Homes for Sale Near Osceola High School in Kissimmee - 149 homes

Remarks: This two-story, 3 bedroom, 2.5 bathroom townhouse in the gated community of Fiesta Key. The first floor features an open floor plan with tile flooring throughout, connecting the living room and dining area to the kitchen. The kitchen includes granite countertops, an island with seating space, wood cabinets, and stainless steel appliances. A screened porch with a storage room is locate off the back. All bedrooms and the laundry area are located on the second floor. The primary bedroom includes a walk-in closet and a private bathroom with a double sink granite vanity and a shower. The other two bedrooms share a second full bathroom, which also features a double -sink granite vanity, a tub, and a linen closet. Fiesta Key community amenities includes a fitness center, two pools, and a tennis court. The property is locate minutes away from Disney parks, Universal Studios, shopping centers, dining, schools, making a great option for a primary residence, vacation home, or investment property.

Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)

Listing Agent: Marggy Nieves (407-334-4149)

Remarks: Under contract-accepting backup offers. Discover your dream home in the heart of the desirable Kindred community. This expansive 5 bedroom, 3 bathroom residence offers 2,601 square feet of comfortable living space, perfectly positioned to provide unmatched views and lifestyle benefits. The home sits directly in front of a community park, offering a peaceful and scenic outlook right from your front door. The interior is designed for functionality and space, accommodating any lifestyle with ease. The backyard is truly the star of this property. Fully fenced for privacy and security, it has been transformed into an outdoor entertaining masterpiece. You will find a beautiful custom gazebo that serves as a tranquil retreat, plus an impressive outdoor kitchen setup that makes hosting gatherings, celebrations, and weekend cookouts an absolute breeze. Do not miss this unique opportunity to own a home that perfectly combines modern comfort with an incredible outdoor lifestyle. Schedule your showing today.

Listing is courtesy of: REALTY ONE GROUP MAGIC CITY (407-589-9080)

Listing Agent: Mitch Susana, Llc (407-781-6586)

Remarks: Welcome to this beautifully maintained corner residence located in the highly sought-after gated community of Tapestry in Kissimmee. The seller is offering $12,000 towards the Buyer’s closing costs with a full price contract, making this an incredible opportunity! 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: Welcome to 2324 Haley Ct - a charming 3-bedroom, 2-bath home offering 1,853 sq/ft of living space on an oversized .26-acre lot in the established Renee Terrace community. Built in 1973, this property features a spacious layout, a 2-car garage, and several important major updates already completed, including re-pipe in 2022, as well as A/C and water heater replacements in 2021. The home offers excellent potential for buyers looking to personalize and add their own finishing touches, as some interior upgrades may still be desired. Conveniently located near The Loop shopping, dining, and entertainment, with easy access to major roadways. Approximately 25 minutes to Walt Disney World Resort and 20 minutes to Orlando International Airport - MORE PICTURES TO COME SOON!

Listing is courtesy of: EXIT GLOBAL REALTY (407-725-7180)

Listing Agent: Hugo Hernandez (407-716-5594)

Remarks: Virtually Staged. Price Reduced in the gated Tapestry community. This move-in ready 4-bedroom, 3.5-bath home offers over 2,300 square feet of stylish and functional living space with a bright open-concept layout designed for entertaining and everyday comfort. The spacious kitchen features granite countertops, stainless steel appliances, modern cabinetry, and a large center island that flows seamlessly into the dining and living areas. Upstairs, the private primary suite includes a walk-in closet and ensuite bath with dual vanities and a spacious shower. A versatile loft and additional bedrooms provide flexible space for a home office, media room, play area, or guest accommodations. Enjoy indoor-outdoor living with a covered rear porch and fully fenced backyard perfect for relaxing or weekend gatherings. Residents enjoy resort-style amenities including a clubhouse, pool, fitness center, sidewalks, and 24-hour gated entry. Conveniently located near shopping, dining, major highways, Orlando International Airport, and Orlando attractions. Now offered at an improved price schedule your private showing today.

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

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

Remarks: Some houses check the boxes. This one feels like home. Nestled in a desirable Kissimmee location, this beautifully maintained residence offers the perfect combination of comfort, style, and everyday convenience. From the moment you walk through the front door, you'll appreciate the bright, open living spaces designed for both relaxing evenings and making memories with family and friends. The spacious layout flows effortlessly, creating a warm and inviting atmosphere throughout. Whether you're preparing meals in the kitchen, gathering around the dining table, or enjoying a quiet morning coffee, every space is designed to make daily living easy and enjoyable. Step outside and discover the perfect spot for weekend BBQs, family gatherings, or simply unwinding after a long day. With shopping, dining, schools, parks, and major roadways just minutes away, you'll love the convenience of this central location. Gated community with GUARD includes pool, playground and more. If you've been searching for a place that combines comfort, charm, and a true sense of home, 2520 Nouveau Way may be exactly what you've been waiting for. Schedule your private showing today and see why you'll want to call this one yours. UPGRADES: Exterior Paint done November 2025. Pre-wire for surround sound for the back patio, family room and master bedroom. Gutters. Pool Pre wire.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Fatima Cabral Mendonca Leefers (407-552-1890)

