Homes For Sale in Kissimmee 34747 - 850 homes

Remarks: 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)

Remarks: Under contract-accepting backup offers. Great opportunity to own a beautifully maintained vacation home located in the highly desirable Windsor Hills Resort! This spacious and well-designed property offers an open floor plan ideal for both relaxation and entertaining. The home features themed bedrooms that enhance the vacation experience, along with a private screened-in pool area perfect for enjoying the Florida lifestyle. Laminate flooring throughout provides a modern look with easy maintenance. Just minutes from Walt Disney World and major Orlando attractions, this property is perfectly positioned for short-term rentals or personal use. Windsor Hills Resort is a gated community offering resort-style amenities, including a clubhouse, resort pool with water slide, fitness center, movie theater, playground, and more. Currently operating as a short-term rental. Schedule your showing today and don’t miss this incredible investment opportunity!

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

Listing Agent: Danilo Aquino (689-243-6300)

Remarks: Welcome to resort-style living in this beautifully furnished 2-story townhome located in a guard-gated community packed with incredible amenities! Whether you’re looking for a primary residence, vacation getaway, or short-term rental investment, this property checks all the boxes. Inside, you’ll find tile flooring throughout the first floor, brand-new carpet on the stairs and second level, ceiling fans in all bedrooms, and an inside laundry room conveniently located downstairs. All bedrooms are upstairs, including the spacious primary suite featuring a private balcony and ensuite bathroom. The upstairs bathrooms have been tastefully renovated, and the home is being sold fully furnished and decorated for a true turnkey opportunity. Enjoy a vacation lifestyle every day with access to 2 resort-style pools, a tiki bar, fitness center, game room, tennis courts, basketball court, mini golf, bicycles, walking trails, playgrounds, grilling areas, lush tropical landscaping, and more! Short-term rentals are allowed, making this an excellent investment opportunity in a sought-after community.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Cindy Brads (407-625-7443)

Remarks: Under contract-accepting backup offers. GREAT Condo Location and close to everything! This fabulous 2/2 Condo in sought after Blossom Park, ground floor, Large and spacious rooms so you can spread out! Inside laundry room located just off the kitchen, Beautiful community amenities. 10 MINUTE Walk to NEW Shoppes at Celebration Place and Bus Stop! 5 Minute drive to Downtown CELEBRATION, Hospital and I4! all right across the street and a 10 Minute drive to Disney World! Zoned for "A" Rated Celebration High School! BEST VALUE IN THE DISNEY/CELEBRATION corridor! There is a Community Pool, Tennis/Basketball Court, Playground and a Fitness center. Unwind on deck near Community Lake at your leisure.

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

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

Remarks: Welcome to your dream vacation and stunning fully furnished 5 bedroom, 4 bathroom pool home located on a corner lot in the highly sought after Windsor at Westside Resort. Perfectly designed for indoor/outdoor entertaining and is excellent income producing short-term rental or a fantastic personal retreat. Designed with lots of space in mind this two story layout and open floor plan is the perfect getaway. The home sleeps up to 14 comfortably and features large living areas with plenty of space for relaxing. The first floor master bedroom offers privacy and space, the kitchen has granite countertops and stainless steel appliances with a nice island opening to the dining room and living space. Enjoy the gated resort style amenities with the zero entry point pool, water slide, lazy river, and water playground. It boasts a clubhouse, a lake with a pier, fitness center, volleyball courts, sundry shop and video arcade. This is an ideal location as it offers easy access to Disney World attractions and many other theme parks in the area. Welcoming any and all offers.

Listing is courtesy of: BEACHES WITHIN REACHES REALTY (386-864-3154)

Listing Agent: Abby Baker (386-864-3154)

Remarks: Your own private getaway at 3222 Cupid Place, a stunning 4-bedroom, 3-bathroom townhome in the prestigious gated community of West Lucaya Village. This fully furnished home is tailored for the high-demand short-term rental market, offering a perfect mix of modern style and practical comfort. Ideally situated in the heart of the tourist corridor, you’re just a short drive from Walt Disney World’s gates, as well as the vibrant dining options, championship golf courses, and luxury shopping that define Central Florida. Outside, the West Lucaya Village resort lifestyle offers a range of impressive amenities. Guests and owners can relax by the swimming pool and jacuzzi, stay active in the modern fitness center, or enjoy the clubhouse game room and kids’ play area. The community also includes a basketball court and scenic picnic spots for outdoor gatherings. Whether you’re seeking a high-performing addition to your investment portfolio or a dream vacation home that pays for itself, this property delivers on all fronts.

