Homes for Sale Near Osceola High School in Kissimmee - 94 homes

Remarks: 3-bedroom, 2-bathroom home offering 1,592 square feet of comfortable living space in the heart of Kissimmee. This property features a functional layout with spacious living area.The kitchen flows seamlessly into the main living space, making it ideal for both everyday living and entertaining. Situated in a convenient location near shopping, dining, schools, medical facilities, and major roadways including Osceola Parkway, US-192, and Florida’s Turnpike. Easy access to Orlando attractions and employment centers. Major update: Roof installed in 2021, providing peace of mind and long-term value. Whether you're a first-time buyer, downsizing, or seeking an investment opportunity, this property offers solid value in a central location. Schedule your private showing today.

Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)

Listing Agent: Hector Pagan, Pa (407-791-4858)

Remarks: Charming and beautifully positioned 3 bedrooms, 2 bathrooms ground floor unit with peaceful garden view and resort style living at your doorstep. Just steps away from the sparkling community pool and gazebo, this home offers the perfect blend of comfort and convenience. Enjoy a bright, open layout filled with lots of light, a cozy back patio ideal for relaxing mornings, entertaining or unwinding evenings. A well kept home, with a lot of upgrades and all stainless steel appliances. Nestled in a prime location close to shopping, dining and major roadways. This is an exceptional opportunity for homeowners or investors seeking the Florida lifestyle at its best.

Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)

Listing Agent: Claudette Banton Dennis (347-876-1091)

Remarks: Stunning 2-bedroom, 2-bath condominium with 1-car garage! This beautifully maintained home offers a bright and airy open-concept design, perfect for both everyday living and entertaining, ideally located next to the community clubhouse, offering easy access to amenities and enhancing your lifestyle. Enjoy two spacious master suites, each featuring its own walk-in closet, providing comfort, privacy, and flexibility. Elegant laminate flooring flows seamlessly throughout the entire home, creating a modern and cohesive feel. The kitchen is equipped with a gas stove, perfect for those who love to cook, and features recent upgrades including a brand-new refrigerator (2025), new microwave (2025), and new garbage disposal (2025). The A/C unit was replaced in 2019. Additional highlights include a convenient inside laundry room and a well-designed layout that maximizes both space and functionality. This move-in ready condo offers the perfect combination of style, comfort, and low-maintenance living—a true must-see!

Listing is courtesy of: VENTURE HOME REALTY (407-587-0076)

Listing Agent: Reyna Quezada (407-780-0426)

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: Short Sale. FOR SALE - SHORT SALE - 4 Bedroom/ 2 Bath 2400 sq.ft. Single Family Home on a quiet street in the community of Poinciana. The home is spacious and offers an open floor plan. WI-FI is included in the HOA fees. The Living Room, Dining Room and Kitchen combo are ideal for entertaining. The kitchen has an island which is perfect for serving food or sitting around to eat a snack. The range, range hood, and dishwasher come with the home. The Primary Bedroom is generously sized with a well-equipped Primary Bathroom. The home features several storage closets and an inside laundry room. The home comes with solar panels and an unfinished pool. Poinciana is located on the outskirts of Kissimmee and Orlando and provides many activities for today's family. The Poinciana Community Park has playgrounds, picnic tables, sports fields and offers seasonal festivities and outdoor movie nights. The Poinciana Library offers reading programs, story time for minors, workshops for the adults, and events for all ages. For nature lovers, Poinciana is home to the Disney Wilderness Preserve which is a 12,000 acre preserve with hiking trails and areas to see Florida's native birds and flowers. Let's not forget this home is only a half hour from DISNEYWORLD!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Linda Andre (863-852-5747)

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: $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: 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: 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: 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: 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: Under contract-accepting backup offers. 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: 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: 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)