Kissimmee Homes under $250,000

Kissimmee Homes under $250,000

Welcome to Kissimmee, Florida—an enchanting city nestled in the heart of Osceola County, just minutes away from the world-renowned attractions of Orlando. Known for its vibrant community and diverse culture, Kissimmee offers a unique blend of small-town charm and modern convenience. With its picturesque landscapes, beautiful parks, and a lively downtown area, Kissimmee is an ideal place for families, retirees, and anyone looking to embrace the Florida lifestyle.

One of the most appealing aspects of Kissimmee is the affordability of its housing market. For those seeking homes under $250,000, this city presents a plethora of options that cater to various tastes and preferences. From cozy single-family homes to charming townhouses, you'll find properties that offer both comfort and value. Many of these homes are situated in friendly neighborhoods, complete with amenities such as community pools, playgrounds, and walking trails that encourage an active and social lifestyle.

Living in Kissimmee means enjoying the best of both worlds—easy access to thrilling attractions like Walt Disney World and Universal Studios, while also relishing the tranquility of suburban living. The city boasts excellent schools, shopping centers, and dining options, ensuring that residents have everything they need right at their fingertips.

Whether you’re a first-time homebuyer or looking to invest, Kissimmee’s affordable housing market under $250,000 is a fantastic opportunity. Discover the charm of this vibrant city and find your dream home today!

Newest Kissimmee Homes under $250,000

1106 Spring Meadow Drive, Kissimmee
$189,900
2 Beds ⋅ 2 Baths ⋅ S5158857 MLS ⋅ 1106 BLDG.
A fresh start begins here! This beautifully updated 2-bedroom, 1.5-bath townhome in Kissimmee combines a NEW KITCHEN, NEW HVAC, and a ONE-CAR GARAGE with the added appeal of LOW HOA FEES and a COMMUNITY POOL. The new kitchen takes center stage, offering a refreshed space to prepare meals and enjoy everyday living, while the new HVAC system provides year-round comfort. A private garage adds convenient parking and storage, and the community pool offers a refreshing escape on sunny Florida days. With desirable updates already in place, 1106 Spring Meadow Drive deserves a spot on your must-see list. Bring your offer and make it yours—schedule your private showing today!

1106 Spring Meadow Drive, Kissimmee
2202 Key West Court Unit 633, Kissimmee
$174,900
2 Beds ⋅ 2 Baths ⋅ O6447069 MLS ⋅ Buld. #6 BLDG.
One or more photos are virtually staged for décor inspiration only; no structural changes are shown. INVESTOR OPPORTUNITY! This spacious 2-bedroom, 2-bath condo in Villas del Sol combines what investors value most: location, rental flexibility, and strong guest appeal. Daily vacation rentals are permitted, offering the flexibility to operate as a short-term rental, consider longer-term occupancy, or enjoy personal use. Ideally positioned in Kissimmee near Walt Disney World, The Loop, shopping, dining, entertainment, and major Central Florida roadways, the community also offers resort-style amenities including pools, fitness center, tennis courts, playground, and recreational areas. An opportunity to own a property designed around the lifestyle and convenience vacation guests seek. Own near the attractions—and turn location into opportunity. Buyer to independently verify current HOA rules, short-term rental eligibility, licensing, and restrictions.

2202 Key West Court Unit 633, Kissimmee
9055 Treasure Trove Lane Unit 204, Kissimmee
$249,000
3 Beds ⋅ 2 Baths ⋅ A12099831 MLS
Enjoy the best of Central Florida living just a short drive from Walt Disney World® Resort! Welcome to Caribe Cove! This spacious 3-bedroom, 2-bathroom condo offers a flexible opportunity for those seeking a Central Florida getaway or short-term rental property.The open-concept layout provides plenty of space to relax and entertain, with a well-appointed kitchen overlooking the dining and living areas. A desirable split-bedroom floor plan offers added privacy, while generously sized bedrooms and bathrooms provide comfortable accommodations.One of the highlights of this unit is the beautiful lagoon view. Step outside to the screened balcony and enjoy the peaceful scenery—an inviting setting for morning coffee or unwinding after a day exploring Central Florida.Caribe Cove offers resort-style amenities and convenient access to Highway 192, theme parks, shopping, dining, entertainment, and the many attractions of the Kissimmee/Orlando area.

