Homes for Sale Near Osceola High School in Kissimmee - 108 homes

Remarks: Charming and beautifully positioned 3 bedrooms, 2 bathrooms ground floor unit with peaceful garden view and resort style living at your doorstep. Just steps away from the sparkling community pool and gazebo, this home offers the perfect blend of comfort and convenience. Enjoy a bright, open layout filled with lots of light, a cozy back patio ideal for relaxing mornings, entertaining or unwinding evenings. A well kept home, with a lot of upgrades and all stainless steel appliances. Nestled in a prime location close to shopping, dining and major roadways. This is an exceptional opportunity for homeowners or investors seeking the Florida lifestyle at its best.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Claudette Banton Dennis (347-876-1091)

Remarks: 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. 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 beautifully maintained 4-bedroom, 2-bathroom pool home perfectly situated on a scenic pond in a gated community. This immaculately cared-for residence offers the ideal blend of comfort, privacy, and Florida lifestyle living. Relax or entertain in your private pool overlooking tranquil water views, creating the perfect backyard retreat. The home features a spacious and functional layout, ideal for both everyday living and hosting family and friends. Pride of ownership is evident throughout, making this home truly move-in ready. Conveniently located in a central location close to shopping, dining, and major roadways, with easy access to Orlando’s world-famous theme parks and Orlando International Airport, making travel and entertainment just minutes away. This exceptional home offers the perfect combination of location, lifestyle, and meticulous maintenance.

Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P (407-730-8737)

Listing Agent: Edwin Gonzalez (321-402-2284)

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 (407-319-4113)

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: Great price on this beautifully renovated home, updated just three years ago! A proven, well-maintained rental with excellent income potential, this solid block 3-bedroom, 1-bath home offers side-yard parking behind fencing plus EV (electric vehicle) hookups. Renovated throughout, the home features all 3-year old appliances, ceramic tile flooring, a fully updated kitchen with 42” soft-close cabinets and stunning quartz countertops, recessed lighting, ceiling fans, tankless water heater, updated plumbing and electrical, 5/8” drywall, doors, paint, and updated ductwork. A/C (2017) and maintained. Enjoy outdoor living with a large covered back porch overlooking a refinished in-ground pool (2019), outdoor shower, RV concrete pad with electric, water, and security lighting, and a roof with solar attic vent. Additional upgrades include hurricane-certified double-pane vinyl windows. Ideally located near downtown Kissimmee, close to Osceola Parkway for shopping, schools, parks, major attractions, and easy access to both East and West Coast beaches. Move-in ready and investment-friendly—this one won’t last!

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

Listing Agent: Brandy Dileonardo (407-460-2107)

Remarks: Experience the epitome of resort-style living in this meticulously maintained 2-bedroom, 2-bathroom villa located within the exclusive gated community of Sterling Park at Stonefield. The interior radiates modern elegance with soaring ceilings, crown molding, and premium porcelain tile flooring throughout a bright, open-concept layout. At the heart of the home, the chef-inspired kitchen shines with crisp white cabinetry, granite countertops, and stainless steel appliances, seamlessly flowing into a sun-drenched dining area. Retreat to the spacious primary suite, complete with custom shutters and a spa-like ensuite featuring a dual vanity and a frameless glass walk-in shower. Beyond the glass sliders, your private screened-in lanai offers peaceful, unobstructed views of the community’s lush greenspace—perfect for quiet Florida mornings. With the HOA handling lawn and exterior maintenance, you’re free to enjoy the resort-style pool, fitness center, and tennis courts, all while being minutes away from world-class shopping at The Loop and major Orlando attractions.

Listing is courtesy of: MILESTONE FAMILY REALTY LLC (689-265-3683)

Listing Agent: Jeff Joachim (689-304-9330)

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: Discover your own private retreat in the heart of Poinciana! This beautifully maintained 3-bedroom, 2-bath pool home with a brand-new roof and floor offers nearly 1,900 sq. ft. of comfortable living space on a generous 0.21-acre lot. Inside, you’ll find an inviting open floor plan, tile flooring throughout, a bright kitchen with abundant cabinetry, and a spacious living area ideal for entertaining. The split bedroom layout provides excellent privacy, while the screened-in pool and outdoor deck give you a peaceful setting for both relaxation and gatherings. Additional highlights include a detached 2-car garage, a fully chain-link fenced backyard, and no CDD fees. Nestled on a quiet cul-de-sac with desirable north-facing frontage, this home is just minutes from schools, parks, and shopping. Located within the Association of Poinciana Villages, the community features a low monthly HOA. Don’t miss this move-in-ready home with incredible potential—schedule your showing today!

