Homes for Sale Near Osceola High School in Kissimmee - 151 homes

Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Located on a quiet street in the heart of Kissimmee, 1903 Brown Street offers a versatile layout and inviting outdoor spaces designed for modern Florida living. This 4-bedroom, 2-bath home features 1,892 heated square feet and an open-concept floor plan that allows the main living areas to flow naturally—ideal for both everyday living and entertaining. In addition to the primary living space, the home includes an oversized garage, a dedicated gym area, and a separate man cave or second living room, providing flexibility for fitness, hobbies, or additional entertaining space. These bonus areas make the home especially well-suited for work-from-home lifestyles, multi-generational living, or those seeking extra functional square footage beyond the bedrooms. Step outside to a private, fully fenced backyard featuring a screened-in pool, perfect for year-round enjoyment, along with a storage shed for added convenience. Centrally located just minutes from shopping, dining, schools, and major roadways, this home offers easy access to Orlando attractions, theme parks, and commuter routes.

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

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

Remarks: Great price on this beautifully renovated home, updated just three years ago! A proven, well-maintained rental with excellent income potential, this solid block 3-bedroom, 1-bath home offers side-yard parking behind fencing plus EV (electric vehicle) hookups. Renovated throughout, the home features all 3-year old appliances, ceramic tile flooring, a fully updated kitchen with 42” soft-close cabinets and stunning quartz countertops, recessed lighting, ceiling fans, tankless water heater, updated plumbing and electrical, 5/8” drywall, doors, paint, and updated ductwork. A/C (2017) and maintained. Enjoy outdoor living with a large covered back porch overlooking a refinished in-ground pool (2019), outdoor shower, RV concrete pad with electric, water, and security lighting, and a roof with solar attic vent. Additional upgrades include hurricane-certified double-pane vinyl windows. Ideally located near downtown Kissimmee, close to Osceola Parkway for shopping, schools, parks, major attractions, and easy access to both East and West Coast beaches. Move-in ready and investment-friendly—this one won’t last!

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Brandy Dileonardo (407-460-2107)

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: Welcome to this spacious and versatile 3-bedroom, 2-bathroom pool home located in a desirable gated community. Designed with a thoughtful split floor plan, this home offers privacy and comfort for the whole family. At the front of the home, you’ll find a bright and airy living room and dining room combo—perfect for entertaining or relaxing. The heart of the home features an open kitchen with a cozy breakfast area that flows seamlessly into the family room, creating a warm and inviting space for everyday living. An additional bonus room just off the family room offers endless possibilities—ideal for a home office, playroom, or personal gym. You'll also appreciate the convenience of an inside laundry room. Step outside to your private backyard oasis with a sparkling pool, perfect for enjoying Florida’s sunny days. Located just minutes from Kissimmee Lakefront Park, shopping, sports venues, restaurants, and world-famous theme parks, this home combines comfort, convenience, and fun in one fantastic package. Don't miss your chance to own this beautiful home in a prime Central Florida location! Roof (2018) HVAC (2022)

Listing is courtesy of: KEYSEEKERS REAL ESTATE (727-490-9000)

Listing Agent: Julie Glass (321-436-6881)

Remarks: BEAUTIFUL AND IMPECCABLE GEM. Welcome to your own piece of paradise here in sunny Florida. This 4-bedroom, 2.5-bathroom home is perfect for your family. Offering endless luxuries throughout the home, upon opening the front door, to your right, you will find an office/study with tons of natural light streaming in. Adjacent to the office/study is the formal dining room, where you can set a long table for your entire family. The whole first floor has Italian porcelain tile floors. The beautiful kitchen features spectacular granite countertops, elegant cabinetry, and high-end stainless steel appliances, providing a spacious and comfortable living area to share with friends and family. The entire home has fine Persilux aluminum blinds. With a large backyard already protected almost entirely with fencing for added security, you will have plenty of space to host gatherings with friends or family. All bedrooms are on the second floor, and the staircase and living room floors are made of brown wood, making it very elegant. The master bedroom has two large, comfortable closets. The master bathroom has a double vanity, a shower, and a garden tub. The home also has a cozy porch where you can enjoy coffee while watching the beautiful Florida sunrise or sunset. The home is located in the beautiful and secure Tapestry community, where you'll enjoy a family-friendly atmosphere. Amenities include 24/7 security, swimming pools, playgrounds, cabanas, and a fitness center. It's also very close to the Loop Mall, where you'll find a wide variety of restaurants and shops, and just 20 minutes from Disney. Don't miss out on this beautiful home for your family!

