Oakland Park Homes for Sale
A master-planned lakefront community with trail access and green certification standards.
Homes for sale in Oakland Park
Inside Oakland Park
Oakland Park is a master-planned residential community located in Winter Garden, Orange County, built between 2008 and 2025. Developed by Crescent Communities LLC with homes constructed by Ashton Woods, David Weekley, and J & J Building, the community blends contemporary design with environmental stewardship. All homes are built to Florida Green Building Council certification standards, reflecting a commitment to sustainable living.
The community spans 1,584 to 5,600-plus square feet, offering diverse floor plans in architectural styles including Colonial Revival, Victorian, Craftsman, Spanish Colonial, and Florida Vernacular. Homes have sold at an average price of approximately $1.2 million, with recent transaction data showing a 98 percent list-to-sell ratio and 54 days average time on market. HOA fees range from $608 to $1,202 monthly, including common area and grounds maintenance, pool access, and recreation facilities.
Oakland Park benefits from direct access to the West Orange Trail, a 22-mile preserved corridor ideal for cycling and walking to nearby downtown Winter Garden. The community sits between two significant lakes, Lake Brim and Lake Apopka-offering residents water-oriented recreation. Community amenities include a pool, cabanas, fitness center, playground, and picnic areas designed for family gatherings and neighborhood connectivity.
The subdivision appeals to buyers and active adults seeking newer construction in a connected neighborhood. Proximity to major highways, the 408 and 429-provides convenient access to Orlando while maintaining the quieter character of Winter Garden. Buyers should contact a Market Connect Realty agent for current school zoning information, as this varies by lot location within the subdivision.
The facts
Frequently asked
What is the price range for homes in Oakland Park?
Homes in Oakland Park typically range from $675,000 to $2,098,000. Recent market data shows an average selling price near $1.17 million, with homes averaging $277 per square foot. Price variations depend on floor plan, builder, lot location, and interior finishes. Contact a Market Connect Realty agent for current listings.
Is Oakland Park a gated community?
Oakland Park is not a gated subdivision, though some individual properties or micro-communities within may have gated access. The overall community is open-access with connections to the West Orange Trail and public roadways. Verify with your agent if specific gated sections exist.
What schools are zoned for Oakland Park?
Oakland Park is located in Orange County and falls under Orange County Public Schools. School assignments vary by address within the subdivision. Contact the Orange County Schools district or a Market Connect Realty agent to confirm exact elementary, middle, and high school assignments for your specific lot.
What are the HOA fees in Oakland Park?
HOA fees in Oakland Park range from $608 to $1,202 per month, depending on the home. Fees cover common area maintenance, grounds maintenance, building maintenance, community pool access, real estate taxes for common areas, property insurance, and recreation facilities. Some homes may have lower ranges; verify with your builder or agent.
What amenities does Oakland Park offer?
Oakland Park amenities include a community pool, cabanas, fitness center, playground, and picnic areas. The subdivision has direct access to the West Orange Trail, a 22-mile preserved trail system perfect for biking and walking to downtown Winter Garden. Lake Brim and Lake Apopka are nearby for water recreation.
How many homes are in Oakland Park?
The exact total number of homes in Oakland Park is not publicly confirmed, though recent market data shows 8 homes actively listed for sale. The community continues development through 2025. Contact a Market Connect Realty agent for the most current home count and build status.
Is short-term rental allowed in Oakland Park?
Short-term rental policies in Oakland Park are not clearly documented in available sources. HOA rules may restrict or allow vacation rentals depending on specific deed restrictions and covenants. Verify directly with the HOA or your purchase agreement before investing.
What year was Oakland Park developed?
Oakland Park was developed between 2008 and 2025 by Crescent Communities LLC. Homes were built by Ashton Woods, David Weekley, and J & J Building. Development is ongoing as of 2025, with new construction continuing in phases.