Homes for Sale Near Osceola High School in Kissimmee - 96 homes

Remarks: One or more photo(s) has been virtually staged. Seller is Highly Motivated – Bring All Offers! Welcome to the gated community of Windsor Point, where comfort, convenience, and natural beauty come together. This spacious 3-bedroom, 2-bath residence with a versatile flex room offers a thoughtfully designed layout ideal for both entertaining and everyday living. Upon entering the home, you’re greeted by a welcoming foyer that opens into a bright formal living room—perfect for hosting guests or creating a peaceful sitting area. The split floor plan provides privacy, while the expansive family room serves as the heart of the home, offering plenty of space for gatherings, movie nights, or relaxing after a long day. Sliding glass doors lead to a generously sized backyard, fully enclosed with durable vinyl fencing for privacy and security. Whether you envision weekend barbecues, a play area, space for pets, or a future pool, this yard provides endless possibilities. The home features easy-care ceramic tile flooring throughout—ideal for Florida living. The spacious kitchen is designed for functionality and flow, complete with abundant cabinetry, ample counter space, and an open layout that allows you to stay connected while cooking or entertaining. The flex room can easily function as a home office, workout room, craft room, or homeschool space. Prime Location: Located just 5 minutes from The Loop, featuring upscale shopping, restaurants, and a movie theater. Enjoy quick access to major highways, including Osceola Parkway, John Young Parkway, and the Florida Turnpike, for easy commuting. World-famous attractions such as Disney theme parks, Disney Springs, and Old Town are just 6–10 miles away. Orlando International Airport (MCO) is approximately 15 miles from the property. This home offers space, flexibility, and a highly desirable location within a secure community—making it an excellent opportunity for primary homeowners, second-home buyers, or investors alike. Schedule your private tour today to fully appreciate this home's charm!

Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)

Listing Agent: Tiffany Greer (407-709-0582)

Remarks: $5,000 BUYER INCENTIVE. Use it toward closing costs, upgrades, or a rate buy-down. This 3 bedroom, 2.5 bath townhouse offers 1,702 square feet of well designed living space in a prime location. Situated directly across from the community pool and playground, the home provides immediate access to top neighborhood amenities. The interior features an open main floor layout, ideal for both entertaining and daily functionality. Upstairs, the primary suite is complemented by two additional bedrooms and a full bath, offering flexibility for guests, a home office, or a growing household. Conveniently located near major shopping centers, restaurants, and essential services, this property combines comfort, convenience, and community living. A strong opportunity for buyers seeking a well maintained home in a desirable area.

Listing is courtesy of: REAL ESTATE HOUSE FL INC (407-484-0005)

Listing Agent: Monica Fehlberg (407-497-9710)

Remarks: Welcome to resort-style living in one of Kissimmee's most amenity-rich gated communities. This spacious 3-bedroom, 2-bathroom townhouse at Venetian Bay Villages offers an unbeatable combination of space, security, and lifestyle — all at a price that's hard to match in Central Florida. THE LAYOUT: This two-story floor plan features a ground-floor master suite — ideal for homeowners who want easy access or for guest privacy. Two additional bedrooms upstairs provide natural separation for family members or roommates. The open-concept living, dining, and kitchen area makes the space feel larger than the square footage suggests. MOVE-IN READY: The unit has been freshly repainted throughout and is vacant — ready for immediate occupancy the day you close. THE COMMUNITY: Venetian Bay Villages is a 24-hour staffed guard-gated community with amenities that rival full resort properties: 4 pools and a heated jacuzzi, fitness center, clubhouse with theater and game room, tennis, basketball and volleyball courts, 3 catch-and-release fishing lakes, BBQ stations, playgrounds, and a car wash area. HOA covers exterior maintenance and landscaping — truly low-maintenance ownership. THE LOCATION: Minutes from I-4 and US-192 — 13 miles to Walt Disney World, 12 to SeaWorld, 16 to Universal Studios. Steps from Walmart, Publix, Target, Burlington, Ross and The Loop shopping center. Osceola Regional Medical Center is just 2 miles away. RENTAL FRIENDLY: Both long-term leases and weekly vacation rentals (7-day minimum) are permitted with no HOA waiting period — ideal for investors who want flexibility.

