Kissimmee Single Family Homes For Sale - 2003 homes

Remarks: Welcome to tastefully designed 5/bed 4/bath home with private pool facing conservation area in the prestige Community Windsor at Westside, zoned for short term vacation rental. The open floor plan seamlessly connects the living, dining, and kitchen areas, perfect for everyday living and entertaining. There is a master bedroom on the first floor and upstairs you’ll find another spacious master bedroom and additional bedrooms for privacy and comfort. Residents can enjoy world-class resort amenities, including an 8,000 sq. ft. clubhouse, heated pool, lazy river, spa, volleyball and basketball courts, and on-site restaurant and bar. The home is just minutes from Disney Parks and other Orlando attractions.

Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)

Listing Agent: Eileen Li (407-765-2589)

Remarks: Welcome to this immaculate 3-bedroom, 2-bath home nestled in the Creekside at Boggy Creek community. Thoughtfully designed with both comfort and style in mind, this residence features an open and bright kitchen that seamlessly overlooks a spacious dining area. Rich in character and complemented by modern finishes, the home offers a warm yet contemporary feel throughout. Step outside to enjoy the paved back patio and fully fenced yard, creating a private outdoor space ideal for relaxing or hosting guests. The primary suite is complete with a well-appointed ensuite bathroom and a generously sized walk-in closet. Additional bedrooms provide flexibility for family, guests, or a home office. This home combines functionality, charm, and privacy.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Kevin Kendrick (407-271-1854)

Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. “Sold As-Is and now offered at an improved price, presenting an exceptional opportunity to own this move-in ready home.” Price recently reduced! Move-in ready and beautifully maintained 4-bedroom, 2-bath home located in a beautiful neighborhood. This inviting residence has been freshly painted and features updated bathroom cabinetry, creating a clean and modern feel throughout the home. The thoughtfully designed floor plan offers comfortable living spaces that are perfect for both everyday living and entertaining. The property has been well cared for and is ready for its next owners to make it their own. Residents enjoy access to wonderful community amenities including a clubhouse, swimming pool, and sports areas—perfect for an active and social lifestyle. Conveniently located near shopping, dining, schools, and everyday conveniences, this home offers both comfort and accessibility. This property is being sold as-is and presents a fantastic opportunity at a newly reduced price. Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Rana Al Jallad (321-999-4937)

Remarks: Price reduced! Seller motivated. Spacious 5 bedroom 3 bath home located in The Oaks. Features a freshly painted exterior and a functional layout ideal for everyday living. Located near shopping center, dining and major roadways. Easy access to local amenities.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Katya Rivera Torres (407-967-8823)

Remarks: Don't miss the opportunity to acquire this solid revenue producing tri-plex with three separate units! Each unit has two bedrooms and one bathroom. Units are consistently leased by tenants. Roof replacement and exterior re-paint completed in the last few years. The property has a small exterior storage room to store supplies or materials. Professional property management services are already in place which would provide for a smooth transition in operations for new ownership. One of the three units in this building was just renovated! No CDD or HOA fees! This unit is being sold in unison with parcel# 15-25-29-1570-0001-0380. Don't miss the chance to add these well established investment properties to your portfolio!

Listing is courtesy of: VALIANT REALTY GROUP LLC (407-654-0041)

Listing Agent: Lorenzo Clark (407-968-3180)

Remarks: Don't miss the opportunity to acquire this solid revenue producing tri-plex with three separate units! Each unit has two bedrooms and one bathroom. Units are consistently leased by tenants. Roof replacement and exterior re-paint completed in the last few years. The property has a small exterior storage room to store supplies or materials. Professional property management services are already in place which would provide for a smooth transition in operations for new ownership. No CDD or HOA fees! This unit is being sold in unison with parcel# 15-25-29-1570-0001-0355. Don't miss the chance to add these well established investment properties to your portfolio!

Listing is courtesy of: VALIANT REALTY GROUP LLC (407-654-0041)

Listing Agent: Lorenzo Clark (407-968-3180)

Remarks: Welcome to this charming 4-bedroom, 2-bath home offering 1,874 square feet of comfortable living space. Designed with both relaxation and entertaining in mind, this home features an open-concept layout that seamlessly connects the kitchen, dining, and living areas. Natural light fills the space, creating a warm and inviting atmosphere throughout. Situated on a spacious lot with a peaceful pond view, you’ll enjoy a serene backdrop right from your backyard. The primary suite includes a walk-in closet and a private en-suite bathroom, providing a perfect retreat at the end of the day. Blending functionality with a touch of nature, this home is ideal for everyday living and ready for its next owner to move right in.

