Homes for Sale Near Osceola High School in Kissimmee - 57 homes

Remarks: EXCEPTIONAL INVESTMENT OPPORTUNITY OR DREAM VACATION HOME! Welcome to 2260 San Vital Dr #108, a stunning and spacious 4-Bedroom, 3-Bathroom residence perfectly situated in the world-class, guard-gated resort community of Venetian Bay Villages in Kissimmee, Florida. This property offers the perfect blend of comfort, style, and high-income potential in one of Central Florida’s most sought-after short-term rental zones. UNIQUE DUAL-MASTER FLOOR PLAN: This rare and highly functional layout is a favorite among vacationers and large families. It features TWO PRIMARY EN-SUITES: one conveniently located on the first floor for easy access, and a second private master suite on the upper level. This configuration ensures maximum privacy and flexibility for multi-generational living or groups of up to 10 guests. The ground floor boasts an open-concept living and dining area with tall ceilings and plenty of natural light, flowing into a fully-equipped kitchen with a breakfast bar. Two additional guest bedrooms share a third full bathroom, providing a comfortable and balanced living space. RESORT-STYLE LIVING AT ITS FINEST: Living in Venetian Bay Villages feels like a permanent vacation. This Mediterranean-inspired community is meticulously maintained and offers an unparalleled amenity package included in your HOA fee: 24/7 GUARD-GATED SECURITY: Peace of mind with a manned entrance and security patrol. FOUR SPARKLING SWIMMING POOLS: Including a large heated main pool near the clubhouse and three satellite pools throughout the village. ELITE CLUBHOUSE: Featuring a state-of-the-art fitness center, a private movie theater, a game room/arcade, and a business center with high-speed internet. SPORTS & RECREATION: Professional-grade tennis courts, basketball courts, and sand volleyball courts. FAMILY-FRIENDLY: Multiple playgrounds, picnic areas, and scenic walking trails around serene community ponds. STRATEGIC LOCATION IN THE HEART OF THE MAGIC: Location is everything! This property is strategically positioned for maximum occupancy and convenience: MINUTES FROM DISNEY: Less than 10-15 minutes from Walt Disney World Resort main gates. CLOSE TO ATTRACTIONS: Short drive to SeaWorld, Universal Orlando Resort, and Disney Springs. SHOPPER’S PARADISE: Located just around the corner from The Loop Shopping Center, featuring premier retail, a multi-screen cinema, and dozens of popular dining options. EASY TRAVEL: Quick access to Osceola Parkway, John Young Parkway, and I-4. Only 20 minutes from Orlando International Airport (MCO). INVESTOR HIGHLIGHTS: This property is TURNKEY and ready for immediate occupancy or rental. Short-Term Rentals (Airbnb/VRBO) are fully permitted by the association. The HOA is comprehensive and covers: EXTERIOR MAINTENANCE, ROOF REPLACEMENT, LANDSCAPING, TRASH REMOVAL, WATER/SEWER, AND 24-HOUR SECURITY. This significantly lowers the owner's insurance costs and simplifies management. Whether you are looking for a high-performing asset to add to your short-term rental portfolio or a luxurious primary residence where every day feels like a getaway, this Venetian Bay gem is a must-see. Properties with 4 bedrooms and dual suites are in high demand and do not last long on the market. SCHEDULE YOUR PRIVATE TOUR TODAY AND START LIVING THE FLORIDA LIFESTYLE!

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

Listing Agent: Marcos Urbina (321-388-3150)

Remarks: Under contract-accepting backup offers. This beautiful single family home is just a few minutes away to Osceola High School, downtown and Kissimmee Lakefront. Great location close to shopping areas, access to mayor roads and schools. NO HOA, NO CDD. This property is well conserved with an oversize lot ,nice sunny backyard with fruits trees, a large patio, aboveground pool and cover lanai provides plentiful space for gardening and entertaining. The garage is converted into a 4th bedroom but can be easily convert back to a full garage and still have the a garage door. New roof installed in 2023.

