Homes for Sale Near Osceola High School in Kissimmee - 142 homes

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: 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: Welcome to 2518 Empress Drive, a fully upgraded, luxury-inspired residence located within the highly desirable gated community of Tapestry in Kissimmee. Built in 2020 and extensively enhanced with high-end finishes and custom outdoor living upgrades, this exceptional 4-bedroom, 2.5-bath home delivers the lifestyle, design, and presentation typically associated with significantly higher-priced properties. Positioned on a premium corner lot, the home immediately impresses with its modern elevation, expansive paver driveway, and oversized 3-car garage. Inside, the open-concept layout showcases elevated contemporary finishes, oversized tile flooring, upgraded lighting, designer accent walls, and expansive living spaces thoughtfully designed for both everyday comfort and upscale entertaining. The true showpiece of the property is the spectacular resort-style backyard, representing approximately $200,000 in custom improvements and curated outdoor enhancements. Designed to rival luxury vacation retreats, the outdoor living experience features a heated saltwater pool with modern architectural lines, premium hardscaping, artificial turf accents, custom lounge areas, covered lanai, pergola, summer kitchen, wood-paneled ceiling detail, integrated entertainment space, and multiple gathering areas designed for seamless indoor-outdoor living year-round. The gourmet kitchen overlooks the main living and outdoor entertaining areas, creating an ideal setting for hosting guests while maintaining functionality and flow. Upstairs, the spacious primary suite offers a private retreat complete with a beautifully upgraded bathroom and oversized custom walk-in closet. Additional bedrooms provide flexibility for family, guests, office space, or lifestyle needs. Every detail of this home has been thoughtfully designed to create a polished, move-in-ready experience that blends modern elegance with resort-style comfort. Residents of Tapestry enjoy access to resort-inspired community amenities including a clubhouse, fitness center, community pool, parks, and recreational areas, all conveniently located near premier shopping, dining, major highways, and Central Florida attractions. This is a rare opportunity to own a highly upgraded, entertainer-focused home offering luxury presentation, exceptional outdoor living, and turnkey sophistication without the million-dollar price tag. Schedule your private showing today via Showingtime.

Listing is courtesy of: CENTURY 21 BE3 (727-596-1811)

Listing Agent: Tom Vitale (407-922-9934)

Remarks: Virtually Staged. Welcome to 3463 Forest Ridge Ln, located in the quiet gated community of Crestwood. This spacious 4-bedroom, 3.5-bath home with a 3-car garage offers over 3,800 square feet of thoughtfully designed living space, combining comfort, privacy, and an unbeatable Central Florida location close to shopping, dining, schools, and world-famous attractions. Designed for comfortable everyday living and entertaining, the home features expansive living spaces, a large kitchen with rich wood cabinetry, center island, pantry, breakfast nook, and a light-filled family room. The screened pool area provides the perfect private retreat for enjoying the Florida lifestyle year-round. The functional floor plan includes a designated office/den on the first floor, a convenient downstairs guest bedroom with its own en suite bath, generous living and dining areas, and a spacious primary suite featuring dual walk-in closets, double vanities, and a garden tub. The home is also ideally positioned near the community playground and pool area, offering convenient access to neighborhood amenities. major improvements provide peace of mind, including a new roof installed in 2021, two HVAC systems installed less than three years ago, a fairly new water heater and pool pump. Conveniently located near The Loop, Walt Disney World Resort, SeaWorld Orlando, Universal Orlando Resort, and Orlando International Airport, this home combines convenience, comfort, and value in one exceptional opportunity.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: Welcome home to this beautifully designed, low maintenance townhouse that perfectly balances style and convenience. 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. Do not miss the opportunity, SCHEDULE YOUR VISIT TODAY!!!

