Green Oaks Rep Homes with Pool

Green Oaks Rep Homes with Pool

Welcome to Green Oaks Rep, a charming subdivision nestled in the picturesque city of Winter Park, Florida, located in the heart of Orange County. This delightful community is known for its lush landscapes, friendly atmosphere, and a perfect blend of suburban tranquility and urban convenience.

Green Oaks Rep offers an array of stunning homes, many of which feature private pools, making it an ideal choice for those who appreciate the Florida lifestyle. Imagine stepping out into your own backyard oasis, where you can soak up the sun, host summer barbecues, or simply unwind by the water. The homes in this subdivision are designed with modern living in mind, boasting spacious layouts, contemporary finishes, and outdoor spaces that are perfect for entertaining.

Winter Park itself is renowned for its vibrant cultural scene, with an array of boutiques, cafes, and art galleries just a stone’s throw away. Residents can enjoy scenic lakes, beautiful parks, and the famous Winter Park Chain of Lakes, perfect for boating and fishing enthusiasts. The community is also conveniently located near top-rated schools, making it an excellent choice for families.

Whether you’re looking for a serene retreat or a lively neighborhood filled with community spirit, Green Oaks Rep has something for everyone. With homes that come complete with refreshing pools and a welcoming environment, this subdivision is the perfect place to call home. Experience the best of Winter Park living in Green Oaks Rep—your oasis awaits!

Newest Green Oaks Rep Homes with Pool

1600 Legion Drive, Winter Park
$3,495,000
5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv.
Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

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