Windsor Hills Real Estate - Search all Windsor Hills homes and townhouses for sale.

5 Beds ⋅ 5 Baths ⋅ Windsor Hills SubDv. ⋅ 34747 Zip Code

Professionally redesigned and offered fully furnished, this exceptional 5-bedroom, 5-bath pool home in the sought-after Windsor Hills Resort delivers the ultimate Central Florida vacation home experience just minutes from Walt Disney World. Thoughtfully designed for both comfort and entertainment, the home features two spacious primary suites on the first floor, three additional ensuite bedrooms, and accommodations ideal for large families and vacation groups. Guests of all ages will love the dedicated home theater, immersive Harry Potter and Minions-themed bedrooms, and private screened pool and spa, creating a memorable stay long after the parks close. The open-concept living area provides the perfect gathering space, while the well-appointed kitchen and generous dining areas make hosting effortless. Located within the guard-gated Windsor Hills Resort, owners and guests enjoy access to one of Orlando's premier vacation communities featuring a resort-style lagoon pool with water slides, splash park, clubhouse, fitness center, arcade, sports courts, playgrounds, and more. With its unbeatable location, impressive entertainment spaces, and proven appeal to vacationing families, this turnkey home is equally suited as a personal retreat, second home, or short-term rental investment.

7742 Comrow St, Kissimmee

$699,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code

Welcome to an exceptional opportunity in Windsor Hills Resort, one of Central Florida's premier vacation home communities just minutes from Walt Disney World. This beautifully renovated and fully furnished 6-bedroom, 4-bath single-family pool home offers 2,812 square feet of thoughtfully designed living space, combining resort-style living with outstanding vacation-rental appeal. Step inside to a bright, spacious floor plan featuring two primary suites, stylish finishes, stone countertops, and inviting living and dining spaces designed for entertaining and relaxing. The home's professionally themed spaces elevate the guest experience, including an impressive Avengers-inspired game room and Mickey, Toy Story, and Star Wars-themed bedrooms that create a memorable Central Florida getaway. Outdoors, enjoy your own private screened pool and spa with a generous pool deck, the perfect setting to relax in the Florida sunshine after a day at the theme parks. Located within the 24-hour guard-gated Windsor Hills community, owners and guests enjoy an exceptional collection of resort amenities including a spectacular water park, resort-style swimming pool and hot tub, clubhouse, fitness center, movie theater, game room, playground, tennis and basketball courts, volleyball, putting green, dog park, and on-site Marketplace & Grill. Windsor Hills is an established vacation rental community offering an outstanding location near Walt Disney World and convenient access to Central Florida's world-famous attractions, dining, shopping, and entertainment. Whether you are searching for a luxurious Florida vacation residence, a second home, or a property positioned for the short-term rental market, this turnkey Windsor Hills home delivers the location, space, amenities, and guest appeal today's buyers are looking for. Schedule your private showing and experience everything this exceptional property has to provide.

7772 Basnett Circle, Kissimmee

$698,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 7 SubDv. ⋅ 34747 Zip Code

Welcome to your ultimate vacation retreat, ideally located just 5 miles from Walt Disney World in the highly sought-after Windsor Hills Resort! This beautifully maintained 6-bedroom, 4-bathroom pool home offers the perfect combination of comfort, entertainment, and resort-style living, making it an excellent choice as a second home or high-performing short-term rental investment. The property has been meticulously cared for and features numerous significant upgrades, including luxury vinyl plank flooring throughout (2022), upstairs A/C (2020), downstairs A/C (2022), pool heater (2021), pool motor/pump (2023), pool safety fence (2023), and dishwasher (2026). The home also features a durable tile roof, offering added longevity and value. The main level includes a bedroom and full bathroom, ideal for guests or multi-generational living. Upstairs, you'll find two spacious suites plus three themed guest bedrooms, providing plenty of room for family and vacation guests. The garage has been converted into a fun-filled game room, creating additional entertainment space for all ages. Step outside to your private screened-in pool, the perfect place to relax and enjoy the Florida sunshine. The HOA fee includes lawn service, daily valet trash pickup, internet, and basic cable. Windsor Hills offers outstanding resort amenities, including 24/7 manned gated entry, a resort-style clubhouse and community pool, sports courts, putting green, and more. Conveniently located just minutes from Disney theme parks, major Central Florida attractions, dining, shopping, championship golf courses, airports, and Florida's famous beaches, this is an exceptional opportunity to own a turn-key vacation home in one of Central Florida's most desirable resort communities.

