Windsor Island Single Family Homes For Sale in Davenport - 40 homes

Remarks: Spectacular 10-Bedroom Resort Pool Home – Windsor Island, Davenport, FL. Your ultimate Florida escape awaits! This extraordinary 10-bedroom, 8-bath retreat sits in the heart of the world-class Windsor Island Resort—just minutes from Disney. Designed to impress, the home blends sleek, modern décor with a wide-open floor plan that’s perfect for entertaining, relaxing, or hosting unforgettable family gatherings. Chef’s kitchen with stainless steel appliances, oversized island, and seamless flow into the dining and living spaces. Three primary suites + themed bedrooms designed for fun and comfort—ideal for large families, groups, or high-earning vacation rental guests. Private screened pool + covered lanai for year-round outdoor living. Step outside your door and walk to the resort’s unmatched amenities: lazy river, dual water slides, splash pad, fitness center, mini golf, sports courts, and a lively clubhouse. Whether you’re seeking a high-income short-term rental investment or a personal paradise for your family, this home delivers the best of Central Florida living. Opportunities like this don’t last—schedule your showing today!

Listing is courtesy of: RE/MAX REALTEC GROUP (407-818-1100)

Listing Agent: Kenneth Holden, Pa (407-808-8175)

Remarks: 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.

Listing is courtesy of: FLORIDA SCANDI REALTY LLC (407-982-7224)

Listing Agent: Flavia Cabral (407-470-4992)

Remarks: Turnkey opportunity in the highly sought-after Windsor Island Resort! This spacious and well-maintained home is located in a short-term rental / Airbnb-approved community, making it ideal for both personal enjoyment and income-producing investment. Featuring generous living spaces, modern finishes, and access to resort-style amenities, this property offers the perfect blend of comfort and profitability. Owners and guests enjoy a gated entrance, clubhouse, pool, fitness center, and more—all within minutes of Central Florida attractions. Whether you’re looking for a primary residence, vacation home, or a proven rental performer, this property delivers exceptional value in a high-demand resort community.

Listing is courtesy of: PAK HOME REALTY (909-351-5105)

Listing Agent: Elizabeth Amesty (786-781-7576)

Remarks: Welcome to Windsor Island Resort, a gated community just minutes from the major theme park attractions. This stunning five-bedroom, four-and-a-half-bathroom single family home boasts modern elegance with granite countertops, stainless steel appliances, effortlessly blending comfort with style. Ideal for families or as an income-producing short-term rental, this home features one bedroom downstairs and four upstairs, ensuring privacy and convenience for all. The soundproof design guarantees peace, while the private pool and patio offers a tranquil outdoor retreat. Don't let this opportunity slip away – schedule your showing today and secure your slice of Florida paradise! Great investment opportunity.

Listing is courtesy of: AMERICAN HORIZONS REALTY (407-466-0256)

Listing Agent: Martonio Pinto (407-466-0256)

Remarks: Welcome to a 10-Bedroom vacation short-term rental pool home is located just 15 minutes from Disney and is the perfect destination for a magical getaway.11 theme bedrooms and garage with perfect decor. The home features a private pool and jacuzzi, movie theater room, game room, bedrooms with themes and lighting. Enjoy all the thrills of a theme park vacation in the comfort and convenience of your own private paradise. Take a dip in the sparkling pool, relax in the cabanas, or enjoy a game of volleyball or basketball take a ride down the lazy river. The clubhouse has a hot tub, fitness room, and a mini golf course. With such a variety of amenities, this property is the perfect place to live and play!

Listing is courtesy of: U S GLORY REALTY (407-222-7801)

Listing Agent: He Gao (407-955-0138)

Remarks: Exceptional property alert. Come see this amazing Windsor Island 6-bedroom vacation home. This property is brand new and features custom decor and furnishings. If you want a pristine vacation home for personal and or rental purposes, this is it! Turnkey for rental, with very high-quality Sturdy furniture that will hold up for many years. Also featuring an amazing clubhouse adventure with full gym, arcade, lazy river, slides, pool bar and more! This is the number one newest Disney vacation community in Orlando:) Don’t miss it!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Chris Gabriel, Pa (386-451-1361)

