Homes for Sale Near Osceola High School in Kissimmee - 144 homes

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: ATTENTION BUYERS: Primary residence, INVESTORS for Airbnb or short-term rentals. FIESTA KEY is a resort-style and peaceful living 24-gated community with an excellent location close to Disney parks, restaurants, shopping, schools, and more! This townhome has 3 bedrooms, 2 bathrooms, and the laundry upstairs for privacy. You will enjoy the first floor in an open floor plan, the living room, and the half bathroom. You will love the lanai for your morning coffee or to read a book. Kitchen appliances included. There is parking for 4 vehicles. Amenities: clubhouse, fitness center, tennis court, walking trails, walking distance to clubhouse, resort-style pool, and a 2nd. pool inside the gated community. Live free and unworried about outside maintenance because the HOA takes care of it: roof, painting, lawn, etc.

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

Listing Agent: Maribel Minarro (407-908-3522)

Remarks: Beautiful 2-Story Home in Gated Community – Great for Living, Vacation, or Rental Income This is a wonderful opportunity to own a fully furnished 2-story home located in a quiet, gated community with 24/7 security and great amenities. The home is in excellent condition and is currently being used as a short-term rental with a 5-star rating on Airbnb. It’s located in a very convenient area — just minutes away from Walmart, Disney parks, Highway 192, and Plaza del Sol. Whether you're looking for a permanent home, a vacation spot, or an investment property, this one offers a lot of value and flexibility. The home is already listed and performing well on Airbnb. If the buyer is interested, we’re happy to transfer the current and upcoming Airbnb bookings to make the transition smooth and help you start earning right away. Inside, the home is clean, spacious, and comes fully furnished, so it’s truly turn-key — ready for living or renting without any extra effort. The community offers plenty of amenities for guests and residents, including a swimming pool, clubhouse, gym, and more. It’s a safe, family-friendly neighborhood that’s also appealing to tourists due to its close proximity to major attractions. Whether you plan to live here full-time, use it as a vacation getaway, or continue running it as a short-term rental, this home is a smart choice in a great location.

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

Listing Agent: Juan Garcia Betancur (407-535-0909)

Remarks: LOCATION, LOCATION, LOCATION! This fantastic property features a 2025 NEW manufactured home and is truly ready for move-in! ?It boasts three spacious bedrooms and two comfortable full bathrooms. Enjoy the sleek look and easy maintenance vinyl flooring throughout the entire home. ?A sliding door from the living area leads out to a relaxing patio—perfect for hosting barbecues and spending quality time with family and friends. The home also includes a spacious living and dining area, an eating space in the kitchen, and all appliances are included. ?Recent updates include a new drain field. The home is centrally located with incredibly easy access to shopping, restaurants, and the Orlando International Airport. ?Schedule your showing today and make this beautiful home yours! The seller is highly motivated.

Listing is courtesy of: CENTRAL REALTY GROUP AND PROPERTIES (407-582-9011)

Listing Agent: Bernardino Castorani (407-582-9011)

Remarks: Feast your eyes on this Stunning 5BR/3BA pool home in the sought-after Gated Ashley Cove community. Here you can enjoy 2,896 sq ft of luxury. The home offers a desirable 3-way split-bedroom plan, a Formal living room with a wood-burning fireplace, a formal dining room, and a spacious family room. For those who work from home, there's a separate office with built-in shelving. The kitchen is well-appointed with beautiful granite countertops, a center island, and crown-molded cabinetry. Eat at the comfortable breakfast bar, the dinette, or the dining room. The master retreat boasts a tray ceiling, two walk-in closets, a garden tub, a separate shower, dual vanities, and a set of french doors that lead out to the covered lanai and screened pool. The spacious pool deck, adorned with beautiful brick pavers, is ideal for relaxing and entertaining. The new roof (2023) and AC (2025) provide peace of mind for years to come. Other improvements include: hot water heater (2020), exterior paint (2026), new light fixtures (2022), pool re-screen (2025), and newer appliances (2023 & 2026). The 12 ft ceiling and the 4 sets of french doors give this home a beautiful open appeal. The pre-wired surround sound speakers convey. This home is move-in ready and waiting for its next owner. All appliances convey. Minutes to Lake Toho, attractions, shopping, hospitals, and expressways.

