Homes for Sale Near Kissimmee Middle in Kissimmee - 278 homes

Remarks: This property is located in one of the nicest Subdivision in Kissimmee Area. Seller's Mortgage is assumable with 3.5% interest rate. Roof is less than 4 months old.

Listing is courtesy of: PREMIUM REAL ESTATE SERVICES (407-270-9550)

Listing Agent: Neree Augustin (407-697-7020)

Remarks: Experience resort-style living in this stunning 5-bedroom, 5.5-bath cottage located in the highly sought-after Margaritaville Resort Orlando. Perfectly positioned on an oversized corner lot, this home offers exceptional privacy along with its own private pool and heated spa, creating the ideal setting for relaxation or entertaining. This beautifully designed two-story floor plan comes fully furnished, with every detail thoughtfully selected to create a light, airy, coastal atmosphere. Soft mint and pastel yellow tones, wood-plank tile flooring, and energy-efficient stainless steel appliances all come together to provide both style and function. Natural light fills the home, enhancing the bright “beach breeze” ambiance throughout. The layout features two bedrooms on the first floor and three bedrooms upstairs, including a spacious primary suite. Each of the three second-floor bedrooms boasts its own en-suite bathroom, ensuring comfort and convenience for guests. The two upstairs guest rooms offer private balconies, while the primary suite also enjoys access to outdoor space for peaceful moments of retreat. A dedicated half-bath off the lanai adds extra ease for poolside living. Located within Margaritaville Resort, residents and guests enjoy world-class amenities and a prime location with quick access to major highways, shopping, dining, and—best of all—the Disney parks. Whether you're seeking a high-performing short-term rental investment or a beautiful place to call home long-term, this cottage embodies the ultimate laid-back Florida lifestyle.

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Troy Boss (315-335-4622)

Remarks: Ask about a lender provided RATE BUY-DOWN CREDIT on this home ** Seller may consider buyer concessions if made in an offer ** Welcome to Encantada Resort, where style, comfort, and convenience come together just 5 miles from the gates of your favorite Disney parks! This FULLY FURNISHED, TURN-KEY townhome is ready to impress with its NEW, UPGRADED FURNITURE and TRANSFERABLE BOOKINGS – a true income producing opportunity or perfect personal getaway. Inside, the OPEN CONCEPT MAIN FLOOR features easy-care tile, a modern well equipped kitchen, spacious living and dining areas, and sliding glass doors leading to your PRIVATE SCREENED PATIO complete with a hot tub for the ideal spot to unwind after a day at the parks. A convenient half bath is located on the main level, while both bedrooms upstairs feature EN-SUITE BATHS for comfort and privacy. Thoughtfully decorated with fresh, modern touches and plenty of natural light, this home also includes a laundry room for added ease. Encantada offers a wealth of RESORT STYLE AMENITIES, including two heated pools, a fitness center, restaurant/bar, playground, walking trails, clubhouse with billiards and darts, and complimentary Wi-Fi throughout. With GATED ACCESS and a prime Kissimmee location, you will have everything you need for relaxation and recreation just minutes from world-class attractions. Whether you are looking for a vacation retreat or an investment opportunity, this property delivers exceptional value and a resort lifestyle that keeps guests coming back again and again. Call today for more information and schedule a tour!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Seller may consider buyer concessions if made in an offer ~ Picture perfect ground floor unit in the Terraces at Storey Lake - zoned for SHORT TERM RENTALS/AIRBNB’S - with RESORT STYLE AMENITIES - just minutes from Disney theme parks and other world renowned Central Florida attractions! Newly built in 2019 this FULLY FURNISHED and TURN-KEY home delivers a bright OPEN CONCEPT with TILE FLOORS for easy maintenance, a modern kitchen with every bell and whistle, IN-UNIT LAUNDRY and even a nice outdoor patio to relax and unwind at the end of a long day. Two large bedrooms both offer WALK-IN CLOSETS for ample storage with the primary also featuring a private en-suite bath. The new owner will appreciate the attention to detail while designing this home and the whimsical Disney touches make the time spent here simply magic. The Terraces has a community pool for residents to enjoy and being a part of the larger Storey Lake means an array of exciting amenities. Storey Lake is a GUARD GATED community with something for everyone; RESORT STYLE POOL and spa, splash pad, LAZY RIVER, a mini golf course, poolside food and beverage service, canoe/kayak rentals and more. Have some fun in the sun while partaking in the daily activities on site or take a short ride to visit local theme parks. In a central location for easy access to I-4, 192, Osceola Parkway and the 417. Shopping, dining, parks, lakes and all the entertainment you could ask for are at your fingertips in this vibrant community! Whether you are looking for a home away from home, vacation spot or investment opportunity, look no further than Clock Tower Drive!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Under contract-accepting backup offers. ***2023 roof, high growth area, great for investors, location, location & location*** Prime Income-Producing Triplex in the Heart of Kissimmee! This well-maintained multifamily property offers a versatile unit mix totaling over 3,700 square feet of living space, making it an excellent opportunity for both investors and owner-occupants. Built in 1985 and situated on a generous oversized lot, the property features solid construction, ample parking, and a functional layout ideal for long-term or short-term rental potential. The property includes one 2-bedroom, 2-bath unit; one two-story unit featuring 2 bedrooms, 1 full bath, and an additional half bath; and one spacious 3-bedroom, 2-bath unit that also includes a separate studio with its own 1-bedroom, 1-bath layout, complete with kitchen and living area—perfect for additional rental income or guest accommodations. All units are currently occupied, generating approximately $5,900 in monthly rental income, with potential for future increases. Each unit provides comfortable living areas with strong rental appeal in a high-demand location just minutes from major roadways, shopping, dining, and world-renowned attractions. With no HOA restrictions, owners enjoy flexibility in management and use. Public water and sewer connections ensure convenience and reliability. Whether you’re looking to expand your portfolio or secure a steady cash-flowing asset in a growing market, this property delivers on location, size, and income potential. Don’t miss this rare opportunity in one of Central Florida’s most active rental corridors.