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

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

Remarks: This FULLY FURNISHED, FIRST FLOOR condo is ready for its next owner - for primary living or short and long-term rental! As you walk in, you are greeted by a large OPEN CONCEPT kitchen with tons of cabinets and countertop space, including a large breakfast bar seating area. Continuing through, you have a spacious dining and living area that looks out to your private patio! The primary suite features a WALK-IN CLOSET, oversized vanity, and updated tile WALK-IN SHOWER. The guest bedroom is set apart from the other allowing for added privacy, and also features a large vanity and tiled shower and tub. Stepping out from the living area, you have a serene COVERED PATIO with views of the nearby green space! The Villas at Secret Lake Condo Community features a clubhouse, community pool, fitness center, dog park, walking trails and more! Plus, the HOA fee includes cable, internet, water, trash, sewer, and exterior maintenance allowing for total easy and care-free living! The community is located just off US-192, allowing easy access to Walt Disney World, Margaritaville, I-4 and all of the area's best shopping, dining, and entertainment destinations. Add this home to your investment portfolio before it is gone!

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Sophia Gordon, Llc (239-898-1841)

Remarks: Step into this stunning and beautifully furnished 5-bedroom, 4-bathroom townhome nestled within an exclusive resort-style community. Designed with comfort and style in mind, this spacious home offers a modern layout perfect for families. Enjoy your own private pool, ideal for relaxing afternoons or entertaining in the Florida sun. The community itself is rich with amenities, including clubhouse access, fitness facilities, resort-style pools, sports courts, playgrounds, and more—ensuring there’s something for everyone to enjoy. Don't miss out on this great opportunitiy! Tour this amazing property today!

Listing is courtesy of: GOLDEN KEY REAL ESTATE SOLUTIONS LLC (407-801-8283)

Listing Agent: Gleyson Silva (407-575-7332)

Remarks: Priced to sell! This fully furnished 6 bedroom, 4.5 bathroom vacation home is already operating and generating short term rental income, featuring three themed bedrooms, a loft with a large projector screen for movie nights, and a private outdoor retreat with a pool and spacious patio for entertaining with no rear neighbors, creating the perfect setup to attract bookings and memorable guest experiences. Inside, the home offers a spacious open concept layout that connects the living room, dining area, and kitchen, creating an ideal gathering space for families and large groups. The kitchen is fully equipped with stainless steel appliances, granite countertops, a tiled backsplash, and espresso cabinetry, making it both stylish and functional for extended stays. Ceramic tile flooring throughout the main living areas on the first floor provides durability and easy maintenance, ideal for vacation rental use. The first floor features a primary bedroom with direct access to the pool area and a private en suite bathroom complete with a soaking tub and walk in shower. The garage has been converted into a game room with a pool table and foosball table, providing an additional entertainment space that guests love. Upstairs you will find an additional en suite bedroom, four more beautifully furnished bedrooms, and two additional bathrooms. The loft area creates the perfect gathering space and is highlighted by a large projector screen, making it ideal for movie nights, game days, or relaxing after a day at the parks. Step outside to enjoy the covered patio and private pool area, perfect for entertaining or unwinding in the Florida sunshine. With no rear neighbors, the backyard offers added privacy rarely found in vacation homes. Located just minutes from Central Florida’s world famous attractions, shopping, and dining, owners and guests also enjoy access to resort style amenities including a clubhouse, fitness center, resort pool with lazy river, bar, and game room, all within the highly desirable Windsor at Westside Resort. Book your private showing today.

