Homes for Sale Near Osceola High School in Kissimmee - 150 homes

Remarks: Located in the sought-after Tapestry community, this beautiful 3-bedroom, 2.5-bath townhome offers a spacious and inviting layout with numerous upgrades throughout. The open-concept design features a large kitchen with granite countertops, stainless steel appliances, and ample cabinetry, seamlessly connected to the dining and living areas—ideal for entertaining and everyday living. High ceilings enhance the natural light and create an airy feel throughout the home. All bedrooms are located upstairs, including the primary suite, along with two additional bedrooms and a conveniently positioned laundry room. The bedrooms are generously sized and offer plenty of storage space and large windows. All appliances are included. Conveniently situated near major roads, shopping, dining, and everyday conveniences. A great opportunity to own in one of the area’s most desirable communities!

Listing is courtesy of: ORLANDO BROTHERS REAL ESTATE LLC (407-925-2221)

Listing Agent: Iluska Kruse (407-925-2221)

Remarks: BEAUTIFUL AND CENTRALLY LOCATED TOWNHOME!!!! This property offers a spacious and functional layout, ideal for homeowners or investors. Its prime location provides direct access to major roads such as John Young Parkway, Osceola Parkway, and US-192, allowing for quick connectivity to Orlando, employment centers, and world-famous attractions. Just minutes from The Loop, where you’ll find a wide variety of restaurants, shopping, entertainment, and everyday conveniences. Surrounded by supermarkets, dining options, and schools, this property perfectly combines comfort, location, and convenience. The seller is motivated and willing to contribute toward closing costs, making this an excellent opportunity for buyers. A truly exceptional opportunity to live or invest in the heart of Kissimmee!

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

Listing Agent: Lisbeth Hernandez Gil (786-498-9363)

Remarks: Welcome to resort-style living at Tapestry in Kissimmee! This beautiful 3-bedroom, 2 full bathrooms + 1 half bath townhouse offers a modern open floor plan designed for comfort and entertaining. The home features a spacious kitchen with stainless steel appliances, generous living and dining areas, a 2-car garage, and a private second-floor balcony perfect for relaxing. Located inside the highly desirable gated community of Tapestry, residents enjoy access to an incredible clubhouse with luxury amenities including a resort-style pool, fitness center, splash area, playgrounds, walking trails, sports courts, and beautifully maintained common areas. Conveniently located near The Loop shopping center, restaurants, major highways, Orlando attractions, and Disney parks. A perfect opportunity for primary residence, vacation home, or investment property!

Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)

Listing Agent: Alex Leonardo (407-832-2946)

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: Under contract-accepting backup offers. Just Listed! Check out this fantastic pool home with a 3 car garage, perfectly tucked away in a quiet neighborhood yet close to everything Kissimmee has to provide. From the moment you step inside, you’ll love the floor plan with a direct view to the gorgeous pool! Ceramic tile flooring flows through the main living areas ideal for both everyday living and entertaining, while plush carpet in the bedrooms adds comfort underfoot. The floor plan includes an eat-in kitchen, family room, formal dining room, formal living room, and outdoor living space. The primary suite has 2 closets, sliding doors to the pool area, and its own ensuite bathroom with double vanities and step-in shower. Step through sliding glass doors to the covered lanai, the perfect place to unwind with a good book, host friends, or watch your family play in the fenced backyard that offers space to play or simply relax in the Florida sunshine. Step into your own private paradise with a resort-style backyard designed for both relaxation and entertaining. The stunning resort style pool area is surrounded by lush tropical landscaping that creates a peaceful, vacation-like setting right at home. Premium turf adds beauty and functionality with a clean, manicured look year-round while minimizing maintenance and mud. Whether you’re hosting friends, enjoying family time, or unwinding after a long day, this outdoor oasis offers the perfect blend of luxury, comfort, and low-maintenance living. Recent updates and upgrades include a New roof, New AC, New fresh paint, New bathroom sinks and plumbing fixtures, Kitchen cabinet refresh, Premium turf in the backyard, New pool pump, and much more! You’ll appreciate the convenience of a fantastic central location - close to shopping, dining, schools, and medical facilities! Don’t miss the chance to make this Kissimmee home your own. Schedule your private showing today and start living the lifestyle you’ve been waiting for!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Christina Moore (863-430-8517)

