Homes for Sale Near Osceola High School in Kissimmee - 87 homes

Remarks: Location, location! Don't miss this opportunity to live in Tapestry community First time buyers ,investors Spectacular 4/3 with a beautiful landscaping exclusively designed for the property, it is located in one of the best areas of Kissimmee, with good access to I4, Osceola pkwy, 417, 528 and turnpike, access to everything you need for your daily living. It is a 24 hour guarded gate community with excellent amenities In addition, the house has a covered and completely fenced patio to generate privacy in your patio and your parties. Don't miss out on this opportunity.

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

Listing Agent: Juan Oberto (407-810-3694)

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

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

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

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

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

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: $80,000 price improvement — now offered at $530,000 in the gated Tapestry community, just 15 minutes from Disney. Proudly owned by only one owner, this fully modernized 4-bedroom + office + loft, with 3.5-bath, offers nearly 2,400 sq ft of functional living space. Including a downstairs bonus room and a spacious upstairs loft. The private backyard is a standout feature, designed for comfort and entertainment with artificial turf, paved gathering areas, a jacuzzi, and full fencing for added privacy and low maintenance. Additional highlights include a 2-car garage and fully installed security system. Conveniently located just 0.7 miles from Kissimmee Middle School and minutes from major shopping, dining, and highways. Residents of Tapestry enjoy true resort-style living with a clubhouse, resort pool, water play area, playgrounds, dog park, scenic conservation areas, and a fully equipped fitness center. With this new price adjustment, opportunities like this don’t last — schedule your private tour today.

Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)

Listing Agent: Gabriella Massaro (689-280-9558)

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

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

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

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

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

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

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

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

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

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

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

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

Remarks: Take a look this furnished townhome in a gated community. The layout includes a 3 bed, 2 and 1/2 bath, a front portico, 1 rear balcony, and a rear entry 2 car garage. Downstairs you'll find the kitchen with granite countertops is also fully tiled and contains a large living space and convenient half bathroom. All of your bedrooms are located upstairs for your privacy and convenience.The master bedroom features walking closet and a large balcony perfect for your morning coffee.Tapestry offers 24 hours private security, a Resort style Club House like no other in the area, beach entry pool with slide and splash pad, grill area , fitness center, walking trails and more! Enjoy this beautiful property located just minutes from Orlando International Airport and the world-famous Disney and Universal theme parks. Schedule your appointment today!

Listing is courtesy of: YORK MILLS REALTY LLC (407-620-8528)

Listing Agent: Leo Shao (407-569-6769)

Remarks: COMPLETELY REMODELED WITH OVER $50,000 IN UPGRADES. HOME HAS BEEN LEASED

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

Listing Agent: Lorinda Orozco, Pa (407-562-8757)

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: 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: Under contract-accepting backup offers. Located within a secure gated community, this townhome offers a practical layout with tall ceilings, wood-look tile and LVP flooring throughout, and an enclosed garage for added convenience. A clear water view gives the main living area a calm backdrop, and all appliances come included for an easy move-in. With access to a community pool, low HOA fees, and no CDD, this low maintenance home offers a strong option for anyone looking to be near shopping, dining, and the Orlando attractions.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Christian Clay (863-509-7466)

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: Welcome to this stunning move-in-ready home where thoughtful design, premium upgrades, and energy efficiency come together in perfect harmony. This beautifully maintained home offers the perfect balance of luxury, comfort, and convenience. From first glance, curb appeal impresses with a stone-accented front elevation, well-maintained landscaping, and a striking red brick walkway leading to a covered front porch. Step inside to a bright, airy foyer featuring polished porcelain tile, clean architectural lines, and a sleek glass-panel staircase setting the stage for the refined interior that follows. The open-concept main level is both stylish and highly functional. The family room is anchored by a custom entertainment wall with textured paneling, LED accent lighting, and a floating media console, an ideal setting for relaxed nights or elegant entertaining. Crown molding, recessed lighting, and a soft neutral palette enhance the elegant atmosphere, while wide visibility flow effortlessly into the dining area and kitchen. The kitchen is a true showpiece; a modern, sleek, and designed for both culinary performance and visual impact. High-gloss white cabinetry offers ample storage, white stunning quartz countertops with bold veining wrap around a dramatic waterfall island that doubles as a prep space and social hub. The waterfall island is anchored by a distinctive tile inlay, elevating the kitchen’s designer aesthetic., complemented by a sculptural LED pendant light overhead and ambient LED ceiling lighting throughout. Outfitted with premium stainless-steel appliances, the kitchen includes a Samsung French door smart refrigerator with digital display, double wall ovens, a smooth cooktop with a stylish range hood, and an integrated dishwasher. A continuous marble-look quartz backsplash ties the space together. Adjacent to the kitchen, the dining area is bathed in sunlight from sliding glass doors that lead directly to the backyard. Tucked beneath the staircase is a custom-designed bar nook complete with a stacked stone backsplash, glass shelving, recessed lighting, and a built-in beverage cooler, ideal for relaxing evenings or hosting guests. Nearby, a built-in display wall with individually lit niches offers a refined way to showcase art, collectibles, or personal décor. Upstairs, a spacious loft serves as a second living room or media lounge, featuring a textured accent wall, floating console, and contemporary lighting. Glass-panel railings maintain the home’s open feel while adding a modern edge. The primary suite is located on the first floor, offering privacy and comfort. The ensuite bathroom includes a built-in closet system for efficient storage, along with updated fixtures and finishes for a clean, spa-like feel. Each bedroom features porcelain tile flooring, modern ceiling fans, and ample natural light. Bathrooms are tastefully updated, with three full baths and a convenient half-bath. Step outside to your private backyard retreat. A large, covered patio with wood-beam construction offers shaded comfort, while an expansive paver patio provides plenty of space for outdoor dining, lounging, or entertaining. A curved paver walkway leads past dual HVAC units and the solar energy system. Nestled just minutes from The Loop—a vibrant open-air shopping and entertainment destination, movie theaters, 20 minutes from Orlando’s world-famous theme parks and the Orlando International Airport. Schedule your private showing today!

