Location: Windsor At Westside, Kissimmee
Do Not Show Listings
8839 GENEVE COURT, KISSIMMEE, FL 34747
$404,000130 Days on yellowkey MLS ID: TB8467307
REDUCED by $5,000 (1.2%) on 06/01/2026
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2102 Built: 2018Monthly Fee: $605 Tax: $7,587 (2025)Community: Windsor At WestsideSpa: YesTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,587
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Just minutes from Disney, this upgraded and fully furnished 4-bedroom, 3.5-bath townhome is the kind of property buyers and investors have been waiting for. Inside, you’ll find newer luxury vinyl flooring throughout, replacing all carpet for a fresh, modern, and easy-to-maintain living space. The home offers a private indoor pool for year-round enjoyment, plus a convenient half bath just outside the pool area, perfect for guests and entertaining. A spacious open loft adds valuable flexibility and can be used as a game room, second living area, or additional guest space. The layout includes a primary suite and Jack-and-Jill bedrooms, making it ideal for personal use, vacation stays, or short-term rental guests. Bright, stylish, and sold fully furnished, this property is ready for immediate enjoyment or rental income potential. Located in a desirable community with great amenities and only minutes from Disney, restaurants, shopping, and Orlando’s top attractions, this home offers location, function, and value all in one.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Sharon Wang (813-951-3122)
2022 MAJORCA DR, KISSIMMEE, FL 34747
$399,99059 Days on yellowkey MLS ID: O6396215
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2102 Built: 2015Monthly Fee: $665 Tax: $7,697 (2025)Community: Windsor At Westside Ph 1Spa: NoTownhouse
Taxes:$7,697
Remarks: Welcome to 2022 Majorca Drive, a highly desirable 4-bedroom, 3.5-bathroom townhome located in the Windsor at Westside Resort. Positioned in the preferred Phase 1 of the community, this home sits close to the clubhouse, resort-style lagoon pool, lazy river, bar & lounge, and a full range of premium amenities—an exceptional location that vacation guests consistently look for when booking their stay. Whether used as a personal getaway or an income-producing property, this townhome delivers the perfect combination of comfort, convenience, and resort-style living. Inside, the open-concept layout is ideal for entertaining, featuring a well-equipped kitchen with granite countertops, stainless steel appliances. A convenient outdoor half bathroom enhances the pool area—an extra feature that guests truly appreciate. Each bedroom is thoughtfully furnished to create a relaxing and welcoming atmosphere, making it ideal for vacation stays. Currently operating as a successful full-time short-term rental, the property is fully turnkey and ready to generate income immediately, or to be enjoyed as your own retreat near Orlando’s world-renowned attractions. Windsor at Westside is recognized as one of Central Florida’s premier resort communities. Residents and guests have access to a 10,000 sq. ft. clubhouse, a lagoon-style pool with lazy river and waterslide, fitness center, arcade, volleyball court, poolside Tu Casa bar & lounge, and 24-hour gated security. Ideally located just minutes from Walt Disney World, this property presents a rare opportunity to own one of the best-positioned townhomes in a highly desirable vacation community—offering strong rental potential, excellent guest appeal, and unmatched access to resort amenities. All information provided, including room measurements, is considered reliable but not guaranteed. Buyers and agents are advised to verify all details independently.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Alexandre Zapparoli Llc (321-444-8701)
8900 PRAGUE WAY, KISSIMMEE, FL 34747
$579,000312 Days on yellowkey MLS ID: O6329265
REDUCED by $11,000 (1.9%) on 05/20/2026
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $587 Tax: $9,677 (2024)Community: Windsor At Westside Ph 3Spa: YesSingle Family
Taxes:$9,677
Elementary School: Westside K-8
High School: Celebration High
Tax Year: 2024
Middle School: West Side
Remarks: Welcome to this stunning 7-bedroom, 5-bathroom pool home situated on a spacious corner lot in the highly sought-after Windsor at Westside Resort. Ideal for large families, multi-generational living, or short-term rental investment, this beautifully maintained home combines comfort, style, and resort-style amenities in a gated community just minutes from Disney and major attractions. The main floor features two generously sized bedrooms, including a primary suite with direct access to the private pool. Upstairs, you'll find five additional themed bedrooms—Harry Potter, Frozen, and Star Wars—plus a large loft that has been transformed into a movie room, perfect for family entertainment. Step outside to enjoy your own screened-in private pool and spa, complete with a child safety fence, offering the ideal setting for relaxation and fun. Residents and guests enjoy full access to world-class amenities, including a lazy river, splash pad, resort-style pools, tennis courts, fitness center, arcade, on-site restaurant, and a clubhouse—all secured with 24-hour gated entry. Conveniently located off US Hwy 192 and Toll Road 429, Windsor at Westside offers quick access to shopping, dining, and the “secret” west entrance to Disney via Western Way. Whether you're searching for a vacation retreat, or a high-performing investment property, this home is move-in ready and offers exceptional value in one of Central Florida’s premier resort communities. Don’t miss your opportunity to own a piece of the magic!
Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)
Listing Agent: Veronica Li (407-674-0460)
8926 ZURICH LN, KISSIMMEE, FL 34747
$485,900375 Days on yellowkey MLS ID: O6311534
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2492 Built: 2019Monthly Fee: $587 Tax: $7,737 (2024)Community: Windsor At Westside Ph 3ASingle Family
Taxes:$7,737
Elementary School: Westside Elem
Remarks: Your Dream Vacation Home—Just Minutes from Disney! Imagine owning a fully furnished 5-bedroom home in one of Kissimmee’s most sought-after resort communities—Windsor at Westside—just minutes from the magic of Disney and the excitement of US-192. Surrounded by restaurants, shops, theme parks, and unforgettable experiences, this could all be yours. The best of both worlds: Enjoy your vacation time with family whenever you want—no more worrying about reservations, availability, or high seasonal rates. Your home will always be ready to create unforgettable memories. And when you're not using it, it becomes a source of income. High returns on Airbnb: Windsor at Westside is a top choice for travelers who value comfort, security, and resort-style amenities. Properties like this offer excellent short-term rental returns, with consistent year-round occupancy thanks to its unbeatable location and full-service infrastructure. Property & community highlights: • 5 spacious bedrooms – perfect for large families or groups • Gated community with 24-hour security • Resort-style clubhouse with pool, lazy river, fitness center, bar, sports courts & more • Fully furnished and move-in ready • Professional vacation rental management available Invest in more than just a home—invest in lifestyle. This property isn’t just real estate. It’s a smart investment, a lifetime of memories, and a source of consistent income. Let’s talk! This might be the opportunity you and your family have been waiting for.
Listing Agent: Luciano Real Schroeder (321-304-1550)
8900 SYDNEY AVE, KISSIMMEE, FL 34747
$439,00038 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 white 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)
8908 PRAGUE WAY, KISSIMMEE, FL 34747
$529,000213 Days on yellowkey MLS ID: O6356954
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2019Monthly Fee: $563 Tax: $8,764 (2025)Community: Windsor At WestsideSpa: YesSingle Family
Taxes:$8,764
Remarks: Your Private Oasis Awaits at the fantastic Windsor at Westside Resort community. Step into luxury and leisure of this fully furnished 6-bedroom, 4.5-bathroom retreat nestled in one of Central Florida’s most sought-after vacation communities. Designed for comfort and entertainment, this spacious home features a stunning loft, soaring ceilings, and an open-concept layout that seamlessly blends elegance with functionality. It features a private heated south facing pool and spa for year-round relaxation, an expansive covered lanai with sun loungers and patio seating, a gourmet kitchen with stainless steel appliances and generous counter space and a breakfast bar, dual master suites, one on each floor making it ideal for guests or multi-generational living, a converted garage game room for added fun and entertainment, and stylish finishes throughout, including ceramic tile and plush carpeting. Recent upgrades include a brand-new AC compressor and brand-new dryer. The resort features lots of great amenities including a lazy river, splash pool, clubhouse bar, fitness center, and game room. The community is guard gated and the HOA includes cable, internet, and grounds maintenance. All this and just minutes from world-famous attractions, shopping, and dining, this property offers the perfect blend of convenience and escape. Whether you're seeking a second home, a vacation getaway, or a high-performing short-term rental, this residence delivers exceptional value and unforgettable experiences.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ping Ma (863-332-0298)
1864 NICE CT, KISSIMMEE, FL 34747
$695,90054 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 is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Matt Dixon (407-965-8906)
8894 QIN LOOP, KISSIMMEE, FL 34747
$585,000227 Days on yellowkey MLS ID: O6353019
1 Days Off yellowkey (back on 4/14/2026)
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $607 Tax: $11,608 (2024)Community: Windsor At Westside Ph 2ASpa: YesSingle Family
Taxes:$11,608
Remarks: Under contract-accepting backup offers. Located in Windsor at Westside – Just 15 Minutes from Disney! Welcome to this stunning 7-bedroom, 5.5-bathroom corner-lot home, perfectly designed for unforgettable family vacations and strong short-term rental performance. The spacious open-concept floor plan offers multiple living areas, a modern kitchen with granite countertops and stainless steel appliances, and a fun-filled game room—ideal for guests of all ages. Both floors feature a primary suite, providing flexibility and privacy for larger groups. Step outside to your private screened-in pool and spa with a covered lanai—perfect for enjoying Florida’s sunshine or shaded outdoor dining. The corner lot setting provides extra yard space and privacy, a rare bonus for owners and guests alike. Each bedroom is beautifully appointed, including custom-themed rooms inspired by Harry Potter, Mickey Mouse, and Star Wars, adding a unique charm that enhances guest experience and rental appeal. As part of Windsor at Westside resort, residents and guests enjoy world-class amenities including a grand clubhouse, resort pool with lazy river and splash zone, fitness center, arcade, and sports courts. The HOA covers lawn care, cable, internet, and valet trash service, ensuring a worry-free ownership experience. Whether you’re seeking a turn-key vacation retreat or a high-performing investment property, this home delivers the perfect blend of luxury, comfort, and convenience. Don’t miss your chance to own a piece of Central Florida’s vacation magic!