Listing is courtesy of: FLORIDA REAL ESTATE PROPERTIES LLC (407-951-7810)

Listing Agent: Joyce Sanders (407-234-4680)

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: NEW PRICE! Property is Eligible for Free 1% interest rate Buydown for the first 12 months until June 30, 2026!!! 3-bedroom, 2-bathroom home located in a desirable area of Kissimmee, Florida. This property offers the freedom of NO HOA and NO CDD, making it a perfect option for homeowners or investors looking for flexibility and lower monthly expenses. The home features a functional layout with comfortable living spaces, ideal for families or those who enjoy entertaining. Conveniently situated near major highways, shopping centers, restaurants, schools, and just minutes from world-famous attractions in Central Florida. Kissimmee is known for its strategic location near Orlando and major theme parks, while also offering access to parks, lakes, and outdoor recreation throughout the area. Whether you are looking for a primary residence, vacation home, or investment property, this home offers an excellent opportunity in a rapidly growing Central Florida market. Don’t miss the chance to own a property in one of the most convenient and sought-after locations in the area. Additional Exterior and Interior property photos will be uploaded!

Listing is courtesy of: CAPITAL HOMES INC (800-642-0668)

Listing Agent: Alcides Gonzalez (407-267-6868)

Remarks: Under contract-accepting backup offers. 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: Under contract-accepting backup offers. Welcome to this stunning 3-bedroom, 2.5-bathroom townhouse located in the highly desirable gated community of Townhomes of Flora Ridge. Perfectly positioned in the heart of Kissimmee, this home offers the ideal blend of comfort, convenience, and serene surroundings. Enjoy breathtaking lake views right from your home which are perfect for relaxing mornings and peaceful evenings. The community features family-friendly amenities including a playground and tennis court, all within a quiet, well-maintained neighborhood that provides both security and tranquility. Location is everything, and this property delivers. Just minutes from The Loop Shopping Center, you'll have easy access to shopping, dining, entertainment, and major retailers like Lowe’s. You’re also close to medical centers, hospitals, and major highways, making daily commuting effortless. Plus, world-famous attractions like Walt Disney World Resort are just a short drive away. Whether you're looking for a primary residence or a strong investment opportunity, this property checks all the boxes in one of Kissimmee’s most convenient and sought-after locations. Don’t miss your chance—schedule your private showing today.

Listing is courtesy of: VITAL REALTY GROUP INC (407-944-1833)

Listing Agent: Daniel Santos (407-413-2548)

Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bathroom home located in a highly sought-after neighborhood! Freshly updated with new exterior paint and the roof was replaced in 2023. Inside, you'll find beautiful tile flooring throughout, providing a sleek, low-maintenance aesthetic. The spacious layout features a bright and airy living area, perfect for both relaxation and entertaining. Enjoy the added privacy of no rear neighbors, creating a serene backyard space to unwind and enjoy the outdoors. With proximity to Disney, Universal, Sea World, shopping, schools, and local amenities, this home is ideally situated for convenience and ease of living.

Listing is courtesy of: TOHO REALTY GROUP, LLC (407-437-2893)

Listing Agent: Kerriann Sullivan (407-437-2893)

Remarks: Investment Opportunity – Tenant in Place Until October 2026! Welcome to this spacious 2-bedroom, 2-bath condo located in the heart of Kissimmee, just minutes from Walt Disney World, Universal, and major shopping and dining. This well-maintained unit features an open-concept layout, fully equipped kitchen, and a private balcony perfect for enjoying Florida’s sunshine. Currently leased at $1,700/month through October 2026, this property offers immediate rental income in a high-demand location. Whether you’re expanding your investment portfolio or seeking a vacation retreat with long-term tenants already in place, this condo is a solid choice. With a low-maintenance lifestyle and strong rental potential, this is your chance to own a profitable piece of Central Florida real estate. Don’t miss this opportunity—secure your investment today!

Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)

Listing Agent: Adriana Sanchez (321-947-4014)

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: Best value in the city of Kissimmee! CASH ONLY. 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: NO HOA! You won't want to skip viewing this well maintained 4-bedroom 2-bathroom home. Not many home come up for sale in this sought after community of Kings Point. The mature oak trees and landscaping throughout the neighborhood. The home itself sits on a large lot. As you enter through the front door you will admire the stone wood burning fire place in the formal living space. The double doors lead to the primary bedroom with a dream en suite bathroom. You will find a walk-in shower and separate tub, double vanity, and designated make up vanity. The sky light provides natural light with an amazing walk-in closet. Three other bedrooms with easy to clean laminate flooring. The kitchen provides ample storage and an island. Enjoy your morning coffee or tea on the spacious screened in back porch. The back yard offers endless possibilities install a pool for those hot Florida days, plenty of room for family/friend gatherings, storage for the toys. The back yard is completely enclosed by a vinyl fenced for extra privacy. The roof was replaced in 2018. Hot water heater is 3 yrs old, AC is 2026, blown insulation in attic, sprinkler system. Don't wait to schedule a private showing.

