Homes for Sale Near Osceola High School in Kissimmee - 149 homes

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Price Improvement! Welcome to this beautifully maintained condo for sale in the desirable gated community of Flora Ridge in Kissimmee. Located on the third floor with convenient elevator access, this residence offers comfort, space, and functionality in a prime location. As soon as you walk in, you’ll be impressed by the open and airy layout, where the living room and dining room flow seamlessly together — perfect for entertaining or relaxing at home. Natural light fills the space, creating a warm and inviting atmosphere. The kitchen offers ample cabinet storage, laminate countertops, and sleek stainless steel appliances, making it both practical and stylish. Just off the kitchen, you’ll find a dedicated laundry room complete with washer and dryer for added convenience. The main bedroom suite is generously sized and filled with natural light. A unique and versatile adjacent room connected to the primary suite can be used as a home office, nursery, sitting room, or even your dream custom closet space. The main bathroom is thoughtfully designed with dual vanity sinks, a walk-in shower with glass doors, a walk-in closet, and a private enclosed toilet room. On the opposite side of the condo, you’ll find two additional bedrooms with a full bathroom in between. The shared bathroom features a bathtub, ideal for guests or family. Bedroom two includes a built-in closet, while bedroom three offers a spacious walk-in closet. Step outside onto the private balcony, the perfect place to unwind in the evenings and enjoy Florida’s beautiful weather. Flora Ridge is a gated community in Kissimmee known for its tranquil, park-like setting and well-maintained grounds. Residents enjoy: Secure gated access for peace of mind, One assigned carport parking, right for two vehicles, Additional community parking spaces for visitors, Assigned overnight guest parking available for visitors, Lush landscaping and garden and water views throughout the neighborhood. Close to the Loop, Turnpike, Access to 417 and the Airport.

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

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

Remarks: Welcome to Regal Cove – Modern Luxury Meets Country Charm! Imagine living in the exclusive, gated community of Regal Cove, where this fully renovated custom home offers both elegance and privacy. Set on nearly half an acre (.49), this residence boasts one of the largest private screened lap pools in the area with a heated spa—perfect for entertaining or relaxing year-round. From the moment you arrive, the long driveway and welcoming front porch set the tone for comfort and sophistication. Step inside the brand-new modern renovation featuring an open concept design and tasteful finishes throughout. The spacious family room is highlighted by an elegant tile accent wall with an electric fireplace and French doors overlooking the pool and mature tree views. The gourmet kitchen is a showpiece with a waterfall island, drop-down range system, top-tier appliances, custom cabinetry, built-in double oven/microwave, wine cooler, and coffee station. A true chef’s delight, it’s designed for hosting family and friends with ease. The primary suite, located on the first floor, offers a stunning walk-in closet and a spa-like bathroom with a freestanding soaking tub, double vanities, separate water closet, and an oversized double-head shower. Upstairs, you’ll find four additional bedrooms with a sleek glass panel railing system, a bonus storage room, and two beautifully renovated Jack & Jill bathrooms. Adding incredible flexibility, a three-car garage with extended roofline includes a private full apartment above the garage with a bedroom, bathroom, kitchen, and living/dining area. Perfect as a guest house, or secondary suite. Outdoor living shines with two covered patio areas, French impact windows, and the expansive screened pool deck. With only $400/Quarter HOA fees, Regal Cove provides an upscale yet affordable lifestyle, ideally located near Lake Tohopekaliga with a public boat ramp less than a minute away. You’ll also enjoy easy access to the FL Turnpike, Publix, Walmart, and all of Kissimmee’s conveniences. This is a rare opportunity to own a modern, custom-renovated pool home with an in-law suite in one of Kissimmee’s most desirable gated communities. Schedule your private showing today and experience the perfect blend of country charm and modern luxury.

Listing is courtesy of: FIERCE REALTY (407-758-5179)

Listing Agent: Rachel Coolidge (207-522-0838)

Remarks: LOCATION! CONVENIENCE! SECURITY! Move-in ready and updated 4-bedroom, 3-bath townhouse in Venetian Bay Villages is ideal as a primary home, vacation retreat, or income-producing investment. The spacious layout features a first-floor master suite with a jetted tub, updated kitchen and baths, and a 2018 roof. Enjoy 24/7 guard-gated security and resort-style amenities, including 4 pools, fitness center, spa, clubhouse, theater, game room, playgrounds, tennis, basketball, volleyball, and BBQ areas. Perfectly located just minutes from Disney, Universal, shopping, dining, and major highways, this turnkey property offers unmatched comfort, convenience, and value. Property is being sold fully furnished. Zoned for short-term rental, perfect as an Airbnb investment or primary residence.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Evelyn Lopez Correa (787-475-2292)

Remarks: Welcome to this 2-bedroom, 2-bath with a bonus room. This home is in a well located community near shopping, dining, and hospitals, and major roads. This property offers a great layout and plenty of potential for someone looking for adding their own personal touch. Good opportunity for buyers who want to update and make it their own. With its convenient location and solid floor plan, this home is a great option for anyone looking for value and future potential.

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-870-8388)

Listing Agent: Diego Francisco (216-407-6788)

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: THE EXPERTS TEAM REALTY INC (407-674-7994)

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

Remarks: Located in the sought-after Tapestry community, this beautiful 3-bedroom, 2.5-bath townhome offers a spacious and inviting layout with numerous upgrades throughout. The open-concept design features a large kitchen with granite countertops, stainless steel appliances, and ample cabinetry, seamlessly connected to the dining and living areas—ideal for entertaining and everyday living. High ceilings enhance the natural light and create an airy feel throughout the home. All bedrooms are located upstairs, including the primary suite, along with two additional bedrooms and a conveniently positioned laundry room. The bedrooms are generously sized and offer plenty of storage space and large windows. All appliances are included. Conveniently situated near major roads, shopping, dining, and everyday conveniences. A great opportunity to own in one of the area’s most desirable communities!

Listing is courtesy of: ORLANDO BROTHERS REAL ESTATE LLC (407-925-2221)

Listing Agent: Iluska Kruse (407-925-2221)

Remarks: BEAUTIFUL AND CENTRALLY LOCATED TOWNHOME!!!! This property offers a spacious and functional layout, ideal for homeowners or investors. Its prime location provides direct access to major roads such as John Young Parkway, Osceola Parkway, and US-192, allowing for quick connectivity to Orlando, employment centers, and world-famous attractions. Just minutes from The Loop, where you’ll find a wide variety of restaurants, shopping, entertainment, and everyday conveniences. Surrounded by supermarkets, dining options, and schools, this property perfectly combines comfort, location, and convenience. The seller is motivated and willing to contribute toward closing costs, making this an excellent opportunity for buyers. A truly exceptional opportunity to live or invest in the heart of Kissimmee!

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

Listing Agent: Lisbeth Hernandez Gil (786-498-9363)

Remarks: Welcome to resort-style living at Tapestry in Kissimmee! This beautiful 3-bedroom, 2 full bathrooms + 1 half bath townhouse offers a modern open floor plan designed for comfort and entertaining. The home features a spacious kitchen with stainless steel appliances, generous living and dining areas, a 2-car garage, and a private second-floor balcony perfect for relaxing. Located inside the highly desirable gated community of Tapestry, residents enjoy access to an incredible clubhouse with luxury amenities including a resort-style pool, fitness center, splash area, playgrounds, walking trails, sports courts, and beautifully maintained common areas. Conveniently located near The Loop shopping center, restaurants, major highways, Orlando attractions, and Disney parks. A perfect opportunity for primary residence, vacation home, or investment property!

Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)

Listing Agent: Alex Leonardo (407-832-2946)

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

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

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

Remarks: Under contract-accepting backup offers. Just Listed! Check out this fantastic pool home with a 3 car garage, perfectly tucked away in a quiet neighborhood yet close to everything Kissimmee has to provide. From the moment you step inside, you’ll love the floor plan with a direct view to the gorgeous pool! Ceramic tile flooring flows through the main living areas ideal for both everyday living and entertaining, while plush carpet in the bedrooms adds comfort underfoot. The floor plan includes an eat-in kitchen, family room, formal dining room, formal living room, and outdoor living space. The primary suite has 2 closets, sliding doors to the pool area, and its own ensuite bathroom with double vanities and step-in shower. Step through sliding glass doors to the covered lanai, the perfect place to unwind with a good book, host friends, or watch your family play in the fenced backyard that offers space to play or simply relax in the Florida sunshine. Step into your own private paradise with a resort-style backyard designed for both relaxation and entertaining. The stunning resort style pool area is surrounded by lush tropical landscaping that creates a peaceful, vacation-like setting right at home. Premium turf adds beauty and functionality with a clean, manicured look year-round while minimizing maintenance and mud. Whether you’re hosting friends, enjoying family time, or unwinding after a long day, this outdoor oasis offers the perfect blend of luxury, comfort, and low-maintenance living. Recent updates and upgrades include a New roof, New AC, New fresh paint, New bathroom sinks and plumbing fixtures, Kitchen cabinet refresh, Premium turf in the backyard, New pool pump, and much more! You’ll appreciate the convenience of a fantastic central location - close to shopping, dining, schools, and medical facilities! Don’t miss the chance to make this Kissimmee home your own. Schedule your private showing today and start living the lifestyle you’ve been waiting for!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Christina Moore (863-430-8517)

Remarks: Discover this beautifully renovated home, perfect for living or investing, 2 Bedrooms | 1 Bath, Spacious Living & Dining Room. Brand-new kitchen with granite countertops, Fresh interior & exterior paint. Charming front & Back porch to enjoy your mornings. Elegant pavers! New metal roof! NO HOA! Prime opportunity in Kissimmee? Ideal for first-time buyers or investors. Schedule your private showing today! Wheel Chair Ramp, Dead-End. Community Allow 1 RV at the property!

