Kissimmee Homes For Sale & Real Estate - 3396 homes

Remarks: Welcome to this stunning 2-bedroom, 2.5-bath townhome in the sought-after community of Regal Oaks. Perfectly situated with direct access to the serene courtyard garden, this home offers peaceful views and a unique connection to nature—deer are often seen roaming just beyond your private lanai. The outdoor living space is an entertainer’s dream, featuring a private hot tub, grill, and spacious lanai overlooking the lush garden. Just a short walk away, you’ll enjoy the resort-style community pool and amenities. Inside, the home is beautifully updated and thoughtfully decorated with tasteful, modern finishes that create a warm and inviting atmosphere. From the open-concept living area to the stylish kitchen and comfortable bedrooms, every detail has been designed to please. This property is rental ready—whether you’re looking for a personal retreat, vacation home, or investment opportunity, this townhome is the perfect choice. Key Features: - 2 Bedrooms / 2.5 Bathrooms - Private lanai with hot tub & grill - Peaceful courtyard garden views with wildlife sightings - Walking distance to the pool and resort amenities - Beautifully updated interior with tasteful décor - Rental ready for immediate income potential Don’t miss your chance to own this exceptional townhome in Regal Oaks!

Listing is courtesy of: BETTER HOMES & GARDENS LIFESTYLES REALTY (904-853-6386)

Listing Agent: Paula Casey (689-288-5163)

Remarks: Welcome to your dream vacation and stunning fully furnished 5 bedroom, 4 bathroom pool home located on a corner lot in the highly sought after Windsor at Westside Resort. Perfectly designed for indoor/outdoor entertaining and is excellent income producing short-term rental or a fantastic personal retreat. Designed with lots of space in mind this two story layout and open floor plan is the perfect getaway. The home sleeps up to 14 comfortably and features large living areas with plenty of space for relaxing. The first floor master bedroom offers privacy and space, the kitchen has granite countertops and stainless steel appliances with a nice island opening to the dining room and living space. Enjoy the gated resort style amenities with the zero entry point pool, water slide, lazy river, and water playground. It boasts a clubhouse, a lake with a pier, fitness center, volleyball courts, sundry shop and video arcade. This is an ideal location as it offers easy access to Disney World attractions and many other theme parks in the area. Welcoming any and all offers.

Listing is courtesy of: BEACHES WITHIN REACHES REALTY (386-864-3154)

Listing Agent: Abby Baker (386-864-3154)

Remarks: PRICE IMPROVED!!!!! Exceptional Investment Opportunity in the Heart of Kissimmee! This fully remodeled 2-bedroom, 2-bathroom second-floor condo is a turnkey income-producing property ideally suited for short-term rentals, long-term leasing, or a vacation home investment. With everything completely updated, this unit requires minimal upfront capital—allowing for immediate rental readiness and optimized returns. Strategically located just minutes from world-famous theme parks, shopping, dining, and major attractions, this property benefits from consistent high rental demand year-round. Its prime location makes it highly attractive to both vacation renters and long-term tenants. The community offers desirable amenities including a resort-style pool and fitness center, enhancing guest experience and increasing occupancy potential. Key Investment Highlights: Fully renovated – no deferred maintenance Strong short-term and long-term rental potential High-demand tourist corridor location Low-maintenance condo ownership Excellent opportunity for cash flow and appreciation Whether you are expanding your portfolio or entering the Central Florida market, this property delivers a compelling combination of location, condition, and income potential.