Remarks: This professionally designed, fully furnished 7-bedroom, 5.5-bath vacation retreat offering over 3,200 square feet of upgraded living space in one of Central Florida’s most sought-after resort communities. This turnkey property blends upscale finishes with functional design, ideal for investors and vacationers alike. Step inside to discover a spacious open-concept layout perfect for large groups. The gourmet kitchen features rich espresso cabinetry, granite countertops, stainless steel appliances, and a generous center island with seating that's ideal for casual dining and entertaining. The main-level primary suite offers direct pool access and a spa-inspired en suite bath with dual sinks, a garden tub, and walk-in shower. Upstairs, a sprawling loft has been transformed into a private game and movie room, surrounded by six additional bedrooms and four full baths, providing ample space for guests and family. Outside, enjoy your own private oasis with a heated pool and spa, covered lanai, and plenty of seating for sun-soaked relaxation or evening gatherings. Located in Windsor Island Resort, just minutes from Disney, this community is packed with world-class amenities: a zero-entry resort pool, lazy river, water slide, splash pad, clubhouse with concierge and arcade, fitness center, mini golf, playground, firepit with Disney fireworks views, and the Blue Marlin Grille restaurant. With short-term rentals allowed and high demand year-round, this property offers both lifestyle and income potential.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ping Ma (863-332-0298)

Remarks: An Exciting 7 Bedroom Vacation Home in Windsor Island is looking for a new owner. Close to the Disney Parks! Beautifully furnished with high end furniture. 5 King Bedrooms all with super comfortable beds. All bedrooms have tv's and the two kids bedrooms are fun themed with bunk beds. Garage has been converted into an out of this world game room with Double Gaming Station, Real Slate Pool table and a $10,000 Racing Simulator. Loft has an additional movie theater with a 165 inch screen and projector ready for a family movie night. Every bedroom in the house has its own TV. 5 adult bedrooms all have king beds and 3 are en-suite. Two kids rooms have bunks beds and fun theming with Wreck It Ralph and Moana. Kitchen is fully equipped with everything you would need for a comfortable stay. This 3300 sq ft vacation home is one of the newest vacation homes in Orlando and located in the wonderful resort of Windsor Island. The resort features super modern and spacious Club house. The resort amenities include a large Community Pool with a Slide, Hot Tub, Fitness Center, Arcade Room, Pickle Ball Courts, Volley Ball Court, Mini Golf court, Bar and Restaurant, Security gates and more. Call and schedule your private tour today!

Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)

Listing Agent: Stani Delcheva (407-405-6815)

Remarks: 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 kids’ 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 100% rental-ready.

Listing is courtesy of: JULIA MARTIN REALTY (831-578-7819)

Listing Agent: Yezi Sha (408-569-8194)

Remarks: Welcome to 4361 Lana Ave — where luxury meets experience, and every detail is designed to impress. Located in the highly sought-after Windsor Island Resort, this nearly brand-new, fully furnished 10-bedroom, 8-bathroom vacation home is the epitome of themed luxury living. More than just a home, this is a true turnkey investment opportunity — a high-performing short-term rental that can comfortably accommodate 20+ guests, making it ideal for large group vacations and maximizing rental income. Step inside and you’re immediately immersed in a world of enchantment. Thoughtfully designed themed spaces and high-end finishes create a unique, memorable experience that keeps guests coming back. The gourmet kitchen, expansive dining area, and spacious living room flow seamlessly together, offering the perfect setting for entertaining and creating unforgettable moments. The outdoor space is just as impressive. A massive covered lanai overlooks a private heated pool and spa with a brick-paved deck — your own resort-style oasis perfect for relaxing after a day at the parks or hosting guests under the Florida sun. Upstairs, the home continues to wow with a large bonus room transformed into a Star Wars–themed theater, complete with a pool table for added entertainment. This one-of-a-kind feature sets the property apart and elevates the guest experience. As part of Windsor Island Resort, residents and guests enjoy access to world-class amenities, including an 8,000 sq. ft. clubhouse, resort-style pool and spa with lazy river, poolside cabanas, fitness center, restaurant and bar, playground, volleyball, tennis and basketball courts, arcade room, and lounge areas. Conveniently located near US-192 and I-4, this home is just minutes from Walt Disney World and all of Central Florida’s major attractions — a prime location for consistent bookings and strong returns. Whether you’re looking for a luxury vacation retreat or a cash-flowing investment, this property delivers on every level. Opportunities like this don’t come often — secure your place in one of Orlando’s most exciting vacation communities today.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Anna Shi (407-216-1215)

