Location: Windsor At Westside, Kissimmee
Do Not Show Listings
8824 BENGAL CT, KISSIMMEE, FL 34747
$610,000268 Days on yellowkey MLS ID: O6353390
REDUCED by $60,900 (9.1%) on 07/03/2026
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2019Monthly Fee: $550 Tax: $12,811 (2024)Community: Windsor At Westside Ph 2B-1Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,811
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Short Sale. Make your dream a reality. Enjoy this Luxury, conveniently located, Central Florida lifestyle Home. Property can be, and currently is, used as a short-term vacation rental.
Listing is courtesy of: VMY REALTY INC (407-412-4164)
Listing Agent: Eugene Vilkovskiy (407-412-4164)
1921 NICE CT, KISSIMMEE, FL 34747
$510,000240 Days on yellowkey MLS ID: S5138553
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2019Monthly Fee: $698 Tax: $10,704 (2024)Community: Windsor At Westside Ph 2ASingle Family
Taxes:$10,704
Remarks: Fully Furnished Pool and Spa Home. A fantastic choice to be your Vacation Home or Rental Property in the Windsor at Westside Resort! 6 Bedrooms - 4.5 Bathrooms and a Gorgeous Loft. Private Heated Pool and Spa with a great view from your pool deck area. As you step inside, you are greeted by a foyer and entrance high ceiling. The main level features a master bedroom with a bathroom that connects to the pool area, perfect for accommodating guests. A conveniently located half bathroom adds to the overall functionality of this level. Continuing on, you'll discover a spacious and open-concept living area that seamlessly connects the family room, dining area, and kitchen. The kitchen is equipped with stainless steel appliances, abundant counter space, and a breakfast bar, making it a central hub for culinary adventures and social gatherings. Upstairs you will find the large loft with TV, coach and a nice bar table, 1 more en-suite (second master bedroom) and 4 more bedrooms (2 of them Themed Bedrooms) sharing two more bathrooms. This home features a heated private pool/spa, a large covered Lanai with patio furniture and sun loungers, tile roof and furnished. The Windsor at Westside Resort is a Gated Community with a great Clubhouse for vacationers, and features amenities including a lazy river, splash pool, bar, gym, game room and more. This is a great vacation home, very close to other area attractions. Schedule your visit NOW. Stunning Home.
Listing is courtesy of: FLORIDA SPIRIT HOMES (407-396-4441)
Listing Agent: Gabriel Silva Andrada (321-666-0301)
2147 TRIPOLI CT, KISSIMMEE, FL 34747
$658,00070 Days on yellowkey MLS ID: S5149067
REDUCED by $40,000 (5.7%) on 07/01/2026
Bed: 9 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4391 Built: 2016Monthly Fee: $563 Tax: $11,982 (2025)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$11,982
Tax Year: 2025
Remarks: The largest home on one of the best lots in entire Windsor at Westside resort. This fully furnished/equipped home with private pool deck, is just stone throw away from fabulous clubhouse and resort amenities. Brand new Duralux water proof flooring throughout second floor and ground floor bedrooms. UPGRADED CABINETRY throughout. Large private pool deck, heated pool and spa are ideal for entertaining large group of guests. Wide open game room equipped with wet bar and fridge. Dark granites for kitchen and bathroom counters, stainless steel appliances including two full size french door fridges, 42" cabinets and high ceilings. Windsor at Westside resort features state of art Clubhouse, 24 hour guarded gate, restaurant, bar, scheme park style water park. This home could be your ideal second home or the dream vacation rental investment property you’ve been looking for.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Shawn Huang (512-804-9960)
8811 GENEVE CT, KISSIMMEE, FL 34747
$399,999102 Days on yellowkey MLS ID: S5146973
0 Days Off yellowkey (back on 5/23/2026)
REDUCED by $10,001 (2.4%) on 05/01/2026
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2018Monthly Fee: $579 Tax: $6,358 (2025)Community: Windsor At Westside Ph 2BSpa: NoTownhouse
Taxes:$6,358
Remarks: Under contract-accepting backup offers. Welcome to Windsor at Westside, one of Central Florida’s most desirable short-term vacation communities! Ideally located just minutes from world-famous theme parks, shopping, dining, and entertainment, this stunning 5-bedroom, 4 full bath and 1 half bath home offers the perfect blend of luxury and convenience. Fully furnished and move-in ready, this property is ideal as an income-producing vacation rental or a beautiful second home getaway. Enjoy your own private pool, perfect for relaxing after a day of fun in the sun. The community offers exceptional resort-style amenities, including a lazy river, water playground, cabanas, outdoor fireplace, shaded playground, fitness center, arcade, multi-purpose courts, sand volleyball, Tu Casa Bar & Lounge, event spaces, and a lush sports field. Don’t miss this incredible opportunity to own in a prime location just a short distance from Disney World parks—where comfort, entertainment, and investment potential come together!
