Windsor Island Resort Real Estate

Windsor Island Resort Real Estate

Welcome to Windsor Island Resort, an enchanting community nestled in the heart of sunny Florida, where modern luxury meets the charm of resort-style living. This exclusive subdivision offers an unparalleled lifestyle, perfect for families, vacationers, and investors alike.

Windsor Island Resort is strategically located just minutes away from Orlando’s world-renowned attractions, including Walt Disney World, Universal Studios, and SeaWorld. This prime location ensures that residents can enjoy the excitement of theme parks while returning to the tranquility of their serene community.

The subdivision boasts an array of stunning single-family homes, designed with comfort and style in mind. Each residence features contemporary architecture, spacious floor plans, and high-end finishes, providing the perfect backdrop for creating lasting memories. With options ranging from cozy three-bedroom homes to expansive six-bedroom retreats, there’s a perfect fit for every lifestyle.

Beyond the beautiful homes, Windsor Island Resort offers an impressive selection of amenities that elevate everyday living. Residents can bask in the Florida sun at the resort-style pool, challenge friends to a game of volleyball, or unwind in the luxurious clubhouse. The community also features a state-of-the-art fitness center, walking trails, and playgrounds, ensuring that there’s something for everyone to enjoy.

With a focus on community and connection, Windsor Island Resort is more than just a place to live; it’s a vibrant lifestyle where neighbors become friends and memories are made. Come discover the charm of Windsor Island Resort, where your dream home awaits in the heart of Florida’s paradise!

Newest Listings in Windsor Island Resort

$611,777
6 Beds ⋅ 5 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
Windsor Island Resort investment opportunity with an exceptional location just STEP FROM THE CLUBHOUSE! This fully furnished vacation home combines resort convenience with a private setting and NO REAR NEIGHBORS TO INTERRUPT THE PEACEFUL ENJOYMENT. The elevated lot and extended lanai create an inviting outdoor retreat, complete with a private hot tub and views toward Disney fireworks. Inside, the home features themed bedrooms, a versatile gaming loft, spacious bedrooms, quality furnishings, no carpet anywhere, and a beautifully appointed kitchen with striking cabinetry and dining space. Located in Windsor Island Resort, a short-term-rental-resort community in Davenport, the property offers access to an impressive collection of amenities including a heated zero-entry pool, lazy river, dual waterslides, splash pad, mini golf, fire pit, fitness center, pickleball, basketball, volleyball, private cabanas, The Blue Marlin restaurant and the Aloha Clubhouse. The community is conveniently located near I-4, Central Florida's major attractions, shopping, dining and entertainment. Tampa, Orlando International Airport (MCO), shopping, dining, and Florida's beautiful Gulf and Atlantic Coast beaches, cruise ports and NASA. Additional features include an exterior security camera system and glass-break protection. The property is offered fully furnished, providing a turnkey option for buyers seeking a vacation home or short-term rental property in the Orlando area. The monthly assessment includes community operations and maintenance, professional on-site management, clubhouse and resort amenity operations, landscaping and irrigation, valet trash and litter pickup, bulk cable and internet, 24-hour manned entry gate and roving patrol services. A distinctive Windsor Island property offering resort amenities, a private outdoor setting and convenient access to Central Florida's tourism corridor. Don't miss this one, schedule your viewing today!

1707 Kona Lane, Davenport
$925,000
10 Beds ⋅ 8 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
Unbeatable location! This is the closest 10-bedroom home to the resort-style clubhouse in Windsor Island Resort—just a 3-minute walk away! Truly the best spot in the entire community, offering unmatched convenience for guests and exceptional rental appeal. This beautifully upgraded and fully furnished 10-bedroom, 8-bathroom pool home is a rare find. The owner invested over $140,000 in custom upgrades and high-end finishes to make this home stand out. From designer lighting and accent walls to luxury flooring and themed bedrooms, every detail was thoughtfully selected for style and comfort. Enjoy a spacious open-concept layout with an oversized granite island, stainless steel appliances, and generous living and dining areas that flow seamlessly to the covered lanai and screened-in pool—perfect for entertaining or relaxing after a long day at the parks. The owner’s suite features direct pool access and a spa-style bath with dual vanities. Multiple en-suite bedrooms provide privacy and convenience, while creatively themed kid rooms deliver that “wow” factor for vacation guests. Located in the highly desirable Windsor Island Resort, just minutes from Disney, with top-tier amenities including a lazy river, water park, mini golf, arcade, fitness center, and more. Whether you're seeking a premium vacation home or a high-performing investment property, this is the best-located, most upgraded 10-bedroom home in the community—sold fully furnished and full rental-ready.

