Windsor Hills Condos For Sale in Kissimmee - 21 condos

Remarks: Unlock the Magic—A Standout Investment Opportunity Near Walt Disney World. FULLY FURNISHED and turnkey, this 3-bedroom, 2-bathroom top-floor corner unit is located in Windsor Hills Resort, nestled in one of Orlando’s most sought-after gated communities. Offering 1,450 SQ FT of bright, open living space, this exceptional TOP-FLOOR CORNER UNIT features the largest and most desirable floor plan in the community, positioned in a premier location within Windsor Hills. Just minutes from Walt Disney World, this vacation-ready property delivers both elevated living and INCOME POTENTIAL. Whether you're building your investment portfolio, enjoying a seasonal retreat, or creating unforgettable family moments, this residence delivers an exceptional experience. INSIDE THE UNIT. Fully furnished and thoughtfully designed—just bring your suitcase. The spacious open-concept layout is filled with natural light, creating an inviting and comfortable atmosphere. The private primary suite includes an en-suite bath and walk-in closet, while the split floor plan offers added privacy for guests. Strong rental history with proven performance—ready to generate income from day one. ZONED FOR SHORT-TERM RENTALS and currently operating as a successful vacation property, boasting a 4.95-STAR RATING across 171 reviews. BUILDING & COMMUNITY FEATURES. Located in the desirable Ventura building with ELEVATOR ACCESS to every floor, offering convenience for all. Ample parking available, including oversized and RV-friendly options. RESORT-STYLE AMENITIES. Enjoy a lagoon-style pool with water slides and splash pad, a modern clubhouse with fitness center and game room, plus tennis, volleyball, and basketball courts. Additional features include a putting green, playground, and picnic areas. Guard-gated with 24/7 security for peace of mind. The HOA provides exceptional value, covering 24-hour security, cable TV, internet, water, trash service, and exterior pest control. PRIME LOCATION. Unmatched location just minutes from Walt Disney World, Sunset Walk, Margaritaville, and top attractions like Fun Spot America and Old Town—placing entertainment, dining, and adventure right at your doorstep. Easy access to I-4, US-192, and SR-429.Whether you're seeking income, lifestyle, or both—this is a rare opportunity in Windsor Hills. Schedule your private tour today. Visit our 3D TOUR.

Listing is courtesy of: RE/MAX COLLECTIVE (813-438-7841)

Listing Agent: Martha Loss (813-421-0042)

Remarks: CALENDAR BLOCKED AND READY TO SHOW. Make this your full time residence, vacation property or income stream with AIRbnb and VRBO! Experience spectacular Disney fireworks from your own private balcony at this charming two-bedroom, two-bathroom condo in Kissimmee. This updated unit features an open floor plan that makes entertaining a breeze, complete with elegant stone countertops, rich wood cabinets, and sleek stainless steel appliances that would make any chef smile. Both bedrooms are thoughtfully themed and move-in ready, making this property perfect for generating rental income or creating magical vacation memories. The primary bedroom and second bedroom comfortable retreats after busy days exploring Central Florida's attractions. The community amenities are truly impressive and provide endless entertainment options. Take a splash at the on-site waterpark, relax by the sparkling pool, or treat yourself to a meal at the community restaurant. When you need to unwind, the spa services offer the perfect escape. Stay active with tennis and basketball courts, ensuring there's something for everyone to enjoy. Location couldn't be more convenient, with theme parks just minutes away and shopping centers nearby for all your needs. Island H2O water park is practically next door, adding even more aquatic fun to your Florida lifestyle. Target Grocery is also conveniently located for easy shopping trips. Whether you're looking for a profitable investment property or a personal vacation retreat, this condo offers the best of both worlds. The combination of stunning Disney views, modern updates, and resort-style amenities creates an opportunity that's hard to find. Don't miss your chance to own a piece of the magic in one of Florida's most desirable vacation destinations.