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

Listing Agent: Alexandra Cana (407-364-3578)

Remarks: Under contract-accepting backup offers. Welcome to the beautifully decorated Gardenia Floor plan, a designed 3-bedroom, 2-bath single-family home offering 1,706 square feet of thoughtful living space in the highly sought-after, guard-gated Tapestry community in Kissimmee. This isn’t just a home it’s a lifestyle. Step inside to an open, airy layout perfect for modern living. From cozy family nights to weekend entertaining, every square foot is optimized for comfort and flow. With three spacious bedrooms and sleek, contemporary finishes, the Gardenia model is the ideal blend of function and flair. Live like you're on vacation every day with access to a Zero-entry resort-style pool & cabana lounges, Splash pad & play spaces, State-of-the-art fitness center with yoga & movement studio, a Grand ballroom & catering kitchen for hosting unforgettable events, an Open-air veranda for sunset relaxation. Lots of Sports fields, BBQ pavilions, dog park, and walking and biking trails. And it’s all nestled in a 24-hour guard-gated community, minutes from Orlando's top attractions, major highways, the airport, shopping, dining, and great schools. Whether you’re looking for your primary residence, second home, or investment opportunity, this Gardenia beauty is your gateway to elevated living in Central Florida. Homes like this don’t just go on the market they go viral. Schedule your private tour before it’s gone!

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

Listing Agent: Gladys Bezerra (407-701-4034)

Remarks: Two stories, two bedrooms, two and a half baths, with the boring expensive stuff already handled. NEW roof overhead, NEW AC, NEW hot water heater, special assessment already paid, NEW living room flooring downstairs, NEW carpet up, and FRESH paint throughout. The first floor opens into a foyer that gives way to a full dining room on one side and a kitchen with breakfast bar seating on the other, both flanking a living room that stretches to back sliders. A second set of sliders off the front leads to a private patio, so you get cross-breeze and two outdoor spots before you even head upstairs. A half bath sits tucked off the kitchen for guests. Upstairs holds two true primary suites, each with its own full bathroom and its own private balcony. One faces the front, one faces the back, both have walk-in closets, and the laundry closet lives upstairs where the laundry actually is. Windsor Pines comes with a community pool and a playground, and the location does the rest of the work. You're a few minutes from The Loop, where the grocery run, the dinner reservation, and the movie all happen in one parking lot. Ten minutes to downtown Kissimmee and the lakefront, straight onto Osceola Parkway or the Turnpike when you need to be elsewhere, and about fifteen minutes from the Disney gates when you don't. Two primaries. Two porches. Two private balconies. One opportunity.

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

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

Remarks: Welcome to this exceptional former builder model home in the desirable Avilla community. This beautifully maintained 4-bedroom, 3-bath residence offers 3,410 heated square feet of thoughtfully designed living space on a spacious 0.21-acre homesite. The open floor plan features a gourmet kitchen with granite countertops, stainless steel appliances, custom cabinetry, and a large center island. The luxurious primary suite includes a spa-like bath and an oversized custom walk-in closet. Enjoy Florida living at its finest with a private screened pool, expansive pool deck, and fully equipped outdoor summer kitchen, perfect for entertaining. Originally purchased as the builder's final model home, the property showcases premium upgrades and exceptional craftsmanship throughout. Seller intends to convey the property substantially furnished, excluding personal belongings and décor. Conveniently located near shopping, dining, major highways, and Orlando's world-famous attractions. Schedule your private showing today!

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

Listing Agent: Elias Pedro Vieira Manna (407-201-2693)

Remarks: Dream townhome alert! This gorgeous 4BR/3BA (including 2 ensuites) unit in San Vitorino Cir, Kissimmee offers 1,470 sq ft of bright, open living space perfect for entertaining and relaxing. With a recently remodeled owner's suite and a recently replaced AC unit and boiler. Enjoy your morning coffee on the small patio / varanda, and experience the comfort of move-in ready Florida living. The community features 3 sparkling pools, a full clubhouse, and plenty of amenities for fun and fitness. Prime location near highways, shopping, dining, and schools— don’t wait, your new home awaits!