Listing is courtesy of: MAGNUS REALTY GROUP LLC (407-286-6042)
Listing Agent: Manuel Minier (407-340-0966)
8869 RHODES ST, KISSIMMEE, FL 34747
$559,000191 Days on yellowkey MLS ID: O6369898
0 Days Off yellowkey (back on 7/1/2026)
REDUCED by $51,000 (8.4%) on 04/26/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2016Monthly Fee: $552 Tax: $11,004 (2024)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$11,004
Elementary School: Westside Elem
High School: Celebration High
Middle School: West Side
Remarks: Under contract-accepting backup offers. Ideally positioned within the highly sought-after Windsor at Westside resort community, this exceptional FULLY FURNISHED pool home offers an outstanding opportunity as the perfect blend of personal enjoyment and investment potential, whether used as a vacation home, seasonal escape, or profitable rental property. Walking distance from the community’s clubhouse, which offers resort-style amenities, this home combines prime location, strong rental performance, and extensive recent upgrades. This property is operating as an Airbnb and producing impressive revenue numbers when rented, driven largely by its ideal location within the community, beautiful water views in front and back, and the thousands of dollars invested into updates and improvements. Rental projections continue to look strong in the area, creating immediate income potential with room for future growth. For added convenience, any future bookings may be transferable if the current management company is retained, allowing for a seamless transition and potential day-one revenue for the next owner. Unlike many vacation homes on the market, this property has been extensively upgraded to maximize guest appeal and long-term durability. Featuring over $40,000 in improvements, the home includes luxury vinyl flooring throughout all bedrooms and upstairs living spaces, with NO CARPET except the updated stairway, along with refreshed furnishings and décor, fresh interior paint, new appliances, smart televisions, Nest thermostats, Schlage smart locks, LED lighting, security cameras, new linens, flatware, and more. Professionally themed bedrooms and upgraded entertainment spaces further enhance the guest experience. Spanning over 3,100 square feet, this spacious 6-bedroom, 4.5-bathroom home was designed for comfort, functionality, and entertaining. The open-concept layout flows seamlessly between the kitchen, dining, and living areas before opening to the private screened lanai with heated pool and spa. The thoughtfully designed floor plan includes two primary suites, including a first-floor owner's suite featuring dual sinks, soaking tub, and separate walk-in shower. Upstairs, additional guest rooms, themed spaces, and an oversized loft create the perfect entertainment area complete with a large-screen television and additional refrigerator. Outdoor living is equally impressive with upgraded patio furnishings, privacy screens, a pool alarm system, and a remote-controlled pool heater. Residents and guests of Windsor at Westside enjoy a 10,000-square-foot clubhouse, resort-style pool and spa, lazy river, water slide, arcade, tiki bar and restaurant, fitness center, sports courts, playground, and more. HOA dues include landscaping maintenance, cable, internet, pest control, daily valet trash service, and man gated security, creating a low-maintenance ownership experience, making it truly turn-key. Conveniently located just 20 minutes from Walt Disney World, shopping, dining, golf, major highways, 30 minutes from Orlando International Airport, and Florida’s world-famous attractions, this property truly checks every box for both lifestyle and investment performance. The hard work has been done for you! Schedule your private showing today and be sure to explore the virtual tour and 3D walkthrough links for a complete look inside this incredible property.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Lisa Mahjoub (321-217-9965)
8901 RHODES ST, KISSIMMEE, FL 34747
$550,000390 Days on yellowkey MLS ID: O6319078
REDUCED by $15,000 (2.7%) on 05/08/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2016Monthly Fee: $553 Tax: $6,382 (2024)Community: Windsor At Westside Ph 1Single Family
