Location: Windsor At Westside, Kissimmee
Do Not Show Listings
8832 MACAPA DR, KISSIMMEE, FL 34747
$699,000543 Days on yellowkey MLS ID: O6252445
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2016Monthly Fee: $607 Tax: $10,965 (2023)Community: Windsor At Westside Ph 2ASpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,965
Elementary School: Westside K-8
High School: Celebration High
Tax Year: 2023
Middle School: Horizon Middle
Remarks: Welcome to the best of Florida resort life! This 8 bedroom 6 bathroom house has all you can ask for and more! Fully furnished, this home is ready for an immediate occupancy, whether you're seeking an ideal AirBNB/Short-Term Rental or a personal vacation/ winter time residence. Airy and bright, the open-concept floor plan connects the living, dining, and kitchen areas, providing the perfect layout. The sliding doors in the family room area lead you directly to the pool patio area, creating a seamless indoor-outdoor living experience. An oversized heated pool with a jacuzzi and large patio space allows for cookouts, pool parties and watching the sunsets. The first-floor primary suite with a private bathroom and direct access to the lanai provides you a great personal space. An additional first-floor bedroom offers flexibility. Upstairs, there are six more spacious bedrooms and a loft space suitable for movie nights or a play area. Located in the luxurious community of Windsor at Westside, you'll have access to a variety of resort-style amenities, including a grand clubhouse, fitness center, lazy river, and more. Theme parks , beaches and shopping are just a short drive away, you'll have endless entertainment options at your fingertips. The HOA covers cable, internet, lawn care, trash, 24 hr security guard for a smooth and worry free life style. Make your appointment today! Equal Opportunity Housing.
Listing is courtesy of: LAWHUN ENTERPRISES IV, LLC DBA:FLORIDA REALTY INVESTMENTS IV (407-207-2220)
Listing Agent: Magdalena Danos, Pll (407-760-9286)
2108 MOROCCO WAY, KISSIMMEE, FL 34747
$614,90022 Days on yellowkey MLS ID: S5147141
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
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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)
1876 NICE CT, KISSIMMEE, FL 34747
$679,90059 Days on yellowkey MLS ID: O6385119
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: 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)
8810 MACAPA DR, KISSIMMEE, FL 34747
$599,000636 Days on yellowkey MLS ID: O6227461
1 Days Off yellowkey (back on 4/14/2026)
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2016Monthly Fee: $552 Tax: $8,296 (2023)Community: Windsor At Westside Ph 2Spa: YesSingle Family
Taxes:$8,296
Remarks: This gorgeous professionally decorated 8 Bedrooms/6 Bath single family home with private pool is located in is located in Windsor at Westside Resort one of the most famous resort communities in the Orlando/Kissimmee with easy access to the theme parks, dining and shopping. The home has fully furnished kitchen features upgrades such as stainless steel appliances, granite counter tops, and custom cabinetry. All furniture, decoration and appliances are included. The home can be used for vacation rental, winter home or long term residence. For vacation rental, this home has very beautiful booking history and financial income in the past a few years. Windsor at Westside Resort Amenities and Services include: - 10,000 sq.ft. Clubhouse with State of the Art Fitness Center - Resort style Pool with splash area - Lazy River. The club contains tu Casa Bar and Lounge - Market and Deli - Concierge - Sand Volley Court - Multi purpose court – Small soccer field - Playground.
Listing is courtesy of: ORLANDO REGIONAL PROPERTY MANAGEMENT (407-800-4545)
Listing Agent: Jason Ding (407-808-5589)
8894 QIN LOOP, KISSIMMEE, FL 34747
$585,000190 Days on yellowkey MLS ID: O6353019
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
Tax Year: 2024
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!
Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)
Listing Agent: Veronica Li (407-674-0460)
2121 MOROCCO WAY, KISSIMMEE, FL 34747
$600,000137 Days on yellowkey MLS ID: O6365732
1 Days Off yellowkey (back on 4/13/2026)
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3888 Built: 2016Monthly Fee: $552 Tax: $10,003 (2025)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$10,003
Middle School: Harmony Middle
Remarks: Under contract-accepting backup offers. **Seller may consider buyer concessions if made in an offer**Welcome to an extraordinary opportunity in the GUARD-GATED RESORT-STYLE community of Windsor at Westside—a beautifully maintained 6-bedroom, 4.5-bath retreat offering over 3,800 SQUARE FEET of luxurious living space. Built in 2016 and kept in immaculate condition, this FULLY FURNISHED HOME (negotiable) is perfect as a high-performing SHORT-TERM RENTAL or as an indulgent personal getaway near Orlando’s world-famous attractions. Step inside to an inviting OPEN-CONCEPT main floor, where the Kitchen, Dining, and Living spaces flow effortlessly together. The spacious Kitchen anchors the home with a functional layout, including an abundance of solid wood cabinets and STONE COUNTERTOPS, and a charming Dining area sits just off the Kitchen, offering a convenient and cozy spot for daily dining. Modern CERAMIC TILE FLOORS, bright natural light, and an ELEGANT ACCENT WALL in the Living Room create a warm, contemporary ambiance. Sliders open to the covered patio, leading you to your private outdoor oasis. The HEATED IN-GROUND POOL AND SPA, enclosed within a screened lanai, promise year-round enjoyment. With a remote-controlled pool heater, PAVER-STONE DECKING, and plenty of room for relaxing or dining al fresco, this is Florida living at its finest. The first floor features one of TWO PRIMARY SUITES, complete with a walk-in closet and a SPA-INSPIRED EN SUITE BATH offering dual sinks, a garden tub, step-in shower, and private water closet—an ideal retreat for owners or guests. A convenient half bath and a separate laundry room are also located on the main level. The garage has been transformed into a stylish air-conditioned MEDIA/GAME ROOM, adding tremendous entertainment value. Upstairs, a SPACIOUS LOFT provides an additional lounge or TV area—perfect for guests. You’ll also find the SECOND PRIMARY SUITE with en suite bath, plus FOUR MORE THEMED BEDROOMS and two additional full bathrooms, providing maximum comfort and flexibility for large groups. This property offers fully remote SMART HOME features, where everything from air conditioning, pool heat, and access can be controlled remotely! As part of the Windsor at Westside experience, enjoy access to an UNPARALLELED COLLECTION OF RESORT AMENITIES including a massive community pool, waterslide, lazy river, poolside cabanas, splash zone/water park, full-service clubhouse, fitness center, restaurant, bar, arcade, and sports courts. It’s a destination that feels like a vacation in itself. This PRIME LOCATION places you just minutes from Disney World, Margaritaville’s Sunset Walk, Island H2O Waterpark, the Promenade at Sunset Walk, golf courses, shopping, dining, and major highways including US-192, SR-429, US-27, and I-4—making every day or every guest stay exceptional. Whether you’re seeking a standout INCOME-PRODUCING PROPERTY or a LUXURIOUS RESORT ESCAPE for yourself, this Windsor at Westside home is truly a rare find. Schedule your tour Today!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
2401 LUXOR DR, KISSIMMEE, FL 34747
$680,00050 Days on yellowkey MLS ID: O6388392
0 Days Off yellowkey (back on 4/13/2026)
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2019Monthly Fee: $570 Tax: $9,864 (2025)Community: Windsor At Westside Ph 3ASingle Family
Taxes:$9,864
Remarks: Under contract-accepting backup offers. Don’t miss this amazing opportunity to buy this beautifully LAKEFRONT 8 bedroom 6 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)
2440 TANGIER DR, KISSIMMEE, FL 34747
$525,00086 Days on yellowkey MLS ID: O6378202
0 Days Off yellowkey (back on 3/3/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2492 Built: 2019Monthly Fee: $587 Tax: $7,877 (2024)Community: Windsor At WestsideSpa: NoSingle Family
Taxes:$7,877
Middle School: West Side
Remarks: Under contract-accepting backup offers. Located within the highly sought-after Windsor at Westside gated resort community, this fully furnished home offers flexibility as a primary residence, vacation getaway, or income-producing short-term rental. The property is already set up for Airbnb use and is being sold turnkey, allowing for immediate occupancy or continued rental operations. The home offers five bedrooms and four bathrooms, along with a game room and an open, airy floor plan designed for both comfort and functionality. The layout easily accommodates large groups, with multiple spaces to gather or unwind throughout the home. A private first-floor suite provides a quiet retreat, while the kitchen features modern finishes including granite counters and stainless steel appliances. Outdoors, a private pool to create the perfect place to relax at any time of day. Owners and guests enjoy access to a wide range of resort amenities, including a full-service clubhouse, lake and pier, expansive zero-entry pool, water slide, lazy river, splash area, fitness center, sports courts, arcade, and on-site convenience shop. Conveniently positioned near Disney and major attractions, this home combines location, lifestyle, and investment potential in one exceptional opportunity.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Caitlin De Oliveira (407-267-7196)
8811 MACAPA DR, KISSIMMEE, FL 34747
$740,00070 Days on yellowkey MLS ID: O6382041
Bed: 9 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4391 Built: 2017Monthly Fee: $563 Tax: $11,694 (2025)Community: Windsor At Westside Ph 2ASpa: YesSingle Family
Taxes:$11,694
Remarks: Beautiful 9-bedroom,6-bathroom water-front pool home in the highly sought-after Windsor at Westside resort community. Situated on a premium lot with stunning water view, this fully furnished property is perfect as a luxury vacation retreat or a high-performing short-term rental investment. The spacious open-concept layout offers expansive living and dining areas, a gourmet kitchen with granite countertops and stainless steel appliances, and two master suites, one on each floor. Enjoy the Florida lifestyle with your private screened-in pool and hot tub overlooking the pond. This home has been thoughtfully upgraded to enhance the guest experience, including newly installed: *Luxury vinyl plank flooring throughout (no carpet)*, all bedrooms are tastefully decorated with quality furnishings and stylish accents to appeal to a wide range of guests! Resort-style amenities include a 10,000 sq. ft. clubhouse, resort pool with lazy river and splash pad, fitness center, arcade, sports courts, playground, and more. HOA includes cable, internet, lawn care, and valet trash service. Conveniently located just minutes from Disney, shopping, dining, and major highways. This turn-key property is move-in or rental ready—an opportunity you don’t want to miss!
