Kissimmee Homes with Tennis Court(s) Exterior Features

Kissimmee Homes with Tennis Court(s) Exterior Features

Welcome to Kissimmee, Florida – a vibrant city that beautifully blends the charm of small-town living with the excitement of nearby attractions. Nestled just south of Orlando, Kissimmee is renowned for its stunning landscapes, diverse recreational opportunities, and family-friendly atmosphere. This city is not only a gateway to world-famous theme parks like Walt Disney World and Universal Studios, but it also boasts a rich cultural heritage, abundant parks, and scenic lakes that beckon outdoor enthusiasts year-round.

For those seeking a home that caters to an active lifestyle, Kissimmee offers a selection of exquisite properties featuring tennis courts right in your backyard. Imagine stepping outside your door to a private oasis where you can enjoy a friendly match with friends or practice your serve under the Florida sun. These homes with tennis courts not only provide a fantastic way to stay fit but also create a perfect setting for entertaining guests or enjoying quality family time.

The exterior features of these residences often include beautifully landscaped gardens, spacious patios, and luxurious outdoor living spaces that enhance the overall appeal. Whether you’re a seasoned player or a casual enthusiast, having a tennis court at home elevates your living experience and fosters a sense of community right outside your door.

Kissimmee is more than just a place to live; it’s a lifestyle. With its warm climate, rich recreational offerings, and welcoming neighborhoods, this city is the perfect backdrop for your dream home. Explore the possibilities of owning a property with a tennis court and embrace the active, vibrant lifestyle that Kissimmee has to offer!

Newest Kissimmee Homes with Tennis Court(s) Exterior Features

$330,000
4 Beds ⋅ 4 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Turnkey 4BR/3.5BA End-Unit Villa in Regal Oaks Resort — Miles to Disney Renovated and carpet-free throughout, this 4-bedroom, 3.5-bath end-unit townhome in the gated Regal Oaks Resort offers sleeping capacity for up to 10 — an ideal short-term rental investment, second home, etc, just miles from the Walt Disney World entrance and walking distance to Old Town and Fun Spot. The home is currently operating as a successful short-term rental and conveys fully furnished — a true turnkey opportunity for a buyer to assume operations at closing. Each bedroom is fully furnished with a flat-screen TV, dresser, and closet. The home includes a spacious living area, fully equipped kitchen, and full-size washer/dryer. Dual master suites provide flexibility and privacy: a first-floor master with a Disney Mickey Mouse theme, queen bed plus extra-long twin, and full en-suite bath; and a second-floor master with a king bed, en-suite bath, walk-in closet, and private balcony. Two additional upstairs bedrooms share a third full bath. A half bath completes the main floor. Ownership includes access to Regal Oaks' resort-style clubhouse amenities: pools with water slides, spa, fitness center, tiki bar, on-site restaurant, game room, tennis courts, convenience shop, etc. Unbeatable location: several miles to Disney, 8.5 to SeaWorld, 12.3 to Universal. Old Town and Fun Spot are walkable; Celebration Town Center is 3 miles; Publix is 1.2 miles and Super Target 3 miles. Multiple golf courses and dinner shows are within 3–12 miles. Sold as-is with right to inspect. Buyer and buyer's agent to verify all room dimensions, square footage, HOA fees, lease restrictions, HOA regulation, etc