Listing is courtesy of: REAL BROKER, LLC (407-922-8986)

Listing Agent: Brian Hamaoui (407-760-0975)

Remarks: Welcome to 7792 Somersworth Drive in Reunion Resort—a stunning 5-bedroom, 3.5-bath Verona model built in 2023 and offered fully furnished, with the rare flexibility to be used as a short-term rental, long-term rental, or primary residence. Perfectly positioned on an oversized conservation homesite, this premium lot offers peaceful Florida nature views and added privacy—an ideal backdrop for relaxing or entertaining. The extended covered lanai is perfect for grilling and unwinding as you soak in the sunshine before heading out to explore everything Central Florida has to offer. Inside, the thoughtfully designed floorplan features a downstairs primary suite and four additional bedrooms upstairs, making it ideal for larger groups, multi-family stays, or owners seeking space and comfort. Built with numerous upgrades and modern finishes, this home is truly move-in or rent-ready from day one. Located within Reunion, one of Florida’s most sought-after vacation communities, owners and guests enjoy access to championship golf courses, resort pools, water parks, dining, and the iconic rooftop bar atop the Reunion hotel—all just minutes from Walt Disney World, Universal Studios, and the heart of the Orlando tourism corridor. Whether you’re looking for a high-performing vacation rental, a second home, or a primary residence with resort-style living, 7792 Somersworth Drive stands out as one of the best newer construction opportunities in Reunion. Schedule your showing today and see why this home checks every box for lifestyle, location, and investment potential. Sold Fully furnished.

Listing is courtesy of: ORLANDO PROPERTY ADVISORS (407-808-3695)

Listing Agent: Justin Pekarek (407-808-3695)

Remarks: MASSIVE $17,000 PRICE REDUCTION! Rare opportunity alert! Own this stunning 6-bedroom, 5-bathroom masterpiece in the exclusive Paradise Palms Resort for an incredible new price. This 3,291 sq. ft. sanctuary is fully furnished and features the ultimate Kissimmee luxury: NO REAR NEIGHBORS. While others are cramped, you’ll enjoy total privacy just minutes from Disney. From the lagoon-style grotto pool and Tiki Bar to the private cinema, this is the ultimate turn-key investment or dream getaway. At this new price point, it won’t last. VIEWING WINDOW: May 5th-9th, May 17th-28th

Listing is courtesy of: REAL BROKER, LLC (407-922-8986)

Listing Agent: Jason Burke (352-267-7349)

Remarks: PRICE IMPROVEMENT! Experience the best of Florida living in this beautifully maintained pool home featuring a one-of-a-kind custom pool design, updated 2024 exterior paint, and nearly 1,900 square feet of inviting living space surrounded by a true tropical oasis setting. This move-in-ready gem offers the freedom of No HOA living while being just minutes from world-famous theme parks, shopping, dining, and entertainment. Imagine waking up to your own slice of paradise just 15 minutes from Walt Disney World. Imagine picking fresh pineapples from your garden, enjoying sunny afternoons poolside, and ending each day in the privacy and tranquility of one of the areas most established and desirable neighborhoods. Designed for both comfort and entertaining, this warm and welcoming home offers 1,840 square feet of living space — noticeably larger than many comparable 3- or 4-bedroom homes in the area. Built in 1991, the residence features 3 bedrooms, 2 bathrooms, and a spacious 2-car garage. The oversized primary suite serves as a true retreat, complete with direct access to the pool area and a spacious en-suite bath. Multiple living spaces provide flexibility for everyday living and entertaining, including a formal living and dining great room, family room, and an eat-in kitchen. Thoughtful updates include fresh exterior paint completed in 2024 and newly painted pool patio surfaces in 2026. With NO HOA or CDD, you’ll enjoy the flexibility to make this property your own — whether as a primary residence, vacation getaway, second home, or income-producing Airbnb opportunity. Step outside into your private tropical escape, where a custom designed Africa-like shaped pool creates a stunning focal point for unforgettable gatherings and peaceful evenings under the stars. The expansive painted pool deck, elegant paver walkways, mature landscaping, and multiple outdoor entertaining areas create a setting that feels both relaxing and secluded. Pineapple plants throughout the property add a charming tropical touch that perfectly captures the Florida lifestyle. This home has been lovingly maintained with major updates already completed, including a full roof replacement in 2017 (inspected in 2024), water heater (2020), professionally serviced A/C in September 2025, new pool pump (2024), and brand-new LG refrigerator (2025). More than just a home, this is a place to relax, entertain, invest, and create lasting memories, all while enjoying the comfort, privacy, and convenience of a prime Central Florida location. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.

Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)

Listing Agent: Dianna Desboyaux (407-920-4601)

Remarks: Welcome to this spacious and exclusive **3-BEDROOM, 3-BATHROOM condominium** located on the second floor of a resort-style community just 10 minutes from Disney! This unique property features two primary bedrooms with private bathrooms, an open-concept layout connecting the living room, dining area, and kitchen, and a private balcony perfect for relaxing or entertaining. It is the only active property for sale with 3 bedrooms and 3 bathrooms at this price, making it an exceptional opportunity for investment, vacation home, or primary residence. The community offers Resort-style amenities, including a pool, fitness center, tennis court, and more. Enjoy a prime location just minutes from well-known restaurants, shopping, and world-class attractions. **Don’t miss this incredible opportunity for location, space, and value!**

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

Listing Agent: Javier Aparicio (407-346-8319)

Remarks: Short Sale. Short Sale. Third-party lender approval required. Vacant residential townhome sold as-is. Seller and listing broker make no representations or guarantees regarding lender approval or time frame. Buyer to verify all information and conduct due diligence. Nestled in Kissimmee, Florida, is this 3-bedroom, 2.5-bathroom Airbnb-approved townhome offering beautiful views and access to a community pool. Featuring a spacious open-concept living area, a fully equipped kitchen, full-size washer and dryer in a separate laundry room, plus ample storage, this home is perfect for comfortable living, a vacation retreat, or use as a short-term rental. Enjoy a private patio overlooking the lake with shopping, dining, and parks just minutes away. With a motivated seller and priced to sell, this property presents an incredible opportunity for investors and homeowners alike. Don’t miss the chance to make this versatile townhome yours!

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

Listing Agent: Lesly Hijar (321-347-7383)

Remarks: Located on a quiet cul-de-sac in the gated community of Formosa Gardens, this beautiful property 5/3 is a highly successful short-term rental that stays consistently booked and offers a rare opportunity for investors or those seeking a vacation home or primary residence. The home sits on a unique oversized lot featuring a trampoline and soccer field, creating a fantastic outdoor space for families and guests. Recent 2025 upgrades include a NEW 5 TON AC UNIT, new pool pump, and laminated flooring, NEW GAS POOL HEATER (2026). All furniture and household items are included, making this a fully turnkey property ready for continued short-term rental income or personal use. Properties on cul-de-sacs with large lots in Formosa Gardens are rare opportunities. Call today to schedule a showing!

Listing is courtesy of: CSG FLORIDA REALTY, INC. (305-979-7357)

Listing Agent: Cristian Gonzalez (786-390-6471)

Remarks: Location, location, location! On arguably the best lot in the small prestigious gated community of Sunset Lakes, this fully furnished 4-bedroom, 2-bathroom residence offers the best of all worlds, privacy and an open aspect, sunshine and shade, and a lake and conservation outlook. Perfect for Florida living or for a vacation rental. The pool area, with an extended deck and a hot tub/ therapy spa, gets sunshine all day but there is a shaded area close to the house. It is impossible to appreciate these qualities from the street. While the setting is breathtaking, the home itself stands out from the rest with high-value improvements rarely found in this neighborhood. Step inside to discover a residence where no detail has been overlooked. The interior features elegant granite countertops in the kitchen and modernized, upgraded bathrooms that elevate the home well above the standard. For peace of mind and energy efficiency, all windows have been replaced with high-quality double glazing. The heart of the home opens to the private, screened-in pool and luxury above-ground spa, designed for the ultimate Florida lifestyle. The outdoor living space has been significantly enhanced with an upgraded lanai to enjoy outdoor living in all weathers, and an extended deck with patio furniture and a gas grill. The lanai and deck area features additional custom lighting to make evening entertaining comfortable and accessible while you enjoy the peaceful water view. The home is move in ready, and is fully equipped both as a Florida home and as a vacation rental. It is the perfect blend of luxury, location, and extensive upgrades. One of a kind!!!!! Welcome to your dream Florida escape!

