Kissimmee Real Estate

Kissimmee Real Estate

Kissimmee: A Vibrant City in the Heart of Florida

Nestled in the heart of Florida, Kissimmee is a vibrant city that offers a perfect blend of natural beauty, entertainment, and a thriving real estate market. Located in the sunshine state of Florida, Kissimmee is a part of Osceola County, known for its warm climate and friendly community.

One of the main attractions of Kissimmee is its close proximity to world-renowned theme parks such as Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando. These attractions draw millions of visitors every year, making Kissimmee a popular destination for both tourists and residents alike.

Apart from its proximity to theme parks, Kissimmee boasts a variety of outdoor recreational opportunities. With its numerous lakes, Kissimmee is a haven for water enthusiasts, offering activities such as boating, fishing, and water sports. The city also features several golf courses, parks, and trails for those who enjoy the great outdoors.

Kissimmee's real estate market is thriving, with a range of housing options to suit every lifestyle and budget. From spacious single-family homes to modern apartments and condos, there is something for everyone in Kissimmee. The city's diverse neighborhoods offer a mix of suburban tranquility and urban convenience, making it an attractive choice for families, professionals, and retirees.

With its prime location, vibrant entertainment scene, and thriving real estate market, Kissimmee is a city that offers the best of both worlds. Whether you're looking for a vacation home, an investment property, or a place to settle down, Kissimmee has it all. Explore the opportunities that await you in this thriving city in the heart of Florida.

Newest Listings in Kissimmee

2 Beds ⋅ 2 Baths ⋅ S5155278 MLS

Welcome to 1374 Boulder Dr, a well-maintained 2-bedroom, 2-bath home offering 1,063 sq. ft. of comfortable living space in the desirable Pebble Creek area of Kissimmee. Whether you are a first-time homebuyer looking for an affordable place to call home or an investor searching for a great opportunity in a convenient Central Florida location, this property offers excellent potential. Built in 1984 with continuous footing construction, the home features a 2024 HVAC system, 2017 roof, and 2017 water heater. Its ready to move in, minimalist style provides a blank canvas ready for you to personalize and make your own. Best of all NO HOA and NO CDD! Enjoy an excellent location just approximately 5 minutes from Walmart near Osceola Parkway and Michigan Avenue, Florida’s Turnpike, and Valencia College, with convenient access to shopping, dining, schools, and major roadways. A great combination of location, affordability, flexibility, and investment potential. schedule your showing today!

1374 Boulder Drive, Kissimmee

3 Beds ⋅ 2 Baths ⋅ O6429993 MLS

A fresh new look, a peaceful backyard and a location that keeps everyday conveniences within easy reach—2350 Topaz Trail brings it all together. Newly painted inside and out, this move-in-ready 3-bedroom, 2-bath home is located in the desirable Lakeside community. Great investment opportunity as well. The bright, open floor plan features tile flooring throughout and a split-bedroom design that provides added privacy. The spacious primary suite offers a walk-in closet and private bath with dual sinks, a garden tub and separate shower. The kitchen comes complete with appliances, while a new washer and dryer, Nest thermostat and gutters add everyday comfort and convenience. Outside, the vinyl-fenced backyard features a patio and overlooks a peaceful conservation area—creating a private setting for relaxing, entertaining or enjoying the Florida sunshine. A beautiful pond directly across the street further enhances the home’s inviting surroundings. Additional highlights include a 2018 roof and two-car garage. Conveniently located near shopping and dining at The Loop, grocery stores, medical facilities, Osceola Parkway and the Florida Turnpike, with easy access to Orlando International Airport, Lake Nona and Central Florida’s attractions. Reasonably priced to sell quickly, this home offers an excellent combination of condition, location and value.

