Windsor Island Residence Real Estate

Windsor Island Residence Real Estate

Welcome to Windsor Island Residence, a captivating community nestled in the heart of Davenport, Florida. This enchanting subdivision is designed for those who seek the perfect blend of modern living and natural beauty. With its lush landscapes and thoughtfully crafted homes, Windsor Island Residence offers a serene retreat just minutes away from the vibrant attractions of Central Florida.

Windsor Island Residence boasts an array of stunning single-family homes, each tailored to meet the needs of families, retirees, and everyone in between. The community features spacious floor plans, contemporary designs, and top-notch amenities that cater to a lifestyle of leisure and comfort. Residents can enjoy access to a resort-style clubhouse, refreshing swimming pools, and recreational areas that invite both relaxation and social engagement.

Situated conveniently near major highways, Windsor Island Residence provides easy access to the world-renowned theme parks of Orlando, including Walt Disney World and Universal Studios. Outdoor enthusiasts will appreciate the nearby golf courses, nature trails, and lakes, perfect for weekend adventures or tranquil evenings.

The charm of Davenport complements the community, with local shops, restaurants, and parks just a stone's throw away. Families will also benefit from the highly-rated schools in the area, ensuring a nurturing environment for children to thrive.

Discover the allure of Windsor Island Residence, where your dream home awaits amidst the beauty and excitement of Florida living. Embrace a lifestyle filled with warmth, community, and endless possibilities—welcome home!

Newest Listings in Windsor Island Residence

2031 Lelani Circle, Davenport
$795,000
10 Beds ⋅ 8 Baths ⋅ O6454029 MLS
MOTIVATED SELLER! Best-priced 10-bedroom home in Windsor Island Resort! Fully furnished and ready for you to move in or start generating rental income. Discover the perfect blend of comfort, space, and resort-style living in this stunning 10-bedroom home, ideal for large families, multi-generational living, or hosting guests. The recently updated kitchen features modern conveniences, while the inviting living area provides the perfect space to relax and unwind. Enjoy a spacious, thoughtfully designed layout, abundant natural light, and your own refreshing private pool. Whether you're looking for a dream vacation home, a personal residence, or an investment opportunity, this property offers exceptional versatility and value. Windsor Island Resort features fantastic resort-style amenities, making it an ideal destination for families and guests alike. Don't miss this incredible opportunity! Call me today to schedule your private showing!

2031 Lelani Circle, Davenport

Listing courtesy of MS LAND & BUILDING LLC. 407-466-7000
920 Paradise Dr, Davenport
$459,900
5 Beds ⋅ 5 Baths ⋅ S5159467 MLS ⋅ 920 BLDG.
A blank canvas in one of the Disney area’s most sought-after resort communities. This 5-bedroom, 4.5-bath townhome, built in 2021, offers 2,293 sq ft behind a guard-gated entrance, and arrives unfurnished, which is a rare find at Windsor Island and a genuine opportunity for the right buyer. Most homes here come with someone else’s décor already decided. This one doesn’t. Whether you want to create immersive themed bedrooms that short-term rental guests will remember and rebook, or design a personal vacation retreat that feels like yours from the first night, you start with clean, well-kept rooms and your own imagination. No furniture to replace, no theming to undo, no compromises on someone else’s taste. The layout is built for how guests actually stay. The first floor includes a bedroom and full bath, ideal for visitors who prefer to avoid stairs. Upstairs you’ll find a primary suite with a walk-in closet, a second primary suite, two further bedrooms ready to be themed, and a versatile loft that works equally well as a games room, cinema space or quiet retreat. Stainless steel appliances are in place in the kitchen. Step outside to your own private screened pool, with the community’s resort amenities a short stroll away. Windsor Island Resort is known for outstanding amenities, including an 8,000 sq ft clubhouse, resort-style pool and spa, lazy river, poolside cabanas, fitness center, on-site restaurant and bar, playgrounds, sports courts, arcade and lounge areas for guests of all ages. The location gives easy access to US 192, I-4, shopping, dining, golf, supermarkets and Central Florida’s major attractions, with Disney just a short drive away. Purchased as an income-producing short-term rental or a personal vacation home, 920 Paradise offers something most resort properties can’t: the chance to shape every room to your own vision and set your home apart in a community where standing out matters.