Listing is courtesy of: DEBRASSI REALTY LLC (407-446-1343)

Listing Agent: Marcela Andrade Drummond (407-752-2323)

Remarks: Welcome to Regal Cove – Modern Luxury Meets Country Charm! Imagine living in the exclusive, gated community of Regal Cove, where this fully renovated custom home offers both elegance and privacy. Set on nearly half an acre (.49), this residence boasts one of the largest private screened lap pools in the area with a heated spa—perfect for entertaining or relaxing year-round. From the moment you arrive, the long driveway and welcoming front porch set the tone for comfort and sophistication. Step inside the brand-new modern renovation featuring an open concept design and tasteful finishes throughout. The spacious family room is highlighted by an elegant tile accent wall with an electric fireplace and French doors overlooking the pool and mature tree views. The gourmet kitchen is a showpiece with a waterfall island, drop-down range system, top-tier appliances, custom cabinetry, built-in double oven/microwave, wine cooler, and coffee station. A true chef’s delight, it’s designed for hosting family and friends with ease. The primary suite, located on the first floor, offers a stunning walk-in closet and a spa-like bathroom with a freestanding soaking tub, double vanities, separate water closet, and an oversized double-head shower. Upstairs, you’ll find four additional bedrooms with a sleek glass panel railing system, a bonus storage room, and two beautifully renovated Jack & Jill bathrooms. Adding incredible flexibility, a three-car garage with extended roofline includes a private full apartment above the garage with a bedroom, bathroom, kitchen, and living/dining area. Perfect as a guest house, or secondary suite. Outdoor living shines with two covered patio areas, French impact windows, and the expansive screened pool deck. With only $400/Quarter HOA fees, Regal Cove provides an upscale yet affordable lifestyle, ideally located near Lake Tohopekaliga with a public boat ramp less than a minute away. You’ll also enjoy easy access to the FL Turnpike, Publix, Walmart, and all of Kissimmee’s conveniences. This is a rare opportunity to own a modern, custom-renovated pool home with an in-law suite in one of Kissimmee’s most desirable gated communities. Schedule your private showing today and experience the perfect blend of country charm and modern luxury.

Listing is courtesy of: FIERCE REALTY (407-758-5179)

Listing Agent: Rachel Coolidge (207-522-0838)

Remarks: Welcome to the beautiful community of Adriane Park. With large lots and only 54 homes, they just don't make neighborhoods like this one any more. This home sits on over 1/3 of an acre and overlooks the beautiful pond with a fountain. The home itself is absolutely gorgeous, with exquisite curb appeal with brick overlays and hardy board siding. The roof was replaced in December of 2024. The main living and dining area have hardwood floors and there is crown moulding throughout the downstairs. The living room has a wood burning fireplace. The kitchen has ceramic tile, stainless steel appliances and Schrock handcrafted pecan wood cabinetry. The primary bedroom is downstairs with it's own private bathroom, as well as another half bathroom downstairs. Indoor laundry is located downstairs next to the half bath. Upstairs there are 4 more spacious bedrooms, all with walk-in closets! The fifth bedroom has double doors and dual walk-in closets and can be used as a flex space, or upstairs living area. The Florida Room is huge with ceramic tile and is air conditioned through the main unit and also offers a mini split HVAC unit. It leads out to the beautiful screened in pool area that is perfect for entertaining, with landscaping and an electric above ground hot tub. The pool overlooks the neighborhood pond, which also means no rear neighbors. This home is ready to be the focal point of all of your family gatherings!

Listing is courtesy of: ALL STAR PROPERTIES OF CENTRAL (407-846-9100)

Listing Agent: Kevin Waldbieser (407-460-7993)

Remarks: Welcome to this well-maintained 3-bedroom, 2-bathroom home offering the perfect blend of comfort, functionality, and location. Inside, you’ll find multiple living spaces including a formal living room, dining room, and a spacious family room—ideal for both everyday living and entertaining. The kitchen flows seamlessly into the main living areas, creating a warm and inviting atmosphere. The primary suite features a large bathroom complete with a soaking tub and separate walk-in shower, providing a relaxing retreat. Step outside to your private backyard oasis with a screened-in pool and fully fenced PVC yard—perfect for enjoying Florida living year-round. Additional updates include a newer AC system installed in 2023 for added peace of mind. Located in the desirable Cranes Cove community, residents enjoy low HOA fees and access to a community pool. Just minutes from The Loop shopping center, you’ll have convenient access to restaurants, movie theaters, shopping, and more. Plus, you’re a short drive to Disney and all that Central Florida has to offer. Whether you’re looking for a primary residence, investment property, or vacation home, this one truly checks all the boxes.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Dominick Florio (321-377-4045)

