Kissimmee Homes under $250,000

Kissimmee Homes under $250,000

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the enchantment of Central Florida with the warmth of Southern hospitality. Nestled just a stone's throw from the world-renowned attractions of Orlando, Kissimmee offers a unique lifestyle that is both exhilarating and serene. With its picturesque lakes, lush parks, and a rich tapestry of cultural experiences, this charming city is an ideal place to call home.

For those seeking affordable housing options, Kissimmee is a treasure trove of homes under $250,000. Here, you can find a variety of charming single-family homes, cozy townhouses, and well-maintained condos that cater to diverse lifestyles and budgets. Whether you're a first-time homebuyer, a growing family, or looking for a peaceful retirement retreat, Kissimmee has something to suit your needs.

Imagine waking up to the gentle Florida sun, enjoying your morning coffee on a spacious porch, or taking a leisurely stroll through one of the many scenic parks. The community spirit in Kissimmee is palpable, with friendly neighbors and a plethora of local events that bring residents together. Plus, with easy access to major highways, commuting to nearby cities or attractions is a breeze.

Kissimmee is not just a place to live; it's a place to thrive. With an array of dining, shopping, and entertainment options, you’ll never run out of things to do. Explore the historic downtown area, indulge in delicious cuisine, or enjoy a day at the nearby theme parks. Discover the joy of living in Kissimmee, where every day feels like a vacation!

Newest Kissimmee Homes under $250,000

8805 Dunes Court Unit 5-103, Kissimmee
$185,000
1 Beds ⋅ 1 Baths ⋅ Legacy Dunes Condo SubDv. ⋅ 34747 Zip Code
Less than 6 miles from Walt Disney World, your Central Florida getaway or next investment opportunity awaits! Welcome to 8805 Dunes Court, Unit 103, in Legacy Dunes, a gated condominium community in Kissimmee offering an appealing combination of location, convenience and short-term rental flexibility. Whether you're searching for a vacation home near Disney, a second home or an income-producing investment opportunity, this first-floor turnkey condo offers a well appointed and comfortable living space, stainless steel kitchen appliances and a screened front porch perfect for morning coffee or relaxing after a day of exploring. With no stairs to navigate, the ground-floor location adds everyday convenience. One of the property's biggest advantages is the ability to accommodate short-term rentals, providing flexibility for personal use, vacation rentals or both. Legacy Dunes offers a swimming pool, tennis courts, clubhouse, playground, and convenient parking. The monthly condo fee includes internet, water, sewer, trash, exterior and grounds maintenance, pest control, pool maintenance, recreational facilities that include a resort style pool, clubhouse with a game room featuring air hockey, ping pong and a pool table, on site Cafe & Bar, tennis courts, basketball courts, volleyball courts and a playground area. All of this with easy access to Disney, Universal, shopping and area beaches! Location, rental flexibility and low-maintenance ownership come together in one exciting opportunity. Discover the possibilities of owning a ready to go vacation-friendly condo in the Disney area!

8805 Dunes Court Unit 5-103, Kissimmee
2204 Key West Court Unit 511, Kissimmee
$164,000
1 Beds ⋅ 1 Baths ⋅ Villas Del Sol At Kissimmee Condo SubDv. ⋅ 34741 Zip Code
Virtually Staged. ATTENTION INVESTORS! DAILY, SHORT and LONG -TERM RENTALS allowed/ AIRBNB POTENTIAL! LOW HOA FEES! Welcome to VILLA DEL SOL in Kissimmee 34741! This charming CONER GROUND-FLOOR, 1-bedroom, 1-bathroom condo is ideal for vacation rentals or long-term investment. Features include ceramic tile flooring, laminate flooring in the bedroom, a spacious walk-in closet, Whirlpool stainless steel kitchen appliances, a bathroom with dual access, and a laundry room with a full-size washer and dryer. CURRENTLY RENTED TO A GOOD TENANT ON A MONTH-TO-MONTH LEASE! Enjoy RESORT-STYLE AMENITIES in this gated community, including a clubhouse, fitness center, 2 swimming pools, spas, tennis courts, playground, and scenic pond views. Building just painted! DAILY, SHORT and LONG -TERM RENTALS allowed. Great opportunity for investors or future owner-occupants! Schedule your showing today!

