Maui’s Best Properties For Sale

Wailea Maui Hawaii

Choosing Your Paradise

UPDATE: Most of these properties sold.

The thing about Maui iseveryone is living their dream! Anyway you slice it, paradise can be found. On all sides of the island, magic is in abundance. There are truly no “bad” sides to the island. From the rainy eastern shores of Hana, up the tippy top of snowy (although not now, but on rare occasions) Mount Haleakala, down the  rolling hillside into Central Maui, up the steep greenery of the West Maui Mountains, and onto the rushing western break off of Olowalu, Maui is the spot! Experience the journey, it’s a ride you will never forget. There are a million Maui real estate agents, but some have their ears to the ground more than others (and more experience.)

jaws PeahiPeahi, or more affectionately known as Jaws

North Shore Real Estate

Look at it this way, the North Shore is a funky place on Maui. It tends to be less developed and less crowded with plenty of world-class beaches. It does not cater commercially to resort-oriented tourists, which is reflected in the local atmosphere. It’s home to some luxury properties, but it’s mostly for those who like to rough it once in a while.

Paia TownPaia, the heartbeat of the North Shore


Beachfront Dream Home: 63 Loio Place

Truly the most beautiful coastline and ocean view you will find on the island. This unparalleled oceanfront home listed at $6,500,000 gives you the feeling of being on your own private island when you are actually close to the heart of Paia. You will find peace and serenity from each of the master suites with private lanais and lawn area with private steps leading to the tide pools and snorkel area. The infinity pool is like an extension of the magnificent sparkling surf. The home is spacious and open with a gourmet kitchen and floor plan that provides great separation from the living and sleeping areas.


oceanfront home

This is a finely crafted home for those discerning buyers who want only the best using materials like natural Maui blue stone, solid copper roof and gutters, polished concrete and travertine floors. Experience this magical property. Property is at the road’s end with no turnaround. Not a drive by! Check out the virtual tour.


Stylish West Kuiaha Meadows: 34 Mauu Place

It is always something special when our team gets a spectacular Pauwela listings. Having spent my little kid and teenage years in Kihei, I now have transitioned to the Haiku lifestyle and I have not looked back! I absolutely love the country life, a word to the wise, do not rule out the beauty of Maui’s Northern coast.

Experience the magic of this equestrian paradise in the heart of lush Haiku for $2,050,000. These 4 incredible acres are located in West Kuiaha Meadows, a gorgeous area that combines the pastoral charm of upcountry with the sea breezes of the North Shore. The property makes the most of its location with tropical landscaping, mature fruit trees and a stone fire pit for evenings under the stars.


Along with the 4 bed, 3 bath main house, the property includes a 3 bed 2 bath cottage, so that all your guests will have room to spread out. The main house has hard-wearing yet elegant stained concrete floors throughout, 10’ ceilings, 8’ doors, custom lighting, surround sound both inside and out, and a home theater system. All counters are granite, with modern, stainless appliances. The luxurious master suite boasts a lovely marble bathroom and Jacuzzi tub with ocean views. Your horses will be as happy as you in their up-to-date 2-story barn, with sliding gates and roomy stalls.

indoors home

Enjoy a schooling session in your fenced riding arena, and then revel in the marvelous view from the 1,200 sf all-purpose room above the stable. Gently sloping pastureland adjoins the barn, framed with 100-year-old Norfolk pines. This agriculturally zoned property has two (2) 5/8″ county water meters, for additional value and potential.


Haiku Vibes: 25 Lihiwai Place

Situated on a half-acre parcel, this plantation style, single level home is located near the heart of Haiku Town for $699,000. The great room with its cathedral ceiling is composed of the living room, kitchen and dining area and extends out to the exterior lanai space. Over-sized picture windows and skylights add warmth and light to the living spaces. The master bedroom suite has three closets and sliding glass doors.


Tiled kitchen

The private backyard extends into a verdant gulch offering additional privacy, countless hues of tropical vegetation and Haleakala views. Just minutes away from many surrounding amenities, including the Cannery Shops, Haiku Elementary School and famous Ho’okipa Beach. Owner is listing agent.


East Maui Real Estate

The East side of Maui, more commonly thought of as Hana, is a very secluded side of the island which has some very obvious cons but it’s mostly about the pros. I particularly enjoy Hana because of the spotty reception, it’s the only oasis I think of when I want to unplug from my phone. There’s something refreshing about Hana, I don’t know if it’s because of some of the purest drinking water on tap (the tap water comes directly from many of the streams and waterfalls on that side of the island), or the endless amount of waterfalls.


Speacial Beachfront Property: 35 Kapohue Road

Situated on an Exceptional one acre Oceanfront parcel, the residence is valued at $1,750,000. Surrounded by palm trees and gentle breezes, this amazing island home is reminiscent of the classic Maui Beach House! Enjoy the peace and tranquility of Hana and this truly special property, as you meander down quiet Kapohue Road lined with Hawaiian rock walls and cascading trees. One will be immediately captivated by the unsurpassed ocean views beyond the rolling lawns, sounds of the surf, swaying palms and your own private lookout point!