9055 Treasure Trove Lane Unit 204, Kissimmee
261 Autumn Lane Unit 5, Kissimmee
$240,000
3 Beds ⋅ 3 Baths ⋅ O6446302 MLS ⋅ Autumn Lane BLDG.
SPACIOUS 3-BEDROOM, 3-FULL-BATH CONDO WITH ASSIGNED PARKING IN KISSIMMEE! Welcome to 261 Autumn Lane #5, offering 1,504 square feet of living space, three bedrooms, three full bathrooms, two private en-suite bedrooms, assigned parking, and major recent improvements including a 2025 ROOF and updated A/C from 2022. Built in 2007, this two-story condo offers a flexible layout with something buyers don't find in every 3-bedroom property: two bedrooms feature their own private full bathrooms. The additional privacy creates excellent flexibility for guests, multi-generational living, a home office setup, or households looking for more separation and personal space. Two major updates are already in place, including a NEW ROOF completed in 2025 and an updated A/C system from 2022, giving buyers added confidence when considering some of the home's major components. LOCATION is another major advantage. Situated in the Buenaventura Lakes area of Kissimmee, this Central Florida condo offers convenient access to Orlando International Airport, shopping, grocery stores, restaurants, everyday services, and major roadways connecting Kissimmee and the greater Orlando area. Nearby shopping and grocery options include ALDI, Walmart Neighborhood Market, and additional retail and dining options throughout the Osceola Parkway and Buenaventura Lakes area. If you've been searching for a 3-bedroom condo in Kissimmee with THREE FULL BATHROOMS, multiple en-suite bedrooms, assigned parking, generous living space, recent major updates, and convenient access to Orlando, 261 Autumn Lane #5 deserves a closer look. Schedule your private showing today.

261 Autumn Lane Unit 5, Kissimmee
4994 Town Terrace N, Kissimmee
$240,000
3 Beds ⋅ 3 Baths ⋅ O6446576 MLS ⋅ 4994 BLDG.
Virtually Staged. Start your mornings with coffee overlooking the pond and end your days relaxing on your screened rear lanai. This three bedroom, three full-bathroom townhome in Trafalgar Village offers over 1,500 square feet of living space within a community featuring 24-hour guard gated access. Updated kitchen countertops, fresh interior paint, and fresh carpeting create a welcoming backdrop for your next chapter, whether you’re settling into a primary residence or creating a Florida getaway. Spend an afternoon by the community pool and spa, catch a movie at the clubhouse theater, or enjoy a game of pickleball, basketball, beach volleyball, or shuffleboard. A fitness center and game room with billiards and video games provide even more ways to unwind. Outdoors, discover a sandy beach area, scenic walking and jogging paths, a dog park, playground, and barbecue and picnic areas, all complemented by beautifully maintained common grounds and private community mailboxes. Low maintenance living adds to the appeal, with HOA coverage that includes lawn care, landscaping, trash service, roof, and exterior painting. Located in Kissimmee, Trafalgar Village offers access to shopping, dining, entertainment, and Central Florida’s celebrated theme parks, including Walt Disney World. With both short-term and long-term rentals permitted, this townhome offers the flexibility to enjoy it as your own home, a vacation retreat, or an investment property. Schedule your private showing and discover the possibilities.

