Windsor Hills Ph 3 Single Family Homes For Sale in Kissimmee - 6 homes

Remarks: This beautifully maintained 5-bedroom, 5-bath home in the 5-Star Windsor Hills Resort is an income-producing short-term vacation rental located just minutes from Walt Disney World. Highly sought after for its open floorplan, this property features the resort’s most desirable 5-bedroom layout, offering exceptional flow and comfort for large families and vacationing groups. The home immediately stands out thanks to extensive mechanical and interior upgrades, including a 2022 roof with 30-year architectural shingles, a 2023 saltwater pool system that is both low-cost and low-maintenance, a 2023 WiFi-controlled pool heater, a brand-new 2026 water heater with WiFi capability, new toilets added in 2026, and dual HVAC systems with major components replaced in 2016 and newer coils added within the last two years. Nest thermostats enhance efficiency, while upgraded bath vanities with solid-surface counters and wood-laminate hickory flooring in all bedrooms elevate the home’s interior appeal, durability, and rental desirability. For investors, the seller is willing to transfer any future bookings, allowing for immediate income continuity. Inside, the open main level features a spacious main dining area, a separate breakfast room, kitchen bar seating, granite countertops, stainless steel appliances, and a large living area ideal for gathering. Two first-floor ensuite bedrooms and an additional queen bedroom with adjacent bath provide convenient main-level living, while the second floor offers two Disney-themed junior suites, each with its own bathroom—an instant favorite among vacationing families. The converted garage game room with air hockey and pool tables adds to the home’s strong guest appeal. Outside, the screened lanai features a private heated saltwater pool and spa surrounded by privacy screening and a mature hedge, creating a secluded retreat perfect for relaxing after a day at the parks. Windsor Hills Resort remains one of Central Florida’s most desirable vacation rental communities, offering a clubhouse with lagoon-style pool, tennis courts, racquetball court, basketball court, marketplace, theater, game room, and fitness center, along with playgrounds, putting greens, and 24-hour guarded security. It is a prime vacation location due to its proximity to Disney, making this home an exceptional opportunity for buyers seeking a reliable, well-maintained, income-generating vacation property.

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

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

Remarks: Under contract-accepting backup offers. This Stunning, fully renovated, turnkey 6-bedroom, 4-bathroom pool home is located in the highly sought-after resort community of Windsor Hills. From the moment you enter, you're greeted by updated flooring that complements the open-concept layout and spacious interior. The bright and modern formal dining room flows seamlessly into a family room filled with natural light. The stylish kitchen features stainless steel appliances, and a charming breakfast nook, perfect for both entertaining and everyday living. Sliding glass doors open to your private outdoor oasis, complete with a sparkling pool, relaxing hot tub, and an extended covered lanai. In addition, the first floor also includes a convenient bedroom, while the second level offers five additional bedrooms, including two beautifully appointed en-suites. Windsor Hills is a premier, guard-gated community offering five-star amenities, including waterslides, a splash pad, resort-style pool and hot tub, sundry shop, movie theater, arcade, fitness center, playgrounds, and courts for tennis, volleyball, and basketball. Conveniently located approximately 1 mile from Hwy 192, this home provides quick access to great shopping, dining, I-4, and theme parks—making it the perfect primary residence, vacation home, or income-producing short-term rental.

Listing is courtesy of: ORLANDO REGIONAL PROPERTY MANAGEMENT (407-800-4545)

Listing Agent: Jeannette Lopez (407-800-4545)

Remarks: Welcome to this beautifully maintained 6-bedroom, 4-bathroom fully furnished home located in the highly sought-after Windsor Hills Resort in Kissimmee. Designed for comfort and convenience, this spacious property is ideal as a primary residence, vacation retreat, or income-producing short-term rental. Step inside to an open and inviting floor plan featuring generous living spaces perfect for gatherings. The home comes turn-key furnished, allowing for a seamless move-in or immediate rental potential. Guests of all ages will enjoy the dedicated game room, offering endless entertainment. Outdoors, unwind in your private screened pool, an ideal spot to relax after a day at the parks or soak up Florida sunshine in complete privacy. With six well-appointed bedrooms and four full bathrooms, there’s ample space for family and guests alike. Situated just minutes from world-class attractions, shopping, dining, and entertainment, Windsor Hills also offers resort-style amenities including a clubhouse, water park, fitness center, and more—all within a secure, gated community. This exceptional home truly offers the best of Florida resort living. Schedule your private showing today.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Paul Donovan (407-785-7070)

