Homes for Sale Near Osceola High School in Kissimmee - 148 homes

Remarks: This is the kind of home multigenerational buyers wait for. Tucked at the end of a quiet cul-de-sac shared with just one other home, 1980 Summer Ct sits on over half an acre and offers a rare setup designed for living together without giving up privacy, comfort, or independence. With two full kitchens, two laundry areas, two separate two-car garages, and three full baths, this property functions beautifully for extended families, in-laws, adult children, long-term guests, or anyone needing flexible living under one roof. A spacious shared living room creates a natural central gathering space, while the home splits into two distinct wings. One side features two bedrooms, two full baths, a full kitchen, its own family room, and access to the oversized screened lanai and fully fenced backyard. The other side offers a spacious primary suite with ensuite bath, a separate family room, a second full kitchen with pantry, and its own attached two-car garage. A paid-off solar system adds even more value from day one, helping keep electric costs down. With no HOA, plenty of room to spread out, and a location near East Lake Toho, Kissimmee Lakefront Park, Shingle Creek Regional Park, Downtown Kissimmee, St. Cloud, and the theme parks, this is a rare opportunity for buyers who need space, flexibility, and a home that truly supports the way modern families live.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Shawn Layton (321-514-8055)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautifully maintained two-story pool home located in one of Kissimmee’s most desirable gated communities. From the moment you arrive, this stunning residence impresses with its elegant curb appeal, soaring ceilings, abundant natural light, and thoughtfully designed spaces throughout. This spacious home features 5 bedrooms, 3.5 bathrooms, a versatile loft, plus formal living and dining rooms, offering the perfect balance of comfort, style, and functionality for everyday living and entertaining. The heart of the home is the spacious kitchen, complete with a center island, brand-new stainless-steel appliances, ample cabinetry, and a large walk-in pantry. Overlooking the main living area, the layout creates a warm and inviting atmosphere while still maintaining distinct living spaces for added comfort and privacy. The formal dining room provides the perfect setting for gatherings and special occasions, while the formal living room adds an elegant and flexible space ideal for entertaining or relaxing. The primary suite is conveniently located on the first floor, providing a private retreat with comfort and convenience. Upstairs, you’ll find four generously sized bedrooms, all featuring walk-in closets, along with a spacious loft ideal for a media room, home office, playroom, or additional living area. Step outside to your private screened-in pool area, the perfect space to relax, entertain, and enjoy Florida living year-round. Residents of the highly sought-after Stonefield community enjoy resort-style amenities including a beautiful clubhouse, community pool, fitness center, tennis court, and recreational areas. Ideally located near The Loop shopping center, dining, major highways, theme parks, and all that Central Florida has to offer. This exceptional home offers the perfect combination of space, elegance, comfort, and lifestyle. A true must-see!

Listing is courtesy of: TOP 7 REALTY LLC (407-334-8082)

Listing Agent: Audrey Torres (407-730-1862)

Remarks: Welcome to this spacious 3-bedroom + Office/smaller bedroom and 2-bathroom home offering privacy and tranquility with no rear neighbors and a stunning nature view from the screened-in patio. The interior features tile flooring throughout the main living areas, with cozy carpet in guest bedrooms. The Primary bedroom has luxury vinyl flooring. The kitchen has been tastefully updated, providing both style and functionality. The lanai has been extended and paved making it perfect for entertaining outdoors. Located in a man-gated community, residents enjoy top-notch security and access to resort-style amenities, including a community pool, fitness center, playground, and walking trails. Conveniently situated near major highways, shopping, and dining, this home combines comfort, convenience, and a peaceful setting. Owner Motivated

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Lorena Correa (407-415-9170)

Remarks: Welcome to this stunning 5-bedroom, 4.5-bath home with a versatile flex space located in the desirable gated community of Tapestry in Kissimmee. This beautifully maintained home features two master suites, one on the first floor and another on the second offering comfort and flexibility for multi-generational living or guest accommodations. The property includes a brand-new washer and dryer, a new stove, and hurricane shutters for added peace of mind. The spacious three-car garage provides ample storage and parking. Enjoy resort-style living with community amenities that include a saltwater pool, clubhouse, fitness center with yoga and spin studios, dog park, playgrounds, walking trails, and grilling pavilions. Conveniently located near The Loop, Old Town Kissimmee, Downtown Celebration, and major theme parks like Disney and Universal, you’ll also find plenty of shopping, dining, and entertainment options just minutes away. This home combines luxury, functionality, and location—schedule your private showing today before it’s gone!