Listing is courtesy of: MP FLORIDA PROPERTY & REALTY INC (954-701-0824)

Listing Agent: Evelyn Figueroa (407-724-1846)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom townhouse offering 1,468 sq.ft of well-designed living space in the sought-after Fiesta Key community. Fully furnished and turn-key, this property is ideal as a short-term rental investment, vacation home, or full-time residence. What truly sets this home apart are the TWO fully renovated upstairs bathrooms – a rare upgrade in Fiesta Key. Both full bathrooms have been completely remodeled with modern finishes, updated showers, contemporary fixtures, and a clean, stylish design that today’s buyers and guests appreciate. Most comparable units in the community still feature original bathrooms, making this a significant value advantage. The main floor features an open-concept layout with living room, dining area, and kitchen, all complemented by durable laminate flooring. The kitchen is fully equipped and ready for owner use or guest stays. A convenient half bath downstairs adds functionality for entertaining. Upstairs, all three bedrooms provide privacy and comfort. The primary suite includes an updated en-suite bathroom with a modern shower, creating a fresh and inviting retreat. The additional full bathroom has also been completely renovated, offering consistency in quality throughout the home. Step outside to your private back porch with tranquil pond views — the perfect setting to relax after a day at the parks. Recent upgrades include: Two fully renovated upstairs bathrooms, New AC (2018), New water heater (2023). Fiesta Key offers resort-style amenities including a clubhouse, fitness center, community pool, and tennis courts. Located just minutes from Disney, shopping, dining, and major highways, this property checks all the boxes for investors and lifestyle buyers alike. Move-in ready and rental ready — with upgrades that truly make it stand out from the competition.

Listing is courtesy of: HOPKEY REALTY (407-454-1217)

Listing Agent: Uno Sorlie (407-454-1217)

Remarks: Fully renovated and move-in ready 3-bedroom, 2-bath condo located in the desirable Gables at Lakeside community. This spacious second-floor unit offers a private entrance and peaceful pond views, creating the perfect setting to relax and unwind. Inside, you’ll find a bright and open layout with modern updates throughout, providing comfort and functionality for everyday living. The community features excellent amenities including a swimming pool, fitness center, tennis court, clubhouse, playground, and more — all within a quiet and well-maintained environment. Conveniently located in the heart of Kissimmee, just minutes from shopping, dining, major roadways, and The Loop. Whether you’re looking for a primary residence or an investment opportunity, this property offers both value and location. Schedule your private showing today.

Listing is courtesy of: CAINANBA LLC (407-724-4173)

Listing Agent: Cainan Almeida (407-724-4173)

Remarks: Your own private getaway at 3222 Cupid Place, a stunning 4-bedroom, 3-bathroom townhome in the prestigious gated community of West Lucaya Village. This fully furnished home is tailored for the high-demand short-term rental market, offering a perfect mix of modern style and practical comfort. Ideally situated in the heart of the tourist corridor, you’re just a short drive from Walt Disney World’s gates, as well as the vibrant dining options, championship golf courses, and luxury shopping that define Central Florida. Outside, the West Lucaya Village resort lifestyle offers a range of impressive amenities. Guests and owners can relax by the swimming pool and jacuzzi, stay active in the modern fitness center, or enjoy the clubhouse game room and kids’ play area. The community also includes a basketball court and scenic picnic spots for outdoor gatherings. Whether you’re seeking a high-performing addition to your investment portfolio or a dream vacation home that pays for itself, this property delivers on all fronts.

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: James Donovan (407-705-2616)

Remarks: Positioned along the storied shoreline of Lakeshore Boulevard, this rare income-producing property and location captures the timeless character of Historic Downtown Kissimmee with an address that places lifestyle, recreation, and long-term upside in one compelling package. Comprising six separate income producing apartments, 4 furnished and 2 unfurnished, with a total of 9 bedrooms and 6.5 baths. Property presents a remarkable opportunity for investors seeking immediate rental income or the possibility of a boutique hotel location in one of Central Florida’s steadily evolving waterfront corridors. Originally constructed in 1930, the building carries an architectural presence rarely replicated today blending vintage charm, and an unmistakable sense of place with views and walkability that continue to drive tenant demand. Situated directly across from Kissimmee Lakefront Park, residents enjoy effortless access to the marina, waterfront trails, fishing pier, playgrounds, amphitheater events, dining, cafés, and downtown entertainment all without relying on a car. The building spans over 4,100 square feet on an oversized corner-style lot and features private parking, scenic water and park views, and a setting surrounded by mature trees and historic homes that give the neighborhood its distinctive identity. The property’s layout creates unlimited opportunities. Downtown Kissimmee continues attracting attention for its lakefront revitalization, expanding SunRail connectivity and tourism corridor. Assets with authentic architectural appeal and irreplaceable positioning near the waterfront are becoming increasingly difficult to secure particularly those offering multi-unit versatility near the city’s cultural core. For the discerning investor, this is legacy-style holding in one of Kissimmee's most recognizable districts, where historic ambiance, waterfront surroundings, and enduring rental appeal converge.

