Kissimmee’s commercial real estate market is heating up like never before and a long-vacant property could soon become the city’s newest showpiece.
Three major developers - Skyview Companies, Wendover Housing Partners, and Capstrata/Hedrick Brothers, have submitted proposals to transform the former Kmart and Big Lots site on W. Vine Street into a vibrant, walkable, mixed-use destination. The 22-acre property could soon be home to a thriving neighborhood with shops, restaurants, residential communities, and even waterfront amenities.
The Vision: From Asphalt to a Walkable Waterfront Community
Each proposal centers around the idea of blending residential living with retail, dining, and green spaces, but the scale and style vary.
Skyview Companies
Skyview’s $325 million plan reimagines the site with:
900+ residential units
84,000 sq. ft. of commercial space
A waterfront plaza designed to be the heart of the community
Tree-lined streets, bike lanes, and wide sidewalks for walkability
Phased development, including a flagship waterfront restaurant and 31 townhomes overlooking the lake
10% of units reserved as affordable housing
Wendover Housing Partners
Known for its expertise in mixed-income communities, Wendover’s $140 million concept features:
328 rental units
66,000 sq. ft. of retail and commercial space
Transit-friendly design
A strong focus on affordability and community integration
Capstrata/Hedrick Brothers
While their full plans remain under wraps, Capstrata promises a bold, market-responsive vision with a strong focus on Kissimmee’s long-term community needs.
A City on the Rise
This redevelopment is just the latest in a wave of investment in downtown Kissimmee, with new hotels, residential projects, and commercial developments reshaping the city’s skyline.
Recent highlights include:
Mosaic Apartments at Lakefront Park
The Allen Apartments on the Beaumont site
Planned boutique hotel & condo-loft project at Toho Square
A luxury 200-room hotel and convention center coming to the Civic Center site
Kissimmee Development Services Director Craig Holland says the city’s transformation is finally catching the attention of developers and hoteliers alike, after years of limited interest.
What This Means for Kissimmee’s Real Estate Market
For homebuyers, investors, and business owners, Kissimmee is quickly becoming one of Central Florida’s most dynamic markets. The former Kmart site is poised to become a high-demand address, surrounded by shopping, dining, and entertainment, with the added bonus of waterfront living.
As these projects move forward, property values and demand in the downtown Kissimmee area are expected to rise, making now an excellent time to explore opportunities.
📲 Thinking about buying, selling, or investing in Kissimmee?
Let 20+ years of real estate expertise help you make the right move.
Contact me today:
📧 [email protected]
📞 321-333-1338
🌐 www.vacayreflorida.com