Remarks: This beautifully maintained first-floor three-bedroom, two-bathroom condo in Kissimmee offers an exceptional opportunity for homeowners and investors alike. Conveniently located near major shopping centers, restaurants, and entertainment, and just minutes from Walt Disney World Resort, this property combines comfort, convenience, and lifestyle. Situated within a secure gated community, residents enjoy peace of mind along with amenities designed for relaxation and enjoyment. The community features elevator access to all floors and a beautifully designed resort-style pool overlooking the lake, creating the perfect setting to unwind. Located on the first floor for added convenience and easy access, this condo is ideal for families, professionals, or investors seeking strong rental potential in one of Central Florida’s most desirable areas.

Listing is courtesy of: ALTIS REALTY (407-401-7447)

Listing Agent: Reynaldo Izaguirre, Pa (407-683-0998)

Remarks: Discover this beautifully renovated home, perfect for living or investing, 2 Bedrooms | 1 Bath, Spacious Living & Dining Room. Brand-new kitchen with granite countertops, Fresh interior & exterior paint. Charming front & Back porch to enjoy your mornings. Elegant pavers! New metal roof! NO HOA! Prime opportunity in Kissimmee? Ideal for first-time buyers or investors. Schedule your private showing today! Wheel Chair Ramp, Dead-End. Community Allow 1 RV at the property!

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

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

Remarks: Under contract-accepting backup offers. A rare opportunity part of historic Downtown Kissimmee with NO HOA. This charming well kept 2 bedroom 2 bath property is on a fully fenced lot with a huge extended Driveway that easily fits multiple vehicles meaning bring your boat, trailer, or work trucks with no restrictions. NO HOA! Great starter home that checks all the boxes. Roof was replaced in 2019 and air conditioning unit was replaced in 2025. Location is everything, and this one is unbeatable. Just a few blocks from Downtown Kissimmee, you’re minutes from Lake Toho's scenic waterfront, Kissimmee Lakefront Park, restaurants, Broadway Pizza, boutiques, the Kissimmee Valley Farmers Market, year-round community events, seasonal festivities, bus depot and Sun Rail access for easy commuting. Easy access to Disney, major roads and highways, the Turnpike and the hospital is just a few block away. Opportunities like this in Downtown Kissimmee don’t come around often so HURRY before it's gone!

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

Listing Agent: Lucy Rivera (407-922-1953)

Remarks: THIS HOME IS A MUST SEE!!! Welcome to this stunning 4-bedroom, 3.5-bathroom home, ideally located in the sought-after Solara Resort in Kissimmee. Whether you're looking for a full-time residence or a vacation home investment, this property offers the perfect blend of relaxation and convenience. Situated just off US-192, with quick access to I-4 and US-27, you’re only 8 miles from world-class theme parks and just a short commute to the famous attractions of the Orlando area, including local beaches. Enjoy easy access to premier shopping and dining options along International Drive or at the Prime Outlet Mall. The Solara Resort community offers an unparalleled resort-style living experience with amenities that include an on-site restaurant, coffee bar, beach-style pool, pool bar, fitness center, basketball court, soccer field, volleyball court, gaming stations, sports simulator, yoga lawn, playground, splash pad, water slides, and even a Flowrider sea wave simulator – there's something for everyone! Inside, the home has been beautifully decorated and furnished by professionals with an open floor plan that is perfect for entertaining. The spacious kitchen boasts granite countertops and stainless-steel appliances, making meal prep a true pleasure. The upstairs loft is a media dream, providing ample space for movie nights or relaxation. The dining area seamlessly flows into the outdoor space through sliding doors, leading to your own private pool—ideal for extending your entertainment space. Don’t miss out on this incredible opportunity to own a piece of paradise. Call today and schedule your showing at your convenience!