Listing is courtesy of: LUXE PROPERTIES LLC (305-809-7650)

Listing Agent: Deanna Meredith (407-331-6542)

Remarks: Welcome to this fully furnished and well decorated vacation home just minutes from Walt Disney World. Perfectly located near shopping, dining and everyday conveniences including Walmart and gas station, with easy access to I-4 for quick travel throughout Central Florida. Located in the highly sought-after Windsor Hills Resort, this gated community with 24/7 guard offers incredible resort-like amenities including a spectacular lagoon-style pool that feels like a beach, kids splash zone, exciting water slides, snack bar, arcade, and even a private movie theater for residents and guests to enjoy. This fully furnished and beautifully themed unit is move in and rental ready, making it perfect as a vacation home, short term rental investment, or second home near Disney. The building features elevators for convenient luggage transport, making arrivals and departures effortless. The community also benefits from an on-site HOA management, adding an extra layer of convenience for owners and guests. Major recent upgrades include a brand-new boiler and new A/C system installed in 2025 with a 10-year warranty, providing peace of mind and long-term value. Buyer to check all measurements, HOA fees and restrictions.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Lucia Souza (321-239-0287)

Remarks: Located in the popular gated community of Windsor Hills Resort, this condo offers resort-style living with access to fantastic amenities including a clubhouse with a movie theater and fitness center, a lagoon-style pool with water slides, sports courts, and scenic walking paths. The community is family-friendly and highly sought after for both residents and vacation rentals. Just minutes from Walt Disney World and close to Universal Studios and SeaWorld, the location provides easy access to Orlando’s top attractions. Nearby, you’ll find entertainment and shopping hubs like Old Town Kissimmee, The Loop outdoor mall, and charming Kissimmee Historic District. Outdoor lovers will enjoy nearby Kissimmee Lakefront Park and Lake Kissimmee State Park, perfect for relaxation and recreation. This blend of vibrant community amenities and proximity to world-class attractions makes it a great choice for living or investment.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Kay Bingham (407-207-2220)

Remarks: Welcome to 2778 Almaton Loop #203 – a beautifully updated 3-bedroom, 2-bathroom condo located in the sought-after gated community of Windsor Hills in Kissimmee. This turnkey property is an ideal investment opportunity with a strong rental history across major booking platforms. Inside, you'll find a newly renovated kitchen featuring sleek quartz countertops and modern finishes, seamlessly connected to a stylish, contemporary living area designed for relaxation and entertainment. Whether for personal use or vacation rentals, this condo offers a welcoming and memorable experience for guests. The unbeatable location puts you just minutes from Walt Disney World Resort, guaranteeing consistent guest demand year-round. In addition to the magic of Disney, you're close to a wide variety of dining options, and convenient shopping like Walmart and other nearby retail centers. Don’t miss out on this exceptional opportunity—schedule your magical showing today!

Listing is courtesy of: YELLOW ROCK REALTY CORP (407-421-8056)

Listing Agent: Marco Romero (407-450-9244)

Remarks: Step into a world of high-yield luxury and Disney-area magic with this premier top-floor, 3-bedroom, 2-bathroom sanctuary at the legendary Windsor Hills Resort! Fully furnished and reimagined at the start of 2026, this gem offers a turnkey experience for modern buyers. Standout features added this year include new quartz kitchen countertops, new appliances (stove & fridge), and new bathroom counters, vanity sinks, and faucets, complemented by newly resurfaced bathtubs, shower stalls, and surrounding tiles. The interior shines with luxury vinyl flooring in all bedrooms, new ceiling fans in the living room and master, and a complete furniture refresh featuring a new sofa, coffee table, and a 55" Samsung Smart TV in the living area. Each bedroom is optimized for comfort, from the master’s new desk and 50" Samsung TV to the second bedroom’s queen-size bed and the third bedroom’s new twin-over-double bunk bed. For the savvy investor, this property is a certified powerhouse, boasting a 2025 gross Airbnb income of $43,300. Managed with ease via a Schlage smart lock and Nest thermostat, the condo sits within a resort offering a lagoon-style pool, water park, fitness center, and cinema, all just minutes from Central Florida’s world-class attractions, dining, and shopping. Don’t just buy any property; own a proven, high-performance vacation home!

