Winter Garden/Oakland Real Estate

Winter Garden/Oakland Real Estate

Welcome to Winter Garden and Oakland, two enchanting gems nestled in the heart of Orange County, Florida. This vibrant region is a perfect blend of small-town charm and modern amenities, making it an ideal place for families, retirees, and everyone in between.

Winter Garden, known for its picturesque downtown area, boasts a rich history that dates back to the 1800s. Stroll along Plant Street, where you’ll find delightful boutiques, cozy cafés, and a thriving farmer’s market that showcases the best local produce. The scenic West Orange Trail runs through the area, offering miles of paved paths for walking, biking, and enjoying the stunning Florida sunshine.

Just a stone’s throw away, the quaint town of Oakland adds to the allure of the region. With its historic homes and tree-lined streets, Oakland exudes a peaceful, community-focused atmosphere. Residents enjoy easy access to beautiful parks, including the serene Lake Apopka, perfect for fishing, kayaking, or simply soaking in the natural beauty that surrounds them.

Both Winter Garden and Oakland are conveniently located near major highways, providing quick access to Orlando’s world-class attractions, shopping, and dining. Families will appreciate the highly-rated schools and community events that foster a strong sense of belonging.

Whether you’re looking for a charming home, a place to start a family, or a peaceful retreat, Winter Garden and Oakland offer an unparalleled quality of life. Come explore this captivating region, where every day feels like a vacation!

Newest Listings in Winter Garden/Oakland

$859,000
4 Beds 3 Baths Summerlake Pd Ph 3b SubDv. 34787 Zip Code
RARE FIND! Experience resort-style living in this exceptional home on a rare OVERSIZED 0.15-acre homesite, ideally located JUST MINUTES from the vibrant HAMLIN Town Center in one of Winter Garden's most desirable areas. Featuring a stunning nearly NEW HEATED SALTWATER PRIVATE POOL, premium summer kitchen, expansive covered lanai, elegant travertine patio, and a fully fenced backyard, this property offers the Florida lifestyle today's buyers are looking for. Offering 2,990 square feet, 4 spacious bedrooms, and 2.5 bathrooms, this home perfectly blends luxury, comfort, energy efficiency, and everyday functionality. Designed with flexibility in mind, it also features a versatile flex room with the potential to serve as a future fifth bedroom, home office, or study, as well as a spacious upstairs bonus room ideal for a media room, playroom, or additional family living space. The primary suite is complemented by an oversized walk-in closet. The fully fenced backyard is a true private retreat designed for entertaining and relaxing year-round. The nearly new heated saltwater pool was built with all required permits, offering the confidence and peace of mind that come with a recently constructed, modern pool system. Outdoor living is completed by the covered lanai and travertine deck, a premium summer kitchen, and low-maintenance artificial turf. A convenient first-floor half bathroom with direct access to the backyard makes entertaining even more enjoyable. Beyond its outdoor living spaces, this home also delivers a remarkable financial advantage. The FULLY PAID-OFF SOLAR PANEL SYSTEM, valued at over $30,000, means no lease or loan to assume and helps keep the average monthly electric bill at approximately $80, even during Florida's summer months. That's hundreds of dollars in energy savings every month, providing exceptional long-term value and sustainability for the next homeowner. Additional upgrades include a beautifully remodeled upstairs bathroom with a frameless glass shower enclosure, custom closet systems, two independent HVAC systems for enhanced comfort and efficiency, professionally installed gutters, an epoxy-coated garage floor, and overhead garage storage racks. The location adds even more value: just minutes from Hamlin Town Center, with convenient access to top-rated schools, Publix, Walmart, restaurants, cafés, boutique shopping, Cinépolis Luxury Cinemas, PopStroke, Urban Air Adventure Park, and SR-429. As a resident of the highly desirable Summerlake community, you'll enjoy standout amenities, including a clubhouse, fitness center, community pool, tennis courts, playgrounds, walking trails, and lawn maintenance included through the HOA. Move-in ready and thoughtfully upgraded throughout, this home offers a rare combination of outdoor living, energy efficiency, and prime Winter Garden location. Schedule your private showing today! All information, including room dimensions, square footage, HOA fees, community amenities, and restrictions, is deemed reliable but not guaranteed and should be independently verified by the buyer and buyer’s agent.

