Homes for Sale Near Osceola High School in Kissimmee - 145 homes

Remarks: Experience resort-style living in the gated community of Tapestry. This stunning 3BR/2.5BA townhouse features a modern chef’s kitchen with state-of-the-art appliances, granite countertops throughout, and ample storage. Enjoy premium amenities including a luxury clubhouse, fitness center, and sparkling pool. Perfectly located and move-in ready—schedule your tour today!

Listing is courtesy of: REALTY HUB (407-900-1001)

Listing Agent: Ramesh Vanapalli (954-892-5648)

Remarks: One or more photo(s) has been virtually staged. Price reduction!! 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: Back to the Market. Don't miss this great opportunity. 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. HOA includes lawn maintenance. 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: Location, location! The seller is motivated to assist with some closing costs, which can be used to lower the interest rate or pay for closing expenses. Don't miss this opportunity to live in Tapestry community First time buyers ,investors Spectacular 4/3 with a beautiful landscaping exclusively designed for the property, it is located in one of the best areas of Kissimmee, with good access to I4, Osceola pkwy, 417, 528 and turnpike, access to everything you need for your daily living. It is a 24 hour guarded gate community with excellent amenities In addition, the house has a covered and completely fenced patio to generate privacy in your patio and your parties. Don't miss out on this opportunity.

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

Listing Agent: Juan Oberto (407-810-3694)

Remarks: 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 Hot Water 2026, 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: Welcome to 2516 Nouveau Way — a beautifully maintained 4-bedroom, 3-bathroom home located in a gated community just minutes from The Loop, shopping, dining, entertainment, major highways and Disney Parks. This spacious home features an open-concept layout filled with natural light and a desirable private-entry guest bedroom with full bathroom access, perfect for extended family, guests, or added privacy and flexibility. Designed for both comfortable everyday living and entertaining, this home offers the ideal blend of space, convenience, and location in the heart of Central Florida.

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

Listing Agent: Ariel Vargas (407-558-5161)

Remarks: This two-story, 3 bedroom, 2.5 bathroom townhouse in the gated community of Fiesta Key. The first floor features an open floor plan with tile flooring throughout, connecting the living room and dining area to the kitchen. The kitchen includes granite countertops, an island with seating space, wood cabinets, and stainless steel appliances. A screened porch with a storage room is locate off the back. All bedrooms and the laundry area are located on the second floor. The primary bedroom includes a walk-in closet and a private bathroom with a double sink granite vanity and a shower. The other two bedrooms share a second full bathroom, which also features a double -sink granite vanity, a tub, and a linen closet. Fiesta Key community amenities includes a fitness center, two pools, and a tennis court. The property is locate minutes away from Disney parks, Universal Studios, shopping centers, dining, schools, making a great option for a primary residence, vacation home, or investment property.

Listing is courtesy of: TOPSKY REALTY INC (407-476-6189)

Listing Agent: Marggy Nieves (407-334-4149)

Remarks: ** Back on the market with the Backyard renovation buyers asked for, you won’t want to miss this. Completely transformed back yard oasis, this entire oversized .44 acre lots trees have been completely removed, grinded down and complimented with fresh Sod. We’ve maintained a Privacy border and a Brand New Double Gate Fence, a Brand New Deck/Pergola for entertaining along with a complete pool resurface, 2026 Pool Screen, 2025 roof, 2026 garage door, 2024 AC all with the beautifully remodeled interior, its truly a dream home! Tucked away in the highly sought-after Cross roads of Kings Highway and Neptune, The CDD free and a low HOA community of Harbour Oaks. This fully renovated 4-bedroom, 2-bath residence redefines everyday living with its blend of sophistication and serenity. Step inside to discover 2,369 sq. ft. of open-concept design where every finish has been thoughtfully curated. Featuring a full sized Laundry/Utility room, Wide-plank luxury vinyl floors, a Statement fireplace is the heart of the home, many closets through out. The chef-inspired kitchen featuring 36” soft-close solid wood cabinetry, stylish quartz countertops, and top-of-the-line Energy Star stainless steel appliances. Whether preparing a quiet breakfast or entertaining friends, this space is both functional and breathtaking. Retreat to the spa-inspired marble floor bathrooms, your serene fully screened in pool/patio or to your oversized two car garage that includes screened in sliders for your comfort. LOCATION LOCATION LOCATION, you can’t beat it as is considering its proximity to downtown Kissimmee, 30 mins from downtown Orlando, direct access to 1-4 & turnpike, state road 192, shopping, restaurants, lakes, parks and more and its soon to come developments (including Osceola community park, Osceola Metro Lagoon , Ovation Development and a lot more) within a couple miles this home makes it truly a forever home

