Homes for Sale Near Osceola High School in Kissimmee - 142 homes

Remarks: Under contract-accepting backup offers. Welcome to refined lakefront living in the sought-after Regal Bay community on the shores of Lake Tohopekaliga. Perfectly positioned at 1475 Riviera Drive, this exceptional 3-bedroom, 2.5-bath residence offers a rare combination of panoramic water views, private boating access, and tranquil outdoor living—and is being sold furnished for a seamless move-in experience. From the moment you arrive, you’re greeted by a serene front porch overlooking the sparkling waters of Lake Toho, setting the tone for the peaceful lifestyle this home delivers. Inside, the layout is designed to capture water views from multiple vantage points, creating a seamless connection between indoor and outdoor living. The rear of the home opens to a spacious porch with stunning, unobstructed lake views—ideal for morning coffee, evening sunsets, or entertaining guests. Boating enthusiasts will appreciate the private dock and boat lift, providing direct access to this highly desirable, skiable lake known for its world-class fishing and recreational boating. Additional highlights include a charming secondary porch off the dining room, perfect for quiet moments, along with well-appointed living spaces that balance comfort and functionality. Whether you’re searching for a full-time residence or a turnkey waterfront retreat, this property offers a unique opportunity to enjoy true Florida lakefront living with both sunrise and sunset views over Lake Toho.

Listing is courtesy of: TOHO REALTY GROUP, LLC (407-437-2893)

Listing Agent: Kerriann Sullivan (407-437-2893)

Remarks: This is the kind of home multigenerational buyers wait for. 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 offers a rare setup designed for living together without giving up privacy, comfort, or independence. With two full kitchens, two laundry areas, two separate two-car garages, and three full baths, this property functions beautifully for extended families, in-laws, adult children, long-term guests, or anyone needing flexible living under one roof. A spacious shared living room creates a natural central gathering space, while the home splits into two distinct wings. One side features two bedrooms, two full baths, a full kitchen, its own family room, and access to the oversized screened lanai and fully fenced backyard. The other side offers a spacious primary suite with ensuite bath, a separate family room, a second full kitchen with pantry, and its own attached two-car garage. A paid-off solar system adds even more value from day one, helping keep electric costs down. With no HOA, plenty of room to spread out, and a location near East Lake Toho, Kissimmee Lakefront Park, Shingle Creek Regional Park, Downtown Kissimmee, St. Cloud, and the theme parks, this is a rare opportunity for buyers who need space, flexibility, and a home that truly supports the way modern families live.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Shawn Layton (321-514-8055)

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

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

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

Remarks: 4 bedroom 2 bath home in a gated community. Living/dining room, large kitchen with eating space. 2 car garage. Pond view from the back of the house and conservation view from in part of the front.

Listing is courtesy of: REALTY SERVICES OF AMERICA (407-319-4113)

Listing Agent: Edgar Gonzalez (407-319-4113)

Remarks: Under contract-accepting backup offers. 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: INVESTORS OPPORTUNITY !!!! TENANT OCCUPIED. Fully remodeled, this inviting single-family home at 709 S Dillingham Ave in Kissimmee is designed for comfort and flexibility. The thoughtfully updated interior offers modern finishes throughout, creating a fresh and welcoming feel from the moment you arrive. Ideal for multi-generational living, the home includes a private mother-in-law suite with 2 bedrooms and 1 bathroom, perfect for extended family or guests while still maintaining privacy or for a great rental income. Centrally located near downtown Kissimmee, shopping, dining, schools, and major roadways. Enjoy peace of mind with a beautifully updated home ready for its next chapter. A wonderful opportunity to settle into a space where everyone feels at home. Buyer to verify all measurements and information.

Listing is courtesy of: GPS PROPERTY GROUP INC. (407-439-2527)

Listing Agent: Abel Jimenez (407-452-4119)

Remarks: Experience stylish and comfortable living in this beautifully designed townhome located within the sought-after Tapestry community. Perfectly positioned at 2504 Fassona Drive, this residence offers convenient access to Central Florida’s major highways, shopping, dining, and top attractions. Featuring 3 spacious bedrooms, 2.5 bathrooms, a downstairs primary suite, and a screened lanai, this home blends functionality with modern elegance. Interior highlights include quartz countertops, expansive windows that fill the home with natural light, and sleek railing details that create an open and inviting atmosphere. Move-in ready and thoughtfully designed, residents also enjoy resort-style amenities including a fitness center, 24-hour security, and a guarded gated entrance.

