Homes for Sale Near Osceola High School in Kissimmee - 77 homes

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)

Remarks: Opportunity is knocking at Terra Condo’s in Kissimmee! This FIRST FLOOR ~ END-UNIT condo is being sold FURNISHED, and is priced so you can bring your vision and make it your own. Whether you are ready to modernize with fresh finishes or lean into a bit of its vintage charm, the possibilities are wide open here. With just a little TLC, this light and bright space can truly shine! A covered front entry welcomes you inside to a nice layout featuring dedicated living and dining spaces that feel open yet defined. Natural light pours in thanks to the end-unit location, giving the home an airy feel throughout. The galley-style kitchen offers a generous amount of cabinet and counter space, providing a functional layout that is ready for your personal touch. Off the dining area, sliding glass doors lead to a SCREENED LANAI complete with a convenient STORAGE closet – perfect for enjoying Florida’s year-round weather. Located in a GATED ACCESS, all owner-occupied community, Terra Condo offers amenities designed for easy living, including a COMMUNITY POOL and clubhouse, with water, sewer, and trash included in the HOA. The location puts you close to shopping, dining, local lakes, area resorts, and world-famous theme parks, making it ideal as a primary residence or seasonal getaway! If you have been looking for an affordable first-floor condo in Kissimmee with room to add value and personalize, this is your chance. Bring your ideas and unlock the potential! **Seller may consider buyer concessions if made in an offer**

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Beautiful Condo in Gated Bella Vista Community – Kissimmee! Move-in ready and perfect for homeowners or investors! This first-floor unit has been freshly painted in neutral tones and features a desirable split floor plan with 2 master suites and 2 full bathrooms. Enjoy abundant natural light and an open-concept living and dining area, ideal for entertaining. The kitchen is equipped with stainless steel appliances, granite countertops, and a breakfast bar, offering both style and functionality. Step out onto the screened-in patio and relax while enjoying peaceful views of the tennis court and lush, mature landscaping. Bella Vista offers excellent amenities, including a community pool, tennis court, fitness center, BBQ area, and playground. Conveniently located near Hwy 192, Historic Downtown Kissimmee, theme parks, shopping centers, outlets, and The LOOP, this property combines comfort with accessibility. HOA includes water, sewer, and insurance! Spacious, well-maintained, and ready for its new owner. Schedule your private showing today!

Listing is courtesy of: SUNNY 365 REALTY GROUP (407-574-7048)

Listing Agent: Isabel Sirizzotti (407-361-8236)

Remarks: Welcome to this well-maintained 2-bedroom, 1-bathroom condo located in the desirable Terra Condos community in Kissimmee, Florida. Whether you're looking for a cozy full-time residence, a vacation home, or a promising investment property, this condo offers comfort, convenience, and a prime location. Situated just minutes from Kissimmee Gateway Airport, and close to an abundance of shops, restaurants, parks, and major highways, this location puts everything you need within easy reach. Plus, you're only a short drive from some of Central Florida’s most popular attractions, including Gatorland, Discovery Cove, SeaWorld Orlando, and the Disney Theme Parks. Inside, you'll find a functional layout with two spacious bedrooms, a full bathroom, and an open living and dining area perfect for relaxing or entertaining. The kitchen offers ample cabinet space, and the large windows provide plenty of natural light. Community Highlight include a Community pool for residents to enjoy and the fees include: pest control, sewer, trash, and water — for added value and peace of mind. Whether you're looking to invest or unwind, this affordable and low-maintenance condo offers a great opportunity in the heart of Kissimmee. Don’t miss out—schedule your showing today!

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

Listing Agent: Vanessa Santiago (407-995-4630)