Taxes:$6,382
Remarks: Welcome to your dream Oasis at Windsor at Westside! This professionally decorated, fully furnished 6-bedroom, 4 1/2-bathroom retreat is located just steps from the resort’s clubhouse, placing world-class amenities right at your doorstep. Designed with luxury and comfort in mind, this home boasts two spacious primary suites—one on the main floor and another upstairs—offering ultimate flexibility for guests. You'll love the the open floor plan, upscale furniture, no carpet throughout the home (ideal for easy maintenance and higher booking potential), and a converted garage arcade room for endless family fun. Upstairs, the versatile loft space serves as a movie theater, game room, or a relaxing lounge area. Step outside to your private heated pool and spa, perfect for soaking up the Florida sun year-round. Windsor at Westside offers resort-style living with a 10,000 sq. ft. clubhouse, state-of-the-art fitness center, lazy river, splash area, Tiki Bar, Tu Casa Bar & Lounge, market and deli, arcade, sand volleyball, multipurpose courts, and a playground—everything your guests need for a memorable stay. Location is unbeatable—just minutes from Walt Disney World, 25 minutes away from Epic Universe theme park, and close to shopping, dining, grocery stores, and entertainment. Whether you’re looking for a top-performing short-term rental or a private vacation escape, this home has it all! Call us now for a private tour.
Listing is courtesy of: RIVA REALTY GROUP LLC (407-845-1003)
Listing Agent: Camila Riva (407-765-3656)
8936 PRAGUE WAY, KISSIMMEE, FL 34747
$549,00034 Days on yellowkey MLS ID: O6414964
REDUCED by $1,000 (0.2%) on 06/26/2026
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
Elementary School: Westside K-8
Middle School: Horizon Middle
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)
8952 ADRIATICO LN, KISSIMMEE, FL 34747
$435,000228 Days on yellowkey MLS ID: O6363446
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2263 Built: 2017Monthly Fee: $580 Tax: $7,726 (2025)Community: Windsor At Westside Ph 1Spa: NoTownhouse
Taxes:$7,726
Remarks: Welcome to 8952 Adriatico Lane, a fully furnished 5-bedroom, 4.5-bath townhome in the highly desirable gated community of Windsor at Westside. Offering turnkey luxury, modern upgrades, and a proven history of successful short-term rental performance, this property stands out as an exceptional opportunity for both investors and personal-use buyers. The main level features an open-concept layout with a spacious living area and a well-appointed kitchen complete with granite countertops, stainless steel appliances, and a large central island ideal for gathering. This floor also includes a bedroom and full bathroom, providing convenient accommodations for multi-generational families or high-occupancy rental groups. Sliding glass doors lead to the private, screened-in splash pool and covered lanai, which also includes a dedicated half bathroom for easy poolside access. Upstairs, brand-new carpeting enhances the comfort of the bedrooms and loft area. The floor plan includes a generous primary suite along with additional guest rooms suited for families or vacation rental guests. Recent upgrades include a new dryer and a newly installed EV charging plug. High-quality furnishings and décor are included with the sale, ensuring immediate rental readiness or a seamless second-home transition. Windsor at Westside offers a premier resort lifestyle with an 8,000 sq ft clubhouse, heated zero-entry pool, lazy river, water slide, fitness center, game room, sports courts, on-site dining options, and 24/7 gated security. Cable, internet, lawn care, and trash service are included for a low-maintenance ownership experience. Located approximately 10–12 miles from Magic Kingdom, this home provides quick access to Disney attractions, world-class golf, shopping, and dining. With its prime location, complete furnishing package, community amenities, and strong rental performance, 8952 Adriatico Lane represents exceptional value in one of Central Florida’s most sought-after vacation destinations. Schedule your showing today to experience all that this home and community offer.
Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)
Listing Agent: Hunter Albritton (863-287-1268)
2426 TANGIER DR, KISSIMMEE, FL 34747
$495,00018 Days on yellowkey MLS ID: O6419842
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $584 Tax: $7,169 (2025)Community: Windsor At Westside Ph 3Townhouse
Taxes:$7,169
Remarks: Welcome to this beautifully maintained, fully furnished 5-bedroom, 4.5-bath townhome with a private screened pool, located in the highly desirable Windsor at Westside Resort. Built in 2020, this spacious home features an open-concept layout, modern kitchen with solid surface countertops, generous living and dining areas, and a first-floor guest suite. Upstairs offers a spacious primary suite and additional guest bedrooms, making it ideal for large families and vacation guests. Currently operating as a successful short-term rental, this turnkey property presents an exceptional opportunity for investors seeking immediate rental potential or buyers looking for a vacation home in one of Central Florida's premier resort communities. This property may also be acquired as part of a unique turnkey short-term rental investment portfolio. The portfolio includes three established vacation rental properties with proven operational systems, established online presence, verified guest reviews, and documented historical performance. Additional portfolio information is available to qualified buyers upon request. Residents and guests enjoy world-class resort amenities including a 24-hour guard-gated entrance, resort-style pool, lazy river, clubhouse, fitness center, restaurant, sports courts, playground, and more. Conveniently located just minutes from Walt Disney World Resort, Margaritaville, Sunset Walk, championship golf courses, shopping, dining, and major highways. HOA includes cable TV, internet, security, common area maintenance, resort amenities, and professional association management. An outstanding opportunity to own a proven vacation rental property in one of the most sought-after resort communities near Disney.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: James Echeverria Perez (689-233-7774)
1844 GOBI DR, KISSIMMEE, FL 34747
$655,000121 Days on yellowkey MLS ID: O6389603
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2018Monthly Fee: $606 Tax: $10,121 (2025)Community: Windsor At Westside Ph 2ASpa: YesSingle Family
Taxes:$10,121
Remarks: Priced to sell! This fully furnished 6 bedroom, 4.5 bathroom vacation home is already operating and generating short term rental income, featuring three themed bedrooms, a loft with a large projector screen for movie nights, and a private outdoor retreat with a pool and spacious patio for entertaining with no rear neighbors, creating the perfect setup to attract bookings and memorable guest experiences. Inside, the home offers a spacious open concept layout that connects the living room, dining area, and kitchen, creating an ideal gathering space for families and large groups. The kitchen is fully equipped with stainless steel appliances, granite countertops, a tiled backsplash, and espresso cabinetry, making it both stylish and functional for extended stays. Ceramic tile flooring throughout the main living areas on the first floor provides durability and easy maintenance, ideal for vacation rental use. The first floor features a primary bedroom with direct access to the pool area and a private en suite bathroom complete with a soaking tub and walk in shower. The garage has been converted into a game room with a pool table and foosball table, providing an additional entertainment space that guests love. Upstairs you will find an additional en suite bedroom, four more beautifully furnished bedrooms, and two additional bathrooms. The loft area creates the perfect gathering space and is highlighted by a large projector screen, making it ideal for movie nights, game days, or relaxing after a day at the parks. Step outside to enjoy the covered patio and private pool area, perfect for entertaining or unwinding in the Florida sunshine. With no rear neighbors, the backyard offers added privacy rarely found in vacation homes. Located just minutes from Central Florida’s world famous attractions, shopping, and dining, owners and guests also enjoy access to resort style amenities including a clubhouse, fitness center, resort pool with lazy river, bar, and game room, all within the highly desirable Windsor at Westside Resort. Book your private showing today.
Listing is courtesy of: REAL BROKER, LLC (407-922-8986)
Listing Agent: Brian Hamaoui (407-760-0975)
8909 BENGAL CT, KISSIMMEE, FL 34747
$629,00082 Days on yellowkey MLS ID: S5148316
1 Days Off yellowkey (back on 6/24/2026)
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2019Monthly Fee: $607 Tax: $11,657 (2025)Community: Windsor At Westside Ph 2BSingle Family
Taxes:$11,657
Remarks: Back to the Market !!! Best priced fully furnished turnkey investment in Windsor at Westside Resort, one of the most sought-after short-term rental communities near Disney. This spacious 8 bedroom, 6 bathroom vacation home offers strong rental income potential and immediate operation. Features include open concept living area, two owner’s suites on first and second floors, dedicated game room, entertainment loft and private screened pool with spa, ideal for guest satisfaction and high occupancy. Resort amenities include clubhouse, lazy river, heated pool, fitness center, sports courts, restaurant and bar. Prime location near Disney parks, golf, shopping and dining.