Remarks: CHARMING DOWNTOWN KISSIMMEE HOME WITH MODERN UPDATES,FRESH INTERIOR PAINT & CLASSIC CURB APPEAL WELCOME TO THIS BEAUTIFULLY MAINTAINED 3-BEDROOM, 2-BATHROOM HOME IDEALLY LOCATED IN THE HEART OF DOWNTOWN KISSIMMEE, JUST MINUTES FROM SHOPPING, RESTAURANTS, AND PUBLIC TRANSPORTATION. INSIDE, YOU’LL FIND A SPACIOUS GREAT ROOM, WELL APPOINTED KITCHEN AND BATHROOMS. OFFERING MODERN COMFORT WITH TIMELESS STYLE. THE LARGE KITCHEN AND DINETTE AREA ARE PERFECT FOR EVERYDAY LIVING AND ENTERTAINING, COMPLETE WITH A LARGE PANTRY AND A CONVENIENT INSIDE LAUNDRY ROOM. STEP OUTSIDE AND ENJOY THE HOME’S CLASSIC CHARM WITH A COVERED FRONT PORCH WITH RAILING OVERLOOKS A LOVELY PICKET FENCE, CREATING A WARM AND WELCOMING FIRST IMPRESSION. ADDITIONAL FEATURES INCLUDE A 2-CAR CARPORT AND A 10X12 STORAGE SHED WITH ELECTRIC, IDEAL FOR TOOLS, HOBBIES, OR EXTRA STORAGE. MAJOR UPDATES INCLUDE A BRAND-NEW ROOF (2025), GIVING PEACE OF MIND TO THE NEXT OWNER. THIS MOVE-IN-READY HOME BLENDS LOCATION, SPACE, AND CHARACTER. WHAT AN EXCELLENT OPPORTUNITY TO OWN A WELL MAINTAINED PROPERTY RIGHT IN DOWNTOWN KISSIMMEE.

Listing is courtesy of: GOODWIN REALTY & ASSOCIATES, INC (407-846-2787)

Listing Agent: Linda Goodwin-Nichols (407-908-0320)

Remarks: Welcome to this beautifully updated home on a desirable corner lot in the heart of Kissimmee! From the moment you arrive, you’ll notice the fresh exterior paint, inviting curb appeal, and pride of ownership throughout. Step inside to discover a bright and spacious layout featuring a stunning updated kitchen designed to impress, complete with gorgeous quartz countertops, modern finishes, and the perfect setup for both everyday living and entertaining. The open flow of the home creates a warm and welcoming atmosphere ideal for gathering with family and friends. The primary suite offers a refreshed vanity area with stylish updates, creating a relaxing private retreat. Outside, the corner lot provides added space, privacy, and curb appeal that’s hard to find. Located in an incredibly convenient and highly sought-after Kissimmee location, you’re just minutes from The Loop, shopping, dining, Orlando International Airport, major highways, theme parks, Lake Nona, and all that Central Florida has to offer. Whether you’re looking for a primary residence or a vacation home, this move-in-ready property offers the perfect combination of location, updates, and value. Homes with upgrades like this in such a prime location do not last - schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Patrizia Harrington (908-329-0392)

Remarks: Discover comfort, convenience, and versatility in this 3-bedroom, 2-bath home, with fresh paint inside and out. Ideally located just minutes from The Loop’s shopping, dining, and entertainment, as well as schools and public transportation. The functional floor plan features updated kitchen, solid-surface countertops, tile and carpet flooring, and a second kitchen that offers excellent potential for multi-generational living, extended family, guests, or a private in-law suite. Enjoy the benefits of solar panels for improved energy efficiency and potential utility savings. Outside, the large fenced backyard provides plenty of room for pets, play, gardening, or entertaining. Unwind on the covered, screened porch, and take advantage of the storage shed for additional storage and organization. Combining a convenient location, flexible living options, and valuable updates, this home is ready for its next owner to move in and make it their own.