Listing is courtesy of: ROMAN'S PRO REALTY LLC (407-610-1970)

Listing Agent: Petie Bilyk (407-361-1415)

Remarks: Beautiful and fully furnished home, featuring 4 beds and 3 baths, located in the highly desirable Storey Lake community! This home is move-in or rental ready. Enjoy resort-style amenities including a clubhouse, fitness center, multiple pools, lazy river, water slides, sports courts, and more. Conveniently situated just 25 minutes from Orlando International Airport, Just minutes from Disney World, Universal Studios, shopping outlets, and top dining options. Whether you're looking for a short-term rental investment or a vacation retreat, this property offers the perfect opportunity in one of Central Florida’s most sought-after locations. Buyer's responsibility to confirm all information is accurate with the HOA.

Listing is courtesy of: TALENT REALTY SOLUTIONS (407-910-2020)

Listing Agent: Nicole Duque Estrada Almeida Pereira (813-215-7422)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Short Sale. **Discover PEACEFUL LIVING in this move-in-ready 3-bedroom, 2-bathroom single-story home, offering over 1,800 SQUARE FEET of comfortable space in a QUIET, RURAL setting away from the hustle and bustle. Set in a safe, serene neighborhood with a LOW HOA, this home features a welcoming front LANAI-STYLE PORCH that opens to a light-filled foyer with VAULTED CEILINGS. Inside, you'll find a thoughtful layout that includes both a separate Living Room and Dining Room, offering FLEXIBLE SPACES for entertaining, relaxing, or hosting special gatherings. The split floor plan ensures privacy, with the Primary Suite on one side of the home, boasting a WALK-IN CLOSET and an en suite bath with dual sinks, a GARDEN TUB, and a separate shower. On the opposite side, two additional bedrooms share a full bath, ideal for family or guests.The heart of the home is a SPACIOUS KITCHEN with vaulted ceilings, wood cabinetry, stone countertops, a breakfast bar, and a generous pantry, all flowing seamlessly into the open Family Room. WOOD-LOOK LAMINATE flooring enhances the main living areas and Primary Suite, combining durability with style. Step through sliding glass doors to the screened back porch, where a HOT TUB invites relaxation as you take in the peaceful surroundings. The 2-car garage adds convenience, and the community offers desirable AMENITIES including a pool, community center, fitness facility, parks, and year-round events.While this home offers a QUIET ESCAPE, you’re still close to everything you need—local shopping, schools, dining, and recreation. For nature enthusiasts, you're less than 5 minutes from hiking trails at BELLINI PRESERVE, or enjoy an easy 30-minute drive to DISNEY parks, and QUICK ACCESS to other major Central Florida attractions and highways, making this the perfect blend of tranquility and convenience. Don’t miss the opportunity to make this Florida retreat your own!