Remarks: Welcome to this 3-bedroom, 2-bathroom home located in a gated community in the heart of Kissimmee, Florida, just minutes from The Loop, a popular shopping, dining, and entertainment destination. Enjoy convenient access to Walt Disney World (approximately 25 minutes) as well as Universal Orlando and Central Florida’s world-famous theme parks. This move-in ready home features a desirable split floor plan with spacious living areas and thoughtful updates throughout. Inside all appliances are brand new. Brand new floor. You will find fresh exterior and interior paint, and a refreshed front door that give the home a clean and welcoming feel. The layout offers generously sized bedrooms, along with a kitchen and family room combination that creates a comfortable space for gathering and entertaining. A formal living and dining area provides additional flexibility and can easily function as a home office, flex space, additional living area, or hobby room. Other Residents of this gated Kissimmee community enjoy access to neighborhood amenities including a community pool, playground, and clubhouse, adding to the convenience and lifestyle this location offers. With easy access to shopping, dining, major roadways, and Central Florida attractions, this Kissimmee home offers comfort, convenience, and the opportunity to make it your own. LOW HOA. Call to schedule your private showing!

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

Listing Agent: Ekramul Chowdhury (407-360-8991)

Remarks: Under contract-accepting backup offers. Welcome to refined lakefront living in the sought-after Regal Bay community on the shores of Lake Tohopekaliga. Perfectly positioned at 1475 Riviera Drive, this exceptional 3-bedroom, 2.5-bath residence offers a rare combination of panoramic water views, private boating access, and tranquil outdoor living—and is being sold furnished for a seamless move-in experience. From the moment you arrive, you’re greeted by a serene front porch overlooking the sparkling waters of Lake Toho, setting the tone for the peaceful lifestyle this home delivers. Inside, the layout is designed to capture water views from multiple vantage points, creating a seamless connection between indoor and outdoor living. The rear of the home opens to a spacious porch with stunning, unobstructed lake views—ideal for morning coffee, evening sunsets, or entertaining guests. Boating enthusiasts will appreciate the private dock and boat lift, providing direct access to this highly desirable, skiable lake known for its world-class fishing and recreational boating. Additional highlights include a charming secondary porch off the dining room, perfect for quiet moments, along with well-appointed living spaces that balance comfort and functionality. Whether you’re searching for a full-time residence or a turnkey waterfront retreat, this property offers a unique opportunity to enjoy true Florida lakefront living with both sunrise and sunset views over Lake Toho.

Listing is courtesy of: TOHO REALTY GROUP, LLC (407-437-2893)

Listing Agent: Kerriann Sullivan (407-437-2893)

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 newly painted 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: 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: 3-bedroom, 2-bath home with a screened-in pool and pond view. No HOA. Conveniently located near shopping, Florida’s Turnpike, theme parks, and about 30 minutes to downtown Orlando.

Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)

Listing Agent: Troy Funk (941-241-3850)

Remarks: Townhome available and ready to move in, featuring 3 bedrooms, 2.5 bathrooms, and a one-car garage, located in the gated community of Flora Ridge, conveniently near the Loop. The welcoming entry opens to a well-appointed kitchen with breakfast bar, seamlessly flowing into the open-concept living room and dining area—perfect for everyday living and entertaining. Upstairs, you’ll find three spacious bedrooms, two full bathrooms, and a built-in workstation ideal for remote work or study. Enjoy close proximity to Shopping, Schools, Dining, and more. Schedule your private showing today!

Listing is courtesy of: BROKERS REAL ESTATE GROUP INC (407-770-1464)

Listing Agent: Rich Canelon (407-341-4035)

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

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

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

Remarks: Under contract-accepting backup offers. Brand New Interior Paint--Move in Ready! Welcome to the beautifully maintained 3 Bedroom 2-Bathroom home located in the desirable gated community of Cypress Reserve! Featuring an open concept layout with wood flooring throughout, crown molding and window treatments! This home offers both style and comfort on a gorgeous, oversized lot! The kitchen is fully equipped with a refrigerator, dishwasher, oven and microwave and showcases Corian countertops, tiled backsplash, maple cabinetry, and a closet pantry. An eat-in area just off of the family room creates the perfect space for casual dining and everyday living. The spacious primary suite and secondary bedrooms offer a functional split floor plan. A 2023 AC and 2018 ROOF provides a peace of mind. Washer and dryer convey with the sale. Step outside and enjoy a large, enclosed lanai overlooking an expansive backyard--ideal for entertaining or relaxing year-round. Move in ready and conveniently located near shopping (The Loop), dining, and major roadways. Come and see this home today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Catherine Lambert Pa (407-908-2525)

