Location: Westside Ph 3, Kissimmee
Do Not Show Listings
8936 SYDNEY AVE, KISSIMMEE, FL 34747
$445,000128 Days on yellowkey MLS ID: O6374304
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2019Monthly Fee: $673 Tax: $5,571 (2025)Community: Windsor At Westside Ph 3Spa: NoTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,571
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Beautiful fully furnished vacation home located in the highly desirable Windsor at Westside Resort. This property offers an open floor plan, private screened pool and spa, and access to world-class community amenities including clubhouse, resort-style pool, fitness center, playground, and sports courts. Zoned for short-term rental, making it ideal for investors or as a second home. Conveniently located near major highways, shopping, dining, and Orlando’s top attractions. HOA includes cable, internet, lawn care, and resort amenities. Buyer to verify all information, including rental restrictions and HOA requirements.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Paula Maestrini (407-728-2666)
2402 DUBAI ST, KISSIMMEE, FL 34747
$460,000265 Days on yellowkey MLS ID: O6341750
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $673 Tax: $7,189 (2024)Community: Windsor At Westside Ph 3Spa: NoTownhouse
Taxes:$7,189
Tax Year: 2024
Remarks: This is Windsor at Westside, your new home far from home! This beautiful townhouse features an amazing living room facing the desired pool you crave to see after a day of all the parks fun! INVESTMENT, this is the name of the game, this house has still books to come, which means money in your pocket. Upstairs, you will find 4 bedrooms with decorations ready to go.
Listing is courtesy of: FABIANO DIAS REALTY LLC (689-241-6853)
Listing Agent: Fabiano Dias (689-241-6853)
2428 DUBAI ST, KISSIMMEE, FL 34747
$440,000646 Days on yellowkey MLS ID: O6233761
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)
8929 SYDNEY AVE, KISSIMMEE, FL 34747
$460,000223 Days on yellowkey MLS ID: O6353549
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2019Monthly Fee: $538 Tax: $7,070 (2024)Community: Windsor/Westside-Ph 3Townhouse
Taxes:$7,070
Elementary School: Westside K-8
High School: Celebration High
Remarks: ***We have bookings - great investment opportunity!!! This beautiful townhouse at 8929 Sydney Ave in Kissimmee, FL is ready for immediate occupancy and offers exceptional value in this desirable location. Situated in the heart of Kissimmee, you'll enjoy easy access to world-famous theme parks, shopping centers, restaurants, and major roadways. This impressive 2,263 square foot home features five spacious bedrooms and four and a half bathrooms, perfect for families of all sizes. The open floor plan creates a seamless flow throughout the main living areas, enhanced by soaring high ceilings that add to the sense of space and elegance. The kitchen showcases beautiful granite countertops and modern stainless steel appliances, making meal preparation a pleasure. Hard flooring extends throughout the main living areas, while the bedrooms feature comfortable carpeting. Ceiling fans are installed throughout the home for year-round comfort. The second floor includes a versatile loft area that can serve as a home office, playroom, or additional entertainment space. Step outside to your private oasis featuring a screened-in back porch overlooking a sparkling pool – perfect for Florida's sunny climate. The welcoming front porch adds charm and curb appeal. This move-in ready townhouse combines comfort, style, and convenience in one of Central Florida's most sought-after areas. With theme parks, shopping, dining, and major highways just minutes away, you'll have everything you need within easy reach. Don't miss this opportunity to own a piece of the Florida lifestyle in this well-appointed home.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Jessica Otero, Pa (407-780-1663)
8944 SYDNEY AVE, KISSIMMEE, FL 34747
$439,900381 Days on yellowkey MLS ID: O6306929
REDUCED by $5,000 (1.1%) on 05/19/2026
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2019Monthly Fee: $538 Tax: $5,645 (2025)Community: Windsor/Westside-Ph 3Spa: NoTownhouse
Taxes:$5,645
Remarks: Step into this stunning and beautifully furnished 5-bedroom, 4-bathroom townhome nestled within an exclusive resort-style community. Designed with comfort and style in mind, this spacious home offers a modern layout perfect for families. Enjoy your own private pool, ideal for relaxing afternoons or entertaining in the Florida sun. The community itself is rich with amenities, including clubhouse access, fitness facilities, resort-style pools, sports courts, playgrounds, and more—ensuring there’s something for everyone to enjoy. Don't miss out on this great opportunitiy! Tour this amazing property today!
Listing is courtesy of: GOLDEN KEY REAL ESTATE SOLUTIONS LLC (407-801-8283)
Listing Agent: Gleyson Silva (407-575-7332)
2410 TANGIER DR, KISSIMMEE, FL 34747
$428,00026 Days on yellowkey MLS ID: A4692263
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $584 Tax: $7,083 (2025)Community: Windsor At Westside Ph 3Townhouse
Taxes:$7,083
Remarks: Located in the highly sought-after resort-style community of Windsor at Westside, this beautifully maintained and fully furnished 5-bedroom, 4-bathroom townhome offers comfort, functionality, and excellent flexibility for both personal use and investment. The home features an open-concept floor plan with a spacious living and dining area, ideal for entertaining. The kitchen is equipped with modern appliances and ample cabinetry. One bedroom is conveniently located on the first floor, while the remaining bedrooms are upstairs, providing privacy and space for family or guests. Step outside to your private screened-in splash pool, perfect for relaxing after a day in the Orlando area. The property is tastefully decorated and move-in ready, making it suitable as a primary residence, second home, or short-term rental (buyer to verify rental restrictions). Windsor at Westside offers resort-style amenities, including a clubhouse, fitness center, community pool with lazy river, water playground, sports courts, playground, restaurant, and 24-hour gated security. Conveniently located near major highways, shopping, dining, and world-renowned attractions.