4994 Town Terrace N, Kissimmee
8810 Grand Palms Circle Unit B, Kissimmee
$199,000
3 Beds ⋅ 2 Baths ⋅ O6446760 MLS ⋅ 8810 BLDG.
Location is the headline here. This second-floor 3-bedroom, 2-bath condo sits inside the Grand Palms community, less than 20 minutes from Walt Disney World Resort and Universal Orlando Resort, with Sunset Walk, Island H2O, US-192 and I-4 all nearby. And when you’re not chasing theme parks? The community pool, tennis and pickleball courts are literally just steps from your door, with a screened balcony overlooking the action. Inside, vaulted ceilings open up the main living space, while a split-bedroom layout and in-unit laundry make three bedrooms easy to actually use. Keep it as your own Florida getaway. Escape the winter. Give your Disney College Program student a home base. Or take advantage of short-term rental zoning and put it to work when you’re not here. The HOA even handles exterior maintenance, including the roof. Three bedrooms. Second floor. Pool views. Minutes from Disney. Short-term rentals allowed. There are a lot of ways to make this one make sense.

8810 Grand Palms Circle Unit B, Kissimmee
1604 Columbia Arms Circle Unit 216, Kissimmee
$226,000
3 Beds ⋅ 2 Baths ⋅ S5158735 MLS ⋅ 1604 BLDG.
Enjoy peaceful lake views from this spacious 3-bedroom, 2-bathroom condo located on the second floor of a gated community. The unit features brand-new carpet throughout all living areas, creating a fresh and inviting atmosphere. The kitchen comes fully equipped with a refrigerator, range, range hood, dishwasher, garbage disposal, washer, and dryer, offering convenience and functionality from day one. In addition, this unit is privileged with an independent storage garage, perfect for extra storage or for generating additional income for the owner through rental. The community offers exceptional amenities, including a swimming pool, fitness center, playground, pickleball courts, basketball court, and an in-ground spa—ideal for those seeking an active and balanced lifestyle. Its location is unbeatable, close to schools, shopping centers, restaurants, gyms, daycares, pharmacies, hospitals, banks, and major commercial areas. There is an administrative fee payable to the association that the new owner must pay ($750). The HOA fee includes sewer, trash, and pest control. The unit is currently occupied with a tenant. Owner is motivated.

1604 Columbia Arms Circle Unit 216, Kissimmee
9055 Treasure Trove Lane Unit 204, Kissimmee
$249,000
3 Beds ⋅ 2 Baths ⋅ O6446389 MLS ⋅ Ph 4 BLDG.
Enjoy the best of Central Florida living just a short drive from Walt Disney World® Resort! Welcome to Caribe Cove, This spacious 3-bedroom, 2-bathroom condo offers a flexible opportunity for those looking for a Florida getaway, primary residence, or short-term rental property. The open-concept layout provides plenty of space to relax and entertain, with a well-appointed kitchen overlooking the dining and living areas. The desirable split-bedroom floor plan offers added privacy, while generously sized bedrooms and bathrooms provide comfortable accommodations. One of the highlights of this unit is its beautiful lagoon view. Step outside to the screened balcony and enjoy the peaceful scenery—an inviting setting for morning coffee or simply relaxing after a day enjoying Central Florida. Caribe Cove offers resort-style living with convenient access to Highway 192, theme parks, shopping, dining, entertainment, and the many attractions of the Kissimmee/Orlando area. The community currently allows short-term rentals, offering additional flexibility for owners. Buyers should independently verify current rental restrictions, requirements, and applicable regulations.

9055 Treasure Trove Lane Unit 204, Kissimmee
2806 Osprey Cove Place Unit 201, Kissimmee
$199,900
3 Beds ⋅ 2 Baths ⋅ O6446458 MLS
Take a look at this beautiful 3 bed, 2 bath, 2nd floor condo with spectacular panoramic views of Osprey Cove at the Oaks golf course. END UNIT in a desirable, GATED, GOLF community! NO REAR NEIGHBORS. Lovely, SPLIT FLOOR PLAN with a lot of natural lighting throughout the unit. LVP flooring throughout! Walk in closet in primary bedroom. Private stairs, assigned parking near building. Community pool & tennis courts. Location is convenient to shopping, dining, theme parks & more! Schedule your showing today and see what this home has to offer!