Listing is courtesy of: CENTRIC REALTY SERVICES LLC (407-421-9391)

Listing Agent: Jean Julme (321-280-0658)

Remarks: Under contract-accepting backup offers. Waterfront home in Shingle Creek Reserve, where Florida living meets comfort and convenience. Bring your boat and enjoy direct access to Lake Tohopekaliga through the community boat ramp—or if you prefer, bring your clubs and play on, The Oaks National, Golf Course! Perfect home for weekends on the water or the on the golf course. This centrally located home offers easy access to major theme parks, popular attractions, the MCO Airport, shopping, dining, and more. Inside, the well-designed floorplan is ideal for entertaining. The living and dining rooms feature large windows that fill the home with natural light, creating a warm, open atmosphere. The kitchen overlooks the main living areas and is equipped with stainless steel appliances, granite countertops, a tile backsplash, and a spacious island with a built-in sink. The first-floor primary suite offers tranquil water views and charming architectural details including wood flooring, tray ceiling, crown molding, and carved accents. The expansive primary bath includes his-and-her vanities, a soaking tub, standalone shower, and separate walk-in closets. All bedrooms have been upgraded with wood flooring. Upstairs, a generous den provides the perfect space for a home office or relaxation area. Sliding doors lead to a private balcony overlooking the large backyard, serene water views, and the golf course—an ideal spot for morning coffee or winding down at the end of the day. Low monthly HOA fee covers boat ramp, walking trails, basketball courts, and a playground. This stunning home offers the best of both comfort and lifestyle—schedule your private viewing today!

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

Listing Agent: Alexis Mckenzie (321-438-9670)

Remarks: Under contract-accepting backup offers. Welcome to this fabulously positioned 4-bedroom, 2-bathroom pool home in the highly sought-after Lake Berkley Resort. This beautiful home offers 1,960 sq ft of living space, which combines comfort, location, and investment potential , all in one fantastic opportunity. This home is being sold fully furnished, and showcases stylish, modern décor with a neutral color palette, creating a bright, airy, and inviting space that appeals to both homeowners and vacation guests alike and allows for a seamless, turnkey transition for short-term rental or personal use. From the moment you step inside, you are drawn to the stunning water views. The kitchen and main living areas are designed to maximize natural light and flow seamlessly out to the pool deck, while bedrooms also enjoy views of the pool and lake beyond—creating a bright, open, and relaxing atmosphere throughout the home. Step outside to your private pool and spa, the perfect place to unwind at the end of the day—whether you're enjoying your morning coffee, soaking in the spa at sunset, or simply watching wildlife play across the water. This home truly captures the Florida lifestyle, blending indoor-outdoor living with peaceful lakefront scenery. Located within a 24-hour guard-gated community, Lake Berkley is one of Central Florida’s most popular short-term rental destinations. Its prime location places you just minutes from world-famous attractions, Disney, shopping, dining, and entertainment, making it highly desirable for vacationers year-round. Residents and guests enjoy a wide range of resort-style amenities, including a clubhouse with fitness center, community pool, playgrounds, tennis and basketball courts, and scenic walking trails around the lake. Whether you’re looking for a primary residence, second home, or a high-performing short-term rental investment, this property offers incredible versatility in a proven vacation hotspot. Must be seen to appreciate!!! PRICED TO SELL!

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

Listing Agent: Aimee Brierley (407-717-0592)

Remarks: Absolutely stunning and thoughtfully designed, this exceptional home offers the perfect blend of elegance, functionality, and comfort. Featuring 4 spacious bedrooms and 3 full bathrooms, plus two additional versatile rooms, this residence is ideal for both everyday living and entertaining. Upstairs, you’ll find all 4 bedrooms and 2 bathrooms, including a beautifully positioned owner’s suite that enjoys ultimate privacy, set apart from the other bedrooms by a uniquely designed hallway. A charming mezzanine overlooks the main living areas, creating an open and airy feel while adding architectural interest. The second floor also offers flexible space on either side of the hallway—perfect for small home offices, study nooks, or a gaming area. Downstairs, two additional rooms and a full bathroom provide incredible flexibility, ideal for a guest room, home office, or flex space to fit your needs. The home showcases unique craftsmanship throughout, with custom wall moldings and detailed design elements in the living areas, handcrafted by the owners, adding a nice upscale touch. Step outside to your private backyard oasis, where a stunning pool with an attached jacuzzi invites you to relax and unwind. The spacious outdoor area is perfect for hosting family gatherings and entertaining guests year-round. Additional features include fully paid-off solar panels, a water softener system, and a fairly new water heater—providing both efficiency and peace of mind. Located in one of the few communities in the area with no HOA, this property offers both freedom and convenience. Just minutes from major parks, attractions, shopping, and dining, this home is truly move-in ready and a rare find.

