Kissimmee Real Estate

Kissimmee Real Estate

Welcome to Kissimmee, Florida – a vibrant city nestled in the heart of Osceola County, where sunshine and southern charm meet! Known for its proximity to world-renowned attractions, Kissimmee is the perfect blend of adventure and relaxation.

Situated just minutes from the magical realm of Walt Disney World Resort, Kissimmee serves as an ideal base for families and thrill-seekers alike. Beyond the theme parks, the area boasts an array of outdoor activities, from scenic airboat rides on the Everglades to tranquil strolls along Lake Tohopekaliga, where you can enjoy fishing, boating, and breathtaking sunsets. Nature enthusiasts will revel in the nearby parks, such as the Shingle Creek Regional Park, which offers trails for hiking and biking, as well as opportunities for birdwatching and wildlife spotting.

Kissimmee is not just about fun and adventure; it’s also a community rich in culture and history. The historic downtown area features charming boutiques, delightful eateries, and local art galleries that showcase the talent of Florida’s artists. The vibrant community hosts numerous festivals and events throughout the year, making it easy to connect with neighbors and make lasting memories.

With a diverse range of housing options, from cozy single-family homes to luxurious waterfront properties, Kissimmee offers something for everyone. Whether you’re looking to invest in a vacation home or seeking a permanent residence, this enchanting city is ready to welcome you with open arms. Embrace the Florida lifestyle in Kissimmee, where every day feels like a vacation!

Newest Listings in Kissimmee

4 Beds ⋅ 2 Baths ⋅ Breckenridge SubDv. ⋅ 34744 Zip Code

Virtually Staged. Welcome to Breckenridge, an all-age community located just off Kings Highway in Kissimmee. This 4-bedroom, 2-bathroom fenced home offers expansive living on nearly half an acre with versatile spaces and major mechanical peace of mind. The front entryway opens directly to formal living and dining areas designed for fluid entertaining. In the heart of the home, a generous kitchen equipped with stainless steel appliances provides clear views out to the sparkling pool and overlooks the family room, complete with a cozy wood-burning fireplace and a casual dinette area. The primary retreat offers exceptional privacy, featuring a large walk-in closet and an en-suite layout with two separate vanities located in individual rooms—each featuring its own sink—alongside a soaking jacuzzi tub and separate shower. On the opposite wing, two comfortable guest bedrooms share a full bath with dual sinks, conveniently positioned near the interior laundry room. The fourth bedroom was converted from a one-car garage into a true bedroom complete with a closet and central air, while the fifth room is an air-conditioned bonus room converted into an office with private exterior access out to the spacious yard, all while still maintaining a functional two-car garage. Outdoor living shines with a 12x30 fiberglass pool and an outdoor prep sink within the fully fenced yard. The expansive parking footprint includes the two-car garage alongside a massive driveway built to accommodate 8 to 11 vehicles, offering ample space for multi-vehicle households and guest parking. Major capital improvements have all been completed, including a new roof installed in October 2024, energy-efficient replacement windows from 2021, and both the central air conditioning system and water heater replaced in April 2025. Make this your new home and schedule your private tour today!

1730 Kasey Court, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Bvl Unit 2 SubDv. ⋅ 34743 Zip Code

This wonderful single-family home is located in Osceola County at 255 Gardenia Rd, Kissimmee, FL. 255 Gardenia Rd is in the Buena Ventura Lakes neighborhood in Kissimmee, FL and in ZIP code 34743. This property has 3 bedrooms, 2 bathrooms and approximately 1,168 sqft of floor space. This property has a lot size of 8015 sqft and was built in 1979. Less Than 15 mins from the Orlando International Airport as well as 20 minutes from Disney World / Lake Buena Vista Area

255 Gardenia Road, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Big Sky SubDv. ⋅ 34744 Zip Code

Welcome to this charming move-in ready single-family home located in the desirable Big Sky community of Kissimmee. Featuring a spacious and functional floor plan with bright, light-filled living areas, a well-appointed kitchen, and comfortable bedrooms perfect for everyday living or entertaining. Enjoy low monthly HOA fees and a prime location with easy access to major roadways, local dining, shopping, and top area attractions. Schedule your private showing today and discover everything this wonderful home.

