Homes for Sale Near Osceola High School in Kissimmee - 77 homes

Remarks: Prime opportunity in a highly desirable location! Conveniently located just minutes from Old Town, major entertainment, and top hospitals—and only 20 minutes from Walt Disney World—this home is perfectly positioned for strong rental demand. Recent upgrades include a brand-new roof, updated electrical, new flooring, and a newly installed fence, providing peace of mind and low maintenance for years to come.Whether you’re looking to make this your primary residence or add a performing asset to your investment portfolio, this property delivers both value and versatility. Don’t miss this incredible opportunity!

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

Listing Agent: Amanda Little (407-720-9728)

Remarks: Under contract-accepting backup offers. Fantastic Regal Oak Shores Pool Home located on more than a half-acre of tropical and oak forest. 4 bedrooms/ 2 full baths. NO HOA! The pool is completely screened in, with a large entertaining area, including a generous covered portion and 4 access points. At any time of day, the home is light, bright, and welcoming. Lake Toho (across the street and 10 minutes from the access point) is Florida's 4th largest lake! Lake Toho is known to be the top destination for outdoor recreational sports, including Bass fishing, boat ramps, kayaking/canoeing, and airboats. Close to all the theme parks and entertainment destinations, including some of the top dining establishments in the nation. Super quiet neighborhood on a dead-end street that has no ambient lighting for amazing stargazing and late-night dips in the pool. Located about 25 minutes from Downtown Orlando, but with very close access to Florida's Turnpike and 429. Home has a NEW ROOF.

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

Listing Agent: Eric Rollings (407-256-2470)

Remarks: Welcome to the established, sought after community of Kings Point! With larger lots, and NO HOA, neighborhoods like this are hard to find in today's market. This home sits on just over a third of an acre and has beautiful, mature oak trees. It is a 3 bedroom, 2 bathroom home with an open floor plan that offers plenty of space for the family. A split bedroom plan offers a little extra peace for the primary bedroom. The skylight right inside the front door offers beautiful natural light for the living area. A sliding glass door takes you out to the gigantic screened in porch that overlooks the spacious back yard. The home also features a 2 car garage. The roof was replaced in 2021 and the water heater is brand new. While tucked away down Kings Highway, the home is not far from the turnpike, which makes commuting a breeze.

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

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

Remarks: Huge Price Reduction! 2 Bedrooms, 2 baths, living room, dining room, Porch, 2-car garage, plus parking for extra cars; Community allows! RV or a Boat, NOA HOA! LOT INCLUDED! Super Well Located! walking distances to the mall (The Loop), Financial institutions, Church, Bus stop, easy train commute, Hospitals, Schools. Best prices in town, sellers are super motivated!

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

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

Remarks: FULLY FURNISHED and ready to move in! The perfect vacation home or permanent getaway. A television comes complimentary, as do various appliances. Community features a large lake with a fountain and resort-style lounge chairs on a custom patio. The downstairs master bedroom suite and two bedrooms complete the upstairs. Separate bathrooms for each floor as well. Large sofas, TV, beautiful dining room table, we could go on and on! Truly a must-see to appreciate! Exclusive community with mannedgates functioning 24/7. Quiet area with picturesque views and scenic streets. Be the envy of your old neighbors and the best friend of your new ones - own today! Buyers should independently verify HOA dues and room measurements.

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

Listing Agent: James Williams Iii, Pa (321-402-6261)

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: Hot water heater and stove are gas. Will not qualify for FHA loans- condo complex is not on FHA approved condo list. Community does not allow for short term rentals. Please check with property management company for pet restrictions. Please use "As-Is" FR/BAR contract. Text the listing agent to set up an appointment.

Listing is courtesy of: R LUGO REALTY (407-346-9920)

Listing Agent: Rosa Hernandez (407-346-9920)

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.

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

Listing Agent: Blanca Hernandez, Llc (407-493-9895)

Remarks: This 1-bedroom, 1-bathroom condo is in excellent condition and features a private balcony, 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. This is an investment property. The HOA fee includes water, sewer, Wi-Fi, trash, and pest control.

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

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

Remarks: This fully renovated 3-bedroom, 2-bathroom home sits on a spacious corner lot (almost a quarter acre lot) at the intersection of Michigan Avenue and Marygon Street, near U.S. 192. Located outside of a flood zone and free of HOA restrictions, this property offers maximum flexibility for both owner-occupants and investors. The backyard was fully fenced in 2023. Inside, the home features a bright and functional layout with no carpet at all. The kitchen includes custom-made cabinets, Lazy Susan corner cabinets for efficient storage, generous counter space, and a dedicated dining area. All stainless steel kitchen appliances are included. The master bedroom goes from the front of the house to the back of the house making it a nice size and comfortable bedroom to spend time relaxing, resting or watching TV. The original garage has been converted into a bedroom and an office, expanding the usable living space and allowing for multiple layout options such as a home office, guest room, or additional bedroom. The home now offers two full bathrooms. The main bathroom includes a shower and tub combination. An indoor laundry room is located inside the home and includes a washer and dryer. Exterior features include a fully fenced yard suitable for pets, outdoor activities, or gatherings. A rear screened porch with ceiling fans provides additional covered outdoor space. The patio area offers ample room to park a food truck, an RV, a boat/jet skis, landscaping equipment, or a work trailer, with easy access through the right-side gate. There is a shed in the patio as well for added storage. Recent upgrades completed in 2023 include a new roof, new water heater, new fence, a new bathroom, new appliances, and a new rear screened porch. The photographs accurately represent the property as it currently exists. No alterations or enhancements have been made to the images. This move-in-ready property is suitable for a first-time homebuyer or an investor seeking a centrally located home with no HOA and no rental restrictions. The location provides convenient access to major destinations, including less than 30 minutes to Valencia College, Walmart, The Loop Shopping Center, downtown Kissimmee, Florida’s Turnpike, SR 417, and Orlando International Airport. Schedule your private showing today before it gets SOLD!