Remarks: INVESTORS OPPORTUNITY !!!! TENANT OCCUPIED. Fully remodeled, this inviting single-family home at 709 S Dillingham Ave in Kissimmee is designed for comfort and flexibility. The thoughtfully updated interior offers modern finishes throughout, creating a fresh and welcoming feel from the moment you arrive. Ideal for multi-generational living, the home includes a private mother-in-law suite with 2 bedrooms and 1 bathroom, perfect for extended family or guests while still maintaining privacy or for a great rental income. Centrally located near downtown Kissimmee, shopping, dining, schools, and major roadways. Enjoy peace of mind with a beautifully updated home ready for its next chapter. A wonderful opportunity to settle into a space where everyone feels at home. Buyer to verify all measurements and information.

Listing is courtesy of: GPS PROPERTY GROUP INC. (407-439-2527)

Listing Agent: Abel Jimenez (407-452-4119)

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: Opportunity is knocking with this stunning property nestled within the highly sought-after Stonefield community in Hunter’s Creek. This is a rare chance to own a spacious, updated townhome with an ASSUMABLE FHA LOAN at an incredible 3.375 interest rate, a true game changer in today’s market! But wait that’s not all! This 2-bedroom, 2-bath home with a 1-car garage features three additional flex rooms, offering incredible versatility for your lifestyle. Whether you need a private home office, formal dining room, cozy den, or guest suite, this floor plan easily adapts to your needs. Enjoy the perks of modern living and energy efficiency with a paid off solar energy system providing substantial savings, plus a newer 2021 energy-efficient A/C unit. Inside, you’ll find tile and laminate flooring throughout, appliances and an interior laundry room with washer & dryer included along with built-in cabinetry for convenient storage. The primary suite offers abundant natural light, a spacious walk-in closet, private ensuite bathroom featuring double vanities and an oversized walk-in linen closet. Upstairs, you’ll discover two large bonus rooms perfect for an office, studio, guest quarters or extra storage that many homes lack. The second bedroom is located on the main floor across from the updated second bathroom, which, like the primary, features stone countertops and modern finishes. Stylish lighting fixtures throughout the home add a contemporary touch, making this property truly move-in ready. Residents of Stonefield enjoy a secure gated community with resort-style amenities, including resort style pool, clubhouse, fitness center, tennis courts, fishing dock and walking / biking trails surrounded by exotic landscaping. Located just 15 minutes from Disney, Universal, Orlando’s top attractions, 20 minutes from Orlando International Airport, hospitals, schools, medical offices, markets and steps from The Loop’s dining with plenty of shopping for everyday needs. This home perfectly blends convenience, comfort and lifestyle. Live a life of ease, style and abundance of opportunity.

Listing is courtesy of: LPT REALTY LLC (386-204-6398)

Listing Agent: Scarlett Napolitano (407-808-6757)

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: This inviting 3-bedroom, 2-bath condo in Flora Ridge offers a bright and spacious layout designed for comfortable everyday living. The living and dining areas flow seamlessly into a screened-in balcony, while the kitchen features ample cabinet space and a practical layout. All three bedrooms are generously sized, with carpeted flooring for added comfort, and both bathrooms are tiled for easy maintenance. Located near the community pool and just minutes from shopping, dining, schools, and major roads, this condo offers convenience and a family-friendly environment in a well-maintained and secure gated community.

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

Listing Agent: Mariana Nossa (407-455-9565)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained single-story end-unit villa, offering effortless living in a peaceful community setting. This 3-bedroom, 2-bath home features a desirable split floor plan, providing privacy and comfort for every member of the household. Abundant natural light fills the open-concept living and dining areas, creating a warm and inviting space ideal for everyday living or entertaining. The functional kitchen is equipped with stainless steel appliances, ample cabinetry, and a practical layout perfect for cooking and hosting. The spacious primary suite includes a private bath and generous closet space, while the additional bedrooms are well-appointed for guests, family, or a home office. Tile flooring in the main areas and luxury vinyl plank flooring in key spaces ensure both durability and style, and the washer and dryer are included for added convenience. Relax outdoors in the screened-in lanai overlooking a surprisingly spacious backyard, offering room for gardening, play, pets, or peaceful relaxation. Enjoy low-maintenance living with access to community amenities including a sparkling pool and playground. Located just minutes from The Loop, you’ll enjoy close proximity to premium shopping, dining, entertainment, and major highways, making commuting and daily errands a breeze. This villa offers the perfect blend of comfort, convenience, and low-stress living—ready for you to move right in.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Charisse Elliott (321-461-5055)