Listing is courtesy of: GEEK REALTY (407-885-3850)

Listing Agent: Mr.Geek Meah (407-885-3850)

Remarks: Under contract-accepting backup offers. MOVE-IN READY! Rare opportunity for first-time buyers or investors, perfectly suited for both long-term living and short-term rental income. Located on a corner lot in the highly desirable Indian Point community, this well-maintained screened pool home stands out with very low HOA fees and access to great amenities including a clubhouse, community pool, playground, and tennis courts. The location is a major highlight, just under 20 minutes to Disney, and less than 35 minutes to Universal Studios and Orlando International Airport, with quick access to HWY 192, plus nearby shopping, dining, hospitals, and entertainment. Inside, the home offers vaulted ceilings, tile flooring in the main areas, no carpet,  neutral paint, and an abundance of natural light through large windows and sliding doors, creating a bright, open, and low-maintenance space. The private screened pool adds strong lifestyle and rental appeal, making this home an excellent option as a primary residence, vacation home, or income-producing property in the heart of Central Florida.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: Stunning Fully Renovated 2BR/2BA Fantasy World Club Villas – A Rare Find Just Minutes From Disney! Step into one of the finest villas in all of Fantasy World Resort! This beautifully renovated and fully furnished 2-bedroom, 2-bath villa offers an elevated vacation-home experience with high-end finishes, an open-concept layout, and incredible income potential. Whether you're looking for a top-performing short-term rental or a stylish getaway for your family, this is the opportunity buyers wait for. This upgraded villa features stainless steel appliances, elegant stone countertops, modern décor, and a spacious feel rarely found in comparable units. The seller removed the lowered ceiling and opened the wall between the kitchen and living room, creating a bright, seamless layout that truly sets this villa apart from the rest. With strong rental performance—capable of producing up to $50,000 per year—this property is both a lifestyle upgrade and an excellent investment. Buyers also have the option to purchase a second, similarly upgraded villa for a powerful package deal. Located just 10 minutes from Walt Disney World, this resort is one of the highest-performing communities in the Kissimmee/Orlando market. Enjoy world-class amenities including a huge lazy river, water slides, multiple pools and hot tubs, mini golf, tennis and pickleball courts, arcade, dog-friendly areas, EV charging, and more—making it a vacation favorite year-round. Opportunities like this don’t come often. If you’ve been waiting for a truly renovated, income-producing villa near the parks, this is the one. ?? Contact your Realtor today to schedule a private showing — and feel free to reach out to listing agent Jose Hooker directly for more details and access.