Listing is courtesy of: COLLECTIVE GROUP REALTY, CORP (321-244-3000)

Listing Agent: Carlos Diaz (321-244-3000)

Remarks: An incredible opportunity—seller is open to offers. Don’t wait… bring your offer before someone else does. NOW OFFERED AT $555,000 IMMACULATE & MOVE-IN READY! Welcome to this stunning Antigua model located in the gated community of Tapestry with 24-hour live security guards at the entrance. This beautifully upgraded home offers the perfect blend of elegance, comfort, and functionality. Featuring 3 bedrooms on the first floor, a versatile bonus/flex room, and an upstairs loft, along with 3 full bathrooms and 1 half bath, this home is designed for both everyday living and entertaining. One of the secondary bathrooms on the first floor is a convenient Jack & Jill bathroom, ideal for shared use between bedrooms. The primary suite is conveniently located on the first floor and offers direct access to the backyard, dual vanities, a soaking tub, and a walk-in shower. The flex room is ideal for a home office, playroom, or additional living space. Upstairs, you’ll find a spacious loft with its own full bathroom (walk-in shower, no tub), perfect for guests, a private retreat, or an entertainment area. Step into an open and bright floor plan featuring a chef-inspired kitchen with quartz countertops, stainless steel appliances, 42-inch cabinets, and a large center island that serves as the heart of the home. Enjoy peaceful conservation views with no rear neighbors, plus a screened lanai, pergola-covered patio, and a fully fenced backyard—ideal for relaxing or entertaining. Additional features include a tile roof, 2-car garage, interior laundry room, and low HOA. Residents of Tapestry enjoy resort-style amenities including a luxury pool, fitness center, clubhouse, walking trails, playgrounds, and high-speed fiber optic internet throughout the community. Prime location just minutes from Disney, The Loop, dining, shopping, and major highways. Schedule your private showing today.

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

Listing Agent: Sol Peinado (407-486-5259)

Remarks: One or more photo(s) has been virtually staged. This lovely, spacious condo in Kissimmee's gated Flora Ridge community offers the perfect combination of comfort and convenience. Located on the second floor with an elevator, this 1,779-square-foot apartment has an open layout that flows seamlessly between the kitchen and living room. There is also freshly painted interior throughout the unit, a recently replaced refrigerator, air conditioning and water heater, a master bedroom with double sinks and walk in closet, and a screened porch. Homeowners get two dedicated parking spots, one with a covered carport and one without. There is a community pool with amazing water view, and walking trail. It is situated just minutes from The Loop, a premier shopping and dining destination, making it easy to access the Florida Turnpike, Osceola Parkway, and world-famous theme parks. Along with the regular assigned schools, there is Renaissance Charter School with an A rating available from Kindergaden to 12th grade.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Brigitte Elzarki (321-231-4999)

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: Under contract-accepting backup offers. Welcome to 2331 W Oak St in the heart of Kissimmee! This charming 3-bedroom, 1-bath home plus a separate 1/1 unit offers fantastic flexibility—perfect for extended family, guests, or potential rental income. Enjoy peace of mind with impact windows, a 2020 roof, and a whole-home water softener. The updated kitchen features modern finishes and a bright, functional layout. Outside, the property boasts a spacious backyard and covered areas ideal for gatherings, cookouts, and outdoor entertainment. Located just minutes from world-famous Disney parks, major roads, shopping, dining, and all that Central Florida has. Don’t miss this versatile and move-in ready opportunity!

Listing is courtesy of: VITA LUXURY REALTY LLC (813-412-9468)

Listing Agent: Annay Hernandez (727-777-4222)

Remarks: Beautiful two-bedroom, two-bathroom apartment, completely remodeled. This unit is on the 3rd floor of The Villas del Sol Condo community.The building and complex have been completely renovated; gated community with resort style amenities, like swimming pools, Playground, fitness center and Tennis courts. The property can be used as long term or short term rental! Located near major highways for easy access to Central Florida attractions.

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

Listing Agent: Carlos Villamil (407-340-0042)

Remarks: fantastic Location in a desirable gated community, close to restaurants, grocery stores, theater, very accessible to the airport and theme parks, schools, work out clubs, walkways everything you need, with a heated screen in pool overlooking a beautiful view of the pond with a fountain for peaceful evenings from your enclosed lanai, move in ready very well-kept house with newer roof, a/c, you will love the location, location.