920 Paradise Dr, Davenport

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
1880 Summer Drive, Davenport
$540,000
5 Beds ⋅ 6 Baths ⋅ O6439025 MLS
Welcome to luxury vacation living at Windsor Island Resort! Located on desirable Summer Drive in Davenport’s premier gated resort community, this fully furnished, turn-key home is designed for both unforgettable getaways and short-term rental potential. Enjoy luxury hotel-style amenities including a zero-entry heated pool, lazy river, waterslides, splash park, fitness center, pickleball, sand volleyball, mini golf, and poolside tiki bar. Just minutes from Orlando’s world-famous theme parks, shopping, dining, and golf, this is the perfect opportunity for a vacation home that delivers resort living from day one. Showings require advance notice as the home may be occupied by short-term rental guests.

1880 Summer Drive, Davenport

Listing courtesy of KELLER WILLIAMS ADVANTAGE III. murraycoleman@kw.com
936 Paradise Drive, Davenport
$449,000
5 Beds ⋅ 5 Baths ⋅ O6440616 MLS ⋅ Na BLDG.
Welcome to this beautifully furnished 5-bedroom, 4.5-bath townhome in the highly desirable Windsor Island Resort. This two-story home features stylish furnishings, comfortable living areas, and a private screened-in splash pool with covered patio, perfect for relaxing or entertaining. One of the home’s prime advantages is its location directly across from the clubhouse and resort amenities, offering guests quick and convenient access to all the fun. Windsor Island Resort features a gated entrance, clubhouse, fitness center, resort-style pool with lazy river, splash pad, playground, mini golf, on-site restaurant and bar. Conveniently located near Central Florida’s world-class attractions, shopping, and dining, this turnkey property is ideal as a vacation home, primary residence, or income-producing rental. All information available to the Seller and Listing Agent has been provided in the listing and disclosures. If information is not included, it is not available to us. Buyers and their agents are responsible for verifying all information that is important to their purchase, including but not limited to HOA rules and regulations, leasing restrictions, fees, room dimensions, square footage, lot size, taxes, and any other property details. All measurements and listing information are approximate and should be independently verified by the Buyer and Buyer's Agent.

936 Paradise Drive, Davenport

Listing courtesy of ORANGE REALTY PROFESSIONALS LLC. 321-525-3505
2127 Lelani Circle, Davenport
$839,900
10 Beds ⋅ 8 Baths ⋅ O6436965 MLS
For buyers seeking a short-term rental investment designed around the guest experience, 2127 Lelani Circle is a fully furnished, turnkey property in the amenity-rich Windsor Island Resort, offering 4,399 sq. ft. with 10 bedrooms and 8 bathrooms. Custom painting, cinematic character theming and atmospheric LED lighting effects throughout give the interior its own identity, while a south-facing heated pool and spa extend the vacation experience outdoors. The open blue-and-white living space introduces the home's blend of luxury and distinctive design, with a leather sectional and coordinated seating arranged around a custom textured media wall feature with LED backlighting. The kitchen pairs modern cabinetry, stainless steel appliances and granite countertops with an oversized island seating 4 and nearby dining for 8. Two bedrooms are located on the main level for added convenience and flexibility. The signature Mickey suite is hand-painted throughout in a Mickey-inspired palette, complemented by vintage-style Mickey and Minnie artwork and a private en suite that also serves as the pool bath. Several upstairs bedrooms create their own immersive settings through hand-painted walls and ceilings, oversized murals, framed artwork and integrated LED lighting effects. Spider-Man, Minions, Frozen and Avengers designs surround guests with color and character, joined by a galaxy room in painted starfields and a wizarding room with portraits set into the ceiling. The oversized Mario-themed game loft continues the experience with bold color-blocked walls, illuminated gaming art, sectional seating, a wall-mounted television, ping-pong and foosball tables, while the 2-car garage remains available for parking and storage. Beyond the sliding doors, an extended paver deck surrounds the south-facing heated pool and spa, while the covered lanai provides shade for outdoor seating and alfresco dining. Then there is Windsor Island itself—ALOHA! The Hawaiian-inspired Aloha Clubhouse anchors a water-park-style complex featuring a zero-entry resort pool, lazy river, dual waterslides, splash zone, hot tub, private cabanas and the Blue Marlin Grille. A fitness center, arcade, miniature golf, playground, sports court, firepit and organized activities complete the amenity offering. All of this is just a few miles from Walt Disney World, with convenient access to shopping, dining and Central Florida's major roadways. All information provided, including room sizes, is deemed reliable but not guaranteed and should be independently verified by the buyer or buyer's agent.

