Oak Park Homes with Cottage Architectural style

Welcome to Oak Park, a charming subdivision nestled in the heart of Florida, where tranquility meets timeless elegance. Oak Park is not just a neighborhood; it’s a vibrant community that offers a perfect blend of suburban serenity and convenient access to the lively attractions of the Sunshine State. With its tree-lined streets, well-maintained parks, and friendly neighbors, Oak Park is a haven for families, retirees, and everyone in between.

One of the standout features of Oak Park is its stunning homes, many of which showcase the enchanting Cottage Architectural style. These homes exude warmth and character, characterized by their cozy facades, inviting porches, and intricate details that harken back to a simpler time. Each cottage is a unique masterpiece, often adorned with charming shutters and lush gardens that create a picturesque setting. The Cottage style is not just about aesthetics; it embodies a lifestyle of comfort and connection, making it the perfect choice for those who appreciate the art of living well.

Residents of Oak Park enjoy a close-knit community atmosphere, where neighbors become friends and local events foster a sense of belonging. With easy access to shopping, dining, and recreational activities, Oak Park offers the ideal balance of relaxation and engagement. Whether you’re taking a leisurely stroll through the neighborhood or hosting a gathering in your garden cottage, life in Oak Park is nothing short of delightful.

If you’re searching for a place to call home that combines charming architecture with a welcoming community spirit, look no further than Oak Park. Your dream cottage awaits!

Newest Oak Park Homes with Cottage Architectural style

$289,000

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

Virtually Staged. **SELLER SAYS SELL! REDUCED PRICE!!! WELCOME TO 321 CASSADY Street & 20 N OAK Avenue — TWO ADDRESSES, TWO LIVING SPACES, ONE UNIQUE PROPERTY! *MOTIVATED SELLER* 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

$229,000

2 Beds ⋅ 1 Baths ⋅ Oak Park SubDv. ⋅ 32609 Zip Code

Character, charm, and a location you’ll love. This adorable cottage bungalow has been completely updated while preserving the details that give it so much character. The original parquet floors were refinished, with LVP added only where needed, keeping the home’s original feel while giving the spaces a fresh look. The kitchen is straight out of a magazine, featuring new cabinetry and countertops, floating shelves, stainless steel appliances, a cozy breakfast nook, and a custom-built kitchen bench. Major updates include new windows, a new mini-split HVAC system, a metal roof, and a newer water heater. Outside, the landscaping has been thoughtfully done to create a beautiful setting around the home, with space for gardening, outdoor projects, or simply enjoying the yard. The fully covered front porch gives you plenty of room to sit back with your morning coffee or enjoy the afternoon breeze. And the location is hard to beat. Tucked right behind one of Gainesville’s favorite donut shops, Baloo Donuts, you’re less than a 10-minute drive from UF, downtown Gainesville, Shands, the VA, and major hospitals. Cute, updated, full of character, and close to just about everything you need this is one you’ll want to see.

807 Nw 24th Avenue, Gainesville

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