Homes for Sale Near Osceola High School in Kissimmee - 108 homes

Remarks: Rare Opportunity. Pristine former model home in the Guard-Gated Community of Tapestry. Experience luxury and peace of mind in this meticulously maintained home, designer-upgraded townhouse. As a former model home, this property boasts premium finishes and has been kept in impeccable condition- never used as a rental and ready for its new owners. Open Concept living, the spacious floor plan seamlessly connects the living, dining, and kitchen areas, making it perfect for entertaining. Located in the heart of Kissimmee the Tapestry community offers an active, resort-style lifestyle. Prime location: just minutes away from world class shopping, dining, top rated schools, and the excitement of Disney and Orlando's world-famous theme parks.

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

Listing Agent: Alexandra Cana (407-346-3578)

Remarks: FULLY RENOVATED HOME on an oversized 0.40-acre corner lot in Kissimmee with NO HOA! Major 2025 upgrades include a new roof, new A/C, all new windows, updated electrical and plumbing systems — offering true peace of mind. Features include an open-concept layout, luxury vinyl flooring, fully remodeled bathrooms, blinds, and a modern kitchen with quartz countertops and a large island. The fully fenced yard provides incredible space to build a pool, expand, or park your RV and boat with no restrictions. Prime central location near major highways, shopping, dining, and schools. Move-in ready with space, upgrades, and freedom — a rare find.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Arlenys Oviedo (786-803-4342)

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: A rare 4-bedroom opportunity in Venetian Bay Villages, strategically priced to generate immediate interest. Welcome to Magnolia House, a 4-bedroom, 3-bath townhome offering a unique blend of space, flexibility, and resort-style living in one of Kissimmee’s most sought-after gated communities. This approximately 1,470 SF residence stands out for its highly desirable layout, designed to accommodate today’s most versatile buyers—whether as a primary residence, second home, long-term rental, or vacation-use property. Set within Venetian Bay Villages, residents enjoy 24/7 gated access and a curated resort lifestyle. These amenities include three catch-and-release fishing lakes, a Jacuzzi, four swimming pools, fitness center, clubhouse, playground, and sports courts—creating a living experience that feels both relaxed and elevated. Positioned near major Central Florida attractions, shopping, and dining, Magnolia House delivers both lifestyle appeal and strong market desirability in a location known for consistent demand. This property is being launched with a high-exposure strategy and competitive pricing designed to attract strong buyer activity early. Buyers are encouraged to act quickly.

Listing is courtesy of: NORTH FLORIDA RE PARTNERS (904-800-8525)

Listing Agent: Edison Cardenas (954-237-9332)

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: 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: Location, location, location! Investors and buyer's delight. This ground floor apartment with screen in porch offers 2 bedrooms and 1 bathroom with lovely tiles all around. Gorgeous stone counter tops, washer and dryer, a very sunny and open space for your enjoyment. A great gated community with basketball course, gym, club House and pool. Plenty of parking and easy access to all the supermarkets, stores, restaurants and parks. Call to schedule a private showing today.

Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)

Listing Agent: Britzeida Pichardo (347-549-7568)

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: 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: 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: Welcome to your vacation lifestyle! This stunning 3-bedroom, 2-bathroom, two-story condo is located in the highly desirable Venetian Villages resort community. Perfect for either a primary residence or a lucrative short-term rental investment. Property Highlights Two-Story Layout: Enter into a bright, open-concept living room/dinette combo. Modern Kitchen: Features granite countertops and brand-new appliances, overlooking the main living area for easy entertaining. First-Floor Primary: The primary bedroom is conveniently located on the main floor with an ensuite bathroom (shower-tub combo). Convenient Laundry: Includes a new, full-size stackable washer/dryer set on the first floor. Upstairs Bedrooms: The second floor offers two additional bedrooms and a shared full bathroom, plus a dedicated owners' storage closet in the hall. Community Features Enjoy an amazing array of resort-style amenities including a sparkling pool, tennis courts, basketball courts, and a volleyball court. The community's location and amenities are ideal for buyers seeking a peaceful, vacation-like setting or investors looking for a prime rental property. Don't miss out on this excellent opportunity!

Listing is courtesy of: LUXE HUNTER REAL ESTATE (407-984-4888)

Listing Agent: Millie Alicea (407-929-1646)

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: **PRICE REDUCTION** Owner offering $5000 towards buyer's Closing Cost. Welcome to this spacious and beautifully maintained 5-bedroom, 4-bathroom home located in the desirable Preserve at Tapestry community. Built in 2015, this two-story residence offers over 3,500 sq. ft. of living space designed with comfort, elegance, and functionality in mind. Step into the heart of the home – a gourmet kitchen featuring premium cabinetry, granite countertops, stainless steel appliances, a center island, and a walk-in pantry, ideal for home chefs and entertaining. The open-concept layout flows seamlessly into the dining and living areas, providing an inviting space for family and guests.The luxurious master suite includes a spa-inspired bathroom with dual vanities, a soaking tub, and a separate walk-in shower. Additional bedrooms are generously sized with access to full bathrooms, perfect for a growing family or multigenerational living.Situated on a spacious lot, the property offers a private backyard with room for outdoor living or a future pool. Community amenities include gated access, parks, and walking trails. Roof Replaced in 2024. Unbeatable location just minutes from The Loop Mall, Orlando International Airport, and all major Central Florida attractions, including Walt Disney World and Universal Studios.Don’t miss this opportunity to own a move-in ready home in one of Kissimmee’s most convenient and vibrant neighborhoods!

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

Listing Agent: Ruben Salvatella (407-530-5006)

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)