Winter Garden/Oakland Homes with Awning(s) Exterior Features

Winter Garden/Oakland Homes with Awning(s) Exterior Features

Welcome to the charming communities of Winter Garden and Oakland, Florida! Nestled just a stone's throw from the picturesque shores of Lake Apopka, these vibrant neighborhoods offer a perfect blend of small-town charm and modern conveniences. Known for their lush landscapes and friendly atmosphere, Winter Garden and Oakland are ideal for families, retirees, and anyone seeking a serene lifestyle while being close to the excitement of Orlando.

As you stroll through the tree-lined streets, you'll discover a delightful array of homes, many featuring inviting awnings that enhance their curb appeal. These awnings not only provide shade and protection from the Florida sun but also add a touch of elegance and character to each residence. Imagine sipping your morning coffee under a cozy awning, enjoying the gentle breeze and the beauty of your surroundings.

Winter Garden boasts a rich history, evident in its beautifully preserved downtown area filled with quaint shops, delicious eateries, and a thriving farmers market. The nearby West Orange Trail offers miles of scenic paths for walking, biking, and exploring the natural beauty of the region. Oakland, with its charming historic district and serene lakes, provides a peaceful retreat just minutes away from the bustling attractions of Orlando.

Whether you're looking for a family home with a spacious yard or a cozy retreat with unique architectural features, Winter Garden and Oakland have something for everyone. Experience the warmth of the community and the allure of homes adorned with charming awnings—your dream home awaits in this idyllic corner of Florida!

Newest Winter Garden/Oakland Homes with Awning(s) Exterior Features

$239,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort & Spa SubDv. ⋅ 34787 Zip Code
Exceptional opportunity to own a spacious top-floor 3-bedroom, 3-bathroom condo at The Grove Resort & Water Park, just minutes from Walt Disney World! This fully furnished 1,544 sq. ft. “Sable” floor plan offers an ideal combination of personal vacation use and income-producing potential through The Grove’s professionally managed hotel rental program. Located on the 7th and top floor of Building 1, the condo features a spacious split-bedroom layout, three full bathrooms, a well-equipped kitchen with granite countertops, comfortable living and dining areas, and a screened balcony with elevated views. The Grove delivers the complete Orlando resort experience with Surfari Water Park featuring water slides, a lazy river, splash areas and private cabanas, multiple onsite dining options, a full-service spa, fitness center, arcade, and a 20-acre activity lake offering fishing and water activities. When you're not enjoying the condo yourself, the turnkey rental program provides professional management for vacation rentals. Whether you're looking for your own Orlando getaway or a furnished vacation rental investment near Disney, this top-floor 3-bedroom residence offers an outstanding opportunity at one of Central Florida's most amenity-rich resort destinations.

14501 Grove Resort Ave Unit 1707, Winter Garden
$930,000
5 Beds ⋅ 4 Baths ⋅ Orchard Hills Ph 3 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 5-bedroom, 3.5-bath home with a spacious 3-car garage, offering the perfect blend of comfort, style, energy efficiency, and location. From the moment you step inside, you’ll appreciate the soaring ceilings, open living spaces, and thoughtful upgrades throughout. The custom stone fireplace, bring an inviting ambiance to those cozy evenings or when entertaining guests year round. At the heart of the home is the gourmet kitchen, featuring granite countertops, built-in appliances, abundant cabinetry, and plenty of space for cooking and entertaining. The adjoining living area is highlighted by a built-in fireplace, creating a warm and inviting focal point for family gatherings. One of the home’s standout features is the fully owned solar system, helping keep monthly electric costs exceptionally low—averaging approximately $33 per month. The exterior has been recently painted, adding fresh curb appeal. Step outside to the expansive backyard designed with possibilities in mind. The generous outdoor space offers ample room to add a pool whilst still leaving plenty of space for a dedicated grilling and outdoor dining area. Whether you're hosting summer barbecues, family gatherings or relaxing with friends, the spacious yard provides the ideal setting for creating your own private outdoor retreat. The modern floor plan offers five bedrooms and 3.5 bathrooms, providing flexibility for families, guests, or a home office, along with a generous 3-car garage for vehicles and additional storage. Ideally located in one of Winter Garden’s most desirable communities, this home is zoned for highly rated schools and offers convenient access to Walt Disney World, SR-429, downtown Orlando, and Orlando International Airport (MCO), making commuting, travel, shopping, dining, and entertainment easily accessible. If you’re looking for a move-in-ready home with premium features, exceptional energy savings, generous living space, and an outstanding location, this home is ready to welcome you.

