Winter Garden/Oakland Homes with Mid-Century Modern Architectural style

Winter Garden/Oakland Homes with Mid-Century Modern Architectural style

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant area is celebrated for its rich history, picturesque landscapes, and a strong sense of community. Just a stone's throw from the bustling city of Orlando, Winter Garden offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and everyone in between.

One of the most captivating features of this region is its architectural charm, particularly the stunning Mid-Century Modern homes that grace its streets. These homes, characterized by their clean lines, large windows, and open floor plans, embody a timeless elegance that appeals to both design enthusiasts and casual admirers alike. With an emphasis on bringing the outdoors in, Mid-Century Modern architecture seamlessly integrates with the lush Florida landscape, creating a serene living environment that feels both spacious and inviting.

As you stroll through the neighborhoods of Winter Garden and Oakland, you'll be captivated by the unique character of each home, many of which have been lovingly preserved or thoughtfully updated to reflect modern comforts while maintaining their iconic style. The local community is vibrant and welcoming, with farmers' markets, quaint shops, and delightful dining options that embody the charm of small-town living.

Whether you're looking to buy your dream home or simply explore the beauty of this remarkable area, Winter Garden and Oakland offer a unique lifestyle that harmonizes history, architecture, and community spirit. Discover the allure of Mid-Century Modern homes in this picturesque Florida gem today!

Newest Winter Garden/Oakland Homes with Mid-Century Modern Architectural style

$525,090
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Under Construction. Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Benton bungalow, a brand-new home that includes 3 spacious bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator. White cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite, two additional bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a frameless glass-enclosed shower, quartz-topped dual vanity, and linen closet. Throughout the first floor, enjoy the beauty of Wood-Look Luxury Vinyl Plank flooring, while tile enhances the laundry room and bathrooms. Plush, stain-resistant Shaw carpet covers the stairs and bedrooms, adding comfort and style. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

16827 Evermore Alley, Winter Garden
$2,500,000
6 Beds ⋅ 7 Baths ⋅ Lakeshore Preserve Ph 4 SubDv. ⋅ 34787 Zip Code
This extraordinary lake-view residence redefines luxury, comfort, and sophistication in the heart of Winter Garden. Located in the highly sought-after Lakeshore Preserve community, this stunning home impresses from the moment you arrive with an elegant paved driveway, beautifully manicured landscaping, and grand double entry doors leading into a dramatic two-story foyer with soaring ceilings and an unforgettable first impression. Designed for exceptional living and entertaining, the home features a sophisticated open-concept floor plan filled with abundant natural light and breathtaking lake views that create a serene and picturesque atmosphere throughout the property. The elegant dining area showcases stunning views of the pool and lake, creating the perfect setting for memorable gatherings with family and friends. The gourmet kitchen is truly a chef’s dream, featuring granite countertops, a spacious center island with seating, stainless steel appliances, designer tile backsplash, and a large walk-in pantry with custom built-in shelving. Overlooking the expansive living room, the space is enhanced by tray ceiling details and elegant recessed lighting, offering both warmth and sophistication. Sliding glass doors seamlessly connect the indoor and outdoor living spaces, opening to a spectacular pool deck and outdoor gourmet area designed for the ultimate Florida lifestyle. Relax while enjoying peaceful water views from your private backyard oasis — the perfect place to entertain, unwind, and enjoy Florida sunsets over the lake. The luxurious primary suite serves as a private retreat, featuring a spa-inspired bathroom with modern square sinks, a soaking tub, and a spacious walk-in rain shower. A separate laundry room provides ample cabinetry and additional storage for convenience and organization. Residents of Lakeshore Preserve enjoy outstanding resort-style amenities, including a clubhouse, resort-style swimming pool, fitness center, yoga room, playgrounds, dog park, sand volleyball court, fishing pier, and community canoes and kayaks. The HOA also maintains the community common areas, allowing for a truly low-maintenance lifestyle. Ideally located just minutes from Orange County National Golf Center, Walt Disney World Resort, premier shopping, dining, top-rated schools, and major highways, this impeccably maintained lakefront-inspired home offers the perfect combination of luxury, convenience, and lifestyle. A rare opportunity to own an exceptional lake-view home in one of Winter Garden’s most desirable communities.