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

Listing Agent: Jasmine Vazquez (407-800-5164)

Remarks: Welcome to this beautifully designed two-story home offering the perfect blend of comfort, style, and functionality. The first floor features a spacious flex room, ideal for a home office, complete with built-in shelving for added organization and charm. Just beyond the entry, the upgraded kitchen impresses with 42-inch cabinetry, granite countertops, stainless steel appliances, and a large center island—a perfect gathering spot for family and friends. The kitchen opens seamlessly to the family room, highlighted by a striking custom stone electric fireplace that adds warmth and elegance to the heart of the home. Off of the rear entry garage is the mud room ideal to keep the home clutter free from everyday items. All bedrooms are thoughtfully located on the second floor, along with a versatile loft that can serve as a media room, playroom, or additional workspace. The primary suite is a true retreat with tray ceilings and features an ensuite bathroom with marble countertops, dual sinks and two spacious walk-in closets. The home’s exterior offers both style and convenience with a rear-entry garage and a paved driveway that enhances the property’s curb appeal. Enjoy resort-style living in a 24-hour manned, gated community offering premium amenities, including an infinity pool, clubhouse, dog park, and multiple playgrounds. Ideally located just minutes from The Loop shopping center, the Florida Turnpike, SR 417, and world-famous theme parks, this home provides unmatched convenience and access to all that Central Florida has to provide.

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

Listing Agent: Jeannie Torres (407-414-3132)

Remarks: Welcome to the beautifully decorated Gardenia Floor plan, a designed 3-bedroom, 2-bath single-family home offering 1,706 square feet of thoughtful living space in the highly sought-after, guard-gated Tapestry community in Kissimmee. This isn’t just a home it’s a lifestyle. Step inside to an open, airy layout perfect for modern living. From cozy family nights to weekend entertaining, every square foot is optimized for comfort and flow. With three spacious bedrooms and sleek, contemporary finishes, the Gardenia model is the ideal blend of function and flair. Live like you're on vacation every day with access to a Zero-entry resort-style pool & cabana lounges, Splash pad & play spaces, State-of-the-art fitness center with yoga & movement studio, a Grand ballroom & catering kitchen for hosting unforgettable events, an Open-air veranda for sunset relaxation. Lots of Sports fields, BBQ pavilions, dog park, and walking and biking trails. And it’s all nestled in a 24-hour guard-gated community, minutes from Orlando's top attractions, major highways, the airport, shopping, dining, and great schools. Whether you’re looking for your primary residence, second home, or investment opportunity, this Gardenia beauty is your gateway to elevated living in Central Florida. Homes like this don’t just go on the market they go viral. Schedule your private tour before it’s gone!

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Gladys Bezerra (407-701-4034)

Remarks: Under contract-accepting backup offers. Back in the market, buyer's financing wasn't approved. 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: One or more photo(s) has been virtually staged. Beautiful and spacious first-floor corner condo featuring 3 bedrooms, 2 bathrooms, and a versatile office/den, located in the desirable gated community of Flora Ridge in Kissimmee. This recently fully painted, immaculately clean, move-in ready residence offers an open and functional layout with abundant natural light, spacious living and dining areas, and a screened balcony perfect for relaxing. The kitchen offers ample cabinet and storage space. The primary bedroom features an en-suite bathroom with dual sinks, a private toilet area, and a walk-in closet located within the primary bathroom. Tile flooring throughout the entire residence provides elegance, comfort, and easy maintenance. Flora Ridge offers gated access, a community pool, and walking paths. Conveniently located near restaurants, shopping centers, schools, major highways, Orlando International Airport, and Central Florida attractions. Ideal as a primary residence, second home, or investment opportunity.

