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$2,500,000
4 Beds ⋅ 4 Baths ⋅ 732305 MLS ⋅ ['Fee Simple'] Tenure
Rarely does a property of this caliber become available. Designed by acclaimed Hawaiʻi architect Charles William Dickey and built in 1935 as the private estate of Laura Vestal Kennedy, exceptionally well-built and meticulously maintained 4-bedroom, 4-bath residence has remained in the same family since its completion. Offering 4,894 SF of living area, an additional 826 SF of lanais, and situated on 1.38 lushly landscaped ACRES directly across from Carlsmith Beach Park, a truly rare legacy property. Zoned RS-15, the property may offer subdivision potential (Buyer to verify with Hawaiʻi County), creating an exceptional opportunity for both homeowners & investors. Constructed by contractor Z. Kawasaki, this distinctive three-story home showcases timeless architectural character with graceful curved staircases, soaring ceilings, beautiful hardwood floors on the upper two levels, and abundant custom windows framing tropical garden, forest, and ocean views. Spacious Great Room opens to expansive lanais where cooling trade winds and ocean views create the perfect setting for entertaining or relaxing. Efficient kitchen adjoins both casual and formal dining areas. Upper level features two bedrooms connected by a Jack-and-Jill bath, with one opening directly onto the sun deck. Three of the four bedrooms include cedar-lined closets. Main level offers an additional bedroom and full bath, while the lower level provides an oversized laundry/hobby room, multiple storage rooms, and abundant space for projects or future possibilities. A detached garage complements the property, while mature tropical landscaping provides exceptional privacy in a park-like setting. Lovingly preserved by the same family since 1935, this extraordinary estate combines architectural significance, exceptional craftsmanship, generous indoor and outdoor living spaces, and an irreplaceable location near Carlsmith Beach Park, which is one of the best snorkeling beaches in East Hawaii.

1868 Kalanianaole St, HILO

Listing courtesy of Big Island Brokers.

$499,000
5 Beds ⋅ 2 Baths ⋅ 731948 MLS ⋅ ['Fee Simple'] Tenure
Opportunity Knocks! Are you going to answer? This wonderful classic Hilo home has been in this family for three generations and now is your chance to make it your own. As you can see it is well beyond its glory days but with the right amount of work and love this stunning plantation mangers home will come back to life and shine again. In addition to a large open floor plan this property offers addtional space for possible addtion of second dwelling or subdivision. Buyer should check with county planning and building departments to confirm. Home is being sold as-is. It has been vacant for a very long time, there are active termites and there are areas in the home that have extensive termite damage. Please take caution when viewing this home with your agent. The information herein while deemed reliable, may contain inaccuracies and is provided without warranty or guarantee of any kind. Tax records do not match actual bed and bath count; Buyer and Buyer's agent to do due diligence especially due to the age of the home and time period of construction. Agents and buyers are advised to independently verify any information they deem material or important to the decision to purchase the property including, but not limited to, the condition, permits and square footage of the property. Square footage is approximate and should be verified by a certified appraisal.

1735 Kinoole St, HILO

Listing courtesy of Iokua Real Estate.

$1,950,000
9 Beds ⋅ 4 Baths ⋅ 731841 MLS ⋅ ['Fee Simple'] Tenure
This towering plantation-era residence features old Hawaiʻi lodge-style architecture and an incredible location near Hilo’s most popular shoreline recreation areas. Built in 1934, the property is a highly sought-after hosted vacation rental, with an impressive track record of both income and occupancy. Positioned on a 31,500+ square foot parcel, the nine-bedroom / four-bath residence offers 6,500+ square feet of usable area and a sense of scale rarely found in Hawaiʻi. The heart of the home is an immense two-story great room, featuring soaring pitched ceilings, warm wood walls, arched openings, and a grand staircase that creates an immediate sense of arrival. Generous gathering areas, screened lanais, and flexible guest accommodations support a variety of uses, from continued hospitality operations to a one-of-a-kind private residence. Features - 9 bedrooms / 4 baths - 6,500+ sqft under roof - 31,523 sqft lot - RS-15 zoning - Plantation-era Hawaiian lodge architecture, built in 1934 - Close proximity to oceanfront parks and beach access - Soaring two-story great room with grand dual staircase - Large kitchen and generous dining area - Flexible guest accommodations across multiple levels - Screened lanais for indoor/outdoor living -Fully dedicated caretaker quarters - Tropical landscaping and private setting - High-performing, high-occupancy vacation rental Built nearly a century ago, the home's current square footage estimates do not match county tax or permit records and may contain discrepancies. Buyers and agents to perform their own due diligence. Please do not disturb occupants. Financials available upon request with signed NDA.

