Oakland Park
Lakefront luxury with eco-conscious values on Lake Apopka.
Live the MaxLife.
$1.2M
Median Price
$675K – $2.1M
47
Homes
$608–$1202
Monthly HOA
2008
Established
Oakland Park — What's Selling
Recent closed sales in and around Oakland Park, live from the Stellar MLS · about $380/sq ft · aggregates only, no addresses published.
Search Homes for Sale in Oakland Park
First access
Get notified when a Oakland Park home hits the market.
VIP members see new Oakland Park inventory 48 hours before Zillow.
Background
A brief history
Oakland Park was developed beginning in 2008 by Crescent Communities LLC, emerging as one of Winter Garden's most desirable master-planned communities. Built over more than a decade, the neighborhood reflects the evolution of Central Florida luxury home building, with homes constructed by top-tier builders including David Weekley, Dream Finders Homes, Ashton Woods, and Rockwell Homes. The community was intentionally designed around environmental stewardship and lakefront living, capitalizing on its unique position on the shores of Lake Apopka.
The development intentionally preserved the natural landscape and positioned homes to maximize views and access to the lake and adjacent West Orange Trail system. This commitment to eco-conscious planning made Oakland Park stand out in a crowded market of new construction communities. Today, the neighborhood represents the best of modern Central Florida luxury—resort-style amenities, world-class builders, and a mature landscape that appeals to discerning homebuyers seeking both investment and lifestyle.
As of 2026, Oakland Park remains one of Winter Garden's strongest communities, with homes regularly selling in the $675,000 to $2.1 million range and an active HOA that maintains the shared vision of quality and community stewardship.
The feel
What it's like to live here
Oakland Park is where lakefront elegance meets eco-conscious living. Walking through the community, you'll notice mature landscaping, preserve areas, and architectural variety—homes range from 2,448 to 4,573 square feet, yet the neighborhood maintains a cohesive, upscale aesthetic. The homes reflect the builders' craftsmanship, with David Weekley's signature quality alongside Dream Finders' innovation and Ashton Woods' attention to detail.
What sets Oakland Park apart is the water: Lake Apopka views, direct trail access, and proximity to nature create a vacation-like atmosphere for residents. The community clubhouse, resort-style pool, and fitness center draw neighbors together, while the dog park and playground cater to families. The West Orange Trail runs directly through the property, offering miles of walking and biking paths. It's a community where young professionals, established families, and retirees coexist peacefully, unified by a commitment to quality homes and outdoor living.
The details
What to expect
Architecture & Homes
Oakland Park features single-family homes built by prestigious builders between 2,448 and 4,573 square feet. Expect contemporary Floridian and transitional architecture with open floor plans, high ceilings, and outdoor living spaces designed for Lake Apopka views. Many homes feature energy-efficient systems, smart home technology, and premium finishes reflective of the builders' reputation. Lot sizes vary, with some homes offering direct waterfront or water-view premium lots.
Amenities & Lifestyle
Oakland Park delivers resort-style living with a state-of-the-art clubhouse, resort-style pool, fitness center, and pickleball courts. The community includes a dog park, playground, picnic areas, and cabanas. Most notably, homes have direct access to the West Orange Trail, a 22-mile paved multi-use path perfect for walking, jogging, and cycling. The community emphasis on outdoor recreation and eco-conscious design means residents often gather for trail events and community activities.
Schools
Oakland Park is served by highly-regarded Orange County Public Schools: Tildenville Elementary (Pre-K through 5th grade, 0.5 miles away), Lakeview Middle School (6th through 8th grade, 2 miles away), and West Orange High School. Private school options include Windermere Preparatory School nearby. The school system is rated well within Orange County, making Oakland Park attractive to families.
Location & Access
Oakland Park straddles Oakland Park and Winter Garden, positioned on Lake Apopka near the City of Winter Garden's downtown district. SR-429 is about 5 miles south, providing quick access to downtown Orlando (20 minutes), theme parks (25-30 minutes), and airport (35 minutes). The community is nestled between upscale neighborhoods and offers a rare combination of lakefront living with suburban convenience. The West Orange Trail connection makes it easy to reach downtown Winter Garden on foot or bike.
Community
Amenities
- State-of-the-art fitness center
- Resort-style community pool
- Clubhouse with meeting spaces
- Pickleball courts
- Dog park
- Playground
- Direct West Orange Trail access
- Lake Apopka waterfront
- Picnic areas
- Cabanas
- Walking and jogging trails
- Community park
Know Before You Buy
HOA rules worth knowing
- Pets allowed with breed restrictions and quantity limits
- Architectural guidelines for exterior modifications
- Landscape maintenance standards required
- Common area access rules and pool hours
- HOA fee includes common area maintenance, grounds maintenance, community pool, fitness center, recreation facilities, property insurance, and real estate taxes for common areas
- Trash and recycling guidelines
- Vehicle and parking regulations
- Lease restrictions on primary residence (typically one lease per calendar year)
- Community event participation opportunities
Market Commentary
What the market is doing
Oakland Park is one of the strongest pricing markets in Winter Garden. Homes here sold for an average of $1,172,514 last year with asking prices averaging $1,200,000. What makes Oakland Park's pricing remarkable is consistency—homes hold value well because the builders were elite, the lots are generous, and the amenities actually matter. You're not buying a commodity; you're buying David Weekley or Ashton Woods craftsmanship on a Lake Apopka lot with trail access. That's worth real money. I've seen homes appreciate 8-12% annually when market conditions are favorable. The challenge isn't selling Oakland Park homes—it's pricing them to sell in the first 30 days. Oversell by $50,000 and you'll sit 60+ days. Price it right at $1.20 million and you'll likely have multiple offers within three weeks. I focus on data-driven pricing and professional staging to move homes fast in this segment.
Active MLS Inventory
Search homes in Oakland Park
Live MLS search for Oakland Park is coming online shortly.
In the meantime, get notified when a home in Oakland Park hits the market — VIP list members see new Oakland Park inventory 48 hours before it appears on Zillow.
Get Oakland Park AlertsActive MLS Inventory
Homes available in Oakland Park
10 homes currently listed in Oakland Park.
$770,000
931 Kylee Aly
Winter Garden, FL 34787
4 bd · 4 ba · 2,831 sqft
Oakland Park
MLS ID #O6404673
Listing provided by Stellar MLS
$1,725,000
720 Lake Brim Dr
Winter Garden, FL 34787
4 bd · 4 ba · 3,781 sqft
Oakland Park
MLS ID #O6387519
Listing provided by Stellar MLS
$675,000
936 Kylee Aly
Winter Garden, FL 34787
3 bd · 3 ba · 1,772 sqft
Oakland Park
This property is under contract. Contact us for backup offer opportunities.
MLS ID #O6393910
Listing provided by Stellar MLS
$649,000
914 Trowman Aly
Winter Garden, FL 34787
3 bd · 3 ba · 1,642 sqft
Oakland Park
MLS ID #O6410871
Listing provided by Stellar MLS
$1,699,999
1101 Eagles Pass Way
Winter Garden, FL 34787
6 bd · 5 ba · 4,104 sqft
Oakland Park
MLS ID #O6408835
Listing provided by Stellar MLS
$949,000
744 Lake Brim Dr
Winter Garden, FL 34787
4 bd · 4 ba · 2,667 sqft
Oakland Park
This property is under contract. Contact us for backup offer opportunities.
MLS ID #O6388775
Listing provided by Stellar MLS
Want Oakland Park homes first?
Hand-picked Oakland Park matches — 48 hours before MLS. Two to three per month.
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 13, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA