Homes for Sale Near Osceola High School in Kissimmee - 109 homes

Remarks: EXCELLENT INVESTMENT OPPORTUNITY—Rare opportunity to own a property with dual living spaces. Enjoy a 2-bed, 1-bath main house plus a private, FULLY RENOVATED (Jan 2024) 1-bed, 1-bath suite at the rear—perfect for guests or potential rental income. Great Location—Low annual expenses. NO HOA–NO CDD. Prime location surrounded by restaurants and shops. Just minutes from major highways, and a short drive to. The main house is tenant-occupied under a month-to-month lease. Buyer is responsible for conducting their own due diligence regarding square footage, lot size, room dimensions, and taxes.—Private financing available.

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

Listing Agent: Rebecca Francia (407-288-7603)

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: Welcome to this well-maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and location. Inside, you’ll find multiple living spaces including a formal living room, dining room, and a spacious family room—ideal for both everyday living and entertaining. The kitchen flows seamlessly into the main living areas, creating a warm and inviting atmosphere. The primary suite features a large bathroom complete with a soaking tub and separate walk-in shower, providing a relaxing retreat. Step outside to your private backyard oasis with a screened-in pool and fully fenced PVC yard—perfect for enjoying Florida living year-round. Additional updates include a newer AC system installed in 2023 for added peace of mind. Located in the desirable Cranes Cove community, residents enjoy low HOA fees and access to a community pool. Just minutes from The Loop shopping center, you’ll have convenient access to restaurants, movie theaters, shopping, and more. Plus, you’re a short drive to Disney and all that Central Florida has to offer. Whether you’re looking for a primary residence, investment property, or vacation home, this one truly checks all the boxes.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Dominick Florio (321-377-4045)

Remarks: One or more photo(s) has been virtually staged. Welcome to 923 S. Park Ct., Kissimmee, FL 34741 - a charming single family home situated in an established Osceola County neighborhood. This residence features three bedrooms and one full bathroom, offering a comfortable and functional layout with plenty of potential. The home features tile flooring throughout, making for easy maintenance. Step outside to enjoy a fully fenced front and back yard, providing space to relax. The backyard also includes a shed for additional storage and a driveway offers convenient off-street parking. The roof was completed in 2021. Ideally positioned near downtown Kissimmee, this home provides convenient access to a variety of shopping, dining and local amenities. This is a wonderful opportunity to own a single family home in a prime Kissimmee location. Schedule your showing today!

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: One or more photo(s) has been virtually staged. This lovely, spacious condo in Kissimmee's gated Flora Ridge community offers the perfect combination of comfort and convenience. Located on the second floor with an elevator, this 1,779-square-foot apartment has an open layout that flows seamlessly between the kitchen and living room. There is also freshly painted interior throughout the unit, a recently replaced refrigerator, air conditioning and water heater, a master bedroom with double sinks and walk in closet, and a screened porch. Homeowners get two dedicated parking spots, one with a covered carport and one without. There is a community pool with amazing water view, and walking trail. It is situated just minutes from The Loop, a premier shopping and dining destination, making it easy to access the Florida Turnpike, Osceola Parkway, and world-famous theme parks. Along with the regular assigned schools, there is Renaissance Charter School with an A rating available from Kindergaden to 12th grade.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Brigitte Elzarki (321-231-4999)

Remarks: CHARMING DOWNTOWN KISSIMMEE HOME WITH MODERN UPDATES,FRESH INTERIOR PAINT & CLASSIC CURB APPEAL WELCOME TO THIS BEAUTIFULLY MAINTAINED 3-BEDROOM, 2-BATHROOM HOME IDEALLY LOCATED IN THE HEART OF DOWNTOWN KISSIMMEE, JUST MINUTES FROM SHOPPING, RESTAURANTS, AND PUBLIC TRANSPORTATION. INSIDE, YOU’LL FIND A SPACIOUS GREAT ROOM, WELL APPOINTED KITCHEN AND BATHROOMS. OFFERING MODERN COMFORT WITH TIMELESS STYLE. THE LARGE KITCHEN AND DINETTE AREA ARE PERFECT FOR EVERYDAY LIVING AND ENTERTAINING, COMPLETE WITH A LARGE PANTRY AND A CONVENIENT INSIDE LAUNDRY ROOM. STEP OUTSIDE AND ENJOY THE HOME’S CLASSIC CHARM WITH A COVERED FRONT PORCH WITH RAILING OVERLOOKS A LOVELY PICKET FENCE, CREATING A WARM AND WELCOMING FIRST IMPRESSION. ADDITIONAL FEATURES INCLUDE A 2-CAR CARPORT AND A 10X12 STORAGE SHED WITH ELECTRIC, IDEAL FOR TOOLS, HOBBIES, OR EXTRA STORAGE. MAJOR UPDATES INCLUDE A BRAND-NEW ROOF (2025), GIVING PEACE OF MIND TO THE NEXT OWNER. THIS MOVE-IN-READY HOME BLENDS LOCATION, SPACE, AND CHARACTER. WHAT AN EXCELLENT OPPORTUNITY TO OWN A WELL MAINTAINED PROPERTY RIGHT IN DOWNTOWN KISSIMMEE.