2350 Topaz Trail, Kissimmee

2 Beds ⋅ 2 Baths ⋅ O6431335 MLS ⋅ 700 BLDG.

Positioned within the highly sought-after Siena at Celebration community, this beautifully maintained 2-bedroom, 2-bathroom condo with a rare 1-car garage offers a light-filled, open floor plan, peaceful lake and golf course views, and the charming lifestyle Celebration is known for. From the moment you step through the front door, you are welcomed by an inviting living space filled with natural light. The thoughtfully designed kitchen is positioned just off the entry and overlooks the main living area, creating an open feel that flows seamlessly into the living room and dining room. At the end of the kitchen, a dedicated laundry room provides added convenience, and the washer and dryer will convey with the sale. French doors off the living and dining area lead to the private balcony, where beautiful lake and golf course views create a peaceful backdrop to enjoy throughout the day. Tucked off the left side of the living room, the spacious primary suite features bamboo laminate flooring, a walk-in closet, and a private en-suite bathroom. The lake and golf course views can also be enjoyed directly from the primary bedroom, and during Celebration’s Fourth of July festivities, you can even watch the fireworks right from your bedroom window. On the opposite side of the condo, the spacious second bedroom offers plenty of room and direct access to the second full bathroom. The bathroom also opens to the main living area, providing convenient dual access for both the bedroom and guests. Laminate flooring flows throughout the living room, dining room, and second bedroom, while tile can be found in the kitchen and both bathrooms. Both bedrooms have also been freshly painted. Additional features throughout the home include new light fixtures, smart light switches that can connect to a security system, a Ring doorbell, and hardwired features. The building itself has also recently been painted and received a new roof. Adding even more convenience is the rare private 1-car garage, with existing shelving that will convey with the sale, as well as an assigned parking space. Residents of Siena at Celebration enjoy access to a resort-style pool, clubhouse, fitness center, and playground. Living in Celebration also grants access to six additional community pools, tennis, basketball, and sand volleyball courts, sports fields for soccer, softball, and lacrosse, and over 26 miles of scenic walking and biking trails throughout town. Located just minutes from Celebration’s vibrant downtown filled with restaurants, shops, and lakeside events, this condo also offers quick access to Celebration Pointe’s grocery store, brewery, and dining options. AdventHealth Celebration is nearby, and Walt Disney World is only about 10 minutes away. With Orlando International Airport approximately 25 minutes from your doorstep and both Florida coasts within reach for easy day trips, this home places you in the center of everything that makes Central Florida living so special. Don’t miss your opportunity to own this beautifully maintained condo with peaceful views and a rare private garage in one of Central Florida’s most beloved and picturesque communities.

700 Siena Palm Drive Unit 302, Kissimmee

4 Beds ⋅ 3 Baths ⋅ S5155340 MLS

Welcome to 2791 Picadilly Circle, Kissimmee, FL — a beautifully updated 4-bedroom, 2.5-bath pool home offering the perfect combination of modern upgrades, generous living space, privacy, and the Florida lifestyle. From the moment you step inside, you’ll appreciate the bright, open floor plan and thoughtfully upgraded interior. At the heart of the home is the updated gourmet kitchen, designed to impress with stylish finishes and an inviting layout perfect for everything from everyday meals to entertaining family and friends. The bathrooms have also been tastefully updated and upgraded, giving the home a fresh, modern feel throughout. With four spacious bedrooms and 2.5 baths, there’s plenty of room to spread out. The versatile living areas provide flexibility for entertaining, working from home, family gatherings, or simply relaxing at the end of the day. Step outside and discover your own private Florida retreat. The fully fenced backyard features a sparkling swimming pool and plenty of space to relax, entertain, barbecue, or soak up the Florida sunshine. Whether hosting weekend gatherings or enjoying a quiet afternoon poolside, this outdoor space is designed to be enjoyed year-round. Conveniently located in the heart of Kissimmee, 2791 Picadilly Circle puts you just minutes from shopping, dining, schools, major roadways, Orlando-area attractions, and everything Central Florida has to offer. Updated gourmet kitchen. Upgraded bathrooms. Four spacious bedrooms. Private fenced backyard. Sparkling pool. Prime Kissimmee location. This home checks all the boxes and is ready for its next owner. Schedule your private showing today and experience everything 2791 Picadilly Circle has to offer!

2791 Picadilly Circle, Kissimmee

6 Beds ⋅ 9 Baths ⋅ S5155280 MLS

Experience resort-style living in this massive pool home, perfect for large families or short-term guests. The chef’s kitchen is built for entertaining, boasting an oversized stone island, dual refrigerators, and dual dishwashers. Melt into the open-concept layout that flows straight out to your private, screened pool deck. With dual primary suites (one on each floor) and a massive upstairs loft, everyone gets their own space. Enjoy 24/7 guard-gated security, premium community amenities, and a prime location minutes from Disney, championship golf, and top Central Florida dining.

