Osceola Heights Homes with Rain Gutters Exterior Features

Osceola Heights Homes with Rain Gutters Exterior Features

Welcome to Osceola Heights, a charming subdivision nestled in the heart of Winter Park, Florida, within Orange County. This delightful community is known for its picturesque streets, friendly neighbors, and a welcoming atmosphere that makes it feel like home from the moment you arrive.

Osceola Heights boasts a variety of beautifully designed homes, each with its unique character and style. One standout feature of many residences in this subdivision is the presence of rain gutters, which not only enhance the aesthetic appeal of the properties but also serve a practical purpose. These exterior features help manage rainwater effectively, directing it away from your home’s foundation and landscaping, thereby protecting your investment and ensuring a dry, well-maintained environment.

Residents of Osceola Heights enjoy the perfect blend of suburban tranquility and urban convenience. The subdivision is conveniently located near Winter Park's vibrant downtown area, where you can explore an array of boutique shops, exquisite dining options, and cultural attractions, including art galleries and parks. Families will appreciate the proximity to highly-rated schools and recreational facilities, making it an ideal place for raising children.

Whether you’re a first-time homebuyer or looking to settle into a peaceful community, Osceola Heights offers a delightful living experience. With its charming homes, excellent amenities, and friendly community spirit, it’s no wonder that this subdivision is a sought-after destination in Winter Park. Come discover the warmth and charm of Osceola Heights, where your dream home awaits!

Newest Osceola Heights Homes with Rain Gutters Exterior Features

$589,900
3 Beds 3 Baths Osceola Heights SubDv. 34654 Zip Code
If you've been searching for a home with some land, storage, an outdoor kitchen and a saltwater pool then this is it. No HOA, no CDD fees, and not in a flood zone. Sitting on nearly 2 acres, this property features a new 30x50x20 metal building built in 2025 with a concrete floor and four roll-up doors — including a 14-foot door and three 12-foot doors — making it ideal for a contractor, car enthusiast, or anyone who needs serious space to work and store equipment. And when the workday is done, you've got a great 3-bedroom, 2.5-bath home with a saltwater pool waiting for you. Inside, you'll find no carpet anywhere. Ceramic tile runs through all the main living areas, kitchen, and bathrooms, with laminate flooring in each bedroom. The kitchen has been updated with newer cabinets and LG stainless steel appliances. All three bedrooms are well-sized with walk-in closets. The primary suite features a walk-in shower, while the secondary bath offers a tub/shower combo. The indoor laundry room is generously sized, and the home includes a whole-house water filtration system. Out back, a large, covered patio leads to an outdoor kitchen with a wood/charcoal pizza oven — great for entertaining. The screened, in-ground saltwater pool has a newly replaced saltwater cell and is enclosed by a pool cage. There's also an outdoor half-bath conveniently located poolside. For storage and workspace, the property really stands out. A 30x50x20 metal barn with a concrete floor and four roll-up doors — one 14-foot and three 12-foot — gives you room for equipment, RV, vehicles, or whatever your needs call for. A secondary outdoor workshop adds even more utility. The well and bladder tank were both replaced in 2025. This is a solid, move-in ready home with the kind of outdoor space and infrastructure that's hard to find.

10744 Osceola Drive, New Port Richey

$1,225,000
3 Beds 3 Baths Osceola Heights SubDv. 32789 Zip Code
This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.

1870 Walker Avenue, Winter Park

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