Homes for Sale Near Kissimmee Middle in Kissimmee - 296 homes

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: 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: **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)

Remarks: Under contract-accepting backup offers. Opportunity is knocking at Terra Condo’s in Kissimmee! This FIRST FLOOR ~ END-UNIT condo is being sold FURNISHED, and is priced so you can bring your vision and make it your own. Whether you are ready to modernize with fresh finishes or lean into a bit of its vintage charm, the possibilities are wide open here. With just a little TLC, this light and bright space can truly shine! A covered front entry welcomes you inside to a nice layout featuring dedicated living and dining spaces that feel open yet defined. Natural light pours in thanks to the end-unit location, giving the home an airy feel throughout. The galley-style kitchen offers a generous amount of cabinet and counter space, providing a functional layout that is ready for your personal touch. Off the dining area, sliding glass doors lead to a SCREENED LANAI complete with a convenient STORAGE closet – perfect for enjoying Florida’s year-round weather. Located in a GATED ACCESS, all owner-occupied community, Terra Condo offers amenities designed for easy living, including a COMMUNITY POOL and clubhouse, with water, sewer, and trash included in the HOA. The location puts you close to shopping, dining, local lakes, area resorts, and world-famous theme parks, making it ideal as a primary residence or seasonal getaway! If you have been looking for an affordable first-floor condo in Kissimmee with room to add value and personalize, this is your chance. Bring your ideas and unlock the potential! **Seller may consider buyer concessions if made in an offer**

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

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

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: Don’t miss this incredible opportunity to own a fully furnished luxury vacation home in the highly sought-after Storey Lake Resort! This beautifully maintained 4-bedroom, 3-bathroom property offers a spacious and functional layout, perfect for both short-term rental investment and personal use. Ideally located just minutes from Orlando’s world-renowned attractions, including Disney, Universal Studios, SeaWorld, premium outlets, shopping, and dining, this home provides the perfect combination of convenience and lifestyle. Inside, you’ll find an open-concept floor plan designed for comfort and entertainment. The modern kitchen features spacious countertops, ample cabinetry, and a seamless flow into the dining and living areas. The home is tastefully decorated and fully equipped, making it truly turnkey for immediate rental income or personal enjoyment. The bedrooms are generously sized and thoughtfully designed to accommodate both owners and guests comfortably. The layout offers privacy and flexibility, making it ideal for vacation stays or extended use. Step outside to your private outdoor space, perfect for relaxing or entertaining. Whether enjoying Florida’s sunshine or unwinding after a day at the parks, this home delivers the ultimate vacation experience. Storey Lake Resort offers world-class amenities with two resort-style clubhouses, featuring lazy rivers, resort pools, water slides, splash pads, fitness centers, tiki bars, mini-golf, sports courts, playgrounds, and kayak rentals. The community provides a true resort-style atmosphere and is one of the most desirable vacation destinations in Central Florida. Zoned for short-term rentals, this property is an excellent opportunity for investors seeking strong rental potential in a prime location. Whether you are looking for a strong rental potential property or a vacation retreat, this home checks all the boxes. Schedule your private showing today!

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

Listing Agent: Danilo Aquino (689-243-6300)

Remarks: Welcome to this beautiful, completely renovated villa. Location, location, location! This area in downtown Kissimmee is situated close to The Loop Shopping Center, featuring all the best shops and restaurants. It also offers access to top-tier medical care, including hospitals, medical specialists, and excellent healthcare services. This villa has been fully renovated and features stainless steel appliances, granite countertops, a washer and dryer, updated bathrooms, and perfectly coordinated wood flooring. Additionally, it includes two parking spaces directly in front of the property. The community also offers a swimming pool and a recreational area.

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

Listing Agent: Yolanda Gonzalez (407-535-9722)

Remarks: NO CARPET throughout the home!! Bathrooms renovated in April 2026. A/C (2025). FULLY FURNISHED & MOVE-IN READY! Discover this magical 4-bedroom, 3-bathroom home on Shine Dr in WEST LUCAYA VILLAGE, perfectly positioned just 10 miles from Magic Kingdom and conveniently LOCATED DIRECTLY ACROSS FROM THE CLUBHOUSE AND LEISURE FACILITIES! This exceptional property comes COMPLETELY FURNISHED and features enchanting Disney and Harry Potter themed bedrooms that will captivate guests and family alike. ZONED FOR SHORT TERM RENTAL - This property is legally approved for vacation rentals, making it an excellent income-producing investment opportunity! enjoy beautiful, easy-to-maintain flooring perfect for Florida living and vacation rental operations. Located in WEST LUCAYA VILLAGE on the highly desirable US-192 corridor in Kissimmee, this home provides unbeatable convenience to all Central Florida attractions while being nestled in a resort-style community. The HOA fee of $575 includes HIGH-SPEED INTERNET and CABLE TV. RESORT-STYLE AMENITIES include a stunning clubhouse with sparkling pool, fully equipped fitness center, and playground - perfect for family entertainment and enhancing rental guest experience. EXCEPTIONAL SHORT TERM RENTAL OPPORTUNITY - The magical themed rooms, prime Disney-area location, and resort amenities make this property ideal for generating strong rental income. Whether you're seeking a primary residence, vacation home, or investment property, this turnkey gem offers immediate enjoyment and proven income potential. Don't miss this chance to own a piece of the magic - schedule your showing today!