Listing is courtesy of: LAND & HOME ASSET LLC (407-417-1629)

Listing Agent: Amy Rivers (407-417-1629)

Remarks: Step Into Style & Serenity: A Mid-Century Modern Gem in the Heart of Neptune Corridor Welcome to your private retreat—where timeless mid-century modern design meets the comfort of contemporary luxury. From the moment you enter, this beautifully appointed home envelops you in warmth, elegance, and thoughtful design. Original oak hardwood floors greet you with a rich, organic texture, while the open-concept layout creates a sense of spaciousness far beyond its square footage. The chef-inspired kitchen is a true showstopper, boasting sleek granite countertops, premium cabinetry, a gas range, and a full suite of stainless-steel appliances. Every detail has been considered—from the modern designer lighting that highlights architectural features and original built-ins, to the seamless flow between living, dining, and entertaining spaces. Your primary suite is a sanctuary unto itself. Unwind in the newly renovated, spa-inspired bathroom featuring an oversized walk-in shower, deep soaking tub, and luxe finishes that evoke five-star resort living. French doors open from the bedroom onto your private 10x12 deck—complete with a retractable awning—perfect for sipping morning coffee or winding down with a sunset glass of wine. The secondary bedroom is equally inviting, complemented by a fully remodeled guest bathroom that’s sure to impress visitors. Whether hosting overnight guests or simply enjoying everyday life, this home is designed for comfort and impact. Step outside to an expansive, screened-in back patio ideal for weekend barbecues, family gatherings, or tranquil evenings under the stars. Beyond the patio, an oversized driveway offers ample room for extra vehicles, RVs, or boats, complete with a 30-amp outlet—ready for your next adventure. Situated just a short stroll from Lakefront Park and the vibrant shops and restaurants downtown, you’ll enjoy the rare blend of peaceful retreat and walkable convenience. With easy access to major highways, public transportation, Neo City, and the dynamic Neptune corridor, you’re perfectly positioned for both work and play. Range can work on Electric or Gas propane. Come home to modern comfort, classic charm, and a lifestyle that feels like a permanent getaway. Seller motivated to work on the transaction.The seller contributes toward the buyer's closing costs.

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

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

Remarks: 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: BEAUTIFUL HOME WITH POOL -- LOCATED IN THE MIDDLE OF KISSIMMEE -IN VERY CLOSE DISTANCE OF MAIN ROADS, RESTAURANTS , BANKS , TOURISTIC AREAS --***NO HOMEOWNERS ASSOCIATION *** BRING YOUR BOATS AND YOUR RV'S , YOUR POOL HOME IS WAITING FOR YOU . THIS PROPERTY ALSO FEATURES 3 BEDROOMS AND 2 BATHS, AND 1 BEDROOM 1 BATH AL LADO CON ENTRADA SEPARADA COMO CASA DE LOS SUEGROS O DE VISITA --COME AND SEE IT AS SOON AS POSSIBLE !!!

Listing is courtesy of: ZEA REALTY & ASSOCIATES (407-931-6511)

Listing Agent: Consuelo Zea (407-931-6511)

Remarks: Welcome to this spacious and versatile 3-bedroom, 2-bathroom pool home located in a desirable gated community. Designed with a thoughtful split floor plan, this home offers privacy and comfort for the whole family. At the front of the home, you’ll find a bright and airy living room and dining room combo—perfect for entertaining or relaxing. The heart of the home features an open kitchen with a cozy breakfast area that flows seamlessly into the family room, creating a warm and inviting space for everyday living. An additional bonus room just off the family room offers endless possibilities—ideal for a home office, playroom, or personal gym. You'll also appreciate the convenience of an inside laundry room. Step outside to your private backyard oasis with a sparkling pool, perfect for enjoying Florida’s sunny days. Located just minutes from Kissimmee Lakefront Park, shopping, sports venues, restaurants, and world-famous theme parks, this home combines comfort, convenience, and fun in one fantastic package. Don't miss your chance to own this beautiful home in a prime Central Florida location! Roof (2018) HVAC (2022)