8901 RHODES ST, KISSIMMEE, FL 34747
$550,000349 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)
8825 CORCOVADO DR, KISSIMMEE, FL 34747
$669,90064 Days on yellowkey MLS ID: S5146750
REDUCED by $30,000 (4.3%) on 05/25/2026
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2018Monthly Fee: $563 Tax: $11,733 (2025)Community: Windsor At Westside Ph 2BSingle Family
Remarks: TURN-KEY INVESTMENT OPPORTUNITY! Sold furnished 8-BED LUXURY POOL HOME JUST MINUTES TO DISNEY! Welcome to your ultimate dream vacation home or high-performing short-term rental (Airbnb/VRBO) located in the highly sought-after Windsor community! Perfectly designed to accommodate large groups and multiple families to maximize your rental income. HOME FEATURES: Step inside to a modern, open-concept floor plan with high ceilings that seamlessly connects the fully-equipped chef's kitchen, dining area, and spacious family room. Head outside to your private, screened-in lanai where you will find a sparkling pool and a relaxing SPA—the absolute perfect backyard oasis to unwind after a long day at the theme parks. RESORT-STYLE AMENITIES: Located in a premier, secure gated community, you and your guests will have access to world-class resort amenities. Enjoy the massive luxury clubhouse, resort-style pool, lazy river, fitness center, playground, and more! It truly offers a 5-star resort lifestyle. UNBEATABLE LOCATION: Location is EVERYTHING! Situated in the prime 34747 zip code, you are just a short drive to Walt Disney World, world-class golf courses, and fantastic dining options on Hwy 192. Easy access to major highways and Orlando International Airport (MCO). Whether you are looking to expand your lucrative investment portfolio or seeking the perfect family getaway home, this property checks all the boxes. Properties of this size and in this prime location do not last long—act fast!
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: Mingke Li (352-973-2303)
8811 GENEVE CT, KISSIMMEE, FL 34747
$399,99961 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
$559,000150 Days on yellowkey MLS ID: O6369898
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
Remarks: 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)
8912 RHODES ST, KISSIMMEE, FL 34747
$520,00040 Days on yellowkey MLS ID: S5148044
5 Days Off yellowkey (back on 5/20/2026)
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)
8936 SYDNEY AVE, KISSIMMEE, FL 34747
$445,000132 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
Taxes:$5,571
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)
2108 MOROCCO WAY, KISSIMMEE, FL 34747
$589,90059 Days on yellowkey MLS ID: S5147141
0 Days Off yellowkey (back on 5/22/2026)
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: Under contract-accepting backup offers. 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)
1861 NICE CT, KISSIMMEE, FL 34747
$577,000183 Days on yellowkey MLS ID: O6363676
REDUCED by $3,000 (0.5%) on 05/22/2026
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3281 Built: 2018Monthly Fee: $563 Tax: $7,850 (2025)Community: Windsor At WestsideSingle Family
Taxes:$7,850
Remarks: Short Sale. Price Reduction! Turnkey 7-Bedroom Vacation Home in Windsor at Westside – Active Short-Term Rental! Welcome to 1861 Nice Court, a beautifully furnished and actively producing 7-bedroom, 5-bathroom short-term rental located in the sought-after Windsor at Westside Resort. With 3,281 sq ft of living space, this stunning home is designed to impress guests and maximize occupancy—making it the perfect investment property or vacation retreat near the magic of Disney. Step inside to a bright, open-concept layout featuring a spacious living area, modern kitchen with stainless steel appliances, and generous dining space ideal for large families and groups. This home offers multiple ensuite bedrooms and themed guest rooms that delight visitors of all ages and keep bookings strong year-round. The private screened-in pool and patio provide the perfect place to unwind after a day at the parks, offering your guests the relaxation and resort-style experience they’re searching for. Located in the gated, 24-hour resort community of Windsor at Westside, 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—making ownership truly hassle-free. Just minutes from Walt Disney World, Margaritaville, Sunset Walk, shopping, dining, and major attractions, this property offers strong rental history, excellent future booking potential, and a turnkey setup ready for its next owner. Whether you're looking to expand your STR portfolio or secure a high-performing vacation home, 1861 Nice Court is an exceptional opportunity in one of Central Florida’s premier resort communities.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Michael Steward (386-243-9585)
2402 DUBAI ST, KISSIMMEE, FL 34747
$460,000269 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
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)
1987 MAJORCA DR, KISSIMMEE, FL 34747
$416,99917 Days on yellowkey MLS ID: O6397361
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2263 Built: 2016Monthly Fee: $665 Tax: $7,682 (2025)Community: Windsor At Westside Ph 1Spa: NoTownhouse
Taxes:$7,682
Remarks: INCOME-PRODUCING OPPORTUNITY in Windsor at Westside, one of Kissimmee’s most sought-after short-term rental communities near Orlando’s world-famous theme parks. Unlike many investment properties in the area, this FULLY FURNISHED and TURNKEY 4-bedroom, 3.5-bath townhome has been primarily owner-used and exceptionally maintained, offering investors and second-home buyers a rare combination of rental potential and pride of ownership. Designed for both guest appeal and long-term durability, the home features a highly functional layout with a private first-floor king suite and full bathroom, ideal for multigenerational stays and vacation guests seeking convenience and privacy. The open-concept living space showcases a modern kitchen with granite countertops, stainless steel appliances, and an oversized island that seamlessly connects to the spacious family room overlooking the private pool area. The covered lanai, complete with a convenient half bath, creates an ideal indoor-outdoor entertainment setting highly desirable in the vacation rental market. Upstairs, a versatile loft provides additional gathering space, complemented by three well-appointed bedrooms and two full bathrooms. This unit offers a one car garage, heated private pool with a pool bathroom and a florida room, and is located within a walking distance from a resort style club house. Whether you are seeking a proven income-producing asset, a second home with rental flexibility, or a well-maintained investment property in a high-demand tourism market, this residence offers exceptional value, location, and long-term potential.
