The Oaks Homes for Sale

About The Oaks Neighborhood

The Oaks is a large-scale gated community situated in the Pleasant Hill area of southwest Kissimmee, accessible from John Young Parkway (US-17/92) via The Oaks Boulevard. Developed in multiple phases beginning in 1996 and continuing through 2021, this golf community encompasses over 1,000 homesites spread across three distinctive sub-neighborhoods: Eagle's Nest, Osprey Cove, and Shingle Creek Reserve. The community's defining feature is its integration with the championship Oaks National Golf Club, an 18-hole public course originally designed by Karl Litten and Gary Player in 1986 and completely renovated in 2015.

National builders including Taylor Morrison, KB Homes, Park Square Homes, D.R. Horton, Standard Pacific, Landstar Homes, and Apex contributed to the community's diverse housing inventory. Single-family homes range from approximately 1,000 to 4,580 square feet, offering two to six bedrooms with two to five bathrooms. Many homes feature private pools, golf course views, pond frontage, and conservation-area backdrops. The Shingle Creek Reserve section includes select properties with direct boat access to Lake Tohopekaliga, one of America's premier bass fishing destinations.

Residents enjoy an impressive array of on-site amenities: the community boat ramp provides Lake Toho access for fishing, boating, and watersports; tennis and pickleball courts serve racquet sport enthusiasts; a full basketball court, two playgrounds, a dog park, barbecue areas, and walking and jogging trails round out the recreational offerings. The clubhouse features The Oaks Cafe, a casual restaurant serving golfers and residents alike with food, coffee, and beverages including beer, wine, and cocktails.

The Oaks Location & Connections

The Oaks is located in the Pleasant Hill area of southwest Kissimmee, with its entrance on The Oaks Boulevard off John Young Parkway (US-17/92). This central position provides direct access to US-192 (Irlo Bronson Memorial Highway) to the north and Pleasant Hill Road to the south, connecting residents to The Loop shopping center, downtown Kissimmee, and the broader Orlando metro area. The Florida Turnpike and SR-417 are easily accessible for regional commuting.

The Oaks Amenities & Lifestyle

Life in The Oaks revolves around its championship golf course, lake access, and an unusually broad amenity set for a community of this size. The gated entry and 24/7 security provide privacy and peace of mind, while the mature oak tree canopy and landscaped green spaces create a resort-like atmosphere throughout the community. With over 1,000 homes, the community supports an active social calendar, and the on-site restaurant at the golf clubhouse serves as a natural gathering spot for residents.

Beyond the gates, The Oaks benefits from a central Kissimmee location with Pleasant Hill Commons shopping center directly across John Young Parkway, putting Publix, restaurants, and everyday services within a two-minute drive. The Loop on John Young Parkway provides major retail and dining options just minutes north.

How The Oaks Compares

The Oaks occupies a unique position in the Kissimmee market as an established golf community with an exceptional amenity set. While newer master-planned communities like Storey Creek and Tohoqua offer modern construction, The Oaks delivers a mature tree canopy, established landscaping, a proven clubhouse and restaurant, and the rare combination of championship golf and Lake Toho boat access in one gated community.

The Oaks HOA & CDD Information

The Oaks is governed by a mandatory homeowners association that maintains the community's gated entry, security, common areas, landscaping, roads, and recreational amenities. The community also falls within the Overoaks Community Development District (CDD), an independent special-purpose government entity that finances and maintains community-wide infrastructure. HOA fees vary by sub-neighborhood — Eagle's Nest, Osprey Cove, and Shingle Creek Reserve may each carry different fee structures reflecting their specific amenity access.

The HOA permits pets with certain breed and size restrictions, and dogs and cats are allowed. Architectural standards maintain the community's curb appeal, and golf cart use is permitted within The Oaks for accessing community amenities and recreational areas.

Frequently Asked Questions