Oakland Park Real Estate

Oakland Park Real Estate

Welcome to Oakland Park, a vibrant and charming subdivision nestled in the heart of Winter Garden, Florida, within beautiful Orange County. This picturesque community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and young professionals alike.

Oakland Park is renowned for its thoughtfully designed homes that cater to a variety of lifestyles. Whether you’re searching for a cozy single-family residence or a spacious modern home, this neighborhood has something for everyone. The lush landscaping, tree-lined streets, and well-maintained parks create a welcoming atmosphere that encourages outdoor living and community engagement.

One of the standout features of Oakland Park is its proximity to Winter Garden’s thriving downtown area. Residents enjoy easy access to a plethora of dining, shopping, and entertainment options, including the popular Winter Garden Village. Farmers markets, art festivals, and seasonal events bring the community together, fostering a strong sense of belonging among neighbors.

For those who appreciate the great outdoors, Oakland Park is close to the West Orange Trail, perfect for walking, jogging, or cycling while soaking in the beautiful Florida sunshine. Families will also appreciate the highly-rated schools in the area, ensuring that children receive a quality education.

With its ideal location, charming homes, and a strong sense of community, Oakland Park in Winter Garden is more than just a place to live—it’s a lifestyle. Discover the magic of this delightful subdivision and make it your home today!

Newest Listings in Oakland Park

$469,000
3 Beds ⋅ 2 Baths ⋅ Oakland Park SubDv. ⋅ 32127 Zip Code
Fully renovated from top to bottom, this 3-bedroom, 2-bath home sits on one of the most private lots in the neighborhood, offering unobstructed lake views from two sides, no rear neighbors, and no neighboring home on one side. The split floor plan features an open, functional layout with high-end finishes throughout. The kitchen has been completely redesigned with custom cabinetry, quartz countertops, new stainless steel appliances, and generous prep and storage space. High-grade 12mm luxury vinyl plank flooring runs throughout the home, while the family room is highlighted by a custom real stone feature wall, individually laid stone by stone. Both bathrooms have been fully renovated with quartz countertops, European-style tile, frameless glass shower enclosures, and designer finishes. Every renovation was completed with an emphasis on quality craftsmanship rather than builder-grade materials. Major updates include a new roof, upgraded privacy fencing, and a new irrigation system with fresh landscaping and sod. The combination of meticulous renovations, exceptional privacy, and expansive water views creates a home that is truly one of a kind

427 Pendrey Drive, Port Orange
$1,125,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to a life beautifully lived. Situated on a premier corner lot in Oakland Park, Winter Garden's golf cart community, this exceptional residence blends thoughtful design, effortless indoor-outdoor living, & a private tropical retreat. Freshly redesigned professional landscaping with premium weed barrier, smart irrigation, app control, & a mature Medjool date palm creates stunning curb appeal. A custom front door opens to a partially screened wraparound front porch, perfect for morning coffee or evening chats. Inside, rich hardwood floors span the main level, complemented by abundant natural light, crown molding, plantation shutters, designer lighting, brass floor outlets in the living room & office, and ceiling fans throughout. The kitchen features granite countertops, a farmhouse sink, stainless steel appliances, tile backsplash, under-cabinet lighting, a beverage refrigerator, & a new Bosch dishwasher and microwave (2023). Open to the living & dining areas, it overlooks the front porch & connects seamlessly to outdoor living through French doors. A flexible front room serves as an office, study, or playroom. A powder room serves guests. The first-floor owner's suite overlooks the pool & offers dual granite vanities, a spa-style walk-in shower, linen storage, custom California Closets, & direct laundry room access. Upstairs, hardwood flooring continues throughout 3 spacious bedrooms, including one en-suite, plus two full baths and a generous loft ideal for theater, fitness, playroom, or guest retreat. A whole-home Generac natural gas generator keeps lights, air conditioning, & appliances running during outages. Step outside to one of Oakland Park's rare full-size Jandy-iAqualink-controlled saltwater pool & spa. The pool measures approximately 12' x 30' with depths from 3' to 5' & features an 8' x 12' sun shelf with bubbling fountain and umbrella sleeve. The approximately 6' x 8' spa includes four therapy jets and heats in 20-30 minutes. Equipment includes a 2.7 HP Jandy Variable-Speed Energy-Efficient Pump & Jandy 400,000 BTU natural gas heater. A travertine pool deck, oversized covered rear porch, vinyl-fenced yard with dual gates, & three-car garage with built-in storage racks complete the outdoor experience. Oakland Park offers a waterfront, golf-cart-approved lifestyle with two resort-style pools, a clubhouse, dog park, playgrounds, parks, & spectacular sunsets. Two blocks from the waterfront trail, minutes from the 22-mile West Orange Trail, & near multiple parks. Historic downtown Winter Garden is a golf cart ride away, offering Crooked Can Brewery, rooftop dining, boutique shopping, splash park, Farmers Market, live theater, golf cart parades, 5Ks, book clubs, poker nights, and more. Convenient access to major interstates, premier golf courses, shopping, & Central Florida theme parks. Additional features: fresh interior/exterior paint (2021), Apple HomeKit-compatible door locks, thermostats & ceiling fans, Apple Secure Video cameras at the doorbell, front entry, pool area & indoor locations, new remote-controlled high-velocity fans on both porches, Apple HomeKit-controlled owner's bath fan, outlets inside primary bath cabinetry, & a state-of-the-art termite detection and control system with full warranty. Lovingly maintained & thoughtfully enhanced throughout, this one-of-a-kind Oakland Park pool & spa home is a special opportunity. Your oasis is waiting. Make it yours.

