By Jim Carchidi
January 19, 2026
The series of high-profile commercial transactions in downtown Winter Garden is larger by one with the $6.5 million purchase of 100 W. Plant St. The sale includes the attached property at 126 W. Plant St., currently leased by Black Bean Deli.
The Numbers
The sale of 100 W. Plant Street is the latest of five commercial property sales in downtown Winter Garden over five months. Photo courtesy of Kari Fleck
The off-market transaction closed on December 30, one day before the $4 million sale of two condominium units and 8,000 square feet of commercial space at 2 W. Plant St.
Additional downtown sales over the past five months include:
- Tremaine Boyd building, 109 S. Boyd St.: Sold January 5 for $10.4 million
- Allen & Company office space, 16 E. Plant St.: Sold November 21 for $2.3 million.
- Edgewater Hotel, 99 W. Plant St.: Sold in August for $10.3 million
The Appeal
The building at 2 W. Plant Street includes Three Birds Cafe and Polka Dotz Boutique. Photo courtesy of Josiah Moore
Millenia Partners represented the sellers of the 16 E. Plant St., Edgewater Hotel, and 100 W. Plant St. properties. Sales associate Josiah Moore, who represented the 100 W. Plant St. landlord, told The Orlando Real the factor that seems to be placing Plant Street so high on commercial real estate wish lists is walkability.
“After Covid, high street retail has become the future and Plant Street fills the void,” he said.
Moore also cites Plant Street’s potential for maximum profitability, driven by the “invaluable underlying real estate.”
“The trade-off for location is often low returns,” he said. “On the other hand, Plant Street offers stability, immediate growth, and location. Not to mention that retail/office vacancy is non-existent and demand is high, leaving landlords with all the cards.”
The Competition
According to Crexi, the average office lease in Winter Park’s 32789 zip code, which includes Park Avenue, is $41 per square foot. Retail leases in the same zip code average $44 per square foot. In Plant Street’s 34787 zip code, office space averages $33 per square foot with retail at $35 per square foot.
The History
Several Plant Street buildings are historic, like The Edgewater hotel, which dates back to 1927. Photo by Jim Carchidi
Winter Garden’s charm and history attracts residents, families, and tourists searching for a day of local flavor. The 100 W. Plant Street building dates back to 1947 and formerly housed a First National Bank branch before transitioning to retail and office space in the early 2000s. The building currently features marquee tenant, The Real Estate Collection, along with custom boat dock company, Q-ICE Builders, a mortgage lender, and a title company.
Nearby historic buildings include: the Edgewater Hotel at 99 W Plant St., built in 1927; The Cappleman Building at 121 W. Plant St., built in 1921; and the former Pounds Motor Company building at 162 W. Plants Street, built in 1926.
The Neighbors
The Plant Street vibe is enhanced by longstanding local businesses, like Axum Coffee, Urban on Plant, and Chef’s Table at the Edgewater. Hangry Bison, at 250 W. Plant St., was among the first corporate tenants to make an entry. As more are likely to be attracted by the current market, city leaders and landlords seem to be on the side of small business.
“I don’t think we’re to a point where base rents are excluding regional operators,” Moore said. “Anybody can buy a Starbucks on a retail thoroughfare but not everyone can buy a historic, long-term building where the real estate will appreciate and you’re actually going to come visit with your kids and your family. That’s what Plant Street is.”
Sponsor: The Orlando Real is sponsored by the Pozek Group — the #1 real estate team in Orlando and the Official Real Estate Team of the Orlando Magic.
About the Author
Jim Carchidi is an Orlando journalist and photographer with previous work at the Orlando Sentinel and Orlando Business Journal. He covers development, arts, culture, and local stories for The Orlando Real.
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