Oakland Park Homes with Pool Community Features

Oakland Park Homes with Pool Community Features

Welcome to Oakland Park, a vibrant and inviting subdivision nestled in the heart of Winter Garden, Florida. This charming community, located in sunny Orange County, offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and everyone in between.

As you explore Oakland Park, you'll discover beautifully designed homes that cater to a variety of lifestyles. Many of these residences feature stunning pools, allowing you to soak up the Florida sun right in your backyard. Imagine hosting summer barbecues, enjoying leisurely afternoons with a good book by the pool, or creating lasting memories with friends and family in this idyllic setting.

The community itself is thoughtfully designed with an array of amenities that enhance the quality of life for its residents. Enjoy leisurely strolls along tree-lined streets, or take advantage of the community parks and playgrounds that provide a safe space for children to play and explore. With a strong sense of community spirit, Oakland Park hosts various events throughout the year, bringing neighbors together and fostering lasting friendships.

Conveniently located, Oakland Park is just a stone's throw away from Winter Garden's charming downtown area, where you can find delightful shops, local eateries, and vibrant entertainment options. Plus, with easy access to major highways, commuting to nearby cities or enjoying a day at the beautiful Florida beaches is a breeze.

In Oakland Park, you’re not just buying a home; you’re investing in a lifestyle filled with warmth, community, and endless opportunities for relaxation and fun. Come discover the charm of Oakland Park and make it your new home today!

Newest Oakland Park Homes with Pool Community Features

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

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

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

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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Vincent & Christina Barone

In today’s real estate market, selling or buying a home requires advanced knowledge of online as well as traditional marketing platforms. Just having a real estate license and listing a home on the MLS is not enough, you want a Top Agent with lots of experience who has their ear to the ground when it comes to market trends, a deep understanding of the communities they serve, and the ability to think outside the box. As part of the Team Barone, our agents’ skills go far beyond closing deals. A little about us, Myself and my husband have been doing Real Estate for over 30 years. We are Top 1% Nationwide in sales out of 1.3 million Realtors WITH MANY 5-STAR REVIEWS! We have one of the most aggressive online marketing in the industry! WE CLOSED OVER 1/2 BILLION IN SALES! Top producers in the Tampa area with 30 years of experience! When Buying or Selling there are a lot of moving pieces for every transaction, so you need experienced Realtors like us who work well with various vendors, inspectors, title companies, appraises and lenders to make sure you don't have to worry about a thing. With every home we sell, our main priority is our client's bottom line and net proceeds. With our many years of experience & high grossing sales performance, we guarantee you'll be satisfied with your selling price and net proceeds. You will be treated like family not a number like most firms! Our philosophy is simple take care of our clients as we would take care of ourselves. No games, no lies, no tricks, no bait & switch just the honest truth. With these principles that is why after 30 years we are top 1% Nationwide with over 1,600 homes sold!

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