1314 Asher Mason Avenue, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Bvl Unit 3 SubDv. ⋅ 34743 Zip Code

Extensively renovated and truly move-in ready - the expensive items are already done. Brand-new roof, brand-new AC system, and a brand-new electrical panel mean no deferred maintenance waiting on the next owner. Inside, the finishes match the quality of the mechanicals: a freshly remodeled kitchen with Level 5 quartz countertops, beautifully redone bathrooms, and custom closet systems. Generous window placement fills the living areas with natural light throughout the day. The flexible floor plan includes a second kitchen, offering strong potential for a multi-generational or in-law living arrangement. The adjacent laundry area provides existing plumbing that may allow for the addition of a bathroom to further separate the space. Buyer to verify all permitted uses, zoning, and feasibility. A rare combination of updated systems and finished living space.

135 Iguala Drive, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Mill Run Unit 6 SubDv. ⋅ 34744 Zip Code

INVESTOR SPECIAL — FIX & FLIP OR LONG-TERM RENTAL OPPORTUNITY IN KISSIMMEE — NO HOA, NO RENTAL RESTRICTIONS, NON-FLOOD ZONE Calling all investors: this 3-bedroom, 2.5-bath, two-story home offers a rare combination of scale, location, and zero red tape. With no HOA and no rental restrictions, this property is equally suited to a fix-and-flip resale, a long-term rental hold, or a short-term/mid-term rental strategy for the Orlando tourism corridor. Situated in a non-flood zone, the home offers peace of mind on insurance and financing that many nearby properties can't match. The layout delivers real value: a vaulted, light-filled living room with an arched picture window, an eat-in kitchen open to the family room, a half bath downstairs, a spacious primary suite upstairs plus three additional bedrooms, a screened and covered rear patio, and a generous fenced backyard with no rear neighbors — ideal for a family rental or a value-add outdoor living upgrade. The two-car garage and long driveway offer ample parking, a plus for rental tenants or contractor access during renovation. This is a full rehab opportunity — new roof, exterior refresh, updated flooring, kitchen refresh, bathroom updates, and general finish work will unlock strong resale or rental comps in this corridor. Bring your contractor and your vision. Location is a standout for this price point. The home sits minutes from The Loop shopping and dining center, AdventHealth Kissimmee, Lakefront Park, and East Lake Toho, with quick access to major roadways including the Florida Turnpike and Highway 192 — putting Orlando's theme parks and attractions corridor within easy reach. Orlando International Airport is approximately 25 minutes away, and Lake Nona's Medical City is approximately 30 minutes away, appealing to both long-term tenants working in the medical/aviation corridors and short-term rental guests visiting the parks. The property is zoned for Mill Creek Elementary, Denn John Middle, and Gateway High, all located just a few miles from the home. Investor terms: cash offers only due to the property's condition. No blind offers and no hard money loan offers will be accepted — proof of funds required with all offers. Seller has never occupied the property and makes no representations or warranties; property is being sold strictly AS-IS, WHERE-IS, with all faults. Buyer and buyer's agent to verify all room dimensions, square footage, zoning, flood zone status, HOA/rental restriction status, and school assignments independently. Don't miss this opportunity to add a high-potential asset to your Kissimmee portfolio in one of Central Florida's most in-demand rental and resale corridors.

2651 Sherry Circle, Kissimmee

4 Beds ⋅ 2 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code

Under Construction. Kindred presents the Cali. This all concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located in the back of the home for privacy, has an en suite bathroom with a double vanity, spacious shower/tub space as well as a spacious walk-in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall you will find a fourth bedroom. This home features a space to fit all your needs. Like all homes in Kindred, the Cali includes 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.*

1868 Southbury Drive, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code

Under Construction. Inside this beautiful 4-bedroom, 3-bathroom home, you'll find 2,077 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. The kitchen features modern cabinets, quartz countertops, and sleek stainless-steel appliances. You'll never be too far from the action with the living and dining area right there. Find RevWood Select Flooring throughout a majority of the home including the family room, primary bedroom, kitchen, bathrooms, laundry and foyer. The primary bedroom has its own attached bathroom that features a walk-in closet and all the space you need to get ready in the morning. Privacy is guaranteed with a separate door for the toilet and shower. *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.*

Kissimmee

4 Beds ⋅ 3 Baths ⋅ Hilliard Rdg SubDv. ⋅ 34744 Zip Code

Welcome to this stunning modern 4-bedroom, 3-full-bathroom, two-story home offering 2,431 sq. ft. of beautifully designed living space. Thoughtfully built with numerous builder upgrades already incorporated into the floor plan, this home offers a stylish, move-in-ready feel with modern finishes and an inviting open layout. Enjoy the private, shaded lanai overlooking a peaceful backyard with no rear neighbors, creating the perfect setting for relaxing or entertaining. Conveniently located near shopping, dining, major highways, schools, and everyday amenities, this home combines comfort, privacy, and convenience. As an added bonus, the furniture is also available for sale and may be negotiable with the purchase of the home. Don’t miss the opportunity to make this beautiful modern home yours!