Remarks: Stunning 10-Bedroom Investment Opportunity | Windsor Island Resort 4117 Lana Ave, Davenport, FL Discover this exceptional Clearwater Grand model, a high-capacity 10-bedroom estate located in the highly sought-after Windsor Island Resort. Professionally decorated and fully optimized for short-term rental performance, this home offers a seamless blend of luxury and high-energy entertainment. Property Highlights: Expert Interior Design: Sold fully furnished with a professional touch. The open floor plan flows effortlessly into a large loft, providing multiple expansive zones for guests to gather. Immersive Entertainment: Features a private movie theater and a dedicated game room equipped with commercial-grade arcades, offering a premier experience right at home. Custom Accommodations: Ten spacious bedrooms, including expertly executed themed rooms designed to drive booking demand. Outdoor Living: A private, screened-in deck featuring a heated pool and spa, ideal for year-round relaxation. The Windsor Island Lifestyle: Situated in a premier gated community, this property is just steps away from some of the best resort amenities in the area. Guests enjoy an amazing water park, lazy river, dual water slides, and a massive clubhouse—making it one of the most fun and popular destinations for vacationers. This is a great opportunity to acquire a turnkey, high-performing asset in a prime location.

Listing is courtesy of: DEBRASSI REALTY LLC (407-446-1343)

Listing Agent: Marcela Andrade Drummond (407-752-2323)

Remarks: Under contract-accepting backup offers. Investor opportunity—turnkey, short-term rental/Airbnb-ready property. Seller is open to cash offers and a quick closing. Ideal for investors or 1031 exchange buyers seeking a clear, income-producing replacement property. Sold as-is and easy to show. Discover modern luxury in this stunning 5-bedroom, 4-bathroom vacation home, nestled within the highly sought-after, 24-hour guard-gated Windsor Island Resort. SHORT-TERM RENTALS ALLOWED (AIRBNB ALLOWED)! Located just a quick walk from the resort’s clubhouse, this home offers convenience and unparalleled access to world-class amenities. During your stay, you and your guests will enjoy complimentary access to the resort’s extravagant clubhouse, featuring a lazy river, dual water slides, a splash pad, and a resort-style pool. The clubhouse also offers a variety of activities and amenities, including a fitness center, game room, café, ice cream shop, fire pit for evening gatherings, and even a tropical walking trail. For sports enthusiasts, there are basketball and sand volleyball courts, as well as putt-putt golf. Windsor Island Resort's prime location is close to Orlando’s renowned attractions, shopping, dining, and entertainment options, making it the perfect place to call your vacation home or investment property. Whether you're seeking a luxurious getaway or a short-term rental opportunity, this vibrant community has everything you need to create lasting memories.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Mike Chen, P.A (503-888-8070)

Remarks: 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.

Listing is courtesy of: 3D TEAM REALTY LLC (863-604-3662)

Listing Agent: Grace Ponzo (863-242-4335)

Remarks: PRICE REDUCED – SELLER MOTIVATED!!! Best-priced 10-bedroom home in Windsor Island Resort — fully furnished and turnkey! Discover the charm of this exquisite home perfect for large families or hosting guests. The newly updated kitchen features modern amenities, while the cozy living room provides a welcoming space for relaxation. Enjoy the expansive layout, abundant natural light, and a refreshing pool. This property provides a unique opportunity to create your ideal home. Don’t miss out on making this beautiful house your own! Windsor Island is a perfect Resort for your family and guest. Call me today!

Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)

Listing Agent: Vivian Branco (305-469-0729)

Remarks: Exceptional Value in Windsor Island Resort! Luxuriously Upgraded & Themed Vacation Home. Discover the perfect blend of luxury, fun, and investment potential with this stunning 10-bedroom, 8-bathroom vacation home in the sought-after Windsor Island Resort. With space to comfortably host over 20 guests, this fully furnished and professionally designed home is ideal for memorable family vacations or maximizing short-term rental income. No detail was spared—over $170,000 in thoughtful upgrades bring sophistication and excitement to every corner. Step inside to an open-concept layout featuring elegant finishes, a spacious gourmet kitchen, a generous dining area, and a stylish living room designed for effortless entertaining. Themed bedrooms throughout the home offer a touch of magic for guests of all ages. Upstairs, the large bonus loft has been transformed into a custom Avengers-inspired theater and game space, complete with a pool table—perfect for movie nights or relaxing after a day at the parks. Outside, unwind under the covered lanai beside the heated pool and spa, all set on a beautifully paved deck. For even more entertainment, the garage has been converted into a fully stocked game room. As part of the gated Windsor Island Resort, residents and guests enjoy access to world-class amenities, including an 8,000 sq. ft. clubhouse, resort-style pool with lazy river, fitness center, poolside bar and grill, sports courts, arcade, playground, and more. Just minutes from Disney, major highways, shopping, and dining, this home offers an unbeatable location and endless possibilities—whether you're building memories or your rental portfolio.

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Veronica Li (407-674-0460)

Remarks: Welcome to this FULLY FURNISHED, luxury 9 BED / 8 BATH "cash cow" in the popular Windsor Island Resort just minutes away from Walt Disney World! This unique, professionally decorated home makes the perfect vacation rental and features all the comforts of home and more! The open floor plan includes a spacious kitchen equipped with stainless appliances and dining room area perfect for family gatherings, which merges seamlessly with the covered lanai that overlooks the heated pool and spa with deck. No detail has been overlooked with the diverse-themed décor of the upstairs bonus/game room and bedrooms. Windsor Island Resort is a gated community featuring world class amenities including an 8,000 sf clubhouse, tennis, volleyball and basketball courts, mini golf, arcade room, fitness center and on-site dining to enjoy. Relax on the loungers by the pool for hours with a book, soaking up the Florida sunshine while the young ones play in the lazy river and splash playground. The location is also great for viewing nightly Disney fireworks with access to US 192, I-4, as well as all other themed Orlando attractions.

Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)

Listing Agent: Eileen Li (407-765-2589)

Remarks: Discover the ultimate opportunity in Windsor Island Resort! Don't let this exceptional chance slip away. Presenting a fully furnished, enchanting pool and spa home in this coveted resort community. Step inside to be welcomed by a grand 2-story foyer graced by an elegant staircase leading to the second floor. This property offers 8 bedrooms and 6 bathrooms, meticulously adorned with a keen eye for perfection. The well-appointed kitchen seamlessly connects to the spacious gathering room and dining area, and its sliding doors open to a generously sized covered lanai. Beyond lies a fully screened pool and spa, creating the ideal setting for indoor/outdoor entertainment. The primary suite and an additional guest suite are thoughtfully located on the first floor, ensuring effortless accessibility. Upstairs, you'll find 2 private suites, 2 sets of Jack-n-Jill suites, totaling 6 bedrooms and 4 bathrooms, an expansive 26' x 15' loft, and a generously proportioned theater room, making this home a perfect haven for the entire family. This secure, gated resort community boasts a brand-new clubhouse, offering a fitness center, a pool with a thrilling waterslide, a lazy river, volleyball and tennis courts, a play zone brimming with activities, and more. The HOA includes lawn maintenance, internet, cable, and daily valet trash service in this 24-hour gated sanctuary. Situated just minutes away from shopping, dining, and world-renowned attractions, this property is perfectly positioned. Don't delay; schedule your showing appointment now and turn this home into your dream-come-true!

Listing is courtesy of: SIMPSON REALTY LLC (407-371-5955)

Listing Agent: Cristian Cen Chen (407-450-9010)