2700 Camaro Drive, Kissimmee
$330,000
3 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Fully furnished and beautifully decorated 3-bedroom townhome in Regal Oaks at Old Town, a gated resort community where short-term rentals are permitted, just approximately 3 miles from the entrance to Walt Disney World. This two-story home features a spacious screened patio overlooking a wooded area, offering exceptional privacy and a peaceful setting for relaxing or entertaining. It offers 3 bedrooms and 2.5 baths. The open-concept main level features a granite kitchen with wood cabinetry and stainless-steel appliances, flowing into the dining and living areas. Sliding glass doors open to a screened lanai with a private hot tub, an upgraded feature beyond the standard unit in the community. A convenient half bath completes the first floor. The home features durable hard-surface flooring throughout with no carpet, and the interior was freshly painted in 2025. Upstairs, the primary suite includes a private bath with dual sinks, while two additional bedrooms share a second full bath. A full-size washer and dryer are also included. Owners and guests enjoy access to the extensive Regal Oaks resort amenities, including multiple pools with water slides, a spa, poolside bar, on-site restaurant and market, fitness center, tennis courts, game room, and gated entry. Currently operating as a short-term rental with an established booking history, the property is offered fully turnkey. The sale includes furniture, televisions, wall art, mirrors, décor, linens, towels, cookware, dinnerware, small appliances, and the existing appliances, washer, and dryer. The buyer may continue the existing rental operation, use the home as a personal vacation property, occupy it directly, or enjoy a combination of personal use and rental income. Prime location near Orlando's top attractions: Old Town adjoins the community, Fun Spot is approximately 0.5 mile away, Publix is about 1.2 miles, Celebration and Super Target approximately 3 miles, Premium Outlets approximately 7 miles, SeaWorld approximately 8.5 miles, and Universal Orlando approximately 12 miles. Sold as-is with right to inspect. Buyer and buyer's agent to independently verify all room dimensions, square footage, HOA fees, lease and rental restrictions, and regulations, etc.

5710 Olga Street, Kissimmee
$249,000
3 Beds ⋅ 3 Baths ⋅ Emerald Island Resort Ph 2 SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom Townhome located in the highly sought-after Emerald Island Resort, one of Kissimmee's premier gated short-term rental communities! Featuring an inviting open-concept floor plan, this home is designed for comfortable living and effortless entertaining. Tile flooring flows throughout the entire first floor, while the freshly painted downstairs ceiling enhances the abundant natural light, creating a bright and welcoming atmosphere. All three bedrooms are conveniently located on the second floor, providing privacy and a functional layout. The spacious primary suite features its own private balcony, the perfect place to enjoy your morning coffee or unwind in the evening. Recent updates include new luxury flooring in both full bathrooms along with new American Standard toilets, adding a fresh, modern touch. Step outside to enjoy the covered rear porch, offering a comfortable space to relax or entertain. This home is being sold fully furnished, making it an excellent opportunity as a primary residence, vacation home, or turnkey investment property in one of Central Florida's most popular short-term rental communities. Emerald Island Resort offers outstanding resort-style amenities, including 24/7 manned gated security, a community pool, tennis courts, mini golf, beach volleyball, basketball courts, fitness center, an on-site café, EV chargers at the Clubhouse and weekly community events for residents and guests. Conveniently located just minutes from Walt Disney World, shopping, dining, golf, and major highways, this home offers the perfect blend of comfort, convenience, and resort living.

8454 Crystal Cove Loop, Kissimmee
$570,000
5 Beds ⋅ 5 Baths ⋅ Bellalago SubDv. ⋅ 34746 Zip Code
Virtually Staged. SPACE, PRIVACY & RESORT-STYLE LIVING IN BELLALAGO! Welcome to 1711 Windward Oaks Ct, an impressive 5-bedroom, 5.5-bath residence situated on an oversized 0.46-acre cul-de-sac lot in the sought-after gated community of Bellalago. Offering exceptional space, privacy and versatility, this home is ideal for a growing household, frequent guests or multigenerational living, with a generous bedroom and bathroom configuration that allows everyone to enjoy their own space. The expansive floor plan features multiple living areas designed for comfortable everyday living and entertaining, while the three-car garage provides plenty of room for vehicles, storage, bikes and recreational gear. One of the home's standout features is the oversized enclosed porch overlooking beautiful open green space. Whether enjoying morning coffee, gathering with family and friends or simply unwinding at the end of the day, this peaceful outdoor living area provides a wonderful extension of the home with added privacy and tranquil views. Beyond the home, Bellalago delivers the Florida lifestyle with an impressive array of resort-style amenities. Residents enjoy multiple pools, including a Junior Olympic pool, an interactive water park, fitness facilities, tennis and pickleball courts, basketball and volleyball, playgrounds, a dog park, walking and recreational areas, clubhouse facilities and community activities. On-site dining adds even more convenience and creates a great place to gather and socialize without leaving the neighborhood. Bellalago's location along beautiful Lake Tohopekaliga brings waterfront recreation right into the community, with fishing areas, boardwalks and private boat-ramp access for residents to enjoy boating and the outdoors. Everyday conveniences are also close at hand, with shopping, dining and services located just outside the community. With nearly half an acre, a desirable cul-de-sac setting, five bedrooms, five-and-a-half bathrooms, a three-car garage, expansive indoor and outdoor living spaces, peaceful green-space views and an exceptional resort-style community, this home offers much more than square footage—it offers the space and flexibility to fit today's lifestyle.

