Fleming Tract in Wailuku

290 Halenani Dr Wailuku HI 96793-2457

DOM 144

$1,700,000 Fleming Tract

  • 5 BEDS
  • |
  • 4.5 BATHS
  • |
  • 2764 SQFT


Charming 5-Bedroom Home with Flexible Living Options in Old Sandhills. Welcome to this beautifully updated 5-bedroom, 4.5-bathroom home situated on a generous 16,345 sq. ft. R-3 zoned lot in the desirable Old Sandhills neighborhood—offering exciting potential for accessory dwellings or additional development. Extensively renovated in 2021, this spacious home features open-concept living and dining areas perfect for entertaining. The stylish kitchen boasts granite countertops, stainless steel appliances, and modern cabinetry. Custom tile work enhances the remodeled bathrooms, and recently installed luxury vinyl plank flooring adds a fresh, contemporary feel throughout the upstairs level. Upstairs, you’ll find three bedrooms and two and a half baths, including a primary suite. Step outside to a large private deck—ideal for morning coffee, outdoor dining, or relaxing with guests. The downstairs area includes two additional bedrooms and two full bathrooms, each with its own entry—perfect for extended family, guests, or rental income opportunities. Additional upgrades include a new roof (2016), full exterior repaint (2024), upgraded 200-amp electrical service (2024), all-new above-ground plumbing, and extensive paved areas for extra parking. Easy to show with short notice. Some photos have been virtually staged to showcase the home’s potential.

290 Halenani Dr
WAILUKU        ACTIVE

Listing Courtesy of
Realty 1st Inc
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DOM 65

$1,550,000 Fleming Tract

  • 5 BEDS
  • |
  • 4 BATHS
  • |
  • 3240 SQFT


Step back in time and into a piece of Maui’s rich heritage at 231 Leinani Drive, a distinguished 5-bedroom, 4-bath estate nestled in the iconic Wailuku Sand Hills. Built in the early 20th century, this historic three-story residence stands as a rare testament to the timeless craftsmanship and enduring spirit of old Hawai‘i. Set on a spacious lot shaded by mature trees, this grand home is elevated to capture sweeping views of the Pacific Ocean and Haleakala, offering both serenity and inspiration from nearly every window. From its original hardwood floors to its high ceilings and vintage built-ins, every corner tells a story—echoing a time when homes were built with soul, intention, and lasting materials. Formerly home to one of Maui’s prominent families, this estate has hosted generations and gatherings, and is now ready for its next chapter. The layout provides flexibility, with expansive living areas, intimate nooks, and ample bedrooms that are ideal for multigenerational living, creative reimagination, or simply embracing the home’s unique mid-century charm. Historic homes like this don’t come around often—this is your chance to own a rare gem in one of Maui’s most charming and connected neighborhoods.

231 Leinani Dr
WAILUKU        PENDING - CONT. TO SHOW

Listing Courtesy of
Real Broker LLC
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DOM 169

$1,099,999 18.2% Fleming Tract

  • 6 BEDS
  • |
  • 3.5 BATHS
  • |
  • 2908 SQFT


Hidden Treasure located in the heart of Wailuku Old Sandhills. County records may not match actual floor plan. Now is your time to take advantage of this classic plantation home, main house 6 bedroom 3 bath with a renovated basement, detached 1 bedroom 1 bath cottage (tenant occupied) new flooring installed in 2020, 2 car garage with an attached bonus room setup with a full bath. Must see to appreciate the potential for investors or multi-families. Conveniently located near Schools, Hospital, Restaurants and 10 minutes away from the airport. Special features ; on demand water heater, 100 gallon propane tank, AC unit in basement, walk-in closet in large master bedroom, built-in shelving storage throughout home, convenient access to attic can be used as additional storage space, breakfast nook area with direct access to large deck, spacious kitchen with large pantry, gas oven range, dishwasher and major appliance included. Outside features ample additional parking, large backyard patio lanai for entertaining, enjoy the lush fruit trees (lemon, tangerine and banana). 2 laundry areas for your convenience and a new washing machine.

252 Halenani Dr
WAILUKU        SOLD
Close on 08/25/2021
Listing Courtesy of
Island Sotheby`s Int`l Rlty(W)
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DOM 54

$750,000 NO CHANGE Fleming Tract

  • 5 BEDS
  • |
  • 2 BATHS
  • |
  • 2064 SQFT


Step back in time and admire the historic design elements from this 1930`s home with its charming porch columns, french doors, 9 ft ceilings, built-in cabinets, glass doors and more. This is your opportunity to restore this Classic Kama`aina Home in the Old Sand Hills, a prime location in Wailuku. Possibilities are endless with this all useable R-3 zoned, 16,345 sq.ft. parcel with county water meter installed. Easy to show with less than 8 hrs notice.

290 Halenani Dr
WAILUKU        SOLD
Close on 11/17/2020
Listing Courtesy of
Emerald Club Realty, Inc.
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= property sold above asking price
= property sold below asking price
NO CHANGE = property sold at asking price

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