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

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

Remarks: Short Sale. Short Sale. Third-party lender approval required. Vacant residential townhome sold as-is. Seller and listing broker make no representations or guarantees regarding lender approval or time frame. Buyer to verify all information and conduct due diligence. Nestled in Kissimmee, Florida, is this 3-bedroom, 2.5-bathroom Airbnb-approved townhome offering beautiful views and access to a community pool. Featuring a spacious open-concept living area, a fully equipped kitchen, full-size washer and dryer in a separate laundry room, plus ample storage, this home is perfect for comfortable living, a vacation retreat, or use as a short-term rental. Enjoy a private patio overlooking the lake with shopping, dining, and parks just minutes away. With a motivated seller and priced to sell, this property presents an incredible opportunity for investors and homeowners alike. Don’t miss the chance to make this versatile townhome yours!

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

Listing Agent: Lesly Hijar (321-347-7383)

Remarks: Fully furnished, beautifully decorated, 6Bed/4.5Bath vacation home with brand new roof, quartz countertops, new luxury plank flooring, themed rooms, and screened in pool. Perfectly situated in the coveted vacation community of Crystal Cove Resort; with excellent amenities including clubhouse, gym, community pool, and playground. Ideal for any investor looking for a family vacation residence or short-term rental investment. All while, easy access to major highways, theme parks, shopping, dining, and the Orlando International Airport.

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

Listing Agent: Victor Nguyen (407-721-1032)

Remarks: Excellent opportunity to own a hotel unit in one of Central Florida’s most visited areas. Just minutes away from Walt Disney World, ESPN Wide World of Sports, and Disney’s Hollywood Studios, this unit is ideally positioned to attract year-round visitors. The surrounding area is filled with popular restaurants, outlet shopping, and entertainment options, all with easy access to main roads and highways. This is a great opportunity for investors seeking steady passive income. The property is part of a professionally managed hotel, where all guest services, maintenance, and bookings are handled on-site, offering a truly hands free ownership experience. Its location makes it highly desirable for short-term stays year-round.

Listing is courtesy of: RE/MAX REX (561-220-1520)

Listing Agent: Ana Armua (954-225-2979)

Remarks: Excellent opportunity to own a hotel unit in one of Central Florida’s most visited areas. Just minutes away from Walt Disney World, ESPN Wide World of Sports, and Disney’s Hollywood Studios, this unit is ideally positioned to attract year-round visitors. The surrounding area is filled with popular restaurants, outlet shopping, and entertainment options, all with easy access to main roads and highways. This is a great opportunity for investors seeking steady passive income. The property is part of a professionally managed hotel, where all guest services, maintenance, and bookings are handled on-site, offering a truly hands free ownership experience. Its location makes it highly desirable for short-term stays year-round.

Listing is courtesy of: RE/MAX REX (561-220-1520)

Listing Agent: Ana Armua (954-225-2979)

Remarks: Under Construction. Evergreen presents the Pearson. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen, dining area and a living room overlooking a covered patio. The well-appointed kitchen features an island with bar seating, plentiful cabinets, counter space and stainless steel appliances, making entertaining a breeze. As we head upstairs, you are greeted with a landing area and linen closet. Bedroom one is located just off the landing area and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. This popular townhome features a single car garage at the front of the home. Like all homes in Evergreen, the Pearson includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)

Listing Agent: Stephen Cline (407-250-7299)

Remarks: Beautiful Townhome for Sale! Welcome to this Pristine 3-bedroom, 2.5-bathroom townhome featuring a spacious layout and thoughtful design. The first floor boasts elegant ceramic tile flooring, while the second floor offers cozy carpeting throughout. An attached 1-car garage provides added convenience. Upstairs, you’ll find the laundry area for easy access and functionality. Located in a desirable community close to shopping centers, hospitals, restaurants, Disney World, and a variety of outdoor activities. Enjoy quick access to major roadways including US-192, I-4, Highway 27, and SR-429. The Orlando International Airport is also just a short drive away. No CDD Fees! Don't miss out on this fantastic opportunity—schedule your showing today!

