Kissimmee Homes For Sale & Real Estate - 3271 homes

Remarks: Experience luxury living in the premier gated community of Tapestry! This stunning residence at 3020 Cardillino Way offers the perfect blend of modern elegance and resort-style comfort. From the moment you arrive, you’ll be captivated by the curb appeal and meticulously maintained surroundings. Inside, the home features a spacious, open-concept floor plan designed for contemporary living, boasting abundant natural light and high-end finishes throughout. The gourmet kitchen serves as the heart of the home, flowing effortlessly into the expansive living and dining areas—ideal for hosting family and friends. Living in Tapestry means more than just a beautiful home; it’s a lifestyle. Residents enjoy exclusive access to world-class amenities, including a zero-entry sparkling pool, a splash pad, a state-of-the-art fitness center, a grand clubhouse, dog parks, and scenic walking trails. Strategically located just minutes from The Loop, you’ll have premier shopping, dining, and entertainment right at your doorstep. With quick access to the Florida Turnpike and Osceola Parkway, you are perfectly positioned for a short commute to Orlando International Airport and all major theme parks. Whether you are looking for a forever home or a high-end investment, this property is a must - see. Schedule your private tour today and start living the Tapestry lifestyle!

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Luceyda Rodriguez Otero (407-301-8394)

Remarks: Under contract-accepting backup offers. Two screened outdoor living spaces and a large fenced backyard make this Kissimmee home stand out. This well maintained 2 bedroom, 2 bathroom property offers approximately 1,200 square feet of comfortable living space with durable tile flooring throughout and a bright, functional layout. Enjoy relaxing or entertaining in the screened porch or the additional screened patio, both perfect for enjoying the Florida breeze year round. The spacious 0.18 acre lot provides a large backyard with plenty of room to gather, garden, or create your own outdoor retreat, plus a storage shed for added convenience. The garage has also been screened, creating a versatile bonus space that works well as a hangout area, hobby space, or additional storage. A wide driveway and welcoming front entry add to the home's appeal. Conveniently located near shopping, dining, and major roadways, this property offers comfort, flexibility, and easy maintenance. Schedule your private showing today.

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

Listing Agent: Gissel Ortega (646-512-2581)

Remarks: Spacious and versatile 4-bedroom, 2-bathroom pool home located in the established Lindfields community, just minutes from Walt Disney World and the shopping, dining, and entertainment along US-192. A new roof was installed in 2020 and the property was just refurbished including interior paint, exterior paint, pool deck painted, luxury vinyl flooring installed throughout the property, new light fittings and a new roof 2020. Positioned toward the rear of the neighborhood, this community benefits from good sized lots and a floor plan offering over 2,000 sq ft of well-designed living space. No HOA—one of the few communities in the area - offers home owners unrivaled flexibility. The home features a bright and open layout filled with lots of natural light, including a large living and dining room with sliding doors leading to the pool deck, a separate family room, and a breakfast nook with sliding patio doors offering additional pool deck access. The spacious kitchen includes a breakfast bar and ample cabinetry, ideal for both everyday living and entertaining. A split floor plan provides privacy, with a generously sized primary suite offering dual sinks, a garden tub, and separate shower. The house bathroom also includes direct pool access for added convenience. Step outside to enjoy a private fenced yard and expansive south facing L-shaped pool deck—perfect for relaxing, entertaining, or enjoying the Florida lifestyle. Zoned for short-term rental, this home is ideal as a primary residence, vacation home, or income-producing investment in a prime Central Florida location.

Listing is courtesy of: RE/MAX HERITAGE (863-424-2309)

Listing Agent: Steven Silcock (407-574-0218)

Remarks: Fully upgraded from floor to ceiling, this luxury townhome blends contemporary elegance with high-end functionality — designed specifically for short-term rental success. Located in the exclusive Doppio Westside community in Kissimmee, just 15 minutes from Walt Disney World, this 5-bedroom, 4.5-bath home features an open-concept layout with spacious integrated living, dining, and kitchen areas that flow seamlessly to your own private heated pool. The kitchen is a showstopper with two oversized islands, Level 5 quartz countertops, designer backsplash, slatted wood detail, and Whirlpool stainless steel appliances. All cabinetry throughout the home includes soft-close features and matte hardware for a sleek, modern finish. Each of the five bedrooms is designed with comfort and rental flexibility in mind — including four full en-suites and one located on the first floor. The bathrooms are finished with high-end porcelain tile, glass shower enclosures, built-in niches, and vessel sinks in select locations. Luxury vinyl plank flooring runs throughout the entire home — no carpet anywhere — and 5.5" square baseboards give a clean, elevated look. Additional features include PVC windows, a smart front door lock, a lockable owner’s closet, a hybrid water heater, thermostat, and 2 Car Parking Spot. Construction is full concrete block, including second floor, with an insulated "sandwich" roof system and rubber membrane roofing designed for durability and energy efficiency. Located within a gated community, Doppio Westside offers resort-style amenities such as a lagoon-style pool, full-service restaurant, clubhouse with front desk concierge, fitness center, playground, convention center, and EV charging stations — all exclusively zoned for short-term rental with no public school restrictions. Don't miss this opportunity to invest in one of Central Florida’s most unique STR communities — fully upgraded as standard, and built with both guest experience and investor return in mind.

