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Maui Real Estate Professionals

Maui Real Estate Agents

We love living in Maui & you will too!

Maui Hawaii, is one of the most marvelous places on earth. Tropical rain forest, lush green pastures, mountains and warm water year round. Roger Pleski offers a unique perspective to those interested in owning a piece of Maui’s oceanfront island paradise.

Roger has seen firsthand the dramatic growth and changes in Maui real estate and in Hawaii. Through his large network with Wailea Realty Corp., Roger has access to homes, land and condos that would otherwise be missed on other real estate websites. Since you’re already here, why not browse our featured Maui Condos for Sale or Click Here to Search the Maui MLS <<<.

Your Maui Real Estate Search Ends Here:

1. Thinking of Moving to Maui?

Why not! The Island of Maui is truly in a league of it’s own! Ranked the #1 Island in the world for the 16th year out of 20, according to Conde Nast readers’ poll in 2010, it also ranks as the Top Pacific Island for the 20th consecutive year, with Kauai ranking second globally and locally. The Big Island is No. 8 in the world, Oahu is No. 9, and Lanai is No .14. With those statistics, it’s easy to see why so many famous people have houses here and the locals say “Maui no ka oi,” (it’s the best!).

2. Luxury Maui Real Estate

From Oceanfront Napili luxurious homes for sale – down to the bottom of Makena. Our website features premiere Maui properties for sale in Makena, Kihei, Wailea and Napili, sorted from the most expensive to the least expensive. If you have any questions, or if you would like to see one of these luxury Maui real estate properties for sale call me, Roger Pleski at 808-344-0180.

3. Moving to Maui Checklist

Moving to Hawaii with Pets, Dogs, Cats, Kids & More. If you’re If you’re thinking of moving to Maui, you might want to take a look at our moving to Maui checklist beforehand. Deciding to move to Maui is a very big decision, the island of Maui is actually more expensive than a lot of other states around the nation. Before you pack up all of your things for the trip, you should review this checklist and make sure that you have everything in order, as this can also help you prepare for some of the things that you should expect to find once you have arrived on the island. Whether or not you know someone that lives here, you should do some research online to see what the moving to Maui reputation is. It’s a huge move so you need to be positive & prepared!

Maui is comprised of two large volcanoes divided by a flat, wide fertile valley which gives the island its nickname of the Valley Isle. Forming the east side of the island is the 10,0023-foot Mt. Haleakala, the world’s largest dormant volcano. To the west lie the older West Maui Mountains, eroded to stunning green-clad towering cliffs and valleys.

Gentle trade winds bless the island most days of the year, producing clean air and bringing regular rainfall. The summer months are mostly sunny with some clouds. The winter months bring more rain to the windward parts of the island (east and north), though the leeward parts remain mostly temperate throughout the year.

For a small Pacific island of only 734 square miles, Maui is incredibly diverse in every way. Climate zones range from tropical forest to desert. You can watch the sun rise atop a 10,000-foot mountain with a moon-like landscape, then journey through dense bamboo forests on your way to the arid leeward coastline to watch the sun set from a beautiful white sand beach lapped by the warm Pacific Ocean.

Communities run the gamut from bustling seaside Lahaina town to quiet, quaint Hana. From the funky, windsurfing mecca of Paia to the luxurious tourist destination of Wailea. From the major population and commercial center of Kahului to the upcountry bedroom community of Kula.

It is estimated that by the year 2010, 144,562 people will call the Island of Maui their home. And the population is as ethnically diverse as the communities in which it resides. Many who live here are descendents of laborers who came to work in the sugar cane and pineapple fields. Ethnic populations include native Hawaiian, Polynesian, Japanese, Chinese, Filipino, Portuguese, Caucasian, Samoan, Tongan, Latin Americans, and more.

Another population lives temporarily off-shore each year during the months of November to May. Humpback whales winter in the waters of Maui and are a fascinating spectacle to residents and visitors alike.

Each and every community on the island has its own unique flavor and most are self-contained with a variety of services to offer its residents. Though the island is small, there is definitely a place for everyone to feel at home. After just a short time you’ll understand why residents say “Maui No Ka Oi” (Maui is the Best!).