Listing is courtesy of: KARDOSH REALTY (407-499-4466)

Listing Agent: Frederico Hexsel (407-745-8841)

Remarks: Welcome to 2801 Oakwater Dr, Kissimmee, FL 34747 - This 3-bedroom, 2-bathroom end-unit condo with a 1-car garage is located in the gated Oakwater community, just minutes from Walt Disney World, major attractions, shopping, dining, and Central Florida highways. This 1,465 sq ft condo features a split-bedroom floor plan with the primary suite positioned at the rear for added privacy, including water views, dual closets, and an ensuite bath with shower. The kitchen includes granite countertops, breakfast bar seating, ample cabinetry, and all appliances. The open living and dining areas provide access to a private lanai overlooking the lake. Additional features include an interior laundry closet with washer and dryer, attached garage, and exterior storage. The end-unit location provides added natural light and privacy. Oakwater offers resort-style amenities including a clubhouse, fitness center, game room, community pool, tennis courts, and playground. HOA includes cable TV, internet, and exterior maintenance. This property may be suitable as a primary residence, second home, or investment opportunity. Buyers should verify leasing restrictions and HOA guidelines. Schedule your showing today.

Listing is courtesy of: PLATINUM REAL ESTATE (888-974-7253)

Listing Agent: Scot Hartwell (407-791-8466)

Remarks: HUGE PRICE REDUCTION! Welcome to this inviting and well-maintained home located in the heart of Kissimmee. Offering a functional layout with spacious living areas, this property blends comfort, convenience, and everyday practicality. Natural light flows through the home, creating a warm and welcoming atmosphere perfect for both relaxing and entertaining. The generous backyard provides endless possibilities — ideal for gatherings, gardening, or creating your own outdoor retreat. With no HOA, you’ll enjoy flexibility and freedom rarely found in today’s market. Centrally located near shopping, dining, schools, and major highways, this home offers easy access to everything Kissimmee has to offer while still providing a sense of privacy and calm. Whether you’re a first-time buyer, growing household, or investor, this property represents a solid opportunity and a place ready to create new memories. Schedule your private showing today — homes like this don’t last.

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

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

Remarks: Welcome to your vacation lifestyle! This stunning 3-bedroom, 2-bathroom, two-story condo is located in the highly desirable Venetian Villages resort community. Perfect for either a primary residence or a lucrative short-term rental investment. Property Highlights Two-Story Layout: Enter into a bright, open-concept living room/dinette combo. Modern Kitchen: Features granite countertops and brand-new appliances, overlooking the main living area for easy entertaining. First-Floor Primary: The primary bedroom is conveniently located on the main floor with an ensuite bathroom (shower-tub combo). Convenient Laundry: Includes a new, full-size stackable washer/dryer set on the first floor. Upstairs Bedrooms: The second floor offers two additional bedrooms and a shared full bathroom, plus a dedicated owners' storage closet in the hall. Community Features Enjoy an amazing array of resort-style amenities including a sparkling pool, tennis courts, basketball courts, and a volleyball court. The community's location and amenities are ideal for buyers seeking a peaceful, vacation-like setting or investors looking for a prime rental property. Don't miss out on this excellent opportunity!

Listing is courtesy of: LUXE HUNTER REAL ESTATE (407-984-4888)

Listing Agent: Millie Alicea (407-929-1646)

Remarks: **BEAUTIFUL TOWNHOME 5 BED / 4 BATH Very well decorated. Located in a corner lot in one of the most desirable short-term rental resort communities with 5 bedrooms and 4 bathrooms, open floor plan, the kitchen is fully equipped and features 42" modern gray cabinets, brushed stainless steel appliances, all connected to the cozy living and dining room. The sliding door will lead to an extended covered patio area and a splash pool, where the deck offers plenty of room to relax. The Clubhouse offers a resort-style pool and lazy river, two water slides, and a splash park. Kayak rentals a 9-hole mini golf course, and sand volleyball courts for fun and entertainment are available. The fitness center is well equipped and is open for extended hours for our guests. There is an outdoor Tiki bar where you can order your favorite drink, food, or ice-cream. Whether using this home for your full-time residence or vacation home investment, this community and home will take you on a relaxing retreat, Perfectly located just minutes from Disney Parks, Vineland Premium Outlet, The Loop Mall, SeaWorld, Universal Studios, Walmart, Target, Lake Buena Vista Factory Stores, Gas Stations, Restaurants, and much more. Call now and set up a showing.

Listing is courtesy of: KAZA REAL ESTATE LLC (407-723-8230)

Listing Agent: Eddie Ferrei Ferreira (407-272-0113)