Homes for Sale Near Osceola High School in Kissimmee - 148 homes

Remarks: Price Improved to $202,000 — Exceptional Value! Welcome to this beautifully updated, fully furnished 2-bedroom, 2-bath villa in the heart of Kissimmee — a true turnkey opportunity for homeowners and investors alike. Price recently reduced, this move-in ready property offers outstanding value in a highly desirable location. Step inside to discover a bright, open-concept layout featuring tile flooring throughout, an updated kitchen, and a spacious living area designed for comfort and easy entertaining. Thoughtfully maintained and tastefully furnished, this home is ready for immediate occupancy or rental income potential from day one. A recently installed new roof adds long-term peace of mind and enhances the home’s overall appeal. Enjoy low-maintenance living in a well-established community with amenities including a sparkling pool and tennis courts. Conveniently located just minutes from shopping, dining, entertainment at The Loop, major highways, and Central Florida attractions, this property offers both lifestyle and convenience. Perfect as a primary residence, vacation getaway, or income-producing investment, this villa truly has it all: • Prime Kissimmee location • Fully furnished and turnkey • Move-in ready condition • Strong investment potential • Newly reduced price for added value Motivated seller — don’t miss this incredible opportunity. Schedule your private showing today!

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

Listing Agent: Angie Pereira (407-721-8945)

Remarks: Welcome to this beautifully updated home on a desirable corner lot in the heart of Kissimmee! From the moment you arrive, you’ll notice the fresh exterior paint, inviting curb appeal, and pride of ownership throughout. Step inside to discover a bright and spacious layout featuring a stunning updated kitchen designed to impress, complete with gorgeous quartz countertops, modern finishes, and the perfect setup for both everyday living and entertaining. The open flow of the home creates a warm and welcoming atmosphere ideal for gathering with family and friends. The primary suite offers a refreshed vanity area with stylish updates, creating a relaxing private retreat. Outside, the corner lot provides added space, privacy, and curb appeal that’s hard to find. Located in an incredibly convenient and highly sought-after Kissimmee location, you’re just minutes from The Loop, shopping, dining, Orlando International Airport, major highways, theme parks, Lake Nona, and all that Central Florida has to offer. Whether you’re looking for a primary residence or a vacation home, this move-in-ready property offers the perfect combination of location, updates, and value. Homes with upgrades like this in such a prime location do not last - schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Patrizia Harrington (908-329-0392)

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: Welcome to this exceptional former builder model home in the desirable Avilla community. This beautifully maintained 4-bedroom, 3-bath residence offers 3,410 heated square feet of thoughtfully designed living space on a spacious 0.21-acre homesite. The open floor plan features a gourmet kitchen with granite countertops, stainless steel appliances, custom cabinetry, and a large center island. The luxurious primary suite includes a spa-like bath and an oversized custom walk-in closet. Enjoy Florida living at its finest with a private screened pool, expansive pool deck, and fully equipped outdoor summer kitchen, perfect for entertaining. Originally purchased as the builder's final model home, the property showcases premium upgrades and exceptional craftsmanship throughout. Seller intends to convey the property substantially furnished, excluding personal belongings and décor. Conveniently located near shopping, dining, major highways, and Orlando's world-famous attractions. Schedule your private showing today!

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

Listing Agent: Elisio Almeida (407-640-9429)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 2-bath pool home offering space, comfort, and an unbeatable location in the heart of Kissimmee. This property is a rare find featuring a 4-bedroom layout with a heated pool and spa on an oversized lot, combined with exceptional curb appeal thanks to its beautifully refreshed landscaping and freshly painted exterior (2024). The large, spacious driveway provides ample room for multiple vehicles. Step inside to an open and airy floor plan with soaring cathedral ceilings that enhance the sense of space and natural light throughout. The centrally located kitchen is ideal for both everyday living and entertaining, featuring ample counter space, a breakfast bar, and a dining nook perfectly positioned by the sliding glass doors offering beautiful views of the pool and backyard. The primary suite is a true retreat, offering dual walk-in closets, a linen closet, and a spacious bathroom with dual sinks and a relaxing jacuzzi tub with jets. Enjoy Florida living at its best in your private backyard oasis situated on an oversized, fully fenced backyard with a mango and an orange tree. The large screened-in patio and heated pool with spa create the perfect setting for entertaining or unwinding year-round. Additional highlights include NO HOA, a roof replaced in 2022, a newer pool pump, a newer pool heat pump, and a well-maintained interior ready for its next owner. Ideally located just minutes from major highways, shopping, dining, and everyday conveniences. Only 5 minutes to Historic Downtown Kissimmee and within 30 minutes to Orlando International Airport and Central Florida’s world-famous attractions. This home offers the perfect combination of space, location, and lifestyle. Don’t miss the opportunity to make it yours! Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Dania Khreiche (407-456-1553)

