Homes for Sale Near Osceola High School in Kissimmee - 151 homes

Remarks: Under contract-accepting backup offers. Seize the chance to explore this inviting townhome, ready for you to move in and make it your own. Featuring two spacious bedrooms and a versatile loft, this area can easily be transformed into a third bedroom, a productive home office, or a cozy family room—tailored to fit your lifestyle. Recent upgrades, including a brand-new roof finished in January 2025 and plush carpeting installed in November, offer peace of mind and comfort. Situated in an ideal location, you’ll find yourself just moments away from bustling shopping centers and The Loop, a lively hub filled with popular restaurants and major retailers like BJ's, JC Penney, Ross, Rooms To Go, and Hobby Lobby. Beyond the conveniences of daily living, the townhome’s proximity to Orlando’s renowned attractions—such as Disney World, SeaWorld, Universal Studios, and Orlando International Airport—ensures endless entertainment and travel possibilities right at your doorstep. Be sure to put this exceptional home at the top of your viewing list—it’s an opportunity you won’t want to miss!

Listing is courtesy of: FLORIDA PROPERTY HOMES (407-728-4650)

Listing Agent: Luis Cabrera (407-728-4650)

Remarks: Welcome to this stunning 3-bedroom, 2.5-bathroom townhouse located in the highly desirable gated community of Townhomes of Flora Ridge. Perfectly positioned in the heart of Kissimmee, this home offers the ideal blend of comfort, convenience, and serene surroundings. Enjoy breathtaking lake views right from your home which are perfect for relaxing mornings and peaceful evenings. The community features family-friendly amenities including a playground and tennis court, all within a quiet, well-maintained neighborhood that provides both security and tranquility. Location is everything, and this property delivers. Just minutes from The Loop Shopping Center, you'll have easy access to shopping, dining, entertainment, and major retailers like Lowe’s. You’re also close to medical centers, hospitals, and major highways, making daily commuting effortless. Plus, world-famous attractions like Walt Disney World Resort are just a short drive away. Whether you're looking for a primary residence or a strong investment opportunity, this property checks all the boxes in one of Kissimmee’s most convenient and sought-after locations. Don’t miss your chance—schedule your private showing today.

Listing is courtesy of: VITAL REALTY GROUP INC (407-944-1833)

Listing Agent: Daniel Santos (407-413-2548)

Remarks: Under contract-accepting backup offers. SELLER MOTIVATED - PRICE TO SELL - GREAT OPPORTUNITY STUNNING FULLY RENOVATED 3 BEDROOM POOL HOME – PRIME LOCATION IN KISSIMMEE Welcome to this beautifully upgraded 3-bedroom, 1 bonus room, 2-bathroom home located and a spot available with possibility to build a one more bathroom. This property has been completely renovated with high-end finishes throughout and offers the perfect blend of elegance, comfort, and Florida lifestyle living. Fully renovated interior. Premium, first-line flooring throughout. Sophisticated wood panel accent walls. Designer-decorated bedrooms. Completely remodeled kitchen with modern finishes. Updated bathrooms with contemporary style. Extended driveway for additional parking Private heated pool with spa. Outdoor gourmet area perfect for entertaining. Beautiful pond water view with a colonial-style architectural details. Gated community for added security. The open floor plan creates a bright and welcoming atmosphere, ideal for both primary residence, vacation home, or investment property. The backyard is a true retreat, featuring a heated pool and spa overlooking a peaceful pond view — perfect for relaxing evenings or entertaining guests. This home shows pride of ownership and attention to detail in every corner. The bedroom furniture has been removed; the summer kitchen needs to be finished, and the refrigerator was removed because it was broken. Seller is highly motivated and priced to sell. Excellent opportunity in one of Kissimmee’s most sought-after areas, close to major highways, shopping, dining, and attractions.

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

Listing Agent: Francisco Tatagiba Junior (386-517-3488)

Remarks: Dream townhome alert! This gorgeous 4BR/3BA (including 2 ensuites) unit in San Vitorino Cir, Kissimmee offers 1,470 sq ft of bright, open living space perfect for entertaining and relaxing. With a recently remodeled owner's suite and a recently replaced AC unit and boiler. Enjoy your morning coffee on the small patio / varanda, and experience the comfort of move-in ready Florida living. The community features 3 sparkling pools, a full clubhouse, and plenty of amenities for fun and fitness. Prime location near highways, shopping, dining, and schools— don’t wait, your new home awaits!

