Winder Oaks Homes for Sale

About Winder Oaks Neighborhood

Winder Oaks is a small, cohesive neighborhood of 14 single-family homes in Dr. Phillips, tucked just off Conroy Windermere Road in the 32819 zip code. The entire community occupies a single street — Oak Chase Court — giving it a private, enclave-like character rarely found in suburban Orlando. Builder Kelly Concepts Inc. constructed the homes between approximately 2001 and 2006, bringing a contemporary Florida architectural sensibility to a neighborhood that sits precisely between South Kirkman Road to the east and Turkey Lake Road to the west.

Homes in Winder Oaks are Florida-style single-family residences offering 3 to 5 bedrooms with 2-car garages, ranging from approximately 2,300 to 4,000 square feet of living space. Typical lots are approximately quarter-acre in size. Interiors often feature bonuses like formal dining and living rooms, great rooms, and inside utility rooms — floor plans that deliver practical family-friendly functionality in a well-finished, 21st-century build. Block and stucco construction with shingle roofing reflects the durable, low-maintenance character typical of quality Central Florida construction from this era.

While the neighborhood itself has no internal amenities, residents effectively gain access to a full recreation campus courtesy of Shadow Bay Park, which sits just around the corner and is genuinely walkable. The park's facilities — tennis courts, basketball courts, a baseball diamond, sand volleyball, nature trails, and picnic areas — more than fill the role that a community amenity center would otherwise serve, and at no cost to homeowners beyond the park's public access. Multiple shopping plazas with groceries, dining, and services are also within walking distance of the neighborhood, making this location unusually self-sufficient for daily needs.

Winder Oaks is positioned in the heart of the Dr. Phillips entertainment corridor: Universal Studios Florida is approximately 1–2 miles away, and the neighborhood's access to Interstate 4 and the Florida Turnpike makes the entire metro Orlando area reachable with ease. For buyers seeking a newer construction home in an established Dr. Phillips address, with park access, proximity to top-rated schools, and minimal neighbors, Winder Oaks represents a highly functional and uncommon option in the market.

Winder Oaks Location & Connections

Winder Oaks is located in the eastern portion of Dr. Phillips, off Conroy Windermere Road in the 32819 zip code. South Kirkman Road runs directly to the east of the neighborhood and Turkey Lake Road directly to the west, giving Winder Oaks residents quick access to major arterials that connect to Interstate 4, the Florida Turnpike, and the broader Orlando metro in any direction.

The neighborhood's eastern positioning within Dr. Phillips makes it one of the closest residential addresses in the community to Universal Studios Florida and the International Drive corridor. At the same time, the Kirkman Oaks Shopping Center is within very close proximity, providing everyday grocery, dining, and service needs immediately at hand. Palm Lake Elementary School, Chain of Lakes Middle School, and Dr. Phillips High School are all accessible within a short drive, completing a location that delivers genuine convenience without sacrificing the residential calm of a private, 14-home street.

Winder Oaks Amenities & Lifestyle

Living in Winder Oaks offers a lifestyle defined by genuine privacy and walkable recreation within one of the most entertainment-rich corridors in all of Central Florida. Fourteen neighbors, a single quiet street, and no through traffic create a residential experience that feels like a private enclave — while Shadow Bay Park steps around the corner delivers the full recreational amenity set most communities can only offer internally.

The broader Dr. Phillips community surrounds Winder Oaks with the resources that make this one of Orlando's most desirable addresses: over 150 restaurants on Restaurant Row at Sand Lake Road, world-class fitness and aquatics, access to the Butler Chain of Lakes, and proximity to theme parks that make weeknight and weekend entertainment as easy as a short drive — or for Universal, a walk.

How Winder Oaks Compares

Winder Oaks occupies a specific niche in the Dr. Phillips market — newer construction (2001–2006) with Florida-style architecture, no CDD fees, and a uniquely intimate scale of just 14 homes. For buyers who want post-2000 construction quality in an established Dr. Phillips address without the scale or ongoing assessments of larger master-planned communities, Winder Oaks presents a compelling and uncommon option.

Winder Oaks HOA & CDD Information

Winder Oaks has a mandatory Homeowners Association that manages deed restrictions and community standards for the neighborhood's 14 homes. Given the intimate scale of the community, the HOA functions as a straightforward governing body focused primarily on maintaining the neighborhood's appearance standards and shared responsibilities rather than managing extensive common amenities.

There is no CDD (Community Development District) fee in Winder Oaks. This is a meaningful distinction from many newer master-planned communities in Central Florida where CDD assessments can add substantial annual costs to homeownership over the life of the bond.

Frequently Asked Questions