Great location with amazing views. Older house and cottage on a charming dead end street on the outskirts of Makawao Town. These properties do not come on the market often and truly have that “Old Kamaaina Feeling”. Both house and cottage were remodeled in 2005 but need work to restore to original condition. This property is just waiting for the right person to come along with a vision to enjoy all it has to offer.

This property is listed by Island Sotheby's Int'l Rlty(M)

Beautiful 1.59 acre lot in Makawao with a 2 bedroom, 1 bath main home with a enclosed basement and detached ohana. The main house features charming open beam ceilings and a wide wrap around deck. The long concrete drive leads down to the main house and to the 2,400 sq. ft. barn. Private and secluded, yet close to the conveniences of town, this property also features large shade trees, a horse corral, and mountain views. Property is in distress, potential short sale opportunity.

This property is listed by Coldwell Banker Island Prop(W)

A true Maui legacy estate offering mountain and ocean views from the top of Olinda Road in cool and quiet upcountry Maui. The main home features over 1900sqft of living space and boasts a large deck for views of Maui's North Shore and the Island of Moloka'i beyond. The home is warmed by a central heating system and sunlight from the many thoughtfully placed windows. This sale includes two adjoining parcels for a total of approximately 4.173 acres of lush greenery and privacy. The original cottage could make an incredible artist studio or guest residence with some renovations. The 4.173 is the total land area of the three parcels combined. The Main Home sits on approximately 3.1acres.

This property is listed by Hawaii Life (W)

Unique custom 3 bedroom home in magical Olinda just 2.5 miles above Makawao Town. Feast your eyes on the gorgeous views from large windows throughout the house. Beautifully updated kitchen with state of the art appliances, granite counters, and hardwood floors. Downstairs there is a guest suite with a large deck. Enjoy the tranquil landscaped gardens with waterfall and 4 person heated spa. There are mature fruit and avocado trees throughout on a fully fenced 3 acre horse friendly property.

This property is listed by Coldwell Banker Island Prop(S)

Beautiful 39.76 acres of Lush Forest in Beautiful Olinda Maui. Ocean Views from almost every angle. There is county water (1 water meter) and (2) electric meters on the property .This Beautiful 39.75 acre parcel is about a 10 min drive from Makawao Town. There are 2 homes on the site, which one is a 3 bedroom 2 bath , 2637 square foot home and the 2nd home is a 3 bedroom 1 bath with 960 square feet of living space. There are 2 driveways also leading to each home. Very easy to show. Buyer must be pre approved before showing.

This property is listed by Green Realty Group

Lovely Olinda. Romantic, private hideaway with expansive views, and incredible privacy in a tranquil, natural setting. The 2 bedroom chalet & gazebo/studio are a bonus to this easily expandable custom home, privately situated on 5 acres. The home features a beautiful balance of wood & glass, embracing the views and nature. Features include open beams and stained glass accents, beautiful redwood paneling & woodwork. If you resonate with quality construction instead of quantity and appreciate wood an artistry and the glow of a fireplace...enjoy this home's elegant simplicity. Amazing sunsets and views of the Kihei coast, Lanai, Molokai and the North Shore. Terraced, established gardens, mature fruit trees and lovely, peaceful setting. Unassuming driveway off of Olinda Road leads you to the intriguing, private, jacaranda-lined lane to this properties retreat setting. The cottage and gazebo are at the top of the property so the main home's extremely private & quiet. The closest neighbors toward the view are the cattle grazing on the hundreds of acres of neighboring ranch-land. Just minutes to Seabury Hall and charming Makawao town, yet infinite in its expansiveness, sheltered setting & peacefulness. The location of these 5 acres gives one the sense of being on hundreds of acres. Broad level areas of lawn provide great open space for adventure by day, viewing the vast starry skies by night...or offer ideal positioning for a future pool or tennis court. Land offers variety of terrain and setting from exhilarating open space to intimate glades of forest; a gently sloping hill-side or the avocado tree-lined gulch; from the terraced beds of Protea and azaleas glowing in the morning sun to the sweet afternoon shade below the canopy of the pink-blooming Japanese garden tree. If you need additional room, this home was pre-designed with the option to expand by extending one wing of the structure. Built-in barbecue/sink entertainment area on multi-level lanai, which also fully embraces the amazing view.

