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$2,475,000
5 Beds ⋅ 6 Baths ⋅ 729823 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE Status
Introducing a truly exceptional legacy property, offered for the first time in nearly a quarter century, this magnificent 1.2-acre estate captures the essence of elevated island living. Gracefully positioned above Keauhou Bay, the residence commands over 100 feet of uninterrupted ocean frontage, delivering sweeping sunset vistas that transform every evening into a private spectacle. **An Enchanting Tropical Sanctuary** Step into a lush, curated paradise where mature landscaping and vibrant tropical flora create a serene, resort-like ambiance. The grounds are adorned with 16 fruit-bearing trees—including mango and avocado, while terraced gardens, ambient lighting, and winding pathways invite quiet moments of reflection and connection with nature. **Expansive & Elegant Living Spaces** The 3,708-square-foot residence is thoughtfully designed for both refined comfort and effortless entertaining. Featuring 5 spacious bedrooms and 5.5 bathrooms, the home accommodates multi-generational living or guest hosting with ease. Recent upgrades to the gourmet kitchen and primary suite bath introduce modern sophistication, seamlessly blending with the home’s timeless open-beam architecture and authentic Hawaiian character. **Resort-Caliber Outdoor Living** Designed to rival a private retreat, the estate’s outdoor amenities are nothing short of spectacular: * Two expansive swimming pools * A built-in hot tub for ultimate relaxation * Generous lanais and covered entertaining areas * Secluded terraces showcasing mesmerizing ocean and sunset views **Exclusive Turnkey B&B Opportunity** Included with the property is a rare, county-registered and grandfathered Bed & Breakfast permit, an increasingly scarce asset in Hawaii, presenting a seamless, income-generating opportunity with an established guest base already in place.

78-6737 Walua Rd, KAILUA KONA

Listing courtesy of First Island Realty, LLC.

$2,450,000
4 Beds ⋅ 3 Baths ⋅ 731149 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE Status
Popular vacation rental in Unit 1 of Princeville. This well built, and fully renovated in 2016, this two story home has 4 bedrooms and 3 baths. Lush landscape surrounds the entire property. The rear frontage on the former golf course opens to stunning mountain views and Hanalei's famous waterfalls in the distance.

4171 Kamalani Ln, PRINCEVILLE

Listing courtesy of Brian Kennelly - Sole Proprietor.

$2,450,000
3 Beds ⋅ 3 Baths ⋅ 725638 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE UNDER CONTRACT Status
Welcome to 78-122 Holuakai, a resort zoned, short term vacation rental property in the gated neighborhood in Holua Kai at Keauhou. This stunning property is offered fully furnished, and turn-key ready. This Holua Kai home features seamless indoor/outdoor living with pocket door sliders opening to an oversized covered lanai, golf course views and peek-a-boo ocean views. Relax by the inviting heated pool with swim jets and get your swim strokes in. There is an outdoor shower with hot and cold water. Built in 2019, this home has 20 owned PV solar panels with three back-up batteries. The driveway is one of the best driveways in the subdivision and allows for plenty of parking. The home is fully fenced with brand new fencing just installed on the south side. Enjoy palm trees, a julie dwarf mango tree, on sewer, county water, and in a neighborhood with underground utilities. Inside the air conditioned home, there are resort tray ceilings, an open concept kitchen with a large dining and living room area. The primary bedroom suite, separate from the rest of the house, opens to the pool and yard. The primary bathroom has a walk-in shower with a giant soaking tub and a walk-in in closet. The other two bedrooms are found on the opposite side of the home, along with a full bathroom with a double sink and an additional half bath for guests. Currently used as a short term rental, you'll enjoy a home that's already dialed in for vacation rentals. Or enjoy this as your second home or primary residence. This 41 home gated community is surrounded by the Kona Country Club golf course. Residents and guests also enjoy the Holua Kai pool, hot tub, pavilion and overlook out to the pacific ocean right above the 3rd hole, par 3 at Kona Country Club. Convenient access to Keauhou Bay, beaches, Kona Country Club, Holua tennis and pickleball courts, Keauhou shopping center, and Ali’i Drive. Walkthrough video: https://player.vimeo.com/video/1141277689

78-122 Holuakai St, KAILUA KONA

Listing courtesy of Coldwell Banker Island Properties - Kona.

