Winter Garden/Oakland Real Estate

Winter Garden/Oakland Real Estate

Winter Garden and Oakland are two charming cities located in the state of Florida. Situated in Orange County, Winter Garden and Oakland offer a unique blend of small-town charm and modern amenities.

Winter Garden is known for its historic downtown area, which is filled with quaint shops, restaurants, and art galleries. The city also boasts beautiful parks and recreational areas, including Lake Apopka, where residents can enjoy boating, fishing, and hiking. Winter Garden is also home to the West Orange Trail, a popular 22-mile paved trail that is perfect for walking, jogging, or biking.

Oakland, on the other hand, is a smaller town located just west of Winter Garden. Despite its size, Oakland has a rich history and is proud of its heritage. The town features several historic buildings, including the Oakland Presbyterian Church, which was built in 1913 and is listed on the National Register of Historic Places.

Both Winter Garden and Oakland are conveniently located near major highways, making it easy for residents to commute to nearby cities like Orlando and Kissimmee. The region is also known for its excellent schools, making it an attractive choice for families.

In summary, Winter Garden and Oakland offer a charming and picturesque setting with a rich history and plenty of recreational opportunities. Whether you're looking for a small-town atmosphere or easy access to nearby cities, this region in Florida has something for everyone.

Newest Listings in Winter Garden/Oakland

$570,000
4 Beds 2.5 Baths Signature Lks-Pcl 01d Ph 01 SubDv. 34787 Zip Code
This beautiful home is located in the sought-after Independence Community/Signature Lakes and it has 4 bedrooms, 2.5 baths, a large family room, dinette area, formal living room and dining room, 2 car garage and a long driveway in which you can park at least 4 additional cars, and a screen cover porch. As you step inside, you'll immediately notice the fresh, new interior and exterior paint and the tile floors throughout which it makes it very easy to maintain. The kitchen boasts large 42” wood cabinets, kitchen island with pendant lights, granite counter tops, stainless steel appliances, the refrigerator and microwave were changed in 2022. This is a fantastic floor plan with oversized rooms and natural light abounds throughout. When you go to the second floor you will see that the carpet has been changed, is completely new. The large Primary Suite offers tray ceiling, walk-in closet, ceiling fan, window blinds and the private en-suite bath complete with a dual vanity sink, a large garden soaker tub and separate glass enclosed shower. Bedrooms two, three and four are generous in size, and you will also find double vanity sinks in the secondary bathroom. When you step through the sliding glass doors off the family room area and onto a generous screen covered lanai, perfect for enjoying a cup of coffee in the morning, the lanai overlooks a lush green space. On the first floor you will find a half a bathroom, perfect for visitors and in the garage, you have a utility sink. Signature Lakes has something for everyone including 2 clubhouses with fitness centers, meeting and game rooms, two community pools, two boat ramps, dog park, walking and jogging trails, open fields, playgrounds, and a Resort style Clubhouse. The HOA also includes the cable, internet, and the common ground maintenance. This home is located near A-rated schools as well as plenty restaurants, shopping, and less than 10 miles from the enchantment of the Walt Disney World Resort and other theme parks.

14554 Black Cherry Trail, Winter Garden

$1,495,000
4 Beds 3.5 Baths Signature Lks-Pcl 01d Ph 02 SubDv. 34787 Zip Code
"Welcome Home" to the Signature Lakes Independence community! This single-story home offers a prime location within a zoned area for A-rated schools and boasts an array of fantastic amenities. Situated on a canal lot with access to Lake Hancock, residents can enjoy activities such as skiing, fishing, or simply taking in the scenic views. The home's open floor plan and spacious kitchen make it ideal for entertaining and hosting family gatherings. Outside, the ample space and beautiful pool create an inviting setting, complemented by a covered lanai perfect for grilling or simply enjoying the refreshing lake breezes. Additionally, the media room provides a great space for movie nights and entertainment. The property offers numerous desirable features including quartz countertops, 42 maple cabinets, stainless steel appliances, and more. The community itself includes amenities such as a pool, dock, park, and playground, enhancing the overall lifestyle experience. It's important to note that there are additional costs associated with the property, including a $1000 Capital Contribution fee to be paid by the buyer at closing, as well as 2 months of HOA fees. These details provide important information for potential buyers to consider. Overall, this home in the Signature Lakes Independence community presents a wonderful opportunity for those seeking a vibrant and enjoyable living environment with a range of appealing features and amenities.

