Homes for Sale Near Osceola High School in Kissimmee - 63 homes

Remarks: One or more photo(s) has been virtually staged. Positioned on an expansive 0.45-acre lot with no HOA in Kissimmee, this custom-built residence delivers space, privacy, and elevated finishes rarely found at this price point. Inside, the architecture is clean and intentional, highlighted by soaring ceilings, crown molding, and a seamless open layout designed for both everyday living and entertaining. At the center of the home is a fully upgraded chef’s kitchen, featuring premium granite countertops, custom cabinetry, and high-end built-in appliances including a double oven and integrated refrigerator, complemented by a functional butler’s pantry for added storage and prep space. The main living areas flow effortlessly, creating a bright and inviting environment with strong indoor-outdoor connectivity. The first-floor primary suite is designed for privacy and scale, offering a spacious layout, large walk-in closet, and a well-appointed bath with a soaking tub, oversized shower, and dual vanities. A dedicated front flex space provides versatility as a home office, study, or additional living area. Upstairs, three additional bedrooms are thoughtfully positioned along with two full bathrooms, including an en-suite located on the second floor, offering flexibility for multi-generational living or guest accommodations. The outdoor space is equally impressive, anchored by a large screened-in patio with elevated ceilings, ideal for year-round use. Beyond, the oversized backyard offers ample room to design a custom pool or outdoor retreat, all without the restrictions of an HOA. Located in a highly accessible area of Kissimmee, this home is just minutes from major roadways including the Florida Turnpike and 417, providing easy access to Lake Nona’s Medical City and NeoCity, a growing hub for technology and innovation. You’re approximately 25 minutes to Orlando International Airport, 30–35 minutes to Walt Disney World and major attractions, and about 20–25 minutes to Downtown Orlando. Everyday conveniences are close by with Publix, Walmart, The Loop shopping center, restaurants, and schools all within a short drive. For weekend getaways, Florida’s east coast beaches are roughly 60–75 minutes away. **UPGRADES LIST AVAILABLE UPON REQUEST**

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Veronica Figueroa (407-519-3980)

Remarks: WOW! Highly Convenient First-Floor Condo in Prime Kissimmee Location! This exclusive first-floor condominium offers a functional and well-designed layout, perfect for comfortable living or investment. Upon entry, you are welcomed by a bright and inviting living area featuring large windows that fill the space with natural light and open to a private balcony with peaceful green views, ideal for relaxing or enjoying outdoor dining. The fully equipped kitchen boasts stainless steal appliances, spacious cabinetry, Tile in the kitchen, Livingroom, and hardwood style tile flooring in the bedrooms, seamlessly blending style, and functionality “NO CARPET”. Every detail of this home has been thoughtfully designed to support a relaxed and comfortable lifestyle. Community amenities include private parking, 24-hour security, a clubhouse, and a resort-style swimming pool. Enjoy the convenience of an urban lifestyle while maintaining the tranquility of open views and well-maintained surroundings. Strategically located in the heart of Kissimmee, just minutes from US-192, with easy access to shopping, dining, entertainment, and transportation. A short drive to The Loop Mall and close to Central Florida’s best restaurants and attractions. This versatile property is ideal as a primary residence, second home, or investment opportunity. A must-see first-floor unit—schedule your private tour today!

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

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

Remarks: More pics come soon. 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: Full of old-school charm and lovingly maintained by the same family since new, this inviting 3-bedroom, 2-bath home offers comfort, character, and an unbeatable central location. From the moment you arrive, you’ll appreciate the pride of ownership and timeless appeal throughout. Inside, the home features a warm and welcoming layout highlighted by a cozy wood-burning fireplace—perfect for relaxing evenings. The functional floorplan includes an inside utility area for added convenience, while thoughtful updates such as a tankless water heater and an updated electrical breaker box provide peace of mind. Step outside to enjoy a fully fenced backyard, ideal for pets, play, or entertaining. The covered and screened back porch creates the perfect space to unwind year-round while enjoying the outdoors in comfort. A carport with additional storage above offers practical space for vehicles and extra belongings. Located just minutes from the hospital, downtown, Amtrak, the bus station, and SunRail, this home offers easy access to everything you need while maintaining a quiet, established neighborhood feel. A rare opportunity to own a well-cared-for home with character, updates, and a prime location—schedule your showing today!