15505 Shorebird Lane, Winter Garden
$249,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Experience resort-style living and income potential at its finest in this fully furnished, turnkey 2-bedroom, 2-bath condo-hotel residence located at The Grove Resort & Spa Orlando. UNIT 2615 features an open-concept floor plan with luxury vinyl plank flooring, a modern kitchen with quartz countertops and stainless-steel appliances, and a private balcony overlooking tranquil conservation and water views. The spacious primary suite offers a true retreat with a spa-inspired ensuite bathroom, while the thoughtfully designed layout comfortably sleeps up to 8 guests, making it ideal for personal use, vacation stays, or investment. Offered fully furnished, this residence is truly move-in or rent-ready. As a 4-star resort and Walt Disney World® Good Neighbor Hotel, the property boasts world-class amenities including three resort pools, two on-site restaurants, a full-service spa, state-of-the-art fitness center, arcade/game room, and private access to Lake Austin. Owners and guests enjoy FREE shuttle service to the theme parks, plus exclusive access to the on-site Surfari Water Park, featuring a lazy river, poolside restaurant and bar, and the exhilarating FLOWRIDER® double surf simulator. Conveniently located less than 5 miles from Walt Disney World® Resort and just 3.9 miles from Flamingo Crossings Town Center with over 40 shops and restaurants, this property delivers unbeatable proximity to Central Florida’s top attractions. This condo- hotel residence also includes access to an on-site, in-house rental management program, providing rental income when not in personal use, along with VIP owner check-in privileges. ALL utilities, cable, and internet are included in the monthly maintenance, offering exceptional convenience and value. An outstanding opportunity for a vacation home, second residence, or income-producing investment in the heart of Orlando’s premier resort corridor

14501 Grove Resort Avenue Unit 2615, Winter Garden
$299,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Experience resort-style living and income potential at its finest in this fully furnished, turnkey 2-bedroom, 2-bath condo-hotel residence located at The Grove Resort & Spa Orlando. UNIT 3524 features an open-concept floor plan with luxury vinyl plank flooring, a modern kitchen with quartz countertops and stainless-steel appliances, and a private balcony overlooking tranquil conservation and water views. The spacious primary suite offers a true retreat with a spa-inspired ensuite bathroom, while the thoughtfully designed layout comfortably sleeps up to 8 guests, making it ideal for personal use, vacation stays, or investment. Offered fully furnished, this residence is truly move-in or rent-ready. As a 4-star resort and Walt Disney World® Good Neighbor Hotel, the property boasts world-class amenities including three resort pools, two on-site restaurants, a full-service spa, state-of-the-art fitness center, arcade/game room, and private access to Lake Austin. Owners and guests enjoy FREE shuttle service to the theme parks, plus exclusive access to the on-site Surfari Water Park, featuring a lazy river, poolside restaurant and bar, and the exhilarating FLOWRIDER® double surf simulator. Conveniently located less than 5 miles from Walt Disney World® Resort and just 3.9 miles from Flamingo Crossings Town Center with over 40 shops and restaurants, this property delivers unbeatable proximity to Central Florida’s top attractions. This condo- hotel residence also includes access to an on-site, in-house rental management program, providing rental income when not in personal use, along with VIP owner check-in privileges. ALL utilities, cable, and internet are included in the monthly maintenance, offering exceptional convenience and value. An outstanding opportunity for a vacation home, second residence, or income-producing investment in the heart of Orlando’s premier resort corridor

14501 Grove Resort Avenue Unit 3524, Winter Garden
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