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: James Donovan (407-705-2616)

Remarks: The Seller is offering to cover 6 months of HOA dues paid at closing. Discover an exceptional opportunity to own a high-demand, income-generating property in the heart of Kissimmee. This fully furnished, ideally located condo at 7664 Comrow Street at 7664 Comrow Street, Unit #304 offers the perfect blend of comfort, convenience, and strong short-term rental potential. Positioned in a sought-after vacation corridor near major attractions, this property is perfect for investors looking to maximize returns or buyers seeking a personal getaway with income-producing benefits. Enjoy being approximately 10 to 15 minutes from Walt Disney World Resort, 20 to 25 minutes from Universal Orlando Resort, and 20 to 25 minutes from SeaWorld Orlando, making this property highly desirable for both vacationers and long-term residents. For outdoor and recreational fun, explore nearby golf courses, water parks, and nature trails. Indulge in a wide variety of dining options just 5 minutes away along US-192 Irlo Bronson Memorial Highway, offering everything from casual eateries to international cuisine. Shopping is convenient with Orlando Vineland Premium Outlets just 15 to 20 minutes away and The Loop approximately 20 minutes away, featuring top retail brands, entertainment, and dining. Water, cable TV, and internet are included in the condo fees, adding exceptional value and convenience for owners and guests alike. This is more than just a property; it is a strategic investment in one of Central Florida’s most desirable rental markets. With its unbeatable location, strong income potential, and year-round demand from visitors around the world, this condo stands out as a rare opportunity to own a piece of the thriving vacation market. Opportunities like this do not last, secure your investment and start generating income from day one.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Betsy Breton-Garcia, Pa (407-580-5350)

Remarks: CALENDAR BLOCKED AND READY TO SHOW. Make this your full time residence, vacation property or income stream with AIRbnb and VRBO! Great rental income! Discover this updated 2-bedroom, 2-bathroom condo located on the 4th floor in Windsor Hills. This unit features luxury vinyl flooring throughout and offers great views with no units above, ensuring a quieter living experience. The property is situated in the desirable Windsor Hills community, known for its excellent rental potential. This condo has a proven track record for short-term rentals including Airbnb and VRBO, making it an attractive investment opportunity. Location is a major highlight, with Walt Disney World nearby along with plenty of shopping and dining options. The Island H2O water park is just over a mile away, providing family-friendly entertainment. For daily necessities, Target Grocery is conveniently located about 3 miles from the property. The updated interior and prime location make this condo ideal for both personal use and rental income. The 4th-floor position provides elevated views while the luxury vinyl flooring adds a modern touch throughout the living spaces. Windsor Hills offers residents and guests access to community amenities in a well-maintained environment. The proximity to major attractions and everyday conveniences makes this location highly sought after by both buyers and renters.

Listing is courtesy of: LUXE PROPERTIES LLC (305-809-7650)

Listing Agent: Deanna Meredith (407-331-6542)

Remarks: Priced to sell! This beautifully maintained 3-bedroom, 2-bathroom top-floor condo is offered fully furnished and zoned for short-term rental, making it an ideal investment or personal getaway. Lovingly used as a family vacation home, it has no rental history and has been exceptionally well cared for. A brand-new AC system will be installed prior to closing for added peace of mind. NEW AC just installed!! Located in the highly sought-after, gated community of Windsor Hills, you’re just minutes from Walt Disney World and Universal Studios Florida. Windsor Hills offers a true resort-style experience with world-class amenities, including a lagoon-style pool, water park, movie theater, fitness center, game room, on-site convenience store, bar, and more. Schedule your private showing today—this one won’t last!