7325 Wild Blackberry Trail, Winter Garden

$285,000
2 Beds 2 Baths Grove Residence & Spa Hotel Condo 3 SubDv. 34787 Zip Code
This condo/hotel represents a LUCRATIVE investment opportunity, or a dreamy vacation getaway at one of the hottest vacation spots in the world. Benefit from the convenience of a full-service concierge, 24-hour security, and complimentary shuttle service to Walt Disney World, Universal Studios, and Seaworld. Experience the pinnacle of resort living and spectacular occupancy rates in this stunning 6th floor, 2-bedroom, 2-bathroom corner unit at the prestigious Grove Resort in Orlando, complete with all furnishings. Perfectly positioned, this dwelling offers breathtaking views and an abundance of natural light. The spacious, open-plan design features modern finishes and a private balcony ideal for enjoying Florida’s beautiful sunsets. As a resident, you'll enjoy access to world-class amenities including a sprawling water park, full-service spa, fitness center, and multiple dining options. The Grove’s serene environment makes it a perfect retreat, with lush landscapes and tranquil water features. Take advantage of the resort’s on-site lake, where fishing and paddle boating offer a peaceful escape. Whether you’re dining at one of the resort’s gourmet restaurants or lounging by the expansive pools, every day feels like a vacation. Embrace luxury living at its finest, where every detail is designed for supreme comfort and entertainment.

14501 Grove Resort Avenue Unit 3636, Winter Garden

$580,000
3 Beds 2.5 Baths Oakland Park SubDv. 34787 Zip Code
Welcome Home to Modern Luxury in McKinnon Square, Oakland Park! Discover your dream home in the coveted Morningdale floor plan. This modern bungalow boasts an inviting 3-bedroom, 2.5-bathroom layout with a seamless open floor design, perfect for both relaxation and entertaining. Gourmet Kitchen Delight, a culinary haven awaits with a spacious center island topped with elegant quartz countertops, complemented by high-end stainless steel appliances, a vented hood, natural gas cooktop range, and built-in oven and microwave. The wood laminate flooring adds warmth and sophistication to your cooking space. Luxurious Master Suite, retreat to your expansive master bedroom featuring a designer tray ceiling and a generous walk-in closet. The en-suite master bathroom is a sanctuary with a huge walk-in shower, promising a spa-like experience every day. Added Conveniences: Benefit from the private upstairs laundry and a location that's unbeatable. Enjoy the charm of Downtown Winter Garden with its shops, restaurants, Plant Street Market, brewery, and the famous Winter Garden Farmer's Market. Not to forget the West Orange Bike and Walking Trail and the Oakland Park Neighborhood Nature Trail overlooking Lake Apopka. Lifestyle at Your Doorstep: Whether you walk, bike, or drive your golf cart, the best of urban living is just moments away. Move-In Ready: This beautiful home is complete and awaiting your arrival. No waiting for building materials - just pack your bags and start your new chapter in elegance and comfort.

909 Mckinnon Square, Winter Garden

$1,195,000
5 Beds 4 Baths Sanctuary/Twin Waters SubDv. 34787 Zip Code
Welcome to 16744 Sanctuary Drive in Winter Garden, FL, where MODERN luxury meets comfort in this stunning 5-bedroom, 4-bathroom home. Nestled on the shores of LAKE AVALON, this pet-friendly sanctuary offers a perfect blend of luxury and comfort, making it ideal for MULTI-GENERATIONAL living. Boasting a spacious 3,156 square feet, this home is thoughtfully designed with four bedrooms on the first floor, providing convenience and accessibility for all generations. Step inside to discover an open floor plan, perfect for relaxation and entertainment. The gourmet kitchen is equipped with top-of-the-line stainless steel appliances, including a wall-mounted hot WATER POT-FILLER carefully situated above the 5 GE Profile burner GAS cooktop, built-in microwave & oven, French door refrigerator, gooseneck faucet, PEARL-INSPIRED backsplash, and more. The primary bedroom suite provides a private retreat with breathtaking WATER views, no rear neighbors, a luxurious en-suite bathroom, and a walk-in closet. Additional bedrooms are strategically placed for PRIVACY, offering a serene living space for family or guests ON LOWER LEVEL. The upstairs BONUS room with a PRE-PLUMB ideal for a future breakfast bar features an additional bedroom, bathroom, and walk-in closet, ideal for separate living quarters. Enjoy the waterfront views from your private outdoor covered Lanai, perfect for unwinding after a long day. This home also offers a pre-plumbed space for future additions, allowing for further customization. 3 CAR Side Load GARAGE. Don't miss the opportunity to make this remarkable property your own. Schedule a showing today and experience the epitome of modern living in Winter Garden, FL at 16744 Sanctuary Drive.