Listing is courtesy of: LEGACY PLUS REALTY (407-992-2268)

Listing Agent: Solon Potenciano Silva (407-760-5141)

Remarks: INVESTOR OPPORTUNITY! HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: INVESTOR OPPORTUNITY! HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: Under contract-accepting backup offers. INVESTOR OPPORTUNITY! HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: ?? INVESTOR OPPORTUNITY! ?? HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: ?? INVESTOR OPPORTUNITY! ?? HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: Under contract-accepting backup offers. Welcome to the newly renovated 2628 Milton Ave, a beautifully updated block home located in the established community of Kissimmee Highlands! Situated on an oversized lot just shy of ¼ acre with NO HOA, this move-in ready property offers the perfect combination of modern upgrades, functionality, and value. Completely renovated in April 2026, this home has undergone an extensive transformation from top to bottom. Major improvements include a BRAND NEW ROOF WITH ALL NEW PLYWOOD, COMPLETE ELECTRICAL REWIRE, NEW WATER HEATER, NEW FLOORING THROUGHOUT, FULLY REDESIGNED KITCHEN, BRAND NEW APPLIANCE PACKAGE, UPDATED BATHROOMS, RECESSED LIGHTING, NEW FIXTURES, NEW INTERIOR DOORS, TRIM AND BASEBOARDS, FRESH INTERIOR AND EXTERIOR PAINT, AND NEW TEXTURE ON ALL WALLS AND CEILINGS. The HVAC system has also been PROFESSIONALLY CLEANED AND SERVICED, along with the installation of a NEW THERMOSTAT for added comfort and efficiency. Conveniently located near major roadways, shopping, dining, schools, and everyday conveniences, this property offers outstanding accessibility while still providing the benefit of a larger lot size that is increasingly difficult to find. The expansive yard offers endless potential for outdoor entertaining, storage, gardening, or future additions. This area also allows for ADUs (Accessory Dwelling Units), and the oversized lot provides excellent potential for future expansion, guest quarters, rental income opportunities, or multi-generational living. With all the major upgrades already completed, this home is ideal for first-time buyers, downsizers, investors, or buyers seeking additional long-term upside potential. 2628 Milton Ave is the perfect blend of classic construction and modern renovation — ready for its next owner to move right in and enjoy.

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Alex Vazquez (407-270-6841)

Remarks: One or more photo(s) has been virtually staged. Beautiful 3- bedrooms and 2- bathrooms home in the heart of Kissimmee with NO HOA! Conveniently located near Downtown Kissimmee shopping, restaurants, schools major highways,and just minutes from Kissimmee Lakefront Park. This home offers comfort,space,and the freedom of no HOA restrictions. Perdect for first-time buyers or anyone looking for a great location in Central Florida!

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

Listing Agent: Susana Moor (407-744-5801)

Remarks: Investor special opportunity at 2460 Summerfield Way in Kissimmee. This 2-story townhouse offers immediate rental income with a tenant already in place paying $1,500 per month on a year-long lease, making it a turnkey addition to any investment portfolio. The property features 2 bedrooms, 2.5 bathrooms, and a functional layout designed for comfortable everyday living. The main level includes the shared living and dining areas, along with a conveniently located kitchen and half bath for guests. Upstairs, both bedrooms offer access to full bathrooms, creating a practical setup for residents, roommates, guests, or even a home office configuration. The patio provides additional usable outdoor space for seating, dining, or relaxing while remaining low maintenance. Investors will appreciate the major system updates already completed, including a new roof in 2024, a water heater that is only 1 year old, and an HVAC system replaced in 2022. These improvements help minimize near-term maintenance concerns and add long-term value to the property. Located in Kissimmee, the home offers convenient access to shopping, dining, schools, parks, major roads, and Central Florida attractions. The neighborhood provides a residential setting with everyday essentials nearby, making it an appealing option for both tenants and long-term investors seeking convenience and steady rental potential.

