curated
Contemporary Retail
Boutiques, wellness and everyday essentials in a walkable setting made for browsing, not just errands.
A New Shopping Village · Oakland, Florida
Coming Soon
where Oakland comes together
Chef-driven dining, contemporary retail and shaded courtyards are coming to W. Colonial Drive: Oakland’s first shopping village, and a new place for the town to come together.
a real
Third Place Community
Not home, not work, but the place in between: courtyards, shade and seating made for lingering with neighbors.
rooftop & al fresco
Chef-Driven Dining
Rooftop and covered patios, craft concepts and neighborhood favorites, from first coffee to last call.
The First Shopping Village for Oakland, FL
Rooted in History.
Rising for Tomorrow.
Oakland has always had character. Now it will have a new place to come together.
Welcome to the Town of Oakland, Florida, a place where ancient oaks line the roads, a beloved lake shimmers along the southern shore, and an old railroad became one of Central Florida’s most treasured trails. Nestled between Winter Garden and Clermont along the SR-50 corridor, Oakland sits at the heart of one of the fastest-growing communities in the state.
Oakland Village is a new mixed-use destination designed to serve the community Oakland is becoming, without forgetting the town it has always been. Among the shade of the iconic oaks, we are creating a gathering place anchored by first-class retail, chef-driven restaurants, unique boutiques and open green spaces that reflect Oakland’s enduring love of the outdoors.
It is a place where the spirit of the West Orange Trail meets the energy of a growing town, where the legacy of the Orange Belt Railroad finds a new purpose, and where the people who made Oakland one of the most sought-after communities in Orange County finally have a gathering place worthy of their town.
This isn’t just development. This is a homecoming.
Renderings
A first look at Oakland Village
Conceptual renderings of the courtyards, storefronts and gathering places taking shape on W. Colonial Drive.
Site Plan
Laid out for gathering
Nine buildings and two outparcels along W. Colonial Drive and Catherine Ross Road, with restaurant endcaps, a drive-through and courtyards at the center. Every building is divisible.
Zoom in
For the Town of Oakland
What Oakland Village gives back
Oakland Village is designed to add to daily life in Oakland without changing what makes the town special.
A place to gather
Oakland’s first shopping village, and a new place for the town to come together: courtyards, shade and seating where neighbors run into neighbors.
Dining worth the walk
Chef-driven restaurants, rooftop and covered patios, and evenings that last long past sunset.
Shops close to home
Curated boutiques and everyday conveniences minutes from Oakland’s neighborhoods, not miles away.
Arrive your way
Golf-cart parking, bike racks and walkable paths designed around how Oakland already moves.
Rooted in Oakland
Architecture and landscape that honor the town’s oaks, its railroad legacy and its love of the outdoors.
Room for community
Open green space and courtyards that can host markets, music and seasonal celebrations.
a curated mix
Everyday needs, special occasions and everything between
The tenant mix is being curated for the way Oakland lives: farm-to-table dining, dessert and candy, beauty and wellness, medical and fitness, a neighborhood brewery and places simply made for gathering.
- Farm to Table
- Dessert
- Candy
- Beauty
- Medical
- Fitness
- Brewery
- Placemaking
Leasing & More Information
Bring your concept to Oakland Village
Restaurant, retail, service and medical opportunities from 1,260± to 10,805± SF, with endcaps, patios and a drive-through position available.
14.80±Acres, total site
85,000±SF retail & restaurant
9 + 2Buildings + outparcels
16,000±SF patio & amenity areas
Built for the businesses Oakland wants
- Restaurant endcaps with rooftop and covered al fresco dining
- One drive-through position available
- Excellent signage and frontage on W. Colonial Drive (SR-50)
- Tenant-specific upgraded design options
- Golf-cart parking and a bike-friendly site plan
- Courtyards and amenity areas that keep the center active into the evening
- All buildings divisible, from 1,260± SF to 10,805± SF
- Between Winter Garden and Clermont with access to SR-50, SR-429 and Florida’s Turnpike
tenant-specific upgraded
Design options
Location
Between Winter Garden and Clermont, on SR-50
15949 W Colonial DrOakland, FL 34787
West Orange County · Orlando metro
- Frontage on W. Colonial Drive (SR-50) at Catherine Ross Road
- Minutes from Downtown Winter Garden’s dining and entertainment district
- Convenient access to Florida’s Turnpike and SR-429
- Near the West Orange Trail and the Oakland Nature Preserve
- Surrounded by golf-cart-friendly neighborhoods
Contact Us
Tell us who you are
Whether you’re bringing a concept to Oakland Village, covering the story, or counting the days until opening, we want to hear from you.
Potential Tenants
Restaurants, retailers, service and medical concepts: request the leasing package and current availability.
Media
Press inquiries, renderings and project statements.
Future Customers
Neighbors and visitors: get opening news, events and announcements first.