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$699,900
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
$629,900
5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code
Whether you're looking for an income-producing vacation rental or a personal retreat, this 5-bedroom, 5-bath home in the highly desirable gated community of Windsor Hills is an excellent opportunity. The kitchen is positioned at the front of the home and overlooks the formal dining area, creating a welcoming space for family meals and entertaining. The living room is located at the rear of the home and opens to the screened-in pool deck, offering a relaxing space to enjoy the Florida sunshine. Three bedrooms including the primary are conveniently located on the first floor, with two sharing a jack and jill bathroom set up, while the remaining bedrooms and bathrooms are upstairs, providing comfort and privacy for guests. The garage has been converted into a fun games room with pool and foosball tables, adding extra appeal for renters. Windsor Hills is one of the closest resorts to Disney and features outstanding amenities, including a resort-style pool with water slides, clubhouse, fitness center, and sports courts. Ideal for short-term rental investment, second home, or full-time residence.

7795 Basnett Circle, Kissimmee
$615,000
4 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 1 SubDv. ⋅ 34747 Zip Code
Welcome to this exceptional turnkey vacation rental opportunity in the highly sought-after Windsor Hills Resort! This fully furnished 4 bedroom, 4 bath home is designed to entertain guests of all ages with custom themed bedrooms, a game room, private screened pool and spa, and an inviting open-concept floor plan perfect for any gatherings. The spacious kitchen and a large breakfast bar overlook the main living area. Guests will love the professionally themed Disney-inspired bedrooms, while the converted garage game room provides endless entertainment. Located just 5 minutes from Disney and minutes from Universal Studios, SeaWorld, Legoland, Shopping, Dining, and more, this property offers both an incredible vacation experience and strong income-producing potential. Windsor Hills Resort features many amenities including a clubhouse, fitness center, movie theater, arcade, resort-style pool with waterslides, sports courts, playgrounds, and gated security. Whether you're looking for a personal retreat, investment property, or both, this home is ready to impress. Schedule your private showing today!

7743 Comrow Street, Kissimmee
$609,000
5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 3 SubDv. ⋅ 34747 Zip Code
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.

Kissimmee
$589,999
5 Beds ⋅ 5 Baths ⋅ Windsor Hills Ph 06 SubDv. ⋅ 34747 Zip Code
Highly Desirable Windsor Hills Subdivision – Just 4.5 Miles from Disney! Welcome to Windsor Hills, a premier guard-gated community built by Pulte, known for its luxury and convenience. This fully furnished, turnkey home features one of the best floor plans in the neighborhood with 5 bedrooms and 5 bathrooms. The garage has been transformed into a custom theater room complete with projector, leather seating, a foosball table, multiple arcade games, a mounted AC unit, and carpeted flooring. Inside the home, the living and dining areas are beautifully appointed with leather furniture and a stunning dining table from Havertys. Custom window treatments and vibrant colors flow throughout the home. This home features many upgrades: main home HVAC in 2018, hot water heater in 2025, pool heater in 2025, 6 arcade games in 2024, movie projector in 2024, wall HVAC in movie room in 2024, paint in the living and dining room in 2024, bathroom vents in 2026, side by side refrigerator in 2026 and pool heater compressor start capacitor 2026. Each bedroom is decorated, including a charming themed Peter Pan bunk room that is a must-see. The kitchen is fully stocked and features stainless steel appliances, granite countertops, and two large windows that bring in natural light, perfect for enjoying meals in the cozy breakfast nook. Tile flooring extends through the main living areas and bathrooms, and ceiling fans are installed throughout the home for added comfort. Step outside to the stunning pool and spa area, complete with a new pool pump, a brick paver deck, a covered lanai with ceiling fans, and ample outdoor furniture. Beyond the pool, a lush green lawn bordered by a wrought-iron fence provides a serene backdrop. This home also boasts a new water heater, ensuring modern efficiency and reliability. Directly across the street, you’ll find a park with a two-seater swing set to relax and enjoy the outdoors. Windsor Hills is one of the few communities that allows RV and trailer parking, with an oversized lot dedicated to these vehicles. The neighborhood also boasts a wide array of amenities, including a clubhouse with a waterslide, game room, theater, on-site market and food service, tennis and pickleball courts, volleyball, a putting green, basketball courts, and a fully equipped gym. For golf enthusiasts, the public Mystic Dunes Golf Course is right next door, with several other courses just minutes away. Don’t miss this incredible opportunity to own a home in one of the most sought-after vacation communities in Central Florida!

