Homes for Sale Near Osceola High School in Kissimmee - 154 homes

Remarks: 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: Under contract-accepting backup offers. Rare Find in Adriane Park! Located in highly sought-after community of only 55 homes, known for its peaceful setting, spacious lots, and convenient location. This beautifully maintained 4-bedroom, 3 full bathroom home offers 2,444 heated square feet with a functional 3-way split floor plan. As you enter, you are welcomed by a spacious living and dining room featuring crown molding, chair rail accents, custom drapes, soaring 10-foot ceilings, and an abundance of natural light from four skylights throughout the home. The dining room connects conveniently to the kitchen through a charming swinging door. The spacious kitchen features granite countertops, a breakfast bar, dinette area, skylight, and plenty of storage space. Matching GE Stainless appliances. The kitchen opens to the inviting family room with a cozy wood-burning fireplace and French doors leading to the oversized screened lanai. Privately situated off the family room, the primary suite offers French door access, a walk-in closet, and an ensuite bathroom complete with a jacuzzi tub, separate shower stall, and private water closet. Bedrooms two and three are located on the opposite side of the home and share a spacious hall bath with dual sinks and a tub/shower combination with direct access to the lanai — already perfectly set up for adding a future pool. The 4th bedroom is conveniently located near the kitchen and offers ensuite access to the 3rd full bathroom, making it an ideal setup for guests, extended family, or a private home office. Step outside and enjoy the impressive 10x40 screened lanai overlooking the spacious backyard and peaceful pond view. Part of the lanai is covered, creating the perfect relaxing space, while the screened area offers an ideal setup for grilling and enjoying beautiful evening sunsets. Additional updates and features include: • Replumbed in 2023 • New toilets in 2023 • Interior painted with Sherwin-Williams Super Paint • Roof replaced in 2015 • Water heater replaced in 2017 • Sprinkler system • Intercom system • 1-year home buyer’s warranty included for added peace of mind. Corrugated metal storm panels included with the home. Equip with flood lights on all 4 corners. Low HOA fees of only $220 semiannually and NO CDD. Conveniently located near Osceola Hospital, Downtown Kissimmee, and the Florida's Turnpike. Ready to call this your new home? Call today to schedule your private showing!

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

Listing Agent: Janet Mcquagge (407-927-7399)

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 MVP (800-896-8790)

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

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: One or more photo(s) has been virtually staged. Price Reduced in the gated Tapestry community. This move-in ready 4-bedroom, 3.5-bath home offers over 2,300 square feet of stylish and functional living space with a bright open-concept layout designed for entertaining and everyday comfort. The spacious kitchen features granite countertops, stainless steel appliances, modern cabinetry, and a large center island that flows seamlessly into the dining and living areas. Upstairs, the private primary suite includes a walk-in closet and ensuite bath with dual vanities and a spacious shower. A versatile loft and additional bedrooms provide flexible space for a home office, media room, play area, or guest accommodations. Enjoy indoor-outdoor living with a covered rear porch and fully fenced backyard perfect for relaxing or weekend gatherings. Residents enjoy resort-style amenities including a clubhouse, pool, fitness center, sidewalks, and 24-hour gated entry. Conveniently located near shopping, dining, major highways, Orlando International Airport, and Orlando attractions. Now offered at an improved price schedule your private showing today.

Listing is courtesy of: AGG REALTY & MANAGEMENT LLC (407-267-7926)

Listing Agent: Amar Guemraoui (407-267-7926)