2127 Lelani Circle, Davenport

Listing courtesy of FATHOM REALTY FL LLC. bnunez@fathomrealty.com
1230 Aloha Boulevard, Davenport
$565,000
6 Beds ⋅ 5 Baths ⋅ O6437685 MLS
Welcome to this spectacular 6-bedroom vacation home in the highly sought-after Windsor Island Resort, offering privacy with no rear neighbors, beautiful open views, and exceptional resort-style living. Fully furnished and ready to enjoy, this home features a heated private pool, spacious loft, and an open-concept floor plan designed for both entertaining and relaxing. The kitchen is the heart of the home, featuring an oversized island, granite countertops, stainless steel appliances, and plenty of space for gathering with family and friends. The open living and dining areas offer beautiful views of the pool and the open space behind the property, creating a bright and inviting atmosphere.Adding to the home's unique appeal, two bedrooms feature beautifully hand-painted Disney theme park murals, creating magical themed retreats that are sure to delight guests of all ages. With generous living spaces, multiple bedrooms, a loft, and a private pool, this home is perfectly suited for memorable family vacations and entertaining.Windsor Island Resort has earned its reputation as one of the premier vacation destinations in the Disney tourist area, and it's easy to see why. The resort features an impressive 8,000-square-foot clubhouse with a lounge, concierge services, sundry shop, fitness center, arcade/game room, Blue Marlin Grille Bar & Restaurant, playground, mini-golf course, and a firepit area with views of Disney fireworks.Outdoor amenities are equally impressive, including a heated beach-style zero-entry resort pool, lazy river, water slide, splash pad, poolside cabanas, and abundant sun loungers.Whether you're looking for a vacation retreat or a beautifully furnished property in one of Central Florida's most desirable resort communities, this home delivers the space, amenities, privacy, and unforgettable resort experience that owners and guests are looking for.

1230 Aloha Boulevard, Davenport

Listing courtesy of CENTURY 21 CARIOTI. 407-354-0074
237 Jetty Way, Davenport
$399,000
5 Beds ⋅ 5 Baths ⋅ S5153203 MLS
Welcome to resort-style living at Windsor Island Resort! This beautifully furnished 5-bedroom, 4.5-bath townhome, built in 2021, offers 2,293 sq ft of thoughtfully designed space behind a guard-gated entrance. The first floor features a bedroom and full bath for guests, while upstairs you'll find a primary suite with a walk-in closet, a second primary suite, two additional themed bedrooms that are well-decorated to attract short-term rental guests, and a versatile loft. All appliances are stainless steel. Step out to your own private screened pool, or enjoy the community's resort-style amenities. This is a pet-free house, although pets are allowed in the community. Windsor Island Resort is known for outstanding amenities, including an 8,000 sq. ft. clubhouse, resort-style pool and spa, lazy river, poolside cabanas, fitness center, on-site restaurant and bar, playgrounds, sports courts, arcade, and lounge areas for guests of all ages. The community's prime location provides convenient access to US 192, I-4, shopping, dining, golf, supermarkets, and Central Florida's major attractions. Whether purchased as a personal vacation retreat or income-producing short-term rental investment, this beautifully upgraded home offers a compelling opportunity in one of the Disney area's most desirable resort communities, just a short drive away. With a fully furnished turnkey setup, immersive themed spaces, standout entertainment areas, and a guest-focused design throughout, 237 Jetty Way is ready for its next owner to enjoy from day one.

237 Jetty Way, Davenport

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
716 Gardenia Lane, Davenport
$489,000
5 Beds ⋅ 5 Baths ⋅ O6430639 MLS ⋅ 710 BLDG.
Turn-Key Short-Term Rental | Strong Occupancy Appeal South Facing Pool | Guard-Gated Resort Income-producing short-term rental — professionally designed & fully furnished, especially the theme rooms to attract tourists Turn-key operation — no setup required, ready to generate revenue immediately with many existing bookings can be transferred. Professional designer furniture set up with frozen and star war theme rooms. Pool heater was replaced in 2025.Highly desirable south-facing screened pool — maximizes sunlight & rental demand 5 bedrooms / 4.5 baths — ideal for large groups up to 14 persons, higher ADR & longer stays First-floor guest suite — appeals to multigenerational & accessibility-focused guests Upstairs loft adds entertainment space & booking flexibility Prime location near clubhouse & guarded gate — superior guest convenience vs interior units Close to the club house by walking 3 minutes. Located in a live guard-gated resort community with premium amenities: -Resort-style pools & lazy river with poolside bar -On-site restaurant -State-of-the-art fitness center -Mini golf, tennis, basketball & sand volleyball Strong appeal for Airbnb / Vrbo investors seeking consistent occupancy Ideal for investors targeting cash flow + long-term appreciation

