Kissimmee Homes For Sale & Real Estate - 3188 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: Your Florida Lifestyle Starts Here — Villa Living at Its Best! Whether you're escaping the cold, searching for a smart investment, or dreaming of your own Florida vacation home — this is the one you've been waiting for! Welcome to effortless Florida living! This beautifully maintained 2-bedroom, 2-bath villa is nestled inside a secure, resort-style gated community and offers the perfect blend of comfort, convenience, and lifestyle. Whether you are a snowbird seeking a warm seasonal retreat, an investor looking for a turnkey rental property, a vacation home buyer, or a full-time resident ready to enjoy resort-style living every day — this villa checks every box. Inside, a bright open layout connects the living and dining areas to a well-appointed kitchen featuring stainless steel appliances, generous cabinet storage, and abundant natural light. Durable laminate flooring flows throughout the main living spaces, while plush carpeting in the bedrooms adds warmth and comfort. The in-unit laundry and evident pride of ownership make this home truly move-in ready from day one. Outside your door, enjoy an impressive array of community amenities including a sparkling pool, fitness center, clubhouse, tennis and basketball courts, and a playground — everything you need to live, relax, and play without ever leaving the community. Low-maintenance living, a peaceful gated setting, and a Central Florida location close to world-class attractions, shopping, dining, and major highways make this an opportunity you do not want to miss. Schedule your private showing today!

Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)

Listing Agent: Julio Salgado (407-791-0265)

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: ***WATER VIEW HOME IN TOHOQUA – RESORT-STYLE LIVING IN KISSIMMEE *** Located in one of Kissimmee’s most sought-after communities, Tohoqua, this stunning water-view home offers the perfect blend of comfort, style, and convenience. Featuring a bright, open floor plan, a custom feature wall, and a screened-in lanai overlooking a serene water view, this home is designed for both relaxation and entertaining. Custom built in closets the primary suite and garage. Enjoy true resort-style living with access to a beautifully designed Residents Club, complete with a zero-entry pool, interactive water features, shaded playground, fitness center, clubhouse, and two lighted tennis courts. The community promotes an active and connected lifestyle with over 5 miles of scenic walking and biking trails that link directly to Twin Oaks Conservation Area and the Florida National Scenic Trail. Surrounded by natural beauty, residents also enjoy close proximity to Lake Tohopekaliga, perfect for boating, fishing, and kayaking. Future-forward living awaits with plans for an on-site Village Center featuring restaurants, shops, and a farmers market, bringing walkable convenience right to your doorstep. Ideally situated in the heart of Kissimmee, this home offers quick access to Lake Nona Medical City, Orlando International Airport (approximately 25–30 minutes), major highways, world-famous theme parks, and The Loop for premier shopping and dining, all within minutes. Families will appreciate the brand-new K-8 school conveniently located within the community (opened 2025), with a high school planned for the near future. This home truly offers a lifestyle of comfort, convenience, and community. Schedule your private showing today!

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

Listing Agent: Diana Mahadeo (407-223-1249)

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: One or more photo(s) has been virtually staged. Under Construction. This new four-bedroom Hendrix showcases convenient single-story living. Three secondary bedrooms are located near the front of the home off the foyer, near a versatile flex space ready to be used as an office or studio. An open-concept floorplan blends the kitchen, living and dining areas with easy access to a covered patio, while a luxe owner’s suite is nestled into a private rear corner, providing direct access to a full bathroom with dual sinks and a walk-in closet. Westview is a master-planned community in Poinciana, FL. This amenity-rich, pet-friendly community has something for residents of all ages to enjoy, including a swimming pool, dog park, clubhouse and sports fields. Lake Marion Creek Wildlife Management Area is nearby with hiking trails, as well as Poinciana for shopping, dining and entertainment options. The community is in close proximity to Highway 17 for easy commuting to Greater Orlando.

Listing is courtesy of: LENNAR REALTY (800-229-0611)

Listing Agent: Ben Goldstein (407-310-7677)

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: INVEST IN THE FUTURE — STEPS FROM NEOCITY! Rare opportunity to own a massive 4-bedroom townhome with an unusually low HOA of only $158/month in a premier gated community. This isn’t just a home; it’s a strategic seat at the table of Florida’s most exciting growth engine. Located less than 10 minutes from NeoCity, the state’s 500-acre high-tech epicenter, this property is perfectly positioned to benefit from the massive $470M semiconductor investment and the influx of high-wage tech jobs coming to the area. Whether you are looking for a spacious family residence or a high-yield investment, the 4-bedroom layout (rare for this area) provides maximum flexibility and demand. The home features a 2018-build with an open-concept kitchen, granite countertops, and a screened-in patio for private relaxation. Upstairs, four generously sized bedrooms and a convenient laundry room await. Enjoy resort-style community amenities without the resort-style price tag. With an HOA fee of $158/month, this low and the NeoCity tech boom next door, this property represents one of the strongest values in Osceola County. Schedule your showing before the secret is out!