2615 Pawnall Street, Kissimmee
$585,000
4 Beds ⋅ 4 Baths ⋅ Windsor Hills Resort SubDv. ⋅ 34747 Zip Code
Step into luxury and nonstop fun at 7747 Teascone Blvd, an extraordinary 4-bedroom, 4-bathroom retreat nestled in the prestigious, 24-hour manned gated community of Windsor Hills Resort. This fully furnished paradise is engineered for ultimate relaxation and entertaining, boasting a private screened-in pool and spa alongside a garage conversion transformed into a game area. With every spacious bedroom featuring its own dedicated bathroom, this home offers maximum privacy and comfort—making it an irresistible opportunity whether you are seeking a high-yield short-term rental investment, a dream vacation getaway, or a vibrant primary residence. Beyond the front door, residents and guests gain access to Windsor Hills' premier resort-style amenities, including a zero-entry lagoon pool, the Sir Windsor AquaVenture water park with dual speed slides, a hot tub, state-of-the-art fitness center, 40-seat HD movie theater, sports courts (tennis, basketball, and sand volleyball), putting green, and on-site dining at the marketplace and grill. Situated just minutes from Walt Disney World, top-tier golf courses, world-class dining, and premier Central Florida shopping, this property offers an unbeatable location with endless potential. (New A/C 2024)

7747 Teascone Boulevard, Kissimmee
$585,000
4 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 6 SubDv. ⋅ 34747 Zip Code
Motivate Seller...Seller may consider buyer concessions if made in an offer. Request must be made by the Buyer(s) in a written and signed contract offer and will be negotiated as part of the terms and conditions of an executed contract. Features recent August 2026 mechanical upgrades (Brand-new A/C & pool pump) and excellent rental potential. Fully furnished and rental-ready. Schedule your showing today! Welcome to 7755 Grassendale Street! This beautifully maintained, TURNKEY 4-bedroom, 4-bath home offers exceptional comfort and resort-style Florida living. Ideal as a primary residence, vacation home, or short-term rental, this home is ready to enjoy! The open-concept floor plan features a welcoming foyer, spacious dining area, family room, and well-appointed kitchen with stainless steel appliances, granite countertops, breakfast bar, and breakfast nook. Tile flooring complements the main living areas, while all bedrooms feature luxury vinyl plank flooring and tasteful themed décor. The converted 2-car garage, completed in 2021, is fully air-conditioned and features an impressive entertainment space with a home theater, gaming consoles, and sit-down arcade game—perfect for family fun and entertaining. Enjoy your private Florida retreat with a covered lanai and refurbished pool and spa (2022). Relax poolside, unwind in the spa, and soak up the sunshine! Located in a 24-hour guard-gated resort community with a 10,000-square-foot clubhouse, lagoon-style pool with water slides, fitness center, movie theater, sports courts, playground, and walking trail. Conveniently located just minutes from Disney, with dining, shopping, entertainment, and everyday conveniences nearby. With major updates, turnkey furnishings, a fantastic entertainment space, and private pool and spa, 7755 Grassendale Street is truly a MUST SEE!

