Westside Village Homes with Pool Community Features

Welcome to Westside Village, an enchanting subdivision nestled in the heart of Windermere, Florida, within the picturesque Orange County. This charming community perfectly blends modern living with the serene beauty of nature, making it an ideal place for families and individuals alike.

Westside Village is renowned for its stunning homes, many of which feature private pools that invite you to indulge in Florida’s sunny climate year-round. Picture yourself lounging by your poolside oasis, sipping a refreshing drink while enjoying the gentle breeze and the sounds of nature all around. The homes in this community boast contemporary designs and spacious layouts, providing the perfect backdrop for both relaxation and entertaining.

Beyond the allure of the homes, Westside Village offers a wealth of community features that enhance the living experience. Residents can enjoy beautifully landscaped common areas, walking trails, and recreational parks, making it easy to embrace an active lifestyle. The community fosters a friendly atmosphere where neighbors become friends, and families can thrive together.

Located just a short drive from Windermere's vibrant downtown, Westside Village provides convenient access to shopping, dining, and top-rated schools. Whether you’re exploring local boutiques or enjoying a meal at one of the many delightful restaurants, you’ll find that everything you need is within reach.

In Westside Village, you’re not just buying a home; you’re investing in a lifestyle. Come discover the charm and warmth of this beautiful community, where your dream home with a pool awaits!

Newest Westside Village Homes with Pool Community Features

$1,159,000

4 Beds ⋅ 4 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code

Beautifully upgraded 4-bedroom residence featuring a thoughtfully designed floor plan, custom finishes, and exceptional indoor-outdoor living. The main level offers a private en-suite bedroom, ideal for guests or multigenerational living, along with a dedicated home office, spacious living areas, and a beautifully designed custom kitchen featuring tailored cabinetry, a large center island, integrated lighting, and generous storage. A separate TV/media room provides the perfect space for movie nights, entertainment, or relaxing with family. Upstairs, the spacious primary suite offers a private retreat with a truly special feature: Disney fireworks can be enjoyed right from the comfort of your bed. The suite also includes a generous walk-in closet and a spa-inspired primary bathroom featuring a freestanding soaking tub, dual vanities, and an oversized shower with separate his-and-hers shower fixtures. Extensive custom details can be found throughout the home, including Italian wallpaper, custom window treatments, bespoke cabinetry, decorative wall paneling, wood accents, designer lighting, and integrated LED lighting. Every element has been thoughtfully selected to create a comfortable contemporary interior. Designed for the Florida lifestyle, the outdoor living space features a spacious covered lanai with plenty of room for dining and lounging, overlooking the private heated pool and landscaped backyard. The seamless connection between the indoor and outdoor spaces makes this home equally suited for everyday living and entertaining. With a first-floor en-suite bedroom, dedicated office, media room, custom-designed kitchen, extensive interior upgrades, heated pool, and Disney fireworks views from the primary suite, this home offers an exceptional combination of style, comfort, and functionality. Thoughtfully customized and beautifully maintained, this is a home designed to be enjoyed inside and out.

12989 Westside Village Loop, Windermere

$499,990

4 Beds ⋅ 3 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code

Luxury Living in the Heart of Windermere! Welcome to this beautifully maintained 4 bedrooms and 2.5 bathrooms, single family home, located in the highly desirable community of Windermere. Situated on a charming alley-style streetscape, this elegant property offers the perfect blend of comfort, style, and convenience in one of Central Florida’s most sought-after locations. This spacious home features an open and functional floor plan with abundant natural light, generous living and dining areas, and thoughtfully designed spaces ideal for both everyday living and entertaining. Enjoy a fresh updated feel with NEW interior paint and NEW exterior paint, brand NEW carpets, NEW A/C(replaced in 2026) system, enhancing both the beauty and curb appeal of the home. The kitchen offers ample cabinetry, modern appliances, and a functional layout overlooking the main living area. The primary suite provides a relaxing private retreat with an en-suite bathroom and spacious closet space, while additional bedrooms flexibility for family, guests, or a home office. Enjoy outdoor Florida living with a private patio/backyard area perfect for relaxing or hosting gatherings. The community features beautifully maintained surroundings and convenient access to nearby parks, walking trails, and recreational areas. Ideally located just minutes from shopping, dining, top-rated schools, major highways, and world-famous attractions, including nearby Walt Disney World Resort. Easy access to Orlando, Winter Garden, and surrounding areas makes this an exceptional opportunity for homeowners seeking both convenience and lifestyle. Don’t miss your opportunity to own this beautiful Windermere home—schedule your private showing today!

7867 Berkshire Oak Alley, Windermere

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