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

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

Remarks: Beautiful and well-maintained single-family home located in a gated community in the heart of Kissimmee, Florida. This stunning property offers 3 bedrooms, a bonus room, 2 bathrooms, and a spacious 2-car garage. The home features 2 A/C units that are approximately one 1/2 year old, smart thermostats for energy efficiency and comfort, a central vacuum system, and a modern wall-mounted water heater. The interior doors and front door have also been freshly painted, giving the home a clean and updated appearance. Inside, you will find an open floor plan with vaulted ceilings and ceramic tile flooring throughout the home. The spacious family room and dining room combination create the perfect setting for entertaining and everyday living. The open kitchen includes an island with electrical outlets, a range hood, a bar, a wine rack, and stainless steel appliances. The bonus room can easily be used as a nursery, office, guest room, or additional bedroom. The primary bathroom features a double vanity, a walk-in closet, and a separate shower. Skylights provide beautiful natural lighting throughout the bathrooms and living areas. Step outside to your screened patio and enjoy breathtaking pond views with a relaxing fountain backdrop, peacecul outdoor setting perfect for morning coffee or evening relaxation. The backyard is surrounded by beautiful palm views, bringing the best of Florida living right to your backyard. Community amenities include a resort-style pool, basketball courts, a tennis court, a playground, and beautifully maintained common areas. Conveniently located just 15-20 minutes from Disney World, Disney Springs, SeaWorld, Universal Studios, International Drive, Downtown Orlando, and Orlando International Airport. Easy access to the Florida Turnpike, plus proximity to schools, shopping centers, restaurants, and hospitals. Schedule your private showing today and experience everything this beautiful home.

Listing is courtesy of: SIGNATURE BROKERS REALTY LLC (407-595-6820)

Listing Agent: Mickie Rodriguez (407-949-4902)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautifully maintained two-story pool home located in one of Kissimmee’s most desirable gated communities. From the moment you arrive, this stunning residence impresses with its elegant curb appeal, soaring ceilings, abundant natural light, and thoughtfully designed spaces throughout. This spacious home features 5 bedrooms, 3.5 bathrooms, a versatile loft, plus formal living and dining rooms, offering the perfect balance of comfort, style, and functionality for everyday living and entertaining. The heart of the home is the spacious kitchen, complete with a center island, brand-new stainless-steel appliances, ample cabinetry, and a large walk-in pantry. Overlooking the main living area, the layout creates a warm and inviting atmosphere while still maintaining distinct living spaces for added comfort and privacy. The formal dining room provides the perfect setting for gatherings and special occasions, while the formal living room adds an elegant and flexible space ideal for entertaining or relaxing. The primary suite is conveniently located on the first floor, providing a private retreat with comfort and convenience. Upstairs, you’ll find four generously sized bedrooms, all featuring walk-in closets, along with a spacious loft ideal for a media room, home office, playroom, or additional living area. Step outside to your private screened-in pool area, the perfect space to relax, entertain, and enjoy Florida living year-round. Residents of the highly sought-after Stonefield community enjoy resort-style amenities including a beautiful clubhouse, community pool, fitness center, tennis court, and recreational areas. Ideally located near The Loop shopping center, dining, major highways, theme parks, and all that Central Florida has to offer. This exceptional home offers the perfect combination of space, elegance, comfort, and lifestyle. A true must-see!

Listing is courtesy of: TOP 7 REALTY LLC (407-334-8082)

Listing Agent: Audrey Torres (407-730-1862)

Remarks: Welcome to this spacious 3-bedroom + Office/smaller bedroom and 2-bathroom home offering privacy and tranquility with no rear neighbors and a stunning nature view from the screened-in patio. The interior features tile flooring throughout the main living areas, with cozy carpet in guest bedrooms. The Primary bedroom has luxury vinyl flooring. The kitchen has been tastefully updated, providing both style and functionality. The lanai has been extended and paved making it perfect for entertaining outdoors. Located in a man-gated community, residents enjoy top-notch security and access to resort-style amenities, including a community pool, fitness center, playground, and walking trails. Conveniently situated near major highways, shopping, and dining, this home combines comfort, convenience, and a peaceful setting. Owner Motivated

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Lorena Correa (407-415-9170)