Remarks: Fully Upgraded & Themed Vacation Home in Windsor Island! Step into a world of luxury and imagination with this spectacular 10-bedroom, 8-bathroom vacation home. Designed to accommodate over 20 guests, this fully furnished retreat is perfect for unforgettable family getaways or a lucrative short-term rental investment. The owner invested $170,000 in upgrades to create a home that seamlessly blends elegance, comfort, and entertainment. From the moment you enter, you’ll be captivated by the thoughtfully curated themed décor, high-end finishes, and expansive open-concept design. The gourmet kitchen, oversized dining area, and inviting living room provide the ideal setting for hosting and entertaining. Upstairs, a colossal bonus room has been transformed into an immersive Star Wars-themed theater, complete with a pool table, offering endless fun for guests of all ages. The excitement continues outside, where a massive covered lanai overlooks the heated pool and spa, set against a beautifully paved deck—the perfect spot to relax after a day at the parks or entertain under the Florida sun. For even more entertainment, the garage has been converted into a fully equipped game room, ensuring fun at every turn. Located in the highly sought-after gated community of Windsor Island Resort, this home grants access to world-class amenities, including an 8,000 sq. ft. clubhouse, a heated pool and spa with a lazy river, poolside cabanas, a fitness center, a restaurant & bar, a playground, volleyball, tennis & basketball courts, an arcade room, and a relaxing lounge area with TVs. Conveniently situated near US 192 and I-4, this prime location places you just minutes from Disney, shopping, dining, and all of Central Florida’s top attractions.

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Veronica Li (407-674-0460)

Remarks: Under contract-accepting backup offers. Spacious 10-Bedroom Vacation Home in Windsor Island Resort – Fully Furnished & Turnkey! Nestled within the established and highly sought-after Windsor Island Resort, this stunning vacation home offers a perfect blend of comfort, style, and convenience for Disney-area getaways. Fully furnished and featuring 10 bedrooms and 8 bathrooms, this property provides ample space for family gatherings, group vacations, or rental income opportunities. Inside, the home welcomes you with a bright open-concept layout that feels inviting and relaxing. The screened-in heated pool and spa, paired with a spacious lanai, create the ultimate outdoor retreat for lounging, entertaining, or enjoying Florida’s sunshine year-round. The kitchen is a chef’s dream, equipped with stone countertops, stainless steel appliances, and a breakfast bar, making it ideal for preparing meals for large groups or casual dining alike. Bedrooms are thoughtfully designed with a mix of magical Disney-themed rooms and modern, contemporary spaces, ensuring every guest finds a space that suits their style. Beyond the home, Windsor Island Resort offers resort-style amenities including an 8,000 sq. ft. clubhouse, heated pool and spa with lazy river, poolside cabanas, fitness center, on-site restaurant and bar, playgrounds, and sports courts for tennis, volleyball, and basketball. Indoor entertainment includes an arcade and lounge area with TVs, catering to guests of all ages. Located with easy access to US 192 and I-4, this home is just minutes from Disney and other world-class attractions, offering convenience for both vacationers and short-term rental guests. With its combination of spacious, stylish accommodations, resort amenities, and prime location, this home at 3629 Lily Lane represents a turnkey opportunity for those seeking a remarkable Disney-area vacation property.

Listing is courtesy of: PRISTINE INTERNATIONAL REALTY LLC (407-286-3846)

Listing Agent: Ursula Garcia Moraes (407-429-1417)

Remarks: Stunning 7-bedroom, 5.5-bath Windsor Island Resort home — turnkey luxury and investment potential. This meticulously maintained property is ready to start generating rental income immediately, with furnishings and decor curated for high occupancy. Its prime location is steps from the clubhouse, offering quick access to resort amenities while ensuring privacy for downtime. Themed Minion and Mickey Mouse rooms create immersive, family-friendly experiences that guests love. A gaming loft provides space for gatherings and movie nights, ideal for families and groups. No rear neighbors mean enhanced privacy and tranquil evenings on the extended lanai complete with summer kitchen. Gorgeous blue cabinetry throughout and a custom coffee bar add bright, contemporary touches and daily luxury. The 7 bedrooms and 5.5 bath Seashore Model offers ample sleeping capacity and privacy for all guests. Fully turnkey with high-quality furnishings, the home appeals to short-term rental guests and private escapes alike. Modern appliances and durable finishes reduce maintenance while elevating guest experience, and the resort perks—clubhouse access, Guard Gated, and a premier location—enhance appeal. Proximity to dining, shopping, entertainment, and major highways adds convenience. This property blends premium design with a prime location and immediate move-in readiness. Don’t miss the opportunity to own a Windsor Island standout ready to perform from day one.

Listing is courtesy of: THE JERRY BARKER GROUP LLC (407-756-7296)

Listing Agent: Alyssa Barker (407-756-7296)