Oahu Homes with Cottage Style

Welcome to Oahu, the vibrant heart of Hawaii, where stunning landscapes, rich culture, and a laid-back lifestyle come together to create a paradise like no other. Known as "The Gathering Place," Oahu is the third-largest island in the Hawaiian archipelago, offering a unique blend of urban excitement and serene natural beauty. From the iconic beaches of Waikiki to the lush mountains of the North Shore, Oahu boasts diverse experiences that cater to every lifestyle.

One of the most charming features of Oahu’s real estate market is the abundance of homes with cottage-style architecture. These delightful residences exude a sense of warmth and nostalgia, often characterized by their quaint designs, inviting porches, and lush gardens. Imagine sipping your morning coffee on a sun-drenched lanai, surrounded by tropical flora and the soothing sounds of nature. Cottage-style homes in Oahu are perfect for those seeking a cozy retreat that reflects the island's relaxed atmosphere.

Whether you’re looking for a peaceful escape or a vibrant community, Oahu has something for everyone. The island is home to a variety of neighborhoods, each with its own unique charm. From the artistic vibe of Kailua to the historic streets of Honolulu, you’ll find that each area offers a distinct lifestyle. Embrace the spirit of Aloha as you explore the possibilities of owning a cottage-style home in this tropical paradise. With its enchanting landscapes and friendly communities, Oahu is not just a place to live; it’s a place to call home.

Newest Oahu Homes with Cottage Style

$999,000

4 Beds ⋅ 1 Baths ⋅ 202613721 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Brand new listing in a prime, ultra-convenient Aiea location! Packed with potential, this property uniquely features dual entry access points from Hale Momi Place and a private road, all set on a lot featuring an ample variety of mature tropical trees. Property is to be sold strictly "As-Is", the seller will not perform any fixes or improvements. Buyer are required to conduct their own due diligence. Exceptional opportunity for investors or contractors looking for a project with major upside!

98-256 Hale Momi Place, Aiea

$1,300,000

2 Beds ⋅ 1 Baths ⋅ 202615245 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM

Charming 2-bedroom, 1bath Kailua home offering 828 sq ft of comfortable living space surrounded by a beautiful Tropical Garden. Move-in ready with complete updates including Plumbing redone and total Electrical rewiring. Freshly painted inside and out in September 2025 using Top-tier Sherwin Williams paint. Set on a fully fenced 5,000 sq ft landscaped, fenced yard with a Gated Entry and Banana Trees bearing Fruit. A Pergola including Funiture to enjoy the Outdoors. Enjpy the ultimate Kailua Lifestyle just a short walk or bike riide to world famous Kailua Beach and vibrant Town with Shops and Restaurants. Well loved and cared for by Owner.

491 Kihapai Street, Kailua

$1,100,000

2 Beds ⋅ 1 Baths ⋅ 202614602 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

Cute Cottage freshly painted and move in ready. Numerous upgrades include updated kitchen, bathroom, hardwood flooring, windows, split a/c, aluminum roof with two car carport. Location, Location, Location in the heart of Kailua bordering Kawainui Marsh. This CPR is only attached at the carport and VA approved. Back property is also for sale. Don't miss a unique opportunity to purchase two properties for extended family. Or live in one property and rent out the other. Properties can be purchased separately as well. Endless possibilities!!

739 Kahoa Drive, Kailua

$749,800

2 Beds ⋅ 2 Baths ⋅ 202614619 MLS ⋅ FS - Fee Simple Tenure ⋅ 12 DOM

AC and NO MAINTENANCE FEE on this charming, detached, single family home. Yes you can afford a detached SINGLE FAMILY HOME. If you can afford a $575,000 condo with a $1000 per month maintenance fee you can afford this home! (Total monthly payment would be similar). This lovely two bedroom, two bathroom home has a large fenced yard with storage shed, AC and large windows to let in tons of light. Come see this charming home with tons of character and make it yours. Located in historic Ewa Villages neighborhood the HOA fee is only $30 per month and there is NO MAINTENANCE FEE! No carpet and two full bathrooms. Washer and Dryer included. Plenty of parking in the gate and driveway. Check out our virtual tour! *School zones obtained from Hawaii DOE School Finder website. Buyer to verify.

