Homes for Sale Near Osceola High School in Kissimmee - 91 homes

Remarks: This cozy Villa/Townhome offers 2 bedrooms and 2 full bathrooms, with 930 square feet of living area in the hearts of Kissimmee. This home features open floor plan, ceramic tiles flooring throughout, screened & covered front entry, living/dining combo, skylights in kitchen, inside separate laundry, nice outside sitting area, large vinyl fenced yard, low HOA, and Taxes. Enjoy the fresh air or cool off in the fenced in backyard. Property located very close proximity to Schools, Public Transportation (junction of public bus), Dining, Shopping, Banking, Loop Mall, Wal-Mart, Hospitals, Doctors Office, Major Roads (US 192, Osceola Parkway, John Young Parkway) and Major Attractions. This Townhouse is in great shape and recently updated plumbing system. An excellent opportunity for the first time homebuyer or investor. *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. 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. BACK ON THE MARKET! Spacious and VERY WELL-MAINTAINED 3-bedroom, 2-bath condo located on the 2nd floor in the desirable gated community of Flora Ridge in Kissimmee. This inviting condominium features wood-style flooring in the open great room, tile in the wet areas, and cozy carpet in the bedrooms. The split floor plan offers added privacy, with the primary suite separated from the other two bedrooms. The primary ensuite includes dual sinks, a private water closet, and a sleek walk-in shower—perfect for those who prefer ease of access and modern comfort over a traditional bathtub. The bright kitchen is equipped with all stainless steel appliances, lots of cabinets and counter space, a pantry closet, and a convenient washer and dryer area discreetly enclosed by a pocket door. Open both French doors to enjoy the outdoors from your screened-in balcony, perfect for relaxing or entertaining. Flora Ridge has fantastic amenities including a community pool, a gazebo, and serene waterfront walking path ideal for peaceful strolls and sunset views. Conveniently located within 3 minutes of Osceola Parkway, 7 minutes from The Loop shopping centers, and about 2 miles from the 417 Toll; this home provides easy access to major roads, schools, restaurants, and shopping areas. Majestically set away from the hustle and bustle, yet close enough to everything you need!

Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)

Listing Agent: Luz Lovera (407-325-5027)

Remarks: One or more photo(s) has been virtually staged. Welcome to 2365 Rapollo Drive, located in the highly sought-after gated community of Tapestry in Kissimmee! This beautifully maintained residence offers the perfect blend of comfort, style, and convenience. Featuring a spacious open-concept floor plan, this home is ideal for both everyday living and entertaining. The chef-inspired kitchen boasts modern cabinetry, granite countertops, stainless steel appliances, and a large center island overlooking the living and dining areas. Natural light fills the home, highlighting the thoughtfully designed layout and generous living spaces. The primary suite offers a with a walk-in closet and an ensuite bath complete with dual vanities and a spacious shower. Additional bedrooms provide flexibility for guests, a home office, or growing needs. Step outside to the fenced backyard space perfect for relaxing evenings or weekend gatherings. Residents of Tapestry enjoy resort style amenities including a clubhouse, sparkling pool, fitness center, and 24hr gated/guarded security. Conveniently located near The Loop shopping center, major highways, dining, and just minutes from world-famous attractions and Orlando International Airport. Don’t miss this opportunity to own in one of Kissimmee’s premier communities. Call to schedule your private showing today! Virtual tour available (English): https://youtu.be/g8VTYhJaErk . Virtual tour available (Spanish): https://youtu.be/MxjL10fnLpE

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

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

Remarks: 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: Under contract-accepting backup offers. Fully renovated from top to bottom, this 4-bedroom, 3-bath home offers 2,760 square feet of thoughtfully redesigned living space on a spacious .35-acre cul-de-sac lot — with no HOA. From the moment you enter, the home makes a statement. A striking glass staircase sets the tone, adding architectural interest and modern edge that immediately separates this home from the ordinary. An abundance of newly installed lighting fills the space with bright, natural warmth, while wide-plank luxury vinyl flooring runs seamlessly throughout for a clean, cohesive look. The kitchen was designed to impress and perform — featuring brand-new cabinetry, sleek quartz countertops, stainless steel appliances, and a generous island that anchors the room. It flows effortlessly into the open-concept living area where a remodeled fireplace adds warmth and balance to the contemporary finishes. The primary suite feels like a private retreat. With two access points — including a dramatic spiral staircase — the space offers flexibility and character rarely found at this level. The spa-inspired primary bath delivers a true oasis feel, complete with a freestanding soaking tub and dual shower heads designed for a luxurious, everyday escape, while each bathroom showcases brand-new custom tile showers, modern vanities, and quartz countertops that feel straight out of a design magazine. All four bedrooms offers comfortable, usable space, and each includes a custom closet system for elevated organization and functionality. Major updates have already been handled: brand-new roof, fresh interior and exterior paint, and a newly resurfaced pool provide both style and peace of mind. Step outside to a large covered patio overlooking the pool and jacuzzi — a true Florida backyard built for entertaining or unwinding year-round. The oversized driveway and 2-car garage allow for multiple vehicles, guests, or recreational toys, while the expansive lot still leaves room to breathe. Architecturally distinctive, fully updated, and positioned on a generous lot in a prime area, this is the kind of home that stands out — especially at this price point. Experience it in person and see why it feels different the moment you walk in.