Listing is courtesy of: GOODWIN REALTY & ASSOCIATES, INC (407-846-2787)

Listing Agent: Linda Goodwin-Nichols (407-908-0320)

Remarks: 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)

Remarks: $80,000 price improvement — now offered at $530,000 in the gated Tapestry community, just 15 minutes from Disney. Proudly owned by only one owner, this fully modernized 4-bedroom + office + loft, with 3.5-bath, offers nearly 2,400 sq ft of functional living space. Including a downstairs bonus room and a spacious upstairs loft. The private backyard is a standout feature, designed for comfort and entertainment with artificial turf, paved gathering areas, a jacuzzi, and full fencing for added privacy and low maintenance. Additional highlights include a 2-car garage and fully installed security system. Conveniently located just 0.7 miles from Kissimmee Middle School and minutes from major shopping, dining, and highways. Residents of Tapestry enjoy true resort-style living with a clubhouse, resort pool, water play area, playgrounds, dog park, scenic conservation areas, and a fully equipped fitness center. With this new price adjustment, opportunities like this don’t last — schedule your private tour today.

Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)

Listing Agent: Gabriella Massaro (689-280-9558)

Remarks: Charming 2-bedroom, 1.5-bath condo perfect for a first-time homebuyer, starter home, or investment opportunity. This inviting home features an updated kitchen with granite countertops, bright white cabinetry, and mix stainless steel appliances, offering a clean and functional space that opens to the main living area. The first floor features tile flooring throughout the living and dining areas, while both bedrooms are privately located upstairs with carpet flooring for added comfort. Enjoy relaxing outdoors on the spacious screened-in porch with a private rear view. Additional highlights include a 1-car garage and a location just steps from the community pool and clubhouse, making it easy to enjoy the neighborhood amenities. Great investment potential with rental rates in the area available. Conveniently located near shopping, dining, and major roadways.

Listing is courtesy of: HELLO SUNSHINE REALTY LLC (407-719-8932)

Listing Agent: Marissa Mcclung (407-719-8932)

