Location: Windsor At Westside, Kissimmee
Do Not Show Listings
2411 DUBAI ST, KISSIMMEE, FL 34747
$415,00064 Days on yellowkey MLS ID: O6398120
0 Days Off yellowkey (back on 4/23/2026)
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $579 Tax: $6,787 (2025)Community: Windsor At Westside Ph 3Townhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,787
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Lowest-Priced Fully furnished with high-end designer finishes. 5-Bedroom with Private Pool in Windsor at Westside! Welcome to this well-maintained 5-bedroom, 4.5-bathroom townhome built in 2020, located in the highly desirable Windsor at Westside resort community. This property stands out with a private screened-in pool and no rear neighbors, offering added privacy—an important feature for both homeowners and short-term rental guests. The first floor features a bedroom with full bath, ideal for guests or flexible use. The open-concept layout connects the kitchen, dining, and living areas, with sliding doors leading directly to the pool area. Upstairs includes a spacious loft and four additional bedrooms, including a primary suite and an ensuite bedroom, providing functional separation and comfort. Windsor at Westside offers resort-style amenities, including a clubhouse, lazy river, pool, fitness center, restaurant, sports courts, and more. Conveniently located near Disney, major highways, shopping, and dining, this home is well-suited for short-term rental investment, vacation use, or primary residence. Priced to sell and currently one of the best values in the community.
Listing is courtesy of: U S GLORY REALTY (407-222-7801)
Listing Agent: Rui Gao (407-222-7801)
1974 MAJORCA DR, KISSIMMEE, FL 34747
$444,900Listed 06/13/2026 11:00PM MLS ID: S5151890
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2265 Built: 2015Monthly Fee: $580 Tax: $6,044 (2025)Community: Windsor At Westside Ph 1Spa: NoTownhouse
Taxes:$6,044
Remarks: Welcome to 1974 Majorca Drive, located in the highly sought-after resort community of Windsor at Westside, where luxury vacation living meets exceptional investment potential. This home made such an impression on the current owners that they loved the lifestyle so much they ultimately decided to relocate here full time. Their change in plans creates an incredible opportunity for the next owner. Whether you're seeking a high-performing vacation rental, a second home, or a primary residence, this property checks every box. Despite being available for only a short period of time, the home is already producing strong rental revenue through a well-known, low-cost professional management company. Even better, there are numerous future bookings that can be transferred to the new owner when the current management company is retained, providing immediate income potential from day one. Originally intended to remain in the family's portfolio for years to come, the home has undergone several recent improvements and upgrades. Enjoy brand-new furnishings throughout many areas of the home, including a beautifully redesigned primary suite, a stylishly refreshed living room, a newly themed Disney bedroom, and an incredible Harry Potter themed loft and theater room that is sure to be a guest favorite. Additional updates include a brand-new washer and dryer, helping make this property completely turnkey. Step outside and enjoy your own private pool, perfect for relaxing after a day at the parks. Just steps away, the detached garage has been transformed into a dedicated game room, creating the ultimate entertainment space for family and guests. The combination of a private pool and game room significantly enhances both guest appeal and rental performance. The location is outstanding, just minutes from the world-class golf courses of ChampionsGate and Reunion Resort, Walt Disney World, shopping, dining, and major highways that provide convenient access to some of Florida's most beautiful beaches and attractions. As an added bonus, this home is one of the closest properties in Windsor at Westside to the community's renowned entertainment complex and resort amenities, making it especially convenient for owners and guests to enjoy everything the community has to offer. Windsor at Westside is renowned for its incredible resort amenities that attract guests year-round while providing an exceptional lifestyle for residents. Enjoy a resort-style pool, lazy river, splash pad, cabanas, bar and grill, fitness center, basketball, tennis, pickleball, scenic walking and jogging trails, concierge services, organized community events, and the peace of mind that comes with 24/7 live gated and roaming security. If you're looking for a property that offers immediate rental income, extensive upgrades, resort-style amenities, and the flexibility to serve as a vacation home or primary residence, 1974 Majorca Drive deserves a place at the top of your list.
Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)
Listing Agent: Jim Mcquade (407-906-6508)
2183 TRIPOLI CT, KISSIMMEE, FL 34747
$659,000336 Days on yellowkey MLS ID: S5130786
Bed: 9 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4391 Built: 2016Monthly Fee: $563 Tax: $12,617 (2024)Community: Windsor At WestsideSpa: YesSingle Family
Taxes:$12,617
Tax Year: 2024
Remarks: This spacious fully furnished 9-bedroom, 6-bathroom pool home is located in the sought-after Windsor at Westside Resort. One of the largest floor plans in the community, the home is ideal for large vacationing groups for investors and for your own pleasure. The open-concept floor plan features multiple living areas, a large upstairs loft/game room, and a modern kitchen with granite countertops, stainless steel appliances, and ample seating. The home includes themed bedrooms, generous sleeping capacity, and stylish furnishings throughout. The private screened-in pool and spa, complete with a covered lanai and outdoor dining area—perfect for relaxing or entertaining. Whether hosting guests or enjoying it personally, this outdoor space adds major rental appeal. Windsor at Westside offers resort-style amenities, including Clubhouse with restaurant and bar, with lazy river and water slide, fitness center, arcade, and sports courts, 24/7 manned security gate. With covered outdoor sitting, hot tub/spa, sand volley, basketball court, walking trails, store/ market place, it is Located only minutes from Walt Disney World! New laminate floors throughout the entire house! Come and take a look today!
Listing is courtesy of: AAA GLOBAL VENTURES PA (407-717-5232)
Listing Agent: Ann Yu (215-495-8939)
2070 ROME DR, KISSIMMEE, FL 34747
$459,000148 Days on yellowkey MLS ID: O6374736
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2265 Built: 2015Monthly Fee: $665 Tax: $7,966 (2025)Community: Windsor At Westside Ph 1Townhouse
Taxes:$7,966
Remarks: Welcome to luxury resort-style living in the highly desirable Windsor at Westside Resort community. This beautifully furnished two-story corner-unit home which is right next to the club house features a spacious open floor plan designed for both comfort and entertaining. Inside, enjoy professional interior design, quality furnishings, and a well-appointed layout including a large primary suite with a king-size bedroom and private en-suite bath. Additional bedrooms are generously sized, including two queen bedrooms, plus themed bedrooms ideal for family and guests. Step outside to your own private pool, perfect for relaxing under the Florida sun. The home also offers the convenience of a one-car garage. Owners enjoy access to Windsor at Westside’s premier amenities including a resort-style pool with splash area, lazy river, Tiki Bar, fitness center, clubhouse, arcade, sand volleyball, multi-purpose courts, onsite dining options, market/deli, and concierge services. Ideally located just minutes from Orlando-area attractions, dining, and shopping, this home offers the perfect combination of lifestyle and location.