Listing is courtesy of: NOBSKA REAL ESTATE LLC (689-276-1593)
Listing Agent: Laura Teixeira, Pa (941-962-2413)
2428 DUBAI ST, KISSIMMEE, FL 34747
$440,000650 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)
8801 RHODES ST, KISSIMMEE, FL 34747
$610,000447 Days on yellowkey MLS ID: O6289038
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2016Monthly Fee: $584 Tax: $12,143 (2024)Community: Windsor At Westside Ph 1Single Family
Taxes:$12,143
Remarks: Back on the market due to the buyer’s financing falling through. Welcome to this beautiful vacation home located in the highly sought-after Windsor at Westside community. This stunning property has an open floor plan and features 8 spacious bedrooms and 6 bathrooms, offering ample space for families or groups. The home is perfectly situated with easy access to Disney World® theme parks via the nearby toll road 429, making it an ideal choice for those visiting the magical parks. Additionally, there are a variety of dining and shopping options just a short drive away. The Windsor at Westside community itself is a resort-style retreat, with an array of amenities that will enhance your vacation experience. The incredible 10,000 sq. ft. clubhouse is the perfect spot to relax and unwind, while the community’s lake and pier have serene views and outdoor activities. For ultimate relaxation and fun, enjoy the zero-entry resort-style pool, complete with a thrilling waterslide, lazy river, and a water playground. This home is not just a place to stay; it’s a destination in itself, offering both luxury and convenience. Don’t miss the opportunity to make this dream vacation home yours!
Listing is courtesy of: INTOP REALTY LLC (407-233-5453)
Listing Agent: Hanna Zhang (407-601-8668)
2462 DUBAI ST, KISSIMMEE, FL 34747
$499,000276 Days on yellowkey MLS ID: FC312189
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2492 Built: 2019Monthly Fee: $722 Tax: $8,214 (2024)Community: Windsor At Westside Ph 3ASpa: NoSingle Family
Taxes:$8,214
Remarks: Welcome to your dream vacation and stunning fully furnished 5 bedroom, 4 bathroom pool home located on a corner lot in the highly sought after Windsor at Westside Resort. Perfectly designed for indoor/outdoor entertaining and is excellent income producing short-term rental or a fantastic personal retreat. Designed with lots of space in mind this two story layout and open floor plan is the perfect getaway. The home sleeps up to 14 comfortably and features large living areas with plenty of space for relaxing. The first floor master bedroom offers privacy and space, the kitchen has granite countertops and stainless steel appliances with a nice island opening to the dining room and living space. Enjoy the gated resort style amenities with the zero entry point pool, water slide, lazy river, and water playground. It boasts a clubhouse, a lake with a pier, fitness center, volleyball courts, sundry shop and video arcade. This is an ideal location as it offers easy access to Disney World attractions and many other theme parks in the area. Welcoming any and all offers.
Listing is courtesy of: BEACHES WITHIN REACHES REALTY (386-864-3154)
Listing Agent: Abby Baker (386-864-3154)
1844 GOBI DR, KISSIMMEE, FL 34747
$655,00080 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)
1885 GOBI DR, KISSIMMEE, FL 34747
$765,000104 Days on yellowkey MLS ID: O6383464
REDUCED by $5,000 (0.6%) on 05/19/2026
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2016Monthly Fee: $607 Tax: $11,612 (2025)Community: Windsor/Westside, Windsor At WestsideSpa: YesSingle Family
Taxes:$11,612
Remarks: Welcome to the Epic Universe House! Experience a truly immersive vacation lifestyle in this stunning 8-bedroom, 6-bathroom pool home located in the gated community of Windsor at Westside. Fully themed, recently renovated, and professionally designed, this turn-key residence pays tribute to the highly anticipated Epic Universe, featuring an arcade, a Nintendo World gaming room, and immersive themed bedrooms including Harry Potter, How to Train Your Dragon, Legend of Zelda, and more! Spanning over 4,000 sq ft, this spacious retreat perfectly blends modern elegance with family entertainment. The open-concept first floor features ceramic tile flooring, a chef’s kitchen with granite countertops, and an oversized island designed for large gatherings. Step outside to your private outdoor oasis—a screened-in lanai with a sparkling pool and spa overlooking a serene water view. Recent Upgrades: This home is being sold AS-IS and Fully Furnished, featuring high-end furniture and professional decor. It is a proven, high-performing vacation rental with a history of top-tier reviews making it the perfect addition to any investment portfolio. World Class Resort Amenties: Living in Windsor at Westside provides 24/7 gated security and access to a 10,000 sq ft clubhouse including: Resort-Style Pool & Interactive Splash Park, Winding Lazy River & Water Slide, State-of-the-Art Fitness Center, Tu Casa Bar & Lounge / Poolside Tiki Bar, Arcade Game Room, Multi-purpose Sports Courts, & Sand Volleyball, Sundry Shop & Playground Unbeatable Location: Located just minutes from Walt Disney World, Universal Orlando Resort, and the newly opened Epic Universe park, you are at the heart of Central Florida’s top attractions, world-class dining, and premium shopping. Don't miss the chance to own a piece of the magic! Schedule your private showing today and step into a world of epic possibilities.
