living in kailua, hawaii neighborhood guide 2020

Kailua Real Estate

Commercial and Residential Real Estate development in Kailua is scarce and this exactly how the locals wish to keep it. Kailua was once a sleepy little beach town but Coastal Magazine features and Instagram tags have put it on the world's stage, attracting tourists, buyers, and renters from all over the globe.

> > To learn more about what makes Kailua so special, check out our Ultimate Guide to Kailua Living.

Any new development proposed in the region is met with stiff opposition from the community as it attempts to preserve what little is left of Old Kailua. On the other side of the coin, lack of inventory puts Kailua homes and condos in short supply and high demand which is a sure fire way to send prices through the roof. Check out the Kailua Real Estate Market Trend below that highlights average prices over the last 40 years:

kailua real estate market price trends

If you're moving to area you'll be pleased to find one of the widest varieties of home types on the island. The presence of multiple Kailua and Lanikai Beach, Enchanted Lake, and multiple canals see many homes with water frontage; one Hawaii's best natural amenities. Homes in Kailua benefit from just a short walk or bike ride from any beach in the neighborhood, and same is true for premier convenience to Wholefoods and Kailua Town.

Kailua Real Estate Market Insights

Kailua Condos will be limited to the options in Kailua Town, with most above the 9th floor achieving ocean views if located on the ocean side of the building. from $450,000 - $1.2M while Kailua homes range from tear-down conditions of roughly $700,000 up to the ultra luxury Kailua beach home estates of nearly $28M.
- Top Pick: Ka Malanai by D.R. Horton Hawaii
Single Family Homes in Kailua will range from modest plantation style cottages in the $800,000 to the multi-million dollar luxury beachfront estates of the Beachside and Lanikai neighborhoods.
Kailua home prices are highest near the beach, and you'll typically find the larger lot sizes closer to the beach as well. Prices will gradually decrease as you near the mountains and move away from the heart of Kailua Town.

Popular Kailua Neighborhoods

Now this is completely subjective, but in being a Kailua Real agent as well owning a few homes in the neighborhood myself, I feel qualified to give you a generalized hierarchy of how most Kailua realtors and buyers view neighborhoods in the region. The list below itemizes the neighborhoods with closest beach proximity and works back towards the mountains. Conveniently enough, this is how Kailua prices behave as well. There is also consideration given the the neighborhoods with the most "mind share," which is why Lanikai tops the list. It has the most brand awareness!