Listing is courtesy of: INNOVATIVE REALTY, LLC (407-772-5555)
Listing Agent: Alberto Nikodimov (305-775-5522)
8825 RHODES ST, KISSIMMEE, FL 34747
$675,0003 Days on yellowkey MLS ID: S5151659
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2016Monthly Fee: $563 Tax: $11,485 (2025)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$11,485
Elementary School: Island Village Elementary School
High School: Celebration High
Middle School: Horizon Middle
Remarks: Welcome to 8825 Rhodes Street, 4041sqft beautifully maintained and fully furnished 8-bedroom, 6-bathroom home located within the highly sought-after gated Windsor at Westside Resort community. Designed for comfort, luxury, and entertainment, this spacious property features both upstairs and downstairs living areas, providing plenty of room for family and guests to relax and unwind. The open-concept kitchen showcases elegant granite countertops, ample cabinetry, and plenty of space for gathering and entertaining. Step outside to your private screened-in heated pool and covered lanai, creating the perfect setting for outdoor dining, family gatherings, or weekend BBQs while enjoying Florida's beautiful weather year-round. The converted garage has been transformed into a fun-filled game room, creating an additional entertainment space that guests and family members of all ages will enjoy. Whether you're searching for a primary residence, vacation home, or investment opportunity, this property offers exceptional flexibility and value. Residents enjoy access to all Windsor at Westside Resort amenities through the HOA, including a resort-style pool, clubhouse, fitness center, sports courts, playgrounds, and more. Ideally located approximately 8 miles from Walt Disney World Resort, this home offers convenient access to world-famous attractions, shopping, dining, golf, and major highways while providing the security and lifestyle of one of Central Florida's premier gated resort communities.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Jaden Ortiz (352-872-8181)
8956 ZURICH LN, KISSIMMEE, FL 34747
$575,00036 Days on yellowkey MLS ID: O6406521
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $577 Tax: $9,051 (2025)Community: Windsor At Westside Ph 3ASingle Family
Taxes:$9,051
Remarks: Location, location!!!!This fully furnished, turn-key 7-bedroom, 5.5-bathroom home offers 3,314 sq ft at Windsor at Westside a Gated Community. Enjoy an open-concept kitchen with stainless steel appliances and large island, a first-floor primary suite, and a spacious upstairs loft with 6 Bedrooms and 4 bathrooms Step outside to your private pool with brick pavers, covered patio, and screened lanai This beautiful 7-Bedroom 5.5-Bathroom comes fully furnished to make is turnkey for vacation investment property or simply as second home. Windsor at Westside a Gated Community. Located about 10-15 minutes from Disney World. Owners and guests enjoy unmatched amenities including an 8,000+ sq ft clubhouse, fitness center, resort-style pool, waterslide, lazy river, volleyball court, tennis courts, and a full activity-filled play zone. The HOA covers lawn maintenance, internet, cable, daily valet trash service, and access to all resort amenities Come and see it for yourself!
Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)
Listing Agent: Khadija Webber (407-592-2166)
2006 MAJORCA DR, KISSIMMEE, FL 34747
$439,000127 Days on yellowkey MLS ID: O6380751
1 Days Off yellowkey (back on 5/1/2026)
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2265 Built: 2015Monthly Fee: $579 Tax: $7,966 (2025)Community: Windsor At Westside Ph 1Spa: NoTownhouse
Elementary School: Westside K-8
Middle School: West Side
Remarks: Under contract-accepting backup offers. Welcome to this exceptional 5-bedroom, 4.5-bathroom vacation retreat featuring a private heated pool and outdoor kitchen with gas grill, thoughtfully designed for both refined relaxation and entertaining. This bright corner-unit home is filled with natural light and offers a spacious open-concept layout with ceramic tile throughout. The modern kitchen features stainless steel appliances and overlooks the main living and dining areas. The first floor includes a private bedroom with a full bathroom, ideal for guests or multi-generational living. Upstairs, the expansive primary suite offers an en-suite bathroom, along with a second en-suite bedroom, two additional bedrooms, and a shared full bath. Enjoy Florida living outdoors with a heated pool, pool-area half bath, and outdoor kitchen. A detached garage has been converted into a game room for added entertainment. Located just minutes from world-famous theme parks, this gated resort community offers exceptional amenities, including a resort-style pool with cabanas, lazy river, clubhouse with fitness center, on-site dining, sports courts, playground, and 24/7 security. Conveniently close to golf, shopping, dining, and major attractions. Perfect for families, groups, and vacationers looking for space, comfort, and resort-style fun close to all the action!