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

Listing Agent: Jose Hooker-Gomez (407-272-6986)

Remarks: Stunning Fully Renovated 2BR/2BA Fantasy World Club Villas – A Rare Find Just Minutes From Disney! Step into one of the finest villas in all of Fantasy World Resort! This beautifully renovated and fully furnished 2-bedroom, 2-bath villa offers an elevated vacation-home experience with high-end finishes, an open-concept layout, and incredible income potential. Whether you're looking for a top-performing short-term rental or a stylish getaway for your family, this is the opportunity buyers wait for. This upgraded villa features stainless steel appliances, elegant stone countertops, modern décor, and a spacious feel rarely found in comparable units. The seller removed the lowered ceiling and opened the wall between the kitchen and living room, creating a bright, seamless layout that truly sets this villa apart from the rest. With strong rental performance—capable of producing up to $50,000 per year—this property is both a lifestyle upgrade and an excellent investment. Buyers also have the option to purchase a second, similarly upgraded villa for a powerful package deal. Located just 10 minutes from Walt Disney World, this resort is one of the highest-performing communities in the Kissimmee/Orlando market. Enjoy world-class amenities including a huge lazy river, water slides, multiple pools and hot tubs, mini golf, tennis and pickleball courts, arcade, dog-friendly areas, EV charging, and more—making it a vacation favorite year-round. Opportunities like this don’t come often. If you’ve been waiting for a truly renovated, income-producing villa near the parks, this is the one. ?? Contact your Realtor today to schedule a private showing — and feel free to reach out to listing agent Jose Hooker directly for more details and access.

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

Listing Agent: Jose Hooker-Gomez (407-272-6986)

Remarks: Turn-key opportunity in the highly sought-after Storey Lake Resort! This fully furnished and beautifully equipped 2-bedroom, 2-bathroom condo is rental-ready and well-suited for short-term rental use or as a vacation home. A standout feature of this unit is its Disney-themed bedrooms, featuring Star Wars and Mickey Mouse designs that create a fun and memorable experience for guests of all ages. The themed décor adds a unique touch that is highly appealing in the short-term rental market. This unit has also been a consistently rented property within the current property management program. The thoughtfully designed open-concept layout offers a bright and welcoming space. The modern kitchen comes fully equipped with appliances, cookware, and utensils. A versatile nook with an additional sofa bed provides flexibility for use and accommodations, while a dedicated desk area is ideal for remote work or extended stays. Step out onto the private balcony and enjoy the lake views, a perfect setting for relaxing after a day out. Located on the top floor, this unit offers added privacy with no upstairs neighbors. Conveniently located just minutes from Walt Disney World, Disney Springs, shopping, dining, and Orlando’s main attractions, Storey Lake Resort is a popular destination for visitors. The community offers a variety of amenities including a resort-style pool, lazy river, water slides, splash pad, fitness center, sports courts, and more. Whether you are looking for a vacation home or a property suitable for short-term rental use, this condo offers a great combination of location, features, and convenience.

Listing is courtesy of: INTERINVESTMENTS REALTY, INC. (305-220-1101)

Listing Agent: Emilio Cardenal, Jr. (305-220-1101)

Remarks: Completely Renovated & Move-In Ready.......Don’t Miss This Opportunity! Welcome into this gorgeous 2-bedroom, 1-bath condo showcasing new laminate flooring, a beautifully tiled shower, fresh designer paint, and updated doors throughout. The sleek, modern kitchen features brand-new cabinets and appliances, perfect for cooking and hosting. This home is filled with abundant natural light, creating a bright and inviting atmosphere. It's conveniently located near shopping, dining, and entertainment, this home offers both style and accessibility. Enjoy resort-style living in a gated community with a pool and lush landscaping. Don't miss out on this amazing property, schedule your showing ASAP

Listing is courtesy of: CHAMPIONSGATE REALTY (407-818-5588)

Listing Agent: Elaine Mejia (321-274-2225)

Remarks: Discover your dream retreat in this beautifully furnished 2-bedroom, 2-bathroom condo located in the desirable Runaway Beach Club community. Featuring a spacious master bedroom complete with an ensuite bathroom, this condo is perfect for both personal enjoyment and short-term rental opportunities. Enjoy breathtaking lake views and a serene atmosphere in this secure, quiet community. Take advantage of a wealth of amenities, including a sparkling pool, fitness center, BBQ area, and high-speed internet access, ensuring a lifestyle of comfort and convenience. With its prime location just minutes from major theme parks, shopping, and dining, this condo is an ideal investment for anyone looking to combine leisure with the potential for rental income. Don't miss out on this incredible opportunity – schedule your private viewing today!