Listing is courtesy of: INVESTOR'S REAL ESTATE LLC (407-688-4355)

Listing Agent: Maria Bandarra (407-414-4592)

Remarks: Fully upgraded from floor to ceiling, this luxury townhome blends contemporary elegance with high-end functionality — designed specifically for short-term rental success. Located in the exclusive Doppio Westside community in Kissimmee, just 15 minutes from Walt Disney World, this 5-bedroom, 4.5-bath home features an open-concept layout with spacious integrated living, dining, and kitchen areas that flow seamlessly to your own private heated pool. The kitchen is a showstopper with two oversized islands, Level 5 quartz countertops, designer backsplash, slatted wood detail, and Whirlpool stainless steel appliances. All cabinetry throughout the home includes soft-close features and matte hardware for a sleek, modern finish. Each of the five bedrooms is designed with comfort and rental flexibility in mind — including four full en-suites and one located on the first floor. The bathrooms are finished with high-end porcelain tile, glass shower enclosures, built-in niches, and vessel sinks in select locations. Luxury vinyl plank flooring runs throughout the entire home — no carpet anywhere — and 5.5" square baseboards give a clean, elevated look. Additional features include PVC windows, a smart front door lock, a lockable owner’s closet, a hybrid water heater, thermostat, and 2 Car Parking Spot. Construction is full concrete block, including second floor, with an insulated "sandwich" roof system and rubber membrane roofing designed for durability and energy efficiency. Located within a gated community, Doppio Westside offers resort-style amenities such as a lagoon-style pool, full-service restaurant, clubhouse with front desk concierge, fitness center, playground, convention center, and EV charging stations — all exclusively zoned for short-term rental with no public school restrictions. Don't miss this opportunity to invest in one of Central Florida’s most unique STR communities — fully upgraded as standard, and built with both guest experience and investor return in mind.

Listing is courtesy of: INVESTOR'S REAL ESTATE LLC (407-688-4355)

Listing Agent: Maria Bandarra (407-414-4592)

Remarks: Welcome to this fully furnished 3-bedroom, 3-bathroom townhome nestled in the gated community of Crestwynd Bay. This move-in-ready home offers a durable tile roof, a private concrete patio, and the rare bonus of no rear neighbors—just peaceful green conservation views for added privacy and tranquility. Inside, you'll find a spacious layout perfect for personal use or short-term rental. The HOA includes exterior maintenance, basic cable, internet, trash service, and access to community amenities like a pool and playground. Ideally located just minutes from Walmart, Disney World, and major resorts, with quick access to I-4, Osceola Parkway, Highway 192, and the 429 toll road, this home offers both comfort and convenience. Whether you're seeking a primary residence, vacation retreat, or investment property, this townhome delivers value and location in one.

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Naf Zaman (407-580-5483)

Remarks: Stunning 2-bedroom, 2-bath condominium with 1-car garage! This beautifully maintained home offers a bright and airy open-concept design, perfect for both everyday living and entertaining, ideally located next to the community clubhouse, offering easy access to amenities and enhancing your lifestyle. Enjoy two spacious master suites, each featuring its own walk-in closet, providing comfort, privacy, and flexibility. Elegant laminate flooring flows seamlessly throughout the entire home, creating a modern and cohesive feel. The kitchen is equipped with a gas stove, perfect for those who love to cook, and features recent upgrades including a brand-new refrigerator (2025), new microwave (2025), and new garbage disposal (2025). The A/C unit was replaced in 2019. Additional highlights include a convenient inside laundry room and a well-designed layout that maximizes both space and functionality. This move-in ready condo offers the perfect combination of style, comfort, and low-maintenance living—a true must-see!