1896 Kalanianaole St, HILO

Listing courtesy of COMPASS.

$590,000
3 Beds ⋅ 2 Baths ⋅ 731664 MLS ⋅ ['Fee Simple'] Tenure
Welcome to this hale in Hilo, where island living meets everyday convenience. Located in an established neighborhood just minutes from downtown Hilo, schools, shopping, restaurants, parks, and beaches, this property offers a peaceful tropical retreat. Step into the backyard and discover a lush oasis with multiple fruit trees, thriving taro, and vibrant tropical landscaping that creates the feeling of being tucked away in your own private paradise. Although located in the heart of Hilo, the property offers a quiet, serene. Whether you're looking for a primary residence, a second home, or an investment opportunity, this property offers a wonderful opportunity to experience the beauty and tranquility of East Hawaiʻi.

74 Maikai St, HILO

Listing courtesy of eXp Realty.

$450,000
3 Beds ⋅ 2 Baths ⋅ 731532 MLS ⋅ ['Fee Simple'] Tenure
OPPORTUNITY KNOCKS IN HISTORIC HILO! Bring your vision to this classic 1945 plantation-era gem located at 406 Haili St, Hilo, HI 96720. Boasting 3 bedrooms, 2 bathrooms, and approximately 1,724 square feet of interior livable area on an expansive approximately 10,680 square foot lot. There are extra two rooms located off the back of the house that could be used as extra bedrooms, art studio, guest house or whatever you could use some extra space. Also ther is a large garage basement area for hobbies, crafts or a home business. This property is the ultimate canvas for investors, flippers, or savvy buyers looking to build sweat equity. Kept clean and loved over the decades, the home remains in its original vintage condition with no recent updates. It is priced accordingly and will be sold strictly AS-IS, offering a rare, affordable entry point into one of Hilo’s most prestigious and high-demand neighborhoods. The large level lot provides ample space for landscaping, gardening, or family BBQ. The premium location is its unmatched, blending historic neighborhood charm with vibrant city convenience just blocks to historic Downtown Hilo's local boutiques, cafes and grocery stores. Close to Hilo’s famous farmers market for fresh local produce, fresh seafood, and artisan crafts.

406 Haili St, HILO

Listing courtesy of Okura Realty.

$438,000
3 Beds ⋅ 1 Baths ⋅ 730736 MLS ⋅ ['Fee Simple'] Tenure
Located right in the heart of Hilo, this property at 155 W Kawailani St offers a prime opportunity in a highly desirable in-town location for real estate investors and buyers searching for Hilo fixers or value-add homes under $500,000. Zoned RS-15, this lot is well-suited for residential use and presents excellent potential for renovation, redevelopment, or a long term rental hold. With strong demand for housing in Hilo and limited inventory in this price range, this property is an ideal candidate for an investor, contractor, or buyer looking for a project with upside in East Hawaii. Home is being sold strictly as-is; seller will not make any repairs or concessions. Buyers and their agents are strongly advised to verify all information independently and conduct their own due diligence regarding zoning, permits, utilities, and any intended use of the property. If you’ve been searching for Hilo investment property, a fixer-upper in town, or a Big Island real estate opportunity with long-term hold potential, this Hilo property deserves a serious look. With some TLC, this one could become your next project or future income-producing asset.

155 Kawailani St, HILO

Listing courtesy of eXp Realty.

$800,000
4 Beds ⋅ 2 Baths ⋅ 730888 MLS ⋅ ['Fee Simple'] Tenure
Property is located in the path of growth from residential to transitional office , retail warehouse use. While still zoned residential the surrounding properties have transitioned to office -warehouse use over the recent years. The fronting street of Lanikaula has infrastructure (sewer and water) that supports this transitional use.

469 Lanikaula St Unit 1, HILO

Listing courtesy of Yamanaka Enterprises Inc.

$549,000
3 Beds ⋅ 2 Baths ⋅ 730588 MLS ⋅ ['Fee Simple'] Tenure
Welcome to Laukapu Street — ideally located in the heart of Hilo near shopping, dining, local businesses, Wailoa River State Recreation Area, the college and university, and just minutes from the airport. This spacious, beautifully landscaped property features a detached carport and endless potential. With a little love and vision, this home can truly shine and become a beautiful island retreat in a convenient Hilo location. Upstairs is filled with natural light and charming original windows that capture the character of old Hilo. The wood floors offer an opportunity to be restored to their original beauty, while the built-in shelving adds warmth and timeless island charm. Downstairs features a laundry area and expansive additional space with many possibilities for storage, hobbies, recreation, or extended living options. If you enjoy outdoor living and room to spread out, you’ll appreciate the large lot and lush surroundings this property has to offer.