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

Listing Agent: Jaqueline Santos De Tabares (786-452-5684)

Remarks: Welcome to your perfect getaway! This beautifully furnished 2-bedroom, 2-bath condo offers an inviting retreat and is ideal for both short-term rentals and permanent living. Nestled in building 2 with open parking, this is the closest to the community pool and amenities, this corner unit features a stunning wooded view from the screened porch, providing a serene backdrop for relaxation. The master bedroom includes a private balcony perfect for sipping morning coffee, as well as a luxurious ensuite bathroom complete with double sinks, a soaking tub, and a separate shower. The open-concept kitchen seamlessly connects to the living area and dining room, creating an inviting space for entertaining friends and family. Step out onto the screened balcony and soak up the warm Florida weather while enjoying the tranquil surroundings. The Caribe Cove resort enhances your living experience with a host of amenities, including a community pool, hot tub, fitness center, arcade room, clubhouse, and more. Conveniently located near popular attractions, shopping, dining, golf courses, and supermarkets, this condo is perfectly situated for both relaxation and adventure. Don’t miss the opportunity to make this stunning unit your own or capitalize on its rental potential. Discover the idyllic lifestyle that awaits you at Caribe Cove!

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

Listing Agent: Jaqueline Santos De Tabares (786-452-5684)

Remarks: Updated first-floor condo offering 2 bedrooms and 2 bathrooms with bright white walls and no carpet throughout—creating a clean, modern feel from the moment you walk in. The open kitchen features a convenient breakfast bar, separate dining area, and a spacious pantry for added storage. A split floor plan provides privacy, with generously sized bedrooms and updated bathrooms that include custom sink spouts and upgraded bathtubs. Step outside to your screened-in patio—perfect for enjoying Florida living year-round without the bugs. Washer and dryer hookups are available, just bring your own units! This move-in ready home is located in the desirable Arbors of Sendera community, where residents enjoy amenities including a pool, fitness center, clubhouse, and playground. Ideally situated off Columbia Ave and Hoagland Blvd in Kissimmee, you’ll love the convenience of being close proximity to shopping, dining, schools, and public transportation, with easy access to major highways. Just minutes from The Loop and a short drive to Orlando. Don’t miss your opportunity to make this beautifully updated condo your next home!

Listing is courtesy of: ACKLEY LEGACY PROPERTIES, LLC (407-730-3555)

Listing Agent: Kristen Chowdhury (407-721-3829)

Remarks: **WATERFRONT** If you're looking for an open-floor plan move-in ready home with a waterfront view, you've found it. Located in the heart of Hunter's Creek less than 5 minutes from The Loop Town Center, this home is ready to meet its new owners. Highlights: Three spacious bedrooms with walk-in California style closets, high ceilings, tons of windows and natural light, long entry corridor, gourmet kitchen with tiled mosaic floors, formal dining area PLUS a breakfast nook area, and a screened-in front porch and rear porch. Laundry room features custom built-in cabinets for extra storage and washer/dryer is also included. Major appliances: Roof (2020) AC (2019). Home is also equipped with wired security cameras, an irrigation system, and rain gutters. But let's be honest, the real selling point is that WATER VIEW. Talk about peace and serenity! Enjoy resort-style community amenities such as a community pool, clubhouse, fitness center, tennis courts, and walking trails. You'll never be bored! HOA covers your lawn maintenance and let's not forget, the community is gated and private. Located close to shopping plazas, restaurants, entertainment, medical facilities and highways, everything you could ever want is within a mile radius. Bonus: Disney is only 10 minutes away!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Angie Kollcaku (407-454-4078)

Remarks: Welcome to this beautifully furnished 3-bedroom, 2-bathroom condo located in the tranquil and gated community of Caribe Cove. Offering the perfect blend of luxury and comfort, this spacious condo is ideal for both personal enjoyment and investment, with short-term rentals allowed. The open-concept living area features large windows that fill the space with natural light, creating a warm and inviting atmosphere. The modern kitchen is equipped with contemporary appliances, sleek cabinetry, and ample counter space—perfect for entertaining or everyday living. Step out onto your private balcony to enjoy your morning coffee or unwind with peaceful sunset views. Each bedroom offers generous space and privacy, while the master suite includes an en-suite bathroom for added convenience. Residents enjoy access to top-tier amenities including a resort-style swimming pool, fitness center, and beautifully landscaped grounds. Located just minutes from theme parks, shopping, dining, and entertainment, this condo combines serene living with unbeatable accessibility.

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

Listing Agent: Jaqueline Santos De Tabares (786-452-5684)

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. 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: Dream townhome alert! This gorgeous 4BR/3BA (including 2 ensuites) unit in San Vitorino Cir, Kissimmee offers 1,470 sq ft of bright, open living space perfect for entertaining and relaxing. With a recently remodeled owner's suite and a recently replaced AC unit and boiler. Enjoy your morning coffee on the small patio / varanda, and experience the comfort of move-in ready Florida living. The community features 3 sparkling pools, a full clubhouse, and plenty of amenities for fun and fitness. Prime location near highways, shopping, dining, and schools— don’t wait, your new home awaits!