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Bring your imagination!!!fixer upper in the best part of city of Kissimmee! Vintage home ready for that buyer that loves a bit of history. room. Great possibilities. Income producer $4,000 a month

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

Listing Agent: Paola Almonte (407-968-7511)

Remarks: Welcome to this beautifully located 3-bedroom, 2.5-bath condo in the desirable Villas of Estancia community in Kissimmee, FL. Perfectly situated across from the community pool, this home offers convenience and comfort in one of the area’s most accessible locations. Enjoy easy access to a wide variety of shopping, dining, and everyday essentials just minutes away. With a functional layout and spacious bedrooms, this condo is ideal as a primary residence, vacation home, or investment opportunity.

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

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

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: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This 4 bedroom, 2 bathroom home with 1,720 sq ft checks the boxes buyers are asking for, space, layout, location, and the ability to move in without the wait. Located in a small gated community, you will enjoy a peaceful water view and a layout that actually makes sense. The oversized living and dining area gives you flexibility for everyday living or hosting, with crown moulding and tile flooring throughout the main spaces. The bedrooms feature wood floors, and the home is clean, well-maintained, and ready for its next owner. That is where the value is. Additional features buyers love: • 2 car garage with epoxy floors • In-home washer and dryer included • Open, functional floor plan • Natural light throughout • Vacant for easy showings and quick closing Whether you want a primary residence you can personalize over time or a solid investment, this property offers a great combination of condition, location, and opportunity. Seller is motivated and ready to make a deal. Homes with this much space, in a gated community, with a water view, at this price point, do not last. Schedule your showing and see the potential for yourself.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Naomi Embleton (407-709-6020)

Remarks: Welcome to this spacious and inviting home, thoughtfully designed for comfortable family living and making lasting memories. Step inside to a bright, open-concept living and dining area—perfect for both entertaining guests and everyday relaxation. The kitchen is a true centerpiece, featuring brand-new appliances, a convenient breakfast bar, and a cozy eat-in space. It flows seamlessly into the family room, creating an ideal layout for staying connected with family and friends. Brand new HVAC (2026) Roof (July 2025). The generously sized primary suite offers a peaceful retreat, complete with a walk-in closet. Three additional bedrooms provide ample space and flexibility for family, guests, or even a home office. Enjoy added privacy with no rear neighbors, as the home backs up to a tranquil wooded area—perfect for relaxing or unwinding outdoors. Ideally located in the heart of Kissimmee, this home is just minutes from major highways, shopping centers, dining, and everyday conveniences. This home truly has it all and won’t last long—schedule your private showing today!

Listing is courtesy of: CENTURY 21 CARIOTI (407-566-0555)

Listing Agent: Evagisela Rodriguez (407-566-0555)

Remarks: One or more photo(s) has been virtually staged. Welcome to 2365 Rapollo Drive, located in the highly sought-after gated community of Tapestry in Kissimmee! This beautifully maintained residence offers the perfect blend of comfort, style, and convenience. Featuring a spacious open-concept floor plan, this home is ideal for both everyday living and entertaining. The chef-inspired kitchen boasts modern cabinetry, granite countertops, stainless steel appliances, and a large center island overlooking the living and dining areas. Natural light fills the home, highlighting the thoughtfully designed layout and generous living spaces. The primary suite offers a with a walk-in closet and an ensuite bath complete with dual vanities and a spacious shower. Additional bedrooms provide flexibility for guests, a home office, or growing needs. Step outside to the fenced backyard space perfect for relaxing evenings or weekend gatherings. Residents of Tapestry enjoy resort style amenities including a clubhouse, sparkling pool, fitness center, and 24hr gated/guarded security. Conveniently located near The Loop shopping center, major highways, dining, and just minutes from world-famous attractions and Orlando International Airport. Don’t miss this opportunity to own in one of Kissimmee’s premier communities. Call to schedule your private showing today! Virtual tour available (English): https://youtu.be/g8VTYhJaErk . Virtual tour available (Spanish): https://youtu.be/MxjL10fnLpE

Listing is courtesy of: AGG REALTY & MANAGEMENT LLC (407-267-7926)

Listing Agent: Amar Guemraoui (407-267-7926)

