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

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

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

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

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

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

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

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

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

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

Remarks: One or more photo(s) has been virtually staged. "Huge PRICE REDUCTION for quick sale." Welcome to your dream home in the luxurious Weston Reserve gated community. This stunning former model home combines spacious, thoughtful design with prime location, offering the perfect balance of privacy and accessibility. Situated just about a mile from the Loop shopping complex and walking distance of Flora Ridge Elementary School, Publix supermarket, Floor and Decor, and premium shopping, this property defines "move-in ready." It is also ideally located just a few miles from Disney, Sea World, and about a twenty minute to the Orlando International Airport. Designed for those who love to cook and entertain, the expansive kitchen features rich 42-inch-high wood cabinets, a central island and a galley pantry. High-end upgrades include a fairly new cook top, a new dishwasher and a double convention oven. There are also a wet bar and an elegant half bath by the stairs to the second floor. The kitchen flows seamlessly into a breakfast nook and a light filled family room with custom built ins. Step through the sliding glass doors to your own private paradise. The screened-enclosed poor area, equipped with a baby fence, offers a serene retreat for soaking up the Florida sun or hosting weekend gatherings in a secluded setting. As you entered through the 8ft high front door, you are greeted with an elegant family and dining rooms. On the left is the guest room with its own dedicated bathroom and on the right is the 100 square feet office with custom built-in desk and bookshelves. Go up the recently installed hardwood stairs to the second floor and find two bedrooms which are connected by a Jack and Jill bathroom and the massive primary bedroom which serves as a true sanctuary, boasting dual walk-in closets, double vanities and a luxurious garden tub. The property also features a new roof that was installed in 2021, 2 HVAC systems that were installed less than three years ago along with a fairly new water heater and pool pump and new paint interior and exterior. Don't let this incredible opportunity pass you by. Call for an early showing.

Listing is courtesy of: HOMESTEAD REALTY INC (407-367-4201)

Listing Agent: Patrick Matthews (321-663-2623)

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

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

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

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

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

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

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

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

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

Remarks: Newly Renovated! This is a cozy and very spacious 3-bedroom/2-bath condo in the lovely Flora Ridge gated community on the 3rd floor with convenient elevator access. Featuring split floor plan, luxury vinyl flooring throughout the unit and lots of natural light. The kitchen has a breakfast nook, new sink, faucet and stainless-steel range. Ceiling fan is in the living room and each bedroom. Laundry room has washer and dryer included. Primary suite features a large walk-in closet, a very large bathroom with his and her sink. The screened-in patio is perfect for relaxing and entertaining family and friends. The community features a pool, parks and walking trail. Located near major highways with easy access to Disney, restaurants, shopping, many Attractions and entertainment. This one is just waiting for you to call home!!

Listing is courtesy of: EATON REALTY SERVICES (800-630-1990)

Listing Agent: Arlene Cowan (800-630-1990)

Remarks: One or more photo(s) has been virtually staged. Seller is Highly Motivated – Bring All Offers! Welcome to the gated community of Windsor Point, where comfort, convenience, and natural beauty come together. This spacious 3-bedroom, 2-bath residence with a versatile flex room offers a thoughtfully designed layout ideal for both entertaining and everyday living. Upon entering the home, you’re greeted by a welcoming foyer that opens into a bright formal living room—perfect for hosting guests or creating a peaceful sitting area. The split floor plan provides privacy, while the expansive family room serves as the heart of the home, offering plenty of space for gatherings, movie nights, or relaxing after a long day. Sliding glass doors lead to a generously sized backyard, fully enclosed with durable vinyl fencing for privacy and security. Whether you envision weekend barbecues, a play area, space for pets, or a future pool, this yard provides endless possibilities. The home features easy-care ceramic tile flooring throughout—ideal for Florida living. The spacious kitchen is designed for functionality and flow, complete with abundant cabinetry, ample counter space, and an open layout that allows you to stay connected while cooking or entertaining. The flex room can easily function as a home office, workout room, craft room, or homeschool space. Prime Location: Located just 5 minutes from The Loop, featuring upscale shopping, restaurants, and a movie theater. Enjoy quick access to major highways, including Osceola Parkway, John Young Parkway, and the Florida Turnpike, for easy commuting. World-famous attractions such as Disney theme parks, Disney Springs, and Old Town are just 6–10 miles away. Orlando International Airport (MCO) is approximately 15 miles from the property. This home offers space, flexibility, and a highly desirable location within a secure community—making it an excellent opportunity for primary homeowners, second-home buyers, or investors alike. Schedule your private tour today to fully appreciate this home's charm!

Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)

Listing Agent: Tiffany Greer (407-709-0582)

Remarks: $5,000 BUYER INCENTIVE. Use it toward closing costs, upgrades, or a rate buy-down. This 3 bedroom, 2.5 bath townhouse offers 1,702 square feet of well designed living space in a prime location. Situated directly across from the community pool and playground, the home provides immediate access to top neighborhood amenities. The interior features an open main floor layout, ideal for both entertaining and daily functionality. Upstairs, the primary suite is complemented by two additional bedrooms and a full bath, offering flexibility for guests, a home office, or a growing household. Conveniently located near major shopping centers, restaurants, and essential services, this property combines comfort, convenience, and community living. A strong opportunity for buyers seeking a well maintained home in a desirable area.

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

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

Remarks: Welcome to resort-style living in one of Kissimmee's most amenity-rich gated communities. This spacious 3-bedroom, 2-bathroom townhouse at Venetian Bay Villages offers an unbeatable combination of space, security, and lifestyle — all at a price that's hard to match in Central Florida. THE LAYOUT: This two-story floor plan features a ground-floor master suite — ideal for homeowners who want easy access or for guest privacy. Two additional bedrooms upstairs provide natural separation for family members or roommates. The open-concept living, dining, and kitchen area makes the space feel larger than the square footage suggests. MOVE-IN READY: The unit has been freshly repainted throughout and is vacant — ready for immediate occupancy the day you close. THE COMMUNITY: Venetian Bay Villages is a 24-hour staffed guard-gated community with amenities that rival full resort properties: 4 pools and a heated jacuzzi, fitness center, clubhouse with theater and game room, tennis, basketball and volleyball courts, 3 catch-and-release fishing lakes, BBQ stations, playgrounds, and a car wash area. HOA covers exterior maintenance and landscaping — truly low-maintenance ownership. THE LOCATION: Minutes from I-4 and US-192 — 13 miles to Walt Disney World, 12 to SeaWorld, 16 to Universal Studios. Steps from Walmart, Publix, Target, Burlington, Ross and The Loop shopping center. Osceola Regional Medical Center is just 2 miles away. RENTAL FRIENDLY: Both long-term leases and weekly vacation rentals (7-day minimum) are permitted with no HOA waiting period — ideal for investors who want flexibility.

Listing is courtesy of: KEYS REALTY REDEFINED LLC (305-707-0373)

Listing Agent: Randal Longo (855-944-3525)

Remarks: Under contract-accepting backup offers. 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 (2017), and a water softener system 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. Other 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! SELLER WILL PROVIDE $5000 CREDIT TOWARD NEW FLOORING.

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

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

Remarks: Discover an incredible opportunity. NEW ROOF 2022 it has 4 bedrooms with 2 masters suite, 3 bathroom home with 2 car garage in the sought-after Magical Landings community in Kissimmee! This well-maintained home offers exceptional value with just a few minor cosmetic touches needed to make it truly shine. This property is perfect for families, multi-generational living, or even a vacation home. The open-concept layout flows beautifully into a large great room, creating an inviting space ideal for entertaining and everyday living. Step outside to your own private oasis, an enclosed, screened, and heated in-ground pool, perfect for enjoying Florida living year-round in total privacy. Major upgrades include a new roof, giving peace of mind to the next owner. The home is also ideally located just minutes from the Florida Turnpike, providing easy access to everything Central Florida has to offer, including world-famous attractions like Walt Disney World. Situated in a gated community, close to schools, shopping, dining, and major roadways, this home truly combines convenience, comfort, and value. Priced to sell—this opportunity will not last! Schedule your private tour today and submit your offer before it’s gone.

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

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

Remarks: 3-bedroom, 2-bath home with a screened-in pool and pond view. No HOA. Conveniently located near shopping, Florida’s Turnpike, theme parks, and about 30 minutes to downtown Orlando.

Listing is courtesy of: REALTY ONE GROUP SUNSHINE (727-325-5843)

Listing Agent: Troy Funk (941-241-3850)

Remarks: Welcome to this stunning 5-bedroom, 5-bathroom home, where comfort, style, and adventure come together in one exceptional property. Designed with both relaxation and entertaining in mind, this spacious home features an open-concept kitchen that flows seamlessly into the inviting family room and out to a covered patio. Perfect for hosting gatherings or enjoying Florida’s beautiful weather. Upstairs, you’ll find two luxurious owner’s suites along with a cozy loft area, offering ample space for rest and privacy. Every detail of this home is crafted to create unforgettable experiences for family and guests alike. Located in the highly sought-after Storey Lake Resort, residents and guests enjoy access to resort-style amenities including a sparkling pool, golf, fitness center, and clubhouse. Just 12 minutes from Walt Disney World Resort, this property is perfectly positioned in a prime short-term rental community, making it an outstanding investment opportunity or dream vacation home.

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

Listing Agent: Nayi Torres (407-720-9585)

Remarks: 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: 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)