Homes for Sale Near Osceola High School in Kissimmee - 103 homes

Remarks: Welcome to this beautifully presented pool home in Kissimmee! This spacious residence showcases the kitchen featuring elegant gold fixtures and sleek stainless steel appliances, including a range, refrigerator, dishwasher, and microwave. Designed for both comfort and entertaining, the home offers a bright living room and a cozy dinette space. Enjoy the clean, modern feel of no carpet throughout, complemented by stylish flooring and ceiling fans in several rooms for added comfort. Both bathrooms have been tastefully updated, enhancing the home’s contemporary appeal. Step outside to a large screened-in patio overlooking a sparkling open-air pool—perfect for relaxing or hosting gatherings. The fully fenced backyard adds an extra layer of privacy, making this home a true retreat.***Home square footage, taxes, lot sizes, and schools; are to be independently verified.***

Listing is courtesy of: ALLEGIANT MANAGEMENT GROUP INC (407-557-3164)

Listing Agent: Elizabeth Santiago Moyet (321-231-2105)

Remarks: Under contract-accepting backup offers. This Retreat is a Masterpiece of Craftsman Artistry This seller has thought of everything before you can even imagine it! This estate boasts over 3,300 square feet with 3 bedrooms, 3.5 bathrooms and an attached 1 bedroom, 1 bath apartment. It will give you the experience of a life of uncompromised luxury and small-town charm in this spectacular Craftsman estate. Re-imagined with attention to detail and situated on a sprawling half-acre double corner lot, this home isn’t just a residence—it is a sanctuary. Located in the coveted Orange Gardens neighborhood, no HOA, you are mere steps from the vibrant energy of downtown boutiques, artisan dining, and the convenience of commuter and Amtrak rail services. You can also enjoy the near by parks with a short walking or biking distance away. From the curb, the home radiates quality. It has a gable hip roof and concrete block hardi board exterior with seamless gutters. The true magic, however, begins with entering a foyer that takes your breath away. Looking down, the limestone and travertine floor showcases an original clematis design. Above, the octagonal cathedral ceiling features a hand blown glass fixture surrounded by translucent panels, filtering in natural light. Ultimate Retreat & Personal Fortress The primary suite is a masterclass in tranquility. Drift off under a romantic barrel-vaulted trey ceiling with soft cove lighting, or enjoy your morning coffee on the private screened patio. For a peace of mind, the suite features a discreetly integrated storm sanctuary—a custom walk-in closet reinforced with a roll-down door to keep your loved ones safe during any weather. The ensuite is a spa-like escape, boasting a two-person Jacuzzi tub and a floor-to-ceiling double-head shower surrounded by cultured marble, turning every morning into a five-star experience. Built for Connection & Creating Memories The gourmet kitchen and great room are a host’s dream. Imagine holiday gatherings centered around the massive granite island, with cocktails served from the professional-grade wet bar. Diamond Reflections cabinetry with appliance garages to keep your workspace pristine. The great room’s coffered ceilings and filtered sunlight create an atmosphere of warmth and sophistication. Alfresco Potential: Step out onto the patio—engineered with heavy-duty footings—ready to be transformed into the ultimate outdoor kitchen or covered lounge. For versatility, a secondary suite features a Murphy bed system, transforming a high-end home gym or executive office into a luxury guest suite. A third bedroom with an ensuite & patio access is also situated just down the main hall from the primary, giving you more space and privacy for all of your guests. If multi-generational living or a lucrative income stream is of interest, the attached private apartment is fully-equipped, offering its own kitchen, laundry, and separate entrance without sacrificing the main home’s privacy. Behind the beauty lies unparalleled engineering and self sufficiency. Throughout you will see several Velux sun tunnels that provide natural sunlight. A new roof as of 2023 and a whole house water filter and water softener. Across the home is four HVAC zones makes this home as "smart" as it is stunning. ADT hardwired security & privacy hedges ensure your private patio remains private. This is a thoughtfully crafted lifestyle for the buyer who demands excellence in every inch of their surroundings.

