Oakland Park Homes with Playground Amenities

Oakland Park Homes with Playground Amenities

Welcome to Oakland Park, a charming subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This delightful community is designed for those who appreciate a blend of modern living and the warmth of a close-knit neighborhood. With its picturesque streets and beautifully landscaped homes, Oakland Park offers a serene escape while being just a stone's throw away from the bustling attractions of Central Florida.

One of the standout features of Oakland Park is its family-friendly atmosphere, highlighted by the fantastic playground amenities available to residents. This community is perfect for families looking to create lasting memories, as the playgrounds provide a safe and engaging environment for children to explore, play, and socialize. Parents can enjoy peace of mind knowing their little ones are just a short walk away, enjoying the fresh air and outdoor activities.

In addition to the playgrounds, Oakland Park boasts a variety of homes that cater to diverse lifestyles. From cozy single-family residences to spacious two-story designs, each home is thoughtfully crafted with modern amenities and stylish finishes. The community also encourages an active lifestyle, with walking trails and parks that invite residents to embrace the beautiful Florida weather.

Living in Oakland Park means enjoying a vibrant community that values connection, recreation, and family. With its ideal location, excellent amenities, and welcoming atmosphere, this subdivision is truly a hidden gem in Winter Garden. Come discover why so many families are proud to call Oakland Park home!

Newest Oakland Park Homes with Playground Amenities

1021 Huntspoint Street, Winter Garden
$865,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
*** Seller MOTIVATED - Moving Out of State *** RARE opportunity in Oakland Park, a Parade of Homes-winning community: a 2018 home with approximately $145K in owner upgrades that YOU and your family can enjoy, including a premium SOLAR plus whole-home battery system (paid off at closing). This home is PRICED to MOVE. Offering 4 bedrooms, 3.5 baths, and 2,445 square feet, with a flexible main-floor suite, loft, dining space, tile flooring, newer AC (2024), and a screened balcony, it is built for everyday living, entertaining, and working from home, and is fully fenced for privacy. The main-floor suite is framed by statement doors, with a built-in MURPHY BED and private patio. It works as a 4th bedroom, guest suite, or home office, ideal for multigenerational living. Upstairs, each bedroom enjoys its own en-suite bath, and one opens to the screened balcony. The PRIMARY SUITE includes dual sinks, ample counter space, a soaking TUB, tiled shower, and walk-in closet. The stylish, highly functional kitchen features QUARTZ counters, tile backsplash, custom wood-trim island, and a water filtration system, with APPLIANCES UPDATED in recent years (Bosch dishwasher, LG ThinQ refrigerator, built-in oven and microwave). Just off the kitchen are two pantries, a built-in desk, and extra under-stair storage. CUSTOM finishes add warmth throughout: an electric FIREPLACE with shiplap in the living area, board-and-batten in the primary bedroom, a shiplap accent wall in the secondary bedroom, custom staircase wall, plantation shutters, updated lighting, and a remodeled half bath. Custom closet systems in every bedroom, two linen closets, multiple pantry closets, and added laundry-room cabinetry with a drying rack keep everything organized. The standout garage offers a dedicated mini-split AC, EV charger, epoxy flooring, and abundant built-in storage with an overhead lift system, and connects to the home by a covered walkway, a rarity in the neighborhood. The crown jewel: a premium 12.64 kW solar and whole-home battery system (installed 2024, an approximately $86K value paid off at closing) with 32 Mission Solar panels and four Enphase IQ Battery 5P units (~20 kWh storage) that can power virtually the entire home during outages. Enjoy a monthly energy bill of about $35. A short GOLF-CART ride from Historic Downtown Winter Garden's award-winning restaurants, shopping, farmers market, and events. This golf-cart-friendly waterfront community offers two pools, a clubhouse, parks, playgrounds, a dog park, and access to the 22-mile West Orange Trail, with easy reach to interstates, golf, and world-renowned theme parks. More than a home, it is the Winter Garden lifestyle.

1021 Huntspoint Street, Winter Garden
910 Trowman Aly, Winter Garden
$638,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to this modern 3-bedroom, 2 and 1/2-bath residence, 1650 square feet located in McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. This Home has a nice welcoming front porch and showcases timeless architecture, upscale designer finishes. Step inside to discover soaring ceilings, beautiful luxury vinyl plank flooring throughout the main living areas. At the heart of the home on the 2nd Story, the Executive kitchen features custom cabinetry with updated hardware, quartz countertops, an island, a gas range, vent hood, tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room with a Balcony to have coffee in the morning or tea in the evening. The upstairs has a lofty feel has a nice living space. Cathedral ceilings, walk-in closet. One of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market close to Winter Garden Village at Fowler Groves the outdoor Mall and the Orlando International Airport. With convenient access to Florida's Turnpike, SR-429, 408, to downtown Orlando, and Central Florida's world-famous attractions and Themed Parks, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

910 Trowman Aly, Winter Garden
925 Easley Avenue, Winter Garden
$1,075,000
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
907 Easley Avenue, Winter Garden
$840,000
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
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