Listing is courtesy of: THE AGENT, INC (407-278-7090)

Listing Agent: Maria Godoy (407-906-0112)

Remarks: Opportunity is knocking with this stunning property nestled within the highly sought-after Stonefield community in Hunter’s Creek. This is a rare chance to own a spacious, updated townhome with an ASSUMABLE FHA LOAN at an incredible 3.375 interest rate, a true game changer in today’s market! But wait that’s not all! This 2-bedroom, 2-bath home with a 1-car garage features three additional flex rooms, offering incredible versatility for your lifestyle. Whether you need a private home office, formal dining room, cozy den, or guest suite, this floor plan easily adapts to your needs. Enjoy the perks of modern living and energy efficiency with a paid off solar energy system providing substantial savings, plus a newer 2021 energy-efficient A/C unit. Inside, you’ll find tile and laminate flooring throughout, appliances and an interior laundry room with washer & dryer included along with built-in cabinetry for convenient storage. The primary suite offers abundant natural light, a spacious walk-in closet, private ensuite bathroom featuring double vanities and an oversized walk-in linen closet. Upstairs, you’ll discover two large bonus rooms perfect for an office, studio, guest quarters or extra storage that many homes lack. The second bedroom is located on the main floor across from the updated second bathroom, which, like the primary, features stone countertops and modern finishes. Stylish lighting fixtures throughout the home add a contemporary touch, making this property truly move-in ready. Residents of Stonefield enjoy a secure gated community with resort-style amenities, including resort style pool, clubhouse, fitness center, tennis courts, fishing dock and walking / biking trails surrounded by exotic landscaping. Located just 15 minutes from Disney, Universal, Orlando’s top attractions, 20 minutes from Orlando International Airport, hospitals, schools, medical offices, markets and steps from The Loop’s dining with plenty of shopping for everyday needs. This home perfectly blends convenience, comfort and lifestyle. Live a life of ease, style and abundance of opportunity.

Listing is courtesy of: LPT REALTY LLC (386-204-6398)

Listing Agent: Scarlett Napolitano (407-808-6757)

Remarks: This inviting 3-bedroom, 2-bath condo in Flora Ridge offers a bright and spacious layout designed for comfortable everyday living. The living and dining areas flow seamlessly into a screened-in balcony, while the kitchen features ample cabinet space and a practical layout. All three bedrooms are generously sized, with carpeted flooring for added comfort, and both bathrooms are tiled for easy maintenance. Located near the community pool and just minutes from shopping, dining, schools, and major roads, this condo offers convenience and a family-friendly environment in a well-maintained and secure gated community.

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

Listing Agent: Mariana Nossa (407-455-9565)

Remarks: Discover this spectacular residence located in the exclusive gated and guard-secured community of Tapestry in Kissimmee. Featuring 3 bedrooms, 2 bathrooms, and an office, this 1,706-square-foot home is designed for those seeking comfort, style, and a lifestyle filled with exceptional amenities. From the moment you enter, the home welcomes you with an open-concept layout, bright living spaces, and a seamless flow between the main living areas, creating the perfect setting for both everyday living and entertaining. The office offers a versatile space ideal for working from home, studying, or adapting to your personal needs. The spacious bedrooms provide comfort and privacy, while the contemporary finishes and functional design create a warm and inviting atmosphere throughout the home. Living in Tapestry means enjoying resort-style amenities designed for the entire family, including a beach-entry pool with cabanas, splash and recreational areas, a state-of-the-art fitness center with yoga and movement studio, an elegant clubhouse with catering kitchen for special events, outdoor terrace, sports courts, BBQ pavilions, dog park, and walking and biking trails. All of this is nestled within a private 24-hour guard-gated community, conveniently located near major highways, Orlando attractions, the airport, shopping, dining, and excellent schools. Whether you are searching for a primary residence, vacation home, or investment opportunity, this beautiful property offers an exceptional chance to experience the Florida lifestyle at its finest. Schedule your private showing and experience everything this beautiful home.