Listing is courtesy of: FLORIDA MORNING REALTY LLC (941-441-5990)
Listing Agent: Bin Cao (407-865-0588)
2412 TANGER DR, KISSIMMEE, FL 34747
$418,000100 Days on yellowkey MLS ID: G5108377
0 Days Off yellowkey (back on 4/27/2026)
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $538 Tax: $7,071 (2025)Community: Windsor At Westside Ph 3Townhouse
Taxes:$7,071
Remarks: Under contract-accepting backup offers. Price to sell!!Excellent Condition! Top-Performing Short-Term Rental!!! This fully furnished 5-bedroom, 4.5-bathroom townhome is located in the highly sought-after guard-gated Windsor at Westside Resort, just minutes from Walt Disney World, and offers a true turnkey investment opportunity with all future reservations transferring to the new owner for immediate income from day one. Featuring over 2,000 square feet of bright, open living space, the home showcases a modern kitchen with granite countertops, stainless steel appliances, premium cabinetry, and a large island that flows seamlessly into the spacious living and dining areas, all leading to a private screened-in pool perfect for relaxing after a day at the parks. Upstairs includes a generous loft and four additional bedrooms, including multiple en-suites, providing comfort and privacy for larger groups, while the resort-style amenities—such as a lagoon-style pool, lazy river, waterslide, splash zone, fitness center, arcade, sports courts, on-site restaurant and bar—create strong year-round rental demand. HOA services cover lawn care, internet, daily trash service, and 24-hour security, offering low-maintenance ownership, and with close proximity to Margaritaville Resort Orlando, Sunset Walk, US-192, and I-4, this property delivers the perfect blend of location, lifestyle, and proven investment performance. Don’t miss your chance to own a slice of paradise—schedule your private showing today and experience the resort lifestyle for yourself!
Listing is courtesy of: MOBED REALTY, P.A. (352-223-4884)
Listing Agent: Yuanyuan Li (407-883-2819)
2411 DUBAI ST, KISSIMMEE, FL 34747
$415,00047 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
Taxes:$6,787
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)
2422 DUBAI ST, KISSIMMEE, FL 34747
$449,990314 Days on yellowkey MLS ID: O6328333
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $608 Tax: $6,643 (2024)Community: Windsor At Westside Ph 3Townhouse
Taxes:$6,643
Remarks: This stunning retreat 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, 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 quartz 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. 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. 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. Schedule a showing today and take the first step toward making this dream retreat yours.
Listing is courtesy of: AUTHENTIC REAL ESTATE TEAM (407-440-1010)
Listing Agent: Karla Cintra (407-881-7730)
2407 DUBAI ST, KISSIMMEE, FL 34747
$450,00045 Days on yellowkey MLS ID: O6398836
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Monthly Fee: $560 Tax: $6,816 (2025)Community: Windsor/Westside-Ph 3Townhouse
Taxes:$6,816
Remarks: This beautifully furnished 5-bedroom, 4.5-bath townhouse offers an exceptional investment opportunity just minutes from Walt Disney World. Located in the highly desirable Windsor at Westside Resort—one of Orlando’s premier short-term rental communities—this home is designed to impress guests and maximize rental income. The property features a professionally curated furniture package, high-end décor, and luxurious finishes throughout. The fully equipped chef’s kitchen opens to a spacious dining area and comfortable family room, creating an ideal layout for entertaining and hosting large groups. With generous bedroom suites and stylish living spaces, this home delivers both comfort and convenience for vacationers. Windsor at Westside provides world-class resort amenities, including an impressive clubhouse with guest check-in, a fitness center, resort-style pool with lazy river, splash zone, indoor/outdoor restaurant and bar, outdoor firepit, sports courts, and a playground. The community’s strong reputation and extensive amenities make it a top choice for visitors seeking a high-quality vacation experience. Whether you’re looking for a personal getaway or a high-performing short-term rental, this property offers the perfect blend of luxury, location, and income potential in one of Central Florida’s most sought-after resort communities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Eugene Phillip (407-900-6095)
8919 SYDNEY AVE, KISSIMMEE, FL 34747
$470,000143 Days on yellowkey MLS ID: O6370850
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2019Community: Windsor/Westside-Ph 3Townhouse
Taxes:
Tax Year:
Remarks: Welcome to this beautiful 5Bed/4.5 Bath fully furnished short term rental vacation home in Windsor At Westside. This townhouse features open kitchen with granite countertop, 42 in cabinetry, and stainless steel appliances, spacious living spaces, and private swimming pool. The Windsor at Westside Resort provides massive amenities, including 8,000 square feet resort-style clubhouse, resort-style heated pool and spa, wireless internet on the pool deck, lazy river, recreation center, poolside cabana, playground, volleyball, tennis, basketball, game room, restaurant, bar, relaxing lounge area with indoor/outdoor fireplace, TVs and much more... This community is also in close proximity from Disney World and other attractions, like Universal Studios, Sea World, Golf courses, and Shopping Centers. Schedule a private showing today...
Listing is courtesy of: KN PREMIER REALTY, INC (407-668-8888)
Listing Agent: Guanhua Zhang (407-668-8888)
2430 TANGIER DR, KISSIMMEE, FL 34747
$490,000764 Days on yellowkey MLS ID: O6199004
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2020Community: Windsor At Westside Ph 3Townhouse
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)
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