This property is listed by Island Sotheby's Int'l Rlty(M)

Own a portion of the iconic Piiholo Ranch. This is nearly 150 acres of land, including a 1,700 sq.ft. 2 bed/2 bath home with 4,400 sq. ft. barn, riding arenas, stables and various new outbuilding. This is a true operating ranch in the heart of Piiholo. TMK's 2-2-4-12-6, 2-2-4-12-9, 2-2-4-12-31, 2-2-4-12-32, and 2-2-4-12-80 make up the aggregate 151.57 acres and are all included in this sale. This listing is to be sold in conjunction with MLS# 376129, which is TMK: 2-2-7-15-3, currently on the market for $12,500,000.

This property is listed by Island Sotheby's Int'l Rlty(W)

Experience the timeless of a Plantation Estate. Designed by renowned architect, Charles W. Dickey, the home was built in 1938 and has had only two owners. Expansive, beautifully manicured property with a lovely water lily pond, fruit trees, flowering shrubs, herb gardens, and a spectacular Banyan tree. The gourmet kitchen, designed and used by a celebrity Maui chef on a daily basis, has honed granite, Carrara marble, stainless steel and Koa counter tops, lots of cabinets for storage, Wolf and Sub-Zero appliances. This home offers a combination of historic and modern features providing a secluded haven in a rural setting located in one of the most desirable micro-climates on Maui. Just minutes from Makawao and Paia, great restaurants, shopping, Seabury Hall, Montessori School, Waldorf High School, Hui No'eau, and Hali'imaile General Store are all nearby.

This property is listed by Hawaii Life (W)

Beautifully and privately situated atop the hills of Olinda, this historic 60 acre Upcountry estate is a treasure to behold! Built in 1912, a wealth of Maui's history runs through this island property, as it was one of many homes built by H.A. and Ethel Baldwin. Surrounded by State and Haleakala Ranch lands, this legacy estate offers tremendous privacy and is the perfect setting for a peaceful Upcounty retreat. Timeless & classic, this storybook property includes a gracious 6,000 square foot home, and offers an Upcountry lodge ambiance with spacious living areas and verandas, 6 bedrooms, 3.5 baths, solid wood floors and staircase, beamed ceilings, red brick fireplace, and butler's bar, all dating to the grace & elegance of the early 1900s. Along with the main house is single level cottage and breezeway with over 1,600 square feet. The carriage driveway from the gated entrance leads to the house and cottage as well as the spacious garage and workshop. Established landscaping, including groves of Koa and many other varieties of trees & flowers surrounds the grounds. Only 15 minutes above Makawao town, 2725 Olinda Road is very much conveniently located near Upcountry's best schools, and country town with shopping and restaurants. Traditionally designed and enjoyed for many generations as a getaway, this historic Maui property has a true gracious quality that is endearing to many islanders as a classic island estate.

This property is listed by Island Sotheby's Int'l Rlty(M)

Are you looking to live in an established neighborhood in the heart of Upcountry? Located off the main road on a quiet cul-de-sac in the desirable Kealaloa neighborhood, this lovely well maintained home offers a great floor plan with flexible living areas and options for family, a caregiver, or roommates in a home priced well even for first-time buyers. Move in and enjoy the smart, simple design of the permitted addition that provides living areas on both sides of an open kitchen and includes 5 bedrooms, 2 baths, 2 living/family room areas. One bedroom currently is set-up as an office with a separate entrance, A/C, and built-in work areas; and another was designed with additional insulation as a music/reading room. There are custom wood blinds and ceiling fans throughout the home and 3 of the 5 bedrooms feature double closets with built-in shelves. With on-site parking for 4 vehicles, an owned solar water system, brand new range, irrigation system, separate ramped entrance, and built-in roofed storage behind the house, it is full of valuable "extras". The low monthly maintenance fee of $30 includes water.

This property is listed by BHGRE Valley Isle (P)