Homes for Sale Near Kissimmee Middle in Kissimmee - 306 homes

Remarks: Cypress Cay is a beautiful new townhome community in the heart of Kissimmee, featuring spacious townhomes with open-concept home designs, 1-2 car garages, energy efficient features, built-in Smart Home Technology and water & conservation views. Unbeatable community and HOA amenities include a pool & cabana, playground, half-court basketball court, dog park, walking trails and a fiber network providing up to 1 Gigabit internet speed. This ideal location offers convenient access to I-4, 417, Osceola Parkway, International Drive, Apopka Vineland Road, The Loop, Disney, Old Town, and SeaWorld - all just minutes away. Homes are selling quickly so contact us today!

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Brian Vento (305-725-9359)

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. Welcome to your next top-performing short-term rental in the heart of Central Florida's most sought-after resort community, Storey Lake Resort! This stunning LAKEFRONT 4 bedrooms/3 bathrooms townhome puts investors and vacationers alike just minutes from Walt Disney World, SeaWorld, Universal Studios, and Orlando's world-class dining and shopping. Nestled within this 24-hour gated resort, owners enjoy the flexibility to rent short-term year-round, making this a true income-generating machine. The resort's Hideaway Clubhouse delivers a full vacation experience with two water slides, a lazy river, splash zone, resort-style pools, oversized hot tub, Tiki Bar, fitness center, mini-golf, kayak rentals, beach volleyball, game room. HOA includes cable TV and internet, pool maintenance, grounds care, insurance, trash, and 24-hour guard. Whether you're expanding your STR portfolio or seeking a personal vacation retreat with income potential, this is the opportunity you've been waiting for. Turnkey, fully furnished and move-in ready. Just add guests and start earning! Schedule your visit now!

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

Listing Agent: Patricia Fraga Alvares, Pa (407-219-6229)

Remarks: Excellent opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in the highly desirable Berkley Resort community. Approved for short-term rentals, this property offers exceptional income-producing potential in one of Central Florida’s most sought-after vacation rental markets. Residents and guests enjoy resort-style amenities including two swimming pools, splash pad, fitness center, tennis and basketball courts, beach volleyball, scenic lake access, and 24-hour gated security. Ideally located just minutes from Walt Disney World, major attractions, shopping, dining, and Orlando's main transportation corridors, this property is perfect as a vacation home, investment property, or primary residence.

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

Listing Agent: Keegan Siegfried (813-670-7226)

Remarks: Excellent opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in the highly desirable Berkley Resort community. Approved for short-term rentals, this property offers exceptional income-producing potential in one of Central Florida’s most sought-after vacation rental markets. Residents and guests enjoy resort-style amenities including two swimming pools, splash pad, fitness center, tennis and basketball courts, beach volleyball, scenic lake access, and 24-hour gated security. Ideally located just minutes from Walt Disney World, major attractions, shopping, dining, and Orlando's main transportation corridors, this property is perfect as a vacation home, investment property, or primary residence.

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

Listing Agent: Keegan Siegfried (813-670-7226)

Remarks: Welcome to this fully furnished 4-bedroom, 3-bathroom townhome located in the highly desirable 24-hour guard-gated community of Venetian Bay Villages. Whether you're looking for a primary residence, a vacation home, or an investment opportunity, this property offers incredible potential in one of Kissimmee's most convenient locations. The home is being sold fully furnished, providing a great starting point for personal use or future rental income. The functional floor plan offers spacious living areas, a well-equipped kitchen, and comfortable accommodations for family and guests. Venetian Bay Villages features outstanding resort-style amenities, including multiple swimming pools, a clubhouse, fitness center, tennis, basketball and volleyball courts, playgrounds, picnic areas, scenic walking paths, and beautifully maintained common areas. Ideally located just minutes from Walt Disney World, Universal Orlando, SeaWorld, The Loop shopping and dining, Orlando International Airport, major highways, and countless Central Florida attractions. Seller is motivated and welcomes offers. Don't miss this excellent opportunity to own a property with tremendous potential in one of Kissimmee's most sought-after gated communities

Listing is courtesy of: BAHIA INTERNATIONAL REALTY (407-608-5308)

Listing Agent: Alexandra Mateu (321-332-8039)