Listing is courtesy of: THE EXPERTS TEAM REALTY INC (407-674-7994)

Listing Agent: Reyna Quezada (407-780-0426)

Remarks: Your Private Oasis Awaits at the fantastic Windsor at Westside Resort community. Step into luxury and leisure of this fully furnished 6-bedroom, 4.5-bathroom retreat nestled in one of Central Florida’s most sought-after vacation communities. Designed for comfort and entertainment, this spacious home features a stunning loft, soaring ceilings, and an open-concept layout that seamlessly blends elegance with functionality. It features a private heated south facing pool and spa for year-round relaxation, an expansive covered lanai with sun loungers and patio seating, a gourmet kitchen with stainless steel appliances and generous counter space and a breakfast bar, dual master suites, one on each floor making it ideal for guests or multi-generational living, a converted garage game room for added fun and entertainment, and stylish finishes throughout, including ceramic tile and plush carpeting. Recent upgrades include a brand-new AC compressor and brand-new dryer. The resort features lots of great amenities including a lazy river, splash pool, clubhouse bar, fitness center, and game room. The community is guard gated and the HOA includes cable, internet, and grounds maintenance. All this and just minutes from world-famous attractions, shopping, and dining, this property offers the perfect blend of convenience and escape. Whether you're seeking a second home, a vacation getaway, or a high-performing short-term rental, this residence delivers exceptional value and unforgettable experiences.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ping Ma (863-332-0298)

Remarks: Welcome to Windsor at Westside! This stunning 5-bedroom, 4.5-bathroom townhome is beautifully decorated and comes fully furnished with top-of-the-line model home furniture. Zoned for short term rental this fantastic vacation home is the perfect investment property or second home. The home features open floor plan and a fantastic kitchen with granite countertops, 42-inch cabinets and stainless-steel appliances. It boasts spacious living spaces, a lovely covered lanai and screened in private swimming pool. Windsor at Westside Resort provides one of a kind amenities including an 8,000 square foot resort-style clubhouse with a huge heated pool, a spa, and a lazy river as well as a recreation center, poolside cabana, playground, volleyball, tennis, and basketball courts and a game room, restaurant, bar, and relaxing lounge area with indoor/outdoor fireplace! The community is just minutes to Disney World and all the other famous attractions!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ping Ma (863-332-0298)

Remarks: Check out this beautiful 5-bedroom, 4-bathroom pool home in the highly sought after resort community of Windsor at Westside! This fully furnished home is in great condition and it's just minutes from Disney and Orlando’s iconic attractions. Designed with gatherings in mind, this home boasts an open-concept layout featuring a generous family room and oversized dining area, perfect for entertaining or hosting extended family vacations. The modern kitchen impresses with 42" cabinets, stainless steel appliances, stone countertops, and a breakfast bar ideal for casual meals. Step through the sliding doors to your private outdoor paradise, a west-facing heated pool that basks in afternoon sun, complete with a brick-paver deck and covered lanai for all-weather relaxation. Inside, the home comes tastefully furnished with a stylish, turn-key décor. A converted garage adds a bonus game room to the already expansive layout, ensuring fun and comfort for every guest. Windsor at Westside offers a gated, amenity-rich lifestyle with a resort-style clubhouse, heated pool and spa, lazy river, splash pad, fitness center, arcade, sand volleyball, tennis and basketball courts, and an on-site restaurant and bar.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ping Ma (863-332-0298)

Remarks: Under contract-accepting backup offers. Great Investment Opportunity in Poinciana! Spacious 3-bedroom, 2-bath home offering 1,279 sq. ft. of living space and excellent potential. Features include stainless steel appliances, an oversized Florida Room, and a primary suite with walk-in closet. Enjoy a large fenced yard with mature trees providing privacy and outdoor space. Home needs some TLC—perfect for investors or buyers looking to add value. Conveniently located near shopping, hospitals, and major highways.

Listing is courtesy of: CENTURY 21 CARIOTI (407-354-0074)

Listing Agent: Luis Talavera (863-368-7289)

Remarks: Imagine waking up to peaceful conservation views in one of The Oaks' most desirable communities. This 4-bedroom, 2-bath home offers nearly 2,000 square feet of open-concept living with modern finishes, energy-saving solar panels, and access to a private boat ramp on Shingle Creek.The oversized kitchen serves as the heart of the home, featuring granite countertops, stainless steel appliances, abundant cabinetry, and a large island perfect for entertaining family and guests.Step outside to your covered lanai and enjoy the privacy of a wooded conservation area with no rear neighbors. Residents enjoy access to boating, fishing, playgrounds, and convenient proximity to The Loop, Disney, Orlando International Airport, and major highways.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Ana Manzo (321-318-9338)