Surrounded by large covered decks with endless views of the ocean and mountains of Hana, this island home features three bedrooms, 4 full baths, a spacious floor plan with solid wood floors, picture glass windows and vaulted ceilings ! In keeping with true island style, there are outdoor showers to rinse off from your day at the beach, and an outdoor barbecue area to enjoy family gatherings! Experience true island living!

wood floors

This is an incredible opportunity to acquire one of Maui’s most amazing and irreplaceable properties! Also available for purchase is the one acre vacant parcel directly across the lane: 38 Kapohue Road MLS #361741. Property includes a 5/8″ county water meter and underground electric and cable. Create an incredible Island Estate and family Compound with both Parcels!


Beachfront Cottage: 00 Waikoloa Road

Palekaiko Hana, is the Hawaiian retreat of noted impressionist artist Paul Arsenault. A sacred place considered the most Hawaiian. Only steps from the beach & local surf break, the place is listed at $675,000. Vistas of Hana Bay, State park & 1900’s Ka’uiki Light House. Sleep & wake to the sounds of the surf. Grab your board & go out. The house is being restored to its natural splendor. Tented in Nov. & all remedial work suggested by a licensed building inspector is being completed. 358638_2

rootsy outdoor deck

This Hawaiian bungalow consists of a lower studio apt. with its own deck & the upper floor has a 1 bedroom 1 bath, open vaulted ceiling with skylights & a private upper deck overlooking the Bay. Off the grid with Photo Voltaic system, new batteries & a new back up generator. Propane gas range & fridge, on demand hot water heater, washer & dryer. Some collectible art is included in the price, with oils, giclees & custom built-in mosaics. A beautiful giclee painted in 5 separate panels, will remain with the house, telling the story of the ancient ways of this paradise.


Central Maui Real Estate

Central Maui is an interesting part of the island, not that it stands out in any particular way because of a major flaw; it’s just that a majority of residents call it home and functions as the hub of Maui. Kahului Airport falls under central jurisdiction, as a result, it tends to back up with traffic and tourists during peak hours.

Central Maui

Cane fields and clusters

Wailuku Country Estates: 522 Maika Street

Peace and tranquility of Nature combined with Island life style, all yours for $1,830,000. The west Mountain View set as a picture frame from front yard and the majestic sun rises every morning from Ocean and Haleakala . Custom built 3 bedroom 2.5 bath with 2 extra-large rooms. Adjacent to the family room there is another large room with exquisite views, that leads out to 1000 sq. ft. covered lanai. The single level home has 3 car garages with big storage and laundry room. Features include 12 foot walls throughout the house eight foot doors, solar water heating with 26 units Photo voltaic, granite counters, gas stove, stone & carpet flooring, Jacuzzi tub, central A/C, and security system.


maui sunset home

Two homes surrounded by well-built rock walls. A swimming pool can be easily extended to backyard retaining wall. There is outside fire pit & outdoor kitchenette under covered lanai. in a rural-like setting but just minutes away from Wailuku town. You will appreciate this home very much. 3 bed/2 bath Cottage currently rented for $2300/mo. Property has 2 water meters: county & Ag.


Remodeled Plantation: 215 A Naniloa Road

Step back in time when homes had character, your piece of history for $830,000. You will see and feel what I’m talking about the minute you walk into this home. Built in 1927, Plantation Era Style home with a bonus room for extended family. The kitchen has been updated with mahogany wood floors, porcelain tile counter tops and a travertine backsplash, yet some of the old charms remains. You will enjoy listening to the built-in water features and the views from this home from your patio facing the West Maui Mountains. The manicured landscaping is the envy of all the neighbors; the fruit trees are abundant from bananas to tangerines. Original concrete tile flooring throughout.


maui home


Charming Vintage: 146 Kono Place

Impeccably assembled elements of the Old Kahului Railroad Buildings form the basis for this one of a kind architectural wonder. This house is color, art, space, history, light, humor, and style. It’s vintage yet hip – a sweet slide down the rabbit hole into an era all but wiped from the slate, yet here, lovingly restored and modernized into a home that delights and surprises with its inimitable Hawaiian soul. See better res pics at (Pictures taken before tenant vacated. House is now empty of furniture.) Gigantic wood beams and a concrete floor create a grand front room, perfect for making music, entertaining, or painting. Above this sits the airy upstairs bedroom with ocean and mountain views and its own deck.



wood beams

Travel back down the open stairs through to a sunny kitchen with Dacor appliances, high-end cabinetry. The ceiling details, and moulding anchor this part of the house firmly in the past, yet the color and modern conveniences of the remodeled kitchen place us squarely in the present. Lore has it that the adjoining parlor with its exquisite period details may have been a bar or restaurant in the Kahului Railroad Buildings – and if this is so, Hawaiian royalty may have dined here. The West Maui Mountains are framed with greenery through the rear garden, planted with low water consuming native grasses and plants. The extra covered lanai space makes this house feel expansive beyond its listed square footage. Do ask your Realtor for the pleasure of a visit to this rare piece of living history.