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

Listing Agent: Priscilla Rivera (407-504-7154)

Remarks: One or more photo(s) has been virtually staged. SELLER ASSISTING WITH BUYER FINANCING, 2/1 BUYDOWN ON THE INTEREST RATE! Welcome to this wonderful 3-bedroom, 2-bathroom completely renovated home offering nearly 2100 sq. ft. of living space in the highly desirable Harbour Oaks community in Kissimmee, Florida. This spacious residence is designed for both comfort and style, featuring an open-concept layout, modern finishes, and thoughtful upgrades throughout. This renovation includes NEW Roof-Soffits-Gutters, Interior and Exterior Paint, both Bathrooms and Kitchen rehabs with Quartz Stone counters, SS Appliances, Breakfast Bar, Wet Bar, Luxury Vinyl Flooring, Blinds and Ceiling Fans throughout, Pool Refinished, Painted Decks front and back, Wood Burning Fireplace, Oversized 2-Car Garage, Pool Gazebo and Vinyl Fenced backyard. Enjoy your own private outdoor oasis with a sparkling pool and huge back yard—perfect for year-round Florida living and entertaining. Located just minutes from Historic Downtown Kissimmee, you'll have convenient access to shopping, dining, and entertainment. You're also perfectly positioned with a quick commute the Florida Turnpike, Lake Nona Medical City, major theme parks, schools, shopping and dining and the stunning Space Coast beaches. With its generous floor plan, multiple living areas, and every exceptional upgrade, this remarkable home has it all. Don’t miss your chance—schedule your showing today!

Listing is courtesy of: MACERA REALTY GROUP INC (407-246-1677)

Listing Agent: Peter Macera (407-970-2104)

Remarks: Under contract-accepting backup offers. Prime opportunity in a highly desirable location! Conveniently located just minutes from Old Town, major entertainment, and top hospitals—and only 20 minutes from Walt Disney World—this home is perfectly positioned for strong rental demand. Recent upgrades include a brand-new roof, updated electrical, new flooring, and a newly installed fence, providing peace of mind and low maintenance for years to come.Whether you’re looking to make this your primary residence or add a performing asset to your investment portfolio, this property delivers both value and versatility. Don’t miss this incredible opportunity!

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

Listing Agent: Amanda Little (407-720-9728)

Remarks: Welcome to 2516 Nouveau Way — a beautifully maintained 4-bedroom, 3-bathroom home located in a gated community just minutes from The Loop, shopping, dining, entertainment, major highways and Disney Parks. This spacious home features an open-concept layout filled with natural light and a desirable private-entry guest bedroom with full bathroom access, perfect for extended family, guests, or added privacy and flexibility. Designed for both comfortable everyday living and entertaining, this home offers the ideal blend of space, convenience, and location in the heart of Central Florida.

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

Listing Agent: Ariel Vargas (407-558-5161)

Remarks: Welcome to this beautifully maintained corner residence located in the highly sought-after gated community of Tapestry in Kissimmee. This well-designed 3-bedroom, 2.5-bath home offers a bright and open layout filled with natural light, creating an inviting atmosphere from the moment you arrive. With over 1,600 square feet of living space, the first floor features a seamless flow between the kitchen, dining, and living areas—perfect for everyday living and entertaining. The kitchen is equipped with stainless steel appliances, granite countertops, ample cabinetry, and a functional island that connects effortlessly to the main living space. Upstairs, you’ll find well-appointed bedrooms, including a generous primary suite designed for comfort and privacy. One of the home’s standout features is the private second-floor balcony—an ideal space to enjoy your morning coffee or unwind in the evening. Situated on a desirable corner lot, this property offers added privacy, an extended driveway, and enhanced curb appeal. Residents of Tapestry enjoy resort-style amenities, including a gated entrance with guard, a beautifully designed clubhouse, a large pool, fitness center, playground, and scenic walking areas. Ideally located just minutes from The Loop shopping area, Publix, a variety of restaurants, Osceola Parkway, and Orlando International Airport, this home offers both comfort and convenience in one of Kissimmee’s most desirable communities.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Yesenia Chacon Martinez, Llc (407-285-5717)

Remarks: This single-family home in Kissimmee features 2 bedrooms and 2 bathrooms across 1100 square feet, with an additional room and bathroom providing versatile space ideal for multi-room rental or extended living. Currently operating as a successful rental, the property generates consistent income. Inside, laminate and tile flooring flow throughout the home, while the kitchen offers ample counter and cabinet space with a convenient breakfast bar—perfect for meal prep or casual dining. The covered porch provides a comfortable spot to relax, entertain, or enjoy the outdoors. Located just minutes from major roads and transportation, this home offers easy access to Downtown Orlando, Walt Disney World, Orlando International Airport, and a variety of shopping and dining options. Its combination of flexible living space and prime location makes it a standout choice for both investors and homeowners alike. Mortgage savings may be available for buyers of this listing.