Remarks: One or more photo(s) has been virtually staged. Welcome to 3463 Forest Ridge Ln, located in the quiet gated community of Crestwood. This spacious 4-bedroom, 3.5-bath home with a 3-car garage offers over 3,800 square feet of thoughtfully designed living space, combining comfort, privacy, and an unbeatable Central Florida location close to shopping, dining, schools, and world-famous attractions. Designed for comfortable everyday living and entertaining, the home features expansive living spaces, a large kitchen with rich wood cabinetry, center island, pantry, breakfast nook, and a light-filled family room. The screened pool area provides the perfect private retreat for enjoying the Florida lifestyle year-round. The functional floor plan includes a designated office/den on the first floor, a convenient downstairs guest bedroom with its own en suite bath, generous living and dining areas, and a spacious primary suite featuring dual walk-in closets, double vanities, and a garden tub. The home is also ideally positioned near the community playground and pool area, offering convenient access to neighborhood amenities. major improvements provide peace of mind, including a new roof installed in 2021, two HVAC systems installed less than three years ago, a fairly new water heater and pool pump. Conveniently located near The Loop, Walt Disney World Resort, SeaWorld Orlando, Universal Orlando Resort, and Orlando International Airport, this home combines convenience, comfort, and value in one exceptional opportunity.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: Motivated Seller** Back on the market with the Backyard renovation buyers asked for, you won’t want to miss this. Completely transformed back yard oasis, this entire oversized .44 acre lots trees have been completely removed, grinded down and complimented with fresh Sod. We’ve maintained a Privacy border and a Brand New Double Gate Fence, a Brand New Deck/Pergola for entertaining along with a complete pool resurface, 2026 Pool Screen, 2025 roof, 2026 garage door, 2024 AC all with the beautifully remodeled interior, its truly a dream home! Tucked away in the highly sought-after Cross roads of Kings Highway and Neptune, The CDD free and a low HOA community of Harbour Oaks. This fully renovated 4-bedroom, 2-bath residence redefines everyday living with its blend of sophistication and serenity. Step inside to discover 2,369 sq. ft. of open-concept design where every finish has been thoughtfully curated. Featuring a full sized Laundry/Utility room, Wide-plank luxury vinyl floors, a Statement fireplace is the heart of the home, many closets through out. The chef-inspired kitchen featuring 36” soft-close solid wood cabinetry, stylish quartz countertops, and top-of-the-line Energy Star stainless steel appliances. Whether preparing a quiet breakfast or entertaining friends, this space is both functional and breathtaking. Retreat to the spa-inspired marble floor bathrooms, your serene fully screened in pool/patio or to your oversized two car garage that includes screened in sliders for your comfort. LOCATION LOCATION LOCATION, you can’t beat it as is considering its proximity to downtown Kissimmee, 30 mins from downtown Orlando, direct access to 1-4 & turnpike, state road 192, shopping, restaurants, lakes, parks and more and its soon to come developments (including Osceola community park, Osceola Metro Lagoon , Ovation Development and a lot more) within a couple miles this home makes it truly a forever home

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Rene Droz, Iii (407-484-8786)

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: CHARMING DOWNTOWN KISSIMMEE HOME WITH MODERN UPDATES,FRESH INTERIOR PAINT & CLASSIC CURB APPEAL WELCOME TO THIS BEAUTIFULLY MAINTAINED 3-BEDROOM, 2-BATHROOM HOME IDEALLY LOCATED IN THE HEART OF DOWNTOWN KISSIMMEE, JUST MINUTES FROM SHOPPING, RESTAURANTS, AND PUBLIC TRANSPORTATION. INSIDE, YOU’LL FIND A SPACIOUS GREAT ROOM, WELL APPOINTED KITCHEN AND BATHROOMS. OFFERING MODERN COMFORT WITH TIMELESS STYLE. THE LARGE KITCHEN AND DINETTE AREA ARE PERFECT FOR EVERYDAY LIVING AND ENTERTAINING, COMPLETE WITH A LARGE PANTRY AND A CONVENIENT INSIDE LAUNDRY ROOM. STEP OUTSIDE AND ENJOY THE HOME’S CLASSIC CHARM WITH A COVERED FRONT PORCH WITH RAILING OVERLOOKS A LOVELY PICKET FENCE, CREATING A WARM AND WELCOMING FIRST IMPRESSION. ADDITIONAL FEATURES INCLUDE A 2-CAR CARPORT AND A 10X12 STORAGE SHED WITH ELECTRIC, IDEAL FOR TOOLS, HOBBIES, OR EXTRA STORAGE. MAJOR UPDATES INCLUDE A BRAND-NEW ROOF (2025), GIVING PEACE OF MIND TO THE NEXT OWNER. THIS MOVE-IN-READY HOME BLENDS LOCATION, SPACE, AND CHARACTER. WHAT AN EXCELLENT OPPORTUNITY TO OWN A WELL MAINTAINED PROPERTY RIGHT IN DOWNTOWN KISSIMMEE.

