Green Oaks Rep Homes with Sidewalks Community Features

Green Oaks Rep Homes with Sidewalks Community Features

Welcome to Green Oaks Rep, a charming subdivision nestled in the heart of Winter Park, Florida, within the picturesque Orange County. This delightful community is perfect for those seeking a serene suburban lifestyle while being just a stone's throw away from the vibrant culture and amenities of Winter Park.

Green Oaks Rep boasts beautifully designed homes that blend modern comfort with classic elegance. Each residence is thoughtfully situated along tree-lined streets, encouraging a sense of community and connection among neighbors. One of the standout features of this subdivision is its extensive network of sidewalks, which not only enhances the neighborhood's aesthetic appeal but also promotes an active lifestyle. Residents can enjoy leisurely strolls, morning jogs, or evening bike rides, all while soaking in the lush surroundings.

The community is strategically located, providing easy access to Winter Park's charming downtown area, renowned for its boutique shops, art galleries, and gourmet dining options. Families will appreciate the proximity to highly-rated schools and recreational parks, making Green Oaks Rep an ideal choice for those with children.

In addition to the beautiful homes and community features, Green Oaks Rep fosters a friendly atmosphere where neighbors become friends. Regular community events and gatherings help strengthen bonds and create lasting memories. Whether you're looking to settle down or invest in a property, Green Oaks Rep is a fantastic choice for those seeking a welcoming and vibrant community in Winter Park. Come explore the charm and comfort of Green Oaks Rep – your dream home awaits!

Newest Green Oaks Rep Homes with Sidewalks Community Features

1600 Legion Drive, Winter Park
$3,495,000
5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code
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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