Remarks: This updated beautiful corner lot home located at 101 Seneca Point Trl is now officially on the Market!! This 4 bedroom, 2 bathrooms home offers a perfect blend of comfort and style with many upgrades, 2018 roof installation, tiles flooring throughout, A/C 2022, HVAC, water heater, warm wooden cabinets with granite countertops, both bathrooms have been updated with matching countertops. Outside, enjoy your private oasis in the screened-in Pool, fully enclosed by a wht vinyl fence for added privacy. Plus, with solar panels already installed, you'll enjoy significant energy savings while living in comfort and style. Less than one mile from Super Wal-Mart and entertainment.

Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)

Listing Agent: Miguel Rivera (716-602-9489)

Remarks: Fantastic location in a highly desirable gated community! This move-in ready home is ideally located just minutes from The Loop Town Center, top rated restaurants, shopping plazas, medical facilities, major highways, the airport, and only 10 minutes from Disney and the theme parks. Enjoy added peace of mind with a BRAND NEW roof (05/2026) and NEW A/C, making this home truly move-in ready. Featuring an open floor plan filled with natural light, this beautifully maintained home offers 3 spacious bedrooms, high ceilings, a formal dining area, and a breakfast nook perfect for everyday living and entertaining. Residents enjoy resort-style amenities including a community pool, clubhouse, fitness center, tennis courts, walking trails, gated privacy, and HOA-maintained lawn care. This home truly combines comfort, convenience, and lifestyle in one exceptional location!

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

Listing Agent: Delia Navarro, Llc (321-541-8242)

Remarks: Under contract-accepting backup offers. Beautiful and spacious 4 bedroom, 2 bathroom home located in a highly desirable area, just minutes from shopping, dining, and everyday conveniences. This well-maintained property features a brand-new roof 2025 and has been freshly painted inside and out, making it truly move-in ready. Enjoy peaceful lake views from the backyard, perfect for relaxing or entertaining. The home offers a generous and functional layout ideal for comfortable living, along with a two car garage. Highly motivated seller! Competitively priced and ready to negotiate an excellent opportunity for both homeowners and investors, thanks to its prime location in a high-demand rental area. Schedule your showing today this one won’t last!

Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)

Listing Agent: Mercedes Corrente Bencomo (407-613-0006)

Remarks: 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: This beautiful townhouse is perfectly situated a short walk from the community heated swimming pool, spa, 24-hour fitness, clubhouse, and business center—everything you need right at your doorstep for resort style living! Located in a secure, gated community and move-in ready, this spacious 3-bedroom, 2.5-bath home offers both comfort and convenience in every detail. The large, bright kitchen features ample cabinetry, a newer granite island, and a double oven—ideal for everyday meals and effortless entertaining. Adjacent to the kitchen, the expansive dining room boasts an elegant tray ceiling and recessed lighting, creating a modern, upscale ambiance. The generously sized living room offers plenty of space for relaxing or hosting guests. Sliding glass doors lead to a screened-in patio—perfect for enjoying beautiful Florida days in comfort and style. Upstairs, the desirable split floor plan places the primary bedroom on one end for added privacy, with the second and third bedrooms located on the opposite side. One of the secondary bedrooms can easily be converted into a home office, making it perfect for today’s work-from-home lifestyle. The spacious primary suite includes a walk-in closet and a private ensuite with a tub/shower combination, granite countertop, and ample storage. The guest bathroom features a walk-in shower, granite countertops, and generous storage as well. All bathrooms are finished with granite countertops, adding a sleek, modern touch throughout. The first floor is finished with tile for easy maintenance, while the upstairs bathrooms also feature tile flooring, and the bedrooms are carpeted for added comfort. The home has a new AC unit (2024). Entire house painted (2024). A prime location just moments from Disney World, Silver Spur Arena and other major attractions, shopping and entertainment.