Listing is courtesy of: RIVER HILLS PROPERTIES, LLC B (315-896-1009)

Listing Agent: Heather Claridge (941-404-8193)

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: One or more photo(s) has been virtually staged. Welcome to 2365 Rapollo Drive, located in the highly sought-after gated community of Tapestry in Kissimmee! This beautifully maintained residence offers the perfect blend of comfort, style, and convenience. Featuring a spacious open-concept floor plan, this home is ideal for both everyday living and entertaining. The chef-inspired kitchen boasts modern cabinetry, granite countertops, stainless steel appliances, and a large center island overlooking the living and dining areas. Natural light fills the home, highlighting the thoughtfully designed layout and generous living spaces. The primary suite offers a with a walk-in closet and an ensuite bath complete with dual vanities and a spacious shower. Additional bedrooms provide flexibility for guests, a home office, or growing needs. Step outside to the fenced backyard space perfect for relaxing evenings or weekend gatherings. Residents of Tapestry enjoy resort style amenities including a clubhouse, sparkling pool, fitness center, and 24hr gated/guarded security. Conveniently located near The Loop shopping center, major highways, dining, and just minutes from world-famous attractions and Orlando International Airport. Don’t miss this opportunity to own in one of Kissimmee’s premier communities. Call to schedule your private showing today! Virtual tour available (English): https://youtu.be/g8VTYhJaErk . Virtual tour available (Spanish): https://youtu.be/MxjL10fnLpE

Listing is courtesy of: AGG REALTY & MANAGEMENT LLC (407-267-7926)

Listing Agent: Amar Guemraoui (407-267-7926)

Remarks: Welcome to this well-maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and location. Inside, you’ll find multiple living spaces including a formal living room, dining room, and a spacious family room—ideal for both everyday living and entertaining. The kitchen flows seamlessly into the main living areas, creating a warm and inviting atmosphere. The primary suite features a large bathroom complete with a soaking tub and separate walk-in shower, providing a relaxing retreat. Step outside to your private backyard oasis with a screened-in pool and fully fenced PVC yard—perfect for enjoying Florida living year-round. Additional updates include a newer AC system installed in 2023 for added peace of mind. Located in the desirable Cranes Cove community, residents enjoy low HOA fees and access to a community pool. Just minutes from The Loop shopping center, you’ll have convenient access to restaurants, movie theaters, shopping, and more. Plus, you’re a short drive to Disney and all that Central Florida has to offer. Whether you’re looking for a primary residence, investment property, or vacation home, this one truly checks all the boxes.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Dominick Florio (321-377-4045)

Remarks: Under contract-accepting backup offers. Welcome to this beautiful 2021 build home and just renovated to bring new life to it. This move in ready 1341sqft 3BDR/2BTH property features a bright open layout with brand-new luxury vinyl plank flooring, recessed lighting, modern ceiling fans and fresh paint throughout. Enjoy a beautifully updated kitchen with new shaker cabinets, quartz countertops, and stainless-steel appliances. The bathrooms received new vanities, mirrors, and floor-to-ceiling porcelain tile shower. Since it was built in 2021 the major components (roof, A/C, tankless water heater, plumbing, electrical and windows) are like new. Enjoy easy access to Florida’s Turnpike, U.S. 192 and I-4, placing you just minutes from world-famous theme parks, shopping, restaurants, and entertainment. Whether you’re searching for your next family home or a vacation rental this home will fit your needs. The renovated homes in this area are moving fast so it won’t last long. Book your appointment today so you don’t miss this gem.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Felipe Patricio (407-325-1608)

Remarks: Location, location, location! Investors and buyer's delight. This ground floor apartment with screen in porch offers 2 bedrooms and 1 bathroom with lovely tiles all around. Gorgeous stone counter tops, washer and dryer, a very sunny and open space for your enjoyment. A great gated community with basketball course, gym, club House and pool. Plenty of parking and easy access to all the supermarkets, stores, restaurants and parks. Call to schedule a private showing today.

Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)

Listing Agent: Britzeida Pichardo (347-549-7568)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully upgraded 3 bedroom 2.5 bathroom townhome at Heritage Key Villas in Kissimmee, offering comfort, style and a peaceful pond view. Step inside and immediately appreciate the modern upgrades throughout. The entire home features luxury vinyl plank flooring on the first floor, staircase and upstairs, creating a cohesive and elegant look while being durable and easy to maintain. The kitchen features a large granite island, ample cabinetry and an open layout that flows seamlessly into the dining and living area. Upstairs the secondary bathroom has plenty of cabinet space and has an enclosed shower. Light fixtures, and ceiling fans have been tastefully replaced, giving he property a fresh modern feel. New toilets. One year old appliances including the washer and dryer. The three bedrooms provide comfortable living space. The main bedroom has serene pond views from two windows. Screened in porch overlooking the pond. Sit and enjoy the relaxing view. The community residents enjoy a community pool, spa, fitness center, playground and a clubhouse. Close to shopping, dining and major highways.

Listing is courtesy of: SUNSHINE PREMIUM PROPERTIES (407-414-7581)

Listing Agent: Monica Mendivil (407-414-7581)

Remarks: Welcome to Regal Cove – Modern Luxury Meets Country Charm! Imagine living in the exclusive, gated community of Regal Cove, where this fully renovated custom home offers both elegance and privacy. Set on nearly half an acre (.49), this residence boasts one of the largest private screened lap pools in the area with a heated spa—perfect for entertaining or relaxing year-round. From the moment you arrive, the long driveway and welcoming front porch set the tone for comfort and sophistication. Step inside the brand-new modern renovation featuring an open concept design and tasteful finishes throughout. The spacious family room is highlighted by an elegant tile accent wall with an electric fireplace and French doors overlooking the pool and mature tree views. The gourmet kitchen is a showpiece with a waterfall island, drop-down range system, top-tier appliances, custom cabinetry, built-in double oven/microwave, wine cooler, and coffee station. A true chef’s delight, it’s designed for hosting family and friends with ease. The primary suite, located on the first floor, offers a stunning walk-in closet and a spa-like bathroom with a freestanding soaking tub, double vanities, separate water closet, and an oversized double-head shower. Upstairs, you’ll find four additional bedrooms with a sleek glass panel railing system, a bonus storage room, and two beautifully renovated Jack & Jill bathrooms. Adding incredible flexibility, a three-car garage with extended roofline includes a private full apartment above the garage with a bedroom, bathroom, kitchen, and living/dining area. Perfect as a guest house, or secondary suite. Outdoor living shines with two covered patio areas, French impact windows, and the expansive screened pool deck. With only $400/Quarter HOA fees, Regal Cove provides an upscale yet affordable lifestyle, ideally located near Lake Tohopekaliga with a public boat ramp less than a minute away. You’ll also enjoy easy access to the FL Turnpike, Publix, Walmart, and all of Kissimmee’s conveniences. This is a rare opportunity to own a modern, custom-renovated pool home with an in-law suite in one of Kissimmee’s most desirable gated communities. Schedule your private showing today and experience the perfect blend of country charm and modern luxury.

Listing is courtesy of: FIERCE REALTY (407-758-5179)

Listing Agent: Rachel Coolidge (207-522-0838)

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: VENTURE HOME REALTY (407-587-0076)

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

Remarks: Fully Furnished & Move-In Ready Villa!! Welcome to this beautifully updated 2-bedroom, 2-bath villa located in the heart of Kissimmee! This turnkey home is being sold fully furnished, making it the perfect opportunity for first-time buyers, seasonal residents, or investors looking for an immediate rental. Step inside to find a bright and open layout featuring tile flooring throughout, an updated kitchen, and a comfortable living space ready to enjoy from day one. Recent improvements include a new roof, giving peace of mind for years to come. Enjoy low-maintenance living in a well-established community offering amenities such as a pool and tennis courts, all while being just minutes from shopping, dining, and entertainment at The Loop, major highways, and area attractions. Whether you’re looking for a primary residence, vacation home, or income-producing property, this one checks all the boxes: Prime location, Fully furnished, Move-in ready, Incredible value. Seller is motivated—schedule your showing today!

