Kailua Homes with Cottage Style

Nestled on the stunning windward coast of Oahu, Kailua is a tropical paradise that embodies the spirit of Hawaiian living. Known for its breathtaking beaches, lush landscapes, and vibrant community, Kailua is the perfect blend of relaxation and adventure. With its crystal-clear waters and soft, sandy shores, residents and visitors alike can enjoy a variety of outdoor activities, from kayaking to hiking the iconic Lanikai Pillbox Trail. The area is also home to charming boutiques, delightful eateries, and a welcoming community that makes everyone feel at home.

One of the standout features of Kailua's real estate market is its enchanting cottage-style homes. These unique residences exude character and warmth, often featuring open floor plans, cozy nooks, and inviting outdoor spaces that seamlessly blend with the island's natural beauty. Many homes come adorned with lush gardens, providing a serene escape right in your backyard. The cottage style is perfect for those seeking a laid-back lifestyle, offering a sense of nostalgia while incorporating modern amenities.

Living in a cottage-style home in Kailua means embracing a slower pace of life, where morning strolls on the beach and afternoon barbecues with friends become part of your daily routine. With a strong sense of community and a plethora of recreational activities, Kailua is not just a place to live; it’s a lifestyle waiting to be embraced. Discover the charm of Kailua and find your dream cottage-style home in this idyllic Hawaiian haven.

Newest Kailua Homes with Cottage Style

1225 Mokapu Boulevard, Kailua $1,690,000

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 o...

4 Beds
3 Baths
202614340 MLS
FS - Fee Simple Tenure
5 DOM
ACTIVE Status

1254 Ulupii Street, Kailua $1,495,000

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...

3 Beds
2 Baths
202613582 MLS
FS - Fee Simple Tenure
16 DOM
ACTIVE Status

1461 Aunauna Street, Kailua $2,450,000

Live at the top of Keolu Summit in Hillcrest with 180 degree views of the Koolau mountains, Olomana peaks, Enchanted Lake, and Kailua Bay. A stunning viewscape captured ...

4 Beds
3 Baths
202612934 MLS
FS - Fee Simple Tenure
26 DOM
ACTIVE Status

1586 Mokulua Drive, Kailua $11,950,000

LANIKAI 5 STAR RESORT, with steps right into the sea. This charming jewel box sits right on the bright blue clear waters of Lanikai with a perfect view of the Mokulua Isl...

4 Beds
5 Baths
202611360 MLS
FS - Fee Simple Tenure
27 DOM
ACTIVE Status

1011 Mokulua Drive, Kailua $9,450,000

TIMELESS LANIKAI RESORT LIVING. Exceptional custom residence in coveted Lanikai w/beach access across the street. Offering 4-BD, 6.5-BA, a private studio apartment suite,...

4 Beds
7 Baths
202612618 MLS
FS - Fee Simple Tenure
29 DOM
ACTIVE Status

409 Wanaao Road, Kailua $2,395,000

A brand new roof and now offered at $105,000 below original list price — your opportunity to own in Kailua just got even better! Experience the best of island living in t...

4 Beds
4 Baths
202612015 MLS
FS - Fee Simple Tenure
40 DOM
ACTIVE UNDER CONTRACT Status

691 Kihapai Street Unit B, Kailua $948,000 ▼

BREAKING NEWS: Seller offering potential assumable mortgage to veterans only currently at 2.25%, all for more information. Wake up in your own Kailua cottage, sip coffee ...

2 Beds
1 Baths
202611865 MLS
FS - Fee Simple Tenure
42 DOM
ACTIVE UNDER CONTRACT Status

315 Iliaina Street, Kailua $1,875,000

Nestled within one of Kailua’s favorite neighborhoods, Kalaheo Hillside, 315 Iliaina Street is filled with potential and island charm. The property includes two separate ...

3 Beds
3 Baths
202609716 MLS
FS - Fee Simple Tenure
62 DOM
ACTIVE Status

244 Awakea Road, Kailua $3,150,000 ▼

Rarely available in Kailua Estates, 244 Awakea Rd is a beautifully remodeled plantation-style property on a spacious 10,000 sq ft lot just a short stroll to Kailua Beach ...

6 Beds
4 Baths
202608800 MLS
FS - Fee Simple Tenure
80 DOM
ACTIVE Status

41-471 Kalanianaole Highway, Waimanalo image

41-471 Kalanianaole Highway, Waimanalo $24,900,000

Live among Hawaii's natural wonders & unsurpassed beauty at this extraordinary Pahonu Beach estate. Spanning nearly 1 acre, this oceanfront property includes 152 linear ...

10 Beds
9 Baths
202525519 MLS
FS - Fee Simple Tenure
258 DOM
ACTIVE Status

572C N Kalaheo Avenue, Kailua $18,880,000

Welcome to this exceptional Kailua beachfront estate. This gated resort-like retreat is situated on nearly an acre of land fronting one of the most beautiful beaches in ...

12 Beds
16 Baths
202520168 MLS
FS - Fee Simple Tenure
321 DOM
ACTIVE Status

29 Alala Road, Kailua $1,495,000

Your gateway to turquoise waters, soft white sand, and the quintessential island lifestyle! Waking up to ocean breezes and a stroll across the street to world-famous Kai...

2 Beds
2 Baths
202519242 MLS
FS - Fee Simple Tenure
328 DOM
ACTIVE UNDER CONTRACT Status