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Rene Droz, Iii (407-484-8786)

Remarks: recently exterior painted. Beautiful updated townhouse at Sterling at Stonefield. This lovely 3 bedroom 2 bathroom with screened in patio and a 2 car garage townhome is a corner unit. It has been tastefully upgraded to please the future tenants. The townhome features ceramic tile throughout, new kitchen cabinets with stainless steel appliances and quartz countertop. The bathroom vanities have been upgraded with bronze faucets sand quartz countertops. The master has a spacious walk in closet and upgraded bathroom with a standup shower. No yard to mow since the HOA takes care of the trimming. The community is gated and has a fantastic clubhouse with pool and tennis. Come live in style close to the Loop!

Listing is courtesy of: SUNSHINE PREMIUM PROPERTIES (407-414-7581)

Listing Agent: Monica Mendivil (407-414-7581)

Remarks: Welcome to this fully furnished 4-bedroom, 3-bathroom townhome located in the highly desirable 24-hour guard-gated community of Venetian Bay Villages. Whether you're looking for a primary residence, a vacation home, or an investment opportunity, this property offers incredible potential in one of Kissimmee's most convenient locations. The home is being sold fully furnished, providing a great starting point for personal use or future rental income. The functional floor plan offers spacious living areas, a well-equipped kitchen, and comfortable accommodations for family and guests. Venetian Bay Villages features outstanding resort-style amenities, including multiple swimming pools, a clubhouse, fitness center, tennis, basketball and volleyball courts, playgrounds, picnic areas, scenic walking paths, and beautifully maintained common areas. Ideally located just minutes from Walt Disney World, Universal Orlando, SeaWorld, The Loop shopping and dining, Orlando International Airport, major highways, and countless Central Florida attractions. Seller is motivated and welcomes offers. Don't miss this excellent opportunity to own a property with tremendous potential in one of Kissimmee's most sought-after gated communities

Listing is courtesy of: BAHIA INTERNATIONAL REALTY (407-608-5308)

Listing Agent: Alexandra Mateu (321-332-8039)

Remarks: Welcome to this stunning 5-bedroom, 5-bathroom home, where comfort, style, and adventure come together in one exceptional property. Designed with both relaxation and entertaining in mind, this spacious home features an open-concept kitchen that flows seamlessly into the inviting family room and out to a covered patio. Perfect for hosting gatherings or enjoying Florida’s beautiful weather. Upstairs, you’ll find two luxurious owner’s suites along with a cozy loft area, offering ample space for rest and privacy. Every detail of this home is crafted to create unforgettable experiences for family and guests alike. Located in the highly sought-after Storey Lake Resort, residents and guests enjoy access to resort-style amenities including a sparkling pool, golf, fitness center, and clubhouse. Just 12 minutes from Walt Disney World Resort, this property is perfectly positioned in a prime short-term rental community, making it an outstanding investment opportunity or dream vacation home.

