Oakland Park Real Estate

Oakland Park Real Estate

Welcome to Oakland Park, a vibrant and inviting subdivision nestled in the heart of Winter Garden, Florida. This charming community is part of Orange County and boasts a perfect blend of suburban tranquility and convenient access to urban amenities.

Oakland Park is renowned for its beautifully designed homes that cater to a variety of lifestyles, from young families to retirees seeking a peaceful retreat. With meticulously landscaped yards and a friendly atmosphere, this neighborhood exudes warmth and community spirit. Residents enjoy a plethora of amenities, including scenic walking trails, lush parks, and recreational facilities that encourage an active lifestyle.

One of the standout features of Oakland Park is its prime location. Just a short drive away, you’ll find the historic charm of downtown Winter Garden, where you can explore delightful shops, dine at local eateries, and participate in community events throughout the year. The area is also conveniently situated near major highways, making commutes to Orlando and beyond a breeze.

Families will appreciate the highly-rated schools within the district, ensuring quality education for children of all ages. With a strong sense of community and a focus on family-friendly living, Oakland Park is an ideal place to call home.

Whether you're looking to buy your first home, downsize, or invest in a rental property, Oakland Park offers a welcoming environment that feels just right. Come and discover the charm of Oakland Park, where your dream home awaits!

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
$595,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained, move-in ready 3-bedroom, 3-bathroom home in Oakland Park, one of Winter Garden’s most desirable communities. Offering a blend of classic architecture, modern updates, and an exceptional location, this turnkey Winter Garden home is designed for comfortable Florida living. Step inside to a bright and spacious open-concept floor plan featuring abundant natural light, soaring ceilings, and generously sized living and dining areas. The flexible layout is ideal for entertaining, working from home, or accommodating guests. At the center of the home is the chef-inspired kitchen, featuring natural gas appliances, ample cabinetry, generous counter space, and an open connection to the main living areas. Whether you're preparing a weeknight dinner or entertaining friends and family, this kitchen is both functional and inviting. The spacious primary suite provides a private retreat with a luxurious ensuite bathroom and generous walk-in closet. Two additional bedrooms and bathrooms offer plenty of flexibility for family, guests, a home office, or additional living space. Throughout the home, you'll find plantation shutters, designer finishes, and quality upgrades that create a polished yet comfortable atmosphere. With thoughtful improvements already in place, you can move in and start enjoying the lifestyle this home and community have to offer. And then there's Oakland Park. Residents have access to an impressive collection of resort-style community amenities, including TWO community pools, beautiful green spaces, parks, playgrounds, walking paths, gathering areas, and the neighborhood’s iconic tree-lined streets and welcoming front porches. Oakland Park is designed to create a true neighborhood feel while offering the amenities buyers want from a premier Winter Garden community. Location is hard to beat. You're just minutes from Historic Downtown Winter Garden, the popular Winter Garden Farmers Market, the West Orange Trail, local restaurants, boutique shopping, parks, and year-round community events. Convenient access to SR 429 and the Florida Turnpike makes commuting throughout Central Florida easy, while Disney, downtown Orlando, and Orlando International Airport are all within a manageable drive. If you're searching for a move-in ready home in Winter Garden, a community with resort-style amenities and pools, or a home close to Downtown Winter Garden and the West Orange Trail, this Oakland Park property checks the boxes. Experience the charm, convenience, and lifestyle that make Oakland Park one of Winter Garden's most sought-after communities.

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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