Kissimmee (Downtown East) Homes with Tennis Court(s) Exterior Features

Kissimmee (Downtown East) Homes with Tennis Court(s) Exterior Features

Welcome to Downtown East Kissimmee, a vibrant gem nestled in the heart of Osceola County, Florida. Known for its charming neighborhoods and a welcoming community atmosphere, this area is perfect for families, retirees, and everyone in between. With its close proximity to the enchanting attractions of Central Florida, including Disney World and Universal Studios, Downtown East Kissimmee offers an ideal blend of suburban tranquility and urban excitement.

One of the standout features of homes in this delightful region is the inclusion of private tennis courts. Imagine stepping out of your beautifully appointed residence and onto your very own court, where you can enjoy a friendly match with family and friends or hone your skills in the Florida sunshine. These homes not only cater to tennis enthusiasts but also provide a perfect space for outdoor gatherings and leisure activities.

The architectural styles in Downtown East range from cozy single-family homes to spacious estates, each offering unique exterior features that enhance their curb appeal. Lush landscaping, inviting patios, and serene backyards create a picturesque setting for relaxation and entertainment. The community is also well-connected, with easy access to shopping, dining, and recreational facilities, making it a convenient choice for those who appreciate an active lifestyle.

Whether you’re looking for a primary residence or a vacation retreat, Downtown East Kissimmee’s homes with tennis courts present an extraordinary opportunity to embrace the Florida lifestyle. Discover the charm of this community and find your perfect home today!

Newest Kissimmee (Downtown East) Homes with Tennis Court(s) Exterior Features

2210 Grand Cayman Court Unit 1733, Kissimmee
$180,000
2 Beds ⋅ 2 Baths ⋅ S5159978 MLS ⋅ 2210 BLDG.
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
4005 Venetian Bay Drive Unit 108, Kissimmee
$249,000
4 Beds ⋅ 3 Baths ⋅ O6450830 MLS ⋅ 6 BLDG.
WELCOME TO VENETIAN BAY VILLAGES! Discover this charming, FULLY FURNISHED, two-story condominium located in a beautiful GATED, RESORT-STYLE COMMUNITY in the heart of Kissimmee! Perfect for a primary residence, vacation getaway, or investment opportunity, this property allows SHORT-TERM RENTALS WITH A MINIMUM STAY OF 7 DAYS! Step inside to a bright, inviting interior with a fully equipped kitchen, breakfast bar, spacious bedrooms, tasteful furnishings, and comfortable living spaces. Move-in ready and beautifully presented, this home offers convenience and flexibility from day one! Enjoy RESORT-STYLE AMENITIES, including a sparkling community pool, fitness center, playground, and beautifully landscaped surroundings. Conveniently located near Disney attractions, shopping, dining, entertainment, and major highways. Whether you’re looking for your Florida retreat or an income-producing investment opportunity, this property offers the perfect combination of LOCATION, LIFESTYLE, AND RENTAL FLEXIBILITY! SCHEDULE YOUR PRIVATE SHOWING TODAY!

4005 Venetian Bay Drive Unit 108, Kissimmee
4004 Santa Maria Drive Unit 101, Kissimmee
$239,900
4 Beds ⋅ 3 Baths ⋅ O6449552 MLS ⋅ 49 BLDG.
An exciting opportunity is coming to one of Kissimmee's established gated communities! This spacious 4-bedroom, 3-bathroom condo offers a versatile layout, resort-style community amenities, and a convenient location near shopping, dining, entertainment, and major Central Florida attractions. Whether you're looking for a primary residence, a Florida getaway, or an investment opportunity, this property is worth keeping an eye on. Stay tuned for more details and photos!

4004 Santa Maria Drive Unit 101, 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
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
2207 Antigua Place Unit 727, Kissimmee
$133,000
1 Beds ⋅ 1 Baths ⋅ S5158130 MLS ⋅ 2207 BLDG.
Beautiful freshly painted and well-maintained 1-bedroom, 1-bath condo, the unit is located in the gated, resort-style community of Villa del Sol, with controlled access through the Envera system. The unit is in the second floor with direct access to parking. The bedrooms has spacious walk-in closets. The community buildings have recently been updated with a modern exterior color palette and is very well maintained. Amenities include a clubhouse, fitness center, two swimming pools, on-site laundry facilities, car wash area, BBQ/picnic areas, playground, tennis courts and much more. Excellent opportunity for primary residence or investment. Located near to the Loop Mall with very close access to the Osceola Parkway, 192, 4-17, I-4, Restaurants, parks and attractions. Short rental allowed

2207 Antigua Place Unit 727, Kissimmee
1213 Bermuda Lakes Lane Unit 208, Kissimmee
$200,000
3 Beds ⋅ 2 Baths ⋅ S5157399 MLS ⋅ 1213 BLDG.
Beautifully renovated and truly move-in ready 3-bedroom, 2-bath condo located in the desired Gables at Lakeside community. This spacious unit features a private individual entrance and a peaceful pond view from the front porch — the perfect place to enjoy your morning coffee or unwind in the evening. Inside, you’ll find modern updates, a bright and open layout, and comfortable living spaces designed for everyday living. The community offers fantastic amenities including a swimming pool, fitness center, and tennis court, all within a super quiet and well-maintained environment. Conveniently located near shopping, mall, dining, major highways, and local attractions, this property is ideal as a primary residence or investment opportunity. Don’t miss the chance to own a fully updated condo in one of Kissimmee’s most convenient locations.