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

Listing Agent: Silma Santiago (407-552-2246)

Remarks: Experience the ultimate vacation retreat and investment opportunity at 1576 Nassau Point Trail in the highly sought-after Solara Resort! This stunning 9-bedroom, 6.5-bath fully furnished pool home generated over $100,000 in rental income from Jan 2025–Jan 2026 and is completely turn-key and rental ready. Built in 2019, the home features an upgraded luxury furniture package, private movie theater, spacious game room loft, custom bar area, themed bedrooms, and expansive open-concept living spaces designed for unforgettable guest experiences. Step outside to your private screened-in oasis featuring a sparkling pool, spa, and extended sun deck — perfect for relaxing after a day at the parks. Located just minutes from Walt Disney World and Orlando’s top attractions, this property offers both luxury and convenience. Owners and guests enjoy access to Solara Resort’s incredible world-class amenities including the FlowRider® surf simulator, resort-style heated pool, splash pad, fitness center, sports courts, on-site dining, and 24/7 gated security. Whether you're looking for a high-performing short-term rental investment or a dream vacation home, this exceptional property checks every box!

Listing is courtesy of: HOLIDAY REALTY LLC (321-278-5486)

Listing Agent: Bryan Rogers (321-278-5486)

Remarks: Welcome to an extraordinary luxury vacation residence in the highly sought-after Sonoma Resort at Tapestry, where sophisticated modern design meets exceptional short-term rental potential. Perfectly positioned with tranquil water views at the front, this professionally curated home delivers a true resort-style experience just minutes from Disney, world-class dining, shopping, and Orlando’s premier attractions. Designed for both elegance and functionality, the home showcases expansive open-concept living spaces enhanced by sleek tile flooring throughout all common areas — completely free of carpet in the main living spaces for a refined aesthetic and easy maintenance. The chef-inspired kitchen seamlessly flows into the oversized dining and gathering areas, creating the ideal setting for entertaining large groups and luxury vacation stays. Every detail of this residence has been thoughtfully elevated, from the designer lighting and upscale finishes to the spectacular themed entertainment spaces that set this property apart from the competition. Multiple immersive themed bedrooms create unforgettable guest experiences, while the custom game rooms and private theater-style entertainment areas offer resort-level amenities rarely found in comparable properties. The beautifully designed themed suites provide both visual impact and strong guest appeal, making this home exceptionally attractive for high-performing vacation rental income. Step outside to your private screened pool and outdoor living area, offering the perfect Florida retreat for relaxation and entertaining year-round. Whether utilized as a primary residence, second home, or income-producing investment property, this exceptional home combines luxury, location, and proven vacation-rental desirability in one of Central Florida’s premier resort communities.

Listing is courtesy of: INTEREALTY SERVICE (626-328-8535)

Listing Agent: Emma Yue (626-328-8535)

Remarks: Welcome to this spacious 3 bedroom, 2 bathroom home offering 2,609 sq ft of comfortable living space. The home features a well-designed layout with expansive living and dining areas that flow into the kitchen, creating an ideal setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Outside, enjoy a nicely sized yard with room to relax or personalize. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.

Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)

Listing Agent: Raul Pino (305-662-1502)

Remarks: Turnkey investment opportunity in a highly sought-after resort-style community just minutes from Disney World! This fully furnished home is a heavily booked short-term rental with strong income potential and future bookings in place. Designed to stand out, the property features themed rooms including a Frozen-inspired bedroom and a Star Wars-themed room with immersive LED lighting, creating a memorable guest experience that drives repeat bookings. The garage has been professionally converted into a game room, perfect for entertainment and maximizing rental appeal. Recent updates include new vinyl flooring in the loft, adding a fresh, modern touch to the living space. The open layout, spacious bedrooms, and private accommodations make this home ideal for large groups and vacationing families. Located just minutes from world-class attractions, dining, and shopping, this property offers both a fantastic personal getaway and a income-producing asset. Bookings, financials, and rental history available upon request!