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Mike Chen, P.A (503-888-8070)

Remarks: Well-maintained 3-bedroom, 2-bath condo located in the desirable Windsor Hills Resort. This unit features an open-concept living and dining area with a functional layout and comfortable room sizes throughout. The kitchen offers ample cabinet space and flows into the main living area, ideal for everyday living or short-term rental use. The primary bedroom includes an en-suite bathroom, and the additional bedrooms are well-sized for family or guests. The unit includes in-unit laundry for convenience. Windsor Hills is a gated resort-style community offering amenities such as a lagoon-style pool, water park with slides, clubhouse, fitness center, tennis courts, and playgrounds. Located just minutes from major attractions, shopping, dining, and highways.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Geciane Centurion, Pa (321-525-1721)

Remarks: Welcome to Windsor Hills, one of Central Florida’s most sought-after resort communities just minutes from Walt Disney World. This fully furnished 3-bedroom, 2-bathroom condo offers well-designed living space and a rare ownership history, used only by the owners for 3 to 4 weeks per year and never rented out, giving the interior an exceptionally well-kept feel. Positioned just one block from the clubhouse and water park, the location offers one of the best balances in the community: close enough for an easy walk to the amenities, yet far enough to maintain quiet enjoyment inside the unit. Inside, the open-concept layout features a split-bedroom floor plan that creates privacy and comfort for both owners and guests. Natural light fills the main living area, while the upgraded kitchen offers quartz countertops, polished marble tile, stainless steel appliances, and generous prep space. The private primary suite includes an en-suite bath and walk-in closet. Two additional guest bedrooms provide flexible sleeping arrangements, including one queen bedroom and a trundle room that converts into two twin beds, ideal for family use or short-term guest stays. The second bathroom includes a tub and shower combination. Notable upgrades & updates that took place in 2026 include a new Rheem water heater with transferable warranty, new carpets in the bedrooms, new almond colored, engineered hardwood flooring, a fresh coat of interior paint and the AC system was replaced in 2023. The private balcony adds valuable outdoor living space and offers a comfortable setting for morning coffee or evening relaxation. Positioned on the third floor of an elevator-served building, this condo benefits from being above flood level and one floor below roof leak level as well. You’ll love the convenient parking and proximity to the community’s resort amenities - highlighted by a giant water park with three-story slides, an interactive splash zone, a lagoon-style zero-entry pool, hot tub, and tiki bar. Add in the 24-hour guard-gated security., fitness center, playground, 32-seat movie theater, putting green, arcade, convenience store, cybercafé, tennis, basketball, and volleyball courts, and you've got everything you need to enjoy your vacation within the same community your vacationing in. Oversized vehicle access and RV parking is also available. Windsor Hills remains one of the most recognized short-term rental communities, located approximately two miles away from Disney World, with convenient access to Universal Studios, SeaWorld, major airports, and highways US-192, I-4, SR-429. This community is zoned for short-term rentals, providing the opportunity for immediate cash flow, and the condo already comes with everything needed to rent it out after closing. Whether purchased as a vacation property, income-producing short-term rental, or hybrid personal-use property, this community delivers proven demand, and turnkey convenience in one package. Don't miss this rare opportunity to own a piece of paradise in one of the most coveted resort communities. Schedule your private showing today!

Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)

Listing Agent: Ferris Kassar (407-284-8384)

