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

41-1451 Laukalo Street, Waimanalo $391,500

Your Waimanalo Village Lifestyle begins here. Hawaii Housing Finance and Development Corp. (HHFDC) Leasehold property, (NOT HAWAIIAN HOMESTEAD) offers a unique opportuni...

4 Beds
3 Baths
202616058 MLS
LH - Leasehold Tenure
25 DOM
ACTIVE Status

219 S Kalaheo Avenue, Kailua $2,250,000

An incredible opportunity in one of Kailua’s most sought-after locations, just moments from Kailua Beach and minutes from Kailua Town. Set on an expansive 12,773 sq. ft. ...

4 Beds
3 Baths
202615759 MLS
FS - Fee Simple Tenure
30 DOM
ACTIVE UNDER CONTRACT Status

491 Kihapai Street, Kailua $1,295,000 ▼

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 inclu...

2 Beds
1 Baths
202615245 MLS
FS - Fee Simple Tenure
37 DOM
ACTIVE Status

739 Kahoa Drive, Kailua $1,050,000 ▼

50K PRICE REDUCTION AND READY FOR A BUYER!!! DON'T MISS THIS OPPORTUNITY. Cute Cottage with a fenced in yard that is freshly painted and move in ready. Numerous upgrades ...

2 Beds
1 Baths
202614602 MLS
FS - Fee Simple Tenure
39 DOM
ACTIVE Status

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
50 DOM
ACTIVE Status

1254 Ulupii Street, Kailua $1,495,000

Need $$ to help pay the Mortg? This charming homes has a cottage in the back yard that has been rented for $2,300 a mo. House features lovely hardwood floors, updated ki...

3 Beds
2 Baths
202613582 MLS
FS - Fee Simple Tenure
61 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
71 DOM
ACTIVE UNDER CONTRACT 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
72 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
74 DOM
ACTIVE Status

409 Wanaao Road, Kailua $2,325,000 ▼

Back on the market and now offered at $174,000 below original list price — your opportunity to own in Kailua just got better! Our seller has made new improvements to make...

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

6 N Kalaheo Avenue, Kailua $4,249,000 ▼

Experience multi generational luxury living,just moments from famous white sand Kailua Beach with shopping and dining close by.Situated on a landscaped 11,005 sq. ft. lev...

6 Beds
5 Baths
202610270 MLS
FS - Fee Simple Tenure
103 DOM
ACTIVE Status