Average annual temperature: 80-90
Average annual rainfall: 18”
Elevation: Sea level to 65 feet
Population (Kihei/Wailea): 53,316
Wailea is defined by well-built, upscale homes, gated communities, manicured lawns and tree-shaded streets. Multi-million-dollar hotels sit regally on their exquisite beachfront perches and are enjoyed by thousands of visitors annually. Five golf courses are an integral part of the Wailea/Makena area. They stretch north to south with both mountain and ocean vistas. Wailea is generally acknowledged as one of the finest planned resort communities in the world. Wailea’s 1500 acres are home to some of the best hotels in the world – most notably the Four Seasons and Grand Wailea resorts – along with a great mix of single-family homes, condominiums and sporting facilities.

Because the hotels offer so many shopping opportunities to their guests, there isn’t much in the way of services in Wailea itself. The Wailea Shopping Center is being renovated into a grand space called The Shops at Wailea. Construction began in early 1999.

Moving southward, Wailea gives way to Makena, boasting more natural beauty with Makena Beaches, also known as Big and Little Beaches. As the road continues south of Makena, it winds past beachfront homes and ends at lava fields, stark remnants of Mt. Haleakala’s most recent volcanic activity.


Average annual temperature: 80-90
Average annual rainfall: 6-10”
Elevation: Sea level to 85 feet
Population (Kihei/Wailea): 53,316

Kihei is one of the fasting-growing communities on the island very due to its sunny, dry climate and beautiful beaches. This tourist mecca covers a long strip of coastline stretching five miles from North Kihei to Wailea. It has one major shopping center – Azeka Place I and II – and many smaller centers along its length. There are a number of hotels, as well as condominium complexes and residential neighborhoods throughout.

Kihei residents are served by three large chain grocery stores – the state’s largest Safeway store, Star Market and Foodland – a post office branch, all major church denominations, three schools, and a brand new community center with a fabulous, Olympic-sized swimming pool. The three major banks on Maui are represented with branches in Kihei, and there is a new library in the center of town, across the street from the movie theater complex. There are a couple of open-air markets with merchants selling local crafts, fresh produce, tropical clothing, souvenirs and a variety of other goods.

Sports enthusiasts enjoy a number of gyms, a youth center, lighted baseball diamonds and, of course, every conceivable ocean activity. The community is home to a research and technology park where a computing center is located. The computers are linked to the telescopes atop Mount Haleakala. The park is designed to attract technology and other “clean” industry to the island economy. Nearby is the Silversword golf course.

Some of Maui’s most beautiful beaches line the coast of Kihei, stretching in a nearly unbroken chain from Kihei’s neighbor community to the north, Ma‘alaea, all the way to Big Beach at Makena. The beaches and beach parks attract many thousands of visitors every year, and some of the busier beaches are attended by lifeguards.


Average annual temperature: 70
Average annual rainfall: 12-18”
Elevation: Sea level to 100 feet
Population: 1,653

The town of Paia is very small and quaint with wonderful old buildings, remnants of the time when it was the county seat. The residents comprise a very “mellow” group, consisting mainly of local Hawaiian families, “hippie” types, surfers and windsurfers. In fact, Paia is known to many as the windsurfing capital of the world. One of the best and most challenging windsurfing spots in the world is Hookipa Beach, a short drive from the town center. New subdivisions are being built, so the area is becoming more popular with families as a minor bedroom community.

There is a small post office here, a Bank of Hawai‘i branch, and, just past the main part of town, a civic center and a community center. Worshippers have their choice of several congregations, ranging from Catholic to Buddhist. The town’s buildings contain mostly small shops, restaurants – many with a “healthy” focus – antique shops and arts & craft stores. Mana Foods natural foods store is a major gathering place for many of the locals.

On the Kahului side of Paia is Baldwin Beach, a beautiful north shore beach, and the Maui Country Club with its regal old golf course. The town is almost completely surrounded by sugar cane fields and just up the hill on the road to Makawao is an operating sugar mill. Because of its position as the gateway to Hookipa Beach, the road to Hana, and Upcountry, Paia seems always to be humming with activity and host to a diverse group of residents and visitors.