925 Easley Avenue, Winter Garden
$625,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained, move-in ready 3-bedroom, 3-bathroom home in the highly sought-after Oakland Park community of Winter Garden. Combining timeless architecture with modern upgrades, this turnkey home offers the perfect blend of comfort, style, and convenience. Inside, you'll find a bright, open-concept floor plan with abundant natural light, soaring ceilings, spacious living and dining areas, and a flexible layout ideal for entertaining, working from home, or accommodating multigenerational living. The chef-inspired kitchen features desirable gas appliances, generous counter space, ample cabinetry, and seamlessly connects to the main living areas, creating the heart of the home. Thoughtful upgrades throughout include plantation shutters, designer finishes, and quality craftsmanship, providing a low-maintenance lifestyle that allows you to simply move in and enjoy. The spacious primary suite offers a private retreat with a luxurious ensuite bathroom and generous walk-in closet, while the additional bedrooms and bathrooms provide flexibility for family, guests, or a dedicated home office. Step outside and enjoy Oakland Park's signature charm, featuring tree-lined streets, inviting front porches, scenic green spaces, and resort-style amenities that foster a true sense of community. Perfectly located just minutes from Historic Downtown Winter Garden, the award-winning Farmers Market, the West Orange Trail, boutique shopping, popular restaurants, community events, and convenient access to SR 429, the Florida Turnpike, Disney, downtown Orlando, and Orlando International Airport. Families will appreciate the proximity to top-rated schools and nearby parks. Whether you're searching for a primary residence, a second home, or simply a home that offers an exceptional lifestyle in one of Central Florida's most desirable communities, this Oakland Park gem delivers the location, upgrades, and quality you've been waiting for.

914 Trowman Alley, Winter Garden
$1,649,999
6 Beds ⋅ 5 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Virtually Staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36” dual-fuel range, warming oven, and a 48” side-by-side refrigerator and freezer. Upgraded quartz countertops, a brick backsplash and hearth with built-in electric fireplace, and engineered hardwood floors elevate the open-concept main living areas. Additional luxury touches include Brizo faucets, custom plantation shutters, and floating shelving systems in every bedroom closet. The owner’s suite offers a spa-inspired retreat with a 6-foot soaking tub, while the upgraded pantry with butcher block countertop, dimmer switches, and ceiling fans throughout enhance everyday comfort. An in-law suite featuring a full bath, family room, and a private staircase above the garage provides the perfect space for guests, extended family, or a private home office. Enjoy peaceful mornings and sunset evenings from the screened front and side porches, adding to the home’s charm and livability. Located in Oakland Park, residents enjoy resort-style amenities including two community pools, multiple parks and playgrounds, scenic walking and biking trails, a clubhouse, and direct access to the West Orange Trail. With tree-lined streets, lake views, and friendly front-porch living, this award-winning community captures the very best of Winter Garden living.

1101 Eagles Pass Way, Winter Garden
$859,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
OAKLAND PARK---a PARADE of HOMES winning community! Nestled beneath a canopy of mature trees and perfectly positioned across from a PARK, this charming home welcomes you with a spacious covered front porch where you can relax and enjoy nature and the peaceful surroundings. Thoughtfully designed with warmth and character throughout, the home features rich WOOD flooring, beautiful custom ACCENT WALLS, and a stunning staircase that adds style and sophistication to the inviting interior. Offering 3 bedrooms, 2.5 baths, a dedicated formal dining space, and a small bonus area upstairs suitable for an OFFICE—-a functional yet elegant layout, this home was designed with the homeowner in mind. The kitchen is beautifully appointed with stone countertops, tile backsplash, abundant cabinetry, and a built-in desk area that adds both charm and convenience. A dedicated COFFEE BAR creates the perfect morning retreat, while the walk-in pantry and additional secondary pantry provide exceptional storage space. The downstairs spacious laundry room is equally impressive, featuring a utility sink and extensive counter space ideal for organization and everyday functionality. The living room is embraced with natural light from an abundance of windows overlooking the backyard, while extended FRENCH DOORS create a seamless connection to the covered outdoor living space, enhancing the home’s warm and welcoming atmosphere. A convenient half bath and entry door are located adjacent to the covered porch, offering seamless indoor-outdoor living. The outdoor space is already enhanced with pavers, creating a polished and low-maintenance setting ideal for entertaining, relaxing, or future customization. With ample room to design and build a POOL, the backyard offers endless possibilities to create your dream oasis. The upstairs PRIMARY SUITE offers a relaxing retreat complete with dual sinks, an oversized walk-in shower, linen closet, a separate private water closet, and a generously sized walk-in closet. Two additional bedrooms and one full bath are located upstairs. Blending comfort, charm, and thoughtful design, this beautifully customized home offers an exceptional opportunity to enjoy cozy living spaces, stunning outdoor potential, and timeless character in a picturesque PARK setting. Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!

907 Easley Avenue, Winter Garden
$2,098,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!

1258 Ridge Lake Way, Oakland
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