Listing is courtesy of: RANDOLPH & CO. (407-454-0214)

Listing Agent: Ron Randolph (407-454-0214)

Remarks: recently exterior painted. Beautiful updated townhouse at Sterling at Stonefield. This lovely 3 bedroom 2 bathroom with screened in patio and a 2 car garage townhome is a corner unit. It has been tastefully upgraded to please the future tenants. The townhome features ceramic tile throughout, new kitchen cabinets with stainless steel appliances and quartz countertop. The bathroom vanities have been upgraded with bronze faucets sand quartz countertops. The master has a spacious walk in closet and upgraded bathroom with a standup shower. No yard to mow since the HOA takes care of the trimming. The community is gated and has a fantastic clubhouse with pool and tennis. Come live in style close to the Loop!

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

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

Remarks: Under contract-accepting backup offers. 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. THE SELLER IS WILLING TO FINANCE $70,000 FOR THE BUYER AT AN INTEREST RATE OF FIVE FOR A TEN-YEAR MORTGAGE, BUT IT MUST BE THE FIRST MORTGAGE. NOT A SECOND ONE. FIRST MORTGAGE, SAME CONDITION AS A BANK.

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

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

Remarks: Welcome to this beautifully renovated 4-bedroom, 3-bathroom single-family home. The house features a skylight in the living room, perfect for relaxing or entertaining year-round. Situated on an oversized 12,545 sq ft lot, this property offers space, privacy, and endless possibilities—with NO HOA, giving you the freedom to personalize, expand, or invest without restrictions. Ideally located just minutes from Disney, Universal, and SeaWorld, with quick access to the Turnpike, shopping, dining, and only one hour from the beach, this home places you in the heart of Central Florida’s most desirable attractions. Move-in ready and thoughtfully updated, this property is perfect as a primary residence, vacation home, or income-producing investment. Don’t miss this opportunity—schedule your private showing today.

Listing is courtesy of: THE ARROW REALTY TEAM LLC (321-746-2899)

Listing Agent: Bibi Lopez (321-746-2899)

Remarks: Under contract-accepting backup offers. Step into this updated home. Featuring brand-new flooring and fresh interior paint, this home offers a clean, move-in-ready feel from the moment you walk through the door. The kitchen is equipped with sleek stainless steel appliances and a new AC in recent year. Major updates provide peace of mind, including a new roof installed in 2023. Ideally located just minutes from the Florida Turnpike, this home offers easy access for commuting while still being close to shopping, dining, and local amenities. Whether you're a first-time buyer or looking to downsize, this home checks all the boxes with style, comfort, and location.

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

Listing Agent: Brittany Pride (888-883-8509)

Remarks: Two stories, two bedrooms, two and a half baths, with the boring expensive stuff already handled. NEW roof overhead, NEW AC, NEW hot water heater, special assessment already paid, NEW living room flooring downstairs, NEW carpet up, and FRESH paint throughout. The first floor opens into a foyer that gives way to a full dining room on one side and a kitchen with breakfast bar seating on the other, both flanking a living room that stretches to back sliders. A second set of sliders off the front leads to a private patio, so you get cross-breeze and two outdoor spots before you even head upstairs. A half bath sits tucked off the kitchen for guests. Upstairs holds two true primary suites, each with its own full bathroom and its own private balcony. One faces the front, one faces the back, both have walk-in closets, and the laundry closet lives upstairs where the laundry actually is. Windsor Pines comes with a community pool and a playground, and the location does the rest of the work. You're a few minutes from The Loop, where the grocery run, the dinner reservation, and the movie all happen in one parking lot. Ten minutes to downtown Kissimmee and the lakefront, straight onto Osceola Parkway or the Turnpike when you need to be elsewhere, and about fifteen minutes from the Disney gates when you don't. Two primaries. Two porches. Two private balconies. One opportunity.

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

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

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: 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: 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: MOTIVATED SELLER!!!!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: Welcome to this stunning corner-unit townhome in the desirable, gated community of Cypress Ridge! Built in 2020, this beautiful property features 3 bedrooms, 2.5 bathrooms, and 1,771 sq. ft. of modern, open-concept living space. Being a premium corner lot, the home is flooded with natural light. The sleek kitchen boasts a large granite island and stainless steel appliances, flowing seamlessly into the bright living area. Step outside through the sliding doors to enjoy a serene pond view right from your backyard. Upstairs, the spacious primary suite offers a private retreat with dual vanities and a premium glass shower. Conveniently located in Kissimmee, you'll enjoy quick access to the FL Turnpike and Osceola Pkwy, keeping you minutes away from shopping, dining, and world-class attractions. Schedule your private showing today!

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Rosana Almeida (407-468-5600)