2204 Key West Court Unit 511, Kissimmee
4021 Venetian Bay Drive Unit 103, Kissimmee
$195,000
3 Beds ⋅ 2 Baths ⋅ Venetian Bay Village Condo Ph 1 SubDv. ⋅ 34741 Zip Code
INVESTOR ALERT! INCOME-PRODUCING PROPERTY! Excellent investment opportunity in the desirable Venetian Bay Villages resort-style community in Kissimmee! This 3-bedroom, 2-bath condo is ALREADY RENTED FOR $1,800 MONTHLY, GENERATING $21,600 IN ANNUAL GROSS RENTAL INCOME! Major improvements include REPLACED HVAC SYSTEM, WATER HEATER, AND ELECTRICAL PANELS, offering added value and peace of mind! Enjoy outstanding rental flexibility, from short-term stays with a 7-day minimum to annual leases, subject to association requirements. This 24-hour guard-gated community features multiple swimming pools, a clubhouse, fitness center, tennis and basketball courts, and playgrounds. PRIME LOCATION NEAR ALL MAJOR CENTRAL FLORIDA THEME PARKS, INCLUDING WALT DISNEY WORLD, UNIVERSAL ORLANDO, AND SEAWORLD! Just minutes from The Loop shopping center, restaurants, entertainment, and major highways. IMMEDIATE RENTAL INCOME, MAJOR UPGRADES, AND EXCELLENT INVESTMENT POTENTIAL! Don't miss this opportunity!

4021 Venetian Bay Drive Unit 103, Kissimmee
5367 W Irlo Bronson Memorial Highway Unit 1-214, Kissimmee
$77,500
1 Beds ⋅ 1 Baths ⋅ Greenpoint Essential Hotel Condo SubDv. ⋅ 34746 Zip Code
Keep More of Every Booking: Cashflow-Ready Condo-Hotel with NO DEVELOPER ADMINISTRATION FEE! This is the one that stands apart. While every other available unit in the development pays a developer administration fee, this first-floor condo-hotel unit pays none, meaning more of every night’s booking goes straight to your bottom line. The location sells itself. Right on W Irlo Bronson Memorial Hwy (192) in Kissimmee, you’re just minutes from Disney, the World Food Trucks park, Orlando International Airport, and the endless attractions that draw millions of visitors to Central Florida every year. That steady stream of travelers is exactly who you want booking your unit. Ownership here is refreshingly easy. The friendly on-site front desk greets your guests and handles check-in and keys, delivering a true hotel experience while you stay completely hands-off. The unit arrives fully furnished and guest-ready: comfortable double beds, TV, in-room safe, and mini fridge. Plus, the low HOA covers electricity, water, internet, and cable, so your monthly costs stay lean, predictable, and stress-free. No admin fee, no hassle, no waiting. Just a turnkey unit built to generate cashflow from day one. Opportunities like this don’t last. Cash only sale.

5367 W Irlo Bronson Memorial Highway Unit 1-214, Kissimmee
3117 Sandy Shore Ln, Kissimmee
$230,000
3 Beds ⋅ 2 Baths ⋅ Raintree Park SubDv. ⋅ 34743 Zip Code
Virtually Staged. Welcome to this inviting 3-bedroom, 2-bathroom home in the Raintree Park community of Kissimmee! Featuring high ceilings that create a spacious, airy feel, this home offers a functional layout with one bedroom conveniently located on the first floor. Enjoy the added benefit of no carpet throughout, providing a clean and low-maintenance living environment. Ideally located near shopping, dining, parks, and everyday conveniences, with easy access to major roadways for commuting throughout Kissimmee and the greater Orlando area. Whether you're looking for comfort, convenience, or a versatile floor plan, this home is a wonderful opportunity to make your own!

3117 Sandy Shore Ln, Kissimmee
3000 Laurel Park Lane Unit 107, Kissimmee
$238,500
3 Beds ⋅ 2 Baths ⋅ Flora Ridge Condo Ph 5 Bldg 2 SubDv. ⋅ 34741 Zip Code
Excellent opportunity for homeowners and investors! This first-floor condo in Kissimmee is being sold AS-IS and features 3 bedrooms, 2 bathrooms, and a versatile den that can be used as an additional bedroom, home office, or flex space. Conveniently located near major shopping centers, restaurants, and entertainment, and just minutes from Walt Disney World Resort, this property offers an ideal combination of location, comfort, and convenience. Situated within a secure, gated community, residents can enjoy peace of mind and resort-style amenities, including a beautiful swimming pool overlooking the lake—perfect for relaxing and unwinding. The community also offers elevator access to all floors. Enjoy the convenience of first-floor living with easy access to the community amenities. Whether you are looking for a primary residence, vacation home, or investment opportunity, this property offers excellent potential in a desirable Kissimmee location.