1978 Summer Drive, Davenport
$399,800
5 Beds ⋅ 5 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
Short Sale. Welcome to this fully furnished, turnkey 5-bedroom, 4.5-bathroom home located in the highly desirable gated Windsor Island Resort! With short-term rentals allowed, this property is ideal as a vacation home, investment opportunity, or personal getaway. The home features a bright open-concept layout with a modern kitchen, stainless steel appliances, and spacious living and dining areas perfect for entertaining. A convenient downstairs bedroom and bathroom provide added flexibility for guests, while the private pool offers the perfect place to relax. Upstairs, you'll find a versatile loft/game room and four additional bedrooms, including a spacious primary suite and a third bedroom with its own ensuite bathroom. Windsor Island Resort offers an incredible selection of amenities, including a resort-style pool, lazy river, water slides, mini golf, cabanas, bar, volleyball, cornhole, and a fire pit with theme park views. The HOA includes internet, cable, lawn care, and daily trash service, making ownership and vacation stays even more convenient. Ideally located just minutes from Disney, shopping, dining, golf, and the airport, this home offers the perfect combination of comfort, entertainment, and resort-style living!

207 Jetty Way, Davenport
$799,999
10 Beds ⋅ 8 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
Step into paradise at 3621 Lily Ln, a breathtaking turn-key estate located within the highly sought-after, guard-gated Windsor Island Resort community. Perfect as an incredible income generator or an unforgettable multi-family retreat, this grand 10-bedroom, 8-bathroom residence comes fully furnished and professionally decorated, offering effortless luxury from day one. Unwind on your private, screened-in lanai featuring a sparkling heated pool and spa—the ultimate setting for outdoor relaxation and entertaining. Inside, the home excels at delivering unforgettable experiences, anchored by a custom garage-turned-game room designed to keep guests and family entertained for hours. Beyond your private sanctuary, residents and guests enjoy exclusive access to Windsor Island Resort’s world-class resort amenities. The iconic Aloha Clubhouse serves as the heart of the community, boasting a zero-entry pool, lazy river, dual waterslides, splash pad, 9-hole mini-golf, arcade, state-of-the-art fitness center, sand volleyball, and an on-site poolside bar and grille. Unbeatably located just minutes from Central Florida’s top destinations—including Walt Disney World, Universal Orlando, premier golf, fine dining, and endless shopping—this property seamlessly blends luxury living with unmatched short-term rental investment potential.

3621 Lily Lane, Davenport
$485,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
TURNKEY VACATION HOME IN WINDSOR ISLAND RESORT – FULLY FURNISHED & READY TO GENERATE INCOME Experience the perfect blend of luxury, comfort, and investment potential at 197 Jetty Way, an exceptional 5-bedroom, 4.5-bathroom townhome located within the prestigious Windsor Island Resort—one of Central Florida’s most desirable vacation rental communities. Sold fully furnished and professionally decorated, this move-in-ready property is ideal as a personal vacation retreat or a high-performing short-term rental from day one. The thoughtfully designed floor plan features a convenient first-floor guest suite, a spacious upstairs loft that serves as an additional entertainment area, and a private screened lanai where guests can unwind after enjoying everything Central Florida has to offer. The open-concept living spaces are designed to accommodate families and larger groups comfortably, combining modern finishes, stylish décor, and functional living areas to create an unforgettable vacation experience. This home offers an excellent location within the community, allowing you to walk to the clubhouse and resort amenities with ease. The private lanai faces south, providing all-day sun exposure, and offers enhanced privacy with a high rear wall and no rear neighbors—perfect for relaxing in a peaceful and secluded setting. As part of Windsor Island Resort, owners and guests enjoy access to an impressive collection of resort-style amenities, including multiple swimming pools, a lazy river, splash park, fitness center, miniature golf, tennis and basketball courts, clubhouse, poolside bar, arcade, and numerous recreational activities for all ages. Conveniently located just minutes from Walt Disney World, Universal Orlando Resort, championship golf courses, shopping, dining, and major highways, this property offers outstanding convenience for both vacationers and owners. Whether you're searching for a turnkey investment property, a second home, or a vacation residence that offers excellent income potential and long-term appreciation, this beautifully maintained home is an outstanding opportunity. Schedule your private tour today and discover everything this exceptional Windsor Island Resort property has to offer.