Average annual temperature: 64-74
Average annual rainfall: 34”
Elevation: 1,500 to 4,000 feet
Population: 7,116

The word “Kula” means “open country” in Hawaiian and this rural community lives up to its name. It is spread out along two parallel “highways” and extends many miles. Mostly residential, there are no major shopping areas or business centers. For the residents, lack of proximity to some “downtown” services is outweighed by the peaceful beauty of the area. There are, however, some charming country shops like Morihara Store and Ching’s for groceries and Kula Hardware for garden supplies, plants and hardware, a great local-style restaurant called Café 808 and Grandma’s for fabulous coffee and pastry. The Kula Lodge has a restaurant and an art gallery as well.

Schools include the private Haleakala Waldorf School and public Kula Elementary and there are several wonderful old churches including Holy Ghost – where the Portuguese parishioners bake renowned sweet bread – a community center, a post office and new firehouse. Further up Kula Highway is the former Kula Sanitarium, now a hospital. It stands on beautiful grounds with an incredible view of the Kihei/Wailea area and the island of Kahoolawe. It also houses one of the best thrift shops on the island!

Kula is the gateway to the higher elevations of Mt. Haleakala where outdoor enthusiasts can enjoy hiking, biking, camping, horseback riding and even hang gliding. Residents and visitors alike are treated to spectacular views of the central Maui valley and the West Maui Mountains from almost every vantage point in Kula.

Kula is quiet and cool, with open spaces and beautiful views. The pineapple fields reach up the mountain to this area, where there is also an abundance of local farms growing a variety of crops. The rich soil, some of the richest in the entire state, is perfect for Protea (flowers), potatoes, the world-famous Kula onions, cabbage and many other vegetables. Island chefs depend on Kula farmers for much of their produce. Maui’s sole vineyards and winery are located at the far end of Kula at Ulupalakua. Tedeschi Vineyards produces several grape products along with its well-known pineapple wine called Maui Blanc. Ulupalakua Ranch, incidentally, covers approximately 25,000 acres from the far reaches of Kula all the way down to the ocean and is a working ranch now raising, along with sheep and cattle, such exotic livestock as elk.


Average annual temperature: 70-75
Average annual rainfall: 22”
Elevation: 1,300 feet
Pop. (Makawao/Pukalani): 16,731

Pukalani is a residential community five miles “up the mountain” from the base of Haleakala Highway. Although very close in proximity to Makawao, it receives much less rainfall because it is much more leeward than its neighbor.

The name Pukalani literally means “hole in the heavens.” The clouds that form on the mountain above and the clouds that move in from the east converge just above and below the community, leaving Pukalani sunny almost all the time and able to retain expansive views of the entire Central Valley and the West Maui Mountains.

Services for Pukalani and other upcountry residents focus around Pukalani Terrace Center, comprised of a large Foodland supermarket, hardware store, post office station, branches of two of Hawai‘i’s three major banks – Bank of Hawai‘i and American Savings – a number of restaurants, a video store, and toy store. Across the street is the new Mayor Hannibal Tavares Community Center (named for a former Mayor of Maui County), the Pukalani Aquatic Center, and playing fields, and nearby is the Pukalani Country Club with its 18-hole golf course.

Just “up the hill” from the shopping center is a second post office location and the third major bank branch – First Hawaiian Bank – in a smaller shop complex. There is an elementary school and the new King Kekaulike High School. Three church congregations worship in Pukalani.


Average annual temperature: 68
Average annual rainfall: 58”
Elevation: 1,200 to 4,000 feet
Pop. (Makawao/Pukalani): 16,731

Makawao is an old “paniolo” town that has maintained its small size, charm and accessibility. Paniolos are Hawaiian cowboys who find the mild climate and large open fields on the slopes of Mt. Haleakala perfect for cattle ranching. This area, which includes Olinda above the town center of Makawao, was originally settled by Portuguese homesteaders. Descendants of many of the original families live here to this day. Cattle and horses are still a large part of this upcountry town and surrounding area and they’re celebrated with an annual July 4th parade and the state’s largest rodeo. The mostly refurbished old buildings now house a variety of wonderful art galleries, shops and restaurants, the majority of which are within easy walking distance of each other. Makawao is also a center for the practice of alternative medicine.

Set amid green space and residential areas are the post office, library and Hongwanji Mission. On the way to Pukalani on Makwao Avenue is the Eddie Tam Memorial Center which houses a police substation and gym and overlooks a basketball court and a number of playing fields. Makawao schools include an elementary school and an intermediate school, as well as one of Hawai‘i’s most exclusive private schools, Seabury Hall. Just outside of town on the road to Paia is a Montessori school and, on a former Baldwin estate known as Kaluanui, the Hui Noeau Visual Arts center hosts art workshops and classes and houses an art gallery.