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

Listing Agent: Carmen Estrella (407-960-0914)

Remarks: This cozy Villa/Townhome offers 2 bedrooms and 2 full bathrooms, with 930 square feet of living area in the hearts of Kissimmee. This home features open floor plan, ceramic tiles flooring throughout, screened & covered front entry, living/dining combo, skylights in kitchen, inside separate laundry, nice outside sitting area, large vinyl fenced yard, low HOA, and Taxes. Enjoy the fresh air or cool off in the fenced in backyard. Property located very close proximity to Schools, Public Transportation (junction of public bus), Dining, Shopping, Banking, Loop Mall, Wal-Mart, Hospitals, Doctors Office, Major Roads (US 192, Osceola Parkway, John Young Parkway) and Major Attractions. This Townhouse is in great shape and recently updated plumbing system. An excellent opportunity for the first time homebuyer or investor. *All the information relating to this MLS Listing is intended to be accurate but cannot be guaranteed and must be verified by the buyer and buyer's agent. Opportunity knocks - ACT FAST!

Listing is courtesy of: PROFILES INTERNATIONAL REALTY (321-297-8161)

Listing Agent: Mohammed Hossain (407-925-3442)

Remarks: One or more photo(s) has been virtually staged. BACK ON THE MARKET! Spacious and VERY WELL-MAINTAINED 3-bedroom, 2-bath condo located on the 2nd floor in the desirable gated community of Flora Ridge in Kissimmee. This inviting condominium features wood-style flooring in the open great room, tile in the wet areas, and cozy carpet in the bedrooms. The split floor plan offers added privacy, with the primary suite separated from the other two bedrooms. The primary ensuite includes dual sinks, a private water closet, and a sleek walk-in shower—perfect for those who prefer ease of access and modern comfort over a traditional bathtub. The bright kitchen is equipped with all stainless steel appliances, lots of cabinets and counter space, a pantry closet, and a convenient washer and dryer area discreetly enclosed by a pocket door. Open both French doors to enjoy the outdoors from your screened-in balcony, perfect for relaxing or entertaining. Flora Ridge has fantastic amenities including a community pool, a gazebo, and serene waterfront walking path ideal for peaceful strolls and sunset views. Conveniently located within 3 minutes of Osceola Parkway, 7 minutes from The Loop shopping centers, and about 2 miles from the 417 Toll; this home provides easy access to major roads, schools, restaurants, and shopping areas. Majestically set away from the hustle and bustle, yet close enough to everything you need!

Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)

Listing Agent: Luz Lovera (407-325-5027)

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: Brand New Interior Paint--Move in Ready! Welcome to the beautifully maintained 3 Bedroom 2-Bathroom home located in the desirable gated community of Cypress Reserve! Featuring an open concept layout with wood flooring throughout, crown molding and window treatments! This home offers both style and comfort on a gorgeous, oversized lot! The kitchen is fully equipped with a refrigerator, dishwasher, oven and microwave and showcases Corian countertops, tiled backsplash, maple cabinetry, and a closet pantry. An eat-in area just off of the family room creates the perfect space for casual dining and everyday living. The spacious primary suite and secondary bedrooms offer a functional split floor plan. A 2023 AC and 2018 ROOF provides a peace of mind. Washer and dryer convey with the sale. Step outside and enjoy a large, enclosed lanai overlooking an expansive backyard--ideal for entertaining or relaxing year-round. Move in ready and conveniently located near shopping (The Loop), dining, and major roadways. Come and see this home today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Catherine Lambert Pa (407-908-2525)

Remarks: Under contract-accepting backup offers. Fully renovated from top to bottom, this 4-bedroom, 3-bath home offers 2,760 square feet of thoughtfully redesigned living space on a spacious .35-acre cul-de-sac lot — with no HOA. From the moment you enter, the home makes a statement. A striking glass staircase sets the tone, adding architectural interest and modern edge that immediately separates this home from the ordinary. An abundance of newly installed lighting fills the space with bright, natural warmth, while wide-plank luxury vinyl flooring runs seamlessly throughout for a clean, cohesive look. The kitchen was designed to impress and perform — featuring brand-new cabinetry, sleek quartz countertops, stainless steel appliances, and a generous island that anchors the room. It flows effortlessly into the open-concept living area where a remodeled fireplace adds warmth and balance to the contemporary finishes. The primary suite feels like a private retreat. With two access points — including a dramatic spiral staircase — the space offers flexibility and character rarely found at this level. The spa-inspired primary bath delivers a true oasis feel, complete with a freestanding soaking tub and dual shower heads designed for a luxurious, everyday escape, while each bathroom showcases brand-new custom tile showers, modern vanities, and quartz countertops that feel straight out of a design magazine. All four bedrooms offers comfortable, usable space, and each includes a custom closet system for elevated organization and functionality. Major updates have already been handled: brand-new roof, fresh interior and exterior paint, and a newly resurfaced pool provide both style and peace of mind. Step outside to a large covered patio overlooking the pool and jacuzzi — a true Florida backyard built for entertaining or unwinding year-round. The oversized driveway and 2-car garage allow for multiple vehicles, guests, or recreational toys, while the expansive lot still leaves room to breathe. Architecturally distinctive, fully updated, and positioned on a generous lot in a prime area, this is the kind of home that stands out — especially at this price point. Experience it in person and see why it feels different the moment you walk in.

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Rosemary Camilo Diaz (407-791-7152)