Homes for Sale Near Osceola High School in Kissimmee - 63 homes

Remarks: Beautiful two-bedroom, two-bathroom apartment, completely remodeled. This unit is on the 3rd floor of The Villas del Sol Condo community.The building and complex have been completely renovated; gated community with resort style amenities, like swimming pools, Playground, fitness center and Tennis courts. The property can be used as long term or short term rental! Located near major highways for easy access to Central Florida attractions.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Carlos Villamil (407-340-0042)

Remarks: fantastic Location in a desirable gated community, close to restaurants, grocery stores, theater, very accessible to the airport and theme parks, schools, work out clubs, walkways everything you need, with a heated screen in pool overlooking a beautiful view of the pond with a fountain for peaceful evenings from your enclosed lanai, move in ready very well-kept house with newer roof, a/c, you will love the location, location.

Listing is courtesy of: THE EXPERTS TEAM REALTY INC (407-674-7994)

Listing Agent: Eve Hefner (407-509-1517)

Remarks: One or more photo(s) has been virtually staged. .Some condos feel basic. This one feels cared for. Located on the THIRD FLOOR with convenient ELEVATOR ACCESS, this 3-BEDROOM, 2-BATH residence in GATED Flora Ridge offers 1,433 square feet, a light and airy OPEN FLOOR PLAN, SOARING CEILINGS, and a SCREENED BALCONY for relaxed outdoor living. The MODERNIZED KITCHEN features QUARTZ COUNTERTOPS, STAINLESS STEEL Whirlpool appliances, a STAINLESS SINK, updated faucet, garbage disposal, and BREAKFAST BAR seating overlooking the living and dining areas. Additional highlights include LAMINATE WOOD FLOORING in the main living spaces, SHERWIN-WILLIAMS paint throughout, NEW WINDOW BLINDS, CEILING FANS throughout, LED lighting in the guest bath, FULL-SIZE Whirlpool WASHER AND DRYER, and HURRICANE-IMPACT DUAL-PANE WINDOWS in the primary and guest bedrooms. SMART HOME features include a WiFi-enabled entry lock, Nest thermostat and camera, wireless alarm with cellular connection, and UPS backup for the cable modem. Offered MOSTLY FURNISHED, this home is MOVE-IN READY for a primary residence, seasonal retreat, or LONG-TERM INVESTMENT. Flora Ridge offers a COMMUNITY POOL, CLUBHOUSE, scenic lake with fountain, walking paths, ON-SITE PROPERTY MANAGEMENT, and NO SHORT-TERM RENTALS — a meaningful advantage for long-term value and pride of ownership. Ample community parking is available, with most spaces COVERED BY CARPORTS, and the association maintains the EXTERIOR, ROOF, AND GROUNDS for true LOCK-AND-LEAVE convenience.

Listing is courtesy of: THE ROSENBLOOM TEAM (407-376-4454)

Listing Agent: Cindy Rosenbloom (407-876-9175)

Remarks: If you thought you couldn't find an incredible 3-bedroom property with an upstairs entertainment area, 2.5 bathrooms, and a private pool, featuring elegant and comfortable spaces, the seller has created a versatile space that can be used as a fourth bedroom or office, added a shower to the half bathroom, and the home boasts spacious bedrooms, a large kitchen, and a three-car garage. Enjoy a modern kitchen, living room, pool, and a pergola with a barbecue area perfect for entertaining family and friends. Don't miss the opportunity to own this property; a true luxury home awaits you, situated on 0.32 acres of land. This community offers convenient access to shopping areas and major roadways. Let's schedule a showing so you can experience this fabulous property. The seller is motivated to negotiate.

Listing is courtesy of: BRIGHT TRUST REALTY LLC (407-914-0227)

Listing Agent: Antonio Spagnolo (407-914-0227)

Remarks: SELLER MOTIVATED - PRICE TO SELL - GREAT OPPORTUNITY STUNNING FULLY RENOVATED 3 BEDROOM POOL HOME – PRIME LOCATION IN KISSIMMEE Welcome to this beautifully upgraded 3-bedroom, 1 bonus room, 2-bathroom home located and a spot available with possibility to build a one more bathroom. This property has been completely renovated with high-end finishes throughout and offers the perfect blend of elegance, comfort, and Florida lifestyle living. Fully renovated interior. Premium, first-line flooring throughout. Sophisticated wood panel accent walls. Designer-decorated bedrooms. Completely remodeled kitchen with modern finishes. Updated bathrooms with contemporary style. Extended driveway for additional parking Private heated pool with spa. Outdoor gourmet area perfect for entertaining. Beautiful pond water view with a colonial-style architectural details. Gated community for added security. The open floor plan creates a bright and welcoming atmosphere, ideal for both primary residence, vacation home, or investment property. The backyard is a true retreat, featuring a heated pool and spa overlooking a peaceful pond view — perfect for relaxing evenings or entertaining guests. This home shows pride of ownership and attention to detail in every corner. The bedroom furniture has been removed; the summer kitchen needs to be finished, and the refrigerator was removed because it was broken. Seller is highly motivated and priced to sell. Excellent opportunity in one of Kissimmee’s most sought-after areas, close to major highways, shopping, dining, and attractions.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Francisco Tatagiba Junior (386-517-3488)