South Maui Real Estate

The cream of the crop, or that may be a biased answered because of all of the amazing beaches. If you want to understand why so many people find Maui so irresistible, go take a dip in a South Maui beach. White sands and clear waters, need there be a reason to say more. This side of the island is home to a lot of retirees and has a bustling night scene.


Listed by the Sayles Team: The Epitome of a Makena Estate

Special properties like 7131 Makena Road rarely become available. Unlock the door to one of Maui’s most remarkable and highly sought after estates for $9,998,000. This iconic residence is located directly across the street from the most expensive home ever to sell on the island of Maui. Very few properties in the world can match the natural beauty of this tropical getaway.


With expansive ocean vistas looking out towards the Molokini crater and the outer islands of Maui, the view is simply breathtaking. This gated estate encompasses over 2.3 acres of immaculately cared for grounds. The agricultural zoning of the property would also allow for the building of future structures. The possibilities are endless. There are over 60 fruit bearing trees on the property fully equipped for your sustainable island lifestyle.

great living room

The interior decor of the home is both comfortable and tasteful. The residence also features 2 spectacular master suites, with a total of over 5000 square feet under roof. Located within walking distance from one of the best beaches in the world. Makena, Maui, No Ka Oi.


Listed by the Sayles Team: Ho’olei Unit 39-4

Hoolei Villa 39-4 is an iconic home that is situated in the heart of the last resort-zoned development in Wailea, Hoolei at Grand Wailea Resort. The view is quite spectacular with pocketing doors that open up to the amazing blue water clear out to the island of Lanai and it can be all yours for $3,495,000. Furnished by a prestigious interior design firm, this villa is both tasteful and comfortable. Custom wall colors and lighting on dimmers combined with the palate of the Snaidero cabinetry and thick granite counter tops compliment each other perfectly. Two Sub Zero refrigerators, four freezers, Wolf stainless steel appliances and grill add to the luxury feel of this contemporary kitchen.


Hoolei sunset Maui

Thick dual-paned Fleetwood glass doors magically retract into the wall to reveal and allow access to the lanai. This indoor/outdoor living arrangement makes it perfect to enjoy your meals on the lanai with the soothing sounds of the ocean and breezes coming through the home.


West Maui Real Estate

It’s only fitting that we end with West Maui, the side of the island the sun sets on. The West side of the island is another hot bed for tourists, in particular, Front Street, Lahaina (the first established capital of Hawaii before moving to Honolulu), Kapalua, and Kaanapali. However, there is a fair amount of locals on this side of the island as it is home to the famous old Lahaina Luna High School.

black rock jumping Maui

Cliff diver off of Black Rock midday

Kapalua Gem: 305 Plantation Estates Drive

Never lived in Residence at the Plantation Estates listed for $5,750,000. Spectacular views from this contemporary residence overlooking the renowned Kapalua Plantation Course and Pailolo Channel out to the island of Molokai. A fabulous home that has 6 bedroom suites, 7 full baths and 2 guest baths, living room and great room, study, gourmet kitchen with Viking appliances, 2 laundry rooms, porte cochere, 3 car garage, luxurious pool and spa. Residence is unfurnished.


winding staircase Maui


Nicely Situated Kaanapli Home: 877 Anapuni Loop

Beautiful custom-built Island style plantation home, listed at $2,695,00o. Crafted with care and quality featuring an expansive single level living area that enjoys magnificent sweeping ocean views from every room. The wood finishes of this beautiful home provide warmth and charm not found in stucco and concrete slabs while the 27 foot African mahogany disappearing doors seamlessly expand the spacious interior and exterior Bankari iron wood deck to create a spacious floating 4,560 sq.ft. of living area.


infinity pool

The interior is beautifully finished with marble and granite countertops, cherry wood & antiqued white cabinetry, limestone & Brazilian walnut floors. Additional features include Triple Master Suites, a top of the line gourmet kitchen, spacious covered entry porch, extensive lighting systems and custom ceiling finishes. This site offers a commanding one of a kind view and location directly across from the world-class amenities of the Lanikeha clubhouse. The ocean views are assured with roof height restrictions on the adjoining home sites. There is also room to add an additional Ohana, garage, office or work space.


Hilltop Cottage: 255 B Luawai Street

Just Completed and turnkey ready to move in for $1,500,000. This .73 acre lot has the most incredible ocean views with Kahoolawe, Molokini and South shores of Maui. The contemporary finishes add a fresh and inviting feel to this 2 bedroom/ 2 bath home. With a large expanse of deck to entertain and enjoy the pool, outdoor dining and peaceful quiet of Olowalu. There is an oversized 2 car garage with a 320 sf storage/office. A private dual water system is in place, & private roads in this boutique 14 lot ag subdivision allow for privacy. Lister is one of the sellers.


Bamboo painting

Contact South Maui Real Estate Specialist


Please interview me to be your trusted Maui Real Estate and Lifestyle Advisor. I was born and raised on the island, and spend a considerable amount of time to inform my clients about the best deals currently on the market. Please do not hesitate to call me for your Maui real estate needs. I am more than happy to assist you in your home search.


Anthony Sayles R(S) 
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