Listing is courtesy of: KEYSEEKERS REAL ESTATE (727-490-9000)

Listing Agent: Julie Glass (321-436-6881)

Remarks: BEAUTIFUL AND IMPECCABLE GEM. Welcome to your own piece of paradise here in sunny Florida. This 4-bedroom, 2.5-bathroom home is perfect for your family. Offering endless luxuries throughout the home, upon opening the front door, to your right, you will find an office/study with tons of natural light streaming in. Adjacent to the office/study is the formal dining room, where you can set a long table for your entire family. The whole first floor has Italian porcelain tile floors. The beautiful kitchen features spectacular granite countertops, elegant cabinetry, and high-end stainless steel appliances, providing a spacious and comfortable living area to share with friends and family. The entire home has fine Persilux aluminum blinds. With a large backyard already protected almost entirely with fencing for added security, you will have plenty of space to host gatherings with friends or family. All bedrooms are on the second floor, and the staircase and living room floors are made of brown wood, making it very elegant. The master bedroom has two large, comfortable closets. The master bathroom has a double vanity, a shower, and a garden tub. The home also has a cozy porch where you can enjoy coffee while watching the beautiful Florida sunrise or sunset. The home is located in the beautiful and secure Tapestry community, where you'll enjoy a family-friendly atmosphere. Amenities include 24/7 security, swimming pools, playgrounds, cabanas, and a fitness center. It's also very close to the Loop Mall, where you'll find a wide variety of restaurants and shops, and just 20 minutes from Disney. Don't miss out on this beautiful home for your family!

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

Listing Agent: Marilin Lugo (407-285-6145)

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: Short Sale. FOR SALE - SHORT SALE - 4 Bedroom/ 2 Bath 2400 sq.ft. Single Family Home on a quiet street in the community of Poinciana. The home is spacious and offers an open floor plan. WI-FI is included in the HOA fees. The Living Room, Dining Room and Kitchen combo are ideal for entertaining. The kitchen has an island which is perfect for serving food or sitting around to eat a snack. The range, range hood, and dishwasher come with the home. The Primary Bedroom is generously sized with a well-equipped Primary Bathroom. The home features several storage closets and an inside laundry room. The home comes with solar panels and an unfinished pool. Poinciana is located on the outskirts of Kissimmee and Orlando and provides many activities for today's family. The Poinciana Community Park has playgrounds, picnic tables, sports fields and offers seasonal festivities and outdoor movie nights. The Poinciana Library offers reading programs, story time for minors, workshops for the adults, and events for all ages. For nature lovers, Poinciana is home to the Disney Wilderness Preserve which is a 12,000 acre preserve with hiking trails and areas to see Florida's native birds and flowers. Let's not forget this home is only a half hour from DISNEYWORLD!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Linda Andre (863-852-5747)

Remarks: Welcome to 2517 Interlock Dr, Kissimmee, FL! This beautifully maintained single-family home offers the perfect blend of comfort and convenience in a prime location near all that Central Florida has to showcase. Featuring 4 bedrooms and 2.5 bathrooms with a downstair office space, this residence boasts an open-concept floor plan filled with natural light, making it ideal for both everyday living and entertaining. The spacious kitchen includes modern appliances, ample cabinetry, and a breakfast bar that flows seamlessly into the dining and living areas. Step outside to enjoy a screened-in private pool—perfect for relaxing or hosting family gatherings. Additional highlights include a 2-car garage, primary suite with walk-in closet. Conveniently located just minutes from shopping, dining, schools, and world-famous attractions, this home offers both comfort and accessibility. If you’re looking for a primary residence, 2517 Interlock Dr is an opportunity you won’t want to miss. Schedule a showing today!