Remarks: Townhome available and ready to move in, featuring 3 bedrooms, 2.5 bathrooms, and a one-car garage, located in the gated community of Flora Ridge, conveniently near the Loop. The welcoming entry opens to a well-appointed kitchen with breakfast bar, seamlessly flowing into the open-concept living room and dining area—perfect for everyday living and entertaining. Upstairs, you’ll find three spacious bedrooms, two full bathrooms, and a built-in workstation ideal for remote work or study. Enjoy close proximity to Shopping, Schools, Dining, and more. Schedule your private showing today!

Listing is courtesy of: BROKERS REAL ESTATE GROUP INC (407-770-1464)

Listing Agent: Rich Canelon (407-341-4035)

Remarks: Welcome to this spacious 4-bedroom, 2-bath single-family home located in the desirable Fortune Lakes community of Kissimmee. Built in 2003, this well-maintained property offers 2,085 sq ft of living space on an 8,233 sq ft lot, providing comfort, privacy, and convenience in a prime Central Florida location. This home features a split floor plan, generous living areas, and a layout ideal for both everyday living and entertaining. Recent upgrades include central A/C (2020), water heater (2024), new kitchen appliances, updated kitchen countertops, new carpet and flooring, and a wireless alarm system on all doors and windows. The home also offers a new roof, recently resurfaced pool and pool deck, an upgraded screened enclosure, and a saltwater pool system with a pool pump replaced approximately 2–3 years ago. Exterior features include a 2-car garage, stucco finish, and composition shingle roofing. Located just minutes from major highways, shopping, dining, schools, and medical facilities, this home provides excellent access to everything Kissimmee and Orlando have it. The Fortune Lakes/Remington area is known for its well-kept surroundings, nearby golf options, and strong community appeal. Original Owners.

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

Listing Agent: Jackie San Pedro (407-346-8922)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 3-bath home in the highly desirable Tapestry Phase 5 gated community. Built in 2021, this modern residence features an open-concept layout, high ceilings, and ceramic tile flooring throughout the main living areas, creating a bright and airy feel. ***No street parking. Visitors can park at the clubhouse with restrictions applied.*** The chef-inspired kitchen offers solid surface countertops, stainless steel appliances, and solid wood cabinetry, perfect for entertaining and everyday living. The primary suite is a private retreat with a large walk-in closet and dual-sink en-suite bathroom. Sliding glass doors lead to a covered rear patio overlooking a fully fenced backyard, ideal for outdoor living, pets, or a future pool. Additional features include: 2-car garage Interior laundry room Central A/C Underground utilities Residents of Tapestry enjoy resort-style amenities including: Pool Fitness Center Clubhouse Walking trails 24-hour gated security Located just minutes from The Loop, major shopping, dining, medical centers, and with easy access to 417 & I-4, this home offers unmatched convenience and lifestyle. A rare opportunity in one of Kissimmee’s most sought-after communities.

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

Listing Agent: Karina Garate (407-734-8663)

Remarks: Welcome to this beautifully designed two-story home offering the perfect blend of comfort, style, and functionality. The first floor features a spacious flex room, ideal for a home office, complete with built-in shelving for added organization and charm. Just beyond the entry, the upgraded kitchen impresses with 42-inch cabinetry, granite countertops, stainless steel appliances, and a large center island—a perfect gathering spot for family and friends. The kitchen opens seamlessly to the family room, highlighted by a striking custom stone electric fireplace that adds warmth and elegance to the heart of the home. Off of the rear entry garage is the mud room ideal to keep the home clutter free from everyday items. All bedrooms are thoughtfully located on the second floor, along with a versatile loft that can serve as a media room, playroom, or additional workspace. The primary suite is a true retreat with tray ceilings and features an ensuite bathroom with marble countertops, dual sinks and two spacious walk-in closets. The home’s exterior offers both style and convenience with a rear-entry garage and a paved driveway that enhances the property’s curb appeal. Enjoy resort-style living in a 24-hour manned, gated community offering premium amenities, including an infinity pool, clubhouse, dog park, and multiple playgrounds. Ideally located just minutes from The Loop shopping center, the Florida Turnpike, SR 417, and world-famous theme parks, this home provides unmatched convenience and access to all that Central Florida has to provide.