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

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

Remarks: Under contract-accepting backup offers. Own a resort-style property near Disney at an affordable price — with the flexibility to live in it, rent it short-term, or both. Priced to sell and packed with value, this beautifully maintained 3-bedroom, 2-bath townhouse in the highly sought-after gated community of Venetian Bay Villages offers the perfect blend of comfort, flexibility, and resort-style living. Featuring a desirable two-story layout with a spacious first-floor primary suite, this home is ideal for full-time residents, vacation homeowners, or investors seeking a turnkey opportunity in the heart of Central Florida. Freshly painted and move-in ready, the open-concept design creates a bright and inviting atmosphere with seamless flow between the living, dining, and kitchen areas. Upstairs, two additional bedrooms provide privacy and versatility for guests, family, or rental use. Residents enjoy access to exceptional amenities including multiple resort-style pools, heated spa, fitness center, clubhouse, theater room, game room, tennis, basketball and volleyball courts, playgrounds, scenic fishing lakes, BBQ areas, and 24-hour guard-gated security. The HOA also covers exterior maintenance and landscaping, making ownership easy and low maintenance. Located just minutes from major highways, world-famous attractions, shopping, dining, and medical facilities, this property delivers outstanding convenience and lifestyle appeal. Short-term vacation rentals and long-term leasing are both allowed with no waiting period, making this an excellent opportunity for investors or buyers looking for maximum flexibility. Don’t miss this competitively priced opportunity in one of Kissimmee’s most amenity-rich communities.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Marcelo Gaitan Estabridis (863-399-5675)

Remarks: *Price Improvement!* Welcome to this stunning 5-bedroom, 4-bathroom Colonial-style pool home located in the highly sought-after gated community of Ashley Cove. This exceptional residence blends timeless elegance with modern upgrades, offering a truly one-of-a-kind living experience. From the moment you enter, you’re greeted by a grand spiral staircase and soaring high ceilings, complemented by rich hardwood flooring and exquisite, high-value chandeliers that add character and sophistication throughout the home. The spacious living room features a cozy fireplace, while large windows flood the home with natural light, highlighting the generous room sizes and thoughtful layout. The ground floor boasts a luxurious primary suite with two walk-in closets, a beautifully updated modern bathroom, complete with dual sinks, a large walk-in shower, and a relaxing soaking tub. The kitchen is both stylish and functional, featuring granite countertops, hardwood cabinetry, and stainless steel appliances including a range, microwave, dishwasher, and refrigerator. A renovated laundry room is also conveniently located on the main level. Upstairs, enjoy a unique movie theater room with a private balcony overlooking the expansive property and an additional bonus room! Situated on an oversized, fully fenced lot with no rear neighbors, the outdoor space offers privacy and tranquility. The screened-in pool and spa include a child safety net, creating the perfect setting for year-round enjoyment. Major updates include new pool tiles and pool re-surfacing in 2025. The property is surrounded by eight beautiful oak trees, three of which were recently removed in 2026 for hurricane safety. Additional features include a 3-car garage and numerous updates: new pool pump (2023), pool re-surfaced (2025), roof replacement (2019), updated A/C units (2018 & 2021), electrical updates (2025), new hot water heater (2026), and fresh interior paint (2025). Conveniently located near Lake Tohopekaliga, with easy access to the Florida Turnpike, and just minutes from Kissimmee, NeoCity, major attractions, shopping, and dining this home truly has it all. Schedule your showing today!

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Rocki Sanchez (407-738-7989)

Remarks: Under contract-accepting backup offers. Seize the chance to explore this inviting townhome, ready for you to move in and make it your own. Featuring two spacious bedrooms and a versatile loft, this area can easily be transformed into a third bedroom, a productive home office, or a cozy family room—tailored to fit your lifestyle. Recent upgrades, including a brand-new roof finished in January 2025 and plush carpeting installed in November, offer peace of mind and comfort. Situated in an ideal location, you’ll find yourself just moments away from bustling shopping centers and The Loop, a lively hub filled with popular restaurants and major retailers like BJ's, JC Penney, Ross, Rooms To Go, and Hobby Lobby. Beyond the conveniences of daily living, the townhome’s proximity to Orlando’s renowned attractions—such as Disney World, SeaWorld, Universal Studios, and Orlando International Airport—ensures endless entertainment and travel possibilities right at your doorstep. Be sure to put this exceptional home at the top of your viewing list—it’s an opportunity you won’t want to miss!