Listing is courtesy of: SPECTRUM GLOBAL REALTY, INC (407-770-0067)

Listing Agent: Nisha Mehta (407-462-9297)

Remarks: One or more photo(s) has been virtually staged. Experience an unparalleled lifestyle in this stunning waterfront home, where breathtaking views and thoughtfully designed living spaces come together seamlessly. This exquisite property features 3 spacious bedrooms, 3 modern bathrooms, and a versatile den/study, making it ideal for both everyday living and entertaining. As you arrive, you’re welcomed by an elegant screened courtyard with custom double leaded glass entry doors, setting a sophisticated tone from the very beginning. Inside, the home showcases a seamless blend of style and comfort with ceramic tile and luxury vinyl plank flooring throughout the main living areas. The expansive great room is a true centerpiece, offering panoramic water views and abundant natural light that create a warm, inviting atmosphere. The gourmet kitchen is a chef’s dream, featuring Beautiful tile backsplash, Stainless steel appliances, Spacious eat-at bar, Ample cabinetry and counter space and Upgraded lighting. Adjacent to the kitchen, the dining area continues the experience with picturesque waterfront views, making every meal feel extraordinary. The primary suite is a private retreat, complete with a cozy sitting area, two large walk-in closets, and a luxurious en-suite bath featuring a custom walk-in shower. For added flexibility and privacy, the home includes a separate casita/in-law suite located across the courtyard—perfect for guests or extended family or a craft room. Step outside to your covered and extended screened lanai, where you can relax, entertain, and enjoy serene water views and stunning sunsets year-round. Additional highlights include 2-car garage with ample storage, Extra-large laundry room with utility sink, New roof (2023), New HVAC for casita (2023), Main HVAC updated (2017),and a water softener system. This exceptional waterfront property offers the perfect blend of luxury, comfort, and functionality—your private oasis awaits. Solivita is a premier 55+ community, offering residents an exceptional lifestyle with state-of-the-art amenities. Enjoy 2 fully equipped fitness centers, dance and aerobics studios, and an impressive array of recreational options including 14 heated swimming pools, two heated spas, tennis courts, pickleball courts, shuffleboard, bocce ball, billiards, and an art gallery. The community also features three on-site restaurants and two championship 18-hole golf courses. With a full calendar of activities and events, there’s always something new to explore and enjoy. This home is conveniently located near a hospital and medical office complex, and shopping center.

Listing is courtesy of: PELLEGO, LLC (561-414-4614)

Listing Agent: Stan Wilson (850-496-3424)

Remarks: Priced to Sell! Motivated Seller! Stunning 6BD/4.5BA villa, professionally designed, truly a gem at this price! Fully furnished and ready to generate attractive short-term rental income. Enjoy a private pool, modern layout, and access to Solara Resort’s top-tier amenities, heated pool, surf simulator, gym, bar & grill, and more. HOA includes internet, landscaping, and full access to resort perks.

Listing is courtesy of: SINGULAR REALTY LLC (407-999-6899)

Listing Agent: Juliana Martins (786-546-6195)

Remarks: Under contract-accepting backup offers. NO HOA... Be prepared to be impressed with the upgrades inside this home located in The Oaks at Mill Run Subdivision. Beautifully upgraded 3-bedroom, 2-bath home with a 2-car garage and a private pool, thoughtfully renovated with over $100,000 in improvements! This property features a complete 2023 upgrade package, offering modern finishes and peace of mind for the next owner. Enjoy elegant porcelain tile flooring throughout, along with new doors and windows that enhance both style and energy efficiency. The home boasts a fully updated interior, including new cabinetry, quartz countertops throughout, and all-new appliances.Additional upgrades include modern light fixtures, a new A/C system, and a new water heater, ensuring comfort and efficiency year-round. Step outside to your private oasis featuring a beautiful resurfaced pool with updated equipment, a covered patio/lanai, and a built-in grill, perfect for entertaining. The extended paver driveway adds both convenience and curb appeal.The home also includes a newer roof with added insulation, fenced backyard, new gutters, and upgraded bathroom and kitchen vents for improved functionality.Bonus opportunity: The seller is offering the option to purchase the home fully furnished, with furniture valued at up to $20,000—making this a perfect move-in ready or turnkey investment opportunity.This property truly combines quality, style, and value, don’t miss your chance to own this exceptional home!