5079 Palmetto Park Drive, Winter Garden
$214,000
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Short Sale. Don't miss this beautifully updated 2-bedroom, 2-bathroom townhouse offering the perfect blend of comfort, convenience, and unbeatable location. Tucked away in a quiet community, this home is just minutes from all the charm and excitement of downtown Winter Garden, known for its boutique shopping, top-rated restaurants, farmers market, splash pad, and the scenic West Orange Trail. Inside, you'll find a thoughtfully updated interior offering easy, low-maintenance living. Perfect for first-time buyers, downsizers, or investors looking for a move-in ready property in one of Central Florida's most sought-after towns. With its prime location close to shopping, dining, parks, and major roadways, this townhouse offers an unbeatable opportunity to enjoy the best of downtown Winter Garden living without the downtown price tag. Schedule your showing today!

359 Douglas Way Unit 54, Winter Garden
$279,900
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Stunning 2-bedroom, 2-Bath condo on the second floor, 1276 sq ft, with new carpet in the bedrooms and stairs. All Appliances updated in the last few years, and the A/C is just a little over a year old. Walk to the pool, enjoy views of the retention pond, and be close to all the community amenities. Don't miss this gem?

143 Southern Pecan Circle Unit 206, Winter Garden
$1,799,000
4 Beds ⋅ 5 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code
Experience the ultimate in luxury urban living at 68 N Park Ave, a stunning 3-story townhome with rooftop deck located in the heart of Historic Downtown Winter Garden. This sophisticated 4-bedroom, 4.5-bathroom residence offers over 3,500 sq. ft. of meticulously designed space, seamlessly blending modern elegance with the charm of the historic district. The open-concept main level features soaring 11-foot ceilings, expansive industrial-style windows, and a chef’s dream kitchen equipped with an oversized quartz island, natural gas appliances, and custom artisan cabinetry. Accessibility is effortless with your own private elevator serving all floors. Retreat to the third-floor master suite, featuring a spa-inspired bath and massive walk-in closet, or host guests in the versatile first-floor bedroom suite. The "wow factor" continues on the 1,200 sq. ft. private rooftop terrace, offering panoramic views of the city skyline—the perfect spot for evening cocktails or watching local fireworks.Location is everything. Leave your car in the 2-car garage and embrace the golf-cart-friendly lifestyle. You are just steps away from: The award-winning Winter Garden Farmers Market, The vibrant Plant Street Market and Crooked Can Brewing Co, The world-class West Orange Trail for biking and running, Boutique shopping, fine dining, and the historic Garden Theatre. Don’t miss this rare opportunity to own a piece of downtown luxury. Schedule your private showing today!

68 N Park Avenue, Winter Garden
$565,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hamlin SubDv. ⋅ 34787 Zip Code
HAMLIN LOCATION + BUILT IN 2021 + 3 BEDROOMS + FIRST FLOOR FLEX ROOM! This upgraded Winter Garden home offers over 2,100 square feet of living space with the flexibility today's buyers are looking for, all just minutes from Hamlin Town Center and convenient access to SR 429. The first floor flex room adds valuable versatility and can function as a home office, playroom, guest space, or additional sleeping area depending on your needs. Inside, the open concept main living area is filled with natural light and features fresh interior paint, upgraded flooring, and updated lighting. At the center of the home, the kitchen makes an immediate impression with Level 5 quartz countertops, a large island wrapped in custom porcelain tile, stainless steel appliances, and generous cabinet space. The open layout keeps the kitchen connected to the main living areas, creating a practical setup for both everyday living and entertaining. Upstairs, the spacious primary suite includes a custom walk in closet and upgraded en suite bathroom with quartz countertops. Two additional bedrooms, a full bathroom, and an updated laundry room complete the second floor. Beyond the finishes, this home includes upgrades that add comfort, convenience, and value from day one, including a whole home water filtration and softener system, APCO X Ultra air purification system, five conveying Arlo security cameras, and prewiring for additional smart home connectivity. A rear entry two car garage and low maintenance yard complete the property. And then there is the location. Hamlin Town Center puts shopping, dining, coffee, fitness, Publix, Cinépolis Luxury Cinemas, and entertainment just minutes away. Convenient access to SR 429 also connects the area to Walt Disney World, Orlando, and other Central Florida destinations. For buyers comparing newer homes in Winter Garden and Hamlin, this property offers an appealing alternative to starting from scratch: 2021 construction, more than 2,100 square feet, flexible living space, significant upgrades already completed, and a location surrounded by the everyday conveniences that make Hamlin one of Winter Garden's most recognized destinations. SPECIAL FINANCING INCENTIVE! Qualified buyers who use our preferred lender can receive an interest rate 1% lower for the first year at no cost to the buyer. Lower rate. Lower payment. No additional cost to you. Subject to buyer qualification and lender approval. Contact the listing agent for details.

4642 Prairie Creek Street, Winter Garden
Start Your Search