222 Marcello Boulevard, Kissimmee

4 Beds ⋅ 4 Baths ⋅ O6432499 MLS ⋅ 1208 BLDG.

Three Stories • Private Pool • Renovated Kitchen • Incredible Bonus Suite Welcome to 1208 Celebration Avenue, where spacious living, thoughtful updates, and the unmistakable charm of Celebration, Florida's South Village come together in one exceptional townhome. This beautiful three-story townhome offers a wonderfully open and flexible floor plan designed for both everyday living and entertaining. The heart of the home is the renovated kitchen, complete with a breakfast nook and additional seating area, creating the perfect gathering place for family and friends. The adjoining living spaces feel open and inviting, while architectural details including trey ceilings give the home an elevated, distinctive look. Upstairs, the spacious primary suite provides a relaxing retreat with a luxurious en-suite bath featuring a jetted tub and an impressive walk-in closet with custom cabinetry. Two additional bedrooms offer plenty of room for family, guests, or a home office. And then there’s the THIRD FLOOR! Nearly 800 square feet of bonus living space with its own full bath opens up a world of possibilities. Create an additional primary or guest suite, home theater, game room, private office, fitness studio—or a combination of them all. It’s the kind of flexible space that makes this home truly stand apart. Step outside and discover your own Rare private pool and patio, an inviting setting for morning coffee, sunny Florida afternoons, entertaining friends, or relaxing at the end of the day. Even the garage has been thoughtfully finished, featuring an organized two-car garage with tiled flooring and decked attic storage with pull down ladder. Wonderful sized apron behind the garage to park additional vehicles. Brand New water heater adds another practical upgrade, and some furnishings may also be available for inclusion. Best of all, you’re living in the heart of Celebration—the town that Disney built—with beautiful parks, community pools, walking and biking trails, neighborhood amenities, dining, shopping, and the Celebration lifestyle all close by. 1208 Celebration Avenue isn’t simply a townhome—it’s three floors of possibilities, your own private Florida pool, and the opportunity to call one of Central Florida’s most beloved communities HOME. Welcome to Celebration. Welcome home.

1208 Celebration Avenue, Kissimmee

3 Beds ⋅ 3 Baths ⋅ O6432346 MLS

Great opportunity for investors or handy buyers! This 5-bedroom, 4-bathroom home features a huge covered patio and offers 1,720 SF of living space in a centrally located Kissimmee neighborhood. The layout includes a galley kitchen with ample storage open to the dining area, a built-in fireplace, and a bonus Florida room for extra living space. The primary bedroom opens via French doors to the patio — great bones and great potential once updated. Home needs TLC throughout; priced accordingly for buyers ready to bring their vision (and toolbox). Large fenced backyard offers room to expand or add value. Close to major roads, shopping, and dining. Sold strictly AS-IS, seller making no repairs. Buyer/buyer's agent to independently verify all information. Cash or renovation financing preferred — schedule your showing and see the potential today!

711 S Emory Avenue, Kissimmee

5 Beds ⋅ 4 Baths ⋅ S5155014 MLS

Welcome to the quintessential Florida lakefront lifestyle. Tucked beneath a breathtaking canopy of majestic Southern Live Oaks, this extraordinary 4-bedroom, 3-bath estate—with a detached 1-bedroom, 1-bath guest house—offers approximately 105 feet of shoreline on beautiful Lake Tohopekaliga (Lake Toho) and a setting unlike anything else on the market. Beyond the private wrought-iron gates off Neptune Road, this 1.5-acre estate offers the privacy and freedom of no HOA, allowing you to keep your boat just steps from the water and your RV on its own dedicated pad with electrical hookup. From the sparkling saltwater pool and tranquil koi pond with cascading waterfall to the countless custom features throughout the property, this is a home that truly must be experienced in person. Built with durable concrete block construction and topped with a newer roof, the residence features a timeless blend of hardwood and tile flooring. The heart of the home is a chef’s kitchen designed for both everyday living and entertaining, complete with custom wood cabinetry, a premium Viking vent hood over a six-burner gas cooktop, and sunset views of Lake Toho from the kitchen sink. The outdoor living spaces are equally impressive. Positioned between the pool area and the lakeshore, the custom outdoor kitchen is an entertainer’s dream, featuring a full brick wood-fired oven, brick rotisserie, brick smoker, and expansive concrete cooking area—perfect for hosting everything from intimate family dinners to large gatherings. The spacious primary suite occupies its own private wing of the home and showcases an entire wall of windows framing spectacular lake views. The en-suite bath includes a relaxing garden tub, separate walk-in shower, generous walk-in closet, and ample space to create your own private retreat. The main residence also offers three additional bedrooms, a dedicated office with a closet that could serve as a fifth bedroom, and thoughtfully designed living spaces throughout. Adding even more versatility is the detached guest house, complete with its own private driveway and rear entrance. Featuring an open-concept living and kitchen area, separate bedroom, full bath, and its own HVAC system, it’s ideal for extended family, guests, a private office, or potential rental opportunities. Despite its peaceful, estate-like setting, this exceptional property is conveniently located just minutes from the rapidly growing NeoCity technology district, Osceola Heritage Park, the Florida Turnpike for easy access throughout Central Florida, as well as the Kissimmee and Amtrak SunRail stations for a convenient alternative to highway commuting. This location is also great for the them park enthusiasts, with over 15 major Disney, Universal, and SeaWorld parks combined within a short drive. For the avid boater/fisherman, you will be delighted to know that your boat- parked on your own dock (with a boat lift)- here on Lake Toho is a part of the Chain-of-Lakes, allowing you to travel through lakes all over Florida, and even to the Atlantic or Gulf of Mexico. Lake Toho also hosts several professional bass fishing tournaments each year. Whether you’re searching for a private waterfront retreat, an entertainer’s paradise, or a place where you can truly enjoy the Florida lifestyle, this one-of-a-kind Lake Toho estate offers an opportunity that’s rarely available.

