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 vibrant community is a hidden gem that beautifully marries suburban tranquility with urban convenience, making it an ideal place for families, professionals, and retirees alike.

As you stroll through the tree-lined streets of Green Oaks Rep, you’ll discover a welcoming atmosphere characterized by its well-maintained homes and friendly neighbors. One of the standout features of this community is its commitment to walkability, with sidewalks that encourage residents to enjoy leisurely walks, morning jogs, or evening strolls with loved ones. These pathways not only enhance the neighborhood's charm but also foster a sense of connection among residents.

The homes in Green Oaks Rep are thoughtfully designed, offering a variety of styles and sizes to suit diverse lifestyles. Whether you’re looking for a cozy single-family home or a spacious residence, this community has something for everyone. Many properties boast lush yards and inviting outdoor spaces, perfect for entertaining or simply enjoying the beautiful Florida weather.

Beyond the beautiful homes, Green Oaks Rep is conveniently located near top-rated schools, parks, and shopping areas, providing residents with everything they need right at their fingertips. With its blend of community spirit and modern amenities, Green Oaks Rep is more than just a place to live; it’s a place to call home. Come and experience the warmth and charm of this delightful Winter Park community today!

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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