Up Country Real Estate Search

Up Country Homes with a Pool for Sale

Our website features the best real estate search for homes with a pool properties available in Up Country and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Up Country Homes with a Pool for Sale

3260 Kihapai Pl, Makawao
$1,449,000
3 Beds ⋅ 3 Baths ⋅ 411172 MLS ⋅ ACTIVE Status
This is it! A super convenient location, a house and ohana, heated swimming pool and best of all… The seller is offering a 4.25% Assumable VA loan…and yes, non-veterans are eligible. This property has been well cared for and is ready for a buyer that wants a turnkey move-in experience. With a 2 to 3 minute drive to Pukalani Terrace and Pukalani Superette, and approximately a 15 minute drive to Kahului makes this property ideally located. The main house features many upgrades including, but not limited to, a 19-panel PV system with Enphase battery back-up, a full kitchen remodel, new flooring throughout, new window coverings, the interior walls are newly plastered, a tub to shower conversion in the main bath, and a beautifully retiled pool with heating system installed in 2026. The back deck overlooks the heated pool and is perfect for outdoor entertaining and year around swimming. The backyard is fully fenced for privacy and security. The 2nd home features a 19 panel PV system, solar water, newer appliances, new kitchen counter and large pantry, and easy access to a spacious back yard, with a covered lanai and gazebo for outdoor gatherings.

3260 Kihapai Pl, Makawao

Listing courtesy of Welcome Hawaii Properties.

1102 Mailuna Pl, Makawao
$1,475,000
3 Beds ⋅ 3 Baths ⋅ 410602 MLS ⋅ ACTIVE Status
Tucked privately at the top of a cul-de-sac, this beautifully appointed 3-bedroom, 3-bath home plus office is a Makawao residence that offers a rare combination of thoughtful design, lush surroundings, private pool, intimate outdoor spaces, and an exceptionally flexible floor plan. The home feels both gracious and wonderfully easy to live in, with a sense of privacy and tranquillity that is increasingly difficult to find. Upstairs, an inviting living room is warmed by a cozy gas fireplace, while expansive windows draw in abundant natural light and frame the verdant surroundings. The kitchen and living spaces open naturally toward the home's vine-draped lanai on the lee side- the Owner's favorite place to gather, dine, and enjoy the sweet views toward Makawao sunsets. The spacious primary suite offers a private retreat, complete with built-in bookshelves and a serene sense of separation from the rest of the home. Downstairs feels like its own private world. Two additional bedrooms and an exceptionally generous second living room create a versatile configuration for guests, extended family, a home office, or live-in relatives. From the bedrooms, step directly onto your private lanai and toward the pool and gardens, creating an effortless connection to the outdoors. Outside, the beautifully landscaped grounds are designed for privacy and enjoyment. A fabulous intimate lap pool and cozy pool pavilion provides a peaceful focal point for this residence. For energy efficiency, the property is also equipped with 32 photovoltaic panels. The location is equally compelling. Enjoy the charm of Makawao town within walking distance, while Kahului and Baldwin Beach are approximately 20 minutes away. Here, thoughtful architecture, lush grounds, privacy, flexible living spaces, and an enviable Upcountry setting come together in a truly special property. A distinctive home with wonderful possibilities.

1102 Mailuna Pl, Makawao

Listing courtesy of Equity One Real Estate Inc (P).

35 Ohia Lehua Pl, Pukalani
$4,395,000
4 Beds ⋅ 4 Baths ⋅ 409092 MLS ⋅ ACTIVE Status
When HOME is the destination. Set in an IDEAL UPCOUNTRY location, this ENTERTAINER'S DREAM is where luxury, RESORT INSPIRED amenities, and Maui’s natural beauty merge in harmony. Upon entry, BI-COASTAL OCEAN AND MOUNTAIN vistas unfold like nature’s own work of art. Thoughtfully renovated and expanded in 2025, the home was re-imagined as a place of beauty, recreation, and restoration. Perched at Kulamalu Hilltop, an exclusive and highly coveted gated enclave of just 13 residences, this 4-bedroom, 4-bath home offers approximately 3,882 square feet under roof, including a 3-car garage. Soaring ceilings create architectural volume, while hybrid Koa flooring and Roman Gold Travertine establish a rich foundation. In the foyer, a custom glass-enclosed 150+ bottle wine display makes a striking impression. The main living area is anchored by a split-faced marble wall, linear fireplace, suspended glass sculpture chandeliers, and sliding glass walls that open effortlessly to the outdoors, creating the kind of seamless indoor-outdoor living that defines the Maui lifestyle. A private resort unfolds with a natural-style infinity-edge lap swimmable water feature echoing the stillness of a reflection pond. Practice greens with six golf holes, two tee boxes, a sand bunker, and gathering areas with fire pits create a sublime, curated outdoor experience. A gourmet kitchen designed for culinary creativity and entertaining features a multifunctional workstation sink with LED temperature display, waterfall and rain dance functions, Sub-Zero, Wolf, and Bosch appliances, Calacatta West quartz counters, and a beveled glass tile backsplash. The Primary Suite Retreat offers a serene sitting area positioned to take in both ocean and mountain views, with an ensuite spa-like bathroom, dual-sided gas fireplace, and walk-in closet. The game room may also serve as a great room, private lounge, media retreat, or flex space. Tech features include dual-zone AC, Nest thermostat, Blink security, and app-enabled smart home integration. Special features include: This entertainer's dream estate offers bi-coastal ocean and outer island views at Upcountry Maui's most coveted elevation, with convenient access to Maui's top-rated schools. Six-hole private practice green with two tee boxes and sand bunker, natural-style infinity-edge lap pool, extensively and thoughtfully renovated and expanded in 2025, Sub-Zero and Wolf gourmet kitchen, dual-sided gas fireplace, La Cantina sliding pocket doors, custom glass-enclosed 150+ bottle wine display, suspended glass sculpture chandeliers, hybrid Koa flooring and Roman Gold travertine, 40-panel PV solar system, and Tesla EV charging. Gated enclave of just 13 residences. Please see the full list of improvements and features. The pineapple cultivation supports the property’s agricultural land classification, resulting in reduced water rates and other benefits. 35 Ohia Lehua Place offers a rare expression of Upcountry luxury, artfully designed, deeply restorative, and shaped by an awe-inspiring view of nature.

35 Ohia Lehua Pl, Pukalani

Listing courtesy of Maui Real Estate Advisors LLC.

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