Listing is courtesy of: GOODWIN REALTY & ASSOCIATES, INC (407-846-2787)

Listing Agent: Linda Goodwin-Nichols (407-908-0320)

Remarks: Wonderful unit located in a perfect community with amenities including clubhouse, gym, tennis court and swimming pools. Great location! Just Minutes to Disney World, Universal Studios, Sea World and Orlando International Airport. Near to local transportation, schools and The Loop Mall with 70 Stores, 15 Restaurants and Regal Cinema 16. Unit is located on the ground floor for better privacy. Each of the 2 spacious bedrooms has a bath & walk in closet, . Fully Equipped. All Appliances Included The unit also has a laundry room (washer and dryer included). Don´t miss the opportunity!

Listing is courtesy of: ALTIS REALTY (407-401-7447)

Listing Agent: Alicia Casal (407-401-7447)

Remarks: Spacious 4-bedroom, 3-bath single-family home on a generous 0.31-acre corner lot with no HOA! This versatile property offers an ideal layout with an eat-in kitchen, inside laundry, and a welcoming front bonus/sitting room perfect for a home office, reading area, or flex space.The split-style floor plan provides comfortable living for multi-generational households, or rental opportunities. Located within a block away from AdventHealth, making it especially appealing for healthcare professionals, traveling nurses, or long-term rental potential. Conveniently close to shopping, dining, and everyday amenities. Zoned for professional office use, offering rare flexibility for buyers seeking a live/work opportunity, small business location, or future investment potential. A unique opportunity for first-time buyers, investors, or entrepreneurs looking for space, location, and versatility.

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

Listing Agent: Carlethia Burnette (407-970-7902)

Remarks: Welcome to this spacious 4-bedroom, 2-bath single-family home featuring a beautiful saltwater pool, located in the desirable Fortune Lakes community of Kissimmee. Built in 2003, this well-maintained property offers 2,085 sq ft of living space on an 8,233 sq ft lot, providing comfort, privacy, and convenience in a prime Central Florida location. This home features a split floor plan, generous living areas, and a layout ideal for both everyday living and entertaining. Recent upgrades include central A/C (2020), water heater (2024), new kitchen appliances, updated kitchen countertops, new carpet and flooring, and a wireless alarm system on all doors and windows. The home also offers a new roof, recently resurfaced pool and pool deck, an upgraded screened enclosure, and a saltwater pool system with a pool pump replaced approximately 2–3 years ago. Exterior features include a 2-car garage, stucco finish, and composition shingle roofing. Located just minutes from major highways, shopping, dining, schools, and medical facilities, this home provides excellent access to everything Kissimmee and Orlando have it. The Fortune Lakes/Remington area is known for its well-kept surroundings, nearby golf options, and strong community appeal. Original Owners.

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

Listing Agent: Jackie San Pedro (407-346-8922)

Remarks: Discover your own private retreat in the heart of Poinciana! This beautifully maintained 3-bedroom, 2-bath pool home with a brand-new roof and floor offers nearly 1,900 sq. ft. of comfortable living space on a generous 0.21-acre lot. Inside, you’ll find an inviting open floor plan, tile flooring throughout, a bright kitchen with abundant cabinetry, and a spacious living area ideal for entertaining. The split bedroom layout provides excellent privacy, while the screened-in pool and outdoor deck give you a peaceful setting for both relaxation and gatherings. Additional highlights include a detached 2-car garage, a fully chain-link fenced backyard, and no CDD fees. Nestled on a quiet cul-de-sac with desirable north-facing frontage, this home is just minutes from schools, parks, and shopping. Located within the Association of Poinciana Villages, the community features a low monthly HOA. Don’t miss this move-in-ready home with incredible potential—schedule your showing today!