Listing is courtesy of: VIVA ORLANDO REALTY INC. (407-861-0000)
Listing Agent: Cassius De Moura (407-989-0007)
2428 DUBAI ST, KISSIMMEE, FL 34747
$419,000663 Days on yellowkey MLS ID: O6233761
REDUCED by $21,000 (4.8%) on 06/11/2026
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $605 Tax: $7,376 (2023)Community: Windsor At Westside Ph 3Townhouse
Taxes:$7,376
Tax Year: 2023
Remarks: Nestled Townhouse in Windsor at Westside, one of Kissimmee's premier short-term rental communities, this FULLY FURNISHED townhouse is your oasis of luxury and relaxation. With five spacious bedrooms and four and a half bathrooms, this stunning retreat offers the perfect blend of comfort and sophistication. As you step inside, you're greeted by an open floor plan that seamlessly integrates the living, dining, and kitchen areas. The kitchen boasts elegant granite countertops and sleek stainless steel appliances, creating a modern yet inviting atmosphere. The spacious loft upstairs provides an additional living area, perfect for relaxing, entertaining, or even setting up a home office. One of the highlights of this townhouse is the private pool, easily accessible through pool-facing telescopic sliding glass doors. Imagine unwinding by the poolside or retreating to the screened-in lanai for a serene evening under the stars. Staying in Windsor at Westside means enjoying world-class amenities. The HOA grants you access to an impressive 8,000 sq ft clubhouse, featuring a lazy river, sports courts, an arcade game room, and more. Dive into the zero-entry pool or treat yourself to a refreshing spa experience. Family will adore the playground and water slide, while adults can relax with a cocktail at the pool bar or dine at the full-service restaurant. To make your stay even more effortless, the HOA covers cable, high-speed internet, exterior maintenance, trash pick-up, pest control, and lawn care. Every detail has been thoughtfully curated to ensure your experience is nothing short of extraordinary. This townhouse isn't just a home; it's a lifestyle. Don’t miss out on the opportunity to own your own piece of paradise. Schedule a showing today and take the first step toward making this dream retreat yours.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Gladys Bezerra (407-701-4034)
1885 NICE CT, KISSIMMEE, FL 34747
$559,0003 Days on yellowkey MLS ID: O6415911
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2019Monthly Fee: $607 Tax: $10,159 (2025)Community: Windsor At WestsideSpa: YesSingle Family
Taxes:$10,159
Remarks: Welcome to resort-style living at its finest in the highly sought-after Windsor at Westside Resort! This beautifully maintained 6-bedroom, 4.5-bath pool home is offered fully furnished and turnkey, making it the perfect opportunity for a vacation home, investment property, or even a full-time residence just minutes from Walt Disney World and Central Florida's most popular attractions. Step inside and you'll immediately appreciate the bright, open-concept floor plan designed for gathering and entertaining. The spacious kitchen overlooks the dining and living areas, creating the perfect setting for family meals, celebrations, and relaxing evenings after a day of adventure. The first-floor primary suite offers a peaceful retreat complete with dual vanities, a soaking tub, separate shower, and direct access to the pool area for added convenience. The fun continues in the converted game room, where guests of all ages can enjoy a pool table, air hockey, and gaming stations, creating endless entertainment right at home. Outside, your private screened pool area provides the perfect place to unwind, soak up the Florida sunshine, or enjoy a relaxing evening swim. With no rear neighbors, you'll appreciate the added privacy while enjoying your own personal backyard oasis. Upstairs, a spacious loft serves as a second living and entertainment area, offering plenty of room for movie nights, gaming, or simply spreading out and relaxing. Five additional bedrooms provide comfortable accommodations for family and guests, including a second primary suite and two beautifully themed bedrooms featuring Star Wars and Princess-inspired décor that are sure to delight visitors of all ages. Beyond the home itself, Windsor at Westside offers an exceptional resort experience. This guard-gated community is renowned for its impressive amenities, including a spectacular resort-style pool, lazy river, clubhouse, fitness center, arcade, playground, sports courts, and scenic walking paths surrounding picturesque ponds. Whether you're enjoying a day at the resort or exploring nearby shopping, dining, golf, and world-famous attractions, everything you need is just moments away. Whether you're seeking a personal retreat, a high-demand vacation rental, or a combination of both, this outstanding property delivers the space, location, and amenities that today's buyers are looking for. Don't miss your opportunity to own a piece of paradise in one of Central Florida's premier vacation home communities!