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

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

Remarks: Under contract-accepting backup offers. A rare opportunity part of historic Downtown Kissimmee with NO HOA. This charming well kept 2 bedroom 2 bath property is on a fully fenced lot with a huge extended Driveway that easily fits multiple vehicles meaning bring your boat, trailer, or work trucks with no restrictions. NO HOA! Great starter home that checks all the boxes. Roof was replaced in 2019 and air conditioning unit was replaced in 2025. Location is everything, and this one is unbeatable. Just a few blocks from Downtown Kissimmee, you’re minutes from Lake Toho's scenic waterfront, Kissimmee Lakefront Park, restaurants, Broadway Pizza, boutiques, the Kissimmee Valley Farmers Market, year-round community events, seasonal festivities, bus depot and Sun Rail access for easy commuting. Easy access to Disney, major roads and highways, the Turnpike and the hospital is just a few block away. Opportunities like this in Downtown Kissimmee don’t come around often so HURRY before it's gone!

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

Listing Agent: Lucy Rivera (407-922-1953)

Remarks: THIS HOME IS A MUST SEE!!! Welcome to this stunning 4-bedroom, 3.5-bathroom home, ideally located in the sought-after Solara Resort in Kissimmee. Whether you're looking for a full-time residence or a vacation home investment, this property offers the perfect blend of relaxation and convenience. Situated just off US-192, with quick access to I-4 and US-27, you’re only 8 miles from world-class theme parks and just a short commute to the famous attractions of the Orlando area, including local beaches. Enjoy easy access to premier shopping and dining options along International Drive or at the Prime Outlet Mall. The Solara Resort community offers an unparalleled resort-style living experience with amenities that include an on-site restaurant, coffee bar, beach-style pool, pool bar, fitness center, basketball court, soccer field, volleyball court, gaming stations, sports simulator, yoga lawn, playground, splash pad, water slides, and even a Flowrider sea wave simulator – there's something for everyone! Inside, the home has been beautifully decorated and furnished by professionals with an open floor plan that is perfect for entertaining. The spacious kitchen boasts granite countertops and stainless-steel appliances, making meal prep a true pleasure. The upstairs loft is a media dream, providing ample space for movie nights or relaxation. The dining area seamlessly flows into the outdoor space through sliding doors, leading to your own private pool—ideal for extending your entertainment space. Don’t miss out on this incredible opportunity to own a piece of paradise. Call today and schedule your showing at your convenience!

Listing is courtesy of: LEGACY PLUS REALTY (407-992-2268)

Listing Agent: Solon Potenciano Silva (407-760-5141)

Remarks: INVESTOR OPPORTUNITY! HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

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

Remarks: INVESTOR OPPORTUNITY! HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

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

Remarks: Under contract-accepting backup offers. INVESTOR OPPORTUNITY! HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

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

Remarks: ?? INVESTOR OPPORTUNITY! ?? HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

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

Remarks: ?? INVESTOR OPPORTUNITY! ?? HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

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

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

Remarks: Under contract-accepting backup offers. Welcome to the newly renovated 2628 Milton Ave, a beautifully updated block home located in the established community of Kissimmee Highlands! Situated on an oversized lot just shy of ¼ acre with NO HOA, this move-in ready property offers the perfect combination of modern upgrades, functionality, and value. Completely renovated in April 2026, this home has undergone an extensive transformation from top to bottom. Major improvements include a BRAND NEW ROOF WITH ALL NEW PLYWOOD, COMPLETE ELECTRICAL REWIRE, NEW WATER HEATER, NEW FLOORING THROUGHOUT, FULLY REDESIGNED KITCHEN, BRAND NEW APPLIANCE PACKAGE, UPDATED BATHROOMS, RECESSED LIGHTING, NEW FIXTURES, NEW INTERIOR DOORS, TRIM AND BASEBOARDS, FRESH INTERIOR AND EXTERIOR PAINT, AND NEW TEXTURE ON ALL WALLS AND CEILINGS. The HVAC system has also been PROFESSIONALLY CLEANED AND SERVICED, along with the installation of a NEW THERMOSTAT for added comfort and efficiency. Conveniently located near major roadways, shopping, dining, schools, and everyday conveniences, this property offers outstanding accessibility while still providing the benefit of a larger lot size that is increasingly difficult to find. The expansive yard offers endless potential for outdoor entertaining, storage, gardening, or future additions. This area also allows for ADUs (Accessory Dwelling Units), and the oversized lot provides excellent potential for future expansion, guest quarters, rental income opportunities, or multi-generational living. With all the major upgrades already completed, this home is ideal for first-time buyers, downsizers, investors, or buyers seeking additional long-term upside potential. 2628 Milton Ave is the perfect blend of classic construction and modern renovation — ready for its next owner to move right in and enjoy.

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Alex Vazquez (407-270-6841)

Remarks: One or more photo(s) has been virtually staged. Beautiful 3- bedrooms and 2- bathrooms home in the heart of Kissimmee with NO HOA! Conveniently located near Downtown Kissimmee shopping, restaurants, schools major highways,and just minutes from Kissimmee Lakefront Park. This home offers comfort,space,and the freedom of no HOA restrictions. Perdect for first-time buyers or anyone looking for a great location in Central Florida!

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

Listing Agent: Susana Moor (407-744-5801)