Listing is courtesy of: PABLA PROPERTIES (407-967-2757)
Listing Agent: Sunny Pabla (407-967-2757)
2100 ROME DR, KISSIMMEE, FL 34747
$720,000179 Days on yellowkey MLS ID: O6365123
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2015Monthly Fee: $665 Tax: $9,833 (2025)Community: Windsor At Westside Ph 1 Pb 23 Pg 112-118 Lot 100Spa: YesSingle Family
Taxes:$9,833
Remarks: Welcome to this exceptional 7-bedroom, 5-bathroom vacation home located in the highly desirable Windsor at Westside Resort. This fully furnished property is turn-key and revenue-ready, offering a spacious and well-designed floor plan ideal for large families and short-term rental guests. The home features an open-concept main living area, a generous upstairs loft, a 2-car garage, and a private screened-in pool with heated spa for year-round enjoyment. The kitchen offers stainless steel appliances, stone countertops, and a large island with seating, flowing seamlessly into the dining and living spaces. With ample bedrooms—including multiple suites—and thoughtfully designed themed rooms, this residence provides comfort and functionality for owners and guests alike. Located within one of Orlando’s top short-term rental communities, Windsor at Westside offers outstanding resort amenities such as a full-service clubhouse, resort-style pool with lazy river, fitness center, tennis and basketball courts, sand volleyball, arcade, restaurant, and 24-hour gated security. Just minutes from Disney and Central Florida’s world-class attractions, this property is an excellent opportunity for investors or buyers seeking a high-performing vacation retreat.
Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)
Listing Agent: Rubens Aranha (407-308-9094)
8906 ZURICH LN, KISSIMMEE, FL 34747
$559,00088 Days on yellowkey MLS ID: O6387866
2 Days Off yellowkey (back on 5/18/2026)
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2019Monthly Fee: $577 Tax: $8,739 (2025)Community: Windsor At Westside Ph 3ASingle Family
Taxes:$8,739
Remarks: Beautiful vacation home, fully furnished, ready to start your rental business. Kissimmee's most desirable resort communities. Near Disney parks, major roads, restaurants and shops. Clubhouse with resort-style pool, lazy river, gym, bar, sports courts & more. Property is actively used as a short-term rental. Future bookings may convey with the sale. Buyer must honor all existing reservations currently in place after closing. All bookings and rental agreements will be transferred to the new owner.
Listing is courtesy of: TALENT REALTY SOLUTIONS (407-910-2020)
Listing Agent: Andreza Machado (407-988-6639)
8849 RHODES ST, KISSIMMEE, FL 34747
$660,000320 Days on yellowkey MLS ID: O6327522
3 Days Off yellowkey (back on 5/18/2026)
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2015Monthly Fee: $563 Tax: $11,592 (2024)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$11,592
Remarks: Under contract-accepting backup offers. A phenomenal vacation rental investment opportunity with great income potential! Discover this prime lot in the vibrant Windsor at Westside, perfectly nestled across from the clubhouse with stunning lake view. This impeccably maintained vacation home is fully furnished with upgraded furniture, including three lavish primary suites and fun themed bedrooms, perfect for large vacation groups. The home boasts newly upgraded luxury vinyl flooring in all bedrooms (NO carpet), sleek granite counter tops in the kitchen and bathrooms, premium stainless steel appliances, and stylish tiles. Dive into relaxation with a private screened pool, paver deck, and covered lanai, backing to a natural pond and conservation area. Energy-smart features like two high-efficiency AC units, LOW-E dual-pane windows, and modern appliances keep it eco-friendly and cost-effective. This guard-gated community dazzles with a 10,000-square-foot resort-style clubhouse with arcade game room, a sparkling heated pool and spa, a meandering lazy river, a thrilling mini water park, a cutting-edge fitness center, a lively tiki bar, and all sorts of sports fields. Landscaping, internet, cable, and daily valet garbage collection are included in the HOA fee. Just minutes from Walt Disney World, premier golf courses, vibrant shopping, the airport, and major attractions, this is your chance to own a slice of paradise for investment or 2nd home! Schedule your exclusive private tour today!