Remarks: Discover a rare opportunity in the highly sought-after Windsor Hills Resort: This open-palette, top-floor, end-unit condo offers exceptional privacy on all sides, with totally open sunset views not facing another building. Located just three miles from Disney World main gate, this two-bedroom, two-bath residence in building 5, is just a short 2 minute walk to the community lagoon-style pool, hot tub, dual water slides, and clubhouse following the shortcut sidewalk along the lake edge entry gate. This is a convenient location, yet provides a peaceful setting with no neighbors or noise from above plus the separation from the activity of the pool and clubhouse. Be sure to ask the listing agent for the virtual tour link to check out the home and its great location. A key advantage for buyers is the seller’s proactive approach to maintenance. A full home inspection was completed prior to listing and is available to the buyer. This provides added peace of mind and positions the home for a smooth, worry-free transition to its next owner. Step onto the screened lanai and take in uninterrupted vistas of the resort grounds. It is the perfect backdrop for morning coffee or evening drink / dinner relaxation, offering a true sense of openness and tranquility. Inside, the condo features a neutral aesthetic ready for your personal touch. The layout includes a fully equipped kitchen, a dining area with seating for six or more, and a comfortable living room designed for effortless vacation living or full-time enjoyment. The home is thoughtfully outfitted with conveniences that travelers and owners appreciate, including a full-size washer and dryer, ceiling fans, charging stations, and super high-speed fiber optic Wi-Fi ideal for remote work or streaming. The unit comfortably sleeps six with a king bed in the primary suite and queen and twin beds in the second bedroom or a roll away bed for additional separation privacy as desired. Additional highlights include durable and beautiful porcelain marble-style tile throughout all common areas, The community also offers pickleball, tennis, volleyball, and basketball courts, all just steps from your home away from home at this unit location. Two oversized elevators provide easy access, and the electronic keyless entry system with remote access ensures a seamless arrival experience. The condo has a strong rental history with proven guest appeal and is move-in ready with immediate occupancy available. Located in one of Central Florida’s premier gated vacation communities, this condo offers a blend of convenience and investment potential suitable for personal use, a family getaway, or a high-performance short-term rental. Be sure to check out the video tour for an in-depth look at the home and the short paths to the amenities.

Listing is courtesy of: IN TOUCH REAL ESTATE LLC (800-515-0321)

Listing Agent: Mark Breymeier (215-275-0487)

Remarks: Welcome to your dream vacation retreat or high-performing investment property at 2821 Almaton Loop, Unit 203. Just a few steps from the Club House and Pool area. This meticulously maintained 3-bedroom, 2-bathroom condo comes fully furnished with new HVAC system and new appliances, offering a seamless turnkey experience for those looking to enter the short-term rental market or secure a private getaway. Situated on the second floor, the home features a bright, open floor plan that flows effortlessly to a private screened balcony—the perfect spot to enjoy your morning coffee or evening cocktails in the Florida breeze. Located in the prestigious, 24-hour guard-gated Windsor Hills Resort, this property places you and your guests in the heart of the action, just minutes from Walt Disney World, premier dining, and world-class shopping. The resort itself is a destination, boasting a massive zero-entry heated lagoon pool, the Sir Windsor AquaVenture Water Park, a state-of-the-art fitness center, a 48-seat high-definition movie theater, and a lively games room. Residents also enjoy lighted tennis, basketball, and pickleball courts, sand volleyball, and a putting green. With its unbeatable proximity to Central Florida's top attractions and a robust suite of amenities, this condo represents a premier opportunity for discerning buyers seeking both luxury and location.

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: Dan Palmer (407-925-2432)

Remarks: This stunning turnkey short term rental is fully furnished, beautifully themed, and ready to enjoy from day one. Located in the highly sought after Windsor Hills Resort, this 3 bed, 2 bath first floor condo blends modern comfort with unbeatable convenience. The inviting open concept layout connects the kitchen, dining, and living areas, ideal for relaxing or entertaining. The fully renovated kitchen features soft close white cabinetry, 42” uppers with under cabinet lighting, granite countertops, stainless steel appliances, a stylish tile backsplash, and an expanded bar area. Both bathrooms have been updated with contemporary finishes, creating fresh, spa like spaces. Major improvements include a new A/C air handler and condenser (2025) and a new water heater (2022). Enjoy your private screened in patio overlooking lush green space and mature landscaping—a peaceful retreat after a day of adventure. Windsor Hills offers world class amenities including a resort style waterpark, playground, basketball, tennis, volleyball, fitness center, and onsite dining. With Target, Walmart, and abundant shopping and dining nearby—and Disney World just minutes away—this location is ideal for full time residents, vacation homeowners, and investors seeking a magical Central Florida experience.

Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)

Listing Agent: Greg Lowe (407-256-7035)

Remarks: Experience luxury living at its finest with this top-floor condo in the breathtaking Windsor Hills Resort, boasting the most spectacular view in the community! Recently transformed by its discerning owner, this unit features brand-new flooring, state-of-the-art appliances, and elegant quartz finishes—sparing no expense to elevate its allure. Tastefully furnished and thoughtfully themed, this meticulously maintained condo stands out in the short-term rental market, offering a seamless opportunity for its new owner.

Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)

Listing Agent: Michael Bouchard (407-443-1284)

Remarks: Under contract-accepting backup offers. ***TURNKEY & THEMED CONDO*** AC UNIT REPLACED IN 2024! Come see this TASTEFULLY FURNISHED & THEMED condo in beautiful WINDSOR HILLS RESORT! This condo has been renovated by the current owners to stand out in the short-term rental market and is ready to hit the ground running for the new owner! FULLY FURNISHED & meticulously maintained by the current owner this unit has had upgrades such as newer cabinets & touches of Star Wars themes throughout! This unit has already proven success in the short term rental market and even comes with plenty of bookings if the new owner stays with the current property management company! GROUND FLOOR and conveniently located in one of the closest buildings to the CLUBHOUSE & WATERPARK being just a 1 min walk away! WINDSOR HILLS is known as arguably the best short-term rental resort in the DISNEY CORRIDOR! Location is unbeatable being a short 5 min drive and 2 miles to DISNEY & close to other major attractions such as UNIVERSAL, SEA WORLD, & LEGOLAND. Bookings are practically effortless in this community!! Windsor hills is right around the corner from shopping & restaurants! The clubhouse is full of amenities such as the MOVIE THEATER, ARCADE, SUNDRY SHOP, FITNESS CENTER, WATERSLIDES, OVERSIZED HOT TUB, & OCCASIONAL LIVE MUSIC! The clubhouse is a great place to wrap up a family day at the parks with beautiful sunsets overlooking LAKE REEDY! WINDSOR HILLS is geared towards family fun and has PLAYGROUNDS scattered around the resort for the young ones! Windsor Hills also has a PUTTING GREEN, PLAYGROUNDS, TENNIS COURTS, BEACH VOLLEYBALL, BASKETBALL COURT, & RV PARKING as well! Start making family memories today that will last a lifetime! Schedule you’re showing today before it's too late!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Brandon Ramirez (407-489-0159)

Remarks: A beautiful 3-bedroom, 2-bathroom condo located in the highly sought-after gated community of Windsor Hills Resort in Kissimmee. This turnkey property is not only a fantastic vacation home but also a proven income-producing investment. This property has delivered consistent returns generating approximately $25,000 / year in profit. With a strong rental history and a Premier Listing on Vrbo / HomeAway, this condo is already positioned for continued success. Recent Upgrades: Brand New AC Unit (2025) ($7,900) All New Appliances (2024) ($2800)

Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)

Listing Agent: Douglas Addeo (561-251-3408)

Remarks: Windsor Hills Resort! One of best resort Minutes to Disney, Fully Furnished and updated 2bed 2bath, quiet, gorgeous and space, Located just a few steps to Clubhouse with the lagoon style pool, water park , slides and an array of world-class amenities…. airbnb short rentals with high return…..great opportunity for investment, vacation home or residence….

Listing is courtesy of: MAGICMIND REALTY LLC (407-399-7486)

Listing Agent: Huafeng Fang (407-399-7486)

Remarks: Windsor Hills Resort! One of best resort Minutes to Disney, Fully Furnished and updated 3bed 2bath, quiet, gorgeous and space, Located just a few steps to Clubhouse with the lagoon style pool, water park , slides and an array of world-class amenities…. airbnb short rentals with high return…..great opportunity for investment, vacation home or residence….

Listing is courtesy of: MAGICMIND REALTY LLC (407-399-7486)

Listing Agent: Huafeng Fang (407-399-7486)

Remarks: Windsor Hills Resort! One of best resort Minutes to Disney, Fully Furnished and updated 3bed 2bath, quiet, gorgeous and space, Located just a few steps to Clubhouse with the lagoon style pool, water park , slides and an array of world-class amenities…. airbnb short rentals with high return…..great opportunity for investment, vacation home or residence….

Listing is courtesy of: MAGICMIND REALTY LLC (407-399-7486)

Listing Agent: Huafeng Fang (407-399-7486)