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: Pablo Cintron, Jr Pa (407-232-1819)

Remarks: Positioned along the storied shoreline of Lakeshore Boulevard, this rare income-producing property and location captures the timeless character of Historic Downtown Kissimmee with an address that places lifestyle, recreation, and long-term upside in one compelling package. Comprising six separate income producing apartments, 4 furnished and 2 unfurnished, with a total of 9 bedrooms and 6.5 baths. Property presents a remarkable opportunity for investors seeking immediate rental income or the possibility of a boutique hotel location in one of Central Florida’s steadily evolving waterfront corridors. Originally constructed in 1930, the building carries an architectural presence rarely replicated today blending vintage charm, and an unmistakable sense of place with views and walkability that continue to drive tenant demand. Situated directly across from Kissimmee Lakefront Park, residents enjoy effortless access to the marina, waterfront trails, fishing pier, playgrounds, amphitheater events, dining, cafés, and downtown entertainment all without relying on a car. The building spans over 4,100 square feet on an oversized corner-style lot and features private parking, scenic water and park views, and a setting surrounded by mature trees and historic homes that give the neighborhood its distinctive identity. The property’s layout creates unlimited opportunities. Downtown Kissimmee continues attracting attention for its lakefront revitalization, expanding SunRail connectivity and tourism corridor. Assets with authentic architectural appeal and irreplaceable positioning near the waterfront are becoming increasingly difficult to secure particularly those offering multi-unit versatility near the city’s cultural core. For the discerning investor, this is legacy-style holding in one of Kissimmee's most recognizable districts, where historic ambiance, waterfront surroundings, and enduring rental appeal converge.

Listing is courtesy of: ROMAN'S PRO REALTY LLC (407-610-1970)

Listing Agent: Petie Bilyk (407-361-1415)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2-bath pool home offering space, comfort, and an unbeatable location in the heart of Kissimmee. This property is a rare find featuring a 4-bedroom layout with a heated pool and spa on an oversized lot, combined with exceptional curb appeal thanks to its beautifully refreshed landscaping and freshly painted exterior (2024). The large, spacious driveway provides ample room for multiple vehicles. Step inside to an open and airy floor plan with soaring cathedral ceilings that enhance the sense of space and natural light throughout. The centrally located kitchen is ideal for both everyday living and entertaining, featuring ample counter space, a breakfast bar, and a dining nook perfectly positioned by the sliding glass doors offering beautiful views of the pool and backyard. The primary suite is a true retreat, offering dual walk-in closets, a linen closet, and a spacious bathroom with dual sinks and a relaxing jacuzzi tub with jets. Enjoy Florida living at its best in your private backyard oasis situated on an oversized, fully fenced backyard with a mango and an orange tree. The large screened-in patio and heated pool with spa create the perfect setting for entertaining or unwinding year-round. Additional highlights include NO HOA, a roof replaced in 2022, a newer pool pump, a newer pool heat pump, and a well-maintained interior ready for its next owner. Ideally located just minutes from major highways, shopping, dining, and everyday conveniences. Only 5 minutes to Historic Downtown Kissimmee and within 30 minutes to Orlando International Airport and Central Florida’s world-famous attractions. This home offers the perfect combination of space, location, and lifestyle. Don’t miss the opportunity to make it yours! Schedule your private showing today!

