Principal

Drake Dickerson, MSRE, CCIM, ALC

Partner — Land & Commercial · Lifestyle Group at Oceans Commercial

Drake came to brokerage from the buyer’s side of the land business: nearly five years acquiring residential land for national homebuilders. He is based in Winter Park, serving Winter Park and the Orlando metro directly, and works land and commercial sales across Volusia and Flagler with Frank Molnar.

About Drake

Drake Dickerson is Partner, Land & Commercial at the Lifestyle Group at Oceans Commercial. He joined the Lifestyle Group in February 2024 after nearly five years in homebuilder land acquisition, and he now represents landowners, builders, developers, investors and owner-users on land and commercial sales across Central Florida.

His land acquisition career ran through three national homebuilders: Land Acquisition Specialist at Richmond American Homes (MDC Holdings) from 2019 to 2021, then Land Acquisition Manager at Taylor Morrison from 2021 to 2023 and at Meritage Homes from 2023 to 2024. Those are the roles that decide what a parcel is worth to a builder and what has to be true before it closes, and they are the reason a Lifestyle Group land package is assembled the way a builder’s land committee expects to read it: yield, entitlement status, utilities, and the cost and time to finished lots.

On a commercial acquisition or disposition he underwrites the property the way an investment committee would before it goes under contract, and he works with exchange buyers against the 45-day identification and 180-day closing deadlines of a 1031 exchange.

Education and credentials

Drake holds a Master of Science in Real Estate from the University of Central Florida and a bachelor’s degree from UCF with a triple major in finance, economics and real estate. He earned the CCIM designation from the CCIM Institute in 2024 and the Accredited Land Consultant (ALC) designation from the REALTORS® Land Institute in April 2026, and he completed the Master in Commercial Property (MiCP) program at the Lipsey School of Real Estate in 2025. He is a licensed Florida real estate sales associate.

Industry leadership

He is the 2026 President-Elect of the Central Florida Commercial Association of REALTORS® (CFCAR), the 2026 Vice President of Administration of the Florida CCIM Chapter, and the 2026 Secretary of the CCIM Florida Central District.

Published research

Drake is co-author, with R. J. Curcio, of a peer-reviewed study of long-term equity investing with leveraged exchange-traded funds, published in The Journal of Index Investing in 2017.

Citation

Curcio, R. J. & Dickerson, D. R. (2017). “Long-Term Equity Investing with Leveraged Exchange-Traded Funds.” The Journal of Index Investing, 8(2), 23–37. https://doi.org/10.3905/jii.2017.8.2.023 (external site)

Selected transactions

Transactions in which Drake was a principal on the Lifestyle Group side.

Finished lots

Tattersall at Tymber Creek

Ormond Beach

2026

26 homesites · $5.1M+

Phase 1 of a 62-lot commitment for K. Hovnanian Homes

Residential land

Grassmere Reserve

Zellwood, Orange County

2024

153 lots · ±130 AC · $12.4M

Closed with M/I Homes, 50 days from LOI to closing

Downtown commercial

200 S. Beach St

Daytona Beach

2026

$2.8M

Commercial sale, June 2026

Selected transactions completed by Lifestyle Group principals. Figures reflect public records and announcements; details available on request. All selected transactions →

Start a conversation

Talk to a principal about your property.

Land, a building, a site requirement or an exchange deadline — the first conversation is with Frank or Drake, and it is handled with discretion.

Drake Dickerson — Partner, Land & Commercial · (407) 489-4774

Oceans Commercial · Licensed Florida real estate brokerage