$2,450,000
4 Beds ⋅ 3 Baths ⋅ 725851 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE Status ⋅ Waipouli Vista Agricultural Condo Project BLDG.
SECLUDED, LUSH HIDEAWAY...Just over 2.5 acres of tropical serenity await. This custom-built plantation style estate features a main residence, a separate garage, and a stand-alone, legal one-bedroom rental cottage—each thoughtfully positioned within lush, mature flora and fauna that create a private, retreat-like setting. The primary residence welcomes guests with stunning rosewood hardwood floors and showcases exceptional craftsmanship throughout. Quality materials are evident from the slate entry to the travertine-tiled bath and custom finishes. The kitchen is equipped with a Wolf cooktop and oven, while additional highlights include a Whirlpool Kohler tub, charming bay windows, and Ipe-wood lanais. Both the main home and cottage benefit from solar water heating. An outdoor shower, fragrant tropical plantings, and the serene, secluded location enhance the ambiance of this unique property. Despite its privacy, the estate is conveniently located just 10–15 minutes from beaches, restaurants, grocery stores, health food options, and pharmacies, as well as close to exceptional hiking, biking, swimming, and surfing. Landscaping & Grounds: The property offers an abundant array of tropical fruit trees and botanicals, including navel orange, lemon, lime, papaya, pineapple, 11 macadamia nut trees, Samoan dwarf coconut, avocado, ginger, multiple varieties of banana, breadfruit, Surinam cherry, and tangerines. For wellness enthusiasts, the grounds also provide awapuhi ginger, noni, edible flowers, and additional culinary and medicinal plants. Flowering trees and ornamentals—including jacaranda, puakenikeni, queen crepe myrtle, coral tree, rainbow shower, and numerous orchids—allow for creating custom leis and vibrant floral arrangements. The photos are lovely, but this property truly must be experienced in person. Come see and feel the romantic elegance and natural charm of this magical tropical sanctuary. Shown by appointment

6165-A Waipouli Rd, KAPAA

Listing courtesy of Hawaii Life.

$2,445,000
3 Beds ⋅ 3 Baths ⋅ 725573 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE Status ⋅ Hale Pinao Condo BLDG.
Tucked away in lush Wainiha Valley, this private North Shore retreat offers space, flexibility, and the laid-back Kauai lifestyle just minutes from beaches, surf, hiking, and Hanalei town. Set on over half an acre, the property feels peaceful and secluded while still being close to everything that makes this part of the island so special. The home features multiple living areas, generous outdoor space, and a flexible layout ideal for guests, extended living, creative space, or simply enjoying added separation and privacy. Surrounded by tropical greenery and mountain views, this is the kind of property that invites slow mornings, outdoor living, and a true connection to nature. Whether used as a full-time residence, island getaway, or multi-generational retreat, 4558A Ananalu Road offers a rare opportunity to enjoy the beauty and lifestyle of Kauai’s North Shore in a setting that feels private, peaceful, and authentic. Information deemed reliable but not guaranteed. Buyers/agents to independently verify all material facts.

4558-A Ananalu Rd, PRINCEVILLE

Listing courtesy of Real Broker.

$2,444,000
3 Beds ⋅ 2 Baths ⋅ 723617 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE Status
Perfect 23 acre fenced HORSE property & orchard 8 mi. N. of Hilo! Discover a private 23-acre agricultural estate just 8 miles from Hilo, offering the perfect balance of privacy, productivity, and convenience. The property is zoned Dedicated Agriculture, fully fenced, and improved with established livestock infrastructure, stream access, and deep soil—making it far superior to raw land. A long, flat 1,500-ft. owned driveway leads to the solar-powered 3-bedroom, 2-bath main residence (approx. 1,310 sq. ft.) featuring Brazilian Koa hardwood floors, sweeping ocean views, Mauna Kea views, and two brand-new 23-ft. Trex decks completed in November 2024. The home is fully self-sufficient with a catchment water system and dual 3,000-gallon tanks. Surrounding the home is a productive one-acre orchard with 20+ fruit trees. Kapehu Stream borders the north side of the property, with a second spring-fed stream crossing the land. Additional improvements include a 12’ x 24’ tiny home with ocean views and mini catchment system, an unpermitted 2-bedroom, 1-bath cottage, and multiple outbuildings—offering flexible income or multi-use potential. Enjoy a cool, comfortable climate year-round and easy access to Hilo’s shopping, dining, and nearby beaches.