Listing is courtesy of: CENTRAL FLORIDA REAL ESTATE PROS (407-873-0651)

Listing Agent: Bethany Rudy (407-873-4231)

Remarks: SELLER OFFERING UP TO $5,000.00 TOWARD BUYER'S CLOSING COSTS. Welcome to 3005 Slough Creek Dr – a beautifully designed, move-in-ready home built in 2022 and thoughtfully updated for modern living. Boasting over 2,700 sq ft, this flexible floor plan features 4 bedrooms, 3 bathrooms, plus a loft and flex room—ideal for a home office, gym, or 5th bedroom conversion with an additional office downstairs. Inside, you'll love the fresh designer touches including new kitchen hardware (2024) and modern light fixtures (2023) that elevate the home’s bright and open layout. Durable tile flooring in main areas complements the contemporary design, while plush carpet adds comfort to bedrooms and upstairs spaces. The kitchen opens to the living and dining areas, making it perfect for entertaining. Step outside to a lake view backyard where new gutters (2023) provide long-term protection and curb appeal. Located in a growing, family-friendly community near schools, shopping, major highways, and Central Florida attractions, this home offers both convenience and comfort in a prime Kissimmee location. Don’t miss your chance to own this nearly new, upgraded home—schedule your showing today!

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

Listing Agent: Devin Panlaque (407-421-2118)

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: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Located on a quiet street in the heart of Kissimmee, 1903 Brown Street offers a versatile layout and inviting outdoor spaces designed for modern Florida living. This 4-bedroom, 2-bath home features 1,892 heated square feet and an open-concept floor plan that allows the main living areas to flow naturally—ideal for both everyday living and entertaining. In addition to the primary living space, the home includes an oversized garage, a dedicated gym area, and a separate man cave or second living room, providing flexibility for fitness, hobbies, or additional entertaining space. These bonus areas make the home especially well-suited for work-from-home lifestyles, multi-generational living, or those seeking extra functional square footage beyond the bedrooms. Step outside to a private, fully fenced backyard featuring a screened-in pool, perfect for year-round enjoyment, along with a storage shed for added convenience. Centrally located just minutes from shopping, dining, schools, and major roadways, this home offers easy access to Orlando attractions, theme parks, and commuter routes.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Thomas Nickley, Jr (407-629-4420)

Remarks: Charming 2-bedroom, 1.5-bath condo perfect for a first-time homebuyer, starter home, or investment opportunity. This inviting home features an updated kitchen with granite countertops, bright white cabinetry, and mix stainless steel appliances, offering a clean and functional space that opens to the main living area. The first floor features tile flooring throughout the living and dining areas, while both bedrooms are privately located upstairs with carpet flooring for added comfort. Enjoy relaxing outdoors on the spacious screened-in porch with a private rear view. Additional highlights include a 1-car garage and a location just steps from the community pool and clubhouse, making it easy to enjoy the neighborhood amenities. Great investment potential with rental rates in the area available. Conveniently located near shopping, dining, and major roadways.

Listing is courtesy of: HELLO SUNSHINE REALTY LLC (407-719-8932)

Listing Agent: Marissa Mcclung (407-719-8932)

Remarks: Price Improvement! Charming 3-bedroom, 2-bathroom single-story home in the highly desirable Kissimmee area with NO HOA! Situated on an large lot, this property offers flexible space for entertaining and relaxing. You'll love the great curb appeal from the fresh exterior paint, while the inside features a bright, welcoming atmosphere with abundant natural light. The kitchen comes fully equipped with all appliances. ROOF 2018, A/C 2018. Perfectly located near local schools, shopping, dining, and major roadways, this home combines comfort, location, and incredible value. Whether you are a first-time buyer, looking to downsize, or seeking a prime investment opportunity, this property is full of possibilities, Schedule your showing Today!

Listing is courtesy of: LIV REALTY II INC. (407-574-4404)

Listing Agent: Linda Guzman (407-574-4404)