716 Gardenia Lane, Davenport

Listing courtesy of GOLDEN SUN REALTY INC. 4077652618
1876 Summer Drive, Davenport
$625,000
7 Beds ⋅ 6 Baths ⋅ S5153316 MLS
1876 Summer Drive at Windsor Island Resort is the turnkey, fully furnished vacation home investors and second-home buyers have been waiting for. Designed for both fun and function, this spacious property offers an open-concept layout, private screened pool, multiple ensuite-style bedroom options, themed rooms, and an entertainment-packed upstairs loft with theater seating, games, and air hockey. It has everything today’s guests are looking for in a memorable Central Florida stay. From the moment you step inside, you’re welcomed by a bright and spacious open-concept floor plan where the kitchen, dining area, and living room come together seamlessly, each with beautiful views of the private screened pool. The first-floor primary suite offers comfort and convenience, featuring an ensuite bathroom and direct pool access. The main level also includes a half bath and laundry room for added functionality. Upstairs, the fun continues with a spacious family room and game loft designed for entertainment. Whether enjoying movie night in theater-style seating, playing video games, challenging friends to chess or checkers, or enjoying a game of air hockey, this home is built for memory-making. The upstairs bedrooms are thoughtfully arranged in three separate sections, offering privacy and flexibility for owners and guests. At the front of the home, two bedrooms each feature their own private bathrooms. In the middle there is two additional bedrooms are positioned near the charming themed rooms, Princess and Captain America, adding a fun and memorable touch for younger guests. Toward the rear, two more bedrooms share a full bathroom, creating a layout that comfortably accommodates larger groups. With close proximity to Disney, Universal, SeaWorld, Orlando International Airport, and the resort-style amenities of Windsor Island, this beautifully furnished property is ready to deliver as a primary residence, second home, or short-term rental investment.

1876 Summer Drive, Davenport

Listing courtesy of RE/MAX HERITAGE. 863-424-2309
996 Paradise Drive, Davenport
$569,000
5 Beds ⋅ 5 Baths ⋅ O6420344 MLS ⋅ 996 BLDG.
Fully furnished Themed short term rental. LED lighting inside and out. Game room in the house! Open layout with modern kitchen and private pool. Windsor Island Resort has amazing amenities: mini-golf, a resort style pool, waterslides, lazy river, and bar and restaurant. This home will impress any guests!

996 Paradise Drive, Davenport

Listing courtesy of EXP REALTY LLC. 888-883-8509
108 Jetty Way, Davenport
$560,000
5 Beds ⋅ 5 Baths ⋅ O6419919 MLS ⋅ Jetty BLDG.
Stylish former model home with private pool in the highly desirable Windsor Island Resort community! Located directly across from the clubhouse and resort amenities, this fully furnished end-unit home offers an excellent location, abundant natural light, and a bright, open floor plan. The kitchen features a breakfast bar, granite countertops, stainless steel appliances, and ample white cabinetry. Enjoy your own private screened pool, perfect for relaxing or entertaining. Windsor Island Resort offers outstanding amenities, including a clubhouse, fitness center, resort-style pool, waterslide, lazy river, volleyball and tennis courts, play zone, mini golf, and full-service bar. Conveniently located just minutes from Disney World, area attractions, restaurants, and shopping. Great opportunity for vacation use, short-term rental, or investment. Booking history and calendar available in MLS attachments.

108 Jetty Way, Davenport

Listing courtesy of ZEAL REALTY. 407-789-2051
1837 Summer Drive, Davenport
$689,000
7 Beds ⋅ 6 Baths ⋅ O6412823 MLS
Exceptional corner-lot vacation home located just steps from the clubhouse in the highly sought-after Windsor Island Resort. This beautifully maintained and fully furnished property offers a spacious open-concept layout, modern finishes, and ample space for guests. Enjoy the convenience of being just steps from to the resort's amenities, including a lazy river, water slides, clubhouse, fitness center, arcade, sports courts, and more. The private screened pool area provides the perfect setting for relaxation and entertainment. The property is owner-managed and is currently utilized as a short-term vacation rental. Existing future reservations may be available for transfer, subject to booking platform policies and applicable requirements. Ideally located near Walt Disney World, shopping, dining, and major highways, this fully furnished property offers an excellent opportunity to own a vacation home in one of Central Florida's most popular resort communities.

1837 Summer Drive, Davenport

Listing courtesy of MS LAND & BUILDING LLC. 407-466-7000
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