Listing is courtesy of: DEBRASSI REALTY LLC (407-446-1343)

Listing Agent: Marcela Andrade Drummond (407-752-2323)

Remarks: SELLER MOTIVATED - PRICE TO SELL - GREAT OPPORTUNITY STUNNING FULLY RENOVATED 3 BEDROOM POOL HOME – PRIME LOCATION IN KISSIMMEE Welcome to this beautifully upgraded 3-bedroom, 1 bonus room, 2-bathroom home located and a spot available with possibility to build a one more bathroom. This property has been completely renovated with high-end finishes throughout and offers the perfect blend of elegance, comfort, and Florida lifestyle living. Fully renovated interior. Premium, first-line flooring throughout. Sophisticated wood panel accent walls. Designer-decorated bedrooms. Completely remodeled kitchen with modern finishes. Updated bathrooms with contemporary style. Extended driveway for additional parking Private heated pool with spa. Outdoor gourmet area perfect for entertaining. Beautiful pond water view with a colonial-style architectural details. Gated community for added security. The open floor plan creates a bright and welcoming atmosphere, ideal for both primary residence, vacation home, or investment property. The backyard is a true retreat, featuring a heated pool and spa overlooking a peaceful pond view — perfect for relaxing evenings or entertaining guests. This home shows pride of ownership and attention to detail in every corner. The bedroom furniture has been removed; the summer kitchen needs to be finished, and the refrigerator was removed because it was broken. Seller is highly motivated and priced to sell. Excellent opportunity in one of Kissimmee’s most sought-after areas, close to major highways, shopping, dining, and attractions.

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

Listing Agent: Francisco Tatagiba Junior (386-517-3488)

Remarks: **Turnkey Resort Townhome – Active Short-Term Rental Opportunity** Welcome to this beautifully maintained 4-bedroom, 3-bath fully furnished townhome located in the highly desirable guard-gated resort community of Venetian Bay Villages. This turnkey property is currently operating as an active short-term rental, making it an excellent opportunity for investors, vacation home buyers, or full-time residents. The home features a spacious open living and dining area, a fully equipped kitchen, and a private porch just off the living room—perfect for relaxing after a day enjoying Central Florida’s attractions. The primary bedroom with en-suite bath is conveniently located on the first floor, while the second level offers additional bedrooms, including one bedroom with its own en-suite bathroom, providing comfort and privacy for guests and family. Residents and guests enjoy resort-style amenities, including multiple swimming pools, tennis courts, basketball courts, volleyball courts, a large clubhouse and recreation center, fitness center, game room, and playground. Ideally situated just minutes from Walt Disney World, The Loop, and Lake Tohopekaliga, with convenient access to shopping, restaurants, International Drive, and world-famous theme parks. Fully furnished and move-in or rental ready. Whether you’re looking for a vacation getaway, investment property, or primary residence, this home offers flexibility, location, and resort-style living all in one.

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

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

Remarks: Welcome to 2620 Santosh Cove, a beautifully maintained and fully furnished 4-bedroom, 3.5-bath pool home located in the highly desirable gated community of Veranda Palms. Whether you're searching for a primary residence, vacation retreat, or income-producing investment property, this home checks every box. Approved for both short-term and long-term rentals, this property offers exceptional flexibility for homeowners and investors alike. The home has demonstrated consistent guest demand, making it a strong opportunity for those seeking rental income in one of Central Florida’s most popular vacation corridors. Inside, you'll find a thoughtfully designed layout with a fully equipped kitchen, spacious living areas, and turnkey furnishings — everything conveys, making this a true move-in or rent-ready opportunity. Step outside to your private screened pool with no rear neighbors, offering added privacy and relaxation. The garage is currently converted into a game room for added entertainment value, but can easily be reverted back to a traditional garage if preferred. Beyond the home itself, location is everything. Just minutes away you’ll find major grocery stores, restaurants, outlet malls, and everyday conveniences — including a nearby Sam’s Club — making extended stays and guest turnovers seamless and convenient. All of this is located just a short drive to Disney, Orlando’s world-class attractions, and major roadways. Residents of Veranda Palms enjoy resort-style amenities including a clubhouse, pool with water slide, fitness center, splash park, and more — all within a secure gated community. This is a rare opportunity to own a versatile property in a prime location that offers lifestyle, convenience, and income potential all in one.

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

Listing Agent: Tai Phan (877-366-2213)