Listing is courtesy of: JWJ REALTY LLC (407-808-8899)

Listing Agent: Pan Pan (321-948-6723)

Remarks: One or more photo(s) has been virtually staged. Beautifully maintained 4-bedroom home in desirable Heron’s Landing, ideally located near Loop West in the City of Kissimmee, on the border of Osceola and Orange County. This spacious single-story residence offers 2,059 square feet with a popular split floor plan and open, airy layout. Recent upgrades include fresh interior and exterior paint (2026) and new vinyl flooring (2025), newer roof (2018) and newer HVAC (2017). A formal living and dining area welcomes you at the foyer. The updated kitchen is ideal for cooking and entertaining, featuring ample counter space and newer appliances. The kitchen and breakfast nook open to a spacious family room with high ceilings, creating an inviting setting for gatherings. Both the sliding glass doors and breakfast nook french doors extend your living space to a gorgeous screened-in lanai, perfect for relaxing or entertaining. The primary suite overlooks a large backyard with lush fruit trees and features private lanai access. The en-suite bathroom offers a garden tub, separate shower, dual-sink vanity, and an oversized walk-in closet. Three additional bedrooms provide generous closet space, excellent natural light, and share a full bathroom. Additional highlights include newer laminate flooring in main living areas (no carpet at all), an indoor laundry room with extra storage, a 2-car garage with attic access, professionally cleaned HVAC system and whole-house ducts (2025), home security system, and irrigation system. Heron’s Landing is part of a well-maintained Eagles Reserve community, offering low HOA fees and amenities such as a community pool, playground, park areas, and fitness trails. Enjoy the convenience of being very close to The Loop, a sprawling outdoor mall with department stores, specialty shops, and casual dining. Close to Disney attractions, hospitals, Florida Turnpike, and SR-417. Move-in ready with major updates (see attached lists) —don’t miss this exceptional opportunity!

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Sherry Wang (484-744-4586)

Remarks: Some homes have a floor plan. This one has a strategy. Tucked at the end of a quiet cul-de-sac shared with just one other home, 1980 Summer Ct sits on over half an acre and does something most single-family homes simply can't — it functions as two completely independent living spaces under one roof. Two kitchens. Two laundry rooms. Two two-car garages. Three full baths. And a paid-off solar system keeping your electric bill in check from day one. Here's how it actually lives: you walk in through a generous shared living room — the natural gathering point — and then the home splits. The right side offers two bedrooms, two full baths, a full kitchen, its own family room, and direct access to an oversized screened-in lanai overlooking a huge, fully fenced backyard. The left side features a spacious primary suite with a full ensuite, its own family room, a complete second kitchen with pantry, and its own attached two-car garage. The other garage sits on the right side. Each side, its own space. Each space, fully equipped. Whether you're housing two generations under one roof without sacrificing anyone's privacy, living on one side while offsetting your mortgage with the other, or simply running a household that needs serious flexibility — this layout delivers in a way that almost nothing on the market can match. No HOA means no restrictions and no extra fees. The location pulls its own weight too. You're minutes from East Lake Toho, one of Central Florida's best bass fishing lakes, Kissimmee Lakefront Park, and the outdoor adventures of Shingle Creek Regional Park. Downtown Kissimmee and St. Cloud are close for dining, shopping, and entertainment. And Walt Disney World, Universal, and the rest of the theme park corridor are an easy drive — close enough to enjoy, far enough to escape. Opportunities like this don't come along often. When they do, they move fast.

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

Listing Agent: Shawn Layton (321-514-8055)

Remarks: This 1-bedroom, 1-bathroom condo is in excellent condition and features, perfect for relaxing at home. The open layout and well-kept interiors make it move-in ready and easy to personalize. The kitchen includes appliances in perfect condition. Located in a convenient area of Kissimmee, you’re just minutes from schools, shopping centers, restaurants, hospitals, pharmacies, banks, and local stores. The community is well-organized and professionally managed, keeping common areas maintained and ensuring a smooth living experience. This condo offers the perfect combination of comfort, convenience, and practicality—ideal for anyone looking for a move-in ready home in a great location. An appointment must be scheduled at least 24 hours in advance. There is an administrative fee payable to the association that the new owner must pay ($750). The HOA fee includes sewer, trash, and pest control.

Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)

Listing Agent: Marianna Spinelli (786-447-1655)