Listing is courtesy of: KEYS REALTY REDEFINED LLC (305-707-0373)

Listing Agent: Randal Longo (855-944-3525)

Remarks: Under contract-accepting backup offers. Welcome to this 3 bedroom, 2 bathroom home located in a gated community in the heart of Kissimmee, Florida, just minutes from The Loop, a popular shopping, dining, and entertainment destination. Enjoy convenient access to Walt Disney World (approximately 25 minutes) as well as Universal Orlando and Central Florida’s world-famous theme parks, placing you close to everything the Orlando area has to offer. This move-in ready home features a desirable split floor plan with spacious living areas and thoughtful updates throughout. Recent improvements include a 2025 roof, newer AC (2017), and a water softener system providing added peace of mind. Inside, you'll find fresh interior paint, new baseboards, and a refreshed front door that give the home a clean and welcoming feel. The layout offers generously sized bedrooms, along with a kitchen and family room combination that creates a comfortable space for gathering and entertaining. A formal living and dining area provides additional flexibility and can easily function as a home office, flex space, additional living area, or hobby room. Other Residents of this gated Kissimmee community enjoy access to neighborhood amenities including a community pool, playground, and clubhouse, adding to the convenience and lifestyle this location offers. With easy access to shopping, dining, major roadways, and Central Florida attractions, this Kissimmee home offers comfort, convenience, and the opportunity to make it your own. Call to schedule your private showing! SELLER WILL PROVIDE $5000 CREDIT TOWARD NEW FLOORING.

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

Listing Agent: Suzette Berkhalter (407-864-6206)

Remarks: Discover an incredible opportunity. NEW ROOF 2022 it has 4 bedrooms with 2 masters suite, 3 bathroom home with 2 car garage in the sought-after Magical Landings community in Kissimmee! This well-maintained home offers exceptional value with just a few minor cosmetic touches needed to make it truly shine. This property is perfect for families, multi-generational living, or even a vacation home. The open-concept layout flows beautifully into a large great room, creating an inviting space ideal for entertaining and everyday living. Step outside to your own private oasis, an enclosed, screened, and heated in-ground pool, perfect for enjoying Florida living year-round in total privacy. Major upgrades include a new roof, giving peace of mind to the next owner. The home is also ideally located just minutes from the Florida Turnpike, providing easy access to everything Central Florida has to offer, including world-famous attractions like Walt Disney World. Situated in a gated community, close to schools, shopping, dining, and major roadways, this home truly combines convenience, comfort, and value. Priced to sell—this opportunity will not last! Schedule your private tour today and submit your offer before it’s gone.

Listing is courtesy of: ATRIUM REALTY, LLC (833-919-1190)

Listing Agent: Ernani Sena (774-258-0635)

Remarks: 3-bedroom, 2-bath home with a screened-in pool and pond view. No HOA. Conveniently located near shopping, Florida’s Turnpike, theme parks, and about 30 minutes to downtown Orlando.

Listing is courtesy of: REALTY ONE GROUP SUNSHINE (727-325-5843)

Listing Agent: Troy Funk (941-241-3850)

Remarks: Welcome to this beautifully appointed two-story corner-lot home nestled in the heart of Kissimmee. Featuring exceptional curb appeal with a brick-paved driveway, stone-accented façade, and meticulously maintained landscaping, this residence exudes elegance from the moment you arrive. The seller will pay off the remaining balance of the solar panels at closing. Step inside to an open-concept layout filled with natural light, where contemporary design meets comfort. The main living area includes elegant tile flooring, modern light fixtures, and custom wall details that add a touch of sophistication. The gourmet kitchen serves as a centerpiece, complete with granite countertops, an oversized island, and stainless steel appliances, all seamlessly connected to the dining and living spaces—ideal for both everyday living and entertaining. Upstairs, spacious bedrooms provide abundant natural light, while the primary suite serves as a private retreat, showcasing a spa-like ensuite with dual vanities, a soaking tub, and a walk-in shower. Situated on a desirable corner lot, the home also includes a fully fenced backyard perfect for relaxing or hosting gatherings. Conveniently located near major highways, premier shopping, dining, and top-rated schools, this home combines style, function, and location in one exceptional listing. The property includes solar panels, which significantly reduce electricity costs. The system will be paid off by the seller at closing, ensuring the new owner benefits from the energy savings without any remaining balance or financial obligation.