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

Listing Agent: Rosemary Camilo Diaz (407-791-7152)

Remarks: Full of old-school charm and lovingly maintained by the same family since new, this inviting 3-bedroom, 2-bath home offers comfort, character, and an unbeatable central location. From the moment you arrive, you’ll appreciate the pride of ownership and timeless appeal throughout. Inside, the home features a warm and welcoming layout highlighted by a cozy wood-burning fireplace—perfect for relaxing evenings. The functional floorplan includes an inside utility area for added convenience, while thoughtful updates such as a tankless water heater and an updated electrical breaker box provide peace of mind. Step outside to enjoy a fully fenced backyard, ideal for pets, play, or entertaining. The covered and screened back porch creates the perfect space to unwind year-round while enjoying the outdoors in comfort. A carport with additional storage above offers practical space for vehicles and extra belongings. Located just minutes from the hospital, downtown, Amtrak, the bus station, and SunRail, this home offers easy access to everything you need while maintaining a quiet, established neighborhood feel. A rare opportunity to own a well-cared-for home with character, updates, and a prime location—schedule your showing today!

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: WOW! Highly Convenient First-Floor Condo in Prime Kissimmee Location! This exclusive first-floor condominium offers a functional and well-designed layout, perfect for comfortable living or investment. Upon entry, you are welcomed by a bright and inviting living area featuring large windows that fill the space with natural light and open to a private balcony with peaceful green views, ideal for relaxing or enjoying outdoor dining. The fully equipped kitchen boasts stainless steal appliances, spacious cabinetry, Tile in the kitchen, Livingroom, and hardwood style tile flooring in the bedrooms, seamlessly blending style, and functionality “NO CARPET”. Every detail of this home has been thoughtfully designed to support a relaxed and comfortable lifestyle. Community amenities include private parking, 24-hour security, a clubhouse, and a resort-style swimming pool. Enjoy the convenience of an urban lifestyle while maintaining the tranquility of open views and well-maintained surroundings. Strategically located in the heart of Kissimmee, just minutes from US-192, with easy access to shopping, dining, entertainment, and transportation. A short drive to The Loop Mall and close to Central Florida’s best restaurants and attractions. This versatile property is ideal as a primary residence, second home, or investment opportunity. A must-see first-floor unit—schedule your private tour today!

Listing is courtesy of: ATRIUM REALTY, LLC (833-919-1190)

Listing Agent: Ernani Sena (774-258-0635)

Remarks: Bring your imagination!!!fixer upper in the best part of city of Kissimmee! Vintage home ready for that buyer that loves a bit of history. room. Great possibilities. Income producer $4,000 a month

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

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

Remarks: Experience the epitome of resort-style living in this meticulously maintained 2-bedroom, 2-bathroom villa located within the exclusive gated community of Sterling Park at Stonefield. The interior radiates modern elegance with soaring ceilings, crown molding, and premium porcelain tile flooring throughout a bright, open-concept layout. At the heart of the home, the chef-inspired kitchen shines with crisp white cabinetry, granite countertops, and stainless steel appliances, seamlessly flowing into a sun-drenched dining area. Retreat to the spacious primary suite, complete with custom shutters and a spa-like ensuite featuring a dual vanity and a frameless glass walk-in shower. Beyond the glass sliders, your private screened-in lanai offers peaceful, unobstructed views of the community’s lush greenspace—perfect for quiet Florida mornings. With the HOA handling lawn and exterior maintenance, you’re free to enjoy the resort-style pool, fitness center, and tennis courts, all while being minutes away from world-class shopping at The Loop and major Orlando attractions.

Listing is courtesy of: MILESTONE FAMILY REALTY LLC (689-265-3683)

Listing Agent: Jeff Joachim (689-304-9330)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This 4 bedroom, 2 bathroom home with 1,720 sq ft checks the boxes buyers are asking for, space, layout, location, and the ability to move in without the wait. Located in a small gated community, you will enjoy a peaceful water view and a layout that actually makes sense. The oversized living and dining area gives you flexibility for everyday living or hosting, with crown moulding and tile flooring throughout the main spaces. The bedrooms feature wood floors, and the home is clean, well-maintained, and ready for its next owner. That is where the value is. Additional features buyers love: • 2 car garage with epoxy floors • In-home washer and dryer included • Open, functional floor plan • Natural light throughout • Vacant for easy showings and quick closing Whether you want a primary residence you can personalize over time or a solid investment, this property offers a great combination of condition, location, and opportunity. Seller is motivated and ready to make a deal. Homes with this much space, in a gated community, with a water view, at this price point, do not last. Schedule your showing and see the potential for yourself.

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

Listing Agent: Naomi Embleton (407-709-6020)

Remarks: Welcome to this spacious and inviting home, thoughtfully designed for comfortable family living and making lasting memories. Step inside to a bright, open-concept living and dining area—perfect for both entertaining guests and everyday relaxation. The kitchen is a true centerpiece, featuring brand-new appliances, a convenient breakfast bar, and a cozy eat-in space. It flows seamlessly into the family room, creating an ideal layout for staying connected with family and friends. Brand new HVAC (2026) Roof (July 2025). The generously sized primary suite offers a peaceful retreat, complete with a walk-in closet. Three additional bedrooms provide ample space and flexibility for family, guests, or even a home office. Enjoy added privacy with no rear neighbors, as the home backs up to a tranquil wooded area—perfect for relaxing or unwinding outdoors. Ideally located in the heart of Kissimmee, this home is just minutes from major highways, shopping centers, dining, and everyday conveniences. This home truly has it all and won’t last long—schedule your private showing today!

Listing is courtesy of: CENTURY 21 CARIOTI (407-566-0555)

Listing Agent: Evagisela Rodriguez (407-566-0555)

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: 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: 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)