3000 Laurel Park Lane Unit 107, Kissimmee
2856 Osprey Cove Place Unit 204, Kissimmee
$234,997
3 Beds ⋅ 2 Baths ⋅ Osprey Cove At The Oaks Condo Ph 15 SubDv. ⋅ 34746 Zip Code
Welcome home to 2856 Osprey Cove Pl #204, a beautifully updated 3-bedroom, 2-bathroom second-floor CORNER condo in the gated golf course community of Osprey Cove at The Oaks in Kissimmee, FL. As a corner unit, this home offers extra privacy, more natural light, and fewer shared walls. Inside, high ceilings and an open floor plan create a bright, airy space where the kitchen, dining, and living areas flow together for easy everyday living and entertaining. The split floor plan places the primary suite and the second bedroom on opposite sides of the home, making it a great fit for guests, a roommate, or a home office. Step out to your screened-in patio for morning coffee or a relaxing evening outdoors without the bugs. Life at Osprey Cove means a gated entry, a sparkling community pool, and a peaceful golf course setting within The Oaks, home to Oaks National Golf Club. Lake Tohopekaliga (Lake Toho), one of Florida’s top bass fishing lakes, is just minutes away for boating, fishing, and airboat tours. The location is hard to beat. Shoppes of Kissimmee on John Young Pkwy is less than a mile away, and Publix at Pleasant Hill Commons and the Village Shops at Bellalago are a quick drive. Enjoy nearby dining like Mama Romano’s, Pazza Luna, Aji Ceviche Bar, and Boba Casa, plus local coffee and bakery spots throughout the Pleasant Hill and Osceola Pkwy corridors. Outdoor lovers can bike or walk the Shingle Creek Regional Trail, kayak the headwaters of the Everglades at Shingle Creek Regional Park, or catch the sunset at Kissimmee Lakefront Park. Historic Downtown Kissimmee, Old Town, Gatorland, and Walt Disney World are all a short drive. Commuting is easy with quick access to John Young Pkwy, US-192, Osceola Pkwy, and Florida’s Turnpike, plus the Kissimmee SunRail/Amtrak station. Osceola Regional Medical Center, Valencia College Osceola Campus, and Orlando International Airport are all within easy reach. Zoned for Pleasant Hill Elementary, Horizon Middle, and Liberty High (buyer to verify). Whether you’re looking for a low-maintenance primary residence, a second home near the parks, or an investment property in a high-demand rental area, this updated corner condo checks every box. Schedule your private showing today!

2856 Osprey Cove Place Unit 204, Kissimmee
1777 Atwater Court, Kissimmee
$249,900
4 Beds ⋅ 2 Baths ⋅ Windmill Point Unit 4b SubDv. ⋅ 34746 Zip Code
Wow!! Freshly to this HOT market, Investor opportunity, or 1st time home buyer. A Unique opportunity to work onto your next project that can be added to your Investment portfolio. Whether you are looking for your next fixer-upper project or make it your own primary residence, this home has significant potential. Do not miss out this great opportunity to own this 4-BEDROOM 2 BATH,1,855 square living space that offers a Dining and living room combo and a large kitchen. Property also offers a large/spacious backyard with plenty of potential to host gatherings with family and friends. This home is the perfect opportunity for a FIXER-UPPER that can generate income. Property is sold AS IS ONLY. Don't miss out on this fantastic opportunity!

1777 Atwater Court, Kissimmee
2210 Grand Cayman Court Unit 1733, Kissimmee
$180,000
2 Beds ⋅ 2 Baths ⋅ Villas Del Sol At Kissimmee Condo SubDv. ⋅ 34741 Zip Code
Virtually Staged. Welcome to Villa Del Sol! Whether you're looking for a place to call home, a Florida getaway, or an investment opportunity, this 2-bedroom, 2-bathroom condo offers flexibility, comfort, and a convenient location. With 1,026 square feet of living space, the unit features laminate flooring throughout the main living areas, carpeted bedrooms, and a kitchen with shaker-style cabinets, granite countertops, and plenty of storage. One of the biggest advantages of this property is its rental flexibility, allowing both short-term and long-term rentals. Enjoy it as your primary residence, use it as a vacation retreat, or take advantage of its income-producing potential. Villa Del Sol offers community amenities including swimming pools, tennis courts, a playground, and outdoor spaces to enjoy the Florida sunshine. The location is another highlight, with The Loop shopping and dining destination nearby, along with convenient access to Disney theme parks, other Central Florida attractions, restaurants, and major roadways. Whether you're buying for yourself or adding to your investment portfolio, this condo offers a great combination of location, lifestyle, and opportunity. Schedule your private showing today!