Lanikai Real Estate offers a lifestyle of living in a post card. Enjoy front row seats to one of the best beaches in the world with powdery white sand, every hue of crystal blue waters, and the Mokulua "Twin" Islands just begging you to visit them by kayak or stand-up paddleboards. Average lot sizes are 10,000 - 12,000sqft and Lanikai homes for sale will range from $1.2M to the ultra luxurious Lanikai Beach houses for sale up to $21M. Main thoroughfares are Aalapapa Drive(further from the beach) and Mokulua Drive(closest to the beach).
Beachside is the neighborhood in Kailua that runs the length of North Kalaheo avenue, offering Kailua Beachfront Homes or homes just a blog away from the beach. Kailua Beachside homes for sale usually start around $2M with lot sizes averaging 10,000 to 12,000sqft however, there are a few 1+ acre lots that offer expansive Kailua Beach Estates upwards of $27,000,000. You will see some of the most expensive homes in Hawaii here, and definitely on Oahu.
Kuulei Tract real estate offers some of the closest homes to Kailua Town, and only 1-2 blocks from Kailua Beach. These homes typically offer stunning landscapes over their 10,000 - 12,000sq lots, many of which with pools. Kuulei Tract homes for sale range from $1.5M to $2.2M and offer premier convenience to all of Kailua's best features.
Kalama Tract real estate features the homes just a block back from Kailua Beach, on the mountain side of North Kalaheo Avenue. These are some of my favorite homes in Kailua as they're just a stone's throw from the beach, they feature killer lots and curb appeal, yet they don't see the excessive price points of direct beach access. Kalama Tract homes for sale are limited, they're hard to let go, and lot sizes are generally between 10,000-12,000sqft. Plan on prices ranging from $1.3M to $1.8M
Aikahi Park is home to the favorite Halloween destination for trick or treating in Kailua so if you're not the festive type, you'll want to turn off all your lights on October 31st! This feature is due largely in part to the wide sidewalks, lightly trafficked streets, and large yard spaces that provide an ample canvas for your Halloween set ups. It's not uncommon to see a number of Aikahi homes for sale with pools either. Plan for lot sizes of around 10,000sq, direct access to Marine Corp Base Hawaii, and prices between $1.1M - $1.6M.
Coconut Grove real estate offers you premier Kailua Beach access within a 1-mile radius and mostly quaint plantation style cottages. Not a whole lot of sidewalks in Coconut Grove but that doesn't stop bikers and runners. Everybody's on the move to the beach here so stay alert when driving through the neighborhood. Average Coconut Grove homes for sale range from $800,000 to $950,000 with smaller lot sizes than most of Kailua. At 5,000 to 7,500sqft, you better hope you like your neighbors.
Enchanted Lake real estate gets a little more suburban with wide streets and sidewalks, and large level lot sizes. Some homes for sale in Enchanted Lake will have lake and canal frontage but don't jump in! It's not a lake you want to swim in. Take in the views and launch the kayak, but don't spend time getting wet here. Enchanted Lakes homes feature lot sizes of 7,500 - 15,000sqft with typical prices between $850,000 - $1.4M.
Maunawili is a quiet, and slightly wetter lifestyle than the rest of Kailua as these homes are nestled between the Koolau and Olomana Mountains. Rainfall becomes more prevalent as you near the mountains so what you lose in sunshine, you gain in lush tropical landscapes! Plan on lot sizes around 10,000sq but due to its more rural setting, you will find some oversized lots of up to an acre or two. Maunawili homes for sale are typically priced between $1M and $2.7M.

Not sure that you can commit to buying a Kailua home for sale? Give a look to all Kailua rentals.

Kailua Homes For Sale | Oahu, Hawaii

361 Kailua Road Unit 8309, Kailua — Ka Malanai@Kailua $895,000

Enjoy the Gorgeous sunrise over Lanikai from your living room and Primary Bedroom ! Feast your eyes on this highly desirable corner end unit with beautiful kitchen upgra...

2 Beds
2 Baths
202101523 MLS
Ka Malanai@Kailua Bldg.
1 DOM

41-695 Kaulukanu Street, Waimanalo image

41-695 Kaulukanu Street, Waimanalo $2,600,000

MOTIVATED SELLER, WILL CONSIDER ALL OFFERS! Fantastic opportunity to own and live on a serene, lush level lot set along the majestic Koolau mountains. Accessed by the "K...

202101471 MLS
3 DOM

161 Kaluamoo Street, Kailua $1,998,000

Welcome to one of Kailua's most desirable locations! Just a short stroll to beautiful Kailua Beach, and Kainalu Bike Path to get to the center of all the Kailua Town has ...

5 Beds
4 Baths
202101277 MLS
4 DOM

690 Old Mokapu Road, Kailua $1,998,000

This single level, renovated Kaimalino home is just a block from peaceful Turtle Beach. Larger lot 12k SF. Two separate living units: 1 bedroom 1 bath with own private ga...

4 Beds
3 Baths
202100939 MLS
4 DOM

161 Kaluamoo Street, Kailua $1,998,000

Welcome to one of Kailua's most desirable locations! Just a short stroll to beautiful Kailua Beach, and close to Kainalu Bike Path to get to the center of all that Kailua...

202101287 MLS
4 DOM

259 Kaelepulu Drive, Kailua $1,999,000

Don' t miss this opportunity to be the new owner of this mid-century modern gem, reminiscent of a simpler era. Built in 1955, designed by renowned architect Philip Fisk, ...