Listing is courtesy of: YOUR DREAM HOUSE REALTY (440-477-7276)
Listing Agent: Selina Li (440-477-7276)
2022 MAJORCA DR, KISSIMMEE, FL 34747
$399,99022 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 1Townhouse
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 (321-444-8701)
8811 GENEVE CT, KISSIMMEE, FL 34747
$410,00024 Days on yellowkey MLS ID: S5146973
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2018Monthly Fee: $579 Tax: $6,358 (2025)Community: Windsor At Westside Ph 2BTownhouse
Taxes:$6,358
Remarks: 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)
8900 PRAGUE WAY, KISSIMMEE, FL 34747
$590,000275 Days on yellowkey MLS ID: O6329265
Bed: 7 Bath: 5.5 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $587 Tax: $9,677 (2024)Community: Windsor At Westside Ph 3Single Family
Taxes:$9,677
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!
8916 SYDNEY AVE, KISSIMMEE, FL 34747
$479,000987 Days on yellowkey MLS ID: O6133760
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2265 Built: 2019Monthly Fee: $560 Tax: $6,111 (2022)Community: Windsor At WestsideTownhouse
Taxes:$6,111
Tax Year: 2022
Remarks: Welcome to this beautiful home located at the unique Windsor At Westside. This 5 bedrooms, 4 full bathrooms and 1 half bathroom features an open plan family room, kitchen and dining area with sliding patio doors in the first floor and also one bedroom. In the second floor you'll find the other bedrooms and a very nice loft area to gatter your guests, family and friends in a private and exclusive area of the home. Property also includes a private pool. This is the perfect home in the most popular resort community that features one of the most amazing Clubhouse Amenities in the area. Just minutes away from world-famous Disney World.
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Paulo Goncalves Ferreira (407-818-0717)
2014 MAJORCA DR, KISSIMMEE, FL 34747
$429,00027 Days on yellowkey MLS ID: S5146548
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 2263 Built: 2015Monthly Fee: $579 Tax: $7,931 (2025)Community: Windsor At WestsideTownhouse
Taxes:$7,931
Remarks: Welcome to this 5-bedroom, 4.5-bathroom townhome with private heated pool located in the highly desirable Windsor at Westside — a premier short-term rental community just minutes from major highways, shopping, dining, and Central Florida attractions. This property is a competitive option within the community, featuring a private heated pool and a garage that can be converted into a game room, both highly desirable features for short-term rental performance. The home offers a functional open-concept layout, connecting the living, dining, and kitchen areas. The kitchen includes stainless steel appliances, granite countertops, and ceramic flooring. 1 bedroom on the first floor 4 bedrooms upstairs Spacious loft area Owner’s suite with walk-in closet and private bath Second-floor laundry room Enjoy a private screened-in pool and courtyard, ideal for relaxation and guest use. Community amenities include a resort-style pool, lazy river, clubhouse, fitness center, sports courts, tiki bar, and spa. Zoned for short-term rental, making it suitable for investment and vacation use, or primary residence.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Ciro Noccioli Monteiro Alves (321-442-9680)
8825 CORCOVADO DR, KISSIMMEE, FL 34747
$699,90027 Days on yellowkey MLS ID: S5146750
Bed: 8 Bath: 6.0 Liv Area Sq Ft: 4041 Built: 2018Monthly Fee: $563 Tax: $11,733 (2025)Community: Windsor At Westside Ph 2BSingle Family
Taxes:$11,733
Remarks: TURN-KEY INVESTMENT OPPORTUNITY! 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)
1861 NICE CT, KISSIMMEE, FL 34747
$580,000146 Days on yellowkey MLS ID: O6363676
Bed: 7 Bath: 5.5 Liv Area Sq Ft: 3281 Built: 2018Monthly Fee: $563 Tax: $7,850 (2025)Community: Windsor At WestsideSingle Family
Taxes:$7,850
Remarks: Short Sale. LOWEST PRICED 7 BEDROOM! 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 Agent: Michael Steward (386-243-9585)
8824 BENGAL CT, KISSIMMEE, FL 34747
$670,900190 Days on yellowkey MLS ID: O6353390
1 Days Off yellowkey (back on 3/28/2026)
Bed: 8 Bath: 6.0 Liv Area Sq Ft: 4041 Built: 2019Monthly Fee: $550 Tax: $12,811 (2024)Community: Windsor At Westside Ph 2B-1Single Family
Taxes:$12,811
Remarks: 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)
8931 ZURICH LN, KISSIMMEE, FL 34747
$549,00029 Days on yellowkey MLS ID: O6393822
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2492 Built: 2020Monthly Fee: $721 Tax: $7,587 (2025)Community: Windsor At Westside Ph 3ASingle Family