Listing is courtesy of: REILE REALTY CORP (321-299-5123)

Listing Agent: Reina Mendez (321-299-5123)

Remarks: One or more photo(s) has been virtually staged. Experience elegant resort-style living in this stunning Venetian Model located in the award-winning 55+ community of Solivita’s highly sought-after Bella Viana neighborhood. This beautifully designed 3-bedroom, 3.5-bath residence offers an exceptional blend of comfort, space, and sophistication with soaring vaulted ceilings, tray ceilings, a desirable split floor plan, and a versatile bonus room perfect for a home office, den, craft room, or additional flex space.Designed for both entertaining and everyday living, the gourmet kitchen features Corian countertops, double ovens, a glass-top range, microwave, double-door refrigerator, and an inviting breakfast nook overlooking the tranquil pond views. The formal dining area with elegant pendant lighting creates the perfect setting for gatherings with family and friends. Step through the glass doors onto the spacious lanai and enjoy peaceful mornings with coffee while taking in the serene waterfront setting and Florida wildlife.The expansive primary suite serves as a private retreat with two walk-in closets, dual vanities, linen storage, and a luxurious garden tub with separate shower. Spacious guest bedrooms, with their own bathrooms, provide comfort and privacy for visitors, while the well-equipped laundry room with built-in cabinetry and utility sink leads to the oversized 3-car garage.Beyond the home itself, Solivita offers an unmatched lifestyle filled with world-class amenities and endless opportunities for recreation and connection. Residents enjoy 14 resort-style pools, two championship 18-hole golf courses at Stonegate Golf Club, tennis and pickleball courts, softball fields, bocce ball, fitness centers, spas, walking trails, restaurants, art studios, social clubs, dog parks, community gardens, and over 200 clubs and activities. The gated, golf-cart-friendly community is guarded 24 hours a day and ideally located near Orlando’s premier shopping, dining, entertainment, and attractions including Disney, SeaWorld, and more.This is more than just a home — it’s a lifestyle. Schedule your private showing today!

Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)

Listing Agent: Corey Smallman (407-744-2765)

Remarks: Welcome to your next lucrative investment or dream vacation getaway at 276 Southfield St, nestled within the highly sought-after, guard-gated community of Encore at Reunion. This fully furnished 4-bedroom, 3-bathroom home is thoughtfully designed for effortless short-term rentals or high-end seasonal living. Step inside to find a welcoming, meticulously maintained interior featuring new plush carpeting and a stylish new living room couch perfect for relaxing after a day at the parks. The garage has been expertly transformed into an action-packed gaming area, promising endless entertainment for guests of all ages. Outside, your private tropical oasis awaits, complete with a pristine pool and spa. Best of all, you can buy with ultimate peace of mind, backed by a brand-new pool heater with a 3-year warranty. Location and resort lifestyle are everything in the Central Florida market, and this property delivers on both fronts. Encore at Reunion boasts world-class luxury resort amenities, including a spectacular 10-acre water park with thrilling water slides, a massive community pool with private cabanas, a state-of-the-art fitness center, tennis and basketball courts, and on-site dining options like Finns Restaurant and the Shark Lounge. Positioned just minutes from Walt Disney World, Universal Orlando, and SeaWorld, this property offers complimentary resort shuttle service to the major theme parks, plus seamless access to premier dining, championship golf, and endless shopping. Whether you are looking to generate rental income as a savvy investor or claim your own magical piece of Florida sunshine, this property is completely ready to perform from day one.

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: James Donovan (407-705-2616)

Remarks: LIKE NEW – in Pristine Condition! Welcome to this beautifully designed open-concept townhome where the living, dining, and kitchen spaces flow seamlessly—perfect for everyday living and entertaining. The chef-inspired kitchen features quartz countertops, 42” upper cabinets, and sleek stainless-steel appliances. Enjoy the upgraded first floor with elegant laminate flooring and soaring 9-foot ceilings throughout. The spacious primary suite offers the ultimate retreat with a dual vanity en suite, quartz countertops, and a generous walk-in closet. A thoughtful split-bedroom layout ensures privacy and convenience for family or guests. Step outside to your covered lanai with direct access to the community pool—perfect for year-round Florida living! Community Highlights: Low HOA & No CDD Fees Just 4 miles to Medical City & Boxi Park 9 miles to Orlando International Airport 22 miles to Disney Parks This move-in-ready home combines modern style, efficiency, and unbeatable location. Don’t wait—schedule your private showing today!