16744 Sanctuary Drive, Winter Garden

$895,000
5 Beds Lakeside At Hamlim SubDv. 34787 Zip Code
Welcome to a BRAND NEW, never lived in, multi-generational property with an unparalleled appeal! Whether catering to family members needing their own private space, diversifying your investment portfolio with a unique home, or seeking to offset your mortgage by renting out the above-garage apartment, this property is an ideal choice. The main house spans 2515 sqft, featuring 4 spacious bedrooms, 3 full bathrooms, and 1 half bathroom, all enhanced with premium upgrades. The main level boasts high ceilings and abundant natural light, fostering an open-concept design seamlessly integrating the kitchen, family room, and dining area. The kitchen is a culinary haven, outfitted with quartz countertops, ample cabinetry, an elegant backsplash, and top-of-the-line stainless steel appliances. Additionally, the main level offers a convenient half bath for guests, a bedroom, and an en-suite bathroom. Ascending the stairs reveals two generous bedrooms sharing a well-appointed bathroom, while the owner's suite provides ultimate privacy with an oversized walk-in closet and a dreamy en-suite featuring upgraded tile flooring, dual vanities, a soaking tub, and a walk-in shower. The above-garage apartment, with its own private entrance, is equally impressive, boasting 624 sqft with full upgrades throughout. Upon entry, revel in luxury flooring, tall ceilings, and an abundance of natural light accentuating the thoughtfully designed floor plan. The kitchen mirrors the main house's style with quartz countertops, ample cabinetry, and a striking backsplash, while stainless steel appliances complete the modern aesthetic. A spacious bedroom and cozy bathroom ensure comfortable living, supplemented by a dedicated laundry room, rendering the secondary home fully self-sufficient. This exceptional property stands as a testament to craftsmanship and innovation, representing a rare opportunity not replicable in the future. The culmination of nearly three years of meticulous planning and construction, it epitomizes unparalleled living in a class of its own. Nestled within a well-established community, this property enjoys an enviable location close to major highways, ensuring convenient access to all amenities. Just minutes away, residents can indulge in excellent shopping opportunities, dine at a variety of luxury and casual eateries, and explore nearby theme parks for entertainment. Moreover, the neighborhood benefits from proximity to brand-new, state-of-the-art hospitals and a top notch school system, providing peace of mind for residents seeking quality healthcare services and high end education for their family. Whether it's shopping, dining, entertainment, education, or healthcare, this vibrant community offers an abundance of options to suit every lifestyle need and preference. Call today to schedule a private tour.

5316 Lake Virginia Street, Winter Garden

$1,175,000
4 Beds 3.5 Baths West Lake Hancock Estates SubDv. 34787 Zip Code
Welcome to luxury living at its finest here in Overlook at Hamlin. This beautiful Taylor Morrison built Courbet model 4/3.5 home is located on an oversized corner lot with views of Lake Hancock and the Magic Kingdom nighttime fireworks. The upgraded stone facade is a curb appeal masterpiece. When you open the front door, you'll be greeted by towering ceilings, aesthetically pleasing 8-foot doors, upgraded wood plank tile floors, and beautiful archways. To the right of the foyer is the dedicated formal dining room with tray ceilings that leads through the butler's pantry to the gourmet kitchen. Don't forget the walk-in pantry for all your goodies. This gorgeously elegant kitchen features beautiful quartz countertops, upgraded shaker cabinets, stainless steel appliances, a gas stove, a breakfast nook, and an island. Are you looking for an expansive living room? Look no further as this home extended the breakfast bar for additional seating overlooking the 2-story living room with ample natural lighting. Are you needing a home office? This home boasts a dedicated downstairs office plenty long enough for putting practice between phone calls and emails. Just off the living room on the main-level is the oversized primary bedroom that impresses with its tray ceilings, his/hers walk -in closets, and expansive spa-like bathroom with a large walk-in shower and a soaking tub for total relaxation. As you walk upstairs, you'll notice the upgraded wooden spindles. Once you are upstairs, you'll find over 1600 sq ft of more space for the family. With a massive game room that could be used as a second living room, billiards room, you name it, you will have plenty of space for entertaining. Not only do you have a game room, but you have a study right off of the game room that could be used as a media room, second home office, nursery room, or an all-important guest room for all the family and friends that will come and visit you. Also, on that side of the upstairs is a large 16x12 bedroom with a walk-in closet and bathroom. Did I mention the upstairs game room and bedroom has views of the lake and the nighttime fireworks? As you walk to the other side of the upstairs, you'll find 2 additional large rooms with their own walk-in closets and a bathroom that boasts a double vanity. As you head back downstairs, you'll find a hallway to the half-bath and laundry room. The laundry room is pre-plumbed for a sink and leads out to the expansive and highly desired 3-car garage which is also pre-plumbed for a whole house water filtration and water softener system. Are you looking for a lower energy bill? This beautiful home boasts solar panels with you in mind. In the backyard you'll find a garden with raised beds, an arched trellis, and plentiful fruit bearing trees and bushes for your pleasure. With the oversized lot nearly twice the size of all the other interior lots in the neighborhood, you have plenty of space for your own private pool, lazy river, and putting green (owner's visions). However, if you'd rather, take advantage of the community's resort style pool instead. Enjoy the neighborhood clubhouse, fitness center, community boat ramp, walking/running trails, park, playgrounds, and a dog park. Being within the Hamlin part of Horizon West, you are a few minutes' drive to the Publix, multiple sit-down restaurants, shops, dine-in movie theater, and more. A quick 20-minute drive to Downtown Winter Garden and the all-famous Winter Garden Farmer's Market.

