Windsor Island Residence Homes under $500,000

Windsor Island Residence Homes under $500,000

Welcome to Windsor Island Residence, an enchanting subdivision nestled in the heart of Davenport, Florida, within the picturesque Polk County. This vibrant community is an ideal haven for families, retirees, and anyone seeking a serene lifestyle infused with the charm of Florida living.

Windsor Island Residence boasts beautifully designed homes that cater to a variety of tastes and preferences, and the best part? You can find stunning properties priced under $500,000! This makes it an exceptional opportunity for first-time homebuyers and those looking to invest in a vacation rental or second home in the Sunshine State.

Each residence is crafted with modern amenities and thoughtful layouts, ensuring comfort and style for all residents. The community is surrounded by lush landscapes and offers access to a range of recreational facilities, including community pools, parks, and walking trails. Families will appreciate the proximity to top-rated schools, shopping centers, and dining options, making daily life convenient and enjoyable.

Davenport is also strategically located near major attractions such as Walt Disney World, Universal Studios, and beautiful Florida beaches, allowing residents to indulge in a wealth of entertainment and leisure activities.

With its inviting atmosphere, affordable housing options, and prime location, Windsor Island Residence is not just a place to live, but a place to thrive. Explore this charming community today and discover your dream home in Florida!

Newest Windsor Island Residence Homes under $500,000

1206 Aloha Boulevard, Davenport
$499,900
5 Beds ⋅ 6 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Welcome to your own private retreat in Davenport’s sought-after gated, resort-style community, where luxury, comfort, and endless entertainment come together in one incredible destination. This fully furnished, turnkey 5-bedroom, 5½-bathroom private pool home is designed for both unforgettable family vacations and outstanding short-term rental potential. With spacious accommodations, upscale furnishings, and a large private heated pool, this home offers the perfect combination of privacy and resort-style living. Beyond your private retreat, residents and guests can enjoy an impressive collection of hotel-inspired resort amenities, including a spectacular resort-style pool, fun splash park, thrilling waterslides, lazy river, fitness center, pickleball courts, beach sand volleyball, mini golf, tiki bar, and so much more. There is truly something for everyone... from relaxing poolside to keeping the whole family entertained from morning until night. Located just a short drive from Walt Disney World’s world-famous theme parks, the home is also conveniently close to an abundance of restaurants, shopping, entertainment, and other Central Florida attractions. Whether you’re looking for a personal vacation home, an investment property, or a turnkey short-term rental, this property offers an exceptional opportunity to own a piece of the Central Florida vacation lifestyle. Fully furnished. Private pool. Resort amenities. Gated community. Close to Disney. Turnkey and ready to enjoy or rent. Your dream Florida getaway and potentially your next investment awaits.

1206 Aloha Boulevard, Davenport
936 Paradise Drive, Davenport
$459,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
237 Jetty Way, Davenport
$399,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
716 Gardenia Lane, Davenport
$489,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
267 Jetty Way, Davenport
$399,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
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
616 Jasmine Lane, Davenport
$459,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Welcome to your perfect Florida escape — a beautifully maintained 5-bedroom, 4.5-bath townhome nestled within the sought-after Windsor Island Resort, just steps from the community’s coveted clubhouse. Whether you’re searching for a vacation retreat or income-producing investment property, this home checks every box. Thoughtfully cared for and move-in ready, this spacious townhome offers generous living spaces designed for both relaxation and entertaining. The open-concept main floor flows effortlessly to your private west-facing splash pool — the ideal spot to unwind each evening as the Florida sun sets after a magical day at Walt Disney World, Universal Studios, or any of the area’s world-class attractions, all just minutes away. Five well-appointed bedrooms provide ample room for family and guests, while four and a half baths ensure everyone’s morning routine runs smoothly. The prime location within the resort means the award-winning clubhouse — complete with a water park, restaurant, fitness center, and more — is literally right outside your door. Highlights: • 5 bedrooms / 4.5 bathrooms • Private west-facing splash pool — perfect for golden-hour relaxation • Steps to the Windsor Island Resort Clubhouse & water park amenities • Minutes to Walt Disney World, Universal Studios & area theme parks • Well-maintained and vacation-rental ready • Ideal as a vacation home or investment property Don’t miss this opportunity to own a piece of one of Central Florida’s most desirable resort communities. Schedule your private showing today!

616 Jasmine Lane, Davenport
967 Paradise Drive, Davenport
$465,000
5 Beds ⋅ 4 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Welcome to this stunning 5-bedroom, 4.5-bathroom vacation pool retreat located in the highly sought-after Windsor Island Resort community in Davenport, FL. Short walk to clubhouse! This fully furnished, turnkey home boasts a bright open-concept layout, a modern gourmet kitchen with stainless steel appliances, and a spacious living area perfect for entertaining. Upstairs, a large loft offers additional space for relaxation, while the private screened-in pool and covered lanai create the ultimate Florida getaway. As part of the resort community, owners and guests enjoy access to world-class amenities including a clubhouse, lazy river, water slides, fitness center, and sports courts. Conveniently located just minutes from Disney World, restaurants, and shopping, this property is ideal as a short-term rental investment or personal vacation home. Don’t miss the chance to own this beautiful income-generating property in one of Central Florida’s most desirable vacation communities!

