Bailey Dempsey

Bailey Dempsey

REALTOR® / Licensed Real Estate Agent at Keller Williams Classic Group
Florida Real Estate: 3306079
  •   5   (39 reviews)

About Bailey

Bailey Dempsey is your premier resource for selling, buying and investing in southwest Florida real estate. She will guide you in creating the lifestyle you want with the budget you have. As a licensed Realtor®, high standards are the cornerstone of her business. Her leadership through the over 80+ steps it takes to sell and buy a home are testimony to her professionalism and integrity. Bailey specializes in Resort and Second Home Properties (RSPS Certified) as well as helping Seniors transition (SRES Certified),along with being a Probate Real Estate Specialist (CPRES) for your loved ones. Bailey has connections locally, regionally and internationally to help facilitate your real estate needs. If she is not the best agent to assist you, she will put you in touch with professionals she knows you can count on to answer your questions. Please refer to the many 5-Star testimonials about her valuable service. You may contact her at Bailey.Dempsey@KW.com or call 941-404-5310.

Bailey's reviews

  5  
Bailey has 39 reviewsacross 18 different locations, showing 6.
Review Bailey
about 3 years ago
Wonderful

Bailey was professional and very helpful. She was so patient with me and taught me a lot about the real estate market

over 3 years ago
Working with Bailey was a breeze

Working with Bailey was a breeze. We identified our needs and wants prior to arriving in the area. She immediately set us up for notices of new homes that came on the market to further refine what we were looking for. When we arrived - we had identified approximately 8 - 10 homes that we wanted to look at. We identified three homes, and got our first choice! We submitted an offer and it was accepted. During the inspection process and rewalk - we were still out of state and Bailey kept us informed with on-site reporting and video. From start to finish - we felt we were in great hands all the way! Keith and Betsy

over 3 years ago
Great Experience

Bailey was very professional at all times. She remained calm and was patient throughout the process, and gave her time generously to meet our needs before and after closing. I highly recommend her.

almost 4 years ago
Very professional

Bailey is all about costumer service, follows through to the end …

almost 4 years ago
Smooth and painless experience

Bailey Dempsey made selling my house easy for me. She communicated often and kept me up to date with what was happening. Even when I moved out she went beyond what I expected.

Show all 39 reviews

Bailey's properties

Bailey has 1 property for sale and sold 5 properties in the last 12 months, showing 4, sorted by most recent activity

SoldJun 12, 2026
$480,000
5945 Beaconpark Street
Fish Hawk FL 33547
4
4
2
Single-Family
Listing courtesy of EATON REALTY,LLC and Keller Williams Classic Group
SoldApr 30, 2026
$305,000
4641 La Jolla Dr
Bradenton FL 34210
3
2
2
Villa
Listing courtesy of Keller Williams Classic Group and Marcus & Company Realty
SoldApr 2, 2026
$150,000
203/5500 Longwood Run Boulevard
Sarasota FL 34243
2
2
Condo
Listing courtesy of Keller Williams Classic Group
SoldJan 29, 2026
$1,835,000
910/5880 Midnight Pass Road
Siesta Key FL 34242
3
2
1
Condo
Listing courtesy of KELLER WILLIAMS ON THE WATER S and Keller Williams Classic Group
Show all 6 properties
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