14204 Colonial Pointe Drive, Winter Garden

$738,000
4 Beds 2.5 Baths Hamlin Reserve SubDv. 34787 Zip Code
Immaculate ‘SINGLE STORY’, West Facing House in Winter Garden with great upgrades and ample Storage space. This Large Spacious House has 4 Bedrooms, 2 Full Bathrooms and 1 Half Bathroom, and 2 Cars Garage with Screened Lanai. Flooring has worry free Porcelain Tiles throughout the house. Walls are decorated with custom Wainscoting Trim work on the main walls. The Master bedroom has Ceiling Fan, Gorgeous custom built in Walk-in Closet. Astonishing Master bathroom has great looking glass tile walls, upgraded hard wood cabinets and Quartz counter tops. Second and Third bedrooms have custom built in Closets and Ceiling fans, and a full bathroom with great looking glass tile walls, plus an upgraded Quartz counter top and solid wood cabinets. Fourth bedroom has custom built-in closet adjacent to half bathroom with upgraded quartz counter top and hard wood cabinets along with a large shelf for storage. Kitchen has Top-of-the-line Kitchen Aid Stainless-Steel Appliances, built in Dishwasher, French Door Refrigerator, upgraded Double Stacked Cabinets, Quartz Countertops and Gas Range. Kitchen also has a special upgrade of Instant Hot filter water system for drinking purpose. The walk-in Pantry has custom built in Shelving for added convenience and space. Laundry room has modern Washer and Dryer, upgraded double stacked cabinets. This house also comes with an additional Refrigerator, Water Treatment/Softener system, Wall mounted TVs in Bedrooms, fully covered Vinyl Fencing, and Outdoor Gas Grill at the backyard. Tankless Gas Water Heater and Gas Dryer will help you to save big on utilities bills in addition to the Most Inexpensive Gas Cooking. This amazing home is located in the highly sought after community of Hamlin Reserve, that is conveniently located in Hamlin Horizon West, close to Shopping, Restaurants, Hospitals, Parks, Highways and Top-rated schools. This is a home you do not want to miss!

6355 Flat Lemon Drive, Winter Garden

$725,000
4 Beds 2.5 Baths Orchard Park At Stillwater Crossing SubDv. 34787 Zip Code
Picture perfect two-story residence in the highly desirable Orchard Park, adjacent to Orchard Hills, featuring community pool, exterior landscaping included with the HOA, and walking distance to Bridgewater Middle School. Home boasts an abundance of upgrades including built in cabinets, stainless appliances, oversized ‘pool-ready’ fenced yard, 3-car garage, and popular floorplan with all bedrooms and loft upstairs. Open concept living takes center stage with a dedicated dining room, family room, office/den, laundry, powder bath, and eat-in kitchen on the main floor. Sliding doors reveal an oversized patio for alfresco dining or outdoor entertaining. Upstairs is a TV loft or playroom and four bedrooms, including a generous primary bedroom retreat with walk-in closet, double vanities, and tiled shower. Three secondary bedrooms offer privacy and dedicated space for all. Bask in a community built for living with yard maintenance including mowing, sprinkler repair, and yard pest control all included in the monthly dues. Other amenities include resort-style pool, playground, dog park, clubhouse, fitness center, and multiple green spaces. Zoned for all ‘A’ rated schools including Keene’s Crossing Elementary, Bridgewater Middle, and Windermere High School. Close to Windermere Prep, Winter Garden Village, and the 429 offering Expressway access to Downtown Orlando. 20 minutes to Disney World, 25 minutes to Universal, and 30 minutes to SeaWorld.

14019 Pecan Orchard Drive, Winter Garden

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