Listing is courtesy of: DEBRASSI REALTY LLC (407-446-1343)

Listing Agent: Marcela Andrade Drummond (407-752-2323)

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: Experience stylish and comfortable living in this beautifully designed townhome located within the sought-after Tapestry community. Perfectly positioned at 2504 Fassona Drive, this residence offers convenient access to Central Florida’s major highways, shopping, dining, and top attractions. Featuring 3 spacious bedrooms, 2.5 bathrooms, a downstairs primary suite, and a screened lanai, this home blends functionality with modern elegance. Interior highlights include quartz countertops, expansive windows that fill the home with natural light, and sleek railing details that create an open and inviting atmosphere. Move-in ready and thoughtfully designed, residents also enjoy resort-style amenities including a fitness center, 24-hour security, and a guarded gated entrance.

Listing is courtesy of: THE AGENT, INC (407-278-7090)

Listing Agent: Maria Godoy (407-906-0112)

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. HOA includes lawn maintenance. 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: FORMER MODEL HOME! This stunning home features 4 bedrooms on the main floor, including a guest room with walk-in shower, a dedicated office, and soaring high ceilings. The open layout is filled with natural light and showcases numerous upgrades throughout, including a modern kitchen with quality appliances and ample counter space. Upstairs has a spacious loft plus a full bedroom and full bath. Enjoy a fenced backyard with a hot tub, great for entertaining. Oversized 3-car garage provides ample storage and parking. Nestled in a gated community with a resort-style pool and fitness center. Situated on a 6,534 sq ft lot. Conveniently close to shopping, dining, and entertainment. This one will not last!

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Cozy concrete block home in Kissimmee just minutes from downtown — offering 1,495 sq ft of living space, 3 bedrooms, 2 bathrooms, and no HOA. Sitting on a fully fenced lot shaded by mature oak trees, this home has great bones and a welcoming feel from the moment you pull up. The covered front porch sets a relaxed tone, with plenty of room to sit and enjoy the outdoors. Inside, the open living room features tile flooring throughout and flows into a separate family room area, giving you flexibility for how you use the space. The kitchen offers honey-toned wood cabinetry, stainless steel appliances including refrigerator, range, and microwave, updated LVP flooring, and connects to an additional flex sitting area — ideal as a breakfast nook, office, or second lounge. Out back, a concrete patio opens to a spacious, fully fenced yard with a storage shed and plenty of room to spread out. The home is equipped with solar panels — helping reduce monthly energy costs. Please note solar panels are financed. Conveniently located near US-192, dining, shopping, and all of Central Florida's attractions.

Listing is courtesy of: RENAISSANCE REALTY NETWORK, IN (321-424-7617)

Listing Agent: Rafael Corrada (407-832-9691)

Remarks: Located in one of the most strategic areas of central Florida, this property offers a combination and potential for appreciation just minutes from Walt Disney, Universal Studios, and SeaWorld, very close to the Loop shopping mall, Osceola Parkway, and Florida Turnpike. It constitutes a high demand for rentals and new residents, making it ideal as a primary residence or long-term rental property. Quick access to supermarkets, schools, restaurants, and medical centers makes it an excellent and smart investment.

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Jesus Izaguirre (863-350-0401)

Remarks: Why wait to build when this tremendous home is available now! Located near all of Florida’s major attractions such as the theme parks and major roads, to several shopping centers such as The Loop, and more! Feel at peace as this home is located in a gated community which also contains beautiful ponds, playground, and a community pool; so much to enjoy! Stepping into the wonderful home through that captivating red door, wind down the hallway to see the spacious family room, dining room, and the stunning kitchen! The kitchen is truly a beauty, having quartz countertops, stainless steel appliances, and dark color cabinets that stand out. The upgrades keep coming as this marvelous home has crown molding throughout several areas on the first floor including the master bedroom, laminated flooring throughout the whole house, and modern style bathrooms. Enjoy serenity by stepping onto the screen enclosed patio with renovated flooring and take in the luscious view of the lake behind the house. There is enough room for you and your family thanks to the spacious floor plan. Do not wait any longer, come make this home yours today!