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Sherry Wang (484-744-4586)
1614 LIMA AVE, KISSIMMEE, FL 34747
$639,900382 Days on yellowkey MLS ID: S5126817
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2019Monthly Fee: $564 Tax: $12,328 (2024)Community: Windsor At Westside Ph 2BSpa: YesSingle Family
Taxes:$12,328
Remarks: Spacious 8-bedroom, 6-bathroom single-family home located in the gated community Windsor at Westside Resort. This two-story home offers a functional layout with an open-concept living and dining area, as well as a well-appointed kitchen featuring granite countertops, stainless steel appliances, and a large island for additional workspace. The main floor includes two bedrooms—one of which is an en-suite with direct access to the pool area—along with an additional full bathroom for convenience.Upstairs, you’ll find a true standout feature: your very own cinema room, designed for movie nights and unforgettable moments. A spacious loft offers even more room to relax and enjoy, along with additional bedrooms including a second and a third en-suite and fun themed rooms. The exterior of the home includes a private pool and spa, covered lanai, and patio area with outdoor seating. The pool area provides ample space for relaxation and recreation. Fully furnished and turn key ready. 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)
1744 LIMA AVE, KISSIMMEE, FL 34747
$589,00018 Days on yellowkey MLS ID: O6407493
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2017Monthly Fee: $607 Tax: $10,366 (2025)Community: Windsor At Westside Ph 2ASingle Family
Taxes:$10,366
Remarks: Experience the ultimate Orlando getaway in this beautifully appointed 7-bedroom, 5.5-bath vacation home located in the highly desirable Windsor at Westside Resort, just minutes from Walt Disney World and Central Florida’s top attractions. Designed for comfort, relaxation, and entertaining, this spacious villa is ideal for large families, vacation groups, or short-term rental investment opportunities. The home features an inviting open-concept layout with generous living spaces on both levels, providing plenty of room for everyone to gather and unwind. The upstairs loft offers an additional entertainment area complete with a large TV, comfortable seating, and ample space for movie nights or game days. Step outside to your private west-facing screened lanai where you can enjoy sunny Florida afternoons by the sparkling pool and spa, lounge poolside, or relax under the covered patio while taking in peaceful views. The equipped kitchen includes a breakfast bar, abundant cabinetry, and things needed for meal preparation. Bedroom accommodations include: First-floor primary suite with king bed and private ensuite bath Additional half bath on the main floor Second-floor king suite with ensuite bath Second-floor queen suite with ensuite bath One queen bedroom Two bedrooms with twin beds One bunk room featuring a twin-over-full bunk bed Shared full bathrooms conveniently located between secondary bedrooms All bedrooms include TVs and generous storage space Residents and guests of Windsor at Westside enjoy access to outstanding resort-style amenities, including a lazy river, water slide, resort pool, tiki bar, clubhouse, fitness center, arcade, sports courts, and hot tubs. Conveniently located near Disney World, Universal Studios, SeaWorld, championship golf courses, shopping outlets, dining, and entertainment. Measurements are approximate and should be independently verified. Some furniture has been updated
Listing is courtesy of: CORNERSTONE INTERNATIONAL PROPERTY GROUP LLC (407-334-7497)
Listing Agent: Helen Lei (407-371-1225)
2427 DUBAI ST, KISSIMMEE, FL 34747
$444,000425 Days on yellowkey MLS ID: S5123971
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2265 Built: 2020Monthly Fee: $591 Tax: $7,228 (2024)Community: Windsor At WestsideTownhouse
Taxes:$7,228
Remarks: Dive headfirst into paradise at 2427 Dubai Street, Windsor At Westside! Forget ordinary – this is your resort, a dazzling, delivering a 6.9% Cap rate to the current owner is this fully furnished 5-bedroom, 4.5-bathroom end unit townhome where luxury meets pure, unadulterated fun. Imagine: sun-kissed mornings by your private, screened-in pool, the cool water shimmering like a sapphire. But hold on, the adventure's just beginning! Picture this: lazy river drifts, piña coladas at the tiki bar, adrenaline-pumping workouts in the cutting-edge gym, and legendary sports court showdowns. This isn't just a home; it's a launchpad to Orlando's magic, where theme park thrills, culinary explosions, and retail therapy await, just minutes away! Sensational financials available on request!
Listing is courtesy of: TEAM DONOVAN (407-705-2616)
Listing Agent: James Donovan (407-705-2616)
1876 NICE CT, KISSIMMEE, FL 34747
$679,90096 Days on yellowkey MLS ID: O6385119
0 Days Off yellowkey (back on 5/14/2026)
REDUCED by $19,100 (2.7%) on 04/15/2026
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: Under contract-accepting backup offers. Welcome to the ultimate Florida resort lifestyle! Positioned in the premier gated vacation community of Windsor at Westside Resort- this 8-bedroom, 6-bath lakeview home offers thoughtfully designed living space. This fully furnished, rental-ready home presents an outstanding opportunity for both savvy investors and families seeking a high-performing vacation property just minutes from Walt Disney World, dining, and premier shopping. Inside, the expansive open-concept design creates a seamless flow between the kitchen, dining, and main living areas — ideal for entertaining large groups. The oversized upstairs loft provides an additional gathering space perfect for movie nights, gaming, or relaxing after long days at the parks. Constructed in 2017, this residence embodies the Florida resort lifestyle. Step outside to your private heated pool and spa, perfectly positioned to capture sweeping lake views — one of the most sought-after settings within the community. Whether hosting guests or enjoying a quiet sunset, the outdoor space delivers both privacy and a true vacation atmosphere. Ownership includes access to Windsor at Westside’s impressive resort amenities, including a grand clubhouse, resort-style pool with lazy river and waterslide, tiki bar, fitness center, arcade, and more — enhancing both guest experience and rental appeal.Whether expanding your investment portfolio or securing a luxury vacation home, this property offers both lifestyle and income potential in one of Central Florida’s top-performing short-term rental communities. Sold fully furnished and rental-ready with future bookings conveying if you keep the rental company. Call for your showing today!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Katie Bray (407-779-6677)
