Windsor Island Residence Homes with Shingle Roof

Windsor Island Residence Homes with Shingle Roof

Welcome to Windsor Island Residence, a stunning community nestled in the heart of Davenport, Florida, within the picturesque Polk County. This charming subdivision offers a perfect blend of modern living and serene surroundings, making it an ideal choice for families, retirees, and everyone in between.

Windsor Island Residence boasts a variety of beautifully designed homes, each featuring elegant shingle roofs that not only enhance the aesthetic appeal but also provide durability and protection against the Florida elements. These homes are thoughtfully crafted with open floor plans, spacious living areas, and contemporary finishes, ensuring that comfort and style go hand in hand.

Living in Windsor Island Residence means enjoying the best of both worlds—tranquility and convenience. Residents can take advantage of the community’s lush green spaces, walking trails, and recreational facilities, perfect for family outings or leisurely strolls. Additionally, the subdivision is conveniently located near major highways, making it easy to access nearby attractions such as Walt Disney World, Universal Studios, and the stunning beaches of the Gulf Coast.

The community's commitment to a vibrant lifestyle is evident in its planned events and social gatherings, fostering a strong sense of camaraderie among neighbors. Whether you’re seeking a vacation home or a permanent residence, Windsor Island Residence offers an inviting atmosphere and a place where memories can be made.

Discover the charm and warmth of Windsor Island Residence, where your dream home awaits in the heart of Florida!

Newest Windsor Island Residence Homes with Shingle Roof

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

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

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

8 Beds ⋅ 6 Baths ⋅ O6431292 MLS

Spacious 8-Bedroom Pool Home in the Sought-After Windsor Island Resort – Davenport, FL Welcome to your dream vacation home! This stunning 8-bedroom, 6-bathroom single-family residence is located in the highly desirable Windsor Island Resort—one of Davenport’s premier gated vacation communities just minutes from Disney. Step inside and be amazed by the modern décor, open-concept layout, and spacious living areas perfect for entertaining and relaxing. The fully equipped gourmet kitchen features sleek finishes, stainless steel appliances, and a large island overlooking the bright and airy dining and living spaces. This home offers the ultimate in flexibility and comfort with multiple themed bedrooms, dual primary suites, and plenty of room for large families or groups. Step outside to your private covered lanai and screened-in pool, where you can unwind or enjoy Florida’s sunshine all year round. Located just a short walk to the resort-style clubhouse, residents and guests enjoy access to Windsor Island’s incredible amenities, including a lazy river, water slides, splash pad, fitness center, mini golf, sports courts, and more. Whether you’re looking for a lucrative short-term rental investment or a family-friendly getaway, this home has it all. Don’t miss this opportunity to own a piece of paradise in Central Florida’s top resort community.

2123 Lelani Circle, Davenport

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

10 Beds ⋅ 9 Baths ⋅ O6428920 MLS

Where Central Florida vacations become the stories families retell for years. Tucked behind the gates of Windsor Island Resort, this 10-bedroom, 8.5-bath retreat (4,399 SqFt, built 2021) was made for the arrival — that moment when ten doors open onto ten different worlds and the whole group scatters, laughing, before anyone has unpacked a single bag. Professionally themed bedrooms turn bedtime into the best part of the day. The private game room keeps the energy alive long after the parks have closed. And when the evening finally slows down, the screened pool and spa glow quietly under the Florida sky — private, warm, unhurried, entirely yours. Inside, light moves freely across an open-concept main level where kitchen, living and dining spaces flow as one and slide open to the pool deck. Fully furnished and professionally decorated throughout, with a 2-car garage and every detail already in place. Beyond your door, Windsor Island Resort delivers the rest: a signature clubhouse, resort pool, fitness center, playground and on-site dining. Minutes from US-27 in Davenport and a short drive from Central Florida's world-famous attractions. Offered fully furnished and As-Is, income-ready with no minimum stay. Windsor Island is a short-term-rental resort community, and the home is designated for vacation-rental and owner vacation use rather than permanent residency. Buyer and buyer's agent to verify all measurements, figures, HOA rules and use restrictions. Schedule your private showing today.

2280 Lelani Circle, Davenport

5 Beds ⋅ 4 Baths ⋅ O6422876 MLS

An Absolute MUST SEE!! This SPACIOUS 5 Bedroom 4 FULL Bath Private Pool Home is being offered FULLY FURNISHED! SUCCESSFUL VACATION RENTAL PROPERTY with over $60,000+ in Rental Income this year & additional future bookings for 2027 that can convey to next owner if desired, great for a 1031 exchange to immediately start cash flow income! Located in the beautiful upscale gated community of Windsor Island Resort, this home is perfect for entertaining friends & family. As you proceed through the foyer, you will immediately notice the open concept that creates an even flow into the kitchen & dining area. The kitchen is equipped with a large island with a breakfast bar, stainless appliances, stone countertops, and hardwood cabinets with crown moulding. There is a dining area conveniently located adjacent to the kitchen with seating for 6 ppl. From the living area enjoy an amazing view of your pool deck with a beautiful decorative accent wall which includes a large sectional sofa providing ample space for everyone. As an added bonus there is a guest room located on the first floor as well. You will notice as you walk out onto the pool area it has a covered lanai and large pool that will provide hours of enjoyment and lasting memories. When you arrive upstairs, you find a loft space perfect for a small office or gaming area. The large primary suite also has enough space to add furniture for an additional seating area is desired. The primary bath has dual vanity sinks, stone countertops, hardwood cabinets and a large walk-in shower. The reaming 4 guest suites are also located on the 2nd floor, and 3 of the guests rooms are professionally themed, elevating the fun and excitement for everyone. Windsor Island has a state of the art Amenity Complex and Clubhouse that includes Zero Entry Pool with Cabanas, Waterslides, Lazy River, Fitness Center, Splash Zone, Volleyball & Tennis Courts, and a Pool Bar that offers great Food & Beverage offerings throughout the day. This gated resort community features a fantastic clubhouse, that comes with a fitness center, pool, waterslide, lazy river, volley ball court, tennis courts, a play zone with lots of activities, and much more! HOA includes lawn maintenance, internet, cable, daily valet trash service in 24- hour gated community. Minutes aways from shopping, dining, and world Disney attractions! Schedule your showing appointment now to make this home a turn key dream!

1607 Kona Lane, Davenport

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

5 Beds ⋅ 5 Baths ⋅ S5152558 MLS ⋅ 267 BLDG.

Price Adjustment - 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, 267 Jetty Way is ready for its next owner to enjoy from day one.

267 Jetty Way, Davenport

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

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

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

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