Ashley Bailey's Profile Photo

Ashley Bailey

REALTORĀ® | RB-23483

Revenue

$80M+

Awards

Real Producer's Magazine October Cover Girl & Featured Agent - Top 150 Agents in Hawaii
Pacific Edge Magazine's "Best Real Estate Agent of the Year Business Achievement Awards" Winner 2024 
Tom Ferry & Real Trends 2023 "America's Best List" ranked #146/12,000+ licensed Realtors on Oahu
Top 1.5% out of 1.8M licensed Realtor's Nationwide
Pacific Edge Magazine's "Best Real Estate Agent of the Year Business Achievement Awards" top 3 finalists, 2022 & 2023
Honolulu Magazine's "Best in Real Estate" 2021, 2022 
Aloha 'Aina Realtor Awards Nominee 2019, 2020, 2021, 2022, 2023, 2024, 2025
Two episodes on HGTV's "Hawaii Life" - Season 14 & Season 10 
"Best of Zillow" - Top Premier Agent

Specialties

Expert negotiator, luxury listing agent, luxury buyer specialist, real estate investment strategies, military PCS + relocation services, staging.

Education

University of Massachusetts - Business Marketing

Charity

Hawaii Yacht Club Member- Chair of Membership & Marketing 2018-2021
Friends of Italy Society of Hawaii Board member 2017-2019
HILT - Hawai'i Land Trust 
Elks Member
About Ashley
A text banner with the word THE and a group

 Realtor BrokerĀ® | Principal 

Ashley is the principal Realtor-BrokerĀ® and founder of The Bailey Group, she has an outstanding track record in the fast-paced Oahu real estate market and a reputation for results with integrity. With 20 plus years of sales experience as a top producer, over $80 million in residential real estate sales and numerous local industry accolades, her dedication speaks for itself. Ashley is ranked in the top 1.5% out of 1.8M realtors in America. Ashley works diligently for her clients, and if you like a person who is responsive, driven, dependable and a strong negotiator, she is the agent for you.

Ashley is originally from Boston but has lived on Oahu for over 15 years. She graduated from the University of Massachusetts Dartmouth with a degree in business marketing, and she truly understands creative and effective ways to market and sell homes. Ashley’s focus when working with clients is to not only meet their real estate expectations, but to exceed them, and she always strives to bring them peace of mind throughout the entire transaction.

The Hawai’i real estate market is dynamic, fast paced, and hyper-localized, it’s important to have a local neighborhood expert by your side, and Ashley and her team at The Bailey Group are just that. Whether buying or selling, first-time-homebuyer or savvy investor, she helps clients make informed fact-based decisions. Committing herself to finding the perfect home that fits the client’s lifestyle, needs and dreams is what truly drives her. When Ashley is not matchmaking people with property, she is an avid sailor and member of the Waikiki Yacht Club. She is a dual citizen of Italy and travels there yearly, surfs Queens often and loves hosting dinner parties at her home in Diamond head.

Ashley Bailey’s Listings

a view of a patio with a table and chairs
a view of a dining room with furniture a livingroom and chandelier
a kitchen with stainless steel appliances granite countertop a refrigerator a stove and a sink
a view of a dining room with furniture
a kitchen with stainless steel appliances granite countertop a refrigerator a sink dishwasher stove and oven
a kitchen with stainless steel appliances granite countertop a sink a counter space and a view of living room
a living room with lots of furniture and potted plants
a living room with furniture and a large window
a living room with furniture and a large window
a living room with furniture and a flat screen tv
a backyard of a house with a potted plant
a bedroom with a bed a mirror and desk
a bedroom with a large bed and a large window
a bedroom with a bed and a window
a bedroom with a bed a window and couch
a view of living room with a table and chairs
a living room with furniture and a large window
a view of a dining room with furniture window and outside view
a dining room with furniture and a large window
a dining room with large glass windows and furniture
a living room with lots of furniture and a large window
a living room with furniture kitchen view and a large window
an aerial view of a house with a swimming pool
a view of an outdoor space
$720,000 | 68-615 Farrington Highway, Unit 5B, Waialua, HI 96791
1/25
Listed By Compass