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

Listing Agent: Neyla Alvarez (407-780-8786)

Remarks: Welcome to this beautifully presented pool home in Kissimmee! This spacious residence showcases the kitchen featuring elegant gold fixtures and sleek stainless steel appliances, including a range, refrigerator, dishwasher, and microwave. Designed for both comfort and entertaining, the home offers a bright living room and a cozy dinette space. Enjoy the clean, modern feel of no carpet throughout, complemented by stylish flooring and ceiling fans in several rooms for added comfort. Both bathrooms have been tastefully updated, enhancing the home’s contemporary appeal. Step outside to a large screened-in patio overlooking a sparkling open-air pool—perfect for relaxing or hosting gatherings. The fully fenced backyard adds an extra layer of privacy, making this home a true retreat.***Home square footage, taxes, lot sizes, and schools; are to be independently verified.***

Listing is courtesy of: ALLEGIANT MANAGEMENT GROUP INC (407-557-3164)

Listing Agent: Elizabeth Santiago Moyet (321-231-2105)

Remarks: ATTENTION BUYERS: Primary residence, INVESTORS for Airbnb or short-term rentals. FIESTA KEY is a resort-style and peaceful living 24-gated community with an excellent location close to Disney parks, restaurants, shopping, schools, and more! This townhome has 3 bedrooms, 2 bathrooms, and the laundry upstairs for privacy. You will enjoy the first floor in an open floor plan, the living room, and the half bathroom. You will love the lanai for your morning coffee or to read a book. Kitchen appliances included. There is parking for 4 vehicles. Amenities: clubhouse, fitness center, tennis court, walking trails, walking distance to clubhouse, resort-style pool, and a 2nd. pool inside the gated community. Live free and unworried about outside maintenance because the HOA takes care of it: roof, painting, lawn, etc.

Listing is courtesy of: FLORIDA FANTASY REAL ESTATE INC (407-397-9039)

Listing Agent: Maribel Minarro (407-908-3522)

Remarks: Beautiful 2-Story Home in Gated Community – Great for Living, Vacation, or Rental Income This is a wonderful opportunity to own a fully furnished 2-story home located in a quiet, gated community with 24/7 security and great amenities. The home is in excellent condition and is currently being used as a short-term rental with a 5-star rating on Airbnb. It’s located in a very convenient area — just minutes away from Walmart, Disney parks, Highway 192, and Plaza del Sol. Whether you're looking for a permanent home, a vacation spot, or an investment property, this one offers a lot of value and flexibility. The home is already listed and performing well on Airbnb. If the buyer is interested, we’re happy to transfer the current and upcoming Airbnb bookings to make the transition smooth and help you start earning right away. Inside, the home is clean, spacious, and comes fully furnished, so it’s truly turn-key — ready for living or renting without any extra effort. The community offers plenty of amenities for guests and residents, including a swimming pool, clubhouse, gym, and more. It’s a safe, family-friendly neighborhood that’s also appealing to tourists due to its close proximity to major attractions. Whether you plan to live here full-time, use it as a vacation getaway, or continue running it as a short-term rental, this home is a smart choice in a great location.

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

Listing Agent: Juan Garcia Betancur (407-535-0909)

Remarks: LOCATION, LOCATION, LOCATION! This fantastic property features a 2025 NEW manufactured home and is truly ready for move-in! ?It boasts three spacious bedrooms and two comfortable full bathrooms. Enjoy the sleek look and easy maintenance vinyl flooring throughout the entire home. ?A sliding door from the living area leads out to a relaxing patio—perfect for hosting barbecues and spending quality time with family and friends. The home also includes a spacious living and dining area, an eating space in the kitchen, and all appliances are included. ?Recent updates include a new drain field. The home is centrally located with incredibly easy access to shopping, restaurants, and the Orlando International Airport. ?Schedule your showing today and make this beautiful home yours! The seller is highly motivated.

Listing is courtesy of: CENTRAL REALTY GROUP AND PROPERTIES (407-582-9011)

Listing Agent: Bernardino Castorani (407-582-9011)

Remarks: Welcome to this stunning move-in ready waterfront home! New Roof in January 2025! Nestled in highly sought-after gated community of Weston Reserve, and in a prime location in Kissimmee. Used as a second home, this impeccable 4-bedroom, 2-bath home offers a spacious open floor plan. Step inside to a bright foyer, high ceilings, and generously sized separate formal living room and dining room. The kitchen is both functional and welcoming, featuring 42” cabinetry with ample space, beautiful appliances, cozy breakfast nook, and openly leads to dining and family room – ideal for everyday living, hosting and entertaining. Sliding glass doors in both family room and primary suite open up to an oversized screened LANAI overlooking the beautiful pond and conservation area with serene atmosphere and no rear neighbors. The spacious primary suite boasts 2 walk-in closets, a peaceful retreat with private access to the patio and backyard—ideal for enjoying quiet mornings outdoors, and tranquil relaxation after a long day. The ensuite bathroom includes a beautifully tiled walk-in shower, a dual vanity with ample storage, and a huge spa tub. All 4 bedrooms, family room and Lanai has ceiling fans installed. Extended patio and backyard are ideal for BBQs, big family gatherings, and for little ones or pets to play around. Residents enjoy resort-style amenities, including a community pool, sand volleyball court, playground, BBQ area, and a private gated path access to Kissimmee Loop Trail, and the Shingle Creek Regional Trail. Located within close proximity to the Town Loop Shopping Center, this home provides unmatched convenience to restaurants, retails, gyms, supermarkets and everyday essentials. Conveniently located near major highways, Hospitals, schools, and churches. Orlando International Airport (MCO), Theme Parks, and International Drive’s iconic attractions are all within easy reach. Easy access and prime location make this home ideal for families, professionals, or anyone looking to enjoy the best of Florida living. Don’t miss your chance to make this wonderful property your dream home—schedule your private showing today!

