Windsor Hills Ph 3 Single Family Homes For Sale in Kissimmee - 5 homes

Remarks: Absolutely stunning, turnkey 5-bedroom, 5-bath pool home located in the premier vacation rental community of Windsor Hills Resort—just 2 miles from Walt Disney World. This beautifully maintained home features an open-concept floor plan with immediate views of the private pool and hot tub from the entry, living, and dining areas—creating a bright, inviting space perfect for entertaining or relaxing. The spacious dine-in kitchen opens seamlessly to the main living area. The first floor offers two primary suites, an additional bedroom with adjacent full bath, and a large game room/arcade equipped with a pool table, pinball machine, bubble hockey, arcade games, darts, computer station, and an additional large TV—an ideal setup for guests and rental appeal. Upstairs, you’ll find two more generously sized bedrooms, each with its own en-suite bathroom featuring tub/shower combinations. Windsor Hills Resort is one of the most sought-after short-term rental communities in the area, offering world-class amenities including a movie theater, game room, convenience store, multiple playgrounds, tennis courts, basketball court, volleyball court, and more. Recent upgrades include: • All A/C systems replaced in 2025 & 2026 Ideal as a turnkey vacation rental, investment property, or primary residence.

Listing is courtesy of: GLORY INTL. REAL ESTATE CO (386-775-7778)

Listing Agent: Greg Roberts (321-305-2303)

Remarks: Welcome to this beautifully maintained 6-bedroom, 4-bathroom pool home located in the highly sought-after Windsor Hills Resort. Ideally located approximately 0.4 miles from the clubhouse, just a short walk away, and featuring no rear neighbors, this home offers exceptional privacy—an increasingly rare find in the community. Significant upgrades include a brand-new roof (2022), two new HVAC systems (2022), and luxury vinyl plank flooring throughout (2022). The private pool was professionally resurfaced in 2017, and the home underwent a full remodel the same year, ensuring modern comfort, style, and long-term durability. This property has been meticulously cared for and is ideal as a second home, or high-performing short-term rental investment. The main level features a bedroom with a full bathroom, perfect for guests or multi-generational living. Upstairs offers two spacious suites and three themed guest bedrooms. The garage has been converted into a fun game room, adding even more entertainment space. The HOA fee includes lawn service, irrigation maintenance, daily valet trash pickup, internet, and basic cable. Community amenities include 24/7 manned gated entry, a resort-style clubhouse, community pool, sports courts, and putting green. Located just minutes from Disney parks, major attractions, dining, shopping, championship golf courses, major airports, and Florida’s famous beaches, this is an exceptional opportunity to own a turn-key home in one of Central Florida’s most desirable resort communities.

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Veronica Li (407-674-0460)

Remarks: Under contract-accepting backup offers. Discover a rare gem in Windsor Hills: purposefully designed to generate income. This property has undergone extensive updates and capital improvements, with over $60,000 invested into the home since 2021. Major upgrades include a full roof replacement (2025), pool resurfacing with new mosaic installation (2024), and the addition of a Nirvana FC-140 Heat & Cool system (January 2026), allowing for both heating and cooling of the pool an added advantage for year-round bookings. Additional improvements include: bathroom updates, drain pump installation, drywall upgrades with smooth wall finishes in multiple rooms, staircase carpeting replacement with white risers, and washer and dryer replacement. Professionally managed and meticulously maintained as a short-term rental, the property benefits from a consistent booking history, with future reservations already in place offering immediate income potential for the next owner. Location is everything. Windsor Hills is one of Central Florida’s premier gated resort communities, located just 4 miles from Walt Disney World. Guests enjoy access to world-class amenities including a resort-style clubhouse, fitness center, tennis courts, playgrounds, and more driving strong, repeat demand year after year. Whether you’re seeking a turnkey vacation retreat, a second home, or a high-performing investment property, this opportunity checks every box. Schedule your private showing today.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Brandon Thompson (407-715-3513)

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: 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)