$720,000

1
Bedrooms
792
Square Feet
a kitchen with granite countertop a sink and a stove
a living room with furniture a wooden floor and next to a window
a kitchen with stainless steel appliances granite countertop a stove and a refrigerator
a kitchen with stainless steel appliances granite countertop a sink and a stove
a kitchen with stainless steel appliances a refrigerator and wooden floor
a kitchen with a washer and dryer
a living room with furniture and a book shelf
a view of a dining room with furniture and window
a work room with furniture and a book shelf
a bed room with furniture and a book shelf
a living room with furniture and a flat screen tv
a bedroom with a bed and a flat screen tv
a bedroom with a large bed and a window
a living room with furniture and a large window
a bedroom with a large bed and a large window
a bathroom with a bathtub and a shower
a bathroom with a granite countertop sink a mirror a bathtub and shower
a bathroom with a bathtub and a shower
a view of a room with a window
a bedroom with a bed and a painting on the wall
a bedroom with a bed and wooden floor
a bathroom with a bathtub and a shower
a bathroom with a granite countertop sink mirror and a bathtub
a picture of table sitting on a patio
$715,000 | 1888 Kalakaua Avenue, Unit 907, Honolulu, HI 96815
1/25
Listed By CompassActive Under Contract

$715,000

2
Bedrooms
1,128
Square Feet

Ashley Bailey’s Transactions

Past Sales
an aerial view of a city

$2,050,000

8
Bedrooms
2,332
Square Feet
0.37
Acres
a view of outdoor space with seating

$1,900,000

4
Bedrooms
3,256
Square Feet
0.24
Acres
a house with a yard and a large parking space

$1,680,000

3
Bedrooms
2,001
Square Feet
0.37
Acres
a view of kitchen with furniture and wooden floor

$1,660,000

3
Bedrooms
2,001
Square Feet
0.37
Acres
a view of a house with backyard and sitting area

$1,630,000

4
Bedrooms
2,216
Square Feet
0.23
Acres
a living room with furniture and a wooden floor

$1,550,000

2
Bedrooms
1,561
Square Feet
a living room with furniture and wooden floor

$1,525,000

4
Bedrooms
1,900
Square Feet
0.13
Acres
an aerial view of residential houses with outdoor space

$1,500,000

3
Bedrooms
1,962
Square Feet
0.21
Acres
$1,450,000 | 1 Keahole Place, Unit 2612, Honolulu, HI 96825

$1,450,000

3
Bedrooms
1,999
Square Feet
a front view of a building with a garden

$1,450,000

4
Bedrooms
1,874
Square Feet
0.14
Acres
a front view of a house with garden

$1,400,000

4
Bedrooms
2,016
Square Feet
0.09
Acres
a kitchen with stainless steel appliances granite countertop wooden cabinets a sink and dishwasher

$1,400,000

4
Bedrooms
2,284
Square Feet
0.12
Acres
a living room with furniture and a flat screen tv

$1,365,000

3
Bedrooms
1,447
Square Feet
a kitchen with stainless steel appliances granite countertop a refrigerator a stove cabinets and wooden floor

$1,325,000

7
Bedrooms
1,947
Square Feet
0.16
Acres
a living room with furniture and windows

$1,300,600

3
Bedrooms
1,756
Square Feet
0.34
Acres
an aerial view of a house with a yard

$1,300,000

4
Bedrooms
2,124
Square Feet
0.11
Acres
a front view of a house with a garden and garage

$1,275,000

4
Bedrooms
1,980
Square Feet
0.23
Acres
a view of a house with pool plants and large trees

$1,215,000

4
Bedrooms
2,216
Square Feet
0.23
Acres