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

Listing Agent: Vicente Virgilio (407-401-7447)

Remarks: 4 bedroom 2 bath home in a gated community. Living/dining room, large kitchen with eating space. 2 car garage. Pond view from the back of the house and conservation view from in part of the front.

Listing is courtesy of: REALTY SERVICES OF AMERICA (407-319-4113)

Listing Agent: Edgar Gonzalez (321-285-0472)

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: Best value in the city of Kissimmee! This upgraded 3-bedroom, 1-bath home is one of the most affordable properties in the entire zip code—an incredible opportunity you don’t want to miss. Move-in ready with recent improvements, this property offers the added benefit of NO HOA, providing freedom and flexibility for homeowners and investors alike. Ideally located in Kissimmee, just approximately 20 minutes from Orlando International Airport and 25 minutes from Walt Disney World. Enjoy easy access to major roadways including US-192, John Young Parkway, Osceola Parkway, and Florida’s Turnpike, making commuting a breeze. Conveniently close to shopping, dining, and schools. Perfect for first-time buyers or investors looking for strong value in a high-demand area!

Listing is courtesy of: FLORIDA LAKES REALTY (407-593-9087)

Listing Agent: Tatiana Diaz (407-593-9087)

Remarks: Welcome to this beautifully presented pool home in Kissimmee! This spacious residence showcases the kitchen featuring elegant gold fixtures and sleek stainless steel appliances, including a range, refrigerator, dishwasher, and microwave. Designed for both comfort and entertaining, the home offers a bright living room and a cozy dinette space. Enjoy the clean, modern feel of no carpet throughout, complemented by stylish flooring and ceiling fans in several rooms for added comfort. Both bathrooms have been tastefully updated, enhancing the home’s contemporary appeal. Step outside to a large screened-in patio overlooking a sparkling open-air pool—perfect for relaxing or hosting gatherings. The fully fenced backyard adds an extra layer of privacy, making this home a true retreat.***Home square footage, taxes, lot sizes, and schools; are to be independently verified.***

Listing is courtesy of: ALLEGIANT MANAGEMENT GROUP INC (407-557-3164)

Listing Agent: Elizabeth Santiago Moyet (321-231-2105)

Remarks: Welcome to this well-maintained 3-bedroom, 2-bathroom condo villa located in the gated community of Bella Vista Condominiums in Kissimmee. Offering 1,246 sq.ft. of heated living space, this property features a functional two-story layout with the kitchen, living area, and primary bedroom on the first floor, and bedrooms 2 and 3 on the second floor. The unit provides comfortable living spaces with good natural light throughout. Residents enjoy access to community amenities including a swimming pool, fitness center, and recreational areas. Conveniently located near shopping, dining, schools, and major roadways, with easy access to local attractions and Orlando. Schedule your showing today!

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

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

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: Location, location! 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: Welcome! Enjoy no rear neighbors forever, and a low-key HOA, with this well-appointed home, which offers five spacious bedrooms, four and a half bathrooms, and exceptional flexibility for family living, hosting guests, or creating dedicated work and relaxation spaces. The open floor plan boasts 4,964 square feet, with high ceilings, a gourmet kitchen with premium finishes, and multiple living areas designed for comfort and entertaining. A dedicated theater room can easily serve as a sixth bedroom, while the oversized 3-car garage provides ample storage. Each bedroom offers versatile options for family, home offices, or guest quarters, and generous square footage creates a natural balance between shared spaces and private retreats. Nestled on a 0.54-acre lot in a small, private gated community, this property combines privacy and convenience—located near shopping, lakefront parks, quality schools, SunRail, and minutes from charming downtown Kissimmee. Schedule your private tour today!

Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)

Listing Agent: Joseph Doher (407-203-0007)

Remarks: High-Demand Rental Investment – Immediate Cash Flow Turnkey condo in a prime rental corridor of Kissimmee, just minutes from major highways, shopping, and employment hubs. Currently generating $1,750/month with lease in place through July 31, 2026—income from day one. Located in an area with strong and consistent rental demand, plus short-term rental potential (buyer to verify with HOA) for added upside. Tenant in place—no vacancy, no delays. Ideal for investors seeking immediate return in a proven rental market.

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 this beautifully upgraded 3 bedroom 2.5 bathroom townhome at Heritage Key Villas in Kissimmee, offering comfort, style and a peaceful pond view. Step inside and immediately appreciate the modern upgrades throughout. The entire home features luxury vinyl plank flooring on the first floor, staircase and upstairs, creating a cohesive and elegant look while being durable and easy to maintain. The kitchen features a large granite island, ample cabinetry and an open layout that flows seamlessly into the dining and living area. Upstairs the secondary bathroom has plenty of cabinet space and has an enclosed shower. Light fixtures, and ceiling fans have been tastefully replaced, giving he property a fresh modern feel. New toilets. One year old appliances including the washer and dryer. The three bedrooms provide comfortable living space. The main bedroom has serene pond views from two windows. Screened in porch overlooking the pond. Sit and enjoy the relaxing view. The community residents enjoy a community pool, spa, fitness center, playground and a clubhouse. Close to shopping, dining and major highways.

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

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

Remarks: Welcome to this beautiful, completely renovated villa. Location, location, location! This area in downtown Kissimmee is situated close to The Loop Shopping Center, featuring all the best shops and restaurants. It also offers access to top-tier medical care, including hospitals, medical specialists, and excellent healthcare services. This villa has been fully renovated and features stainless steel appliances, granite countertops, a washer and dryer, updated bathrooms, and perfectly coordinated wood flooring. Additionally, it includes two parking spaces directly in front of the property. The community also offers a swimming pool and a recreational area.

Listing is courtesy of: FLORIDA FANTASY REAL ESTATE INC (407-397-9039)

Listing Agent: Yolanda Gonzalez (407-535-9722)

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

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

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

Remarks: This beautiful townhouse is perfectly situated a short walk from the community heated swimming pool, spa, 24-hour fitness, clubhouse, and business center—everything you need right at your doorstep for resort style living! Located in a secure, gated community and move-in ready, this spacious 3-bedroom, 2.5-bath home offers both comfort and convenience in every detail. The large, bright kitchen features ample cabinetry, a newer granite island, and a double oven—ideal for everyday meals and effortless entertaining. Adjacent to the kitchen, the expansive dining room boasts an elegant tray ceiling and recessed lighting, creating a modern, upscale ambiance. The generously sized living room offers plenty of space for relaxing or hosting guests. Sliding glass doors lead to a screened-in patio—perfect for enjoying beautiful Florida days in comfort and style. Upstairs, the desirable split floor plan places the primary bedroom on one end for added privacy, with the second and third bedrooms located on the opposite side. One of the secondary bedrooms can easily be converted into a home office, making it perfect for today’s work-from-home lifestyle. The spacious primary suite includes a walk-in closet and a private ensuite with a tub/shower combination, granite countertop, and ample storage. The guest bathroom features a walk-in shower, granite countertops, and generous storage as well. All bathrooms are finished with granite countertops, adding a sleek, modern touch throughout. The first floor is finished with tile for easy maintenance, while the upstairs bathrooms also feature tile flooring, and the bedrooms are carpeted for added comfort. The home has a new AC unit (2024). Entire house painted (2024). A prime location just moments from Disney World, Silver Spur Arena and other major attractions, shopping and entertainment.

Listing is courtesy of: RANDOLPH & CO. (407-454-0214)

Listing Agent: Ron Randolph (407-454-0214)