1711 Windward Oaks Court, Kissimmee
$474,900
4 Beds ⋅ 3 Baths ⋅ Reunion Village Ph 4 & 5 SubDv. ⋅ 34747 Zip Code
TURNKEY short-term rental business for sale, 2nd vacation home, or lovely primary home for your family. YOU CHOOSE!! Sale of this New 2025 home build will come with all future bookings for this property AND ALL WARRANTIES!! 1st floor features a deep and open 1st floor floorplan tastefully staged for your imagination. A chef-ready kitchen awaits with a nice sized pantry and defined dining area. 1st floor master suite removes w/ laundry facilities for your visitors/in-laws. Home has been tastefully staged to spark you imagination. 2nd floor features an upstairs bonus loft w/ it's own walk-in closet can customize into a game room, home office or an extra sitting space for guests! All other bdrms are upstairs including another master bedroom. The community features luxury resort style living. amenities including a waterparks complete with 7pools, Tennis Courts, Playground, 10 restaurants, and much MUCH MORE!! Close to all major theme parks (located 5mins from Disney parks), championship golf courses, shopping, downtown Orlando areas, and dining. Long & Short term rentals are allowed. **Also eligible for the GOVERNMENT BACKED Rent to own program** Easy to Show!! Call now to book your appt!

7745 Somersworth Drive, Kissimmee
$265,000
2 Beds ⋅ 3 Baths ⋅ Summerfield Twnhms SubDv. ⋅ 34741 Zip Code
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
$215,000
3 Beds ⋅ 2 Baths ⋅ Villas At Somerset The SubDv. ⋅ 34746 Zip Code
Virtually Staged. Move-In Ready First-Floor Condo – Resort-Style Living & Investment Opportunity! Welcome home to this move-in ready first-floor condo, offering the perfect opportunity for both investors and primary homeowners. Enjoy a resort-style lifestyle with exceptional community amenities, including tennis courts, basketball courts, a fitness center, community pool, clubhouse, and more. This well-maintained condo provides convenient first-floor living with easy access and a comfortable layout designed for everyday enjoyment. Whether you are looking for a full-time residence, vacation home, or investment opportunity, this property offers flexibility to meet your needs. The seller is open to long-term rental opportunities, making this an attractive option for investors seeking rental potential. Don’t miss the opportunity to own a condo in a desirable community with great amenities and a convenient location. Schedule your showing today!

2723 N Poinciana Boulevard Unit 153, Kissimmee
$227,000
3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 6 SubDv. ⋅ 34747 Zip Code
Short Sale. SHORT-SALE OPPORTUNITY IN WINDSOR PALMS! This fully furnished 3-bedroom, 2-bath condo offers approximately 1,268 square feet in a gated resort community just minutes from Walt Disney World. Suitable for personal occupancy, a vacation home, or short- or long-term rental use, subject to applicable association rules, licensing, and governmental requirements. Documented 2023 updates include the A/C system, luxury vinyl flooring, interior paint, granite countertops, bathroom vanities and sinks, kitchen sink, dishwasher, and washer/dryer. Televisions were updated in 2025. Community amenities include gated entry, resort-style pool, clubhouse, sports courts, movie theater, arcade, and bar. Conveniently located near Disney-area attractions, shopping, dining, entertainment, major roadways, and Orlando-area airports. Sale price, terms, and closing timeline require the seller’s lender approval. Buyer must verify measurements, property condition, included furnishings, HOA fees and assessments, rental requirements, licensing, insurance, financing, and association information.