Makawao residents enjoy a semi-rural way of life. There’s plenty of open space within neighborhoods and nights are quiet and peaceful. For those who crave some night life, Casanova Restaurant right in the middle of town offers live music and dancing almost every night of the week as well as a full Italian dinner menu.

Hana District

Average annual temperature: 74
Average annual rainfall: 83”
Elevation: Sea level to 60 feet
Population: 2,027

“Remote,” “unspoiled,” and “old Hawai‘i” are terms that describe Hana. This picturesque town on the eastern tip of Maui is accessible only by a long, winding road or small airport. Many visitors and residents enjoy Waianapanapa State Park, which is steeped in legend and offers incredible views of the ocean, as well as a hike through other-worldly lava fields along oceanside cliffs. There is a campground here as well as a spectacular black sand beach which is easily accessible.

Hana town has a medical clinic, library and post office, one major bank branch (Bank of Hawai‘i), and a combined elementary, intermediate and high school. There is one hotel here, a number of bed and breakfast-style accommodations and several churches. Shopping is done at either the Hana Ranch Store or famed Hasegawa’s General Store, an old wooden building holding a surprising variety of goods.

The entire district actually stretches from the taro-growing peninsulas of Keanae and Wailua – one of only two remaining major taro-producing areas in Hawaii – all the way along the “backside” of Maui through the Kaupo Gap and up to Ulupalakua Ranch. Many of the district’s residents are Hawaiian, some families having lived in the area for generations.

There is much of old Hawaii to see in the Hana area. Hike to waterfalls, swim in the Oheo Gulch pools, or visit Piilani heiau, the largest ancient religious site in the State. Hana is also the birthplace of Queen Kaahumanu, and nearby Kipahulu is the resting place of an American legend, Charles Lindbergh. Hana plays host to thousands of visitors each year; a lucky few who love the wet tropical weather and relative seclusion make their homes there. And that’s part of what makes Hana such an unforgettable place.


Average annual temperature: 76
Average annual rainfall: 23”
Elevation: Sea level to 48 feet
Population: 21,623

A planned community constructed in the 1950s as “Dream City,” Kahului is the major population and commercial center of the island and, as such, offers a large concentration of services. With the airport and harbor nearby, Kahului is the major point of embarkation for both goods and people.

Certainly the most ambitious residential project undertaken in recent years in Kahului is Maui Lani. A development of approximately 1000 acres, a total of 3500 new homes will grace the hillsides bordering Wailuku when the project is complete. An integral part of the project is the magnificent Maui Lani Dunes golf course already receiving rave reviews from professionals and amateurs alike.

The island’s largest shopping center – Kaahumanu Center – is located in Kahului. You’ll find national chains like The Gap, Sharper Image and Sears as well as local stores like Liberty House and Tempo Music. There’s also a food court and a six-plex movie theater. There are other centers in town, too – like Maui Mall with its state-of-the-art, twelve-screen megaplex movie theater and the Kahului Shopping Center – which offer additional shopping and dining choices. The newest center, Maui Marketplace, is home to the big Mainland “box” stores like Sports Authority, Borders Books & Music and Office Max. Nearby you’ll find discount outlet Costco. Since Kahului is the island’s major commercial center, there are, of course, offices, warehouses, and factories, many located in the town’s industrial park.

Maui Community College and the recently constructed Maui Arts and Cultural Center are also in Kahului. The Center houses an art gallery and 1,200-seat auditorium as well as classrooms, meeting rooms and a grassy outdoor concert area with an area dedicated specifically to the art of Hula. The community college is constantly expanding its role as Maui’s major center of education and offers a wide variety of continuing education and non-credit courses in addition to degree-track classes. All the major banks are represented with branches. Public and private elementary, intermediate and high schools, churches of every denomination, the island’s main post office and library branch are all within close range in this well-planned community.

Maui’s major hospital – Maui Memorial Medical Center – is in Kahului and situated on the same street is the island’s main Kaiser clinic. On the other side of the highway from these facilities lies the War Memorial Complex – track and football stadium, baseball stadium, gym and Olympic-sized swimming pool. This often-used arena is also where the Maui County Fair is staged each year. Kahului residents have their choice of several other pools and gyms, too, including a YMCA. Directly across from the War Memorial Complex is the big, beautiful, new Keopuolani Park with walking paths, ball fields and other recreational facilities.