2210 Grand Cayman Court Unit 1733, Kissimmee
3008 Red Ginger Road, Kissimmee
$219,000
2 Beds ⋅ 3 Baths ⋅ Encantada Ph 2 SubDv. ⋅ 34747 Zip Code
This INCREDIBLY priced turnkey 2-bedroom, 2.5-bathroom townhome in the HIGHLY desirable Encantada Resort arrives fully furnished and offers total flexibility as a proven short-term rental, private vacation getaway, or permanent primary residence. The main level features a fluid open floor plan with tile flooring throughout the kitchen, dining, and living spaces, alongside a practical laundry room, utility closet and half bath. The rear sliding doors open directly to a semi-private back patio with your own private jacuzzi, providing an ideal retreat after a day of entertainment! Upstairs, the layout ensures privacy with a spacious primary suite and master bathroom along side a second bedroom featuring its own dedicated en-suite bathroom as well. Encantada Resort elevates the ownership experience with premium community amenities, including gated security, a vibrant clubhouse, a fitness center, zero-entry resort pools, and an on-site restaurant and lounge. The prime location places you just minutes from Disney parks, Universal Studios, and SeaWorld, as well as excellent local dining. Ownership is exceptionally effortless, as the HOA dues cover exterior maintenance, landscaping, cable, and internet. If that's not enough....Professional Short Term Management is already in place allowing the transition to be effortless, should you choose to keep their service! This won't last!! Call for your private viewing!

3008 Red Ginger Road, Kissimmee
8815 Dunes Court Unit 105, Kissimmee
$199,900
2 Beds ⋅ 2 Baths ⋅ Legacy Dunes Condo SubDv. ⋅ 34747 Zip Code
INCREDIBLE OPPORTUNITY UNDER $200,000 IN GATED LEGACY DUNES, JUST MINUTES FROM DISNEY! Whether you're looking for a vacation getaway, investment property, or full-time residence, this beautifully furnished 2-bedroom, 2-bathroom FIRST-FLOOR condo is an exceptional value in a resort-style community! Previously used as an Airbnb, this move-in-ready condo features ceramic tile flooring throughout, an updated kitchen with granite countertops, neutral-toned cabinetry, and newer appliances, including a washer and dryer. The bright, open floor plan provides a comfortable living space, while the screened-in patio is perfect for relaxing after a day enjoying everything Central Florida has to enjoy. The HOA includes internet, water, trash pickup, and pest control, making ownership even more convenient. Residents and guests can enjoy fantastic resort-style amenities, including TWO COMMUNITY POOLS, a clubhouse, fitness center, tennis and basketball courts, walking trails, and playgrounds. Conveniently located near Walt Disney World, shopping, dining, entertainment, and major roadways. Whether you're searching for a personal retreat or a property with rental potential, this condo is an opportunity you don't want to miss! SCHEDULE YOUR PRIVATE SHOWING TODAY!

8815 Dunes Court Unit 105, Kissimmee
3024 Parkway Boulevard Unit 304, Kissimmee
$158,900
1 Beds ⋅ 1 Baths ⋅ Blossom Park Villas A Condo SubDv. ⋅ 34747 Zip Code
Virtually Staged. Step into a turn-key piece of paradise just minutes from the Magic! This beautifully maintained, renovated 1-bedroom, 1-bathroom condo offers the ultimate setup for a short-term rental investment, vacation getaway, or low-maintenance secondary home. The interior features a bright, inviting open floorplan with modern updates throughout, offering comfort and convenience from day one. Unbeatably located roughly 5 miles from Walt Disney World, you are positioned minutes from Disney Springs, Universal Studios, Epic Universe, top-tier shopping, dining, and major highways (I-4 and US-192) for easy travel to Orlando International Airport. Hassle-free ownership is built right in, as the HOA dues cover electricity, water, internet, cable TV, trash, exterior maintenance, and community amenities—including a resort-style pool, clubhouse, fitness center, and tennis courts. A fantastic opportunity to own renovated, high-demand real estate in the heart of Orlando's attraction corridor!

3024 Parkway Boulevard Unit 304, Kissimmee
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