Remarks: Move-in ready three-bedroom, two-bathroom home located in the Poinciana Subdivision Neighbourhood 5 North Village. This residence features a functional layout designed for modern living, highlighted by a kitchen that is beautifully finished with quartz countertops and stainless steel appliances. The primary suite offers added convenience with a large walk-in closet, providing ample storage space. The exterior of the home includes a fully fenced-in backyard, offering a secure space for outdoor entertaining or pets. Perfectly positioned near shopping, dining, schools, and everyday essentials, this home is part of a Planned Unit Development (PUD) with low HOA fees. Schedule your private showing today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Under contract-accepting backup offers. Welcome to your ideal getaway or investment opportunity in the heart of Kissimmee! This well-appointed condo-tel features two full beds and an updated bathroom, offering a comfortable and inviting retreat for guests or owners alike and provides the perfect blend of convenience and vacation-style living. Ideally located near Kissimmee’s popular dining, entertainment, and shopping destinations, this property offers easy access to everything the area has to offer, including world-famous attractions. The community amenities enhance the experience with a swimming pool, on-site laundry facilities, and shared common areas. Whether you’re seeking a low-maintenance vacation home or a great income-producing investment, this condo-tel is an exceptional opportunity in a prime location.

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

Listing Agent: Veronica Figueroa (407-519-3980)

Remarks: Under contract-accepting backup offers. Charming and beautifully positioned 3 bedrooms, 2 bathrooms ground floor unit with peaceful garden view and resort style living at your doorstep. Just steps away from the sparkling community pool and gazebo, this home offers the perfect blend of comfort and convenience. Enjoy a bright, open layout filled with lots of light, a cozy back patio ideal for relaxing mornings, entertaining or unwinding evenings. A well kept home, with a lot of upgrades and all stainless steel appliances. Nestled in a prime location close to shopping, dining and major roadways. This is an exceptional opportunity for homeowners or investors seeking the Florida lifestyle at its best.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Claudette Banton Dennis (347-876-1091)

Remarks: Discover this brand-new construction townhome in Kissimmee, FL (34743) located in the highly desirable SoHo at Lakeside community, just minutes from Lake Nona, Orlando International Airport, and Medical City. This modern 3-bedroom, 2.5-bath townhouse offers a spacious open-concept layout designed for today’s lifestyle. Featuring high ceilings, contemporary finishes, 42” cabinetry, and stainless steel appliances, this home blends style, comfort, and functionality—perfect for both homeowners and investors. The primary suite provides a private retreat with dual closets, a balcony, and a double vanity bathroom, while additional bedrooms ,flexibility for family, guests, or a home office. Enjoy the benefits of new construction in Kissimmee, including energy efficiency, low maintenance, and updated design standards. The community offers resort-style amenities and a prime location with easy access to major highways, shopping centers, restaurants, and top employment hubs in Central Florida. Key Highlights: New Construction Townhome in Kissimmee 34743 Minutes from Lake Nona & Orlando International Airport Ideal for First-Time Buyers & Real Estate Investors Low-maintenance living with HOA-covered amenities Strong rental and appreciation potential in a growing area Whether you're looking to buy your first home in Orlando, invest in a high-demand rental property near Lake Nona, or secure a property in one of the fastest-growing areas of Central Florida—this is an exceptional opportunity.

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

Listing Agent: Rudy Morales, Pa (305-454-7821)

Remarks: Welcome to this spacious 7-bedroom, 4.5-bathroom pool home located in the highly desirable Emerald Island Resort, one of the most sought-after short-term rental communities in the Orlando area. With nearly 2,900 square feet of living space, this home is ideal as an income-producing vacation rental or a private second home near the attractions. Designed for comfort and entertainment, the home features multiple living areas, themed bedrooms, a theater room, and a game room, offering an unforgettable experience for guests and owners alike. The private screened pool and spa provide the perfect place to relax after a day exploring Orlando. Recent updates include fresh interior and exterior paint and updated furnishings, including new living room furniture and refreshed pool patio furniture. The roof is a 2023, the pool equipment is 2025, and the HVAC units are newer and have been serviced regularly. Emerald Island Resort is a 24-hour guard-gated community offering resort-style amenities including a clubhouse, community pool and spa, fitness center, tennis and basketball courts, playgrounds, and walking trails. Ideally located just 10–15 minutes from Walt Disney World, approximately 20–25 minutes to Universal Orlando Resort and Epic Universe, and around 20 minutes to SeaWorld. Florida’s East Coast beaches such as Cocoa Beach are about an hour away, while the Gulf Coast beaches including Clearwater and St. Pete Beach are roughly 1 hour and 45 minutes away. With its prime location near shopping, dining, and major attractions, this property offers the perfect combination of investment potential and vacation lifestyle in the heart of Central Florida. BOOKING AND INCOME HISTORY AVAILABLE UPON REQUEST.