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Marilin Lugo (407-285-6145)

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: 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: Prime Development Opportunity at 1886 Pleasant Hill Road, Kissimmee, FL 34746! The best time to secure an exceptional vacant land located in a rapidly growing area of Kissimmee. This expansive parcel offers endless possibilities for development, whether you're envisioning residential, commercial, or investment projects. Boasting excellent road frontage and high visibility, this property is perfectly positioned for success. It provides 217’ of frontage on a major highway (Pleasant Hill Rd.) with a daily traffic count north of 50k, it is close to shopping centers, Hospitals, schools and recreational areas, this location provides convenient access to the heart of Kissimmee downtown, and the upcoming Neo City. Take advantage of this rare opportunity to secure a versatile piece of real estate in a thriving and dynamic location. Contact us today for more information or to schedule a visit.

Listing is courtesy of: HOLISTIC REALTY FLORIDA, LLC (407-873-6316)

Listing Agent: Aramis Rodriguez (407-873-6316)

Remarks: PERFECT LOCATION NEAR THE LOOP! This beautiful 5 bedroom, 3 1/2 bathroom home in the gated community of Tapestry has all you have been looking for! Home is on a premium fenced lot with no rear neighbors and water view. This property welcomes you into an open space with formal living and dining area; butler pantry connects you to the kitchen and great room waits for you towards the back of the home with plenty of natural light, and beautiful view of the backyard. Paver driveway has a walkway that wraps around the home with gates on both sides for easy access to the yard and extended Lanai patio. Stainless steel appliances, Quartz countertops, tiled backsplash, Built in fireplace/TV unit with cabinet storage, tile flooring throughout first floor and LVP upstairs; no carpet! There is an ensuite bedroom, a Jack and Jill bathroom, large closet spaces and laundry room located upstairs with all the bedrooms has utility sink, and small refrigerator space to save you the late night trips to your fridge downstairs. Community is gated with guard onsite, resort pool, gym, amenity center, fire pit and playgrounds. Do not miss the opportunity to own this home! 24hrs notice appointment is required.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Yari Villarrubia (407-486-2532)

Remarks: Welcome to 2615 Rapollo Drive, a picturesque CORNER LOT home with a serene LAKEVIEW in the sought-after TAPESTRY community of Kissimmee, FL. This elegantly FURNISHED single-family residence boasts 3 cozy bedrooms, 2.5 modern bathrooms, a dedicated office space, and a versatile bonus room, perfect for families and investors alike. Step inside this rarely used gem to discover an immaculate interior that exudes comfort and class, ready for immediate move-in. The main living area seamlessly flows outdoors to a covered lanai where you can host delightful barbecues, or simply unwind on the charming front porch basking in Florida's sunshine and the stunning views of Tapestry's main lake.**SEE GREAT VIRTUAL TOUR ** Nestled on a generous 0.3-acre lot, this property features a sparkling pool, inviting you to cool off on warm days. With two parking spaces, your vehicles are well-accommodated. Tapestry doesn't skimp on amenities – enjoy the security of a guard gate, clubhouse, gym, and multiple lakes. Location is key, and this home is strategically placed minutes from The Loop Shopping Center, premium outlets, and with easy access to Disney World, Sea World, and Orlando International Airport. Don't miss the chance to own this rare, tranquil retreat in the heart of Kissimmee

Listing is courtesy of: REAL ESTATE COMPASS, LLC (407-402-0232)

Listing Agent: Marilia Neri (407-952-7551)

Remarks: Welcome to this well-maintained 2-bedroom, 1-bathroom condo located in the desirable Terra Condos community in Kissimmee, Florida. Whether you're looking for a cozy full-time residence, a vacation home, or a promising investment property, this condo offers comfort, convenience, and a prime location. Situated just minutes from Kissimmee Gateway Airport, and close to an abundance of shops, restaurants, parks, and major highways, this location puts everything you need within easy reach. Plus, you're only a short drive from some of Central Florida’s most popular attractions, including Gatorland, Discovery Cove, SeaWorld Orlando, and the Disney Theme Parks. Inside, you'll find a functional layout with two spacious bedrooms, a full bathroom, and an open living and dining area perfect for relaxing or entertaining. The kitchen offers ample cabinet space, and the large windows provide plenty of natural light. Community Highlight include a Community pool for residents to enjoy and the fees include: pest control, sewer, trash, and water — for added value and peace of mind. Whether you're looking to invest or unwind, this affordable and low-maintenance condo offers a great opportunity in the heart of Kissimmee. Don’t miss out—schedule your showing today!

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

Listing Agent: Vanessa Santiago (407-995-4630)