28-646 Kaupakuea Homestead Rd, PEPEEKEO

Listing courtesy of Jeffrey Samuels Realty.

$2,440,000
2 Beds ⋅ 2 Baths ⋅ 726565 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE Status
Extensively remodeled and turnkey, this 2-bedroom, 2-bath home offers a clean and modern retreat in the heart of Kauai's North Shore. The renovation which was just completed at the end of 2024 includes oak flooring throughout, custom oak trim, new kitchen and bathrooms, all new lighting, air conditioning throughout, new interior and exterior paint, new fencing, and a new pool heater with a saltwater filtration system, as well as numerous other upgrades. The comforts of this home extend outside with a private, fenced-in pool that is surrounded by newly installed landscaping and irrigation, as well as an outdoor dining patio that is ideal for hosting guests. Located in the VDA (Visitor Designation Area) and permitted for short-term rental use, the home offers great versatility as a vacation rental, second home, or full-time residence. With its central location in Princeville, tennis and golfing facilities are available just around the corner and you are only minutes from the 1 Hotel Hanalei Bay and its luxurious amenities. The quintessential surf town of Hanalei is just a short drive away and countless world class beaches and surf locations are accessible in any direction along the coastline.

3979 Kalakaua Pl, PRINCEVILLE

Listing courtesy of Hawaii Life.

$2,400,000
3 Beds ⋅ 3 Baths ⋅ 410090 MLS ⋅ Fee Simple Tenure ⋅ ACTIVE Status
2451 Umeke Cir has the ideal 1½-story floor plan that offers the convenience of main-floor living while providing additional space upstairs for family or guests. It is also one of the newer built homes in Hokulani. Meticulously maintained and extensively upgraded. The spacious kitchen is a chef's dream, featuring upgraded Bosch appliances, an oversized KitchenAid refrigerator, a built-in 18-bottle wine cooler, and abundant workspace for everyday living and entertaining. The adjoining great room is enhanced with built-in electronics cabinetry, surround sound, and Lutron hardwired remote-controlled shades, creating a comfortable and sophisticated living space. The main-level primary suite offers a peaceful retreat with custom closet shelving, additional bathroom storage, and a beautifully upgraded bath featuring custom cabinetry and a custom glass shower enclosure. A unique office with elegant double French doors provides the perfect work-from-home space or quiet den. Designed with efficiency in mind, the home features 32 owned solar panels, two Tesla batteries, a brand-new Lennox air conditioning system (2026), and a tankless water heater, helping to reduce utility costs while providing year-round comfort. Additional upgrades include tile flooring throughout, fresh interior paint, hardwired outdoor speakers, an oversized two-car garage with epoxy floors, built-in tool storage, custom storage closets, Garage Gator lift systems, kayak pulley storage, and even space for an additional refrigerator and freezer. The laundry room is equally well appointed with custom cabinetry and an electric washer/gas dryer setup. Step outside to the lanai, where you'll enjoy a charming ocean view, electric shades, upgraded sliding screen doors, and a propane connection ready for your grill…an inviting spot to relax and enjoy Maui's indoor-outdoor lifestyle. From the extensive custom storage to the thoughtful energy-efficient improvements and premium finishes throughout, this exceptional home is truly move-in ready and offers the perfect blend of comfort, functionality, and island living. Also listed as condo MLS #410089

2451 Umeke Cir Unit 67, Kihei

Listing courtesy of Hawaii Life (W).