967 Paradise Drive, Davenport
886 Paradise Drive, Davenport
$495,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Welcome to Windsor Island Resort—where luxury, location, and lifestyle come together in one of Central Florida’s most sought-after vacation communities. Perfectly positioned just moments from the clubhouse, this beautifully updated and professionally themed 5-bedroom, 4.5-bath townhome offers not only convenience, but a true resort experience right at your doorstep. Built in 2021 and offered fully furnished and turn-key, this home stands out with its tasteful upgrades and eye-catching themed rooms designed to elevate both guest experience and rental performance. The open-concept layout features a bright and spacious living area that flows seamlessly into a modern kitchen complete with granite countertops, oversized island, stainless steel appliances, and ample seating—ideal for entertaining or hosting large groups. Step outside through sliding glass doors to your private screened-in pool and lanai, creating the perfect indoor-outdoor living space. With direct access to a convenient pool bath, this setup is designed for both comfort and functionality. Downstairs, you’ll find one bedroom and a full bath for added convenience, while upstairs features additional bedrooms, including spacious suites, along with a versatile loft/game area—perfect for relaxing after a day at the parks. Each space has been thoughtfully designed with stylish finishes and high-quality furnishings, making this home truly move-in or rental ready. Located just a short walk to the resort’s world-class amenities, Windsor Island offers an unmatched lifestyle featuring a resort-style pool, lazy river, water slides, splash pad, fitness center, mini golf, arcade, sports courts, tiki bar, and on-site dining. Guests and owners alike enjoy the convenience of being minutes from Disney, major attractions, shopping, and dining. Whether you’re looking for a high-performing short-term rental or your own private vacation retreat, this home checks every box—with premium location, standout design, and exceptional amenities

886 Paradise Drive, Davenport
830 Paradise Drive, Davenport
$479,000
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Welcome to 830 Paradise Drive, an exceptional professionally decorated vacation home located in the highly sought-after Windsor Island Resort. This spacious and beautifully furnished property offers 5 bedrooms and 4.5 bathrooms, featuring an open-concept floor plan perfect for entertaining and enjoying quality time with family and friends. All furniture and décor are included in the sale, making this a true turn-key opportunity. The modern kitchen features abundant cabinet space, granite countertops, stainless steel appliances, and a convenient breakfast bar. The bright living area flows effortlessly to the outdoors through sliding glass doors, leading to a covered lanai and a screened-in heated pool— complete with a dedicated half bath accessible from the lanai for added convenience. Upstairs, you’ll find a generous primary suite, two additional bedrooms, and a versatile loft area ideal for a game room, family lounge, or entertainment space. Windsor Island Resort offers world-class amenities, including a spectacular resort-style pool, water slides, splash zone, lazy river, playground, and much more—ensuring comfort, fun, and unforgettable experiences. All of this is just minutes from Disney and Central Florida’s most iconic attractions. Whether you're seeking a personal vacation retreat or a high-performing investment property, this fully furnished, turn-key home is ready for you. Schedule your private showing today!

830 Paradise Drive, Davenport
236 Jetty Way, Davenport
$449,900
5 Beds ⋅ 5 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Get ready to be enchanted by this magnificent 5-bedroom, 4.5-bathroom townhome ,nestled in the Windsor Island Resort — a coveted address blending luxury and comfort! This home comes equipped with a fully installed solar panel system, offering significant savings on electricity bills and a more sustainable lifestyle. Just a short walk from the clubhouse, this stunning home is designed with modern sophistication, making it perfect for families seeking unforgettable memories or investors looking for a high-return short-term rental property. Enjoy spacious living areas, contemporary finishes, and a private outdoor retreat, ideal for relaxation. Windsor Island Resort elevates your experience with world-class amenities: a vibrant clubhouse, lazy river, water slides, state-of-the-art fitness center, mini golf, and more — all just minutes from Orlando’s top attractions and Central Florida’s highlights. Whether you’re turning it into your dream vacation getaway or securing a lucrative rental income, this townhome is a must-see jewel! Schedule your visit and fall in love with this tropical paradise.

236 Jetty Way, Davenport
107 Jetty Way, Davenport
$499,000
5 Beds ⋅ 4 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Short Sale. Investor opportunity in the sought-after Windsor Island Resort! Fully furnished 5-bedroom, 4-bath townhome ideal for use as a vacation home or income-producing short-term rental. This spacious and functional layout is designed to accommodate guests comfortably and maximize rental appeal. Located in a premier resort-style community featuring a clubhouse, resort pool, lazy river, water park, fitness center, sports courts, and more. The property is turnkey and furnished, allowing for immediate rental operations or personal vacation use. Conveniently located near major attractions, shopping, dining, and main roadways. A strong addition to any investment portfolio in a high-demand vacation rental market.

107 Jetty Way, Davenport
126 Jetty Way, Davenport
$489,000
5 Beds ⋅ 4 Baths ⋅ Windsor Island Residence SubDv. ⋅ 33897 Zip Code
Price to Sell!!Welcome to this exceptional 5-bedroom, 4.5-bath townhome in the popular Windsor Island Resort, one of the most sought-after vacation destinations near Disney World! Professionally decorated and fully furnished, this luxurious property is turn-key ready, offering the perfect retreat for vacationers or a prime opportunity for short-term rental income. This unit boasts one of the best locations in the community, just a short walk to the clubhouse and offering exceptional privacy with no rear neighbors. The open-concept layout features stylish living spaces, a modern kitchen with upgraded appliances, and beautifully appointed bedrooms designed for relaxation. Guests will also love the premium resort amenities, including a lagoon-style pool, lazy river, splash pad, mini-golf, fitness center, and more! Located just minutes from Disney parks, shopping, dining, and entertainment, this townhome offers a rare blend of comfort, convenience, and resort-style living in the heart of Orlando’s top vacation area.

126 Jetty Way, Davenport
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