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

Listing Agent: Jeannie Torres (407-414-3132)

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: One or more photo(s) has been virtually staged. "Huge PRICE REDUCTION for quick sale." Welcome to your dream home in the luxurious Weston Reserve gated community. This stunning former model home combines spacious, thoughtful design with prime location, offering the perfect balance of privacy and accessibility. Situated just about a mile from the Loop shopping complex and walking distance of Flora Ridge Elementary School, Publix supermarket, Floor and Decor, and premium shopping, this property defines "move-in ready." It is also ideally located just a few miles from Disney, Sea World, and about a twenty minute to the Orlando International Airport. Designed for those who love to cook and entertain, the expansive kitchen features rich 42-inch-high wood cabinets, a central island and a galley pantry. High-end upgrades include a fairly new cook top, a new dishwasher and a double convention oven. There are also a wet bar and an elegant half bath by the stairs to the second floor. The kitchen flows seamlessly into a breakfast nook and a light filled family room with custom built ins. Step through the sliding glass doors to your own private paradise. The screened-enclosed poor area, equipped with a baby fence, offers a serene retreat for soaking up the Florida sun or hosting weekend gatherings in a secluded setting. As you entered through the 8ft high front door, you are greeted with an elegant family and dining rooms. On the left is the guest room with its own dedicated bathroom and on the right is the 100 square feet office with custom built-in desk and bookshelves. Go up the recently installed hardwood stairs to the second floor and find two bedrooms which are connected by a Jack and Jill bathroom and the massive primary bedroom which serves as a true sanctuary, boasting dual walk-in closets, double vanities and a luxurious garden tub. The property also features a new roof that was installed in 2021, 2 HVAC systems that were installed less than three years ago along with a fairly new water heater and pool pump and new paint interior and exterior. Don't let this incredible opportunity pass you by. Call for an early showing.

Listing is courtesy of: HOMESTEAD REALTY INC (407-367-4201)

Listing Agent: Patrick Matthews (321-663-2623)

Remarks: One or more photo(s) has been virtually staged. I One or more photo(s) have been virtually staged. Located in the heart of Downtown Kissimmee, just steps from the courthouse, this solid-block, single-story property offers the rare flexibility to live, work, or do both. Featuring 2 bedrooms, 1 bathroom, approximately 736 sq ft, a carport, and a cozy garden area, this property is perfect for anyone seeking a central location with multiple possibilities. Inside, you’ll find a functional layout with a practical kitchen and comfortable living spaces. Built in 1952, the home carries unique charm while offering reliable updates, including a Flintlastic roof installed in 2016 and a 14 SEER, 2-ton A/C unit installed in 2015. What truly sets this opportunity apart is its permitted zoning flexibility. According to city zoning allowances (buyer to verify all details with the City of Kissimmee), this property permits a range of commercial-style uses, including: ? Restaurant ? Retail establishment ? Churches ? Libraries & museums ? Public uses ? Veterinary clinics ? Service establishments Whether you're an investor, a business owner, or a buyer looking for a versatile space in a thriving location, this property offers exceptional potential for the present and the future. Explore additional expansion or conversion opportunities by verifying zoning and building options with the City of Kissimmee. A centrally located, multi-use property like this is hard to find—don’t miss your chance to make it yours.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Naomi Embleton (407-709-6020)

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

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

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

Remarks: 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: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained condo for sale in the desirable gated community of Flora Ridge in Kissimmee. Located on the third floor with convenient elevator access, this residence offers comfort, space, and functionality in a prime location. As soon as you walk in, you’ll be impressed by the open and airy layout, where the living room and dining room flow seamlessly together — perfect for entertaining or relaxing at home. Natural light fills the space, creating a warm and inviting atmosphere. The kitchen offers ample cabinet storage, laminate countertops, and sleek stainless steel appliances, making it both practical and stylish. Just off the kitchen, you’ll find a dedicated laundry room complete with washer and dryer for added convenience. The main bedroom suite is generously sized and filled with natural light. A unique and versatile adjacent room connected to the primary suite can be used as a home office, nursery, sitting room, or even your dream custom closet space. The main bathroom is thoughtfully designed with dual vanity sinks, a walk-in shower with glass doors, a walk-in closet, and a private enclosed toilet room. On the opposite side of the condo, you’ll find two additional bedrooms with a full bathroom in between. The shared bathroom features a bathtub, ideal for guests or family. Bedroom two includes a built-in closet, while bedroom three offers a spacious walk-in closet. Step outside onto the private balcony, the perfect place to unwind in the evenings and enjoy Florida’s beautiful weather. Flora Ridge is a gated community in Kissimmee known for its tranquil, park-like setting and well-maintained grounds. Residents enjoy: Secure gated access for peace of mind, One assigned carport parking, right for two vehicles, Additional community parking spaces for visitors, Assigned overnight guest parking available for visitors, Lush landscaping and garden and water views throughout the neighborhood. Close to the Loop, Turnpike, Access to 417 and the Airport.