Listing is courtesy of: ONE TEAM REALTY (407-530-5006)

Listing Agent: Yolanda Soto Rosado (407-530-5006)

Remarks: Spacious 4-bedroom, 3-bath single-family home on a generous 0.31-acre corner lot with no HOA! This versatile property offers an ideal layout with an eat-in kitchen, inside laundry, and a welcoming front bonus/sitting room perfect for a home office, reading area, or flex space.The split-style floor plan provides comfortable living for multi-generational households, or rental opportunities. Located within a block away from AdventHealth, making it especially appealing for healthcare professionals, traveling nurses, or long-term rental potential. Conveniently close to shopping, dining, and everyday amenities. Zoned for professional office use, offering rare flexibility for buyers seeking a live/work opportunity, small business location, or future investment potential. A unique opportunity for first-time buyers, investors, or entrepreneurs looking for space, location, and versatility.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Carlethia Burnette (407-970-7902)

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

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

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

Remarks: Welcome to this beautifully located 3-bedroom, 2.5-bath condo in the desirable Villas of Estancia community in Kissimmee, FL. Perfectly situated across from the community pool, this home offers convenience and comfort in one of the area’s most accessible locations. Enjoy easy access to a wide variety of shopping, dining, and everyday essentials just minutes away. With a functional layout and spacious bedrooms, this condo is ideal as a primary residence, vacation home, or investment opportunity.

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

Listing Agent: Monica Fehlberg (407-497-9710)

Remarks: PRICE REDUCTION! SELLER MOTIVATED! Welcome to Woodland Creek. This beautifully maintained 4-bedroom, 2.5-bath home offering space, comfort, and modern upgrades throughout. A versatile first-floor bonus room provides the perfect option for a fifth bedroom, home office, gym, or playroom, while the main living area is ideal for entertaining and family gatherings. The updated kitchen features quartz countertops, stainless steel appliances, and two walk-in pantry closets, delivering exceptional storage and functionality. A nearby laundry room and enclosed porch add everyday convenience and additional living space. Upstairs, all four bedrooms are generously sized, each capable of accommodating king-size beds. The spacious primary suite includes dual sinks, a soaking tub, separate shower, and two walk-in closets. A second-floor loft offers additional flexible space for a family room, office, or study area. Enjoy the large backyard with mature trees, patio space, and plenty of room for outdoor entertaining. Major updates include roof (2021), two Carrier A/C units (2023 & 2024), exterior paint (2024), bathroom upgrades (2024), kitchen updates (2020), vinyl fencing, and LVP flooring. Conveniently located near shopping, dining, Florida Turnpike, Osceola Parkway, and major theme parks. Property is also approved for short-term rental.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Roland Barcenilla (407-480-6438)

Remarks: Under contract-accepting backup offers. The only corner townhome currently available in the community, this 3-bedroom, 2.5-bath residence with a rear-entry 2-car garage offers 1,700 square feet of heated living area, making it the largest townhome floor plan in Tapestry. As a corner unit, the home enjoys enhanced privacy with no neighboring unit on one side and additional natural light throughout. The interior features no carpet, with vinyl flooring on the staircase and throughout the second level, delivering a modern, low-maintenance living environment. The bathrooms are finished with quartz countertops, adding a clean and contemporary feel. The primary (master) bedroom includes a private balcony located at the front of the home, a rare feature within the community and an ideal space to enjoy morning coffee, relaxation, or any activity you prefer in a private outdoor setting. The two-car garage is conveniently located at the rear of the home, providing easy access while maintaining a clean and attractive front elevation. Situated within the gated Tapestry community with 24-hour guard service and controlled access, residents enjoy walking trails, fountains, parks, a community pool, and well-maintained common areas. The property is conveniently located near shopping, dining, major highways, and Central Florida attractions, offering an excellent combination of privacy, space, and accessibility.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Jorge Gutierrez Freites (786-800-6493)

Remarks: 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: $3,000 Closing Cost Credit! WOW! Charming home in the desirable Herons Landing community featuring abundant natural light, an open layout, and inviting living spaces. Bright kitchen perfect for entertaining plus a peaceful backyard ideal for relaxing. Very low HOA fee. Conveniently located near shopping, dining, schools, major highways, and ~20 minutes from Disney. Enjoy comfortable Florida living in a prime Central Florida location. Some photos virtually staged; home sold unfurnished.