Remarks: Fully Furnished & Move-In Ready Villa!! Welcome to this beautifully updated 2-bedroom, 2-bath villa located in the heart of Kissimmee! This turnkey home is being sold fully furnished, making it the perfect opportunity for first-time buyers, seasonal residents, or investors looking for an immediate rental. Step inside to find a bright and open layout featuring tile flooring throughout, an updated kitchen, and a comfortable living space ready to enjoy from day one. Recent improvements include a new roof, giving peace of mind for years to come. Enjoy low-maintenance living in a well-established community offering amenities such as a pool and tennis courts, all while being just minutes from shopping, dining, and entertainment at The Loop, major highways, and area attractions. Whether you’re looking for a primary residence, vacation home, or income-producing property, this one checks all the boxes: Prime location, Fully furnished, Move-in ready, Incredible value. Seller is motivated—schedule your showing today!

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

Listing Agent: Angie Pereira (407-721-8945)

Remarks: FULLY RENOVATED HOME on an oversized 0.40-acre corner lot in Kissimmee with NO HOA! Major 2025 upgrades include a new roof, new A/C, all new windows, updated electrical and plumbing systems — offering true peace of mind. Features include an open-concept layout, luxury vinyl flooring, fully remodeled bathrooms, blinds, and a modern kitchen with quartz countertops and a large island. The fully fenced yard provides incredible space to build a pool, expand, or park your RV and boat with no restrictions. Prime central location near major highways, shopping, dining, and schools. Move-in ready with space, upgrades, and freedom — a rare find.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Arlenys Oviedo (786-803-4342)

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: One or more photo(s) has been virtually staged. SELLER ASSISTING WITH BUYER FINANCING, 2/1 BUYDOWN ON THE INTEREST RATE! Welcome to this wonderful 3-bedroom, 2-bathroom completely renovated home offering nearly 2100 sq. ft. of living space in the highly desirable Harbour Oaks community in Kissimmee, Florida. This spacious residence is designed for both comfort and style, featuring an open-concept layout, modern finishes, and thoughtful upgrades throughout. This renovation includes NEW Roof-Soffits-Gutters, Interior and Exterior Paint, both Bathrooms and Kitchen rehabs with Quartz Stone counters, SS Appliances, Breakfast Bar, Wet Bar, Luxury Vinyl Flooring, Blinds and Ceiling Fans throughout, Pool Refinished, Painted Decks front and back, Wood Burning Fireplace, Oversized 2-Car Garage, Pool Gazebo and Vinyl Fenced backyard. Enjoy your own private outdoor oasis with a sparkling pool and huge back yard—perfect for year-round Florida living and entertaining. Located just minutes from Historic Downtown Kissimmee, you'll have convenient access to shopping, dining, and entertainment. You're also perfectly positioned with a quick commute the Florida Turnpike, Lake Nona Medical City, major theme parks, schools, shopping and dining and the stunning Space Coast beaches. With its generous floor plan, multiple living areas, and every exceptional upgrade, this remarkable home has it all. Don’t miss your chance—schedule your showing today!

Listing is courtesy of: MACERA REALTY GROUP INC (407-246-1677)

Listing Agent: Peter Macera (407-970-2104)

Remarks: 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, and a newer water heater, 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. 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!

