Windward Place Real Estate

Welcome to Windward Place, a hidden gem nestled in the heart of Orlando, Florida. This charming subdivision in Orange County offers a perfect blend of suburban tranquility and urban convenience, making it an ideal choice for families, young professionals, and retirees alike.

Windward Place is characterized by its beautifully landscaped streets, where well-maintained homes exude warmth and character. The community showcases a variety of architectural styles, from modern designs to classic Florida ranch homes, ensuring there’s something for everyone. Residents enjoy spacious lots that provide ample outdoor space for gardening, play, and relaxation.

One of the standout features of Windward Place is its close-knit community atmosphere. Neighbors often come together for seasonal events and gatherings, fostering friendships and connections that make this subdivision feel like home. Families will appreciate the nearby parks, playgrounds, and recreational facilities, perfect for weekend outings and outdoor activities.

Convenience is at your fingertips with Windward Place’s prime location. Just a short drive away, you’ll find a myriad of shopping, dining, and entertainment options, from local boutiques to major retail centers. Plus, the vibrant attractions of downtown Orlando and the world-famous theme parks are easily accessible, ensuring you’ll never run out of things to do.

If you’re seeking a serene yet vibrant community that offers the best of Orlando living, look no further than Windward Place. Here, you can create lasting memories in a place that truly feels like home. Come explore all that this delightful subdivision has to offer!

Newest Listings in Windward Place

$535,000

3 Beds ⋅ 3 Baths ⋅ Windward Place SubDv. ⋅ 32812 Zip Code

Virtually Staged. Welcome to 4404 Sailor Court, a turnkey colonial-style pool home offering 3-bedrooms, 2.5-baths, and 1,972 square feet of living space. This home is conveniently situated at the end of a cul-de-sac, features an impressive .30-acre lot, a fully fenced-in backyard, and no rear neighbors. The beautiful brick exterior offers timeless curb appeal, while the tastefully updated interior is warm, inviting, and truly move-in ready. As you step inside, discover the details that make this home special. The custom stairs and laminate flooring (2025) throughout the ground floor, fresh interior paint (2026), and new light fixtures (2026) create a welcoming first impression. On the first floor you'll find the formal dining room, living room, kitchen, a brick wood-burning fireplace, half bathroom, and the laundry room. The kitchen is equipped with a full suite of new stainless steel Whirlpool appliances (2025/2026), granite counter tops, plenty of storage, and upgraded soft close cabinets. Impact windows throughout the home bring in an abundance of natural light. Upstairs, you'll find three generously sized bedrooms, including the oversized primary suite. The guest bathroom is shared by the two additional bedrooms, one of which features a built-in desk system, ideal for a home office. Step outside through the sliding glass doors and you'll find a spacious, covered, screened-in patio. The private screened-in pool, outdoor bar, and expansive backyard create a perfect setting to experience the Florida lifestyle. Enjoy the privacy of having no rear neighbors and a fully fenced-in backyard. Major improvements provide additional peace of mind, including a newer roof and gutters (September 2022), A/C (May 2019), new water heater (2026), new pool pump (2026), and newer septic drain field (2023). Two sheds in the backyard add additional storage options, including a 12x10 Tuff shed (2022). Centrally located near the heart of Orlando, you really can't beat this location! Barber Park is right around the corner which offers basketball courts, soccer fields, playgrounds, a splash pad, dog park, and seasonal farmers markets. The home is just minutes from the Conway Chain of Lakes, approximately 10 minutes from the Orlando International Airport, 15 minutes from Downtown Orlando, and has convenient access to Orlando's world-famous attractions. Schedule a showing today!

4404 Sailor Court, Orlando

$490,000

4 Beds ⋅ 2 Baths ⋅ Windward Place SubDv. ⋅ 32812 Zip Code

Beautifully maintained 4-bedroom, 2-bathroom home on a cul-de-sac in a centrally located Orlando neighborhood. Just minutes from Orlando International Airport, Downtown Orlando, and close to public and private schools. This property offers unmatched convenience for commuting, education, and entertainment. Inside, the home has been cared for, featuring a new AC system and a newer roof, providing peace of mind for years to come. The spacious layout offers comfortable living areas, generous bedrooms, and a warm, inviting atmosphere throughout. With its ideal location and well-kept condition, this home is a fantastic opportunity for buyers seeking comfort, convenience, and value in the heart of Orlando.

3726 Sarasota Court, Orlando

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