91-1661 Orrick Street, Ewa Beach

$1,180,000

3 Beds ⋅ 2 Baths ⋅ 202614454 MLS ⋅ FS - Fee Simple Tenure ⋅ 14 DOM

Rare opportunity in desirable Palolo Valley! This versatile home offers flexible living and convenient in-town access. The main level features 3 bedrooms (with hardwood floors throughout) and 1 full bath, while the finished lower level includes a spacious storage area with a half bath—ideal for a workshop, home office, hobby space, or extra storage. A studio-style suite with a full bath was created by expanding the former laundry area and includes a refrigerator with space for a potential induction cooktop. The paved front yard has 2 parking spaces, plus a tandem 2-car carport (total of 4 parking). Enjoy outdoor laundry facilities, cooling trade winds, and a mature mango tree in the backyard. Conveniently located near Hapa Local Market & Grill, Kaimuki's popular cafés, restaurants, and boutiques, Kahala Mall, the University of Hawaii at Manoa, Kapahulu, Waikiki, parks, schools, beaches, and convenient H-1 freeway access. Enjoy the best of island living just minutes from town. Move right in or update to match your personal style.

3279 HOANOHO Place, Honolulu

$1,499,000

5 Beds ⋅ 4 Baths ⋅ 202614480 MLS ⋅ FS - Fee Simple Tenure ⋅ 14 DOM

Rare opportunity to own a beautifully renovated multi-generational property on one of Lower Nuuanu's most coveted tree-lined streets. Ideally located across the street from Ma'ema'e Elementary School, this exceptional property offers the flexibility and convenience today's buyers are looking for. The renovated single-level main home features 3 bedrooms, 2 bathrooms, an open-concept kitchen, LVT flooring, an updated roof, and French doors leading to a spacious covered lanai for seamless indoor-outdoor living. A renovated detached bonus structure is currently configured with 2 bedrooms and 2 bathrooms, offering flexible space for extended household living, guests, a home office, hobbies, or other uses. Enjoy cool tradewinds, a large enclosed yard with lychee, avocado, star fruit, orange, and dragon fruit trees, solar hot water, a two-car carport, and additional driveway parking. Minutes from Downtown, Chinatown, H-1, restaurants, and shopping. Bedrooms and bathrooms do not match tax records. Buyers to do their own due diligence during escrow. *some photos have been digitally de-cluttered*.

71 Kawananakoa Place, Honolulu

$1,690,000

4 Beds ⋅ 3 Baths ⋅ 202614340 MLS ⋅ FS - Fee Simple Tenure ⋅ 17 DOM

Experience elevated island living in this fully remodeled, single-level home in the heart of Kailua. Renovated from top to bottom, this property feels virtually new and offers the perfect blend of modern design and everyday comfort. The home features a 3-bedroom, 2-bath main residence plus a connected 1-bedroom, 1-bath suite with a kitchenette, providing exceptional flexibility for extended family, guests, a home office, or potential rental income. Inside, a bright open-concept floor plan seamlessly connects the kitchen, living, and dining areas, creating an inviting space for both entertaining and daily living. The bedrooms feature premium DuChâteau hardwood flooring, adding warmth and an elegant finish throughout. A thoughtfully designed hidden laundry room enhances functionality while maintaining clean lines and a spacious feel. Outside, enjoy a fully fenced, oversized backyard—perfect for entertaining, pets, or relaxing in your own private retreat—along with a generous front yard that enhances the home's curb appeal. Turnkey and move-in ready, this exceptional property offers modern island living in one of Oahu's most desirable beach communities.

1225 Mokapu Boulevard, Kailua

$1,298,000

3 Beds ⋅ 3 Baths ⋅ 202612198 MLS ⋅ FS - Fee Simple Tenure ⋅ 19 DOM

Cooled by gentle mountain breezes & blessed with sweeping coastline views stretching toward Diamond Head, this exceptional 3-unit property offers the kind of island lifestyle people dream about. Upstairs, a spacious covered lanai becomes the heart of the home, a place to greet the morning with a cup of coffee as the sun rises over the Pacific, to gather with friends for leisurely meals, or unwind in the evening while watching mesmerizing sunsets paint the sky in shades of gold & pink. The well-appointed kit flows effortlessly to the outdoor living space, making entertaining and dining al fresco both easy & enjoyable. Whether preparing a casual breakfast or hosting a sunset dinner, everything is designed to embrace the HI indoor-outdoor way of life. The upstairs residence features 2 comfortable bedrooms & 1 bathroom, creating a peaceful retreat where the sights, sounds & breezes of the islands are never far away. The downstairs 1 bedroom unit has a generous sized living area leading out to the covered lanai. Easy walking distance to Waialae Avenue with numerous restaurants & boutique shops. Small studio also included in the offering.