524 Laukapu St, HILO

Listing courtesy of Kou Hale Realty LLC.

$1,288,888
3 Beds ⋅ 1 Baths ⋅ 729818 MLS ⋅ ['Fee Simple'] Tenure
Welcome to your very own Hawaiian oasis in the heart of Keaukaha! This rarely available gem sits on Kalanianaole Street, just moments from the East Side’s most beloved beaches, including Carl Smith Beach Park—home to gentle waves, sandy swimming spots, and frequent visits from friendly honu's. This 3-bedroom home is full of island charm, situated on a generous 20,104 sq ft lot with room to grow. With the right planning and permits, there’s potential to build up to 3 additional structures—perfect for a multi-generational compound, income-producing rentals, or your own tropical retreat. But that’s not all! Head downstairs to discover a beautifully finished lower level, completed by a previous owner with pine tongue-and-groove paneling and natural lava rock features that add warmth and character. This level includes FOUR extra rooms—ideal for home offices, workshops, hobby spaces, or extra storage—plus a utility room with a large shower and a separate toilet area. 🔹 One of only a handful of single-family homes available on Kalanianaole Ave 🔹 Potential to build 3 additional structures (verify with County) 🔹 Over 20,000 sq ft of land – plenty of space to expand or garden 🔹 Covered carport fits 2 vehicles + additional parking 🔹 Rock wall adds privacy and curb appeal 🔹 Close to beaches, parks, schools, and Hilo town 🔹 Two water heaters that are on timers Whether you’re looking for a peaceful home near the ocean, a creative live/work space, or a smart investment with future potential, 2048 Kalanianaole Street is a rare find in a prime Hilo location.

2048 Kalanianaole St, HILO

Listing courtesy of eXp Realty.

$1,200,000
2 Beds ⋅ 2 Baths ⋅ 728270 MLS ⋅ ['Fee Simple'] Tenure
Along the eastern edge of Hilo, the coastal community of Keaukaha offers a way of life that feels both connected and quietly apart. Just five to ten minutes from downtown, it provides easy access to shops, markets, and restaurants, not to mention the Hilo International airport. Keaukaha is lined with black lava rock, and tide pools. Places like Richardson Ocean Park and Carlsmith Beach Park serve as gathering spots where locals and tourists alike, swim, fish, and spend time together. The ocean here is not just scenery, but part of everyday life. This lovely home has been rebuilt almost wall by wall and captures the feel of Keaukaha. It features wood construction, jalousie windows, and a large screened in lanai wrapping two sides of the home. Trade winds move through the house, carrying the scent of salt air, while the constant sound of waves creates a natural backdrop. Inside, the style is practical and old Hawaiiana, emphasizing comfort, views, airflow and timeless elegance over luxury. This home comes fully furnished making your move to Hawaii effortless. The climate is warm, humid, and frequently rainy, feeding dense greenery and creating a landscape that feels alive. This extensively landscaped property features a variety of plantings, including Coconut palms, Betel Nut palm, Cooks Pine, Surinam Cherry Tree, Macarthur Palms, Kau Orange, Acacia, Plumeria, edible dwarf banana, Papaya, Hapuu ferns, gardenia, hibiscus, anthuriums, bromeliads, and monstera among others. Across the road, the ocean is ever-present—waves breaking on lava rock, people fishing or talking story, and occasional whales and spinner dolphins visible from shore during season. Living here is simple and grounded, defined less by amenities and more by connection—to ocean, community, and in many ways, a return to something simpler and more enduring, where the day might begin with a glance at the ocean and unfold according to the quiet guidance of the land and sea.

2070 Kalanianaole St, HILO

Listing courtesy of Aloha Sotheby's Intl Realty - Hawai'i.

$349,000
3 Beds ⋅ 2 Baths ⋅ 729183 MLS ⋅ ['Fee Simple'] Tenure
If you've been looking for a project with character, this 2-story fixer-upper in Kaumana might be just the one. Downstairs features a spacious living room, kitchen and full bath, while upstairs offers three bedrooms and a half bath. The laundry room is conveniently located in the carport. This property is ideal for buyers with vision, contractors, investors or anyone ready to bring new life to a vintage home.

2131 Kaumana Dr, HILO

Listing courtesy of Hawaii Life.

$379,500
3 Beds ⋅ 1 Baths ⋅ 728329 MLS ⋅ ['Fee Simple'] Tenure
Classic Hawaiian home built in the 1940's. High ceilings with it's original windows. 3 bedrooms and 1 bath with approx. 1,769 sq. ft. of living area. Great location only a short distance from downtown Hilo. In need of some TLC but huge upside potential with the RM-1 zoning. Lower level could possibly add more bedrooms and baths.