7755 Grassendale Street, Kissimmee
$569,900
4 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 7 SubDv. ⋅ 34747 Zip Code
Exceptional Windsor Hills Pool Home with One of the Community’s Most Spectacular Views! Welcome to 2568 Archfeld Boulevard, where luxury, comfort, and investment potential come together in one of Central Florida’s premier vacation home communities. This beautifully appointed home offers soaring 10-foot ceilings, creating an open, spacious feel that sets it apart from the competition. Designed with entertaining in mind, the custom garage game room provides endless fun for guests while maximizing rental appeal. The home is being offered fully furnished with a designer furniture package, allowing you to begin enjoying or renting the property immediately. Step outside and discover what truly makes this property exceptional. The southwest-facing private pool is perfectly positioned to capture Florida’s breathtaking afternoon sunshine and spectacular sunset skies. Unlike many homes in the community, you’ll enjoy expansive, open views with no direct rear neighbors and no back-to-back pool views, creating an unmatched sense of privacy and tranquility. Widely regarded as one of the finest views in all of Windsor Hills, this outdoor oasis is the perfect place to relax after a day at the parks or entertain family and guests. For investors, future rental bookings may be included, offering the opportunity for immediate income after closing. Whether you’re searching for a luxury vacation retreat, a high-performing short-term rental, or both, this exceptional Windsor Hills home delivers an unbeatable combination of location, privacy, designer finishes, and income potential—just minutes from Walt Disney World, shopping, dining, and Orlando’s world-famous attractions.

2568 Archfeld Boulevard, Kissimmee
$540,000
4 Beds ⋅ 4 Baths ⋅ Windsor Hills Ph 5 SubDv. ⋅ 34747 Zip Code
LOCATION! LOCATION! Turnkey 4-Bed, 4-Bath Home in Windsor Hills Resort – Minutes from Disney! Step into this fully furnished, move-in ready home featuring 1,878 sq ft of open-concept living space. The spacious layout flows seamlessly from the bright living areas to a private screened-in pool and spa—perfect for relaxing or entertaining. The chef’s kitchen, plush bedrooms, and tile flooring throughout common areas provide both comfort and style. Recent upgrade includes new water heater (2025), and the roof will be replaced with an accepted offer, giving you peace of mind for years to come. Enjoy resort-style amenities just steps from your door: a clubhouse with movie theater, fitness center, sundry shop, and arcade game room; a water park with zero-entry pool, slides, and hot tub; plus, tennis, basketball, volleyball courts, putting green, and a playground. Whether you’re looking for a vacation home, short-term rental, or full-time residence, this property combines luxury, convenience, and value in one of Kissimmee’s most desirable communities. Schedule your private tour today!

7739 Teascone Boulevard, Kissimmee
$449,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 2 SubDv. ⋅ 34747 Zip Code
Beautifully End-Unit Townhome in Windsor Hills! In a premier 24-hour guard-gated community! Perfect for year-round living, a vacation retreat, or a profitable short-term rental. Step inside to a bright, open-concept main floor, a kitchen with, breakfast bar, and premium appliances. The open living and dining area opens through sliding glass doors to your private screened-in pool, ideal for relaxing or entertaining. A main-level bedroom and full bath supply comfort and convenience for guests. Upstairs, the primary suite provides a walk-in closet and an en-suite bath. An additional bedroom, full hall bath, and in-unit laundry complete the second floor. Enjoy resort-style living with Windsor Hills with unmatched amenities: a community pool and hot tub, water park, fitness center, tennis, basketball, and volleyball courts, game room, movie theatre, tot lot & recreation park, plus an on-site marketplace and grill. Just minutes from Disney World and area attractions - this is the lifestyle you’ve been dreaming of. Schedule your private showing today!