8107 Coconut Palm Way Unit 201, Kissimmee
$164,000
1 Beds ⋅ 1 Baths ⋅ Villas Del Sol At Kissimmee Condo SubDv. ⋅ 34741 Zip Code
Beautiful freshly painted and well-maintained 1-bedroom, 1-bath condo with a bonus room, 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 first floor with direct access to parking. This unit has been fully renovated with laminate flooring throughout the entire unit. 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. Unit is VACANT. Move-in ready.

2208 Antigua Place Unit 914, Kissimmee
$475,000
3 Beds ⋅ 4 Baths ⋅ Magic Village Resort 2 SubDv. ⋅ 34747 Zip Code
LOCATION, LOCATION, LOCATION! Just minutes from Walt Disney World, this stunning fully furnished vacation home is located in the highly sought-after Magic Village Resort. Whether you're looking for a luxury vacation retreat or a high-performing investment property, this home is an exceptional opportunity. Enjoy world-class resort amenities, including a spectacular swimming pool, fitness center, concierge services, a convenience store, conference facilities, and an on-site restaurant offering both indoor and outdoor dining. This turnkey property has an established rental history with excellent guest reviews and strong year-round rental potential. Its prime location provides convenient access to Disney, championship golf courses, shopping, dining, and Orlando's top attractions. Don't miss this opportunity to own a luxury vacation home in one of Central Florida's premier resort communities!

7540 Brooklyn Drive, Kissimmee
$575,000
8 Beds ⋅ 6 Baths ⋅ Windsor/Westside-Ph 2a SubDv. ⋅ 34747 Zip Code
Short Sale. Welcome to your own slice of paradise in the highly sought-after, guard-gated Windsor at Westside Resort! This beautifully updated and fully furnished 8-bedroom, 6-bath home offers over 4,041 square feet of spacious living designed for comfort, entertainment, and unforgettable vacation experiences. The versatile floor plan features a convenient first-floor primary suite, while two upstairs bedrooms include private en-suite baths for added privacy. Enjoy Florida living year-round in your private heated pool and spa, or gather family and guests in the incredible converted game room complete with gaming consoles, a pool table, and driving simulators. Located just minutes from Disney, this exceptional resort home provides access to world-class amenities, including a resort-style pool, lazy river, expansive clubhouse, fitness center, poolside cabana, sand volleyball courts, and tennis courts. Whether you're looking for a vacation retreat, primary residence, or income-producing investment property, this move-in-ready home offers the perfect blend of luxury, location, and resort-style living.

1836 Nice Court, Kissimmee
$249,000
4 Beds ⋅ 3 Baths ⋅ Venetian Bay Village Condo Ph 1 SubDv. ⋅ 34741 Zip Code
Resort-style living in the guard-gated Venetian Bay Villages just minutes from Walt Disney World, offering a spacious 4-bedroom, 3-bathroom townhome ideal for a primary residence, vacation home, or short-term rental investment. This two-story townhome-style condominium offers approximately 1,470 square feet of living space with a functional layout designed for comfort and flexibility. The open-concept living and dining area flows into the kitchen, creating a welcoming space for entertaining family and guests. The primary bedroom suite is conveniently located on the first floor, while three additional bedrooms upstairs provide ample space for guests, family members, or vacation renters. Located within the desirable Venetian Bay Villages resort community, residents enjoy access to a wide range of amenities including multiple community pools, tennis courts, basketball courts, volleyball courts, playgrounds, a clubhouse with fitness center, picnic and grilling areas, and beautifully maintained grounds inside a 24-hour guard-gated community. Conveniently situated in the heart of Central Florida, the property is just minutes from Disney World, Universal Studios, Disney Springs, The Loop shopping and dining district, major highways, and Orlando International Airport. Short-term rentals are permitted with a minimum one-week lease period, making this an excellent opportunity for investors or those seeking a vacation home near Orlando’s top attractions. Whether you're looking for a Kissimmee investment property, vacation retreat, or full-time residence, this Venetian Bay Villages home offers the perfect combination of location, lifestyle, and income potential.

4021 Venetian Bay Drive Unit 101, Kissimmee
Start Your Search