197 Jetty Way, Davenport
$750,000
7 Beds ⋅ 6 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
Welcome to this spacious luxury home in the exclusive Windsor Island Resort, offering the perfect combination of comfort, style, and an unbeatable location. Just minutes from Orlando's world-famous theme parks, shopping, restaurants, and entertainment.Recently updated with fresh renovations and a newly installed solar energy system, the home features professionally designed themed bedrooms that create a fun and memorable experience for guests of all ages.Multiple inviting living areas, a cozy loft, and a gourmet kitchen fully equipped with modern appliances, cookware, and everything needed to prepare breakfast, lunch, or dinner with ease.Adjacent to the kitchen is a generous dining area with seating for everyone, plus additional seating at the stylish breakfast bar.Open the sliding glass doors to create a seamless indoor-outdoor living space. Step onto the covered lanai featuring alfresco dining, comfortable lounge seating, and a beautiful private resort-style pool and spa overlooking the peaceful lake—your own private oasis for relaxation.Enjoy the Windsor Island Resort's outstanding amenities, including a spectacular resort-style clubhouse, a large community pool, a complimentary arcade room, fitness center, waterslides, and many more family-friendly attractions.

1897 Summer Drive, Davenport
$409,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
MOTIVATED SELLER! Experience resort-style living in this beautifully maintained, fully furnished 5-bedroom, 4.5-bath Windsor Island townhome, lightly used exclusively as a personal vacation retreat and never subjected to the heavy wear of short-term rental turnover. With spacious en-suite bedrooms, a versatile loft area, and room for everyone to relax comfortably, this home is perfectly designed for both personal enjoyment and entertaining guests. Inside, you’ll find a bright open-concept floorplan featuring tile flooring throughout the main living areas, a spacious kitchen with granite countertops, stainless steel appliances, and a large center island ideal for gathering. The living and dining spaces flow seamlessly together and open through sliding glass doors to your private screened lanai and plunge pool, creating the perfect indoor-outdoor Florida lifestyle. The thoughtfully designed layout also includes an upstairs laundry room, generous storage, and plenty of parking for owners and guests alike. Located within the highly sought-after gated Windsor Island Resort community, residents and guests enjoy access to exceptional resort amenities including a zero-entry pool, lazy river, dual water slides, splash pad, poolside bar, fitness center, arcade, mini golf, playground, and an impressive clubhouse. Ideally situated near world-famous theme parks, championship golf courses, shopping, dining, major highways, and Orlando International Airport, this property offers an outstanding opportunity as a vacation home, investment property, or full-time Florida retreat.