Listing is courtesy of: FLORIDA RESORT REALTY LLC (863-255-2300)
Listing Agent: Danae Pitcher (863-255-2300)
8942 SYDNEY AVE, KISSIMMEE, FL 34747
$445,00040 Days on yellowkey MLS ID: O6404821
REDUCED by $13,000 (2.8%) on 06/10/2026
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2019Monthly Fee: $584 Tax: $6,808 (2025)Community: Windsor At Westside; Windsor/WestsideSpa: YesTownhouse
Taxes:$6,808
Remarks: TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: Newly upgraded laminate floor Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river Kids’ splash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between ChampionsGate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!
Listing is courtesy of: GOLDEN SUN REALTY INC (407-479-8898)
Listing Agent: Lucia Wu (407-765-2618)
8900 SYDNEY AVE, KISSIMMEE, FL 34747
$439,00051 Days on yellowkey MLS ID: O6401749
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2019Monthly Fee: $591 Tax: $5,607 (2025)Community: Windsor At WestsideTownhouse
Taxes:$5,607
Remarks: Welcome to 8900 Sydney Ave in Windsor at Westside, a beautifully positioned end unit 5 bedroom, 4.5 bath townhome offering 2,263 square feet in one of the most sought after vacation home communities near Disney. Originally purchased as the builder’s model, this home stands out from the typical inventory with a brighter, more elevated feel, a desirable end unit location, and interior finishes and furnishings that show far better than many competing townhomes in the community. The cream kitchen, stylish window treatments, upgraded bedroom theming, and strong overall presentation give this property the kind of visual appeal buyers and guests notice right away. Whether you are looking for a personal getaway, a second home, or an income producing vacation property, this townhome offers the combination of location, layout, and resort appeal that today’s buyers want. Windsor at Westside is a gated resort community with a large clubhouse, resort style pool, lazy river, waterslide, fitness center, tiki bar, arcade, and convenient access to the Disney parks, dining, and shopping. With its private pool, popular 5 bedroom layout, and premium end unit positioning, 8900 Sydney Ave is a standout opportunity in a community known for strong guest appeal and resort style living.
Listing is courtesy of: KRESSLER REAL ESTATE (407-864-2184)
Listing Agent: Andre Kressler (407-864-2184)
8881 RHODES ST, KISSIMMEE, FL 34747
$525,000156 Days on yellowkey MLS ID: TB8462660
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2016Monthly Fee: $563 Tax: $7,694 (2025)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$7,694
Remarks: 100K Dropped! This luxurious vacation home comes fully furnished with a beautiful upgraded custom furniture package including granite counter tops in the kitchen and all bathrooms, stainless steel appliances, tile throughout the main living area and all bathrooms, upgraded lighting fixtures in the kitchen and dining room area, custom themed rooms and interior paint, TVs in all rooms, beautiful screened pool area with paver deck and covered lanai. All appliances are energy efficient along with energy efficient (15 seer) air conditioning units, LOW-E dual pane windows and much more. Amenities include: 8000 square foot resort style clubhouse, resort style heated pool and spa, wireless internet on the pool deck, lazy river, state of the art fitness center, poolside cabana's, on site store, playground, volleyball, tennis, basketball, game room, restaurant, bar, relaxing lounge area with indoor/outdoor fireplace, TVs and much more. The house is an active rental program, very popular with vacationers. All homes at Windsor at Westside include: fully maintained landscaping, internet, cable and daily garbage pick up. This community is located minutes from Walt Disney World, golf courses, shopping, grocery stores, the airport and all major attractions.
