Windermere Homes with Courtyard Architectural style

Welcome to Windermere, Florida—a picturesque gem nestled in the heart of Orange County. Known for its charming small-town atmosphere and stunning natural beauty, Windermere offers a unique blend of serenity and sophistication. With its tranquil lakes, lush landscapes, and vibrant community, it’s no wonder that Windermere has become a sought-after destination for families and professionals alike.

One of the most distinctive features of Windermere’s architectural landscape is the prevalence of homes designed in the Courtyard style. These enchanting residences are characterized by their thoughtful layouts, which often center around a private courtyard. This design not only enhances privacy but also creates a serene outdoor oasis, perfect for entertaining guests or enjoying quiet moments with family. Imagine sipping your morning coffee surrounded by blooming gardens and the gentle sounds of nature.

The Courtyard architectural style is synonymous with elegance and functionality, featuring open floor plans that seamlessly blend indoor and outdoor living spaces. High ceilings, large windows, and ample natural light are hallmarks of these homes, making them feel airy and inviting. Many Courtyard homes also boast luxurious amenities, such as gourmet kitchens, spacious master suites, and cozy outdoor fireplaces, ensuring that every comfort is at your fingertips.

Living in Windermere means embracing a lifestyle rich in community spirit, with top-rated schools, boutique shops, and delightful dining options just a stone's throw away. Explore the enchanting streets, enjoy the local parks, and immerse yourself in the vibrant culture that makes Windermere not just a place to live, but a place to thrive. Discover your dream home in this idyllic Florida enclave today!

Newest Windermere Homes with Courtyard Architectural style

$2,500,000

6 Beds ⋅ 4 Baths ⋅ Gotha Town SubDv. ⋅ 34786 Zip Code

MULTI-GENERATIONAL LUXURY LAKEFRONT LIVING. Welcome to 1629 Hempel Avenue, a private lakefront retreat set on more than one gated acre along Lake Olivia, an approximately 88-acre, spring-fed lake with private access. Located in the desirable Gotha/Windermere area, this exceptional property offers rare peace and privacy while remaining convenient to Southwest Orlando’s renowned theme parks, premier shopping, Downtown Orlando, Orlando International Airport, highly regarded schools, and the Florida Turnpike. Mature trees, lush gardens, and thoughtfully designed outdoor spaces create a setting that feels secluded, established, and distinctly Florida. An antique church door provides a memorable entrance, setting the tone for a residence that blends refined finishes, distinctive character, and comfortable everyday living. The main residence features four bedrooms, two full bathrooms, and an expansive open-concept living area designed for entertaining while showcasing beautiful lake views. The oversized great room offers multiple gathering spaces, including a billiards area, a large television and game-day space, a generous dining area, and an impressive chef-inspired kitchen. At the center of the kitchen is an abundant quartz-topped island offering extensive workspace, seating, and a natural gathering place where guests can connect while meals are prepared. High-end flooring throughout the main home includes polished ceramic tile, travertine, and solid wood, while newer energy-efficient windows and doors enhance comfort and efficiency. The primary suite is a magazine-worthy addition created as a private lakeside sanctuary. Cathedral ceilings, polished ceramic tile flooring, expansive lake views, and a flexible sitting or exercise area create an open and relaxing environment. Two oversized custom closets provide exceptional storage. The luxurious bathroom features floor-to-ceiling ceramic tile, quartz countertops, an oversized porcelain soaking tub, and a spacious walk-in shower room. Four distinctive outdoor living areas invite you to enjoy the property throughout the year. Gather around the fire in the stone-paver garden area, relax within the private walled courtyard surrounded by potted plants and the soothing sound of a water fountain, or spend the day along the expansive backyard and private boat dock. The recently updated infinity-edge pool and heated spa overlook the lake, creating a resort-style setting for relaxing, entertaining, and enjoying unforgettable sunsets. A separate guest residence adds tremendous flexibility and privacy. Complete with two bedrooms, two bathrooms, a kitchen, and a living area, it is ideal for multigenerational living, extended guests, or an on-site caretaker. A private gated driveway and abundant parking accommodate multiple vehicles with ease. Combining two complete residences, more than an acre of lakefront land, exceptional outdoor living, mature landscaping, and private access to Lake Olivia, this one-of-a-kind estate offers a lifestyle rarely available in Central Florida.

1629 Hempel Avenue, Windermere

$2,250,000

5 Beds ⋅ 4 Baths ⋅ Waterford Pointe Ph 02 Rep SubDv. ⋅ 34786 Zip Code

One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita, Lake Access & an Exceptional Seller Incentive: Up to $36,000 Toward a Rate Buy-Down or Buyer Closing Costs. A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the property combines architectural presence, exceptional privacy, and resort-inspired living in a peaceful enclave known for estate-sized homes, mature landscaping, and private access to Lake Roberts. Designed around a dramatic courtyard pool, the home creates a true indoor-outdoor lifestyle experience, ideal for both grand entertaining and everyday living. The detached guest casita is a standout feature, offering exceptional flexibility for guests, private office use, wellness retreat, creative studio, or evolving lifestyle needs. Inside, soaring ceilings, polished marble tile flooring, detailed crown molding, and dramatic two-story living spaces create a sense of scale and elegance throughout. The thoughtfully updated chef’s kitchen is designed for gathering, featuring quartz countertops, an oversized island, premium KitchenAid and Bosch appliances, double ovens, wine refrigeration, and seamless connection to the expansive family room with custom built-ins and fireplace. The private first-floor primary suite serves as a true retreat, offering direct courtyard and pool access, a spacious custom walk-in closet, and a beautifully appointed bath with dual vanities, jetted soaking tub, and walk-in shower. A second first-floor suite provides ideal accommodations for guests or family. Upstairs, expansive, flexible living spaces include a large game room overlooking the courtyard, a dedicated office with custom built-ins, a private fitness room with balcony access, and additional secondary bedrooms thoughtfully arranged for privacy and functionality. Outdoor living is equally compelling, with a screened resort-style saltwater pool and heated spa with waterfall, covered summer kitchen, multiple entertaining spaces, and the privacy that only a homesite of this scale can provide. Waterford Pointe residents enjoy an exceptional lifestyle with private access to Lake Roberts, a waterfront clubhouse, tennis courts, playground, and beautifully tree-lined streets—all within one of Windermere’s most desirable gated communities. Additional highlights include a 4-car garage, a new whole-house generator, three HVAC systems, a newly painted exterior courtyard, and highly regarded local schools. For buyers seeking privacy, architectural character, flexible living, and established Windermere luxury—without the premium of direct lakefront pricing—this is a compelling opportunity. **Private tours available by appointment**

2068 Roberts Point Drive, Windermere

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