Oahumilitaryrealestate.com
  • Home
  • Advanced Search
  • VA Loan Resources
  • PCS Resources
  • About Us
  • Blog
  • Contact Us
Login
(808) 554-9667

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Search Kalaheo Hillside Homes

TO
Advanced Search

Address Search

Newest Kalaheo Hillside Homes For Sale

1225 Mokapu Boulevard, Kailua image
1225 Mokapu Boulevard, Kailua $1,690,000

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 o...

  • 4 Beds
  • 3 Baths
  • 202614340 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 2 DOM
923 Mokapu Boulevard, Kailua image
923 Mokapu Boulevard, Kailua $1,590,000

Welcome home to this spacious three-bedroom, two-bathroom residence in the highly sought-after Kalaheo Hillside. Freshly painted along with other upgrades throughout, thi...

  • 3 Beds
  • 2 Baths
  • 202614057 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 6 DOM
445 Iliwahi Loop, Kailua image
445 Iliwahi Loop, Kailua $2,300,000 ▲

Tucked onto one of Kalaheo Hillside's most sought-after streets, 445 Iliwahi Loop is a fully reimagined 4-bed, 3-bath retreat blending timeless island architecture with a...

  • 4 Beds
  • 3 Baths
  • 202611972 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 34 DOM
315 Iliaina Street, Kailua image
315 Iliaina Street, Kailua $1,875,000

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 ...

  • 202610580 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 59 DOM
315 Iliaina Street, Kailua image
315 Iliaina Street, Kailua $1,875,000

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 ...

  • 3 Beds
  • 3 Baths
  • 202609716 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 59 DOM
1110 Ilikala Place, Kailua image
1110 Ilikala Place, Kailua $3,880,000 ▼

Your dream waterfront Kailua residence. This hidden jewel fronting Kawainui Canal with access to the ocean offers an exceptional blend of contemporary design and Kama‘ain...

  • 3 Beds
  • 3 Baths
  • 202605289 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 131 DOM

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.

Looking to buy a Home in Kalaheo Hillside?

Browse current Homes For Sale In Kalaheo Hillside, Kailua. Can't find a home that fits your needs? Try our Advanced Kailua MLS search. You can easily filter properties by location, price, amenities, and more to find exactly what you're looking for.

Your VA Loan Benefits

Use your VA Loan Benefits

Search All Oahu Real Estate

Use our full MLS search to access all Oahu listings

Your Oahu Home Value

Our expert Oahu Realtors know your home's value like no one else

Homes in Kalaheo Hillside were built over the last six decades boasting views of the waterfront of elevated mountain views. Homes dating back to the 50s and 60s are primarily constructed ranch-style homes that were the first established community in Kalaheo Hillside. Residents of the community love the homes' heritage, but many have decided some TLC was required to keep the homes modern and cozy. 

 

Despite being set back from the coastline, some homes on the Kailua Town side of Mokapu Blvd situate right along the Oneawa Channel on its way to the Pacific, bringing a tropical canal scene right to your backyard. It's a truly unique sight, and sometimes you can even spot kayakers slowly going by, adding to the serene setting.

 

The north side of Mokapu Blvd is where the area acquires its name, the houses getting logically higher up the slope. Some toward the top can see out to the sea, views that can cause much jealousy when visitors stop by. All the lots give you suitable sizes to work with, spanning from 8,000 to 12,000 square feet. Space that gives you room for renovations and add-ons if desired. Or retain the beauty of open space around your abode.

 

Kalaheo Hillside's homes for sale have lately been priced around $800K to $1.2M, which is not unusual for this side of Kailua. The alluring appeal has developed for those looking to be away from guests showing up every day on tour buses and in rental vehicles. Protected from the traveler traffic of Kailua Town, the Kalaheo Hillside neighborhood gives a peaceful corner where residents can really live at the Hawaii pace.

Living In Kalaheo Hillside, Kailua

 

There are no towers, no rambling retreats, or no monster shopping centers. All things considered, you'll discover delicious cafés, warm overnight boarding houses, family-run eateries, and shops where the proprietors will welcome you at the entryway. Kalaheo Hillside neighborhood offers some of the best amenities, attractions, and activities the island has to bring to the table. 

 

The best thing about living in Hawaii is the white sandy beaches, and the Kalaheo Hillside neighborhood in Kailua hosts some of the best. Kailua beaches are iconic and often the sole reason people venture to this part of the island. Here you can enjoy surfing, offshore islets, or lounging at beaches Kalama, Popoia Island, and magical Lanikai Beach. 