7667 Otterspool Street, Kissimmee
$425,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 2 SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully maintained and upgraded 3-bedroom, 3-bathroom pool townhome located in the highly sought-after Windsor Hills Resort, just minutes from Walt Disney World. Offered fully furnished, this turnkey property is ideal as a primary residence, vacation home, or income-producing short-term rental investment. This exceptional home stands out within the community thanks to its numerous quality upgrades and thoughtful enhancements. The updated kitchen features upgraded cabinetry, granite countertops, and stainless-steel appliances, creating a stylish and functional space for owners and guests alike. Luxury vinyl flooring extends throughout the entire home, providing durability, easy maintenance, and a modern look with no carpet anywhere. A major improvement includes a NEW AC system installed in June 2020, offering peace of mind and energy efficiency. Upstairs, guests will love the tastefully themed Disney bedroom, while each bedroom has been thoughtfully designed to create a magical and memorable Disney vacation experience. Step outside to your private screened-in pool, perfect for relaxing after a day at the theme parks. Whether you're seeking a high-performing vacation rental or a personal getaway near Disney, this home checks all the boxes. Located within the gated Windsor Hills Resort community, residents and guests enjoy world-class amenities including a lagoon-style resort pool, water park, thrilling water slides, movie theater, fitness center, game room, sports courts, onsite convenience store, bar and grill, playgrounds, and more. Just minutes from Walt Disney World, Universal Orlando Resort, shopping, dining, and entertainment, this property offers the perfect combination of location, comfort, and investment potential. Don't miss this opportunity to own your own piece of the magic—schedule your private showing today!

7674 Otterspool Street, Kissimmee
$419,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 4 SubDv. ⋅ 34747 Zip Code
Welcome to Windsor Hills, one of Central Florida's premier resort-style gated communities, where comfort, convenience, and investment potential come together in this beautifully furnished 3-bedroom, 3-bathroom townhome with a private pool. Whether you're searching for a vacation retreat, full-time residence, or a turnkey short-term rental investment, this home is ready to impress. Step inside to an open-concept floor plan that seamlessly connects the living, dining, and kitchen areas, creating the perfect space for entertaining and relaxing after a day of exploring Central Florida. The thoughtfully designed layout includes a first-floor guest bedroom and full bathroom, offering convenience and privacy for guests or multi-generational living. Upstairs, the spacious primary suite features a private en-suite bathroom, while the third bedroom is a dream for every Mickey Mouse fan, complete with themed décor and full bathroom, making it a memorable space for family and guests alike. Sliding glass doors from the living area open to your own private screened pool, providing the perfect place to unwind, soak up the Florida sunshine, or enjoy an evening swim in complete privacy. Ideally located just minutes from Walt Disney World, this exceptional property places you near Margaritaville Resort, world-class shopping, dining, golf, and major highways for easy travel throughout Central Florida. Orlando International Airport, SeaWorld, Universal Orlando Resort, and both Florida coasts are all within convenient driving distance, making weekend beach trips a breeze.

2530 Maneshaw Lane, Kissimmee
$419,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 2 SubDv. ⋅ 34747 Zip Code
ANOTHER EPIC LISTING!!! Welcome to this beautiful appointed 3 bedroom - 3 bath townhome in in beautiful Windsor Hills. This is your chance to own a vacation property with a private pool that won't break the bank. This home offers the perfect blend of comfort, convenience and resort-style living. Ideally situated with no rear neighbors, the property provides added privacy and a peaceful setting while also being close to the happenings of the community. Inside your villa you have a thoughtfully designed layout featuring a spacious living area that seamlessly opens to your own private screened pool. The home provides a most desired feature in a downstairs bedroom and bath. Upstairs you will find two additional bedrooms and bathrooms along with a landing and gathering area. All guests will have their space. No carpet throughout the home makes for easy maintenance. Located within a sought -after 24-hour gated resort community, residents and guest enjoy access to an impressive array of amenities. These include tennis, basketball, and volleyball courts, along with a state-of-the-art fitness center and game room. The community shines with its resort-style water attractions-featuring a lazy river, thrilling water slides, splash park, and an expansive pool and spa area. Families will also enjoy the magical castle playground an on-site movie theatre, while the on-site dining and drinks add convenience and vacation like atmosphere. Perfectly positioned near major attractions, this townhome is not only an amazing personal getaway but also a highly desirable vacation rental opportunity. Its proximity to the water park and resort amenities makes it especially for short term guest seeking fun, relaxation, and convenience all in one place. Make sure if you are looking.... check this out.

