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

Remarks: Investor special opportunity at 2460 Summerfield Way in Kissimmee. This 2-story townhouse offers immediate rental income with a tenant already in place paying $1,500 per month on a year-long lease, making it a turnkey addition to any investment portfolio. The property features 2 bedrooms, 2.5 bathrooms, and a functional layout designed for comfortable everyday living. The main level includes the shared living and dining areas, along with a conveniently located kitchen and half bath for guests. Upstairs, both bedrooms offer access to full bathrooms, creating a practical setup for residents, roommates, guests, or even a home office configuration. The patio provides additional usable outdoor space for seating, dining, or relaxing while remaining low maintenance. Investors will appreciate the major system updates already completed, including a new roof in 2024, a water heater that is only 1 year old, and an HVAC system replaced in 2022. These improvements help minimize near-term maintenance concerns and add long-term value to the property. Located in Kissimmee, the home offers convenient access to shopping, dining, schools, parks, major roads, and Central Florida attractions. The neighborhood provides a residential setting with everyday essentials nearby, making it an appealing option for both tenants and long-term investors seeking convenience and steady rental potential.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Thomas Nickley, Jr (407-629-4420)

Remarks: Beautiful and well-maintained single-family home located in a gated community in the heart of Kissimmee, Florida. This stunning property offers 3 bedrooms, a bonus room, 2 bathrooms, and a spacious 2-car garage. The home features 2 A/C units that are approximately one 1/2 year old, smart thermostats for energy efficiency and comfort, a central vacuum system, and a modern wall-mounted water heater. The interior doors and front door have also been freshly painted, giving the home a clean and updated appearance. Inside, you will find an open floor plan with vaulted ceilings and ceramic tile flooring throughout the home. The spacious family room and dining room combination create the perfect setting for entertaining and everyday living. The open kitchen includes an island with electrical outlets, a range hood, a bar, a wine rack, and stainless steel appliances. The bonus room can easily be used as a nursery, office, guest room, or additional bedroom. The primary bathroom features a double vanity, a walk-in closet, and a separate shower. Skylights provide beautiful natural lighting throughout the bathrooms and living areas. Step outside to your screened patio and enjoy breathtaking pond views with a relaxing fountain backdrop, peacecul outdoor setting perfect for morning coffee or evening relaxation. The backyard is surrounded by beautiful palm views, bringing the best of Florida living right to your backyard. Community amenities include a resort-style pool, basketball courts, a tennis court, a playground, and beautifully maintained common areas. Conveniently located just 15-20 minutes from Disney World, Disney Springs, SeaWorld, Universal Studios, International Drive, Downtown Orlando, and Orlando International Airport. Easy access to the Florida Turnpike, plus proximity to schools, shopping centers, restaurants, and hospitals. Schedule your private showing today and experience everything this beautiful home.

Listing is courtesy of: SIGNATURE BROKERS REALTY LLC (407-595-6820)

Listing Agent: Mickie Rodriguez (407-949-4902)

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 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: 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: 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: 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)

Remarks: Under contract-accepting backup offers. Take a look this furnished townhome in a gated community. The layout includes a 3 bed, 2 and 1/2 bath, a front portico, 1 rear balcony, and a rear entry 2 car garage. Downstairs you'll find the kitchen with granite countertops is also fully tiled and contains a large living space and convenient half bathroom. All of your bedrooms are located upstairs for your privacy and convenience.The master bedroom features walking closet and a large balcony perfect for your morning coffee.Tapestry offers 24 hours private security, a Resort style Club House like no other in the area, beach entry pool with slide and splash pad, grill area , fitness center, walking trails and more! Enjoy this beautiful property located just minutes from Orlando International Airport and the world-famous Disney and Universal theme parks. Schedule your appointment today!