Remarks: Welcome to this beautifully updated beach-themed oasis, a fully renovated and furnished STR home located in the heart of Kissimmee. This property underwent a complete renovation in 2022, featuring a modernized kitchen with updated cabinetry, countertops, and appliances, along with new flooring and fresh interior paint throughout. Major capital improvements include a new roof (2022) and a recently resurfaced private pool (2025), offering peace of mind and long-term value. Designed for both comfort and functionality, each bedroom features its own dedicated full bathroom, providing privacy and convenience for guests—an setup for STR and multi-family use. The home also includes a converted garage game room equipped with ping pong, foosball, and arcade games, creating a fun and engaging entertainment space that enhances guest experience and rental appeal. The open-concept layout flows seamlessly to a screened-in lanai and private pool area, delivering the indoor-outdoor living experience for entertaining or relaxing after a day at nearby attractions. Located just minutes from Walt Disney World, shopping, dining, and major highways, this home is perfectly positioned for both strong STR income potential and long-term appreciation. The HOA provides exceptional value, including lawn service, irrigation maintenance, daily valet trash pickup, internet, basic cable, and a 24/7 manned guard gate for added security and convenience. Residents and guests enjoy access to a resort-style amenity package, including a large clubhouse, tropical community pool with water park slide and zero-entry access, open-air lounge, convenience store, fitness center, movie theater, billiards/game room, table tennis, lighted basketball and tennis courts, sand volleyball court, putting green, RV/boat parking area, and multiple playgrounds.

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Looking for a turnkey vacation home or investment property with future rental income potential? This beautifully maintained, fully furnished 6-bedroom, 4-bathroom pool home in the highly sought-after Windsor Hills Resort is ready for its next owner. This spacious residence offers 2,812 heated square feet and over 3,500 total square feet of living space. Professionally maintained and move-in ready, it presents an excellent opportunity for both vacation homeowners and investors seeking a proven short-term rental property. The thoughtfully designed floor plan features two primary suites, including a spacious owner's retreat upstairs with dual vanities, a soaking tub, separate shower, and private water closet. A second primary suite on the first floor offers added convenience for guests and multi-generational living. The open-concept living area is perfect for entertaining, featuring multiple gathering spaces, a formal dining room, breakfast nook, and a beautifully upgraded kitchen with stainless steel appliances and granite countertops. The family room opens directly to the outdoor living space, where you'll find a covered lanai, screened-in private pool, raised waterfall spa, and outdoor BBQ area—perfect for enjoying Florida's year-round sunshine. One of the home's most desirable features is the absence of carpet throughout. Instead, you'll find tile and luxury vinyl plank flooring, providing a modern look, easy maintenance, and added durability for vacation rental use. Located within the award-winning Windsor Hills Resort, residents and guests enjoy world-class amenities, including a 24-hour gated and guarded entrance, resort-style water park with lagoon pool, splash features and water slides, tennis courts, playgrounds, sports courts, fitness center, arcade and game rooms, and a 10,000-square-foot clubhouse complete with a state-of-the-art movie theater. Just minutes from Disney and Central Florida's top attractions, this property offers the perfect combination of location, lifestyle, and investment potential. Whether you're looking for a personal vacation retreat, a short-term rental investment, or both, this Windsor Hills gem is ready to deliver.

Listing is courtesy of: ALLIANCE REAL ESTATE GROUP (407-375-8680)

Listing Agent: Peter Dang (407-375-8680)

Remarks: Strong booking activity through the end of 2026!! Welcome to your ultimate vacation getaway—fully renovated in 2025 and featuring a brand-new roof (2025), all on a prime corner lot just 5 miles from Walt Disney World. This beautifully upgraded 5-bedroom pool and spa home is designed for comfort, fun, and strong short-term rental appeal, complete with an impressive converted garage game room for unforgettable guest experiences. Recent upgrades include two new water heaters (2025), exterior painting (2025) updated kitchen and all five bathroom vanities (2025), granite countertops in every bathroom, and new commercial-grade carpet installed in 2025, new furniture, and many more—making this home truly move-in ready. ACs were replaced in 2024 and 2022. Themed living takes center stage with 7 immersive themes throughout the home. The two primary suites feature How to Train Your Dragon and Avengers themes. The main-level bedroom is Star Wars, while the upstairs bedrooms are Toy Story and Mickey Mouse. Sleeping arrangements include 3 king beds and 4 twin beds. The garage is transformed into a Harry Potter–themed game room with foosball, air hockey, and a pool table, while the dining room brings the fun with a Super Nintendo World theme. Located in the highly sought-after, guard-gated Windsor Hills community, owners and guests enjoy top-tier resort amenities including a lagoon-style pool, water park with slides, fitness center, movie theater, arcade, bar, convenience store, playgrounds, and sports courts—all just minutes from Central Florida’s world-class attractions. Selller is a licensed real estate agent.

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

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