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

Listing Agent: Elias Kilci (407-970-8124)

Remarks: Welcome to this exceptional 7-bedroom, 5-bathroom vacation home located in the highly desirable Windsor at Westside Resort. This fully furnished property is turn-key and revenue-ready, offering a spacious and well-designed floor plan ideal for large families and short-term rental guests. The home features an open-concept main living area, a generous upstairs loft, a 2-car garage, and a private screened-in pool with heated spa for year-round enjoyment. The kitchen offers stainless steel appliances, stone countertops, and a large island with seating, flowing seamlessly into the dining and living spaces. With ample bedrooms—including multiple suites—and thoughtfully designed themed rooms, this residence provides comfort and functionality for owners and guests alike. Located within one of Orlando’s top short-term rental communities, Windsor at Westside offers outstanding resort amenities such as a full-service clubhouse, resort-style pool with lazy river, fitness center, tennis and basketball courts, sand volleyball, arcade, restaurant, and 24-hour gated security. Just minutes from Disney and Central Florida’s world-class attractions, this property is an excellent opportunity for investors or buyers seeking a high-performing vacation retreat.

Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)

Listing Agent: Rubens Aranha (407-308-9094)

Remarks: Welcome to this exceptional, fully furnished vacation home located in the highly sought-after resort community of Storey Lake Resort in Kissimmee, Florida. Situated at 2876 Simile Street, this spacious 8-bedroom, 5-bathroom luxury home offers over 4,300 square feet of beautifully designed living space, making it the perfect short-term rental investment, vacation retreat, or second home opportunity just minutes from Orlando’s world-famous attractions. Built in 2022, this modern home features an open-concept floor plan designed for entertaining large groups and maximizing vacation rental income potential. The expansive living and dining areas flow seamlessly into a stylish gourmet kitchen with oversized island seating, ample cabinetry, and plenty of space for guests and family gatherings. The home also features a dedicated first-floor game room along with a spacious upstairs loft media and entertainment area, creating multiple spaces for relaxation and fun for guests of all ages. One of the standout features of this property is the beautiful water view backyard with no rear neighbors, offering added privacy and a peaceful resort-style setting. Step outside to enjoy your own private screened-in pool and patio area — the perfect place to unwind after a day at Disney or enjoy Florida’s year-round sunshine. The home showcases beautifully themed bedrooms with classic custom designs that create a memorable vacation experience and elevate the property’s appeal in the short-term rental market. Every detail has been thoughtfully designed to provide both luxury and comfort, making this property highly attractive for vacation guests and large family gatherings. Located within Storey Lake Resort, owners and guests enjoy access to world-class resort amenities, including a resort-style swimming pool, lazy river, water slides, splash pad, fitness center, clubhouse, mini golf, sports courts, kayak rentals, tiki bar, and multiple recreational areas. Storey Lake remains one of Central Florida’s premier vacation resort communities due to its prime location and outstanding amenities. The location is unbeatable — only minutes from Walt Disney World, Disney Springs, Universal Studios, SeaWorld, premium outlet shopping, golf courses, restaurants, and Orlando International Airport. With strong year-round tourism demand and one of the best resort locations in Central Florida, this property offers incredible investment potential and lifestyle value. Whether you are looking for a high-performing income-producing property or a luxury vacation getaway for your family and guests, 2876 Simile Street offers the perfect combination of location, privacy, resort amenities, and vacation home luxury in the heart of Central Florida.

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

Listing Agent: Anna Shi (407-216-1215)