Listing is courtesy of: YORK MILLS REALTY LLC (407-620-8528)

Listing Agent: Leo Shao (407-569-6769)

Remarks: Investor special! Great location! Location, Location, Location!!! This cute little house has newer roof, new plumbing, new electric lines, new appliances and new tiles throughout. This house has fence too. This house got lots of potentiality. Public records show 1 bedroom but it has 2 bedrooms and 1 bonus room that can be treated as additional bedroom (3rd Bedroom) and that brings up to total 780'. A few minutes away to Shopping, Banking, Super Markets, Hospital, Business Centers, Schools, Valencia Community College, Loop Mall, and Highways. All the information relating to this MLS Listing is intended to be accurate but cannot be guaranteed and must be verified by the buyer and buyer's agent. Motivated seller. NOT A SHORT SALE** NOT A BANK OWNED** OR NOT A FORECLOSURE** All Buyers Are Welcome! Don't miss this “Great Opportunity” to invest!! Opportunity knocks - ACT FAST!!!

Listing is courtesy of: PROFILES INTERNATIONAL REALTY (321-297-8161)

Listing Agent: Mohammed Hossain (407-925-3442)

Remarks: One or more photo(s) has been virtually staged. Positioned on an expansive 0.45-acre lot with no HOA in Kissimmee, this custom-built residence delivers space, privacy, and elevated finishes rarely found at this price point. Inside, the architecture is clean and intentional, highlighted by soaring ceilings, crown molding, and a seamless open layout designed for both everyday living and entertaining. At the center of the home is a fully upgraded chef’s kitchen, featuring premium granite countertops, custom cabinetry, and high-end built-in appliances including a double oven and integrated refrigerator, complemented by a functional butler’s pantry for added storage and prep space. The main living areas flow effortlessly, creating a bright and inviting environment with strong indoor-outdoor connectivity. The first-floor primary suite is designed for privacy and scale, offering a spacious layout, including an attached sitting room that can be customized to fit your needs and lifestyle, large walk-in closet, and a well-appointed bath with a soaking tub, oversized shower, and dual vanities. A dedicated front flex space provides versatility as a home office, study, or additional living area. Upstairs, three additional bedrooms are thoughtfully positioned along with two full bathrooms, including an en-suite located on the second floor, offering flexibility for multi-generational living or guest accommodations. The outdoor space is equally impressive, anchored by a large screened-in patio with elevated ceilings, ideal for year-round use. Beyond, the oversized backyard offers ample room to design a custom pool or outdoor retreat, all without the restrictions of an HOA. Located in a highly accessible area of Kissimmee, this home is just minutes from major roadways including the Florida Turnpike and 417, providing easy access to Lake Nona’s Medical City and NeoCity, a growing hub for technology and innovation. You’re approximately 25 minutes to Orlando International Airport, 30–35 minutes to Walt Disney World and major attractions, and about 20–25 minutes to Downtown Orlando. Everyday conveniences are close by with Publix, Walmart, The Loop shopping center, restaurants, and schools all within a short drive. For weekend getaways, Florida’s east coast beaches are roughly 60–75 minutes away. **UPGRADES LIST AVAILABLE UPON REQUEST**

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

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

Remarks: Charming 2-bedroom, 2-bath villa. Enjoy easy Florida living with a spacious screened porch—perfect for relaxing or entertaining—plus an enclosed area that serves as a convenient storage room. The kitchen features updated cabinets, and newer roof replace in 2025, offering added peace of mind. Conveniently located within minutes of Orlando International Airport, the Florida Turnpike, and SR-417, with major shopping plazas nearby. Plus, you’re just a short drive to Orlando’s world-famous attractions including Universal Studios, Walt Disney World, and SeaWorld.

Listing is courtesy of: FLORIDA PROPERTY HOMES (407-728-5650)

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

Remarks: JUST LISTED | FULLY REMODELED | NO HOA! Welcome to 501 W Sumner St, a stunning, move-in-ready property located right within city limits!! Features You'll Love! 5 Spacious Bedrooms! 4 Full Bathrooms; Bright Living & Formal Dining Areas, Private In-Law Suite with Separate Entrance (perfect for rental income or multi-generational living. Beautiful In-Ground Pool, Charming Front Porch! NO HOA – freedom and flexibility! This home has been completely remodeled, offering modern finishes, upgraded spaces, and a layout designed for both comfort and functionality. Whether you're looking for your dream home or an income-producing opportunity, this property checks every box. Prime location inside city limits – close to everything!

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

Listing Agent: Paola Almonte (407-968-7511)