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: Under contract-accepting backup offers. This Retreat is a Masterpiece of Craftsman Artistry This seller has thought of everything before you can even imagine it! This estate boasts over 3,300 square feet with 3 bedrooms, 3.5 bathrooms and an attached 1 bedroom, 1 bath apartment. It will give you the experience of a life of uncompromised luxury and small-town charm in this spectacular Craftsman estate. Re-imagined with attention to detail and situated on a sprawling half-acre double corner lot, this home isn’t just a residence—it is a sanctuary. Located in the coveted Orange Gardens neighborhood, no HOA, you are mere steps from the vibrant energy of downtown boutiques, artisan dining, and the convenience of commuter and Amtrak rail services. You can also enjoy the near by parks with a short walking or biking distance away. From the curb, the home radiates quality. It has a gable hip roof and concrete block hardi board exterior with seamless gutters. The true magic, however, begins with entering a foyer that takes your breath away. Looking down, the limestone and travertine floor showcases an original clematis design. Above, the octagonal cathedral ceiling features a hand blown glass fixture surrounded by translucent panels, filtering in natural light. Ultimate Retreat & Personal Fortress The primary suite is a masterclass in tranquility. Drift off under a romantic barrel-vaulted trey ceiling with soft cove lighting, or enjoy your morning coffee on the private screened patio. For a peace of mind, the suite features a discreetly integrated storm sanctuary—a custom walk-in closet reinforced with a roll-down door to keep your loved ones safe during any weather. The ensuite is a spa-like escape, boasting a two-person Jacuzzi tub and a floor-to-ceiling double-head shower surrounded by cultured marble, turning every morning into a five-star experience. Built for Connection & Creating Memories The gourmet kitchen and great room are a host’s dream. Imagine holiday gatherings centered around the massive granite island, with cocktails served from the professional-grade wet bar. Diamond Reflections cabinetry with appliance garages to keep your workspace pristine. The great room’s coffered ceilings and filtered sunlight create an atmosphere of warmth and sophistication. Alfresco Potential: Step out onto the patio—engineered with heavy-duty footings—ready to be transformed into the ultimate outdoor kitchen or covered lounge. For versatility, a secondary suite features a Murphy bed system, transforming a high-end home gym or executive office into a luxury guest suite. A third bedroom with an ensuite & patio access is also situated just down the main hall from the primary, giving you more space and privacy for all of your guests. If multi-generational living or a lucrative income stream is of interest, the attached private apartment is fully-equipped, offering its own kitchen, laundry, and separate entrance without sacrificing the main home’s privacy. Behind the beauty lies unparalleled engineering and self sufficiency. Throughout you will see several Velux sun tunnels that provide natural sunlight. A new roof as of 2023 and a whole house water filter and water softener. Across the home is four HVAC zones makes this home as "smart" as it is stunning. ADT hardwired security & privacy hedges ensure your private patio remains private. This is a thoughtfully crafted lifestyle for the buyer who demands excellence in every inch of their surroundings.

Listing is courtesy of: RIVER HILLS PROPERTIES, LLC B (315-896-1009)

Listing Agent: Heather Claridge (941-404-8193)

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: Under contract-accepting backup offers. 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: Stunning 2-bedroom, 2-bath condominium with 1-car garage! This beautifully maintained home offers a bright and airy open-concept design, perfect for both everyday living and entertaining, ideally located next to the community clubhouse, offering easy access to amenities and enhancing your lifestyle. Enjoy two spacious master suites, each featuring its own walk-in closet, providing comfort, privacy, and flexibility. Elegant laminate flooring flows seamlessly throughout the entire home, creating a modern and cohesive feel. The kitchen is equipped with a gas stove, perfect for those who love to cook, and features recent upgrades including a brand-new refrigerator (2025), new microwave (2025), and new garbage disposal (2025). The A/C unit was replaced in 2019. Additional highlights include a convenient inside laundry room and a well-designed layout that maximizes both space and functionality. This move-in ready condo offers the perfect combination of style, comfort, and low-maintenance living—a true must-see!

Listing is courtesy of: VENTURE HOME REALTY (407-587-0076)

Listing Agent: Reyna Quezada (407-780-0426)

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: Best value in the city of Kissimmee! CASH ONLY. This upgraded 3-bedroom, 1-bath home is one of the most affordable properties in the entire zip code—an incredible opportunity you don’t want to miss. Move-in ready with recent improvements, this property offers the added benefit of NO HOA, providing freedom and flexibility for homeowners and investors alike. Ideally located in Kissimmee, just approximately 20 minutes from Orlando International Airport and 25 minutes from Walt Disney World. Enjoy easy access to major roadways, including US-192, John Young Parkway, Osceola Parkway, and Florida’s Turnpike, making commuting a breeze. Conveniently close to shopping, dining, and schools. Perfect for first-time buyers or investors looking for strong value in a high-demand area!

Listing is courtesy of: FLORIDA LAKES REALTY (407-593-9087)

Listing Agent: Tatiana Diaz (407-593-9087)

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. The home may be sold furnished.

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

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

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2-bathroom pool home perfectly situated on a scenic pond in a gated community. This immaculately cared-for residence offers the ideal blend of comfort, privacy, and Florida lifestyle living. Relax or entertain in your private pool overlooking tranquil water views, creating the perfect backyard retreat. The home features a spacious and functional layout, ideal for both everyday living and hosting family and friends. Pride of ownership is evident throughout, making this home truly move-in ready. Conveniently located in a central location close to shopping, dining, and major roadways, with easy access to Orlando’s world-famous theme parks and Orlando International Airport, making travel and entertainment just minutes away. This exceptional home offers the perfect combination of location, lifestyle, and meticulous maintenance.

Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P (407-730-8737)

Listing Agent: Edwin Gonzalez (321-402-2284)

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: 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)