Kissimmee Real Estate

Kissimmee Real Estate

Welcome to Kissimmee, a vibrant city located in Osceola County, Florida. Known for its beautiful landscapes, warm weather, and close proximity to world-famous attractions, Kissimmee is a fantastic place to call home.

Situated in the heart of Central Florida, Kissimmee offers residents a diverse range of amenities and activities. Nature enthusiasts will love exploring the nearby Everglades and Kissimmee Chain of Lakes, where they can enjoy boating, fishing, and wildlife spotting. For those seeking adventure, the city is just a short drive away from the thrilling theme parks of Orlando, including Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando.

Kissimmee boasts a rich cultural heritage, with a variety of museums, art galleries, and historic sites to explore. The city's downtown area is a hub of entertainment, with vibrant restaurants, shops, and live music venues. Additionally, Kissimmee hosts numerous festivals and events throughout the year, showcasing the local talent and community spirit.

Real estate in Kissimmee offers a wide range of options to suit every lifestyle and budget. From charming single-family homes in quiet neighborhoods to luxurious waterfront properties, there is something for everyone. The city's real estate market is known for its affordability, making it an attractive destination for both first-time homebuyers and investors.

With its ideal location, abundant amenities, and strong sense of community, Kissimmee is truly a place where you can live, work, and play. Whether you're looking to settle down or invest in real estate, Kissimmee offers endless opportunities and a high quality of life.

Newest Listings in Kissimmee

$330,000
3 Beds ⋅ 2 Baths ⋅ Emerald Pointe SubDv. ⋅ 34743 Zip Code
Welcome to this 3-bedroom, 2-bathroom home in the desirable Lakeside community of Kissimmee, featuring an additional versatile room that offers the flexibility to be used as a home office, guest room, playroom, or potential 4th bedroom depending on your needs. The comfortable and functional layout offers plenty of natural light throughout the living areas, along with a 2-car garage for added storage and convenience. Recent updates include a roof replaced in 2018 and windows updated in 2020, providing added peace of mind for the next owner. The backyard overlooks a tranquil conservation area, offering privacy and a peaceful setting to relax or entertain. Conveniently located near The Loop for shopping and dining, grocery stores, medical facilities, Osceola Parkway, and the Florida Turnpike, with easy access to Orlando International Airport, Lake Nona, and Central Florida’s top attractions. A great opportunity for a primary residence or investment property in an established Kissimmee neighborhood. Schedule your private showing today!

2344 Topaz Trail, Kissimmee
$499,900
5 Beds ⋅ 3 Baths ⋅ North Shore Village SubDv. ⋅ 34744 Zip Code
Virtually Staged. Welcome to this spacious two-story home offering 3,385 heated square feet of thoughtfully designed living space on an 8,102-square-foot fenced lot. Built in 2007, this 5-bedroom, 3-bathroom residence features a functional floor plan with a formal living room, dining room, well-appointed kitchen, family room, attached two-car garage, and a first-floor bedroom and full bathroom—ideal for guests or multigenerational living. Upstairs, you'll find a versatile bonus room/foyer, four additional bedrooms including the expansive primary suite, as well as a conveniently located laundry room. The fenced backyard provides added privacy and space to relax, entertain, or enjoy outdoor activities. Offering generous living areas and a layout designed for comfort and flexibility, this home is ready for its next owner. Schedule your private showing today and discover all it has to offer!

3915 Shoreview Drive, Kissimmee
$1,549,000
5 Beds ⋅ 4 Baths ⋅ Florida Fruit Belt Sls Co SubDv. ⋅ 34744 Zip Code
Experience elevated country living in this rare, custom-built estate compound set on 5.23 fully cleared and fenced acres in the heart of Kissimmee. Designed for both privacy and functionality, the property features two separate concrete driveways with electronic gated entry for seamless access. The main residence offers 5 bedrooms, 3.5 bathrooms, and a 3-car garage, with a thoughtfully designed split, open-concept floor plan. Light-filled living spaces include formal living and dining areas, a spacious family room, and a striking Chicago brick wood-burning fireplace that anchors the home with warmth and character. A large bonus room and screened living area provide flexible space for entertaining and everyday comfort. Outdoors, enjoy a true resort-style experience with a stunning pool and waterfall feature, complemented by a dedicated pool bath for guests. Expansive front and rear views showcase the beauty and scale of the property. For car enthusiasts, hobbyists, or business use, the nearly 4,000 sq ft steel-constructed outbuilding is equipped with upgraded electrical and a car lift, offering exceptional versatility. An additional bonus/play space above the garage adds even more room for recreation or creative use. A unique blend of space, style, and capability—this is a one-of-a-kind opportunity ready for immediate enjoyment.

2745 Lloyd Lane, Kissimmee
$395,995
3 Beds ⋅ 2 Baths ⋅ Bvl Unit 9 6th Add SubDv. ⋅ 34743 Zip Code
POOL HOME + PAID-OFF SOLAR + NO HOA! Your Florida lifestyle starts here! This spacious 3-bedroom, 2-bath home with a two-car garage features an open floor plan, split-bedroom layout, vaulted ceilings, and beautiful tile flooring. The updated kitchen shines with quartz countertops, 42-inch shaker cabinets, stainless steel appliances, and a breakfast bar perfect for entertaining. Unwind in the spacious primary suite featuring a large walk-in closet and an upgraded bathroom with a beautifully tiled walk-in shower. The backyard is where the vibes come alive! Fire up the grill, gather with family and friends on the spacious patio deck, then cool off in your private in-ground pool. The oversized, fully fenced lot provides plenty of privacy and room to enjoy. Best of all, the solar panels are fully paid off—no solar loan or lease payment! Conveniently located near Florida’s Turnpike, Medical City, major hospitals, shopping, dining, Orlando International Airport, and Central Florida attractions. Don’t miss this opportunity—schedule your private showing today!

247 Competition Drive, Kissimmee
$549,900
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 rated to withstand 140mph winds 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
$339,000
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
$465,000
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
$384,900
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
$275,000
3 Beds ⋅ 3 Baths ⋅ Mill Run Unit 6 SubDv. ⋅ 34744 Zip Code
**MULTIPLE OFFERS RECEIVED. PLEASE SUBMIT HIGHEST AND BEST BY END OF DAY ON SUNDAY, SEPTEMBER 13TH** 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
$463,490
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
$505,050
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
$530,000
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
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