Homes for Sale Near Osceola High School in Kissimmee - 153 homes

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: *Price Improvement!* Welcome to this stunning 5-bedroom, 4-bathroom Colonial-style pool home located in the highly sought-after gated community of Ashley Cove. This exceptional residence blends timeless elegance with modern upgrades, offering a truly one-of-a-kind living experience. From the moment you enter, you’re greeted by a grand spiral staircase and soaring high ceilings, complemented by rich hardwood flooring and exquisite, high-value chandeliers that add character and sophistication throughout the home. The spacious living room features a cozy fireplace, while large windows flood the home with natural light, highlighting the generous room sizes and thoughtful layout. The ground floor boasts a luxurious primary suite with two walk-in closets, a beautifully updated modern bathroom, complete with dual sinks, a large walk-in shower, and a relaxing soaking tub. The kitchen is both stylish and functional, featuring granite countertops, hardwood cabinetry, and stainless steel appliances including a range, microwave, dishwasher, and refrigerator. A renovated laundry room is also conveniently located on the main level. Upstairs, enjoy a unique movie theater room with a private balcony overlooking the expansive property and an additional bonus room! Situated on an oversized, fully fenced lot with no rear neighbors, the outdoor space offers privacy and tranquility. The screened-in pool and spa include a child safety net, creating the perfect setting for year-round enjoyment. Major updates include new pool tiles and pool re-surfacing in 2025. The property is surrounded by eight beautiful oak trees, three of which were recently removed in 2026 for hurricane safety. Additional features include a 3-car garage and numerous updates: new pool pump (2023), pool re-surfaced (2025), roof replacement (2019), updated A/C units (2018 & 2021), electrical updates (2025), new hot water heater (2026), and fresh interior paint (2025). Conveniently located near Lake Tohopekaliga, with easy access to the Florida Turnpike, and just minutes from Kissimmee, NeoCity, major attractions, shopping, and dining this home truly has it all. Schedule your showing today!

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Rocki Sanchez (407-738-7989)

Remarks: One or more photo(s) has been virtually staged. Seller is Highly Motivated – Bring All Offers! Welcome to the gated community of Windsor Point, where comfort, convenience, and natural beauty come together. This spacious 3-bedroom, 2-bath residence with a versatile flex room offers a thoughtfully designed layout ideal for both entertaining and everyday living. Upon entering the home, you’re greeted by a welcoming foyer that opens into a bright formal living room—perfect for hosting guests or creating a peaceful sitting area. The split floor plan provides privacy, while the expansive family room serves as the heart of the home, offering plenty of space for gatherings, movie nights, or relaxing after a long day. Sliding glass doors lead to a generously sized backyard, fully enclosed with durable vinyl fencing for privacy and security. Whether you envision weekend barbecues, a play area, space for pets, or a future pool, this yard provides endless possibilities. The home features easy-care ceramic tile flooring throughout—ideal for Florida living. The spacious kitchen is designed for functionality and flow, complete with abundant cabinetry, ample counter space, and an open layout that allows you to stay connected while cooking or entertaining. The flex room can easily function as a home office, workout room, craft room, or homeschool space. Prime Location: Located just 5 minutes from The Loop, featuring upscale shopping, restaurants, and a movie theater. Enjoy quick access to major highways, including Osceola Parkway, John Young Parkway, and the Florida Turnpike, for easy commuting. World-famous attractions such as Disney theme parks, Disney Springs, and Old Town are just 6–10 miles away. Orlando International Airport (MCO) is approximately 15 miles from the property. This home offers space, flexibility, and a highly desirable location within a secure community—making it an excellent opportunity for primary homeowners, second-home buyers, or investors alike. Schedule your private tour today to fully appreciate this home's charm!

Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)

Listing Agent: Tiffany Greer (407-709-0582)

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. 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: Feast your eyes on this Stunning 5BR/3BA pool home in the sought-after Gated Ashley Cove community. Here you can enjoy 2,896 sq ft of luxury. The home offers a desirable 3-way split-bedroom plan, a Formal living room with a wood-burning fireplace, a formal dining room, and a spacious family room. For those who work from home, there's a separate office with built-in shelving. The kitchen is well-appointed with beautiful granite countertops, a center island, and crown-molded cabinetry. Eat at the comfortable breakfast bar, the dinette, or the dining room. The master retreat boasts a tray ceiling, two walk-in closets, a garden tub, a separate shower, dual vanities, and a set of french doors that lead out to the covered lanai and screened pool. The spacious pool deck, adorned with beautiful brick pavers, is ideal for relaxing and entertaining. The new roof (2023) and AC (2025) provide peace of mind for years to come. Other improvements include: hot water heater (2020), exterior paint (2026), new light fixtures (2022), pool re-screen (2025), and newer appliances (2023 & 2026). The 12 ft ceiling and the 4 sets of french doors give this home a beautiful open appeal. The pre-wired surround sound speakers convey. This home is move-in ready and waiting for its next owner. All appliances convey. Minutes to Lake Toho, attractions, shopping, hospitals, and expressways.

Listing is courtesy of: FLORIDA REAL ESTATE PROPERTIES LLC (407-951-7810)

Listing Agent: Joyce Sanders (407-234-4680)

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: LOCATION, LOCATION, LOCATION! This fantastic property features a 2025 NEW manufactured home and is truly ready for move-in! ?It boasts three spacious bedrooms and two comfortable full bathrooms. Enjoy the sleek look and easy maintenance vinyl flooring throughout the entire home. ?A sliding door from the living area leads out to a relaxing patio—perfect for hosting barbecues and spending quality time with family and friends. The home also includes a spacious living and dining area, an eating space in the kitchen, and all appliances are included. ?Recent updates include a new drain field. The home is centrally located with incredibly easy access to shopping, restaurants, and the Orlando International Airport. ?Schedule your showing today and make this beautiful home yours! The seller is highly motivated.

Listing is courtesy of: CENTRAL REALTY GROUP AND PROPERTIES (407-582-9011)

Listing Agent: Bernardino Castorani (407-582-9011)

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: Experience resort-style living in the gated community of Tapestry. This stunning 3BR/2.5BA townhouse features a modern chef’s kitchen with state-of-the-art appliances, granite countertops throughout, and ample storage. Enjoy premium amenities including a luxury clubhouse, fitness center, and sparkling pool. Perfectly located and move-in ready—schedule your tour today!

Listing is courtesy of: REALTY HUB (407-900-1001)

Listing Agent: Ramesh Vanapalli (954-892-5648)

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: Discover this spacious 2-bedroom, 2-bathroom condominium located in a gated community in the heart of Kissimmee. Conveniently close to schools, grocery stores, major roads, and entertainment areas—including parks and attractions. The property features updated bathrooms and kitchen, a recently replaced electric water heater, and a fully functional A/C unit. There is no carpet throughout the unit, offering easy maintenance and a modern feel. With abundant natural light and a smart layout, this condo offers both comfort and functionality. Ideal for investors seeking strong rental potential and reliable passive income. Don't miss this opportunity!

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Gaby Castellanos (407-429-1076)

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: 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. 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)