Listing is courtesy of: FLORIDA PROPERTY HOMES (407-728-4650)

Listing Agent: Luis Cabrera (407-728-4650)

Remarks: Situated on an oversized 0.44-acre cul-de-sac lot, this beautifully reimagined residence offers a seamless blend of modern style, comfort, and functionality. The open concept floor plan is designed for both everyday living and entertaining, highlighted by a stunning custom kitchen featuring integrated cooktop countertops, double wall ovens, and a cohesive design aesthetic carried throughout the home. Additional upgrades include impact resistant aluminum frame windows for enhanced durability and peace of mind, along with a complete home water filtration and softener system for improved water quality. The home also features a custom aluminum garage door, adding both durability and refined curb appeal. Step outside to enjoy your own private tennis court and expansive outdoor space, providing endless opportunities for recreation, relaxation, and enjoying the Florida lifestyle. Conveniently located just minutes from NeoCity, one of Central Florida’s fastest-growing innovation and technology hubs, this home is ideally positioned to benefit from the continued growth and investment shaping the surrounding area. Combining a generous homesite, quality enhancements, and an exceptional location, this property presents a unique opportunity for those seeking both space and convenience. As an added bonus, the home may be offered fully furnished, allowing for a truly seamless move-in experience.

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

Listing Agent: Jonah Mas (407-750-7095)

Remarks: Under contract-accepting backup offers. 3-bedroom, 2-bathroom home offering 1,592 square feet of comfortable living space in the heart of Kissimmee. This property features a functional layout with spacious living area.The kitchen flows seamlessly into the main living space, making it ideal for both everyday living and entertaining. Situated in a convenient location near shopping, dining, schools, medical facilities, and major roadways including Osceola Parkway, US-192, and Florida’s Turnpike. Easy access to Orlando attractions and employment centers. Major update: Roof installed in 2021, providing peace of mind and long-term value. Whether you're a first-time buyer, downsizing, or seeking an investment opportunity, this property offers solid value in a central location. Schedule your private showing today.

Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)

Listing Agent: Hector Pagan, Pa (407-791-4858)

Remarks: Under contract-accepting backup offers. Rare Find in Adriane Park! Located in highly sought-after community of only 55 homes, known for its peaceful setting, spacious lots, and convenient location. This beautifully maintained 4-bedroom, 3 full bathroom home offers 2,444 heated square feet with a functional 3-way split floor plan. As you enter, you are welcomed by a spacious living and dining room featuring crown molding, chair rail accents, custom drapes, soaring 10-foot ceilings, and an abundance of natural light from four skylights throughout the home. The dining room connects conveniently to the kitchen through a charming swinging door. The spacious kitchen features granite countertops, a breakfast bar, dinette area, skylight, and plenty of storage space. Matching GE Stainless appliances. The kitchen opens to the inviting family room with a cozy wood-burning fireplace and French doors leading to the oversized screened lanai. Privately situated off the family room, the primary suite offers French door access, a walk-in closet, and an ensuite bathroom complete with a jacuzzi tub, separate shower stall, and private water closet. Bedrooms two and three are located on the opposite side of the home and share a spacious hall bath with dual sinks and a tub/shower combination with direct access to the lanai — already perfectly set up for adding a future pool. The 4th bedroom is conveniently located near the kitchen and offers ensuite access to the 3rd full bathroom, making it an ideal setup for guests, extended family, or a private home office. Step outside and enjoy the impressive 10x40 screened lanai overlooking the spacious backyard and peaceful pond view. Part of the lanai is covered, creating the perfect relaxing space, while the screened area offers an ideal setup for grilling and enjoying beautiful evening sunsets. Additional updates and features include: • Replumbed in 2023 • New toilets in 2023 • Interior painted with Sherwin-Williams Super Paint • Roof replaced in 2015 • Water heater replaced in 2017 • Sprinkler system • Intercom system • 1-year home buyer’s warranty included for added peace of mind. Corrugated metal storm panels included with the home. Equip with flood lights on all 4 corners. Low HOA fees of only $220 semiannually and NO CDD. Conveniently located near Osceola Hospital, Downtown Kissimmee, and the Florida's Turnpike. Ready to call this your new home? Call today to schedule your private showing!

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

Listing Agent: Janet Mcquagge (407-927-7399)