334 Lehua St, HILO

Listing courtesy of Century 21 Homefinders of Hawaii.

$790,000
4 Beds ⋅ 4 Baths ⋅ 727032 MLS ⋅ ['Fee Simple'] Tenure
Opportunity awaits! Two homes on larger lot in Waiakea Houselots. Both homes need some TLC, but are very livable. Live in one, rent the other or rent both. Opportunities like this rarely come up in this area. FRONT HOUSE: Fumigated 1/24/2026 Charming "old-style" touches with many built-ins: kitchen breakfast nook, original kitchen sink, dining room "hutch" (with storage drawers and shelves), lanai with generous counter/cabinets for your get-togethers. There is a generous sized storage/workshop room in the carport as well as a half bath. A separate shower is located in the utility room which is off of the carport and enclosed as part of the entry into the home, making doing laundry private and secure. BACK HOUSE: Fumigated 2/8/2024 Your basic, simple home needing some upgrades, but a little TLC will bring it to life. No appliances included with this home.

568 Kalanikoa St Unit 2, HILO

Listing courtesy of Savio Realty Ltd. - Hilo Office.

$595,000
4 Beds ⋅ 4 Baths ⋅ 720363 MLS ⋅ ['Fee Simple'] Tenure
New roof replacement and front lanai floor newly updated and painted with both front and back railings update complete. Recent electrical updates are complete and scheduling plumbing updates. This Classic style home is in a great location in the heart of Hilo town walking distance to the town's famous farmer's market and recreation areas of Lincoln park, tennis courts, Mo'oheau park and Bayfront. The Central fire station is just a block away along with restaurants, grocery stores, gas stations, and medical, bank, office, and professional services buildings. The home features 3 bedrooms upstairs each with their own private bathroom with a large front lanai entrance with beautiful ocean views of Hilo's famous Bayfront. The upstairs front door enters you into a quaint front living room with the kitchen at the end of the hallway with its own private back lanai. The upstairs unit has 9 foot ceilings and hardwood floors with the old vintage design of yesteryear. The downstairs studio is large and spacious and has a unique and spacious bathroom with tile floors. Upstairs 3/3 and back downstairs studio units previously rented long term ($2,500 plus utilities and $850 a month respectively) and possible bottom front unit available (currently an office with its own bathroom with shower) for new owner or to rent out as well.

301 Ponahawai St, HILO

Listing courtesy of COMPASS.

$399,000
3 Beds ⋅ 1 Baths ⋅ 725022 MLS ⋅ ['Fee Simple'] Tenure
BACK UP OFFERS ACCEPTED! Tucked away on a large, quiet flag lot, this vintage Hilo residence, built in the 1920s, offers classic island charm and plenty of potential. Situated on a 16,912 sq. ft. lot, just minutes from UH Hilo, schools, shops, cafés, and historic Bayfront, this location blends privacy with convenience. With RS-10 zoning and the new Bill 123, buyers are encouraged to investigate the possibility of adding an Accessory Dwelling Unit (ADU) or expanding the existing structure. Buyer to confirm zoning, setbacks, and utility/infrastructure eligibility with the County. A rare opportunity to own a piece of old Hilo with room to grow — ideal for those looking for rental income, customize, renovate, or create multi-unit living in one of the area’s most desirable neighborhoods. The long-term tenant is reliable, treats the home with care, and would like to stay on! Please do not drive by. All showings to be accompanied by a REALTOR®.

2669 Kilauea Ave, HILO

Listing courtesy of Coldwell Banker Island Properties - Hilo.

$290,030
5 Beds ⋅ 2 Baths ⋅ 723970 MLS ⋅ ['Fee Simple'] Tenure
Nice opportunity for a rehab property in Hilo town. The property was renovated before the fire damage. Fire and water damaged areas were cleaned out. The house is within walking distance to Waiakeawaena elementary school, Andrew's gym, and is located conveniently near shopping, banking, restaurant, etc. County permitted square footage is 1556. Three bedrooms with one bath upstairs and three bedrooms with one bathroom downstairs. Ground termite treatment completed in 2022. Roofing and cement siding conditions are great. Fruit producing mango and avocado trees on site. The lot is 15,000 sf with plenty of parking spaces. Located on a cul-de-sac so the property is limited to through traffic. Buyer and Buyer's agent to their own due diligence. NO CONTINGENCIS-AS-IS please add addendum. Please do a drive-by and look in windows before scheduling an appointment to view inside. The house is boarded up and easily viewed from the outside. Fire and Water damage.

89-A Kawailani St, HILO

Listing courtesy of Big Island Properties.