807 Neptune Road, Kissimmee

4 Beds ⋅ 3 Baths ⋅ S5155398 MLS

Beautifully and completely renovated 4-bedroom, 2.5-bath single-family home in the desirable Enclave at Tapestry community in Kissimmee! This spacious two-story residence features 2,694 sq. ft. of living space and has been thoughtfully upgraded throughout with modern finishes and a fresh, contemporary feel. The main level provides generous living and entertaining areas, while the second floor features spacious bedrooms and a versatile layout for family, guests, or a home office. Enjoy the added benefit of fully paid-off solar panels, providing energy-efficient living with no solar loan to assume. The property also features a 2-car garage, covered and open porch areas, and a generous 6,756 sq. ft. lot. Built in 2017 and extensively renovated, this home combines modern comfort, functionality, and energy efficiency. Conveniently located near major highways, shopping, dining, entertainment, and Central Florida's world-famous attractions. A fantastic opportunity to own a beautifully updated home in a prime Kissimmee location!

3430 Canvas Street, Kissimmee

4 Beds ⋅ 3 Baths ⋅ S5155354 MLS ⋅ 1400 BLDG.

Welcome to 1400 Celebration Avenue, Unit 105, located in the highly desirable Artisan Park community of Celebration! This spacious 3-bedroom, 2.5-bath condominium offers approximately 2,002 square feet of comfortable living space and a private 1-car garage. The well-designed floor plan provides generous living and dining areas, offering plenty of room for everyday living and entertaining. Located within the charming master-planned community of Celebration, residents can enjoy beautiful surroundings, sidewalks, parks, recreational amenities, and the unique lifestyle this community is known for. Conveniently located near shopping, dining, entertainment, major roadways, and Central Florida attractions. A wonderful opportunity to enjoy the Celebration lifestyle in the sought-after Artisan Park community!

1400 Celebration Avenue Unit 105, Kissimmee

5 Beds ⋅ 5 Baths ⋅ S5154949 MLS

This well-maintained 5 bedroom, 5 bath home in the 5-Star Windsor Hills Resort offers buyers a rare opportunity to acquire a proven, income-producing short-term rental just minutes from Walt Disney World—one of the strongest and most reliable vacation-rental corridors in the United States. Designed with the resort’s most desirable 5-bedroom open floorplan, the home consistently attracts large families and multi-generational groups, maximizing both occupancy and nightly rate potential. For buyers seeking immediate continuity of income, the seller is willing to transfer future bookings, allowing a seamless transition with no downtime. Interior Features for High-Demand Guest Use Multiple dining areas and a spacious main living room built to accommodate high guest volume Stainless steel appliances in the kitchen Two ground floor ensuites plus an additional twin bedroom—ideal for multi-family bookings Two junior suites upstairs, each with a private bath, supporting strong guest satisfaction and repeat stays Converted garage game room with foosball and pool tables—an amenity that significantly boosts rental performance Outdoor & Resort Amenities The screened lanai features a private heated pool, a top-performing feature for year-round bookings. Windsor Hills remains one of Central Florida’s top-performing vacation rental communities, offering: Lagoon-style resort pool Clubhouse, fitness center, and marketplace Tennis, racquetball, basketball, and volleyball Theater, arcade, playgrounds, and putting greens 24-hour guarded security Its unmatched proximity to Disney drives consistent occupancy, premium nightly rates, and strong year-round demand. Investment Highlights This property represents a rare chance to acquire a low-maintenance, high-demand, income-generating asset in one of the region’s most reliable STR markets. Windsor Hills is a purpose-built resort community offering amenities for all ages while remaining less than five minutes from Walt Disney World—making it an ideal choice for families and groups seeking affordable luxury in a prime location.

7777 Teascone Boulevard, Kissimmee

2 Beds ⋅ 2 Baths ⋅ S5155391 MLS ⋅ 3038 BLDG.

Welcome to 3038 Blossom Park, Unit 306, a bright 2-bedroom, 2-bathroom condo in a convenient Kissimmee location near Celebration and I-4. The home features new vinyl plank flooring, abundant natural light, dark matte fixtures, updated vanities and mirrors in both bathrooms and an updated kitchen with refreshed cabinetry. A laundry closet with a washer and dryer is conveniently located next to the kitchen. Both bedrooms have walk-in closets, providing generous storage space, while the functional layout offers plenty of potential for additional improvements and personal touches. The community offers a clubhouse, pool, tennis courts and sidewalks. With easy access to major roadways, shopping, dining, entertainment, and Central Florida attractions, this condo is an appealing opportunity for a primary residence, vacation getaway, or long-term investment property.

3038 Parkway Boulevard Unit 306, Kissimmee

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