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

Listing Agent: Nayi Torres (407-720-9585)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2-bath pool home offering space, comfort, and an unbeatable location in the heart of Kissimmee. This property is a rare find featuring a 4-bedroom layout with a heated pool and spa on an oversized lot, combined with exceptional curb appeal thanks to its beautifully refreshed landscaping and freshly painted exterior (2024). The large, spacious driveway provides ample room for multiple vehicles. Step inside to an open and airy floor plan with soaring cathedral ceilings that enhance the sense of space and natural light throughout. The centrally located kitchen is ideal for both everyday living and entertaining, featuring ample counter space, a breakfast bar, and a dining nook perfectly positioned by the sliding glass doors offering beautiful views of the pool and backyard. The primary suite is a true retreat, offering dual walk-in closets, a linen closet, and a spacious bathroom with dual sinks and a relaxing jacuzzi tub with jets. Enjoy Florida living at its best in your private backyard oasis situated on an oversized, fully fenced backyard with a mango and an orange tree. The large screened-in patio and heated pool with spa create the perfect setting for entertaining or unwinding year-round. Additional highlights include NO HOA, a roof replaced in 2022, a newer pool pump, a newer pool heat pump, and a well-maintained interior ready for its next owner. Ideally located just minutes from major highways, shopping, dining, and everyday conveniences. Only 5 minutes to Historic Downtown Kissimmee and within 30 minutes to Orlando International Airport and Central Florida’s world-famous attractions. This home offers the perfect combination of space, location, and lifestyle. Don’t miss the opportunity to make it yours! Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Dania Khreiche (407-456-1553)

Remarks: Welcome to this stunning corner-unit townhome in the desirable, gated community of Cypress Ridge! Built in 2020, this beautiful property features 3 bedrooms, 2.5 bathrooms, and 1,771 sq. ft. of modern, open-concept living space. Being a premium corner lot, the home is flooded with natural light. The sleek kitchen boasts a large granite island and stainless steel appliances, flowing seamlessly into the bright living area. Step outside through the sliding doors to enjoy a serene pond view right from your backyard. Upstairs, the spacious primary suite offers a private retreat with dual vanities and a premium glass shower. Conveniently located in Kissimmee, you'll enjoy quick access to the FL Turnpike and Osceola Pkwy, keeping you minutes away from shopping, dining, and world-class attractions. Schedule your private showing today!

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Clarisse Sousa (407-873-0458)

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: Fantastic Opportunity in Kissimmee! Welcome to this well-maintained 2-bedroom, 2-bathroom condo offering 933 sq.ft. of functional living space in the desirable gated community of Bella Vista Condominiums. This unit features an efficient layout with comfortable living areas and ample natural light. Residents enjoy access to excellent community amenities, including a swimming pool, fitness center, and recreational areas. Conveniently located near shopping, dining, schools, and major roadways, this property provides easy access to everything Kissimmee has to offer. SCHEDULE YOUR TOUR TODAY!

Listing is courtesy of: PM ELITE REALTY LLC (407-749-3075)

Listing Agent: Douglas Casique (689-251-0612)

Remarks: HUGE PRICE REDUCTION! Welcome to this inviting and well-maintained home located in the heart of Kissimmee. Offering a functional layout with spacious living areas, this property blends comfort, convenience, and everyday practicality. Natural light flows through the home, creating a warm and welcoming atmosphere perfect for both relaxing and entertaining. The generous backyard provides endless possibilities — ideal for gatherings, gardening, or creating your own outdoor retreat. With no HOA, you’ll enjoy flexibility and freedom rarely found in today’s market. Centrally located near shopping, dining, schools, and major highways, this home offers easy access to everything Kissimmee has to offer while still providing a sense of privacy and calm. Whether you’re a first-time buyer, growing household, or investor, this property represents a solid opportunity and a place ready to create new memories. Schedule your private showing today — homes like this don’t last.