Listing is courtesy of: BRIGHT REALTY GROUP LLC (813-240-7744)
Listing Agent: Yongkai Zheng (678-979-6850)
8936 PRAGUE WAY, KISSIMMEE, FL 34747
$550,0006 Days on yellowkey MLS ID: O6414964
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2019Monthly Fee: $721 Tax: $8,850 (2025)Community: Windsor At Westside Ph 3Single Family
Taxes:$8,850
Remarks: Fully furnished and rental-ready, this spacious 6-bedroom, 4.5-bathroom corner lot pool home is located within a sought-after resort community that permits short-term rentals. Offering over 3,100 square feet of living space and access to extensive resort amenities, this property is well-positioned for use as a vacation home or investment property. The open floor plan features a spacious kitchen with stainless steel appliances, a breakfast bar, and ample cabinet and counter space. The kitchen flows seamlessly into the main living areas, creating an ideal setting for entertaining and accommodating larger groups. The primary suite includes a walk-in closet and an ensuite bathroom with dual vanities, a soaking tub, and a separate shower. Additional bedrooms and bathrooms provide flexibility for multiple guests and a variety of sleeping arrangements. Outside, guests can enjoy a private pool and patio area, while the corner lot location offers additional space and curb appeal. The property is being offered fully furnished, providing a convenient opportunity for buyers seeking a turnkey, rental-ready investment. Community amenities include a clubhouse, fitness center, game room, basketball court, restaurant, multiple resort-style pools, a lazy river, waterslide, and recreational areas. One of the community pools is conveniently located within walking distance of the home. The property is also located near shopping, dining, golf, major roadways, and Central Florida attractions. This property offers the opportunity to own a spacious, fully furnished pool home in a resort community that permits short-term rentals.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Cristina Perez Rodriguez (407-724-3684)
8912 RHODES ST, KISSIMMEE, FL 34747
$520,00053 Days on yellowkey MLS ID: S5148044
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2016Monthly Fee: $607 Tax: $10,299 (2025)Community: Windsor At Westside Ph 1Single Family
Taxes:$10,299
Remarks: Short Sale. Welcome to Windsor at Westside — Guard-Gated Resort Living at its Finest! This fully furnished, turn-key 7-bedroom, 5.5-bathroom home offers 3,314 sq ft of beautifully appointed living space, perfect for short-term rental income or a luxury vacation retreat. Enjoy an open-concept kitchen with stainless steel appliances and large island, a first-floor primary suite, and a spacious upstairs loft. Step outside to your private south-facing pool with brick pavers, covered patio, and screened lanai. Premium lot with easy access to resort amenities including waterslide pool, lazy river, Tiki bar, fitness center, arcade, and more — all just minutes from Walt Disney World. Fully furnished | Turn-key | STR-friendly | Don't miss this one!
Listing is courtesy of: EXP REALTY LLC (407-674-7777)
Listing Agent: Walter Parraga (407-764-0245)
8887 GENEVE CT, KISSIMMEE, FL 34747
$399,000439 Days on yellowkey MLS ID: O6295445
REDUCED by $36,000 (8.3%) on 06/08/2026
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2265 Built: 2018Monthly Fee: $560 Tax: $7,963 (2024)Community: Windsor At Westside Ph 2BSpa: YesTownhouse
Taxes:$7,963
Remarks: Stunning, FULLY FURNISHED home located in the much sought after gated community of Windsor at Westside. This beautiful home is meticulously furnished and beautifully decorated. It also boasts 5 bedrooms, and 4.5 bathrooms, an open floor concept, a large fully equipped kitchen with granite countertops, stainless-steel appliances, and an island kitchen linked to the family room and dining room. Conveniently, the first floor has one bedroom and a full bathroom. Upstairs you will find 4 bedrooms, including the master bedroom, plus an additional loft, great for relaxation. Enjoy the back enclosed pool area which offers amazing conservation views with much privacy. Perfect for entertaining or relaxing. The resort offers a state-of-the-art, approximately 10,000 sqft clubhouse. The amenities include a lazy river, thrilling water park, resort style pool, fitness center, tennis/basketball courts, playground, restaurant, bar and and ice cream shop. It's like being on vacation all year around! Located just minutes away from the enchantment of Disney Parks, great schools, great dining and shopping.