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

Listing Agent: Monique Morgan (321-443-5328)

Remarks: Welcome to a truly unparalleled luxury estate, nestled on 5 acres of serene privacy. This custom-built masterpiece, completed in 2009, boasts an impressive 11,138 square feet of meticulously designed living space, where every detail has been thoughtfully curated for the discerning homeowner. As you enter through the private gate, you are greeted by a stunning family room featuring a handcrafted stone gas fireplace and soaring ceilings that create an inviting atmosphere. The elegant curving marble staircase, adorned with a magnificent Swarovski crystal chandelier, sets the tone for the opulence that awaits. This estate offers 5 spacious bedrooms, each with large walk-in closets and en-suite bathrooms, ensuring comfort and privacy for family and guests alike. The main living areas are enhanced by exquisite woodwork, including a gorgeous dining room and a living room that seamlessly connects to the outdoor oasis through sliding glass doors that open at the corner, perfect for entertaining. Indulge in the ultimate entertainment experience in the media room, complete with luxurious seating and a stunning chandelier commissioned from Tiffany's in New York. The primary suite is a true retreat, featuring a cozy sitting area and an expansive closet. Additional highlights include a gym with a steam room, an office/study/library, and an upstairs game room that overlooks a spacious covered balcony. The outdoor amenities are equally impressive, featuring a large pool with a spa, ample undercover seating, an outdoor kitchen, and tennis courts, all surrounded by lush landscaping and majestic oak trees. The estate also includes a wine cellar, a wet bar with custom woodwork, and coffered ceilings adorned with unique prints. With a 4-car side garage and an attention to detail that is truly one of a kind, this estate is unlike anything you have ever seen. Experience luxury living at its finest—schedule your private tour today and discover the extraordinary lifestyle that awaits you.

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Brian Hyser (407-951-2472)

Remarks: Discover this exceptional, fully furnished 8-bedroom, 7-bathroom luxury home located in the highly sought-after Encore Resort at Reunion—a premier vacation home community just minutes from Walt Disney World. This spacious residence features an open-concept living, dining, and kitchen area with granite countertops and solid wood cabinetry throughout, creating an inviting space for large gatherings. The thoughtfully designed layout includes two bedrooms on the first floor, one with an en-suite bath, while the second level offers an additional living area and six more bedrooms, including two primary suites, two bedrooms connected by a Jack & Jill bath, and the remainder with private en-suites. Entertainment is at the forefront with a fully converted game room in the garage featuring table tennis, shuffleboard, mini basketball, a card table, and a TV. Step outside to your private oasis complete with a heated pool and spa, covered patio dining area, grill, and lounge seating—perfect for enjoying the Florida sunshine. As part of Encore Resort, guests and owners enjoy access to a 10-acre private water park with thrilling slides, a lazy river, and splash zones, along with on-site dining, fitness facilities, sports courts, arcade, and daily activities, making this property a true resort-style experience. Whether you're seeking a turnkey investment or a luxurious vacation retreat, this home delivers the ideal blend of comfort, entertainment, and location.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Frank Baloun (407-488-4969)

Remarks: Indulge in Luxury Living at Encore Reunion! Welcome to this stunning 2-story home, located in the exclusive, sought-after community of Encore at Reunion. Renowned for its private waterpark and world-class amenities, Encore is the ideal place for relaxation and adventure. Nestled on THE LARGEST LOT in the community, this Grand Pool home offers the perfect balance of comfort and excitement. Boasting 8 spacious bedrooms and 7 full bathrooms, this expansive fully furnished residence provides ample space for family, guests, or business use. The state-of-the-art kitchen features top-tier appliances, while the generously sized living areas and cozy bedrooms ensure guests experience ultimate comfort. On the first floor, two beautifully designed rooms serve as either guest accommodations or private offices. The second floor features a large loft area that leads to five additional rooms, in addition to its luxurious primary bedroom suite that offers a serene retreat. Every corner of this home has been thoughtfully designed for both style and comfort. Recently updated, the home showcases a fresh, clean look with a new coat of paint that brightens the interior. Plush new carpeting throughout the bedrooms adds warmth and coziness, while ceiling fans improve airflow and enhance the modern aesthetic. The oversized, fully fenced lot boasts a private pool and ample yard space, ideal for a wide range of outdoor activities or enjoyable family game time. The garage has been upgraded with durable epoxy flooring and an AC unit, making it perfect for storage or as a versatile workspace. The new HVAC system ensures efficient climate control for year-round comfort. Beyond its luxurious features, this property also represents an exceptional investment opportunity. Located within an approved short-term rental community, this fully furnished home is perfectly positioned to succeed in the short-term rental market. Whether you're looking to generate income or provide guests with an unforgettable stay, this home is an ideal choice. Guests will love the convenient access to local cafes, restaurants, shopping, and entertainment, including parks and theaters. Encore at Reunion offers premier facilities and top-notch security, providing peace of mind for both residents and renters alike. With outstanding potential for strong returns on investment, this property is ready to start earning immediately. Don’t miss out on this incredible opportunity!

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Christina Laidley (954-579-3742)