2806 Osprey Cove Place Unit 201, Kissimmee
2203 Key West Court Unit 422, Kissimmee
$199,000
2 Beds ⋅ 2 Baths ⋅ A4708120 MLS ⋅ 2292 BLDG.
Welcome to your perfect Florida getaway or permanent paradise at Villas Del Sol at Kissimmee. Nestled in the heart of Kissimmee, this stunning two-bedroom, two-bathroom condo offers the ultimate blend of modern comfort and vacation style living, just minutes from Orlando’s world famous theme parks, premier dining and entertainment. The fully equipped kitchen features contemporary finishes and flows seamlessly into the dining and living area. The thoughtful split-floorplan design ensures maximum privacy for both bedrooms. The spacious primary suite is a private retreat, complete with an en-suite bathroom and water view of the pool. The second bedroom is equally inviting and offers direct private access to a full bathroom, creating a functional and flexible layout ideal for guests, roommates, or multi-generational living. NOTE: SOLD FULLY FURNISHED A standout feature of this property is the assigned private closed garage located within the same building, providing exceptional convenience, security, and valuable extra storage—an uncommon and highly desirable benefit. Beyond the front door, the community offers a premier resort lifestyle. Spend your sunny afternoons lounging by one of the two sparkling, resort-style swimming pools, or stay active and healthy in the state-of-the-art fitness center without ever leaving the property! This sought after community also has a tennis court, walking sidewalks, playground and a designated grilling area! Whether you are looking for a lucrative short-term rental investment, a vibrant second home, or a low-maintenance primary residence, this condo delivers the quintessential sunshine state experience! Ideally located just minutes from The Loop, with access to a wide variety of shopping, dining, entertainment, and major retail stores including Publix, Walmart Supercenter, and ALDI. Conveniently located near local schools such as Flora Ridge Elementary School, Kissimmee Middle School, and Osceola High School. Easy access to major roadways including Osceola Parkway, US-192, and Florida’s Turnpike allows seamless connectivity to Orlando, Walt Disney World Resort, and Orlando International Airport. The community offers flexible rental opportunities, including both short-term and long-term leasing options. An excellent opportunity for a primary residence, second home, or investment property in Central Florida.

2203 Key West Court Unit 422, Kissimmee
3002 Rio Grande Trail Unit 3002, Kissimmee
$215,000
3 Beds ⋅ 2 Baths ⋅ O6446397 MLS ⋅ 3002 BLDG.
Prime Kissimmee Investment Opportunity – Dual Rental Flexibility! Discover the ultimate real estate asset at 3002 Rio Grande Trail #3002 in the highly desirable Shadow Bay Villas community. This spacious 1,250 sq. ft. condo features an open-concept layout where the kitchen flows seamlessly into the main living and dining spaces—perfect for entertaining. Massive windows fill the home with abundant natural light, highlighting low-maintenance ceramic tile flooring throughout. This residence allows for both short-term vacation rentals and long-term leasing, giving you complete freedom to maximize your rental income strategy. Community pools is right down the street from this unit. Location is everything, and this property puts your guests minutes away from Central Florida’s world-famous theme parks, premier dining, and shopping centers like The Loop. Schedule a priave showing today and make this condo your new residence.

3002 Rio Grande Trail Unit 3002, Kissimmee
3025 Greystone Loop Unit 302, Kissimmee
$215,000
3 Beds ⋅ 2 Baths ⋅ O6446083 MLS ⋅ 3025 BLDG.
"Open the Door to Your Dreams" of Owning A very spacious Condo in a very secure gated community. The home features: 5 New ceiling fans; New carpet throughout the home; The spacious kitchen has lots of cabinets and pantry space. This Condo features 3 large bedroom; And oversized Living Room for large family gatherings; and it has French Doors that leads to an oversized Balcony with a great view. The primary bedroom has a separate room (which can be a library/office or exercise room. Come see it today. At this low price it will not last long.

3025 Greystone Loop Unit 302, Kissimmee
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