Windsor Island Resort Real Estate

Windsor Island Resort Real Estate

Welcome to Windsor Island Resort, a stunning vacation community nestled in the heart of Davenport, Florida. This exquisite subdivision offers an unparalleled blend of luxury living and resort-style amenities, making it the perfect destination for families, retirees, or anyone seeking a slice of paradise.

Windsor Island Resort boasts a prime location just minutes away from the world-renowned attractions of Orlando, including Walt Disney World, Universal Studios, and SeaWorld. The community is designed with a focus on leisure and relaxation, featuring beautifully landscaped grounds, picturesque walking trails, and an array of recreational facilities. Residents and guests can enjoy a sparkling resort-style pool, a state-of-the-art fitness center, and a vibrant clubhouse that serves as the social hub of the neighborhood.

The homes in Windsor Island Resort are thoughtfully designed, offering spacious floor plans that cater to modern living. With a variety of architectural styles and sizes, there’s something to suit every taste and lifestyle. Many homes come equipped with private pools, large patios, and open-concept living spaces, perfect for entertaining family and friends.

In addition to its stunning homes and fantastic amenities, Windsor Island Resort is conveniently located near shopping, dining, and outdoor activities. Whether you’re looking to explore the nearby golf courses, indulge in retail therapy at local boutiques, or savor delicious cuisine at nearby restaurants, you’ll find everything you need just a stone’s throw away.

Experience the magic of Windsor Island Resort, where the charm of Florida living meets the excitement of a vacation lifestyle. Come and discover your dream home in this enchanting community today!

Newest Listings in Windsor Island Resort

$750,000
7 Beds ⋅ 6 Baths ⋅ O6425539 MLS
Don't miss GEM.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. 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.Adjacent to the kitchen is a generous dining area with seating for everyone, plus additional seating at the stylish breakfast bar.Most of the rooms have been designed as stunning themed rooms, each with a unique style, while the garage has been transformed into a magnificent game room.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 —your own private oasis for relaxation.Just minutes walk to the Windsor Island Resort clubhouse. Enjoy the 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.

1891 Summer Drive, Davenport

Listing courtesy of TOPSKY REALTY INC. 407-476-6189
$495,000
5 Beds ⋅ 5 Baths ⋅ O6425220 MLS ⋅ 197 BLDG.
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

Listing courtesy of FLORIDA CONNEXION PROPERTIES. 407-574-2636
$750,000
7 Beds ⋅ 6 Baths ⋅ O6423233 MLS
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

Listing courtesy of TOPSKY REALTY INC. 407-476-6189
$419,900
5 Beds ⋅ 5 Baths ⋅ O6406854 MLS ⋅ 4 BLDG.
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

Listing courtesy of REDFIN CORPORATION. 407-708-9747
$719,000
7 Beds ⋅ 6 Baths ⋅ O6383749 MLS
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

Listing courtesy of FLORIDA SCANDI REALTY LLC. 407-982-7224
$720,000
7 Beds ⋅ 6 Baths ⋅ O6359800 MLS
Welcome to an exceptional income-producing home located in the highly sought-after, guard-gated Windsor Island Resort in Davenport, Florida. This fully furnished 7-bedroom, 5.5-bathroom vacation pool home delivers an outstanding combination of luxury, comfort, and prime proximity to Orlando’s world-famous attractions. Ideal as an investment property or a personal getaway, this residence stands out for its thoughtful design and turn-key convenience. Step inside to a bright and spacious open floor plan perfect for hosting and accommodating large groups. The first-floor primary suite offers added privacy and convenient access for owners or guests. The home’s gathering spaces flow seamlessly into the modern kitchen, showcasing sleek cabinetry, stone countertops, stainless steel appliances, and a large island overlooking the living and dining areas. Upstairs features multiple ensuite bedrooms, themed guest rooms, and a generous loft that provides flexible space for entertainment, relaxation, or additional sleeping options. The layout is designed to comfortably support multi-family stays and vacation groups looking for ample room. Outdoors, the private screen-enclosed heated pool and covered lanai create the ideal setting for enjoying the Florida lifestyle year-round. Situated on a desirable corner lot, the property offers extra privacy and additional outdoor space, increasing both guest satisfaction and rental desirability. Located just minutes from Disney, Margaritaville, dining, shopping, golf courses, and major highways, this home is perfectly positioned to benefit from strong short-term rental demand. Whether you are expanding your portfolio or seeking a turn-key vacation retreat, this property represents a standout opportunity in one of Central Florida’s premier resort communities.

3404 Lilac Way, Davenport

Listing courtesy of MARKET CONNECT REALTY LLC. 407-250-4708
$499,900
5 Beds ⋅ 5 Baths ⋅ O6338426 MLS ⋅ 1 BLDG.
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

Listing courtesy of FLORIDA SCANDI REALTY LLC. 407-982-7224
$899,999
8 Beds ⋅ 6 Baths ⋅ S5133131 MLS
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

Listing courtesy of TEAM DONOVAN. 407-705-2616
$520,000
5 Beds ⋅ 5 Baths ⋅ O6328021 MLS ⋅ 2b BLDG.
Welcome to 3818 Lana Ave, Davenport — an exceptional 5-bedroom, 4.5-bathroom home featuring a private screened-in pool, a game room, and professionally decorated themed bedrooms inspired by Mickey Mouse, Harry Potter, Star Wars, Frozen, and Avatar—perfect for unforgettable family moments or standout short-term rental appeal. Enjoy an open floor plan, modern kitchen, multiple en-suites, and stylish furnishings throughout. Located just minutes from Disney, golf courses, shopping, and dining, this home blends comfort, fun, and location in one turnkey package. Don’t miss out — schedule your showing today!

3818 Lana Avenue, Davenport

Listing courtesy of FLORIDA CONNEXION PROPERTIES. 407-574-2636
$989,000
8 Beds ⋅ 6 Baths ⋅ P4935392 MLS
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

Listing courtesy of 3D TEAM REALTY LLC. 407-504-9325
Start Your Search