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

Listing Agent: Dolly Strahan (407-234-8321)

Remarks: NEW PRICE! Property is Eligible for Free 1% interest rate Buydown for the first 12 months until June 30, 2026!!! 3-bedroom, 2-bathroom home located in a desirable area of Kissimmee, Florida. This property offers the freedom of NO HOA and NO CDD, making it a perfect option for homeowners or investors looking for flexibility and lower monthly expenses. The home features a functional layout with comfortable living spaces, ideal for families or those who enjoy entertaining. Conveniently situated near major highways, shopping centers, restaurants, schools, and just minutes from world-famous attractions in Central Florida. Kissimmee is known for its strategic location near Orlando and major theme parks, while also offering access to parks, lakes, and outdoor recreation throughout the area. Whether you are looking for a primary residence, vacation home, or investment property, this home offers an excellent opportunity in a rapidly growing Central Florida market. Don’t miss the chance to own a property in one of the most convenient and sought-after locations in the area. Additional Exterior and Interior property photos will be uploaded!

Listing is courtesy of: CAPITAL HOMES INC (800-642-0668)

Listing Agent: Alcides Gonzalez (407-267-6868)

Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bathroom home located in a highly sought-after neighborhood! Freshly updated with new exterior paint and the roof was replaced in 2023. Inside, you'll find beautiful tile flooring throughout, providing a sleek, low-maintenance aesthetic. The spacious layout features a bright and airy living area, perfect for both relaxation and entertaining. Enjoy the added privacy of no rear neighbors, creating a serene backyard space to unwind and enjoy the outdoors. With proximity to Disney, Universal, Sea World, shopping, schools, and local amenities, this home is ideally situated for convenience and ease of living.

Listing is courtesy of: TOHO REALTY GROUP, LLC (407-437-2893)

Listing Agent: Kerriann Sullivan (407-437-2893)

Remarks: Investment Opportunity – Tenant in Place Until October 2026! Welcome to this spacious 2-bedroom, 2-bath condo located in the heart of Kissimmee, just minutes from Walt Disney World, Universal, and major shopping and dining. This well-maintained unit features an open-concept layout, fully equipped kitchen, and a private balcony perfect for enjoying Florida’s sunshine. Currently leased at $1,700/month through October 2026, this property offers immediate rental income in a high-demand location. Whether you’re expanding your investment portfolio or seeking a vacation retreat with long-term tenants already in place, this condo is a solid choice. With a low-maintenance lifestyle and strong rental potential, this is your chance to own a profitable piece of Central Florida real estate. Don’t miss this opportunity—secure your investment today!

Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)

Listing Agent: Adriana Sanchez (321-947-4014)

Remarks: NO HOA! You won't want to skip viewing this well maintained 4-bedroom 2-bathroom home. Not many home come up for sale in this sought after community of Kings Point. The mature oak trees and landscaping throughout the neighborhood. The home itself sits on a large lot. As you enter through the front door you will admire the stone wood burning fire place in the formal living space. The double doors lead to the primary bedroom with a dream en suite bathroom. You will find a walk-in shower and separate tub, double vanity, and designated make up vanity. The sky light provides natural light with an amazing walk-in closet. Three other bedrooms with easy to clean laminate flooring. The kitchen provides ample storage and an island. Enjoy your morning coffee or tea on the spacious screened in back porch. The back yard offers endless possibilities install a pool for those hot Florida days, plenty of room for family/friend gatherings, storage for the toys. The back yard is completely enclosed by a vinyl fenced for extra privacy. The roof was replaced in 2018. Hot water heater is 3 yrs old, AC is 2026, blown insulation in attic, sprinkler system. Don't wait to schedule a private showing.

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

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