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

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

Remarks: This beautifully maintained vacation home in the luxurious Magic Village Resort is an excellent opportunity for short-term rentals when not in personal use. Located in a gated community just minutes from major theme parks, shopping, and dining, it offers the perfect setting for enjoying time with family and friends, combining resort-style amenities with the privacy of a home. The property features a gourmet kitchen with stainless steel appliances, granite countertops, and solid wood cabinetry. Just off the family room, you’ll find a patio with an outdoor barbecue area, and dining space—ideal for entertaining. Upstairs, there are three spacious bedrooms and a private balcony, perfect for relaxing and unwinding. The home is fully furnished and professionally decorated, making it truly move-in or rental ready. This is a great opportunity at an attractive price point.

Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)

Listing Agent: Adrian Antunes, Sr (857-343-9065)

Remarks: Welcome to 7755 Grassendale Street! This TURNKEY, well-maintained 4-bedroom, 4-bath home is move-in ready and ideal as a primary residence or short-term vacation rental. The open-concept layout features a large foyer, spacious dining area, family room, and a well-appointed kitchen with stainless steel appliances, granite countertops, breakfast bar, and nook. All bedrooms feature luxury vinyl plank flooring and are tastefully themed, while the main living areas are tile. The converted 2-car garage (2021) is air-conditioned and serves as an entertainment space with a home theater, gaming consoles, and a sit-down arcade game. Step outside to the covered lanai and enjoy the refurbished (2022) pool and spa—perfect for relaxing in the Florida sun. The community offers a 24-hour guard-gated entrance and resort-style amenities, including a 10,000 sq. ft. clubhouse, lagoon-style pool with water slides, fitness center, movie theater, sports courts, playground, and walking trail. Conveniently located minutes from Disney, with dining, shopping, and everyday essentials nearby. This truly is a MUST SEE home!

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

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

Remarks: Welcome to the Epic Universe House! Experience a truly immersive vacation lifestyle in this stunning 8-bedroom, 6-bathroom pool home located in the gated community of Windsor at Westside. Fully themed, recently renovated, and professionally designed, this turn-key residence pays tribute to the highly anticipated Epic Universe, featuring an arcade, a Nintendo World gaming room, and immersive themed bedrooms including Harry Potter, How to Train Your Dragon, Legend of Zelda, and more! Spanning over 4,000 sq ft, this spacious retreat perfectly blends modern elegance with family entertainment. The open-concept first floor features ceramic tile flooring, a chef’s kitchen with granite countertops, and an oversized island designed for large gatherings. Step outside to your private outdoor oasis—a screened-in lanai with a sparkling pool and spa overlooking a serene water view. Recent Upgrades: This home is being sold AS-IS and Fully Furnished, featuring high-end furniture and professional decor. It is a proven, high-performing vacation rental with a history of top-tier reviews making it the perfect addition to any investment portfolio. World Class Resort Amenties: Living in Windsor at Westside provides 24/7 gated security and access to a 10,000 sq ft clubhouse including: Resort-Style Pool & Interactive Splash Park, Winding Lazy River & Water Slide, State-of-the-Art Fitness Center, Tu Casa Bar & Lounge / Poolside Tiki Bar, Arcade Game Room, Multi-purpose Sports Courts, & Sand Volleyball, Sundry Shop & Playground Unbeatable Location: Located just minutes from Walt Disney World, Universal Orlando Resort, and the newly opened Epic Universe park, you are at the heart of Central Florida’s top attractions, world-class dining, and premium shopping. Don't miss the chance to own a piece of the magic! Schedule your private showing today and step into a world of epic possibilities.

Listing is courtesy of: PABLA PROPERTIES (407-967-2757)

Listing Agent: Sunny Pabla (407-967-2757)

Remarks: 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!

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Katie Bray (407-779-6677)