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

Listing Agent: Marina Shmakova (407-965-9830)

Remarks: Fully Furnished & Move-In Ready Villa!! Welcome to this beautifully updated 2-bedroom, 2-bath villa located in the heart of Kissimmee! This turnkey home is being sold fully furnished, making it the perfect opportunity for first-time buyers, seasonal residents, or investors looking for an immediate rental. Step inside to find a bright and open layout featuring tile flooring throughout, an updated kitchen, and a comfortable living space ready to enjoy from day one. Recent improvements include a new roof, giving peace of mind for years to come. Enjoy low-maintenance living in a well-established community offering amenities such as a pool and tennis courts, all while being just minutes from shopping, dining, and entertainment at The Loop, major highways, and area attractions. Whether you’re looking for a primary residence, vacation home, or income-producing property, this one checks all the boxes: Prime location, Fully furnished, Move-in ready, Incredible value. Seller is motivated—schedule your showing today!

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

Listing Agent: Angie Pereira (407-721-8945)

Remarks: Under contract-accepting backup offers. Fantastic Regal Oak Shores Pool Home located on more than a half-acre of tropical and oak forest. 4 bedrooms/ 2 full baths. NO HOA! The pool is completely screened in, with a large entertaining area, including a generous covered portion and 4 access points. At any time of day, the home is light, bright, and welcoming. Lake Toho (across the street and 10 minutes from the access point) is Florida's 4th largest lake! Lake Toho is known to be the top destination for outdoor recreational sports, including Bass fishing, boat ramps, kayaking/canoeing, and airboats. Close to all the theme parks and entertainment destinations, including some of the top dining establishments in the nation. Super quiet neighborhood on a dead-end street that has no ambient lighting for amazing stargazing and late-night dips in the pool. Located about 25 minutes from Downtown Orlando, but with very close access to Florida's Turnpike and 429. Home has a NEW ROOF.

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

Listing Agent: Eric Rollings (407-256-2470)

Remarks: Welcome to the established, sought after community of Kings Point! With larger lots, and NO HOA, neighborhoods like this are hard to find in today's market. This home sits on just over a third of an acre and has beautiful, mature oak trees. It is a 3 bedroom, 2 bathroom home with an open floor plan that offers plenty of space for the family. A split bedroom plan offers a little extra peace for the primary bedroom. The skylight right inside the front door offers beautiful natural light for the living area. A sliding glass door takes you out to the gigantic screened in porch that overlooks the spacious back yard. The home also features a 2 car garage. The roof was replaced in 2021 and the water heater is brand new. While tucked away down Kings Highway, the home is not far from the turnpike, which makes commuting a breeze.

Listing is courtesy of: ALL STAR PROPERTIES OF CENTRAL (407-846-9100)

Listing Agent: Kevin Waldbieser (407-460-7993)

Remarks: Huge Price Reduction! 2 Bedrooms, 2 baths, living room, dining room, Porch, 2-car garage, plus parking for extra cars; Community allows! RV or a Boat, NOA HOA! LOT INCLUDED! Super Well Located! walking distances to the mall (The Loop), Financial institutions, Church, Bus stop, easy train commute, Hospitals, Schools. Best prices in town, sellers are super motivated!

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

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

Remarks: FULLY FURNISHED and ready to move in! The perfect vacation home or permanent getaway. A television comes complimentary, as do various appliances. Community features a large lake with a fountain and resort-style lounge chairs on a custom patio. The downstairs master bedroom suite and two bedrooms complete the upstairs. Separate bathrooms for each floor as well. Large sofas, TV, beautiful dining room table, we could go on and on! Truly a must-see to appreciate! Exclusive community with mannedgates functioning 24/7. Quiet area with picturesque views and scenic streets. Be the envy of your old neighbors and the best friend of your new ones - own today! Buyers should independently verify HOA dues and room measurements.