2647 Rania Lane, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Kindred Ph 1d SubDv. ⋅ 34744 Zip Code

Live in the beautiful town of Kindred in this perfectly maintained and upgraded ranch style home. No Carpets in the main areas, fenced in backyard and a wonderful open floor plan. The bedrooms are spacious and cozy and the yard is a great size for your furry friends or to host any events. Roof was replaced in 2024 so need to worry about any storms. Kindred offers its own fitness center, k-8 school, pool, tennis, basketball courts and plans on having its own commercial area coming soon. With this price don't delay on making an appointment to view as it wont be here for long!

1799 Partin Terrace Road, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code

Virtually Staged. Under Construction. Kindred presents the Allex. This all concrete block constructed, one-story layout optimizes living space with an open concept. As you go down the hallway and enter a spacious kitchen featuring stainless steel appliances with ample counter space and a walk-in pantry for extra storage. The living room is complete with a view to the covered lanai outside. Bedroom one, located at the back of the home for privacy, has an en suite bathroom that features a double vanity sink with a walk-in closet. Two additional guest bedrooms and one bath are tucked away down the hall from the dining room. The laundry room is located at the front of home near the two-car garage. Like all homes in Kindred, the Allex includes 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.*

2165 Serenity Garden Drive, Kissimmee

3 Beds ⋅ 2 Baths ⋅ North Point SubDv. ⋅ 34744 Zip Code

Virtually Staged. Pond views through the trees, a screened paver patio, and mature fruit trees make the backyard a highlight of this three-bedroom, two-bath home in gated North Point. Inside, 1,941 square feet unfold across a single-story layout with separate front gathering rooms, an open kitchen and rear living area, and a primary suite with its own patio access. Fresh interior paint and recently updated major systems complement the home's architectural detail. A paver driveway and recessed entry lead to arched openings, decorative columns, and tray ceilings that give the front rooms definition without closing them off. The family room sits beside the foyer, with a bay-style arrangement of windows overlooking the front lawn. An adjoining dining room offers space for a full dining table, while ceramic tile carries through the main living areas. The kitchen brings color and character to the center of the home with blue cabinetry, stone counters, and pendant lighting. An island with raised breakfast-bar seating provides a place to gather while meals take shape, with additional cabinetry below. Open to the kitchen, the rear living room looks out toward the backyard, with sliding doors extending the gathering space onto the screened patio. At the rear of the home, the primary suite pairs a tray ceiling and hard-surface vinyl flooring with a walk-in closet and direct access outdoors. The en suite bath offers dual sinks, stone counters, a soaking tub, a separate shower, and an enclosed toilet area. Two additional bedrooms have built-in closets and share a bathroom with a separate vanity area and walk-in shower. A dedicated interior laundry room adds cabinetry, shelving, and a utility sink near the attached two-car garage. Out back, the screened patio has paver flooring, ceiling fans, and space for dining and lounging. A curved paver sitting area extends beyond the enclosure into the fully fenced lawn, where mature mango, lemon, and olive trees add another layer to the landscape. Trees along the rear outlook frame views toward the pond, giving the outdoor spaces an appealing sense of separation. The A/C system and water heater are both less than three years old, and the roof year is reported as 2013. An epoxy-coated garage floor completes the practical updates. North Point residents enjoy a community pool, with Boggy Creek Road and SR 417 providing connections to Lake Nona and the wider Orlando area. Some images have been virtually staged.

4419 Azure Isle Way, Kissimmee

4 Beds ⋅ 2 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code

Under Construction. The Harper floorplan offers a 4-bedroom, 2-bathroom home with 1,665 sq ft of living space. Features include quartz and Revwood floors, an open layout, a spacious living room with natural light, a chef's kitchen with quartz countertops and stainless steel appliances, and a primary suite with a private ensuite bathroom. This all concrete block construction home also includes smart home technology for control via smart devices. *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.*

2159 Serenity Garden Drive, Kissimmee

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