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

Listing Agent: Rebecca Readus (423-414-5019)

Remarks: Welcome to your own private retreat in the heart of Poinciana! Located in the growing Polk County side of Poinciana, this spacious 2-story home at 2074 Rio Grande Canyon Loop offers the perfect combination of functionality, comfort, and outdoor living that is hard to find at this price point. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,154 square feet of living space, this home was designed with family living and entertaining in mind. The first floor offers a formal living room and formal dining room that are ideal for holidays, gatherings, and special occasions. The oversized kitchen provides abundant cabinet and counter space, a breakfast bar, and an additional dinette area, all overlooking the large family room to create an open and inviting atmosphere. A downstairs laundry room and convenient half bath complete the first floor layout. While the interior is in very good condition, the home also presents an excellent opportunity for the next owner to add their own modern touches and upgrades over time. To help make that transition even easier, the seller is willing to offer a flooring credit with a reasonable accepted offer so the new owner can personalize the flooring to their own taste and style. But the TRUE SHOWSTOPPER of this property is the incredible backyard oasis. Step outside and prepare to fall in love with a resort-style outdoor retreat featuring an estimated $70,000 custom pool and spa package designed for year-round Florida living. Whether you are entertaining guests or simply relaxing after a long day, this backyard was built to impress. The outdoor space includes a beautiful pergola, outdoor seating area, grilling station, electric fireplace, and even a pop-up TV — all of which convey with the property. This outdoor paradise creates the perfect setting for family gatherings, game days, weekend BBQs, or peaceful evenings under the stars. Additional upgrades and features include: Recently replaced AC system Pre-wire and electric capability for a generator Spacious floorplan with multiple living areas Large backyard entertainment space Pool and spa retreat perfect for Florida living This is more than just a house — it is an opportunity to own a home with incredible outdoor living potential, solid major upgrades already completed, and the ability to customize the interior to your own personal style.

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Alex Vazquez (407-270-6841)

Remarks: Welcome to this spacious two-story home perfectly positioned on a desirable corner lot! This inviting 3-bedroom, 2.5-bath residence offers plenty of potential for a growing family seeking comfort, privacy, and convenience. The first floor showcases an open-concept layout with tile flooring throughout, creating a practical and functional flow. Upstairs, you’ll find cozy carpeted bedrooms offering a comfortable retreat for rest and relaxation. Enjoy year-round outdoor living with your own private, screened-in pool complete with a fenced backyard for added privacy. Inside, the home features a convenient laundry room, ample natural light, and generous storage space throughout. Perfectly located, this home is literally just minutes from Florida’s Turnpike, providing quick access to the 417 Central Florida Greenway and Orlando International Airport. You’ll also be a short drive from world-famous attractions such as Walt Disney World, Universal Studios, SeaWorld, and Lake Nona’s Medical City. Close to shopping, dining, and excellent schools, this property offers outstanding potential and a great opportunity to own a pool home in one of Kissimmee’s most convenient locations!

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Junior Montero (407-234-2334)

Remarks: Under contract-accepting backup offers. This fully furnished, 2BD/2BA, fourth-floor condo in Storey Lake is the definition of a turnkey revenue play. Just 14 minutes from Disney, this unit is already a high-performing Airbnb with strong occupancy and glowing guest reviews — no ramp-up period, no setup costs, no guesswork. Inside, you get a bright, modern, open layout with stylish furnishings, a private balcony, and a full, ready-to-host setup from day one. Whether you’re optimizing for nightly rate, extended stays, or personal use between bookings, this layout and location hit every mark. Storey Lake is a resort powerhouse with everything guests look for: multiple pools, a lazy river, splash pad, full gym, on-site restaurant + bar, and recreation that keeps guests onsite (and rebooking). That’s the kind of amenity package that drives repeat stays and pushes occupancy even in off-peak seasons. Prime location. Proven income. Zero setup. Whether you hold it as a cash-flowing short-term rental, use it as your own vacation landing pad, or both — this one is built to perform.

Listing is courtesy of: EXP REALTY LLC (407-305-4300)

Listing Agent: Tony Ubaldini (407-242-6781)