Remarks: Welcome to this stunning 5-bedroom, 5-bathroom home, where comfort, style, and adventure come together in one exceptional property. Designed with both relaxation and entertaining in mind, this spacious home features an open-concept kitchen that flows seamlessly into the inviting family room and out to a covered patio. Perfect for hosting gatherings or enjoying Florida’s beautiful weather. Upstairs, you’ll find two luxurious owner’s suites along with a cozy loft area, offering ample space for rest and privacy. Every detail of this home is crafted to create unforgettable experiences for family and guests alike. Located in the highly sought-after Storey Lake Resort, residents and guests enjoy access to resort-style amenities including a sparkling pool, golf, fitness center, and clubhouse. Just 12 minutes from Walt Disney World Resort, this property is perfectly positioned in a prime short-term rental community, making it an outstanding investment opportunity or dream vacation home.

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

Listing Agent: Nayi Torres (407-720-9585)

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: Imagine owning a vacation home just minutes from Walt Disney World, where unforgettable family memories and investment potential come together in one incredible opportunity. Located in the highly sought-after Oakwater Resort, this fully furnished 3-bedroom, 2-bath condo is turnkey and ready to enjoy from day one. Spend your mornings overlooking the peaceful lake from your private balcony and your afternoons enjoying resort-style amenities including a pool, spa, fitness center, playground, clubhouse, and sports courts. Whether you're looking for a successful short-term rental, vacation retreat, or full-time residence, this property offers exceptional flexibility. The open floor plan, updated flooring, stainless steel appliances, and private garage make ownership easy, while the location places you minutes from Disney, dining, shopping, golf, and entertainment. Oakwater Resort's prime location helps drive strong year-round rental demand, creating an excellent opportunity for consistent monthly income and revenue potential.

Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)

Listing Agent: Jabir Ahmed (407-738-3538)

Remarks: Discover this beautifully upgraded 3-bedroom, 2.5-bath townhome located in one of Central Florida’s most sought-after gated communities. Formerly the builder’s model home, this residence showcases premium finishes throughout, including granite countertops, stainless steel appliances, and elegant wall and ceiling trim details. The open-concept main level offers a seamless flow between the kitchen, dining area, and spacious living room, creating an ideal setting for both everyday living and entertaining. A well-appointed half bath on the first floor adds convenience for guests. Upstairs, the primary suite provides a comfortable retreat with a walk-in closet and an ensuite bathroom featuring dual vanities and quartz countertops. Two additional bedrooms, a full bathroom, and a conveniently located laundry closet complete the second floor. Residents enjoy access to resort-style amenities, including a community pool, fitness center, dog park, playground, and a unique hedge maze. Ideally located just minutes from Walt Disney World, Lake Buena Vista, The Loop, and Orlando International Airport, with easy access to Osceola Parkway, I-4, and SR 417. Shopping, dining, and daily conveniences such as Target are all nearby.

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Xiaoyu Su (352-216-1257)

Remarks: Are you looking for the perfect townhome ? If you are, then look no further than this beautiful center-unit that enjoys a peaceful nature reserve view from the back porch. This spacious home offers 3 bedrooms and two full and one half baths. On the first floor you will enjoy beautiful ceramic floors in the spacious great room along with the kitchen and half bath. The kitchen has a nice size pantry, good cabinet spaces, Stainless Steel Appliances, Granite Counter Tops and best of all it is conveniently located right by the back door leading to the garage, making it very easy for bringing in the groceries. On the second floor, the Owner's Suite features a spacious walk-in closet and its ensuite bathroom offers a large walk in shower, double sinks with a Granite Top, a private Water Closet and a linen closet. Also on the second floor are the two additional bedrooms, the secondary bathroom and the laundry closet. Window blinds and all appliances convey with the sale. Cypress Cay is a beautiful townhome community in the heart of Kissimmee, with energy efficient features, built-in Smart Home Technology and HOA amenities that include a pool & cabana, a playground, half-court basketball court, dog park, walking trails and a fiber network providing up to 1 Gigabit internet speed. Welcome Home to this beautiful, like new home that is located directly across the street from the Community's Amenities mentioned above! The community's location offers convenient access to I-4, the 417 Highway that provides quick access to the Orlando International Airport and the shopping Center at the Loop is just minutes away. Cypress Cay is also very close to Disney, Old Town, Sea World and Universal. Closing costs available! Call to schedule your private viewing today!

