Oak Park Homes with Sidewalk Exterior Features

Welcome to Oak Park, a charming subdivision nestled in the heart of Orlando, Florida. This picturesque community is located in Orange County, offering residents a perfect blend of suburban tranquility and urban convenience.

One of the standout features of homes in Oak Park is the sidewalk exterior design. True to its promise, Oak Park boasts a network of sidewalks that not only enhance the aesthetic appeal of the neighborhood but also provide a safe and convenient environment for residents to stroll, jog, or walk their pets.

With tree-lined streets and well-maintained sidewalks, Oak Park is a pedestrian-friendly enclave where neighbors can connect and enjoy the outdoors. Imagine taking a leisurely evening walk or a morning run while soaking in the beauty of the surroundings.

In addition to its sidewalk features, Oak Park is known for its diverse range of home styles, from cozy bungalows to spacious family homes. Whether you're a first-time buyer or looking to upgrade to your dream home, Oak Park offers a variety of options to suit your lifestyle and preferences.

Experience the best of Orlando living in Oak Park, where sidewalks lead to community parks, local amenities, and a vibrant neighborhood atmosphere. Come and discover why Oak Park is not just a place to live, but a place to call home.

$349,000

2 Beds ⋅ 2 Baths ⋅ Oak Park SubDv. ⋅ 32784 Zip Code

Virtually Staged. WELCOME TO 321 CASSADY Street & 20 N OAK Avenue — TWO ADDRESSES, TWO LIVING SPACES, ONE UNIQUE PROPERTY! Discover a truly unique investment opportunity featuring two separate living spaces! The charming front home is a 1920s country cottage, complete with a classic white picket fence and plenty of character, while the rear of the property features a beautifully renovated garage apartment/ADU with its own separate address, electric meter, and water meter—an excellent setup for extended family, guests, or potential rental income. The main cottage offers 2 bedrooms and an inviting open great room and kitchen, filled with the warmth and character you would expect from a vintage country home. Relax on the large screened front porch, the perfect spot for morning coffee or an evening spent enjoying the Florida breeze. Step into the private, fully fenced backyard and you'll find even more to love. A charming KOI pond filled with fish creates a peaceful outdoor setting, while a cement walkway connects the main cottage to the rear apartment. There is plenty of space for entertaining, hobbies, storage, and all your Florida toys! The rear building offers a workshop beneath the ADU, plus there are two additional newer storage sheds, including one with an awning providing covered parking for a boat or golf cart. You'll also find a concrete RV pad alongside the garage. The garage apartment/ADU was completely renovated in 2025 and provides a separate living area with its own utilities and address—making this property especially versatile. MAJOR UPDATES INCLUDE: Electrical – 2025 Plumbing – 2025 Garage Apartment/ADU Completely Renovated – 2025 Metal Roof on Garage/ADU 2019 Shingle Roof on the 1920s Cottage Updates Have Been Permitted Whether you're looking for a multi-generational property, income-producing opportunity, guest quarters, or simply extra space, 321 Cassady & 20 N Oak offer possibilities that are hard to find. Two addresses, separate utilities, two living spaces, workshop and extensive storage—all on one unique property! Please note stove will be replaced prior to closing.

321 Cassady Street, Umatilla

Oak Park Homes with Sidewalk Exterior Features

Newest Oak Park Homes with Sidewalk Exterior Features