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

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

Remarks: This spacious 3-bedroom, 2-bath condo offers a functional layout with the primary suite conveniently located on the first floor, perfect for added privacy and ease of living. Fresh updates include brand new carpet on the first floor and stairs, giving the home a clean, move-in-ready feel. Offered semi-furnished, all furniture currently in the home will convey, making this an easy option for a primary residence, second home, or investment opportunity. Located in a gated community packed with amenities, residents enjoy access to multiple pools, a fitness center, clubhouse, sports courts, playgrounds, and even a private theater - everything you need for both relaxation and entertainment right at your doorstep. The HOA also maintains the roof, which was replaced in 2018, offering added peace of mind. Whether you're searching for a primary residence, vacation getaway, or income-producing property, this community allows short-term rentals, giving you the flexibility to make it your own. Ideally situated just a short drive from Walt Disney World and minutes from The Loop shopping center, you’ll have convenient access to dining, shopping, and entertainment while still enjoying a private, resort-style setting.

Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)

Listing Agent: Carly Ruecker (727-776-7962)

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

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

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

Remarks: Welcome to this stunning move-in ready waterfront home! New Roof in January 2025! Nestled in highly sought-after gated community of Weston Reserve, and in a prime location in Kissimmee. Used as a second home, this impeccable 4-bedroom, 2-bath home offers a spacious open floor plan. Step inside to a bright foyer, high ceilings, and generously sized separate formal living room and dining room. The kitchen is both functional and welcoming, featuring 42” cabinetry with ample space, beautiful appliances, cozy breakfast nook, and openly leads to dining and family room – ideal for everyday living, hosting and entertaining. Sliding glass doors in both family room and primary suite open up to an oversized screened LANAI overlooking the beautiful pond and conservation area with serene atmosphere and no rear neighbors. The spacious primary suite boasts 2 walk-in closets, a peaceful retreat with private access to the patio and backyard—ideal for enjoying quiet mornings outdoors, and tranquil relaxation after a long day. The ensuite bathroom includes a beautifully tiled walk-in shower, a dual vanity with ample storage, and a huge spa tub. All 4 bedrooms, family room and Lanai has ceiling fans installed. Extended patio and backyard are ideal for BBQs, big family gatherings, and for little ones or pets to play around. Residents enjoy resort-style amenities, including a community pool, sand volleyball court, playground, BBQ area, and a private gated path access to Kissimmee Loop Trail, and the Shingle Creek Regional Trail. Located within close proximity to the Town Loop Shopping Center, this home provides unmatched convenience to restaurants, retails, gyms, supermarkets and everyday essentials. Conveniently located near major highways, Hospitals, schools, and churches. Orlando International Airport (MCO), Theme Parks, and International Drive’s iconic attractions are all within easy reach. Easy access and prime location make this home ideal for families, professionals, or anyone looking to enjoy the best of Florida living. Don’t miss your chance to make this wonderful property your dream home—schedule your private showing today!

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

Listing Agent: Dolly Strahan (407-234-8321)

Remarks: **WATERFRONT** If you're looking for an open-floor plan move-in ready home with a waterfront view, you've found it. Located in the heart of Hunter's Creek less than 5 minutes from The Loop Town Center, this home is ready to meet its new owners. Highlights: Three spacious bedrooms with walk-in California style closets, high ceilings, tons of windows and natural light, long entry corridor, gourmet kitchen with tiled mosaic floors, formal dining area PLUS a breakfast nook area, and a screened-in front porch and rear porch. Laundry room features custom built-in cabinets for extra storage and washer/dryer is also included. Major appliances: Roof (2020) AC (2019). Home is also equipped with wired security cameras, an irrigation system, and rain gutters. But let's be honest, the real selling point is that WATER VIEW. Talk about peace and serenity! Enjoy resort-style community amenities such as a community pool, clubhouse, fitness center, tennis courts, and walking trails. You'll never be bored! HOA covers your lawn maintenance and let's not forget, the community is gated and private. Located close to shopping plazas, restaurants, entertainment, medical facilities and highways, everything you could ever want is within a mile radius. Bonus: Disney is only 10 minutes away!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Angie Kollcaku (407-454-4078)

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

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

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