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

Listing Agent: Blanca Armada (407-908-2846)

Remarks: Property is Eligible for Free 1% interest rate Buydown for the first 12 months until June 30, 2026!!! $10,000 toward buyer's closing costs with full price offer. Beautiful 3-bedroom, 2-bathroom home located in a desirable area of Kissimmee, Florida. This property offers the freedom of NO HOA and NO CDD, making it a perfect option for homeowners or investors looking for flexibility and lower monthly expenses. The home features a functional layout with comfortable living spaces, ideal for families or those who enjoy entertaining. Conveniently situated near major highways, shopping centers, restaurants, schools, and just minutes from world-famous attractions in Central Florida. Kissimmee is known for its strategic location near Orlando and major theme parks, while also offering access to parks, lakes, and outdoor recreation throughout the area. Whether you are looking for a primary residence, vacation home, or investment property, this home offers an excellent opportunity in a rapidly growing Central Florida market. Don’t miss the chance to own a property in one of the most convenient and sought-after locations in the area. Additional Exterior and Interior property photos will be uploaded!

Listing is courtesy of: CAPITAL HOMES INC (800-642-0668)

Listing Agent: Alcides Gonzalez (407-267-6868)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Price Improvement! Welcome to this beautifully maintained condo for sale in the desirable gated community of Flora Ridge in Kissimmee. Located on the third floor with convenient elevator access, this residence offers comfort, space, and functionality in a prime location. As soon as you walk in, you’ll be impressed by the open and airy layout, where the living room and dining room flow seamlessly together — perfect for entertaining or relaxing at home. Natural light fills the space, creating a warm and inviting atmosphere. The kitchen offers ample cabinet storage, laminate countertops, and sleek stainless steel appliances, making it both practical and stylish. Just off the kitchen, you’ll find a dedicated laundry room complete with washer and dryer for added convenience. The main bedroom suite is generously sized and filled with natural light. A unique and versatile adjacent room connected to the primary suite can be used as a home office, nursery, sitting room, or even your dream custom closet space. The main bathroom is thoughtfully designed with dual vanity sinks, a walk-in shower with glass doors, a walk-in closet, and a private enclosed toilet room. On the opposite side of the condo, you’ll find two additional bedrooms with a full bathroom in between. The shared bathroom features a bathtub, ideal for guests or family. Bedroom two includes a built-in closet, while bedroom three offers a spacious walk-in closet. Step outside onto the private balcony, the perfect place to unwind in the evenings and enjoy Florida’s beautiful weather. Flora Ridge is a gated community in Kissimmee known for its tranquil, park-like setting and well-maintained grounds. Residents enjoy: Secure gated access for peace of mind, One assigned carport parking, right for two vehicles, Additional community parking spaces for visitors, Assigned overnight guest parking available for visitors, Lush landscaping and garden and water views throughout the neighborhood. Close to the Loop, Turnpike, Access to 417 and the Airport.

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

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

Remarks: Fantastic location in a highly desirable gated community! This move-in ready home is ideally located just minutes from The Loop Town Center, top rated restaurants, shopping plazas, medical facilities, major highways, the airport, and only 10 minutes from Disney and the theme parks. Enjoy added peace of mind with a BRAND NEW roof (05/2026) and NEW A/C, making this home truly move-in ready. Featuring an open floor plan filled with natural light, this beautifully maintained home offers 3 spacious bedrooms, high ceilings, a formal dining area, and a breakfast nook perfect for everyday living and entertaining. Residents enjoy resort-style amenities including a community pool, clubhouse, fitness center, tennis courts, walking trails, gated privacy, and HOA-maintained lawn care. This home truly combines comfort, convenience, and lifestyle in one exceptional location!

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

Listing Agent: Delia Navarro, Llc (321-541-8242)

Remarks: Rare Opportunity. Pristine former model home in the Guard-Gated Community of Tapestry. Experience luxury and peace of mind in this meticulously maintained home, designer-upgraded townhouse. As a former model home, this property boasts premium finishes and has been kept in impeccable condition- never used as a rental and ready for its new owners. Open Concept living, the spacious floor plan seamlessly connects the living, dining, and kitchen areas, making it perfect for entertaining. Located in the heart of Kissimmee the Tapestry community offers an active, resort-style lifestyle. Prime location: just minutes away from world class shopping, dining, top rated schools, and the excitement of Disney and Orlando's world-famous theme parks.