4 Beds
2 Baths
202100860 MLS
4 DOM

531 Kaiemi Street, Kailua $1,498,000

Amazing opportunity to own this beautiful, well maintained home with permitted Accessory Dwelling Unit (ADU) and in ground salt water pool. This 3/2 home has a 2/1 ADU an...

5 Beds
3 Baths
202100195 MLS
5 DOM

210 Kalama Street, Kailua $1,015,000

Live the Kailua lifestyle in this charming Kama’aina gem located on a spacious, 10,000 sf level corner lot. Just one block away from Kalama Beach access. Enjoy the trade ...

3 Beds
3 Baths
202100739 MLS
6 DOM

350 Aoloa Street Unit A222, Kailua image

350 Aoloa Street Unit A222, Kailua — Koolau Vista $475,000

Live in Kailua without the sticker shock! Koolau Vista is a VA approved complex located in the heart of Kailua & walking distance to Target, shops, and restaurants. Remod...

2 Beds
2 Baths
202101084 MLS
Koolau Vista Bldg.
8 DOM

602 Kawainui Street, Kailua $1,225,000

Must see to appreciate Island living in this Newer well constructed home! Built in 2014 & in Excellent condition, this inviting Open style home with desirable curb appeal...

4 Beds
3 Baths
202100666 MLS
11 DOM

511 Wailepo Street, Kailua $3,000,000

Older three story walk-up building in the heart of old Kailua. Close to shopping, schools, all features of Kailua. Some units require substantial renovation. Please conta...

202029872 MLS
17 DOM

1020 Aoloa Place Unit 405B, Kailua image

1020 Aoloa Place Unit 405B, Kailua — Windward Cove $699,000

Centrally located yet secluded complex with tropical greenery, ponds and waterfalls. This top floor corner unit features remodeled kitchen and baths, floor to ceiling pla...

3 Beds
2 Baths
202100318 MLS
Windward Cove Bldg.
17 DOM

433 Keolu Drive, Kailua $1,688,000

Hawaiian living at its best. Waterfront, 6 bedrooms, 4 baths, 2 living rooms, 2 garages, kitchen, wet bar, 3 lanais. Excellent neighborhood of Enchanted Lake in Kailua. R...

5 Beds
4 Baths
202029307 MLS
34 DOM

42-100 Old Kalanianaole Road Unit 8, Kailua image

42-100 Old Kalanianaole Road Unit 8, Kailua $1,708,895

Rarely does an opportunity present itself to acquire the most enviable and exclusive 2 acres of agricultural land in a gated community in Olomana Heights! Magnificent oce...

202032461 MLS
35 DOM

380 Lama Place, Kailua $14,800,000

Once in a long while, a Hawai’i property with thoughtful design to match its exquisite environment comes to market. The contemporary elegance of 380 Lama Place is rivaled...

4 Beds
5 Baths
202027954 MLS
35 DOM

819 Oneawa Street Unit D, Kailua $959,000

Quiet Kailua oasis tucked away off Oneawa at the very end of private lane. Three blocks from the beautiful white sands of Kailua Beach! Fully renovated home in 2017, und...

2 Beds
1 Baths
202032306 MLS
39 DOM

41-1010 Laumilo Street, Waimanalo $2,895,000

A DISTINCTIVE HOME set between the magical Koolau mountains and the pristine sands of Waimanalo beach. Live like no-one else in this masterpiece, where every detail has ...

4 Beds
3 Baths
202032232 MLS
39 DOM

144 Kaapuni Drive, Kailua $7,500,000

Be one of the few to create a personal resort! Legacy estate sized parcel fronting Kailua Beach is ready for the home(s) of your dreams. Nearly an acre in a premium loca...

202028680 MLS
44 DOM

1528 Mokulua Drive, Kailua $15,600,000

Enjoy breathtaking Lanikai view of the turquoise ocean. Swim and kayak in the warm waters right from your own backyard. This oceanfront sanctuary was completed in 2018, l...