7594 Lake Hancock Boulevard, Winter Garden

$1,249,990
5 Beds 4 Baths Twinwaters SubDv. 34787 Zip Code
Virtually Staged. Modern architecture. Total effortlessness. This five-bedroom residence is a masterclass in high-end finish designs, featuring high ceilings, iron-rod accents, and a dramatic, gallery-inspired aesthetic. At its heart, a chef-caliber kitchen serves as the ultimate hub for refined entertaining. Step into a home where luxury meets thoughtful innovation. This sprawling corner-lot property, crafted by the renowned Meritage Homes, is a rare find that perfectly balances grand proportions with everyday comfort. Boasting five spacious bedrooms, four full baths, and two half baths, the layout is designed for those who love to host and move freely through their space. The heart of the home is an expansive, sun-drenched open floor plan that flows effortlessly toward your own private oasis. Step outside to find a beautiful screened-in pool area, ideal for afternoon swims or evening gatherings without the worry of the elements. What truly sets this residence apart is the commitment to quality and efficiency. Protected by a timeless tile roof, the home features high-energy windows and spray-foam attic insulation, keeping the interior crisp and cool while keeping utility costs in check. The oversized three-car garage even comes equipped with a Tesla charger, ready for your electric vehicle. From the numerous high-end upgrades found throughout the interior to the curb appeal of its prominent corner position, every detail has been considered. This is more than just a house; it’s a modern, energy-efficient sanctuary built for a sophisticated lifestyle. The experience extends to a private pool house, complete with a game room and a theater-style loft. Outside, the pool anchors an at home retreat. This is luxury without the logistics. Your residency is entirely turnkey and ready for you to move in.

1734 Amsel Falls Park Terrace, Winter Garden

$915,000
3 Beds 4 Baths Park Place At Winter Garden SubDv. 34787 Zip Code
Experience luxury living in the heart of historic downtown Winter Garden! This beautifully designed corner-unit brownstone offers 3 bedrooms, 3.5 bathrooms, 2,242 square feet of thoughtfully crafted living space, and an unbeatable location just steps from everything that makes downtown so special. Situated right next to Plant Street Market and Crooked Can Brewing Company, you'll enjoy effortless access to the award-winning Saturday Farmers Market, local festivals, live entertainment, boutique shopping, and an incredible selection of restaurants and cafés, all just outside your front door. Step inside to discover a the first-floor layout featuring a private bedroom with its own en suite bathroom, creating the perfect retreat for overnight guests, extended family, or even a private home office. The second floor is the heart of the home, where an open-concept living, dining, and kitchen area creates an inviting atmosphere for both entertaining and everyday living. As a coveted corner unit, oversized windows fill the space with natural light, while crown molding adds an elegant finishing touch throughout. The gourmet kitchen is designed to impress, showcasing an oversized center island, stainless steel appliances, stylish finishes, generous counter space, and abundant cabinetry. A dedicated bar area nearby makes hosting gatherings even more effortless, while the adjoining living room features access to two covered balconies, giving you the perfect place to enjoy fresh air or unwind after a day exploring downtown. Occupying the third floor, the spacious primary suite offers a peaceful escape with a large walk-in closet and a luxurious en suite bathroom complete with dual vanities and a stunning freestanding soaking tub. An additional upstairs bedroom provides generous closet space, abundant natural light, and comfortable accommodations for your loved ones. Additional highlights include a two-car garage and a location within Winter Garden's highly desirable golf cart district, making it easy to explore downtown's vibrant shops, restaurants, parks, and community events without ever needing your car. Convenient access to major highways places the rest of Central Florida within easy reach, while your everyday lifestyle is centered around one of the region's most sought-after downtown destinations. If you've been searching for luxurious low-maintenance living with unmatched walkability, this exceptional townhome is the opportunity you've been waiting for. Schedule your private showing TODAY!!!