2545 Renshaw Street, Kissimmee
$414,900
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 2 SubDv. ⋅ 34747 Zip Code
Welcome to 7677 Fitzclarence St, a beautifully maintained and fully furnished townhome located in the highly desirable, guard-gated community of Windsor Hills Resort just minutes from Walt Disney World. This turnkey 3 bedroom, 3 bathroom home offers the perfect combination of comfort, convenience, and resort-style living, making it ideal as a primary residence, second home, or income-producing vacation property. Featuring a desirable open-concept floor plan with spacious living areas, a well-appointed kitchen, and a private screened pool area, this home is designed for both relaxation and entertaining. This property has been thoughtfully maintained with recent updates including a brand-new air conditioning system, brand-new hot water heater, and newly replaced pool screens, providing peace of mind for the next owner. The home comes fully furnished and ready for immediate enjoyment, offering a true turnkey opportunity with a strong rental history. Currently operating as a highly active and heavily booked Airbnb, this property has proven income potential while still providing the flexibility to enjoy your own Florida retreat. The functional layout includes a first-floor bedroom and full bathroom, with additional bedrooms upstairs including a spacious primary suite, providing privacy and comfort for owners and guests. Step outside to the screened private pool area and enjoy the Florida lifestyle year-round. Located in Windsor Hills, owners and guests enjoy access to exceptional resort amenities including 24-hour gated security, a clubhouse, resort-style pool, fitness center, recreation areas, sports courts, and more. With its unbeatable location close to Disney, shopping, dining, and major attractions, combined with strong rental demand, recent upgrades, and a proven vacation rental track record, 7677 Fitzclarence St is a rare opportunity to own a move-in-ready property in one of Central Florida’s most sought-after communities. This is the perfect blend of personal enjoyment and investment opportunity — just bring your suitcase and start enjoying everything Orlando has!

7677 Fitzclarence Street, Kissimmee
$410,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 4 SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully maintained 3-bedroom, 3-bath end-unit townhome featuring a private splash pool, located in the highly desirable Windsor Hills Resort, a premier guard-gated community just minutes from Walt Disney World. The home features a well-appointed kitchen with granite countertops, custom backsplash, and updated appliances (2019–2021), creating a functional and stylish space for everyday living or entertaining. All three bathrooms are upgraded with granite countertops, and each bedroom includes its own bathroom, two being en-suites, providing privacy and convenience for owners and guests alike. The HVAC system was replaced in 2020, offering peace of mind and energy efficiency. The thoughtfully designed layout includes a fun Mickey Mouse–themed third bedroom, adding a touch of Disney magic that guests will love. As an end unit, the home benefits from additional natural light and a more private setting. Step outside to your screened-in private splash pool, perfect for unwinding after a day at the parks. Windsor Hills Resort is renowned for its resort-style amenities, including a heated lagoon pool with waterslides, splash pad, clubhouse, fitness center, arcade, playground, tennis, basketball courts, and more. The HOA covers cable/internet, exterior maintenance and trash service, allowing for truly low-maintenance ownership. Ideally located near shopping, dining, and major attractions, this turnkey townhome is an exceptional opportunity in one of Central Florida’s most sought-after resort communities.

7681 Sir Kaufmann Court, Kissimmee
$400,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 2 SubDv. ⋅ 34747 Zip Code
NEW ROOF 2026 PRIVATE YARD VIEWS! Pool heater 2022,Very close to the waterpark! Welcome to your dream townhouse featuring three bedrooms and three bathrooms in a vibrant community setting. This beautiful home offers the luxury of a private pool with no direct rear neighbors, providing complete privacy for your outdoor enjoyment. The updated kitchen showcases elegant stone countertops, a breakfast bar, and bright appliances that make cooking a pleasure. Throughout the main floor, you'll find luxury ceramic plank flooring that combines durability with style. Each bedroom includes its own private bathroom, ensuring comfort and convenience for everyone. Generous closets provide ample storage space throughout the home. The community amenities are truly impressive, featuring tennis courts for the sports enthusiasts, a splash park complete with slide for fun, and a magical castle playground can let your imaginations run wild. You can unwind at the community pool and spa, shoot hoops on the basketball court, or grab a bite at the on-site restaurant. Location couldn't be better, with easy access to shopping and dining options nearby. Theme park lovers will appreciate the convenient proximity to major attractions, making this the perfect home base for both daily living and entertainment. This townhouse offers an excellent blend of private luxury and community amenities, creating a lifestyle that's both relaxing and exciting. Whether you're hosting poolside gatherings, enjoying community activities, renting with AirBNB or exploring nearby attractions, this home provides the perfect setting for making lasting memories with family and friends.