Listing is courtesy of: ORLANDO REGIONAL PROPERTY MANAGEMENT (407-800-4545)
Listing Agent: Jeannette Lopez (407-800-4545)
9047 RHODES ST, KISSIMMEE, FL 34747
$399,000100 Days on yellowkey MLS ID: S5145124
0 Days Off yellowkey (back on 4/29/2026)
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2102 Built: 2016Monthly Fee: $516 Tax: $7,751 (2025)Community: Windsor At Westside Ph 1Spa: NoTownhouse
Taxes:$7,751
Remarks: Resort style living! Perfect for primary residence and an investment opportunity. This modern Town home is located in one of the newest resort communities in the Kissimmee/Orlando area. Just 8 miles from Disney, and within easy reach to all the attractions, shopping, and dining in the Disney area. This 24 hour guard gated resort provides a fabulous water park, 10,000 sq.ft. Clubhouse with Fitness Center, Resort-style heated Pool with Lazy River, Tiki Bar & Spa, Volleyball Court & Multi-Purpose Sports Courts. The home features 4 bedrooms 3 and half bathrooms, open floor plan, it is very new and furnished with modern comfort in mind. A guest bedroom with a full bathroom is located on the first floor. Upstairs you will find the remaining bedrooms, including a Harry Potter themed room. The rooms are arranged around a central large loft area, that is ideal for everyone to relax and play games. The technology in the home is all new, with 6 TVs, a Sony Playstation 4, DVD player and of course Free and Fast WiFi and free local and long distance calling to the USA and Canada. Lounge outside, at your own private pool, enjoy a relaxing conversation, a swim or just enjoy the south facing pool. We are also steps away from the club house, which has everything from a large pool, cabanas, lazy river, game arcade, cafe & bar, and gym. This is a perfect investment or residential opportunity. The home is currently on a short term rental program and has a great potential! Rental history available by request. Call and schedule your private tour today or enjoy a virtual walk through with our Matter port tour!
Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)
Listing Agent: Stani Delcheva (407-405-6815)
1864 NICE CT, KISSIMMEE, FL 34747
$695,90067 Days on yellowkey MLS ID: O6396750
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2018Monthly Fee: $607 Tax: $11,733 (2025)Community: Windsor At Westside Ph 2ASpa: YesSingle Family
Taxes:$11,733
Remarks: Welcome to 1864 Nice Ct, Davenport, FL - this 8-bedroom, 6-bath, 4,041 sq ft turnkey vacation home at Windsor at Westside is just 20 minutes from Orlando’s top theme parks. Perfect for large groups, this home comfortably sleeps up to 20 guests, offering the ultimate combination of comfort, space, and Florida-style fun. The open-concept great room brings everyone together with a gourmet kitchen, living, and dining area designed for entertaining or relaxing after a day at the parks. Both the first-floor and second-floor primary suites provide privacy and luxury, while the remaining bedrooms are perfectly set up for groups. Step outside to your fully enclosed pool and spa with lake views, ideal for sun-soaked afternoons, poolside dinners, or evening relaxation. The home is fully furnished and move-in ready, making it an effortless turnkey option for a second home, vacation rental, or short-term rental investment. Upstairs, the family room ensures there’s plenty of room for everyone to spread out comfortably and create memories together. Windsor at Westside Resort offers resort-style amenities that elevate the vacation experience, including a 10,000 sq ft clubhouse, zero-entry pool with waterslide, lazy river, splash park, lake and pier, tiki bar & fireplace lounge, fitness center, volleyball courts, and daily maintenance included in the HOA. This is a rare opportunity to own a fully furnished, move-in-ready, large-group vacation home in one of Orlando’s most sought-after resort communities. Schedule your private showing today and experience the perfect blend of Florida lifestyle, turnkey convenience, and rental income potential!