1213 Bermuda Lakes Lane Unit 208, Kissimmee
2260 San Vital Drives Unit 108, Kissimmee
$240,000
4 Beds ⋅ 3 Baths ⋅ S5155747 MLS ⋅ Venetian Bay Village Condo BLDG.
EXCELLENT INVESTMENT OPPORTUNITY OR FLORIDA VACATION HOME! Welcome to 2260 San Vital Dr #108, a spacious 4-bedroom, 3-bathroom residence located in the desirable guard-gated resort community of Venetian Bay Villages in Kissimmee. This property offers an excellent combination of comfort, convenience, and investment potential, with short-term rentals permitted. “Beautifully updated property featuring three completely renovated bathrooms with new flooring. The entire second floor has also been upgraded with new flooring, replacing all previous carpeting. The home features a desirable dual-primary-suite floor plan, with one primary en-suite conveniently located on the first floor and a second private primary suite upstairs. The main level offers an open living and dining area with high ceilings and abundant natural light, along with a functional kitchen and breakfast bar. Two additional bedrooms share a full bathroom, providing plenty of space for family and guests. Property is offered unfurnished. Venetian Bay Villages offers an impressive selection of resort-style amenities, including 24/7 guard-gated security, four community swimming pools, a clubhouse, fitness center, movie theater, game room/arcade, business center, tennis and basketball courts, volleyball, playgrounds, picnic areas, and walking trails. Ideally located near Central Florida's world-famous attractions, shopping, dining, and major roadways, this property provides convenient access to Disney, Universal Orlando, SeaWorld, and everything the Orlando/Kissimmee area provides. With short-term rentals permitted, including Airbnb/VRBO, this property is an excellent option for investors, a vacation home, or a primary residence. Schedule your private showing today and discover all that Venetian Bay Villages provides!

2260 San Vital Drives Unit 108, Kissimmee
2448 Summerfield Way, Kissimmee
$255,000
2 Beds ⋅ 3 Baths ⋅ O6431463 MLS
Welcome to 2448 Summerfield Way, Kissimmee, FL — a beautifully updated 2-bedroom, 2-bathroom condo that is move-in ready and perfectly positioned in the heart of Central Florida. From the moment you step inside, you will notice the thoughtful updates throughout that make this home truly turnkey. Whether you are settling in for the first time or adding to your investment portfolio, this property delivers the comfort, style, and value that today's buyers are looking for. The location is one of this home's greatest assets. Centrally situated with easy access to all major highways, you are just minutes from Walt Disney World, Universal Studios, SeaWorld, Orlando International Airport, The Loop Mall, premier dining, and world-class shopping. Everything Central Florida has to offer is practically at your doorstep. This is the kind of property that appeals to everyone — first-time buyers, families, and investors alike. Rental demand in this corridor is among the strongest in the region, making this an excellent income-producing opportunity as well. Updated. Centrally located. Move-in ready. Do not wait — properties like this at this price point in this location do not stay on the market long. Schedule your private showing today

2448 Summerfield Way, Kissimmee
1601 Columbia Arms Circle Unit 201, Kissimmee
$185,000
2 Beds ⋅ 2 Baths ⋅ O6407642 MLS ⋅ 1601 BLDG.
Stunning 2-bedroom, 2-bath condominium with 1-car garage! This beautifully maintained home offers a bright and airy open-concept design, perfect for both everyday living and entertaining, ideally located next to the community clubhouse, offering easy access to amenities and enhancing your lifestyle. Enjoy two spacious master suites, each featuring its own walk-in closet, providing comfort, privacy, and flexibility. Elegant laminate flooring flows seamlessly throughout the entire home, creating a modern and cohesive feel. The kitchen is equipped with a gas stove, perfect for those who love to cook, and features recent upgrades including a brand-new refrigerator (2025), new microwave (2025), and new garbage disposal (2025). The A/C unit was replaced in 2019. Additional highlights include a convenient inside laundry room and a well-designed layout that maximizes both space and functionality. This move-in ready condo offers the perfect combination of style, comfort, and low-maintenance living—a true must-see!

1601 Columbia Arms Circle Unit 201, Kissimmee
4017 Venetian Bay Drive Unit 103, Kissimmee
$199,000
3 Beds ⋅ 2 Baths ⋅ O6407344 MLS ⋅ 17 BLDG.
This beautifully furnished 3-bed, 2-bath townhouse offers a warm, turnkey living experience inside the gated, resort-style community of Venetian Bay Village. Designed for comfort and convenience, the home features a welcoming open layout, tasteful décor, and all essential furnishings—perfect for long-term living, short-term rental, or a fully equipped second home.Venetian Bay Village is known for its resort-style amenities and peaceful, well-kept grounds, including: Multiple swimming pools, including a heated main pool,Clubhouse, fitness center, and game room,Tennis, volleyball, and basketball courts Playgrounds, picnic areas, 24-hour gated security for peace of mind. The Loop shopping & dining is close by, Disney, Universal, and major attractions

4017 Venetian Bay Drive Unit 103, Kissimmee
4012 Santa Maria Drive Unit 102, Kissimmee
$215,000
4 Beds ⋅ 3 Baths ⋅ S5142432 MLS ⋅ 56 BLDG.
Beautiful 4-bedroom, 3-bath corner townhome- located in the guard-gated community of Venetian Bay Villages. Conveniently situated near major attractions, Orlando International Airport, The Loop shopping center, and main roadways. The community offers 3 pools, including a main heated pool open until late daily, as well as a fitness room and theater next to the clubhouse. Additional amenities include a beach volleyball court, basketball and tennis courts, and 2 satellite pools with play areas throughout the neighborhood. This property offers a great location within a resort-style setting. Short term rentals are allowed. Schedule your showing today!

4012 Santa Maria Drive Unit 102, Kissimmee
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