2536 Holtrock Street, Kissimmee

$690,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 6 SubDv. ⋅ 34747 Zip Code

Busy rental: Next available to view is July 26! Minutes to Animal Kingdom! Guest friendly, fun, and full of upgrades! This vacation home has been thoughtfully improved with themed spaces throughout, including a fully themed garage/game area guests will love. Located right next to one of the playgrounds, it offers extra convenience for families and a standout experience in the highly desirable Windsor Hills community.

2623 Pawnall Street, Kissimmee

$665,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 5 SubDv. ⋅ 34747 Zip Code

Beautifully professionally decorated and totally renovated, this exceptional vacation home is truly turnkey and designed to impress both owners and guests alike. The spacious interior has luxury vinyl plank flooring throughout the first floor, upstairs hallway, and primary bath, creating a stylish and durable modern look. The home is packed with entertainment and fun, including an exciting game room with basketball, air hockey, and arcade game that guests of all ages will love. The themed bedrooms bring the magic to life with incredible Mickey Mouse and Harry Potter-inspired designs, making this property highly desirable as a short-term rental or family retreat. Located in the highly sought-after Windsor Hills Resort, one of the closest resort communities to Walt Disney World, owners and guests enjoy world-class amenities including a huge lagoon-style pool, water park with slides and splash pad, clubhouse with fitness center and movie theater, sundry deli, tennis courts, and playgrounds. Whether you are looking for a vacation getaway, investment property, or income-producing short-term rental, this stunning home checks every box.

7805 Beechfield Street, Kissimmee

$659,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code

Welcome to 7765 Tosteth Street, a beautifully appointed vacation home in the heart of Windsor Hills Resort — Orlando's premier gated short-term rental community, just minutes from Walt Disney World. This spacious 6-bedroom, 4-bathroom pool home offers 2,812 sq ft of thoughtfully designed living space, perfect for large groups looking for comfort, privacy, and resort-style amenities. The open-concept main floor features a generous living and dining area, a fully equipped kitchen, a first-floor bedroom with full bath — ideal for guests who prefer single-level living — a dedicated laundry room, and a game room for added entertainment. Step outside to your private screened pool with heated spa, surrounded by a covered patio and deck — the perfect setting for relaxing afternoons under the Florida sun. Windsor Hills Resort amenities include a clubhouse, resort-style community pool, waterpark, fitness center, game room, tennis courts, and 24-hour gated security — everything your guests need without ever leaving the community. Whether you're looking for a turn-key investment property with strong short-term rental potential or a private family retreat steps from the magic of Orlando, 7765 Tosteth Street is ready to deliver. Offered fully furnished and ready to generate income from day one.

7765 Tosteth Street, Kissimmee

$649,000

5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code

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.

7788 Basnett Circle, Kissimmee

$648,000

5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 06 SubDv. ⋅ 34747 Zip Code

Lucky 7 !! This well-maintained 5 bedroom, 5 bath home in the 5-Star Windsor Hills Resort offers buyers a rare opportunity to acquire a proven, income-producing short-term rental just minutes from Walt Disney World—one of the strongest and most reliable vacation-rental corridors in the United States. Designed with the resort’s most desirable 5-bedroom open floorplan, the home consistently attracts large families and multi-generational groups, maximizing both occupancy and nightly rate potential. For buyers seeking immediate continuity of income, the seller is willing to transfer future bookings, allowing a seamless transition with no downtime. Interior Features for High-Demand Guest Use Multiple dining areas and a spacious main living room built to accommodate high guest volume Stainless steel appliances in the kitchen Two ground floor ensuites plus an additional twin bedroom—ideal for multi-family bookings Two junior suites upstairs, each with a private bath, supporting strong guest satisfaction and repeat stays Converted garage game room with foosball and pool tables—an amenity that significantly boosts rental performance Outdoor & Resort Amenities The screened lanai features a private heated pool, a top-performing feature for year-round bookings. Windsor Hills remains one of Central Florida’s top-performing vacation rental communities, offering: Lagoon-style resort pool Clubhouse, fitness center, and marketplace Tennis, racquetball, basketball, and volleyball Theater, arcade, playgrounds, and putting greens 24-hour guarded security Its unmatched proximity to Disney drives consistent occupancy, premium nightly rates, and strong year-round demand. Investment Highlights This property represents a rare chance to acquire a low-maintenance, high-demand, income-generating asset in one of the region’s most reliable STR markets. Windsor Hills is a purpose-built resort community offering amenities for all ages while remaining less than five minutes from Walt Disney World—making it an ideal choice for families and groups seeking affordable luxury in a prime location.