5 Beds
7 Baths
202025053 MLS
47 DOM

41-960 Waikupanaha Street, Waimanalo image

41-960 Waikupanaha Street, Waimanalo $1,200,000 ▼

Picturesque Working Estate framed by Mount Olomana and the Koolau Mtns. Sale of the property includes the sale of two established positive cash flow businesses, all heavy...

2 Beds
3 Baths
202031657 MLS
49 DOM

1408A Mokulua Drive, Kailua $6,280,000

Oceanfront luxury living in world renowned Lanikai. Unparalleled direct views of the Mokulua islands and sparkling ocean await you in this peaceful, private oasis. The cr...

4 Beds
4 Baths
202030418 MLS
48 DOM

1051 Kahili Street, Kailua $1,999,000

One of a kind Kailua Palace available now! Completely new construction, with over 5200 sq. ft. under roof, with two (2) car garages, and onsite parking for 6-8 more car...

10 Beds
10 Baths
202031565 MLS
52 DOM

Lopaka Way Unit 3,4, Kailua $1,495,000

Paradise found. Estate sized lots in private community of Maunawili Summit in Kailua. Stunning Ocean, Olomana Mountain, Golf Course, and Koolau views. Mesmerizing starga...

202029949 MLS
61 DOM

Lopaka Way Unit Lot 5, Kailua $1,345,000

Paradise found. Estate sized lots in private community of Maunawili Summit in Kailua. Stunning Ocean, Olomana Mountain, Golf Course, and Koolau views. Tranquil & quiet. ...

202029948 MLS
61 DOM

Lopaka Place Unit Lot 6, Kailua $1,295,000

Paradise found. Estate sized lots in private community of Maunawili Summit in Kailua. Stunning Ocean, Olomana Mountain, Golf Course, and Koolau views. Mesmerizing starga...

202029947 MLS
61 DOM

Lopaka Way Unit Lot 2, Kailua $1,295,000

Paradise found. Estate sized lots in private community of Maunawili Summit in Kailua. Stunning Ocean, Olomana Mountain, Golf Course, and Koolau views. Mesmerizing starga...

202029950 MLS
61 DOM

43 Oneawa Street Unit #3, Kailua $65,000

Rare opportunity to purchase a turn-key restaurant, located in Kailua Town, in a high traffic shopping center conveniently located on the inner corner a strip mall. Ideal...

202029958 MLS
61 DOM

41-435 Kalanianaole Highway, Waimanalo image

41-435 Kalanianaole Highway, Waimanalo $6,950,000

An iconic retreat on the beach! Located on the famed Windward Coast, and arguably the best oceanfront lot on this particular shoreline, this extraordinary property presen...

7 Beds
7 Baths
202029343 MLS
63 DOM

703 & 707 Kihapai Place, Kailua $3,200,000

Two side by side A2 zoned lots totaling 12sq/ft. Each lot has two duplexes giving you financing flexibility. 8 units total. Each unit is a 2 bed/1 bath. Average current r...

16 Beds
8 Baths
202029400 MLS
68 DOM

1030 Aoloa Place Unit 103A, Kailua image

1030 Aoloa Place Unit 103A, Kailua — Windward Harbour $659,000

E Komo Mai! Convenient first level location for this beautiful 1200 sq ft, 3- bedroom/ 2 bath condo in tranquil Windward Harbour. Koi pond and resort like gardens through...

3 Beds
2 Baths
202029205 MLS
Windward Harbour Bldg.
70 DOM

144 Kaapuni Drive, Kailua $7,500,000

Be one of the few to create a personal resort! Legacy estate sized parcel fronting Kailua Beach is ready for the home(s) of your dreams. Nearly an acre in a premium loca...

202028677 MLS
81 DOM

449 Ilimano Street, Kailua $1,099,000

Rare single-family home with a detached ohana located in Kalaheo Hillside is waiting for you to uncover all of its hidden potential. This hidden gem comes with a pool, an...

5 Beds
3 Baths
202028255 MLS
16 DOM

1194A Kamahele Street Unit 2703, Kailua image

1194A Kamahele Street Unit 2703, Kailua — Bluestone $1,265,000 ▼

This rarely available corner unit in coveted Bluestone offers a two-car garage, wrap-around lanai and bonus room that can be used as an office, den, TV room, or extra bed...