Listing is courtesy of: LAND & HOME ASSET LLC (407-417-1629)

Listing Agent: Amy Rivers (407-417-1629)

Remarks: This beautifully maintained first-floor three-bedroom, two-bathroom condo in Kissimmee offers an exceptional opportunity for homeowners and investors alike. Conveniently located near major shopping centers, restaurants, and entertainment, and just minutes from Walt Disney World Resort, this property combines comfort, convenience, and lifestyle. Situated within a secure gated community, residents enjoy peace of mind along with amenities designed for relaxation and enjoyment. The community features elevator access to all floors and a beautifully designed resort-style pool overlooking the lake, creating the perfect setting to unwind. Located on the first floor for added convenience and easy access, this condo is ideal for families, professionals, or investors seeking strong rental potential in one of Central Florida’s most desirable areas.

Listing is courtesy of: ALTIS REALTY (407-401-7447)

Listing Agent: Reynaldo Izaguirre, Pa (407-683-0998)

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: 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: Under contract-accepting backup offers. Welcome to Preserve at Tapestry, one of Kissimmee’s most sought-after communities, where lifestyle, location, and convenience come together. This beautifully maintained Somerset Model by Beazer Homes (2014) offers 4 bedrooms, 2.5 bathrooms, and 2,338 sq ft of thoughtfully designed living space—perfect for both everyday living and entertaining. From the moment you arrive, you’ll notice the attention to detail with a freshly painted exterior (2026), a newly painted and sealed paver driveway and entryway, and the added peace of mind of a brand-new roof (2026)—a major upgrade that adds both value and longevity. Step inside to an inviting open-concept floor plan featuring tile flooring throughout the entire first level, offering a clean, modern flow. The layout is both functional and versatile, highlighted by a separate formal dining room and a spacious living area that seamlessly connects to the kitchen. The kitchen is designed for both daily living and entertaining, featuring: Granite countertops Stainless steel appliances Ample cabinetry and storage Generous counter space for meal prep Side buffet area Large corner pantry Upstairs, you’ll find luxury plank wood vinyl flooring throughout, enhancing both durability and style. The second floor offers three well-sized secondary bedrooms and a full bath, while the owner’s suite is privately positioned in the corner for added comfort. The owner’s retreat features: Spacious layout Dual sink vanity Garden tub Separate walk-in shower And one of the standout features of this model: a HUGE walk-in closet, among the largest in Beazer’s floor plans Additional upgrades include an extra-large water heater, providing enhanced capacity and efficiency for a growing household. Step outside and start envisioning your future outdoor oasis. The backyard offers endless possibilities: Expand the existing covered lanai Design your own custom pool retreat Enjoy evenings around the existing fire pit Mature fruit trees and bamboo create a private and serene atmosphere Located just minutes from The Loop Shopping District, Walt Disney World, major restaurants and entertainment, as well as convenient access to Osceola Pkwy, SR 417, Florida’s Turnpike, and Orlando International Airport (MCO)—this home offers the perfect blend of accessibility and lifestyle. Residents of Preserve at Tapestry enjoy resort-style amenities, including a clubhouse, pool, walking trails, park and playground. This is a rare opportunity to own a move-in ready home with major upgrades already completed, in one of Kissimmee’s most desirable communities.

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

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

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

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

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

Remarks: Under contract-accepting backup offers. 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 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. HOA includes lawn maintenance. Schedule your showing today. The home may be sold furnished.

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

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