7777 Teascone Boulevard, Kissimmee

$640,000

6 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 03 SubDv. ⋅ 34747 Zip Code

Welcome to 2671 Manesty Lane, fully furnished vacation home in the highly desirable Windsor Hills Resort, one of the closest resort communities to Walt Disney World. Located just minutes from Disney, this home is an outstanding opportunity for a vacation getaway, second home, or income-producing short-term rental. Step inside to an open and inviting floor plan that seamlessly connects the living, dining, and kitchen areas, creating the perfect space for relaxing and entertaining. The home has been thoughtfully maintained and is move-in or rental-ready, allowing you to start enjoying it from day one. Windsor Hills is one of Central Florida's premier resort communities, offering exceptional amenities for owners and guests alike. Enjoy a 24-hour guard-gated entrance, a resort-style pool with water slides and splash features, hot tub, fitness center, movie theater, arcade, tennis courts, basketball courts, playgrounds, and a clubhouse with endless activities for the whole family. Beyond the resort, you'll be just minutes from Walt Disney World, with easy access to Universal Orlando, SeaWorld, championship golf courses, shopping, dining, and all of Central Florida's world-famous attractions. Whether you're looking to expand your investment portfolio or own your own piece of the magic, this turnkey home offers the perfect combination of location, comfort, and resort-style living.

2671 Manesty Lane, Kissimmee

$639,000

5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 6 SubDv. ⋅ 34747 Zip Code

Welcome to this beautifully maintained 5-bedroom, 5-bath pool home located just 5 miles from Walt Disney World® in the highly desirable Windsor Hills Resort. Situated on a premium corner lot with a west-facing front and unobstructed conservation views, this property offers privacy, strong rental appeal, and an ideal layout for both personal use and short-term rental investment. The open floor plan features a spacious central living area with multiple dining options including a formal 8-seat dining table, breakfast nook, and kitchen bar seating. The fully equipped kitchen overlooks the main living space, creating an ideal setup for entertaining. The converted garage has been transformed into a game room complete with a pool table and gaming area, perfect for those days lounging around. The first floor includes a primary suite with private ensuite bath, along with two additional guest bedrooms—each with their own bathroom. Upstairs you’ll find two themed bedrooms, both with private baths. Upgraded vinyl flooring (2022) enhances all bedrooms. Head outside to your private pool area, enjoy Florida living in the screened-in lanai for added tranquility. Recent updates include new vinyl flooring (2022), new second-floor AC unit (2022), and new pool pump (2024) The HOA fee includes lawn service, irrigation maintenance, daily valet trash pickup, internet, basic cable and a 24/7 manned guard gate. Community amenities include a large clubhouse, tropical setting community pool with water park slide, zero entry pool, open air lounge center, convenience store, fitness center, movie theater, billiards/game Room, table tennis, lighted basketball & tennis courts, sand volleyball court, putting green, RV/Boat parking area, two kiddie park/playgrounds. 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. This home is sold fully furnished and ready for you to move in and make it your own. 2026 upcoming bookings may convey to the new owner if the current property manager is retained. Excellent opportunity for a primary residence, vacation home, or income-producing property. Schedule a Viewing today, don't miss out on this opportunity!

2621 Archfeld Boulevard, Kissimmee

Windsor Hills Homes for Sale

Windsor Hills Homes For Sale