 

Discover new neighborhood produce, blossoms, blistering food, expressions and specialties, unrecorded music, and a smooth local area scene at the Kailua Town Farmers Market on Sunday mornings. Go right on time to get a prime parking spot and the best choice of fresh produce. Take a load off in the outside bistro region to devour new organic products, heated merchandise, privately developed espresso, and plate snacks while paying attention to love music. 

 

Lastly, walk on over to the Global Village, one of Kailua's original boutiques, offering an eclectic collection of high-quality, eco-conscious, and unique products from all over Hawaii and worldwide! Each item was specialty handpicked by owners, and local favorites include beach glass jewelry, whimsical artwork, and extensive surfing and beach towels by vendors Nick Kuchar and Christie Shinn, Maona Sunny Weeks, and Girl Loves Sea. 

 

View All Homes For Sale in Kailua >>>

Like or Share

Kailua Home Types

  • 1 Story Homes
  • 2 Story Homes
  • 3 Bedroom Homes
  • 4 Bedroom Homes
  • 5 Bedroom Homes
  • Acreage
  • Condos
  • Homes With Land
  • Luxury Homes
  • Mountain View Homes
  • New Homes
  • Single Detached Homes
  • Single-Family Homes
  • Waterfront Homes

Kailua Homes For Sale By Price

  • $100,000 - $200,000
  • $200,000 - $300,000
  • $300,000 - $400,000
  • $400,000 - $500,000
  • $500,000 - $600,000
  • $600,000 - $700,000
  • $700,000 - $800,000
  • $800,000 - $900,000
  • $900,000 - $1,000,000
  • Over $1,000,000

Kailua Neighborhoods

  • Aikahi Park
  • Kalama Tract
  • Kalaheo Hillside
  • Kaimalino
  • Kailua Estates
  • Kailua Bluffs
  • Kailua Town
  • Enchanted Lake
  • Coconut Grove
  • Bluestone
  • Beachside Kailua
  • Kawailoa Kailua
  • Keolu Hills
  • Koolaupoko
  • Kukilakila
  • Kuulei Tract
  • Lanikai
  • Maunawili
  • Olomana
  • Zip code: 96734

Search Popular Areas

  • Ewa Beach
  • Kapolei
  • Aiea & Pearl City
  • Mililani
  • Kakaako
  • Kailua
  • Kaneohe
  • Haleiwa
  • Waianae
  • Home
  • Selling
  • Buying
  • VA Home Loans
  • About Us
  • Contact Us
Create an Account

Create an Account 🏡

All access to the newest listings to hit the market, 100% free. We are always here to help in case you have questions!

  • See local listings faster than any real estate website
  • Access to a local agent that will help answer any of your questions
  • Get help buying and selling with us
  • And of course, our home search service is always 100% free!

Hello, 👋

Welcome back. We have new listings for you. Remember like always, we are always here to help. Happy house hunting!

My Favorites My Saved SearchesMessage my agent
Buy

Buy

Create a bullet proof buying plan by working with the best agents in the area. From planning, pre-approvals, tours, to getting your keys.

Sell

Sell

Get your home sold for the most money, in the least amount of time. It is never too early to devise a gameplan.

Create an Account

Home Estimate

See what your property is currently worth within seconds. Just enter your address.

compass logo
Sitemap
  • Home
  • About us
  • VA Loan Resources
  • PCS Resources
  • Home Search
  • Let's Connect
Contact

Get to Know Me

(808) 554-9667

Address

4211 Waialae Ave. Suite H-8

Honolulu, HI 96816

Kahala Mall



Elizabeth La Riva is a real estate team affiliated with Compass. Compass is a licensed real estate broker with a principal office in Oahu, Hawaii, and abides by all applicable equal housing opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to accuracy of any description. All measurements and square footages are approximate. This is not intended to solicit property already listed. Nothing herein shall be construed as legal, accounting or other professional advice outside the realm of real estate brokerage.

REALTOR, ABR, e-Pro, MRP, CRS

Website designed and developed by Vanity Geeks.
  • l
  • l
  • l
  • l

© Copyright 2022 | Privacy Policy

  • Map Search
  • Advanced Search
IDX Real Estate Websites by
, an FNF RE Tech Company • Accessibility • Terms • Privacy