484 W Plant Street, Winter Garden

$1,100,000
4 Beds 3 Baths Lake Apopka Sound Ph 1 SubDv. 34787 Zip Code
Move in ready home with remarkable sunsets, breathtaking panoramic views of Lake Apopka, and calming bird watching right from the backyard. Highlights of this home from outside to inside are wide paver driveway with parking pad, spacious 3 car garage, covered front and rear porches, fully fenced in backyard, extended rear concrete patio, large flex room, mother in law suite with private entrance and kitchenette, and incredible kitchen to love at the center of an open floorplan. Floorplan: Triple split layout puts the primary suite, the secondary bedrooms, and the mother in law suite each in their own private area of the home. The mother in law suite has its own private exterior entrance, kitchenette, bedroom, and full bath. Large flex room for a home gym, office, studio, gaming room, or playroom. Kitchen: Cabinets to the ceiling, stone counters, beveled subway tile, farmhouse sink, island with seating for four, built-in wall oven and microwave, stainless vented hood, pot filler above the cooktop, spacious pantry, open to the living and dining space. Interior: Tray ceilings in the dining room, living room, and primary suite, wood slat accent wall, crown molding, upgraded lighting, ceiling fans, window treatments installed. Primary suite with walk in closet, corner tub, double sinks, and glass shower. Ceramic tile in main living areas, carpet in secondary bedrooms, inside laundry room. Exterior: Wide paver driveway with large paved parking pad, spacious three car garage, covered front porch, covered rear porch, extended full width concrete patio, fully fenced backyard with gates on both sides, sprinkler system throughout, tile roof. Recreation: Killarney Station trailhead five minutes out with bike rentals, repairs, and supplies center. West Orange Trail runs 20 plus miles into historic downtown Winter Garden. Lake Apopka Wildlife Drive and Lake Louisa State Park both an easy drive. Convenience: Downtown Wintergarden 25 minutes, Costco 8 minutes, Disney 25 minutes, Downtown Orlando 30 minutes, MCO Airport 35 minutes.

17854 Hither Hills Circle, Winter Garden

$219,000
3 Beds 2 Baths Grove Residence & Spa Hotel Condo Ii SubDv. 34787 Zip Code
**Beautiful 3-bedroom/2-bathroom Jasmine floorplan available for sale at The Grove Resort and Water Park! This first floor apartment is fully-furnished and has everything you need for a wonderful vacation condo! This spacious unit has 14-foot ceilings in the main living space, giving a light, airy feel, and opens to an enclosed balcony where you can enjoy views of gardens and pond. Full kitchen has everything you need for cooking breakfasts, to family dinners, with a full washer and dryer in a room just off the kitchen. The living room also has a sleeper sofa for extra guests if needed. A short stroll brings you to either the central front desk area where you will find The Marketplace, the well-stocked convenience store, and the gift shop and concierge desk, or to the Springs Pools area where you can choose from three beautiful pools and the hot tub. The Valencia Restaurant, with additional outside seating, is open for breakfast, lunch, and dinner, 7 days a week, and is next to the 24/7 gym. Take a walk down to Lake Austin and try some fishing, or paddle a swan boat! From there you can visit the Surfari water park with its large pool, lazy river, water slides, and splash area! Try out the Flowrider surfing experience, or just watch while enjoying food and drinks from the Longboard Bar and Grill! Flip Flops is the 6000sf games arcade with glow-in-the-dark mini golf, so don't miss that! Free daily shuttles to the Disney parks are available for all owners and guests! This truly is a great place to own a vacation condo while the onsite management company rent out your unit when you are not there! Call for more details!!**

14501 Grove Resort Avenue Unit 2119, Winter Garden

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