Some unique features of Kahului include a working pineapple cannery and Kanaha Pond, a wildlife sanctuary on the oceanside edge of town. Also technically in Kahului is Kanaha Beach Park, a great and convenient location for both family outings and windsurfing.

Residents of Kahului enjoy warm, sunny weather, usually accompanied by ocean breezes. They are also blessed with wonderful views of both the West Maui Mountains close by, and the grand profile of Mt. Haleakala in the eastern distance.


Average annual temperature: 70-78
Average annual rainfall: 33”
Elevation: Sea level to 500 feet
Population: 23,694

Wailuku is the Maui County seat where the civic, State and Federal buildings are located. The churches and residences generally have an older flavor and charm reminiscent of the plantation days. Many houses have been renovated and are a wonderful reminder of Hawai‘i’s past. The town sits at the entrance to beautiful Iao Valley, with a rich history and unique beauty.

Because it is the county seat, Wailuku is generally bustling in the daytime, but becomes very quiet after work hours and on weekends. Many of the residents are Hawaiian, giving the area a more “local” flavor. And speaking of flavor, there are dozens of “hole-in-the-wall” restaurants here serving great local-style ethnic food. The town is also graced with several beautiful old churches, including Wailuku Union Church, Kaahumanu Church and St. Anthony’s.

Serving the residents and business population is a library branch, American Savings, Bank of Hawai‘i and First Hawaiian bank branches, several gyms, schools and pools. Wailuku also has a medical facility and a number of doctors, dentists, attorneys, architectural firms, employment offices, courtrooms and other essential core services and businesses. The new post office is located in an area known as the Millyard with many modern low-rise office buildings and some retail stores and restaurants.

Wailuku is one of the “four waters” of Central Maui. The other adjacent areas are Waiehu, Waikapu and Waihee. They are also, for the most part, residential communities of older homes and local families. There is a public golf course in Waiehu and, just a few miles out of town are two other golf courses with views of Haleakala and the central valley. One of Maui’s most popular visitor attractions, Maui Tropical Plantation, is located in Waikapu.


Average annual temperature: 76
Average annual rainfall: 17”
Elevation: Sea level to 45 feet
Population: 16,137

The Lahaina/Kaanapali/Kapalua area is a major tourist destination and, combined with the communities of Honokowai, Kahana and Napili, make up what is commonly referred to as Maui’s “West Side.” The area has beautiful beaches, grand views of the West Maui Mountains, and an active nightlife. In fact, Halloween night in Lahaina is a world-famous event known as the Mardi Gras of the Pacific. Lahaina is the former capital of the Hawaiian Islands and was the whaling capital of the world more than a century ago. Its tourist attractions, including a replica of a whaling brig that sits in the harbor, help Lahaina to retain the feel of a whaling village.

The area has plenty of shopping opportunities, two post office branches, five churches and a number of schools. All the major Maui banks have branches here. There are two cinema centers along with the Lahaina Civic Center Convention Hall. Kaiser has a medical facility here as well. The area also boasts five golf courses and every water sport imaginable along with whale-watching during the winter months. And for those who have had their fill of the beach, they can enjoy the Olympic-sized swimming pool at the Lahaina Aquatic Center.

Kaanapali is to the west side of Maui what Wailea is to the south shore – a planned resort community with world class hotels, beautiful single-family homes and lots of condominiums. There’s an excellent shopping/dining complex – Whalers Village – within the bounds of the resort area.

Many west side residents prefer to live a bit farther away from the bustle of Lahaina town and the Kaanapali resort. Things are a bit quieter up the road in the Honokowai/Kahana/Napili area. On the way, Honokawai offers some great beach parks. There are enough services to cater to the needs of residents and guests.

Kapalua is another planned resort community which is home to the Kapalua Bay Hotel & Villas and the Ritz-Carlton Kapalua. There are several world class golf courses within the Kapalua community and the prestigious Mercedes championship is held here each year. For those in search of an outdoor respite from the busy Lahaina area, the road past Kapalua beckons, and it’s very tempting to tuck a picnic basket in the back seat and head for the open road.

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