297 Jetty Way, Davenport
$719,000
7 Beds ⋅ 6 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
LOCATION! LOCATION! LOCATION! EXCELLENT BOOKING HISTORY AND FUTURE BOOKINGS CAN CONVEY! Just a few steps from the fabulous clubhouse! Welcome to 1806 Summer Drive in Davenport — a stunning 7-bedroom, 5.5-bathroom CORNER LOT home designed to impress and built for unforgettable experiences. EXCELLENT BOOKING HISTORY AND FUTURE BOOKINGS CAN CONVEY ! Whether you’re looking for a high-performing short-term rental or a spacious vacation retreat, this property offers the perfect blend of comfort, style, and entertainment. Step inside to discover expansive living areas filled with natural light, an open-concept layout ideal for gatherings, and beautifully appointed bedrooms — including incredible themed rooms inspired by Frozen and Spider-Man that will delight guests of all ages. The garage was transformed in an espetacular GAME ROOM inspired by the Justice League movie where guests of all ages can play and enjoy the atmosphere. The private screened-in pool provides the perfect Florida oasis for relaxing under the sun, while the dedicated game room adds even more entertainment value for family and visitors. With generous bedroom space and multiple bathrooms, this home comfortably accommodates large groups with ease. Located just minutes from world-renowned attractions, shopping, dining, and major highways, this property offers convenience and strong rental appeal. Don’t miss the opportunity to own a turn-key home that combines luxury, fun, and investment potential all in one.

1806 Summer Drive, Davenport
$499,900
5 Beds ⋅ 5 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
LOCATION! LOCATION!LOCATION! Just a few steps from the fantastic clubhouse! Beautiful 5-bedroom, 5.5-bath home in the highly desirable Windsor Island Resort. Fully furnished and professionally decorated, this property includes themed bedrooms, elegant finishes, and a private heated pool for the ultimate Florida lifestyle. Perfect as a vacation home or short-term rental investment, it is turnkey and ready to enjoy. Windsor Island features exceptional resort-style amenities such as a water park, lazy river, clubhouse, mini golf, fitness center, and more—all just minutes from Disney. A truly exceptional opportunity in one of Central Florida’s most sought-after communities. Don’t miss this exceptional opportunity—schedule your visit today!

1320 Lava Tree Dr, Davenport
$899,999
8 Beds ⋅ 6 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
Imagine stepping into the ultimate vacation home, a place where every detail is designed for unforgettable family getaways and incredible returns. Welcome to 3520 Lavender Drive, a fully furnished, 8-bedroom, 6-bathroom oasis located in the heart of Windsor Island Resort. This isn't just a house; it's a turnkey investment property ready to impress. Guests enjoy the Florida sun from their private, screened-in pool and spa, or gather for movie night in the spacious upstairs loft. The excitement continues with uniquely themed bedrooms that transport kids and adults alike into a world of pure fun. Beyond the front door, a world-class resort awaits. Windsor Island Resort is a gated paradise with a zero-entry main pool, a thrilling lazy river, and high-energy water slides. Guests can challenge each other on the mini-golf course and sports courts or unwind by the fire pit or in the peaceful hammock garden. The clubhouse features a state-of-the-art game room, while the poolside bar and grill offers the perfect spot for a casual meal. Best of all, this prime location is just a short drive from Orlando’s world-famous attractions, including Walt Disney World, as well as endless dining, shopping, and entertainment options. This is your chance to own a highly desirable, high-earning property in Central Florida's premier vacation destination.

3520 Lavender Drive, Davenport
$899,000
8 Beds ⋅ 6 Baths ⋅ Windsor Island Resort SubDv. ⋅ 33897 Zip Code
Welcome to your Florida dream home! Located just 5 miles from Walt Disney World and 15 miles from Universal Orlando, this sprawling 8-bedroom, 6-bathroom estate offers over 4,000 square feet of beautifully upgraded living space, perfect for vacation rental investors, second-home seekers, or full-time residents who want it all. Step inside to find an open-concept layout with a huge loft, a fully-equipped game room, and a gourmet kitchen packed with high-end finishes. With over $150,000 in upgrades, no detail has been spared — from modern flooring and premium countertops to designer fixtures and smart home features. Out back, enjoy the screened-in private pool and lanai with no rear neighbors, providing ultimate privacy and tranquility after a day at the parks. Located in a resort-style community, you’ll also have access to world-class amenities including a waterpark-style pool area, on-site restaurant, spa, and fitness center — all just steps from your door. Whether you’re hosting guests or relaxing with family, this home delivers the perfect blend of space, luxury, and location.

2090 Lelani Circle, Davenport
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