Listing is courtesy of: THE KLR GROUP LLC (407-814-3293)

Listing Agent: Claudia Devieux (305-417-1594)

Remarks: PRICE IMPROVEMENT - Beautifully maintained home featuring major upgrades and energy-efficient enhancements. The property boasts a metal roof installed in 2019 and a brand-new A/C system (2025), offering peace of mind for years to come. The pool has been resurfaced and includes an electric pool heater, perfect for year-round enjoyment, all within a fully fenced backyard for added privacy. Significant investment has been made with solar panels which will be paid off by the seller. Appliances are in excellent condition and many are newer, including a washer (2025), dryer, stove (2021), and refrigerator (2025) with water filtration system. Appliances may be transferable under warranty for added buyer benefit. This property is a great combination of functionality, efficiency, and outdoor enjoyment—ideal for buyers looking for long-term value and low-maintenance living

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

Listing Agent: Jennifer Recio (917-891-2028)

Remarks: Welcome to a turn-key opportunity in the highly sought-after Villas at Seven Dwarfs, where location, flexibility, and comfort come together. Great 4 Bedroom, 3 Bathroom Townhome in Villas at Seven Dwarfs. Step into this freshly painted and stylish, short distance to all the great amenities, one of Kissimmee’s premier short-term rental communities. This property is perfectly designed for investors seeking a turn-key vacation rental near Orlando’s world-class attractions and families wanting to live at ease by all the wonderful attractions. New smoke detectors. The kitchen, dining, and living areas flow seamlessly together.**Brand-new Washer & Dryer,**New HVAC system,**New Hot Water Heater for reliable year-round comfort. The spacious layout features a welcoming open-concept living area, a first-floor primary suite for added guest convenience features a large garden tub, and three additional bedrooms (one being a second primary bedroom option) that comfortably accommodates larger groups. In the hallway upstairs, a sink area tucked away. With its tasteful upgrades and resort-style finishes, this home is truly rental-ready. Guests will love the community amenities, including a resort-style pool, clubhouse, tiki bar, fitness center, playground, tennis and basketball courts, and more. Just minutes from Walt Disney World, Universal Studios, and premium shopping and dining, this location ensures strong occupancy and repeat bookings. Whether you’re looking to maximize income potential or add a fully updated property to your short-term rental portfolio, this townhome is the ideal investment. Call today to view your private tour!

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-891-1220)

Listing Agent: Sherry Feck (720-980-0725)

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: SHORT-TERM RENTAL APPROVED. FULLY FURNISHED.LOW HOA. Welcome to Club Cortile, a gated resort-style community ideally located in the heart of Kissimmee just minutes from Disney, shopping, dining, entertainment, and major highways. Whether you're searching for a PRIMARY RESIDENCE, VACATION HOME, or INCOME-PRODUCING INVESTMENT PROPERTY, this spacious 3-bedroom, 2-bathroom first-floor condo offers exceptional flexibility and value. Beautifully maintained and recently painted, the home has been meticulously cared for and is move-in ready. The open floor plan provides comfortable living and entertaining space, while the private SCREENED-IN BALCONY with NO REAR NEIGHBORS creates a peaceful setting to relax and unwind. Additional updates include a NEW HVAC SYSTEM installed in 2024, providing added peace of mind for years to come. The property is being sold FULLY FURNISHED, making it ideal for immediate occupancy or rental use. Residents and guests of Club Cortile enjoy access to RESORT-STYLE AMENITIES including a COMMUNITY POOL, CLUBHOUSE, FITNESS CENTER, TENNIS COURTS, PLAYGROUND, and beautifully maintained grounds. Opportunities to own a well-maintained 3-bedroom condo in a gated community with SHORT-TERM RENTAL FLEXIBILITY, LOW HOA FEES, and such a prime location near Orlando's world-famous attractions are becoming increasingly difficult to find. Schedule your private showing today.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Wilfred Sierra Sosa, Pa (863-588-8303)