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

Listing Agent: Alexandra Cana (407-364-3578)

Remarks: One or more photo(s) has been virtually staged. Welcome to 3463 Forest Ridge Ln, located in the quiet gated community of Crestwood. This spacious 4-bedroom, 3.5-bath home with a 3-car garage offers over 3,800 square feet of thoughtfully designed living space, combining comfort, privacy, and an unbeatable Central Florida location close to shopping, dining, schools, and world-famous attractions. Designed for comfortable everyday living and entertaining, the home features expansive living spaces, a large kitchen with rich wood cabinetry, center island, pantry, breakfast nook, and a light-filled family room. The screened pool area provides the perfect private retreat for enjoying the Florida lifestyle year-round. The functional floor plan includes a designated office/den on the first floor, a convenient downstairs guest bedroom with its own en suite bath, generous living and dining areas, and a spacious primary suite featuring dual walk-in closets, double vanities, and a garden tub. The home is also ideally positioned near the community playground and pool area, offering convenient access to neighborhood amenities. major improvements provide peace of mind, including a new roof installed in 2021, two HVAC systems installed less than three years ago, a fairly new water heater and pool pump. Conveniently located near The Loop, Walt Disney World Resort, SeaWorld Orlando, Universal Orlando Resort, and Orlando International Airport, this home combines convenience, comfort, and value in one exceptional opportunity.

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

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

Remarks: Welcome to this beautifully updated home on a desirable corner lot in the heart of Kissimmee! From the moment you arrive, you’ll notice the fresh exterior paint, inviting curb appeal, and pride of ownership throughout. Step inside to discover a bright and spacious layout featuring a stunning updated kitchen designed to impress, complete with gorgeous quartz countertops, modern finishes, and the perfect setup for both everyday living and entertaining. The open flow of the home creates a warm and welcoming atmosphere ideal for gathering with family and friends. The primary suite offers a refreshed vanity area with stylish updates, creating a relaxing private retreat. Outside, the corner lot provides added space, privacy, and curb appeal that’s hard to find. Located in an incredibly convenient and highly sought-after Kissimmee location, you’re just minutes from The Loop, shopping, dining, Orlando International Airport, major highways, theme parks, Lake Nona, and all that Central Florida has to offer. Whether you’re looking for a primary residence or a vacation home, this move-in-ready property offers the perfect combination of location, updates, and value. Homes with upgrades like this in such a prime location do not last - schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Patrizia Harrington (908-329-0392)

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: PRICE IMPROVEMENT — NOW OFFERED AT $544,900! SELLER MOTIVATED & READY TO REVIEW OFFERS! An incredible opportunity to own one of the best-valued larger homes in the highly desirable guard-gated community of Tapestry. This immaculate and move-in ready Antigua model offers over 2,800 SqFt of beautifully designed living space featuring a first-floor primary suite, 3 bedrooms downstairs, a versatile flex/bonus room, spacious upstairs loft with private full bathroom, and 3 full bathrooms plus 1 half bath. One of the secondary bathrooms downstairs is a convenient Jack & Jill bathroom ideal for shared use between bedrooms. The primary suite offers direct backyard access, dual vanities, a soaking tub, walk-in shower, and spacious layout designed for comfort and privacy. The open-concept floor plan is bright and inviting, featuring a chef-inspired kitchen with quartz countertops, stainless steel appliances, 42-inch cabinets, and a large center island perfect for entertaining. Enjoy peaceful conservation views with NO rear neighbors, plus a screened lanai, pergola-covered patio, and fully fenced backyard ideal for relaxing or hosting gatherings. Additional features include tile roof, interior laundry room, 2-car garage, and low HOA. Perfect for multigenerational living, remote work, entertaining, or families needing extra space. Residents of Tapestry enjoy resort-style amenities including 24-hour live security guards, luxury pool, fitness center, clubhouse, walking trails, playgrounds, and high-speed fiber optic internet throughout the community. Prime location just minutes from Disney, The Loop, dining, shopping, and major highways. Move-in ready and priced to sell, schedule your private showing today before this opportunity is gone!

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

Listing Agent: Sol Peinado (407-486-5259)

Remarks: LOCATION! CONVENIENCE! SECURITY! Move-in ready and updated 4-bedroom, 3-bath townhouse in Venetian Bay Villages is ideal as a primary home, vacation retreat, or income-producing investment. The spacious layout features a first-floor master suite with a jetted tub, updated kitchen and baths, and a 2018 roof. Enjoy 24/7 guard-gated security and resort-style amenities, including 4 pools, fitness center, spa, clubhouse, theater, game room, playgrounds, tennis, basketball, volleyball, and BBQ areas. Perfectly located just minutes from Disney, Universal, shopping, dining, and major highways, this turnkey property offers unmatched comfort, convenience, and value. Property is being sold fully furnished. Zoned for short-term rental, perfect as an Airbnb investment or primary residence.

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

Listing Agent: Evelyn Lopez Correa (787-475-2292)