8909 BENGAL CT, KISSIMMEE, FL 34747
$629,00041 Days on yellowkey MLS ID: S5148316
1 Days Off yellowkey (back on 4/27/2026)
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: 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)
1909 MAJORCA DR, KISSIMMEE, FL 34747
$445,00020 Days on yellowkey MLS ID: S5149758
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2263 Built: 2016Monthly Fee: $580 Tax: $7,423 (2025)Community: Windsor At WestsideTownhouse
Taxes:$7,423
Remarks: Discover the pinnacle of Florida living in this stunning, fully furnished 5-bedroom, 4.5-bathroom townhome, nestled within the highly sought-after Windsor at Westside resort community. Turnkey and professionally designed, this property is thoughtfully appointed to host large groups in style and comfort—an exceptional opportunity for investors seeking a high-performing short-term rental, or for buyers searching for the ultimate vacation retreat. A standout feature you won't find in most resort homes? Your own private garage—a rare and valuable bonus that offers added convenience, secure storage, and an extra layer of everyday practicality that sets this property apart from the competition. For out-of-state owners and short-term rental investors, this home delivers true peace of mind: a whole-home leak defense system actively monitors for water issues and helps prevent costly damage when you're miles away, while a brand-new washer and dryer mean one less major appliance to worry about replacing down the road. Even better, the home is just steps from the clubhouse, resort pool, and full lineup of community amenities—putting the very best of Windsor at Westside right at your doorstep. And when you're ready for quieter moments, step outside to your own private, screened-in pool—a tranquil escape where you can unwind in complete privacy after a day of adventure. As an owner at Windsor at Westside, you and your guests enjoy access to a world-class amenity collection, including a resort-style main pool with children's splash pad, relaxing hot tub, lazy river, fully equipped fitness center, arcade, kids' activity room, and basketball and volleyball courts. Ideally situated just minutes from Walt Disney World, Universal Studios, and SeaWorld, the home also places you near premier dining, championship golf, and upscale shopping at The Florida Mall and nearby outlet centers. Don't miss your chance to own a slice of paradise in one of Central Florida's most prestigious gated communities—where magical memories and smart investment go hand in hand.
2438 TANGER DR, KISSIMMEE, FL 34747
$588,000247 Days on yellowkey MLS ID: O6347903
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $587 Tax: $9,467 (2024)Community: Windsor At Westside Ph 3Single Family
Taxes:$9,467
Remarks: Don’t miss this amazing opportunity to buy this beautifully 7 bedroom 5 1/2 bathroom FULL FURNISHED POOL HOME in the most desirable resort, fully screened HEATED POOL & SPA, makes it perfect for indoor/outdoor entertaining. Windsor at Westside is gated resort community , one of the favorite desired resort style communities around Orlando and Kissimmee. This community has it all, clubhouse, lake & pier, zero-entry resortstyle pool complete with a waterslide, lazy river, and Kid's water playground, fitness center, volleyball courts, a sundry shop, and a video arcade. This is an ideal location it offers easy access to Disney World® attractions and many others theme parks in the areas. This home sleep up to 14 comfortably and features an open concept floor plan with a large living area. With plenty space spread out for entertaining and relax throughout entire house. The first floor Master Bedroom offers privacy and space, the kitchen has granite countertops and stainless steel appliances. Heated pool and spa to enjoy it at any time of the day. Don't miss this great opportunity
Listing is courtesy of: DOUBLE PINES REALTY, LLC (954-756-1835)
Listing Agent: Richard Lee (954-756-1835)
8956 ZURICH LN, KISSIMMEE, FL 34747
$575,00023 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)
2058 ROME DR, KISSIMMEE, FL 34747
$435,00096 Days on yellowkey MLS ID: O6385195
REDUCED by $15,000 (3.3%) on 05/09/2026
Bed: 5 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 2263 Built: 2015Monthly Fee: $580 Tax: $7,931 (2025)Community: Windsor At Westside Ph 1Spa: NoTownhouse
Taxes:$7,931
Remarks: Seller may consider buyer concessions if made in an offer ~ Welcome to opportunity in the GUARD GATED ~ RESORT COMMUNITY of Windsor at Westside – a FULLY FURNISHED ~ TURN KEY 5-bedroom, 4.5-bath PRIVATE POOL townhome that books well as a short-term rental and is ready to generate income from day one! Thoughtfully designed and tastefully decorated, this home feels light, bright, fresh, and truly move-in ready. TILE FLOORS flow throughout the main living areas, complemented by crown molding that elevates the OPEN CONCEPT living and dining spaces. The modern kitchen is both functional and stylish, featuring STAINLESS STEEL APPLIANCES, a tiled backsplash, ample cabinet and counter space, recessed lighting, pantry storage, and a large ISLAND with bar seating under pendant lighting – perfectly positioned to overlook the living and dining areas, making staying connected and entertaining effortless. A built-in drop zone at the foyer adds convenience for guests arriving and departing, while the covered front entry enhances curb appeal. The flexible floor plan includes a MAIN FLOOR BEDROOM & FULL BATH – ideal for multi-generational stays or guests who prefer first-floor accommodations. Upstairs, you will find the generous PRIMARY SUITE, a secondary en-suite bedroom with its own private bath, and