3 Beds
3 Baths
202028082 MLS
Bluestone Bldg.
75 DOM

703 Kihapai Place, Kailua $3,200,000

Attention Bill 7 Developers! Two side by side A2 zoned lots totaling 12sq/ft. Each lot has two duplexes giving you financing flexibility. 8 units total. Each unit is a...

202027374 MLS
97 DOM

322 Aoloa Street Unit 603, Kailua — Windward Passage $629,800 ▼

Tastefully remodeled 2 bedroom 2 bath unit above treetops with a Peekaboo view of the Kailua beach. Unit is located on the desirable side of the building attracting natur...

2 Beds
2 Baths
202027063 MLS
Windward Passage Bldg.
94 DOM

335 Ilimano Street, Kailua $2,250,000

This wonderful residence is equipped to accommodate a multigenerational family or possible care/foster home. A thoughtfully planned home flow seamlessly with a flexible f...

202025474 MLS
111 DOM

335 Ilimano Street, Kailua $2,250,000

This wonderful residence is equipped to accommodate a multigenerational family or possible care/foster home. A thoughtfully planned home flow seamlessly with a flexible f...

8 Beds
9 Baths
202025472 MLS
111 DOM

14 Aulike Street Unit 903, Kailua — Meridian East $799,000 ▼

DON’T MISS the stunning and expansive blue ocean views in this bright, breezy renovated corner condo, located in the heart of charming Kailua Town. This spacious 3 BR/2BA...

3 Beds
2 Baths
202025092 MLS
Meridian East Bldg.
102 DOM

1370 Mokolea Drive, Kailua $3,200,000

A beautifully remodeled, two-storied four-bedroom, three baths Lanikai home AND a 2 bedroom, 1.5 bath cottage nestled within landscaped gardens. Recent updates include a ...

6 Beds
5 Baths
202024670 MLS
117 DOM

41-010 Wailea Street, Waimanalo $14,500,000

Rental Income has SIGNIFICANTLY Jumped since city enacted Bill 89! Amazing opportunity to own a very very special historical property legally grandfathered Hotel owned by...

202024047 MLS
122 DOM

22 Palione Place, Kailua $4,475,000

Legal Vacation Rental with a rare and current Nonconforming Use Permit. Gorgeous, private, gated tropical oasis just steps from beautiful Kailua Beach. So much flexibilit...

6 Beds
6 Baths
202024232 MLS
88 DOM

41-010 Wailea Street, Waimanalo $14,500,000

Rental Income has SIGNIFICANTLY Jumped since city enacted Bill 89! Amazing opportunity to own a very very special historical property legally grandfathered Hotel owned by...

202024044 MLS
129 DOM

145 Kailuana Loop, Kailua $27,500,000

Unparalleled in grandeur on Oahu’s emerald Windward side, Kai Moena, “House of the Resting Sea,” is a stunning oceanfront estate that reflects a skillful merging of moder...

10 Beds
11 Baths
202023480 MLS
131 DOM

1020 Aoloa Place Unit 206A, Kailua image

1020 Aoloa Place Unit 206A, Kailua — Windward Cove $650,000 ▼

Lowest priced 3/2/2 in Kailua!! Beautiful 3-bedroom 2-bath 2-parking unit offers lush tropical views of gardens and ponds. Large open lanai with no neighbor on one side. ...

3 Beds
2 Baths
202020591 MLS
Windward Cove Bldg.
164 DOM

Lopaka Way Unit 1, Kailua $895,000

Paradise found. Estate sized lots in private community of Maunawili Summit in Kailua. Stunning Ocean, Olomana Mountain, Golf Course, and Koolau views. Mesmerizing stargaz...

202020200 MLS
168 DOM

614 Wailepo Street, Kailua $4,999,999 ▼

The offering consists of the extremely rare opportunity to acquire the land, building plans, other fees, and application with the City and County for building permits for...