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

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

Remarks: Welcome to 2518 Empress Drive, a fully upgraded, luxury-inspired residence located within the highly desirable gated community of Tapestry in Kissimmee. Built in 2020 and extensively enhanced with high-end finishes and custom outdoor living upgrades, this exceptional 4-bedroom, 2.5-bath home delivers the lifestyle, design, and presentation typically associated with significantly higher-priced properties. Positioned on a premium corner lot, the home immediately impresses with its modern elevation, expansive paver driveway, and oversized 3-car garage. Inside, the open-concept layout showcases elevated contemporary finishes, oversized tile flooring, upgraded lighting, designer accent walls, and expansive living spaces thoughtfully designed for both everyday comfort and upscale entertaining. The true showpiece of the property is the spectacular resort-style backyard, representing approximately $200,000 in custom improvements and curated outdoor enhancements. Designed to rival luxury vacation retreats, the outdoor living experience features a heated saltwater pool with modern architectural lines, premium hardscaping, artificial turf accents, custom lounge areas, covered lanai, pergola, summer kitchen, wood-paneled ceiling detail, integrated entertainment space, and multiple gathering areas designed for seamless indoor-outdoor living year-round. The gourmet kitchen overlooks the main living and outdoor entertaining areas, creating an ideal setting for hosting guests while maintaining functionality and flow. Upstairs, the spacious primary suite offers a private retreat complete with a beautifully upgraded bathroom and oversized custom walk-in closet. Additional bedrooms provide flexibility for family, guests, office space, or lifestyle needs. Every detail of this home has been thoughtfully designed to create a polished, move-in-ready experience that blends modern elegance with resort-style comfort. Residents of Tapestry enjoy access to resort-inspired community amenities including a clubhouse, fitness center, community pool, parks, and recreational areas, all conveniently located near premier shopping, dining, major highways, and Central Florida attractions. This is a rare opportunity to own a highly upgraded, entertainer-focused home offering luxury presentation, exceptional outdoor living, and turnkey sophistication without the million-dollar price tag. Schedule your private showing today via Showingtime.

Listing is courtesy of: CENTURY 21 BE3 (727-596-1811)

Listing Agent: Tom Vitale (407-922-9934)

Remarks: Virtually Staged. Welcome to 3463 Forest Ridge Ln, located in the quiet gated community of Crestwood. This spacious 4-bedroom, 3.5-bath home with a 3-car garage offers over 3,800 square feet of thoughtfully designed living space, combining comfort, privacy, and an unbeatable Central Florida location close to shopping, dining, schools, and world-famous attractions. Designed for comfortable everyday living and entertaining, the home features expansive living spaces, a large kitchen with rich wood cabinetry, center island, pantry, breakfast nook, and a light-filled family room. The screened pool area provides the perfect private retreat for enjoying the Florida lifestyle year-round. The functional floor plan includes a designated office/den on the first floor, a convenient downstairs guest bedroom with its own en suite bath, generous living and dining areas, and a spacious primary suite featuring dual walk-in closets, double vanities, and a garden tub. The home is also ideally positioned near the community playground and pool area, offering convenient access to neighborhood amenities. major improvements provide peace of mind, including a new roof installed in 2021, two HVAC systems installed less than three years ago, a fairly new water heater and pool pump. Conveniently located near The Loop, Walt Disney World Resort, SeaWorld Orlando, Universal Orlando Resort, and Orlando International Airport, this home combines convenience, comfort, and value in one exceptional opportunity.

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

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

Remarks: Welcome home to this beautifully designed, low maintenance townhouse that perfectly balances style and convenience. 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. Do not miss the opportunity, SCHEDULE YOUR VISIT TODAY!!!

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

Listing Agent: Alexandra Cana (407-364-3578)

Remarks: Under contract-accepting backup offers. Welcome to the beautifully decorated Gardenia Floor plan, a designed 3-bedroom, 2-bath single-family home offering 1,706 square feet of thoughtful living space in the highly sought-after, guard-gated Tapestry community in Kissimmee. This isn’t just a home it’s a lifestyle. Step inside to an open, airy layout perfect for modern living. From cozy family nights to weekend entertaining, every square foot is optimized for comfort and flow. With three spacious bedrooms and sleek, contemporary finishes, the Gardenia model is the ideal blend of function and flair. Live like you're on vacation every day with access to a Zero-entry resort-style pool & cabana lounges, Splash pad & play spaces, State-of-the-art fitness center with yoga & movement studio, a Grand ballroom & catering kitchen for hosting unforgettable events, an Open-air veranda for sunset relaxation. Lots of Sports fields, BBQ pavilions, dog park, and walking and biking trails. And it’s all nestled in a 24-hour guard-gated community, minutes from Orlando's top attractions, major highways, the airport, shopping, dining, and great schools. Whether you’re looking for your primary residence, second home, or investment opportunity, this Gardenia beauty is your gateway to elevated living in Central Florida. Homes like this don’t just go on the market they go viral. Schedule your private tour before it’s gone!

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Gladys Bezerra (407-701-4034)