additional well-appointed bedrooms and bathrooms designed with comfort and functionality in mind. Step outside to your COVERED PAVER LANAI and PRIVATE SCREENED POOL – a must-have for today’s vacation rental guests – complete with a convenient poolside half bath. Whether guests are soaking up the Florida sunshine poolside or floating the lazy river at the clubhouse, this property delivers the FULL RESORT EXPERIENCE. In addition to your private pool, Windsor at Westside offers a stunning community pool, clubhouse, fitness center, restaurant, game room, and one of the area’s most sought-after lazy rivers – amenities that consistently attract repeat bookings. The 1-car garage adds storage and owner convenience, while the LOW MAINTENANCE townhome lifestyle makes this an easy choice for investors or vacation home/second-home buyers alike. Located just minutes from world-famous theme parks, championship golf courses, premier shopping and dining, and with easy access to US-27 and 192, Windsor at Westside remains one of Kissimmee’s sought-after short-term rental communities. If you have been searching for a well-performing, fully furnished, income-producing vacation home in a true resort-style community – this is the one! Call today for more information and schedule a tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
1869 NICE CT, KISSIMMEE, FL 34747
$455,000104 Days on yellowkey MLS ID: O6383451
REDUCED by $4,000 (0.9%) on 05/09/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2492 Built: 2019Monthly Fee: $697 Tax: $8,805 (2025)Community: Windsor At Westside Ph 2ASingle Family
Taxes:$8,805
Remarks: Welcome to tastefully designed 5/bed 4/bath home with private pool facing conservation area in the prestige Community Windsor at Westside, zoned for short term vacation rental. The open floor plan seamlessly connects the living, dining, and kitchen areas, perfect for everyday living and entertaining. There is a master bedroom on the first floor and upstairs you’ll find another spacious master bedroom and additional bedrooms for privacy and comfort. Residents can enjoy world-class resort amenities, including an 8,000 sq. ft. clubhouse, heated pool, lazy river, spa, volleyball and basketball courts, and on-site restaurant and bar. The home is just minutes from Disney Parks and other Orlando attractions.
Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)
Listing Agent: Eileen Li (407-765-2589)
2410 TANGIER DR, KISSIMMEE, FL 34747
$428,00030 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)
8824 BENGAL CT, KISSIMMEE, FL 34747
$670,900227 Days on yellowkey MLS ID: O6353390
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
Taxes:$12,811
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)
1953 MAJORCA DR, KISSIMMEE, FL 34747
$370,000142 Days on yellowkey MLS ID: O6372789
REDUCED by $12,000 (3.1%) on 05/04/2026
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2102 Built: 2016Monthly Fee: $530 Tax: $7,751 (2025)Community: Windsor At Westside Ph 1Townhouse
Taxes:$7,751
Remarks: ***TENANT OCCUPIED*** Discover an exceptional opportunity with this beautiful 4-bedroom, 3.5-bathroom townhome, ideally located just minutes from the Walt Disney World Resort. This 2,102 sq. ft. property, built in 2016, is situated in the desirable, gated Windsor at Westside Community. The townhome includes a private pool and a one-car attached garage. The open floorplan features a kitchen/family room combo, high ceilings, tile and carpet flooring, walk-in closets, and an in-wall pest system. The HOA fees cover internet, cable, ground maintenance, pest control, trash disposal, and exterior maintenance, making it a low-maintenance option for owners. This property is an excellent option for short-term rental/vacation home use, with a minimum lease of just 1-7 days allowed, offering great potential for rental income. It can also be rented as a residencial long term. Residents and guests have access to Windsor at Westside's extensive, 8,000 sq. ft. clubhouse and amenity center, which includes: A resort-style heated pool and spa, Lazy river, Fitness center, Poolside cabanas, On-site store, restaurant, and bar, Sports courts (volleyball, tennis, basketball), Playground and game room. This home offers a perfect blend of a private retreat and resort-style living, with everything needed for a primary residence, second home, or profitable investment property.
Listing Agent: Danielle Marcondes Franca Viana Silva (407-668-0245)
8869 BENGAL CT, KISSIMMEE, FL 34747
$489,00027 Days on yellowkey MLS ID: O6404732
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2492 Built: 2019Monthly Fee: $607 Tax: $9,465 (2025)Community: Windsor At WestsideSpa: YesSingle Family
Taxes:$9,465
Remarks: CORNER LOT! Why wait for a new home to be built, when you can buy this fully furnished, turn-key VACATION HOME in the sought-after gated community of Windsor at Westside! Excellent Income Producing SHORT-TERM RENTAL Home. ONLY 10 MINS from Disney Gate! Fully furnished and professionally decorated two-story home with a private pool. This 5 bed/4 bath Winstone model features a spacious great room and kitchen with granite Island, allowing for ample seating and space to entertain. The sliding doors lead to your own private oasis with a covered, screened lanai with pool. One Guest Bedroom/Bath downstairs. Enjoy the myriad benefits of a resort-style community and have a blast! You'll have access to a fantastic clubhouse, a heated pool and spa, wireless internet on the pool deck, a lazy river, a state-of-the-art fitness center, a playground, a game room, and much more - all designed for families to relish for hours! The HOA takes care of landscaping maintenance, provides internet and cable services, and offers daily valet garbage disposal for your convenience. Located just a short distance from Highway 192, this charming short-term rental community provides easy access to major highways like I-4 and US-27. Plus, it's just a stone's throw away from theme parks, attractions, shopping malls, outlets, local restaurants, and grocery stores. Don't miss out on this fantastic opportunity to own a piece of the vacation rental market in the heart of Kissimmee!
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