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

1011 Mokulua Drive, Kailua $8,995,000

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
202619411 MLS
FS - Fee Simple Tenure
19 DOM
ACTIVE Status

41-539 Makakalo Street, Waimanalo $5,400,000

A Rare Waimanalo Opportunity: Where Country Living Meets Exceptional Possibilities. Perfect for equestrian enthusiasts, ranchers, farmers, and those seeking a truly uniqu...

3 Beds
2 Baths
202619098 MLS
FS - Fee Simple Tenure
21 DOM
ACTIVE Status

1254 Ulupii Street, Kailua $1,445,000

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
202619271 MLS
FS - Fee Simple Tenure
22 DOM
ACTIVE Status

315 A Ulupaina Street, Kailua $969,000

Great location for this tucked away 2 bedroom 1 bath Kailua cottage. Located on a quiet lane off of Ulupaina Street where there is a wide private driveway with access fo...

2 Beds
1 Baths
202618404 MLS
FS - Fee Simple Tenure
35 DOM
ACTIVE UNDER CONTRACT Status

41-1451 Laukalo Street, Waimanalo $359,900 ▼

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
77 DOM
ACTIVE Status

491 Kihapai Street, Kailua $1,250,000 ▼

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
89 DOM
ACTIVE Status

1225 Mokapu Boulevard, Kailua $1,580,000 ▼

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
102 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
124 DOM
ACTIVE Status

409 Wanaao Road, Kailua $2,295,000 ▼

Now offered below tax assessed value — your opportunity to own in Kailua just got better! Our seller has made new improvements to make this home shine! Experience the bes...

4 Beds
4 Baths
202612015 MLS
FS - Fee Simple Tenure
137 DOM
ACTIVE Status

244 Awakea Road, Kailua $3,045,000 ▼

MAJOR PRICE REDUCTION! Exceptional opportunity in a desirable location within Kailua Estates! 244 Awakea Road is a beautifully remodeled plantation style property situat...

6 Beds
3 Baths
202608800 MLS
FS - Fee Simple Tenure
177 DOM
ACTIVE UNDER CONTRACT 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
355 DOM
ACTIVE Status