202017231 MLS
195 DOM

76 S Kalaheo Avenue, Kailua $9,250,000

This oceanfront estate offers remarkable views of the world-renowned Kailua beach, while providing a rare opportunity for privacy from beach-goers. With 75 linear ft of p...

6 Beds
5 Baths
202012839 MLS
220 DOM

952 Mokulua Drive, Kailua $6,625,000 ▲

Paradise found! Magically situated on the widest section of Lanikai Beach directly across from the world famous Mokulua Islands, this gated beachfront estate is overflow...

5 Beds
5 Baths
202014172 MLS
223 DOM

Lopaka Way Unit 5, Kailua $2,740,000

Paradise found. Developers have designed house-lot packages & general contractors' avail. to consult w/ to customize your new home. All high-end homes to be built w/ est...

3 Beds
4 Baths
202013915 MLS
228 DOM

42-100 Old Kalanianaole Road Unit 15, Kailua image

42-100 Old Kalanianaole Road Unit 15, Kailua $1,788,000

Presenting spectacular 2 acre parcel in Olomana Heights. Prime ridge top location is ready for your dream home. Enjoy sweeping panoramic views from the lush Koolau mounta...

202011817 MLS
242 DOM

Lopaka Place Unit 6, Kailua $2,530,000

Paradise found. Developers have designed house-lot packages & general contractors’ avail. to consult w/ to customize your new home. All high-end homes to be built w/ est...

4 Beds
4 Baths
202011000 MLS
256 DOM

Lopaka Way Unit 2, Kailua $2,475,000

Paradise found. Developers have designed house-lot packages & general contractors’ avail. to consult w/ to customize your new home. All high-end homes to be built w/ est...

4 Beds
3 Baths
202010998 MLS
256 DOM

122 Lanipo Drive, Kailua $3,450,000

LANIKAI BEACH HOUSE 30 Steps from the Ocean! Ready to live your best beach life ever? The perfect house for people who love the beach. Recently remodeled in 2019. Featur...

5 Beds
5 Baths
202007857 MLS
278 DOM

61 Kaikea Place, Kailua $3,195,000

Large modern home located on one of Beachsides most private streets. Owners on Kaikea Pl. covet the quietness of this well-maintained street with only 8 homes. Completel...

4 Beds
3 Baths
202008141 MLS
285 DOM

12 Kailua Road, Kailua $5,400,000

Quintessential Kailua Beach location and cottage with 143' sandy beach frontage. Personalize the half acre into an estate or create multiple lots. Terrain and zoning p...

202007249 MLS
298 DOM

12 Kailua Road, Kailua $5,400,000

Quintessential Kailua Beach location and cottage with 143' sandy beach frontage. Personalize the half acre into an estate or create multiple lots. Terrain and zoning p...

3 Beds
2 Baths
202007248 MLS
298 DOM

140 Kailuana Loop, Kailua $2,995,000

Live on one of the most desired Beachside neighborhood streets. Right across the street from Kailua beach (ranked one of the top beaches in the world) with a private gate...

4 Beds
4 Baths
201935904 MLS
368 DOM

1345 Lopaka Place, Kailua $2,100,000 ▼

Beautiful home at the highest point in the peaceful Maunawili Valley. The home has 5 bedrooms and 2.5 baths, with panoramic mountain views. Home offers an updated master ...

5 Beds
3 Baths
201935748 MLS
387 DOM

000 Kalanianaole Highway, Waimanalo image

000 Kalanianaole Highway, Waimanalo $598,000 ▼

20,000 level Kuleana (owner does not need to have Hawaiian ancestry) Lot allows for 1 residential home. Excellent exposure on Kalanianaole Hwy across Shima's Market and 7...

201929315 MLS
471 DOM

0000 Kalanianaole Highway, Waimanalo image

0000 Kalanianaole Highway, Waimanalo $398,000 ▼

Kuleana Lot(do not need to have Hawaiian ancestry to buy/own)allows for 1 residential home. Property located just off Kalanianaole Hwy. Address not yet assigned. Access ...