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

Listing Agent: Juancarlos Caballero (407-334-7873)

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: One or more photo(s) has been virtually staged. Welcome to 923 S. Park Ct., Kissimmee, FL 34741 - a charming single family home situated in an established Osceola County neighborhood. This residence features three bedrooms and one full bathroom, offering a comfortable and functional layout with plenty of potential. The home features tile flooring throughout, making for easy maintenance. Step outside to enjoy a fully fenced front and back yard, providing space to relax. The backyard also includes a shed for additional storage and a driveway offers convenient off-street parking. The roof was completed in 2021. Ideally positioned near downtown Kissimmee, this home provides convenient access to a variety of shopping, dining and local amenities. This is a wonderful opportunity to own a single family home in a prime Kissimmee location. Schedule your showing today!

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: ASK ABOUT BUILDER INCENTIVES FOR CLOSING COSTS OR RATE BUY-DOWN! Welcome to the "Cypress" model by Honesty Homes! This open-concept, concrete block TILE ROOF home features high-end finishes and numerous upgrades throughout. You'll find 42" cabinets in the kitchen and bathrooms, sleek granite countertops perfect for culinary creativity, and soaring vaulted ceilings that enhance the sense of space. The master bedroom offers indulgence with its vaulted ceiling and two spacious walk-in closets for ample storage. Both bathrooms are thoughtfully designed with generously sized tubs and modern tiled showers, ideal for relaxation. Welcome to Tuscany Preserve, a gated, resort-style community offering a blend of luxury, comfort, and convenience. Residents enjoy a wide array of amenities, including a modern fitness center, a sparkling pool and spa, an elegant clubhouse ideal for social gatherings, and basketball and tennis courts for active living. Whether you're a first-time homebuyer, looking to downsize, or seeking the ideal vacation getaway, this property offers the perfect mix of contemporary living and serene surroundings — all just minutes from shopping, dining, top-rated schools, and major attractions.

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

Listing Agent: Amer Lababidi (407-800-3631)

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: Lowest-priced unit in the community! Now is your chance to own in the highly desirable Terra Verde Villas and enjoy true resort-style living every day. This private, well-maintained townhouse is tucked toward the back of the community for added peace and quiet. Inside, you’ll find a bright and functional layout featuring an organized kitchen, open dining and living space, a convenient downstairs bath, and a separate laundry and storage room. Step outside to your own private patio with a spa/hot tub and relaxing wooded conservation views — no rear neighbors. Upstairs offers 3 spacious bedrooms and 2 full baths, providing comfort for family, guests, or vacation renters. Located just minutes from the theme parks, restaurants, shopping, and major highways — everything is within easy reach. The gated community amenities include: • Resort-style pool • Clubhouse with restaurant & tiki bar • Hot tub & fitness area • Tennis courts • On-site cinema Perfect as a primary residence, vacation home, or income-producing investment. In today’s buyer-friendly market, this is outstanding value.

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Charles Kohlinger (407-421-9188)

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: Short Sale. Welcome home to this beautifully designed one-story residence offering the perfect blend of comfort and flexibility with 3 bedrooms plus a versatile flex room that can easily be converted into a 4th bedroom. Step inside to an open and inviting floorplan where luxury vinyl plank flooring flows throughout the main living areas, creating a seamless and modern feel. The kitchen serves as the heart of the home, featuring granite countertops, abundant cabinetry, a spacious pantry, and a counter-height island with seating that overlooks the expansive living and dining areas, ideal for both everyday living and entertaining. Thoughtfully designed with a split bedroom layout, the primary suite and flex room are privately positioned away from the secondary bedrooms, offering added privacy and endless possibilities for how the space can be used, whether as a home office, playroom, fitness area, or guest room. The primary suite offers a relaxing retreat with a large en-suite bath complete with a double sink vanity, quartz countertops, and a walk-in shower. Secondary bedrooms are well-sized and thoughtfully positioned, while the additional bathroom also showcases quartz countertops for a cohesive, upgraded look. Enjoy indoor-outdoor living with sliding glass doors leading to a screened lanai and a fully fenced backyard offering added flexibility with gate access on both sides, including a double gate entry. Additional highlights include a spacious laundry room, a two-car garage, and a welcoming covered front entry. Located in the Poinciana area, residents enjoy access to a variety of community amenities including parks, playgrounds, sports courts, fitness centers, and recreational facilities, along with nearby shopping, dining, and everyday conveniences, making this home an ideal blend of comfort and lifestyle.

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

Listing Agent: Alex Vastardis (407-947-6264)