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Wailea Makena Real Estate is our specialty. My staff and I are committed to making the buying and selling of Wailea Makena real estate on South Maui a pleasurable and rewarding experience. My website allows you to search all active Wailea Makena homes, condos, & land for sale on South Maui. It is easy to use and navigate through property searches. You can also save searches and get daily email alerts of new listings as they become available.

On the east side of Maui, located along the slopes of Haleakala, is Wailea, a beautiful place most recognized for its Grand Wailea Resort and Spa. The city's estimated population of about 6,000 residents find that the upscale and extravagant layout of the area is perfect for a living environment. Wailea residents can benefit from complimentary services provided by local resorts. In addition to this, Wailea offers the promise of an affluent community that allows residents to find pleasure in the beauty and nature of Maui from the security of a safe neighborhood that has all of the services of any top-notch town.

A considerably pleasant feature Wailea has to offer is its landscaped roadways and underground utilities. Although it was originally built to serve clients of the upper class, residents of Wailea now also enjoy the city's orderly roads, beaches, and resources. Shops in Wailea provide Maui with one of the greatest selection of shopping centers that include local stores, as well as high end stores like Gucci and Fendi. Championship golf courses, tennis courts, and other various recreational facilities are also located nearby. Aside from that, Wailea also acts as host to the annual Maui Film Festival and the Maui Writers Conference.

Many water sports and tours in Wailea due to its perfect location on the leeward side of the island. Those sports include a fleet of ships established for the purpose of hosting snorkeling charters to the offshore island of Molokini. Other activities include whale watch cruises, bike tours in Haleakala, and a historic walking tour which begins in Wailea. Wailea residents generally enjoy the expensive feel of the city, its beauty and the amenities that it comes with. In spite of its posh exterior, residents and visitors appreciate the fact that Wailea is able to retain its island charm and sense of community.

84-4903 Hawaii Belt Rd, CAPTAIN COOK
$725,000
5 Beds ⋅ 5 Baths ⋅ 734632 MLS ⋅ ['Leasehold'] Tenure
This is a leasehold property. with 17 years left on the lease. Cash purchase only. Prime 4 acre manicured gentleman's farm with a variety of fruits and exotic plants. The main house has 4 bedrooms and 3 baths. Guest house has 2 bedrooms and 1 bath. Seller is looking to retain a Life Estate in the 2 bedroom cottage at this price. If someone wants to buy the property without him then the sales price increases to $925,000. Lots of classic Hawaiian features make this home unique and one of a kind. Koa wood walls, Ohia wood posts, old brick fireplace. One of the property’s most extraordinary features is its fabulous coastline and expansive ocean views. Enjoy breathtaking views of the Pacific Ocean, beautiful coastal scenery, and magnificent sunsets. The setting offers a wonderful connection to nature, with the soothing sounds of the birds and refreshing tropical breezes. The elevated or ocean-facing portions of the property provide beautiful opportunities for outdoor entertaining, relaxing, and enjoying Hawaii’s extraordinary natural surroundings. The magnificent 3,016 -square-foot Hawaiiana home has a separate primary suite on the upper floor designed to capture the warmth, charm, and relaxed elegance of traditional Hawaiian architecture. The home features the possibility of: Spacious open-concept living and dining areas. Beautiful vaulted ceilings with exposed wood beams. Natural wood finishes and tropical architectural details. Large windows and sliding glass doors. A gourmet kitchen with newer top of the line appliances along with generous entertaining space. Spacious bedrooms and beautifully appointed updated bathrooms. An expansive covered lanai overlooking the farm and ocean. Indoor-outdoor living that embraces Hawaii’s tropical climate. The large lanai becomes an extension of the home, providing the perfect setting for morning coffee, sunset dinners, entertaining family and friends, or simply relaxing!

84-4903 Hawaii Belt Rd, CAPTAIN COOK

Listing courtesy of eXp Realty.

75-685 Mea Lanakila Pl, KAILUA KONA
$1,099,000
4 Beds ⋅ 3 Baths ⋅ 734308 MLS ⋅ ['Fee Simple'] Tenure
Tucked away on a quiet cul-de-sac near the top of a desirable Kailua-Kona neighborhood, this beautifully maintained 4-bedroom, 3-bath residence offers an ideal blend of comfort, convenience, and island living. Improvements by both previous and current owners make this two-story home fresh, inviting, and move-in ready. Flexible living space. Multi generational option? The open-concept floor plan offers spacious living areas, while the wraparound covered lanai showcases ocean views and embraces Hawaiʻi's indoor-outdoor lifestyle. Central A/C, replaced in late 2024, provides year-round comfort, while the home's favorable elevation welcomes refreshing island breezes. Energy-conscious features include 16 leased solar panels with HELCO net metering and a NEW solar water heater installed in November 2025. A hot water comfort circulation pump adds convenience, while the solar water heating system can supply hot water even during power outages. Surrounded by mature palms, fruit trees, and space to garden, this property offers a tropical setting with room to make it your own. Additional highlights include: *4 bedrooms and 3 full bathrooms PLUS family room. *Updates to both upper and lower levels *Wraparound covered lanai with ocean views *Open-concept living and newer central A/C *Solar water heater installed November 2025 *Hot water comfort circulation pump *16 leased solar panels with HELCO net metering *Attached 2-car garage with additional storage *County water and sewer connections *Underground utilities and low HOA fees *Sidewalks, curbs, and nearby county park *Quiet cul-de-sac near the top of the subdivision. Minutes from Kailua-Kona's beaches, shopping, restaurants, and schools, this home offers island living with everyday conveniences close by. Buyer benefit: A pre-listing inspection by Top Notch Home Inspections has already been completed, offering buyers added transparency and confidence.

75-685 Mea Lanakila Pl, KAILUA KONA

Listing courtesy of COMPASS.

11 Kaloli Dr, KEAAU
$299,500
734446 MLS ⋅ ['Fee Simple'] Tenure
Welcome to an extraordinary offering of two adjacent, distinct parcels totaling two full acres of beautifully landscaped and naturally wooded grounds, delivering an incredible sense of space, privacy, and island potential anchored by your very own treehouse sanctuary. The first lot has been thoughtfully cleared, ripped, graded, and finished with gravel, rich topsoil, and a lush lawn, creating a mature tropical sanctuary featuring established ornamental and fruiting trees (see list in attachments). A winding gravel driveway leads toward the rear of the property, where a cleared house pad awaits your future Hawaii dream home. From the driveway, embark along a private pathway crossing a wooden bridge over a collapsed lava tube, guiding you straight into your magical forest retreat. Elevated amidst a lush tropical canopy, the open-concept cabin captures the essence of indoor-outdoor island living, featuring high exposed-beam ceilings, an oversized ceiling fan, and durable vinyl-plank flooring throughout. Abundant natural light pours through expansive sliding glass doors, opening seamlessly onto a covered wrap-around wooden deck—the ideal spot to enjoy a morning coffee in complete peace and seclusion. The inside, boasts a cozy built-in sleeping alcove with a king-size bed, a functional kitchenette equipped with a stainless steel countertop and DC refrigerator, and comfortable living spaces. Set atop sturdy post-and-pier supports, and powered by a solar array and, equipped with Spectrum cable/wifi. Ideally located just minutes from quaint Pahoa Town with all of the amenities you may need and Hilo with airport, shopping, dining, golf, and beaches, university and more, yet seemingly a world away in a peaceful and private setting. On the east side of the Big Island in Hawaiian Paradise Park.

11 Kaloli Dr, KEAAU

Listing courtesy of Big Island Brokers.

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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.

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