$2,400,000
3 Beds ⋅ 3 Baths ⋅ 410089 MLS ⋅ Fee Simple Tenure ⋅ ACTIVE Status ⋅ Hokulani Golf Villas BLDG.
2451 Umeke Cir has the ideal 1½-story floor plan that offers the convenience of main-floor living while providing additional space upstairs for family or guests. It is also one of the newer built homes in Hokulani. Meticulously maintained and extensively upgraded. The spacious kitchen is a chef's dream, featuring upgraded Bosch appliances, an oversized KitchenAid refrigerator, a built-in 18-bottle wine cooler, and abundant workspace for everyday living and entertaining. The adjoining great room is enhanced with built-in electronics cabinetry, surround sound, and Lutron hardwired remote-controlled shades, creating a comfortable and sophisticated living space. Also Listed at Residential MLS #410090 The main-level primary suite offers a peaceful retreat with custom closet shelving, additional bathroom storage, and a beautifully upgraded bath featuring custom cabinetry and a custom glass shower enclosure. A unique office with elegant double French doors provides the perfect work-from-home space or quiet den. Designed with efficiency in mind, the home features 32 owned solar panels, two Tesla batteries, a brand-new Lennox air conditioning system (2026), and a tankless water heater, helping to reduce utility costs while providing year-round comfort. Additional upgrades include tile flooring throughout, fresh interior paint, hardwired outdoor speakers, an oversized two-car garage with epoxy floors, built-in tool storage, custom storage closets, Garage Gator lift systems, kayak pulley storage, and even space for an additional refrigerator and freezer. The laundry room is equally well appointed with custom cabinetry and an electric washer/gas dryer setup. Step outside to the lanai, where you'll enjoy a charming ocean view, electric shades, upgraded sliding screen doors, and a propane connection ready for your grill…an inviting spot to relax and enjoy Maui's indoor-outdoor lifestyle. From the extensive custom storage to the thoughtful energy-efficient improvements and premium finishes throughout, this exceptional home is truly move-in ready and offers the perfect blend of comfort, functionality, and island living

2451 Umeke Cir Unit 67, Kihei

Listing courtesy of Hawaii Life (W).

$2,400,000
4 Beds ⋅ 4 Baths ⋅ 730357 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE Status
Ideally situated in one of Princeville's most coveted locations, 5072 Kamamalu Loop offers the perfect balance of convenience and tranquility — just moments from the iconic Queen's Bath, yet nestled in a quiet, private enclave. Here, this festive, furnished vacation rental is a vibrant island style host. The residence delivers four air-conditioned bedrooms and four bathrooms across a well-conceived layout with beautiful hardwood floors upstairs and earth-toned tile below. This classic Princeville reverse floor plan features vaulted open-beam ceilings, jalousie windows, and a generous run of sliding doors that invites abundant, air, views and light into the space. The expansive living area flows seamlessly to a large lanai where you find the balmy trade winds feel like a hug from an old friend. The kitchen is a true standout — outfitted with custom cabinetry, a gas cooktop, stainless appliances, including a Sub-Zero fridge and generous quartz countertops, all finished with tile flooring. A separate dining area provides an ideal gathering space for entertaining and memorable meals. Two primary en suites — one up, one down — offer flexibility for owners and guests alike, complemented by a guest bath off the living area and a dedicated laundry space. Lava rock accents, lush tropical landscaping, and an indoor-outdoor lifestyle define the character of the home throughout. The roomy residence is designed to accommodate all types of holiday entertaining from weekend games to weekday game nights; all in convivial casual comfort. Out back, a private spa sits beneath the shade of a magnificent mango tree, creating a true island oasis. Whether your guests are seeking adventure on the North Shore or a peaceful retreat, 5072 Kamamalu Loop assuages all. Video Tour: https://tinyurl.com/5072-Kamamalu-Loop 3D Tour: https://www.zillow.com/view-3d-home/5b41560e-5f4d-4579-8187-82d745590d13?setAttribution=mls&wl=true&utm_source=dashboard

5072 Kamamalu Lp, PRINCEVILLE

Listing courtesy of COMPASS.