2556 Renshaw Street, Kissimmee
$395,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 02 SubDv. ⋅ 34747 Zip Code
TURNKEY WINDSOR HILLS END-UNIT TOWNHOME! This beautifully furnished 3 bedroom, 3 bathroom vacation home is located in one of the most established short-term rental resorts near Disney. The home features a private splash pool, bright end-unit layout with extra windows, tasteful furnishings, and a themed Mickey bedroom with custom wall murals and themed lighting. Recent updates include a replaced AC system, washer and dryer, improved wooden stairs, and ongoing furnishing and mattress updates to keep the home guest-ready. With approximately 183 Airbnb reviews and a 4.9-star rating, this property has a strong rental history and is ready for the next owner to continue using as a vacation rental, second home, or personal getaway. Windsor Hills offers resort-style amenities including a clubhouse, fitness center, movie theater, arcade, sundry shop, lagoon-style pool, water slides, hot tub, playgrounds, sports courts, putting green, and more. Located just minutes from Disney, shopping, dining, and major Central Florida attractions. Fully furnished, well maintained, and positioned as a desirable end unit, this is an excellent opportunity in the heart of the Disney vacation rental corridor. Schedule your showing today!

7683 Fitzclarence Street, Kissimmee
$394,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 2 SubDv. ⋅ 34747 Zip Code
SOUTH-FACING POOL! Welcome to a standout vacation home in the popular Windsor Hills Resort, just minutes from the magic of Disney! This beautifully furnished 3-bedroom, 3-bathroom townhome offers an exceptional blend of comfort, style, and rental potential. Guests are immediately drawn to the Disney-inspired living room, designed to create a memorable vacation experience from the moment they walk through the door. The home also features an incredible Toy Story-themed bedroom that delights younger guests, while the spacious first-floor primary suite showcases a unique Incredibles theme, making it both fun and functional for families visiting the area. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating the perfect gathering space for entertaining and relaxing after a day at the parks. A convenient first-floor bedroom with bath provides easy accessibility for owners and guests alike. Upstairs, an additional ensuite bedroom offers privacy and comfort, while durable flooring throughout the home eliminates carpet maintenance and is ideal for a high-performing short-term rental property. Step outside to your private screened lanai and enjoy the highly desirable south-facing heated pool, perfect for soaking up the Florida sunshine year-round. Whether guests are spending the afternoon poolside or unwinding after an exciting day at Disney, this outdoor oasis is sure to impress. Located within the gated Windsor Hills Resort community, residents and guests enjoy world-class amenities including a lagoon-style resort pool, water park, thrilling water slides, movie theater, fitness center, game room, sports courts, onsite convenience store, bar and grill, playgrounds, and more. Just minutes from Walt Disney World, Universal Orlando Resort, shopping, dining, and entertainment, this property offers the perfect combination of location, comfort, and investment potential. Don't miss this opportunity to own your own piece of the magic—schedule your private showing today!

7654 Otterspool Street, Kissimmee
$380,000
3 Beds ⋅ 3 Baths ⋅ Windsor Hills Ph 4 SubDv. ⋅ 34747 Zip Code
Beautiful community Windsor Hills, located only 2 miles from Disney, tons of amenities, private screened heated splash pool!

7663 Sir Kaufmann Court, Kissimmee