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

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

Remarks: EXCEPTIONAL INVESTMENT OPPORTUNITY OR DREAM VACATION HOME! Welcome to 2260 San Vital Dr #108, a stunning and spacious 4-Bedroom, 3-Bathroom residence perfectly situated in the world-class, guard-gated resort community of Venetian Bay Villages in Kissimmee, Florida. This property offers the perfect blend of comfort, style, and high-income potential in one of Central Florida’s most sought-after short-term rental zones. UNIQUE DUAL-MASTER FLOOR PLAN: This rare and highly functional layout is a favorite among vacationers and large families. It features TWO PRIMARY EN-SUITES: one conveniently located on the first floor for easy access, and a second private master suite on the upper level. This configuration ensures maximum privacy and flexibility for multi-generational living or groups of up to 10 guests. The ground floor boasts an open-concept living and dining area with tall ceilings and plenty of natural light, flowing into a fully-equipped kitchen with a breakfast bar. Two additional guest bedrooms share a third full bathroom, providing a comfortable and balanced living space. RESORT-STYLE LIVING AT ITS FINEST: Living in Venetian Bay Villages feels like a permanent vacation. This Mediterranean-inspired community is meticulously maintained and offers an unparalleled amenity package included in your HOA fee: 24/7 GUARD-GATED SECURITY: Peace of mind with a manned entrance and security patrol. FOUR SPARKLING SWIMMING POOLS: Including a large heated main pool near the clubhouse and three satellite pools throughout the village. ELITE CLUBHOUSE: Featuring a state-of-the-art fitness center, a private movie theater, a game room/arcade, and a business center with high-speed internet. SPORTS & RECREATION: Professional-grade tennis courts, basketball courts, and sand volleyball courts. FAMILY-FRIENDLY: Multiple playgrounds, picnic areas, and scenic walking trails around serene community ponds. STRATEGIC LOCATION IN THE HEART OF THE MAGIC: Location is everything! This property is strategically positioned for maximum occupancy and convenience: MINUTES FROM DISNEY: Less than 10-15 minutes from Walt Disney World Resort main gates. CLOSE TO ATTRACTIONS: Short drive to SeaWorld, Universal Orlando Resort, and Disney Springs. SHOPPER’S PARADISE: Located just around the corner from The Loop Shopping Center, featuring premier retail, a multi-screen cinema, and dozens of popular dining options. EASY TRAVEL: Quick access to Osceola Parkway, John Young Parkway, and I-4. Only 20 minutes from Orlando International Airport (MCO). INVESTOR HIGHLIGHTS: This property is TURNKEY and ready for immediate occupancy or rental. Short-Term Rentals (Airbnb/VRBO) are fully permitted by the association. The HOA is comprehensive and covers: EXTERIOR MAINTENANCE, ROOF REPLACEMENT, LANDSCAPING, TRASH REMOVAL, WATER/SEWER, AND 24-HOUR SECURITY. This significantly lowers the owner's insurance costs and simplifies management. Whether you are looking for a high-performing asset to add to your short-term rental portfolio or a luxurious primary residence where every day feels like a getaway, this Venetian Bay gem is a must-see. Properties with 4 bedrooms and dual suites are in high demand and do not last long on the market. SCHEDULE YOUR PRIVATE TOUR TODAY AND START LIVING THE FLORIDA LIFESTYLE!

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Marcos Urbina (321-388-3150)

Remarks: Under contract-accepting backup offers. This beautiful single family home is just a few minutes away to Osceola High School, downtown and Kissimmee Lakefront. Great location close to shopping areas, access to mayor roads and schools. NO HOA, NO CDD. This property is well conserved with an oversize lot ,nice sunny backyard with fruits trees, a large patio, aboveground pool and cover lanai provides plentiful space for gardening and entertaining. The garage is converted into a 4th bedroom but can be easily convert back to a full garage and still have the a garage door. New roof installed in 2023.

Listing is courtesy of: ONE TEAM REALTY (407-530-5006)

Listing Agent: Yolanda Soto Rosado (407-530-5006)

Remarks: Spacious 4-bedroom, 3-bath single-family home on a generous 0.31-acre corner lot with no HOA! This versatile property offers an ideal layout with an eat-in kitchen, inside laundry, and a welcoming front bonus/sitting room perfect for a home office, reading area, or flex space.The split-style floor plan provides comfortable living for multi-generational households, or rental opportunities. Located within a block away from AdventHealth, making it especially appealing for healthcare professionals, traveling nurses, or long-term rental potential. Conveniently close to shopping, dining, and everyday amenities. Zoned for professional office use, offering rare flexibility for buyers seeking a live/work opportunity, small business location, or future investment potential. A unique opportunity for first-time buyers, investors, or entrepreneurs looking for space, location, and versatility.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Carlethia Burnette (407-970-7902)

Remarks: Refined comfort meets Florida lifestyle in this spacious 5-bedroom 5 bathroom home within a gated community overlooking a tranquil pond. Offering 2,790 heated sq ft, the home features a versatile layout ideal for both daily living and entertaining. Bright living areas open to a screen-enclosed paver patio with water views and no rear neighbors, creating a peaceful outdoor retreat. Mature palm landscaping enhances the home’s tropical appeal. Built in 2008 and well maintained, the 5-bedroom, 5-bath layout provides flexibility for guests or work-from-home needs. Community amenities include a pool, sports courts, playground, and walking paths. Conveniently located near shopping, dining, schools, Orlando International Airport, and major attractions. A great opportunity for buyers seeking space, privacy, and location. Schedule your showing today.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Priscila Triska (321-354-5459)