4137 Sierra Drive, Honolulu

$860,000

4 Beds ⋅ 3 Baths ⋅ 202614132 MLS ⋅ FS - Fee Simple Tenure ⋅ 20 DOM

Spacious and versatile single-family home in Ewa Beach offering over 2,000 sq ft of interior living space, with excellent multi-family/income potential. The main residence was freshly painted both inside and out, and features a flexible layout with 3 bedrooms and 2 bathrooms, which could easily be divided into 2 sections, the front having 2 bedrooms, 1 bathroom, a kitchen and living room, and the back having 1 large bedroom, a full bath, wet bar, and living room. There is an interior door that allows for the separate living configurations. In addition, there's a separate studio in the back, and 2 sets of washer/dryers, providing added value—ideal for extended family, guests, home office, or rental. The home has been upgraded over the years, offering move-in-ready comfort while still allowing room for personalization. There are 30 PV panels + 2 Tesla batt (via loan that will transfer to buyer). Enjoy the benefits of no association/no HOA fees, keeping ownership simple. Conveniently located near the beach and Wai Kai Lagoon, with close proximity to dining, shopping, & outdoor recreation. A great opportunity for buyers seeking space, flexibility, great value, and investment potential.

91-1157 Hanaloa Street, Ewa Beach

$1,200,000

2 Beds ⋅ 2 Baths ⋅ 202613526 MLS ⋅ FS - Fee Simple Tenure ⋅ 33 DOM

LOCATION, LOCATION, LOCATION, 6900+ SQ. FT IN HIGHLY DESIRABLE LILIHA PUUNUI MAEMAE ELEMENTARY SCHOOL DISTRICT. BACK AREA COULD BE CONVERTED TO A 3/2 ADU OR WHATEVER YOU DREAM OF. THIS IS TRULY A BLANK CANVAS. ORIGINAL HOME FEATURES HARDWOOD FLOORS AND ROOM TO EXPAND EASILY.

2124 Bachelot Street, Honolulu

$1,495,000

3 Beds ⋅ 2 Baths ⋅ 202613582 MLS ⋅ FS - Fee Simple Tenure ⋅ 28 DOM

Charming home with separate cottage. Home is updated with lovely merbau (Indonesian hardwood) floors, kitchen and bath. Main house has three bedrooms & one bath. Carport contiguous to the LR could be enclosed to increase living area by 240 sq ft. There are many leased PV panels. Large private yard has plenty of room to expand primary bedroom and add a bath. Cottage has a very private entry and its own deck and yard area. Cottage is permitted for use as additional living space to main house. Some of the photos are digitally staged. Property is located in the friendly neighborhood of Pohakupu. Kailua town and beach are a short distance away. This is a very special property.

1254 Ulupii Street, Kailua

$16,500,000

6 Beds ⋅ 8 Baths ⋅ 202611158 MLS ⋅ FS - Fee Simple Tenure ⋅ 33 DOM

Sophisticated, Modern, Unlimited Ocean Views...Designed to relish in the beauty of magnificent indoor spaces coupled w/ a seamless integration to expansive outdoor living this stunning ultra-luxury residence designed by renowned HI Architect Jim McPeak offers uninterrupted Diamond HD, ocean & coastline views, and the best direct sunset vistas on the island. Situated on Oahu’s Southeastern shoreline overlooking Maunalua Bay this breathtaking 6-BD, 7.5-BA residence offers exceptional appointments & a true private luxury resort experience. The Great Rm welcomes you w/its awe-inspiring panoramic landscapes, soaring custom wood inlaid ceilings, pocketing walls of glass & assortment of natural stone textures. The chef’s kitchen w/prof appliances provides a wonderful connection to both the dining alcove & lounge areas. The Primary Suite w/ secluded sitting nook, seaside lanai and dream spa like bath is stunning, Each BD suite provides a sensory experience & soothing sounds of the ocean waves. This modern-day masterpiece is complete w/ a gated, dual access driveway providing ample onsite parking + garage parking for 3-cars. For those in search of a stunning island villa, welcome home.

176 Hanapepe Loop, Honolulu

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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.