$2,400,000
3 Beds ⋅ 2 Baths ⋅ 731259 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE Status ⋅ Poipu Shores BLDG.
Located within Kauai's Visitor Destination Area (VDA), this beautifully renovated oceanfront 3 bedroom condo offers a rare opportunity for vacation rental use while enjoying one of the most spectacular shoreline settings on the island. This updated 3-bedroom, 2-bathroom condo is designed to maximize ocean views and cooling trade winds. The open-concept living area flows seamlessly onto the spacious oceanfront lanai through large sliding glass doors, creating the perfect setting for indoor-outdoor living...condo style. Additional features include a fully equipped kitchen, in-unit washer and dryer, owner lock-off storage, and space for beach gear and everyday living. Poipu Shores is one of Kauai's most sought-after oceanfront communities, perched along the sunny South Shore with dramatic, unobstructed coastline views. Watch whales breach in season, sea turtles glide through the surf year-round, and dolphins play offshore -- all from your private lanai. The rhythmic sound of waves crashing against the lava rock shoreline below creates a truly immersive island experience. Residents and guests enjoy access to the oceanfront pool and sundeck, situated just steps from the water's edge. The property is conveniently located near Poipu Beach and Brennecke's Beach, with easy access to swimming, snorkeling, surfing, dining, shopping, golf, and scenic coastal walking paths connecting to many of the South Shore's most popular destinations. Whether you're seeking a primary residence, second home, or investment property, this exceptional oceanfront retreat offers the opportunity to experience the very best of Kauai living. Features: • Year-round sea turtle viewing and seasonal whale watching • Spacious open-concept living area • California King primary suite with ensuite • Queen guest bedroom with lanai access • Third bedroom with two twin beds • Full-size sleeper sofa • Fully equipped kitchen • In-unit washer and dryer

1775 Pee Rd Unit 301B, KOLOA

Listing courtesy of Hawaii Life.

$2,400,000
3 Beds ⋅ 3 Baths ⋅ 730340 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE UNDER CONTRACT Status
Welcome to Nana Kai, meaning “looking toward the sea”, an exceptional Big Island community where dramatic volcanic landscapes meet the serenity of the Pacific Ocean. The “MAILE” residence on Homesite 14 showcases sweeping Pacific Ocean & Maui views and offers 2,040 square feet of thoughtfully designed single-level living. Blending Hawaiian-inspired architecture with modern comfort, this home embraces seamless indoor-outdoor living. Expansive covered lanais at the entry and rear create inviting spaces to relax, dine, and entertain year-round. The rear lanai offers a private retreat, perfect for gatherings or quiet moments in your own island sanctuary. Inside, the open floor plan flows effortlessly with three bedrooms and three luxurious baths. The primary suite is designed for privacy and comfort, featuring wood flooring, large windows, and a spa-inspired bath with dual vanities and a generous walk-in closet. The gourmet kitchen is appointed with quartz countertops and GE Café appliances, and opens to a vaulted great room filled with natural light. Expansive windows frame beautiful land and ocean views, bringing the essence of Hawaiʻi indoors. Ideally located just minutes from shopping and golf, and only 15 minutes from renowned beaches, world-class resorts, boutique shopping, and fine dining along the South Kohala Coast, Nana Kai offers both tranquility and convenience. The inaugural village will feature miles of walking, hiking, and biking trails, clubhouse amenities, and a future neighborhood commercial center, all designed to be enjoyed on foot or by bike. Offered at a special introductory price and one of a limited number of homes available at this initial release pricing, this is a rare opportunity to secure a brand-new residence at the start of this exciting new community. More than a home, it is a refined island retreat, embodying the very best of Life on the Big Island.

68-5509 Nalu Pl, WAIKOLOA

Listing courtesy of Hapuna Realty.

$2,400,000
27 Beds ⋅ 9 Baths ⋅ 728094 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE UNDER CONTRACT Status
Rare Investment Opportunity in the heart of Hilo! Nine 3BR/1BA homes on 1.65 acres. Desirable location just below Komohana St and above the police station. Sweeping views of Hilo Bay and Mauna Kea from some vantage points on the property. Two private, paved driveways lead you to each charming home nestled into this Hilo hillside.

572 Kukuau St, HILO

Listing courtesy of Hilo Realty, LLC.

$2,400,000
726730 MLS ⋅ ['Fee Simple'] Tenure ⋅ ACTIVE Status ⋅ Kalihiwai Mountains Estates BLDG.
An extraordinary 7.458-acre canvas on Kauai's prestigious North Shore—meticulously cleared and ready. Awaken to birdsong and breathtaking views of the Namolokama Mountain Range's waterfalls in the distance, with iconic Mt. Namahana commanding the horizon. A seasonal stream meanders through, enhancing privacy while contributing to the Kalihiwai Reservoir. Utilities adjacent to lot. Envision a legacy estate: a sophisticated residence, elegant guest pavilion, and curated tropical orchards—your private sanctuary in one of Hawaii's most coveted neighborhoods.

5835 Kahiliholo Rd Unit 4, PRINCEVILLE

Listing courtesy of Real Broker.

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.