Taxes:$7,587
Remarks: A fantastic choice to be your Vacation Rental Property in the Windsor at Westside, located in Kissimmee Florida! 5 Bedrooms - 4 Bathrooms and your own Private Pool. Welcoming you inside is an amazing open floor concept that combines your living, dining and kitchen areas into one space. Also downstairs you will have an ensuite for your convenience. Upstairs you will find the loft, master bedroom ensuite with a large closet, one more ensuite and two more themed bedrooms and one bathroom. Also the laundry room is conveniently located upstairs. Granite countertops, light color cabinets, stainless steel kitchen appliances, themed bedrooms and much more. This home features a heated, private pool, a covered Lanai and pool deck area. The Windsor at Westside is a resort community and features a large Community pool, Lazy river, splash pool, gym, restaurant and much more. This is a great vacation home, very close to other area attractions.
Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)
Listing Agent: Zhiming Xu (407-984-0087)
9013 RHODES ST, KISSIMMEE, FL 34747
$651,90064 Days on yellowkey MLS ID: O6381275
Bed: 6 Bath: 4.5 Liv Area Sq Ft: 3142 Built: 2018Community: Windsor At Westside Ph 1Single Family
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Remarks: Located in the exclusive gated community of Windsor at Westside, this beautiful two-story residence, sold fully furnished, is the perfect combination of comfort, sophistication, and excellent investment potential. With 6 bedrooms, 4 full bathrooms, and 1 powder room, the house features a modern open-concept layout, providing spacious, integrated, and well-lit environments. Upon entering, a charming veranda with a garden welcomes you and creates a cozy atmosphere. Inside, you'll find a spacious living room with ceiling fans, integrated with the dining room and kitchen, forming an ideal environment for both everyday life and entertaining guests. Sliding glass doors lead to the outdoor area, where the private pool and covered veranda are located—the perfect space for leisure and relaxation. The kitchen is fully equipped with appliances, wooden cabinets, and a breakfast bar, combining practicality and elegance. The master suite is located on the first floor, offering privacy, a large bathroom, and a walk-in closet. On the second floor are the other five bedrooms—all with closets and carpeting—as well as a spacious loft that can be used as a TV room, game room, or additional living space. The condominium offers a complete resort-style structure, with a clubhouse, swimming pool, gym, volleyball courts, playground, game room, and security, providing leisure and convenience for the whole family. The location is privileged: just 15 minutes from Walt Disney World, close to golf courses, outlets, restaurants, supermarkets, and with easy access to the region's main highways. It is also about 30 minutes from Orlando International Airport, facilitating travel for domestic and international trips. Whether for living or investing in vacation rentals, this is a unique opportunity in one of Florida's most desirable areas.
Listing Agent: Rosania Taylor (407-580-6137)
8888 BENGAL CT, KISSIMMEE, FL 34747
$629,900192 Days on yellowkey MLS ID: O6351668
2 Days Off yellowkey (back on 3/26/2026)
Bed: 8 Bath: 6.0 Liv Area Sq Ft: 4041 Built: 2019Community: Windsor At Westside Ph 2BSingle Family
Remarks: Under contract-accepting backup offers. Experience resort living at its finest in this exceptional 8-bedroom, 5.5-bathroom home located in the highly sought-after Windsor at Westside community. Situated on a premium conservation lot, this fully furnished residence is ideal as a luxury vacation retreat or a short-term rental investment. The spacious open-concept layout 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. Step outside to enjoy the Florida lifestyle with your private screened-in pool and spa, offering serene tree-lined conservation views. Inside, guests will love the two themed bedrooms inspired by Star Wars and Disney Princesses, while the remaining rooms are tastefully decorated with quality furnishings and stylish accents to appeal to a wide range of guests. Residents and guests have 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 covers cable, internet, lawn care, and valet trash service for ultimate convenience. Perfectly located just minutes from Disney, shopping, dining, and major highways, this turn-key property is move-in or rental ready—a rare opportunity you don’t want to miss!
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