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

Listing Agent: Angie Pereira (407-721-8945)

Remarks: Under contract-accepting backup offers. Discover comfort and convenience at Cascades at Kissimmee with this well-maintained 2-bedroom, 1-bath condominium offering approximately 870 square feet of thoughtfully designed living space. The interior features an open, airy floor plan with abundant natural light, a welcoming living and dining area, and a stylish galley kitchen complete with breakfast bar and updated appliances—ideal for both everyday living and entertaining. The generously sized primary bedroom includes a walk-in closet and private access to the renovated full bath. Recent improvements such as fresh interior paint enhance the home’s clean, modern feel. Enjoy outdoor relaxation on the screened balcony, which also provides additional storage, plus the added convenience of an in-unit washer and dryer. Residents enjoy access to community amenities including a swimming pool within view from the balcony, clubhouse, and tranquil pond views. Centrally positioned near major roadways, shopping, restaurants, and entertainment, with easy drives to The Loop, area attractions, and Orlando International Airport. A great option for owner-occupants or investors alike—ready for immediate occupancy. Schedule your private tour today.

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

Listing Agent: Alex Dallos (407-486-8034)

Remarks: Best value in the city of Kissimmee! CASH ONLY. This upgraded 3-bedroom, 1-bath home is one of the most affordable properties in the entire zip code—an incredible opportunity you don’t want to miss. Move-in ready with recent improvements, this property offers the added benefit of NO HOA, providing freedom and flexibility for homeowners and investors alike. Ideally located in Kissimmee, just approximately 20 minutes from Orlando International Airport and 25 minutes from Walt Disney World. Enjoy easy access to major roadways, including US-192, John Young Parkway, Osceola Parkway, and Florida’s Turnpike, making commuting a breeze. Conveniently close to shopping, dining, and schools. Perfect for first-time buyers or investors looking for strong value in a high-demand area!

Listing is courtesy of: FLORIDA LAKES REALTY (407-593-9087)

Listing Agent: Tatiana Diaz (407-593-9087)

Remarks: 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: This beautiful 3-bedroom, 2-bathroom home with a spacious 2-car garage is located in the highly sought-after gated community of Stonefield in Kissimmee. Designed for both comfort and convenience, this well-maintained property offers a bright and open floor plan, perfect for modern living. The home features generous living spaces with tile, a functional kitchen ideal for entertaining, and a private primary suite with ample closet space. The additional bedrooms are perfect for family, guests, or a home office. Residents of Stonefield enjoy access to a variety of resort-style amenities, including a sparkling community pool, fully equipped fitness center, tennis courts, and a playground. The gated entrance provides added peace of mind, while the community’s prime location offers easy access to theme parks, major highways, airport and walking distance to the Loop shopping plaza. Whether you're looking for a primary residence or an investment opportunity, this home offers the perfect blend of comfort, style, and community living. New Roof 2018. Schedule your showing today. The home may be sold furnished.

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

Listing Agent: Blanca Hernandez, Llc (407-493-9895)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2-bathroom pool home perfectly situated on a scenic pond in a gated community. This immaculately cared-for residence offers the ideal blend of comfort, privacy, and Florida lifestyle living. Relax or entertain in your private pool overlooking tranquil water views, creating the perfect backyard retreat. The home features a spacious and functional layout, ideal for both everyday living and hosting family and friends. Pride of ownership is evident throughout, making this home truly move-in ready. Conveniently located in a central location close to shopping, dining, and major roadways, with easy access to Orlando’s world-famous theme parks and Orlando International Airport, making travel and entertainment just minutes away. This exceptional home offers the perfect combination of location, lifestyle, and meticulous maintenance.

Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P (407-730-8737)

Listing Agent: Edwin Gonzalez (321-402-2284)

Remarks: 4 bedroom 2 bath home in a gated community. Living/dining room, large kitchen with eating space. 2 car garage. Pond view from the back of the house and conservation view from in part of the front.

Listing is courtesy of: REALTY SERVICES OF AMERICA (407-319-4113)

Listing Agent: Edgar Gonzalez (407-319-4113)

Remarks: Welcome to this beautifully appointed two-story corner-lot home nestled in the heart of Kissimmee. Featuring exceptional curb appeal with a brick-paved driveway, stone-accented façade, and meticulously maintained landscaping, this residence exudes elegance from the moment you arrive. The seller will pay off the remaining balance of the solar panels at closing. Step inside to an open-concept layout filled with natural light, where contemporary design meets comfort. The main living area includes elegant tile flooring, modern light fixtures, and custom wall details that add a touch of sophistication. The gourmet kitchen serves as a centerpiece, complete with granite countertops, an oversized island, and stainless steel appliances, all seamlessly connected to the dining and living spaces—ideal for both everyday living and entertaining. Upstairs, spacious bedrooms provide abundant natural light, while the primary suite serves as a private retreat, showcasing a spa-like ensuite with dual vanities, a soaking tub, and a walk-in shower. Situated on a desirable corner lot, the home also includes a fully fenced backyard perfect for relaxing or hosting gatherings. Conveniently located near major highways, premier shopping, dining, and top-rated schools, this home combines style, function, and location in one exceptional listing. The property includes solar panels, which significantly reduce electricity costs. The system will be paid off by the seller at closing, ensuring the new owner benefits from the energy savings without any remaining balance or financial obligation.

Listing is courtesy of: ALTIS REALTY (407-401-7447)

Listing Agent: Vicente Virgilio (407-401-7447)

Remarks: Great price on this beautifully renovated home, updated just three years ago! A proven, well-maintained rental with excellent income potential, this solid block 3-bedroom, 1-bath home offers side-yard parking behind fencing plus EV (electric vehicle) hookups. Renovated throughout, the home features all 3-year old appliances, ceramic tile flooring, a fully updated kitchen with 42” soft-close cabinets and stunning quartz countertops, recessed lighting, ceiling fans, tankless water heater, updated plumbing and electrical, 5/8” drywall, doors, paint, and updated ductwork. A/C (2017) and maintained. Enjoy outdoor living with a large covered back porch overlooking a refinished in-ground pool (2019), outdoor shower, RV concrete pad with electric, water, and security lighting, and a roof with solar attic vent. Additional upgrades include hurricane-certified double-pane vinyl windows. Ideally located near downtown Kissimmee, close to Osceola Parkway for shopping, schools, parks, major attractions, and easy access to both East and West Coast beaches. Move-in ready and investment-friendly—this one won’t last!

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

Listing Agent: Brandy Dileonardo (407-460-2107)

Remarks: Experience the epitome of resort-style living in this meticulously maintained 2-bedroom, 2-bathroom villa located within the exclusive gated community of Sterling Park at Stonefield. The interior radiates modern elegance with soaring ceilings, crown molding, and premium porcelain tile flooring throughout a bright, open-concept layout. At the heart of the home, the chef-inspired kitchen shines with crisp white cabinetry, granite countertops, and stainless steel appliances, seamlessly flowing into a sun-drenched dining area. Retreat to the spacious primary suite, complete with custom shutters and a spa-like ensuite featuring a dual vanity and a frameless glass walk-in shower. Beyond the glass sliders, your private screened-in lanai offers peaceful, unobstructed views of the community’s lush greenspace—perfect for quiet Florida mornings. With the HOA handling lawn and exterior maintenance, you’re free to enjoy the resort-style pool, fitness center, and tennis courts, all while being minutes away from world-class shopping at The Loop and major Orlando attractions.

Listing is courtesy of: MILESTONE FAMILY REALTY LLC (689-265-3683)

Listing Agent: Jeff Joachim (689-304-9330)