, is just a short drive away, providing a perfect blend of convenience and charm.

Whether you’re seeking a peaceful retreat or an active lifestyle, Kalaheo Hillside offers the best of both worlds. Embrace the enchanting gardens, welcoming community, and breathtaking surroundings that make this neighborhood a truly special place to live. Discover your dream home in Kalaheo Hillside today!

Newest Kalaheo Hillside Homes with Garden View

$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

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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.