Remarks: Welcome to 2518 Empress Drive, a fully upgraded, luxury-inspired residence located within the highly desirable gated community of Tapestry in Kissimmee. Built in 2020 and extensively enhanced with high-end finishes and custom outdoor living upgrades, this exceptional 4-bedroom, 2.5-bath home delivers the lifestyle, design, and presentation typically associated with significantly higher-priced properties. Positioned on a premium corner lot, the home immediately impresses with its modern elevation, expansive paver driveway, and oversized 3-car garage. Inside, the open-concept layout showcases elevated contemporary finishes, oversized tile flooring, upgraded lighting, designer accent walls, and expansive living spaces thoughtfully designed for both everyday comfort and upscale entertaining. The true showpiece of the property is the spectacular resort-style backyard, representing approximately $200,000 in custom improvements and curated outdoor enhancements. Designed to rival luxury vacation retreats, the outdoor living experience features a heated saltwater pool with modern architectural lines, premium hardscaping, artificial turf accents, custom lounge areas, covered lanai, pergola, summer kitchen, wood-paneled ceiling detail, integrated entertainment space, and multiple gathering areas designed for seamless indoor-outdoor living year-round. The gourmet kitchen overlooks the main living and outdoor entertaining areas, creating an ideal setting for hosting guests while maintaining functionality and flow. Upstairs, the spacious primary suite offers a private retreat complete with a beautifully upgraded bathroom and oversized custom walk-in closet. Additional bedrooms provide flexibility for family, guests, office space, or lifestyle needs. Every detail of this home has been thoughtfully designed to create a polished, move-in-ready experience that blends modern elegance with resort-style comfort. Residents of Tapestry enjoy access to resort-inspired community amenities including a clubhouse, fitness center, community pool, parks, and recreational areas, all conveniently located near premier shopping, dining, major highways, and Central Florida attractions. This is a rare opportunity to own a highly upgraded, entertainer-focused home offering luxury presentation, exceptional outdoor living, and turnkey sophistication without the million-dollar price tag. Schedule your private showing today via Showingtime.

Listing is courtesy of: CENTURY 21 BE3 (727-596-1811)

Listing Agent: Tom Vitale (407-922-9934)

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: Welcome home to this beautifully designed, low maintenance townhouse that perfectly balances style and convenience. Rare Opportunity. Pristine former model home in the Guard-Gated Community of Tapestry. Experience luxury and peace of mind in this meticulously maintained home, designer-upgraded townhouse. As a former model home, this property boasts premium finishes and has been kept in impeccable condition- never used as a rental and ready for its new owners. Open Concept living, the spacious floor plan seamlessly connects the living, dining, and kitchen areas, making it perfect for entertaining. Located in the heart of Kissimmee, the Tapestry community offers an active, resort-style lifestyle. Prime location: just minutes away from world class shopping, dining, top rated schools, and the excitement of Disney and Orlando's world-famous theme parks. Do not miss the opportunity, SCHEDULE YOUR VISIT TODAY!!!

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

Listing Agent: Alexandra Cana (407-364-3578)

Remarks: Welcome to 320 Ballo Drive in BellaVida Resort, where space, comfort, and resort style living come together in a beautifully designed 6 bedroom, 4 bathroom pool home with tranquil water views. Built in 2019 and offering nearly 2,900 square feet, this two story residence stands out with a layout that feels both spacious and functional, making it equally appealing as a primary residence, vacation home, or income producing investment. From the moment you enter, the home opens into a bright and inviting main living area designed for gathering, with generous living and dining spaces that flow seamlessly into the kitchen. Here, you will find rich solid wood cabinetry, solid surface countertops, stainless steel appliances, pantry storage, and a large island with bar seating that anchors the heart of the home. Oversized sliding glass doors draw your eye straight to the screened pool and water view, creating the kind of indoor outdoor connection buyers love. The first floor primary suite offers a private retreat with a spacious bedroom, natural light, and an en suite bath with dual sinks, an extended vanity, and glass enclosed shower. A second first floor bedroom and nearby full bath add flexibility for guests or multigenerational living. Upstairs, the home continues to impress with four additional bedrooms, two full bathrooms, a dedicated laundry room, and a large loft that is more than just bonus space. It is a true second living area, ideal for a media room, game room, or lounge. Outside, the screened pool area is a standout feature. With an expansive deck, room to relax and entertain, and peaceful water views stretching beyond the enclosure, the backyard setting feels open, bright, and made for enjoying Florida living. BellaVida Resort adds even more value with its gated entrance, clubhouse, resort style pool, fitness center, basketball and volleyball courts, walking trails, and scenic lake, all in a location close to shopping, dining, and the attractions along US 192. This is the kind of home that delivers size, versatility, and lifestyle all in one.

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

Listing Agent: Peter Luu (321-917-7864)