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

Listing Agent: Dania Khreiche (407-456-1553)

Remarks: Beautiful and spacious 4 bedroom, 2 bathroom home located in a highly desirable area, just minutes from shopping, dining, and everyday conveniences. This well-maintained property features a brand-new roof 2025 and has been freshly painted inside and out, making it truly move-in ready. Enjoy peaceful lake views from the backyard, perfect for relaxing or entertaining. The home offers a generous and functional layout ideal for comfortable living, along with a two car garage. Highly motivated seller! Competitively priced and ready to negotiate an excellent opportunity for both homeowners and investors, thanks to its prime location in a high-demand rental area. Schedule your showing today this one won’t last!

Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)

Listing Agent: Mercedes Corrente Bencomo (407-613-0006)

Remarks: One or more photo(s) has been virtually staged. This lovely, spacious condo in Kissimmee's gated Flora Ridge community offers the perfect combination of comfort and convenience. Located on the second floor with an elevator, this 1,779-square-foot apartment has an open layout that flows seamlessly between the kitchen and living room. There is also freshly painted interior throughout the unit, a recently replaced refrigerator, air conditioning and water heater, a master bedroom with double sinks and walk in closet, and a screened porch. Homeowners get two dedicated parking spots, one with a covered carport and one without. There is a community pool with amazing water view, and walking trail. It is situated just minutes from The Loop, a premier shopping and dining destination, making it easy to access the Florida Turnpike, Osceola Parkway, and world-famous theme parks. Along with the regular assigned schools, there is Renaissance Charter School with an A rating available from Kindergaden to 12th grade.

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

Listing Agent: Brigitte Elzarki (321-231-4999)

Remarks: Refined comfort meets Florida lifestyle in this spacious 5-bedroom 5 bathroom home within a gated community overlooking a tranquil pond. Offering 2,790 heated sq ft, the home features a versatile layout ideal for both daily living and entertaining. Bright living areas open to a screen-enclosed paver patio with water views and no rear neighbors, creating a peaceful outdoor retreat. Mature palm landscaping enhances the home’s tropical appeal. Built in 2008 and well maintained, the 5-bedroom, 5-bath layout provides flexibility for guests or work-from-home needs. Community amenities include a pool, sports courts, playground, and walking paths. Conveniently located near shopping, dining, schools, Orlando International Airport, and major attractions. A great opportunity for buyers seeking space, privacy, and location. Schedule your showing today.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Priscila Triska (321-354-5459)

Remarks: This beautiful 3-bedroom, 2-bath residence combines comfort and practicality in a sought-after neighborhood. Located within the secure, gated Tapestry community, the home features a charming front porch that opens into a bright and airy living space, flowing effortlessly to a private backyard patio. Positioned on a corner lot, the house benefits from plentiful natural light, enhancing its open feel. Inside, you'll find a spacious family room and a primary suite complete with a walk-in closet. The kitchen is well-appointed with granite countertops, a raised breakfast bar, and a stylish tile backsplash. A two-car garage provides ample storage, and the laundry room is conveniently situated on the main floor. Two additional bedrooms share a full bathroom, offering privacy and comfort for guests or family members. Tapestry offers a secure, well-kept environment with resort-style amenities such as a pool, clubhouse, fitness center, and more. Ideally located near Orlando’s top attractions, The Loop shopping center, the airport, and major highways, this home provides easy access to everything Central Florida has. Experience the Florida lifestyle with ease and elegance in this beautiful townhome. Don’t miss your chance to make it yours!

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

Listing Agent: Francisco Lara, Pa (407-319-4505)

Remarks: Charming 2-bedroom, 1.5-bath condo perfect for a first-time homebuyer, starter home, or investment opportunity. This inviting home features an updated kitchen with granite countertops, bright white cabinetry, and mix stainless steel appliances, offering a clean and functional space that opens to the main living area. The first floor features tile flooring throughout the living and dining areas, while both bedrooms are privately located upstairs with carpet flooring for added comfort. Enjoy relaxing outdoors on the spacious screened-in porch with a private rear view. Additional highlights include a 1-car garage and a location just steps from the community pool and clubhouse, making it easy to enjoy the neighborhood amenities. Great investment potential with rental rates in the area available. Conveniently located near shopping, dining, and major roadways.

Listing is courtesy of: HELLO SUNSHINE REALTY LLC (407-719-8932)

Listing Agent: Marissa Mcclung (407-719-8932)