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

Listing Agent: James Williams Iii, Pa (321-402-6261)

Remarks: Welcome! Enjoy no rear neighbors forever, and a low-key HOA, with this well-appointed home, which offers five spacious bedrooms, four and a half bathrooms, and exceptional flexibility for family living, hosting guests, or creating dedicated work and relaxation spaces. The open floor plan boasts 4,964 square feet, with high ceilings, a gourmet kitchen with premium finishes, and multiple living areas designed for comfort and entertaining. A dedicated theater room can easily serve as a sixth bedroom, while the oversized 3-car garage provides ample storage. Each bedroom offers versatile options for family, home offices, or guest quarters, and generous square footage creates a natural balance between shared spaces and private retreats. Nestled on a 0.54-acre lot in a small, private gated community, this property combines privacy and convenience—located near shopping, lakefront parks, quality schools, SunRail, and minutes from charming downtown Kissimmee. Schedule your private tour today!

Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)

Listing Agent: Joseph Doher (407-203-0007)

Remarks: Hot water heater and stove are gas. Will not qualify for FHA loans- condo complex is not on FHA approved condo list. Community does not allow for short term rentals. Please check with property management company for pet restrictions. Please use "As-Is" FR/BAR contract. Text the listing agent to set up an appointment.

Listing is courtesy of: R LUGO REALTY (407-346-9920)

Listing Agent: Rosa Hernandez (407-346-9920)

Remarks: Welcome to this beautifully presented pool home in Kissimmee! This spacious residence showcases the kitchen featuring elegant gold fixtures and sleek stainless steel appliances, including a range, refrigerator, dishwasher, and microwave. Designed for both comfort and entertaining, the home offers a bright living room and a cozy dinette space. Enjoy the clean, modern feel of no carpet throughout, complemented by stylish flooring and ceiling fans in several rooms for added comfort. Both bathrooms have been tastefully updated, enhancing the home’s contemporary appeal. Step outside to a large screened-in patio overlooking a sparkling open-air pool—perfect for relaxing or hosting gatherings. The fully fenced backyard adds an extra layer of privacy, making this home a true retreat.***Home square footage, taxes, lot sizes, and schools; are to be independently verified.***

Listing is courtesy of: ALLEGIANT MANAGEMENT GROUP INC (407-557-3164)

Listing Agent: Elizabeth Santiago Moyet (321-231-2105)

Remarks: This beautiful 3-bedroom, 2-bathroom home with a spacious 2-car garage is located in the highly sought-after gated community of Stonefield in Kissimmee. Designed for both comfort and convenience, this well-maintained property offers a bright and open floor plan, perfect for modern living. The home features generous living spaces with tile, a functional kitchen ideal for entertaining, and a private primary suite with ample closet space. The additional bedrooms are perfect for family, guests, or a home office. Residents of Stonefield enjoy access to a variety of resort-style amenities, including a sparkling community pool, fully equipped fitness center, tennis courts, and a playground. The gated entrance provides added peace of mind, while the community’s prime location offers easy access to theme parks, major highways, airport and walking distance to the Loop shopping plaza. Whether you're looking for a primary residence or an investment opportunity, this home offers the perfect blend of comfort, style, and community living. New Roof 2018. Schedule your showing today.

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

Listing Agent: Blanca Hernandez, Llc (407-493-9895)

Remarks: This 1-bedroom, 1-bathroom condo is in excellent condition and features a private balcony, perfect for relaxing at home. The open layout and well-kept interiors make it move-in ready and easy to personalize. The kitchen includes appliances in perfect condition. Located in a convenient area of Kissimmee, you’re just minutes from schools, shopping centers, restaurants, hospitals, pharmacies, banks, and local stores. The community is well-organized and professionally managed, keeping common areas maintained and ensuring a smooth living experience. This condo offers the perfect combination of comfort, convenience, and practicality—ideal for anyone looking for a move-in ready home in a great location. An appointment must be scheduled at least 24 hours in advance. There is an administrative fee payable to the association that the new owner must pay. This is an investment property. The HOA fee includes water, sewer, Wi-Fi, trash, and pest control.

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

Listing Agent: Marianna Spinelli (786-447-1655)