Windward Place Real Estate

Welcome to Windward Place, an enchanting subdivision nestled in the heart of Orlando, Florida, within the vibrant Orange County. This picturesque community is a hidden gem, offering a perfect blend of tranquility and convenience for families, professionals, and retirees alike.

Windward Place is characterized by its beautifully designed homes, lush landscaping, and friendly atmosphere. As you stroll through the tree-lined streets, you'll be greeted by well-maintained yards and a warm sense of community. With a variety of architectural styles, from contemporary to traditional, there’s a home to suit every taste and lifestyle.

One of the standout features of Windward Place is its prime location. Just a short drive from the bustling attractions of downtown Orlando, residents enjoy easy access to world-class dining, shopping, and entertainment options, including the famous theme parks that make this city a top destination. For those who appreciate the great outdoors, nearby parks and recreational areas provide ample opportunities for hiking, biking, and enjoying Florida’s beautiful weather.

Families will appreciate the highly-rated schools in the area, ensuring that children receive a quality education. Additionally, the community fosters a strong sense of belonging, with regular neighborhood events and gatherings that bring residents together.

Whether you're seeking a peaceful retreat or a vibrant community close to the action, Windward Place offers the best of both worlds. Discover your dream home in this delightful Orlando subdivision, where every day feels like a vacation!

Newest Listings in Windward Place

$535,000

3 Beds ⋅ 3 Baths ⋅ O6440628 MLS

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 ⋅ O6422857 MLS

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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