Listing is courtesy of: BEKK HOMES LLC (407-342-8012)
Listing Agent: Carlos Selmo (407-342-8012)
2430 TANGIER DR, KISSIMMEE, FL 34747
$490,000809 Days on yellowkey MLS ID: O6199004
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $584 Tax: $7,376 (2023)Community: Windsor At Westside Ph 3Townhouse
Taxes:$7,376
Tax Year: 2023
Remarks: *** INCOME POTENTIAL *** VACATION HOME FULLY FURNISHED. In Excellent condition and beautifully decorated this 5 Bedroom Townhome with a splash pool has all you need for spending great moments in the Orlando Area or renting it out when not using it. It offers great income potential. Windsor at Westside is a vacation rental community with resort-style amenities featuring a fitness center, a mini market, a restaurant, and bar, a large community pool with a lazy river, a water playground, a playground, a soccer field, sports courts, and a sand volleyball court. 24-hour manned Gated security. Shows beautifully.
Listing is courtesy of: AMERICAN HORIZONS REALTY (407-466-0256)
Listing Agent: Martonio Pinto (407-466-0256)
1995 MAJORCA DR, KISSIMMEE, FL 34747
$37,500332 Days on yellowkey MLS ID: O6335963
REDUCED by $22,500 (37.5%) on 06/23/2026
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2263 Built: 2016Monthly Fee: $531 Tax: $8,075 (2024)Community: Windsor At Westside Ph 1Townhouse
Taxes:$8,075
Remarks: Fractional Ownership. Co-Ownership Opportunity in the highly sought-after Windsor at Westside Resort. Offered in 1/13th shares, this is a unique opportunity to enjoy all the benefits of a vacation home with the flexibility and efficiency of co-ownership. This fully furnished five bedroom, four and a half bathroom retreat comfortably accommodates up to 16 guests and is ideally located just minutes from Orlando’s world famous theme parks and attractions. The home blends modern design with resort style amenities, creating the perfect getaway for families and guests alike. On the main level, you will find a private king bedroom and full bathroom, ideal for multi generational stays. The open concept living space features a beautifully designed kitchen with granite countertops, stainless steel appliances, and a large island, all flowing seamlessly into a bright and inviting living room overlooking the private heated pool. Step outside to enjoy the covered lanai and convenient outdoor half bath, perfect for relaxing or entertaining. Upstairs, a spacious loft provides additional living space, along with four more bedrooms and three full bathrooms. Two themed bedrooms, inspired by Frozen and Star Wars, include custom murals and LED lighting for a fun and memorable experience. Contact the listing agent today for additional details.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Scott Cohara (407-398-9554)
2428 DUBAI ST, KISSIMMEE, FL 34747
$419,000691 Days on yellowkey MLS ID: O6233761
REDUCED by $21,000 (4.8%) on 06/11/2026
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $605 Tax: $7,376 (2023)Community: Windsor At Westside Ph 3Townhouse
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)
8815 MACAPA DR, KISSIMMEE, FL 34747
$689,000143 Days on yellowkey MLS ID: O6384144
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2017Monthly Fee: $607 Tax: $11,676 (2025)Community: Windsor At Westside Ph 2ASpa: YesSingle Family
Taxes:$11,676
Remarks: Enjoy breathtaking pond views and exceptional backyard privacy in this stunning 8-bedroom, 5.5-bathroom home located in the highly sought-after Windsor at Westside community. This fully furnished residence offers the perfect blend of luxury, comfort, and investment potential, ideal as a vacation retreat or a high-performing short-term rental. The spacious open-concept floor plan features expansive living and dining areas, a gourmet kitchen with granite countertops and stainless steel appliances, and two master suites—one conveniently located on each floor for added flexibility. Step outside to your private screened-in pool and spa, where the wide-open pond view creates a peaceful and relaxing setting with no rear neighbors. Inside, the home is tastefully designed with stylish furnishings and quality finishes, creating an inviting space that appeals to a wide range of vacation guests. 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 pad, fitness center, arcade, sports courts, playground, and more. The HOA conveniently includes cable, internet, lawn care, and valet trash service. Perfectly located just minutes from Disney, shopping, dining, and major highways, this turn-key property is truly move-in or rental ready — a rare opportunity you don’t want to miss!
Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)
Listing Agent: Veronica Li (407-674-0460)
2108 MOROCCO WAY, KISSIMMEE, FL 34747
$589,900100 Days on yellowkey MLS ID: S5147141
REDUCED by $5,000 (0.8%) on 05/15/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2017Monthly Fee: $563 Tax: $10,059 (2025)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$10,059
Remarks: Ideally located in the main section of the highly sought-after Windsor at Westside, just a short distance from the community’s premier entertainment complex and resort amenities. This exceptional pool home presents an outstanding opportunity as a luxury vacation rental, personal retreat, or high-performing investment property. If you are looking for a completely turnkey property, this is the home for you. In only its first year as an active Airbnb this home is already producing strong revenue numbers primarily due to its location and the tens of thousands spent on recent updates. This IS that extremely turnkey home you’ve been looking for. Projections look fantastic and are expected to continue increasing, this property offers immediate and growing income potential. Even better, all future bookings are transferable if the current management company is retained, allowing for a seamless transition and day-one revenue. Inside, the home showcases tens of thousands of dollars in upgrades and custom theming, designed to maximize guest appeal and long-term durability. Featuring all tile and luxury vinyl plank flooring throughout with absolutely no carpet, this home combines style with easy maintenance. The spacious open-concept floor plan flows beautifully from the main living and dining areas to the private screened lanai with pool and spa, creating the ideal space for entertaining and relaxation. The kitchen is fully upgraded with stainless steel appliances, granite countertops, and a large island with seating, while the first-floor primary suite offers privacy and convenience. Upstairs, a generous media and entertainment space provides the perfect setting for movie nights, gaming, and guest enjoyment. Additional bedrooms include a second primary suite, beautifully appointed guest rooms, and professionally themed bunk rooms that elevate the vacation rental experience. Residents and guests enjoy access to one of Central Florida’s premier resort communities, featuring a 5,000-square-foot clubhouse, resort-style pool, lazy river, water slide, fitness center, tennis, basketball, volleyball, soccer field, kids play area, arcade, on-site restaurant, tiki bar, and shop. The HOA covers landscaping, internet, cable, and daily trash service, making ownership easy and hassle-free. Conveniently located near Walt Disney World, shopping, dining, golf, major highways, and Orlando’s top attractions, this property checks every box for both lifestyle and investment performance. Schedule your private showing today and secure one of the strongest opportunities currently available in Windsor at Westside.
Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)
Listing Agent: Jim Mcquade (407-906-6508)
9047 RHODES ST, KISSIMMEE, FL 34747
$399,000128 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)
2414 DUBAI ST, KISSIMMEE, FL 34747
$428,00036 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)
2436 DUBAI ST, KISSIMMEE, FL 34747
$445,00025 Days on yellowkey MLS ID: O6417398
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $608 Tax: $6,789 (2025)Community: Windsor At Westside Ph 3 Pb 27 Pgs 158-162 Lot 101Townhouse
Taxes:$6,789
Remarks: Beautiful fully furnished townhouse located in the highly sought-after resort-style community of Windsor at Westside. This 2-story property features an open-concept floor plan, modern kitchen, and spacious living areas designed for comfort and entertainment. Perfect as a primary residence, vacation home, or short-term rental investment. The home offers excellent income potential and is fully equipped for immediate use. Windsor at Westside is a gated resort community offering world-class amenities including a clubhouse, resort-style pool, fitness center, tiki bar, and more. Conveniently located near Disney, major attractions, restaurants, and shopping.
Listing is courtesy of: DEBRASSI REALTY LLC (407-446-1343)
Listing Agent: Marcela Andrade Drummond (407-752-2323)
1974 MAJORCA DR, KISSIMMEE, FL 34747
$444,90029 Days on yellowkey 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.
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