Listing is courtesy of: THE EXPERTS TEAM REALTY INC (407-674-7994)

Listing Agent: Eve Hefner (407-509-1517)

Remarks: One or more photo(s) has been virtually staged. .Some condos feel basic. This one feels cared for. Located on the THIRD FLOOR with convenient ELEVATOR ACCESS, this 3-BEDROOM, 2-BATH residence in GATED Flora Ridge offers 1,433 square feet, a light and airy OPEN FLOOR PLAN, SOARING CEILINGS, and a SCREENED BALCONY for relaxed outdoor living. The MODERNIZED KITCHEN features QUARTZ COUNTERTOPS, STAINLESS STEEL Whirlpool appliances, a STAINLESS SINK, updated faucet, garbage disposal, and BREAKFAST BAR seating overlooking the living and dining areas. Additional highlights include LAMINATE WOOD FLOORING in the main living spaces, SHERWIN-WILLIAMS paint throughout, NEW WINDOW BLINDS, CEILING FANS throughout, LED lighting in the guest bath, FULL-SIZE Whirlpool WASHER AND DRYER, and HURRICANE-IMPACT DUAL-PANE WINDOWS in the primary and guest bedrooms. SMART HOME features include a WiFi-enabled entry lock, Nest thermostat and camera, wireless alarm with cellular connection, and UPS backup for the cable modem. Offered MOSTLY FURNISHED, this home is MOVE-IN READY for a primary residence, seasonal retreat, or LONG-TERM INVESTMENT. Flora Ridge offers a COMMUNITY POOL, CLUBHOUSE, scenic lake with fountain, walking paths, ON-SITE PROPERTY MANAGEMENT, and NO SHORT-TERM RENTALS — a meaningful advantage for long-term value and pride of ownership. Ample community parking is available, with most spaces COVERED BY CARPORTS, and the association maintains the EXTERIOR, ROOF, AND GROUNDS for true LOCK-AND-LEAVE convenience.

Listing is courtesy of: THE ROSENBLOOM TEAM (407-376-4454)

Listing Agent: Cindy Rosenbloom (407-876-9175)

Remarks: If you thought you couldn't find an incredible 3-bedroom property with an upstairs entertainment area, 2.5 bathrooms, and a private pool, featuring elegant and comfortable spaces, the seller has created a versatile space that can be used as a fourth bedroom or office, added a shower to the half bathroom, and the home boasts spacious bedrooms, a large kitchen, and a three-car garage. Enjoy a modern kitchen, living room, pool, and a pergola with a barbecue area perfect for entertaining family and friends. Don't miss the opportunity to own this property; a true luxury home awaits you, situated on 0.32 acres of land. This community offers convenient access to shopping areas and major roadways. Let's schedule a showing so you can experience this fabulous property. The seller is motivated to negotiate.

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

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

Remarks: SELLER MOTIVATED - PRICE TO SELL - GREAT OPPORTUNITY STUNNING FULLY RENOVATED 3 BEDROOM POOL HOME – PRIME LOCATION IN KISSIMMEE Welcome to this beautifully upgraded 3-bedroom, 1 bonus room, 2-bathroom home located and a spot available with possibility to build a one more bathroom. This property has been completely renovated with high-end finishes throughout and offers the perfect blend of elegance, comfort, and Florida lifestyle living. Fully renovated interior. Premium, first-line flooring throughout. Sophisticated wood panel accent walls. Designer-decorated bedrooms. Completely remodeled kitchen with modern finishes. Updated bathrooms with contemporary style. Extended driveway for additional parking Private heated pool with spa. Outdoor gourmet area perfect for entertaining. Beautiful pond water view with a colonial-style architectural details. Gated community for added security. The open floor plan creates a bright and welcoming atmosphere, ideal for both primary residence, vacation home, or investment property. The backyard is a true retreat, featuring a heated pool and spa overlooking a peaceful pond view — perfect for relaxing evenings or entertaining guests. This home shows pride of ownership and attention to detail in every corner. The bedroom furniture has been removed; the summer kitchen needs to be finished, and the refrigerator was removed because it was broken. Seller is highly motivated and priced to sell. Excellent opportunity in one of Kissimmee’s most sought-after areas, close to major highways, shopping, dining, and attractions.

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

Listing Agent: Francisco Tatagiba Junior (386-517-3488)

Remarks: Townhome available and ready to move in, featuring 3 bedrooms, 2.5 bathrooms, and a one-car garage, located in the gated community of Flora Ridge, conveniently near the Loop. The welcoming entry opens to a well-appointed kitchen with breakfast bar, seamlessly flowing into the open-concept living room and dining area—perfect for everyday living and entertaining. Upstairs, you’ll find three spacious bedrooms, two full bathrooms, and a built-in workstation ideal for remote work or study. Enjoy close proximity to Shopping, Schools, Dining, and more. Schedule your private showing today!

Listing is courtesy of: BROKERS REAL ESTATE GROUP INC (407-770-1464)

Listing Agent: Rich Canelon (407-341-4035)