Listing Agent: Matt Dixon (407-965-8906)
2015 MAJORCA DRIVE, KISSIMMEE, FL 34747
$412,90051 Days on yellowkey MLS ID: S5148415
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2263 Built: 2016Monthly Fee: $580 Tax: $7,670 (2025)Community: Windsor At WestsideSpa: NoTownhouse
Taxes:$7,670
Remarks: Welcome to your slice of paradise at Windsor at Westside! Fully furnished and Airbnb-ready, this spacious 5-bedroom, 4.5-bath townhome with a private pool is located in one of Greater Orlando’s most sought-after short-term rental communities. Designed to comfortably accommodate 14+ guests, this property is ideal as both a personal getaway and an income-producing investment. The open-concept floorplan creates a bright, inviting atmosphere, enhanced by modern finishes and ample space for gathering and entertaining. Step outside to your private screened-in pool—perfect for unwinding after a day at the parks or enjoying Florida’s year-round sunshine in total privacy. The HOA delivers exceptional value, covering cable, internet, trash removal, lawn care, and 24/7 guard-gated security, offering a truly low-maintenance ownership experience. Residents and guests enjoy access to world-class resort amenities, including a 10,000 sq. ft. clubhouse, resort-style pool with lazy river and splash zone, hot tub, fitness center, arcade, sports courts, sand volleyball, playground, on-site market and deli, concierge services, and the popular Tu Casa Tiki Bar. Ideally located just minutes from Walt Disney World, with easy access to shopping, dining, and major attractions, this property offers the perfect blend of lifestyle and investment potential. Whether you’re expanding your short-term rental portfolio or searching for a vacation home that pays for itself, this opportunity checks all the boxes. Schedule your private showing today.
Listing is courtesy of: REALTY ONE GROUP INSPIRATION (321-233-2300)
Listing Agent: Fernando Peralta (267-474-7628)
2414 DUBAI ST, KISSIMMEE, FL 34747
$428,0008 Days on yellowkey MLS ID: O6414579
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2265 Built: 2020Monthly Fee: $560 Tax: $7,109 (2025)Community: Windsor At Westside Ph 3Townhouse
Taxes:$7,109
Remarks: Priced to sell! This stunning home sits in the third and newest phase of the sought-after Windsor at Westside Resort, with also a Private Heated Pool. Featuring 5 bedrooms and 4 bathrooms, it offers the perfect blend of fun and relaxation. One bedroom and bathroom are conveniently located on the first floor, while the remaining 4 bedrooms—including some with fun themed designs—are upstairs, just off the family room. The resort amenities include heated pools, a heated jacuzzi, a heated lazy river, and a full tiki bar at the pool complex. Whether you’re looking for a turnkey short-term rental investment or a second home to call your own, this property is zoned for both.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Caroline De Castro Marcellini (561-319-9009)
8904 SYDNEY AVE, KISSIMMEE, FL 34747
$445,0009 Days on yellowkey MLS ID: O6413060
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2019Monthly Fee: $584 Tax: $6,738 (2025)Community: Windsor At Westside; Windsor/WestsideSpa: YesTownhouse
Taxes:$6,738
Remarks: TURN-KEY SHORT-TERM RENTAL | FULLY FURNISHED | SOUTH-FACING POOL| NO CARPET Welcome to this exceptional 5-bedroom, 4.5-bathroom townhome—a true turn-key investment opportunity or vacation retreat, professionally designed and ready to generate income from day one. Property Highlights: Upgraded laminate floor; new dryer/washer (2025); two new king bed and bunkbed Star War theme in loft; Harry Potter theme and Disney Cruise theme in tow rooms Highly desirable 5-bedroom floor plan with one bedroom conveniently located on the first floor Private south-facing pool—perfect for all-day sunshine and guest enjoyment Half bath on the patio for added convenience by the pool area Spacious loft area—themed star war for a game room with sofa and TV Upgraded kitchen with modern cabinetry and countertops Professional furniture package included—stylish, cohesive, and rental-ready by a professional Community & Resort Amenities: Access to TWO resort-style pools—one within the subdivision and another at the main clubhouse Stunning Mediterranean-style recreation center featuring: Grand lobby Resort-style pool with lazy river plash zone Indoor/outdoor restaurant & bar Fitness center Outdoor fireplace, sports courts, and playground Prime Location: Ideally situated between Champions Gate and US-192 Easy access to I-4, Walt Disney World, and Orlando International Airport Minutes from shopping, dining, golf courses, and major attractions Whether you're looking for a high-performing short-term rental, a vacation getaway, or a second home, this property checks every box with its unbeatable layout, location, and amenities. Schedule your showing today—this one won’t last!
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