Oakland Park Homes with Playground Community Features

Oakland Park Homes with Playground Community Features

Welcome to Oakland Park, a delightful subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This charming community is designed for families and individuals alike, offering a perfect blend of comfort, convenience, and a true sense of belonging.

Oakland Park is renowned for its inviting atmosphere and family-friendly environment, making it an ideal place to call home. The homes here are thoughtfully designed, featuring modern layouts, spacious interiors, and beautiful outdoor spaces that encourage a lifestyle of relaxation and enjoyment. With a variety of floor plans to choose from, there's something to suit every taste and need.

One of the standout features of Oakland Park is its fantastic community amenities. Families will appreciate the well-maintained playground, where children can safely play and make lasting memories with friends. The community is also designed for outdoor enthusiasts, offering scenic walking trails and green spaces that invite residents to enjoy the beautiful Florida weather.

In addition to its recreational offerings, Oakland Park is conveniently located near shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away. The charming downtown Winter Garden, with its quaint shops and local eateries, is just minutes away, providing a perfect weekend getaway right in your own backyard.

Whether you’re looking to settle down or invest in a vibrant community, Oakland Park in Winter Garden is an exceptional choice. Come experience the warmth and charm of this inviting neighborhood—your dream home awaits!

Newest Oakland Park Homes with Playground Community Features

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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Aaron Hunt

Meet Aaron Hunt | Tampa Bay & St. Petersburg Real Estate Expert Raised with an entrepreneurial mindset and a passion for delivering exceptional client experiences, Aaron Hunt has become one of the most trusted real estate professionals in the Tampa Bay area. As the Broker and Co-Founder of Avalon Group Realty, Aaron is known for his strategic marketing expertise, skilled negotiation, and concierge-level service that consistently helps buyers and sellers achieve outstanding results. Originally from the San Francisco Bay Area, Aaron grew up surrounded by business ownership and hospitality, with his family operating hotel properties throughout California, Idaho, and Las Vegas. That background shaped his understanding of customer service, presentation, and relationship-building from an early age. Before entering real estate, Aaron worked in the luxury spa industry, where he refined the attention to detail and personalized service approach that continue to define his business today. After relocating to St. Petersburg in 2013, Aaron quickly fell in love with the Tampa Bay lifestyle and became passionate about helping others find their place in the community. Today, he specializes in helping buyers, sellers, investors, relocating families, luxury home clients, and vacation-home seekers navigate the competitive Tampa Bay real estate market with confidence. Aaron has built a strong reputation for working with out-of-state buyers relocating to Florida, providing in-depth local market knowledge, honest guidance, and a seamless experience from start to finish. His clients value his calm communication style, responsiveness, and ability to simplify even the most complex real estate transactions. In 2014, Aaron co-founded Avalon Group Realty and helped grow the company into one of the top-rated real estate teams serving St. Petersburg, Tampa, and the surrounding Tampa Bay communities. Known for innovative digital marketing, high-end property presentation, and hands-on client support, Aaron intentionally limits the number of clients he works with at one time to ensure every client receives personalized attention and exceptional communication throughout the process. Whether helping sellers maximize their home’s value through expert pricing strategy and marketing or helping buyers secure the right property in a competitive market, Aaron approaches every transaction with professionalism, precision, and a commitment to protecting his clients’ best interests. When he’s not working with clients, Aaron enjoys exploring local neighborhoods, biking along the waterfront, discovering new restaurants, traveling, and supporting community events throughout St. Petersburg and Tampa Bay.

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