Kissimmee Homes with Sidewalks Community Features

Kissimmee Homes with Sidewalks Community Features

Welcome to Kissimmee, Florida, a vibrant city nestled in the heart of Osceola County, where the magic of the Sunshine State meets the charm of a close-knit community. Known for its warm climate, Kissimmee is a haven for families, retirees, and anyone seeking a lively atmosphere paired with natural beauty. With its proximity to world-renowned attractions like Walt Disney World and Universal Studios, residents enjoy a unique blend of excitement and tranquility.

One of the standout features of Kissimmee is its welcoming neighborhoods, many of which boast homes with sidewalks. These pedestrian-friendly communities create an inviting environment for families and neighbors to connect. Imagine evening strolls along tree-lined streets, where children can safely ride their bikes and neighbors can catch up over a friendly wave. Sidewalks encourage an active lifestyle, promoting walks to nearby parks, schools, and local shops.

Kissimmee's homes with sidewalks are not just about aesthetics; they foster a sense of belonging and community spirit. Many neighborhoods host seasonal events, from summer barbecues to holiday gatherings, allowing residents to bond and create lasting memories. The lush landscapes and thoughtfully designed homes enhance the overall appeal, making Kissimmee not just a place to live, but a place to thrive.

Whether you’re looking to invest in your first home or seeking a tranquil retirement retreat, Kissimmee offers a diverse range of properties that cater to every lifestyle. Come discover the charm of this enchanting city, where your dream home awaits amid the warmth and hospitality of Florida living.

Newest Kissimmee Homes with Sidewalks Community Features

4377 Quote Street, Kissimmee
$456,900
4 Beds ⋅ 3 Baths ⋅ Cove At Storey Lake Iii SubDv. ⋅ 34746 Zip Code
YOUR PERFECT ORLANDO VACATION GETAWAY OR INCOME-PRODUCING SHORT-TERM RENTAL INVESTMENT AWAITS IN THE HIGHLY SOUGHT-AFTER STOREY LAKE RESORT! This beautifully maintained, fully furnished 4-bedroom, 3-bathroom townhome offers an incredible opportunity for vacation homeowners and investors alike! ONE OF THE HOME'S STANDOUT FEATURES IS ITS LOCATION DIRECTLY ACROSS FROM A CHARMING PLAYGROUND! Enjoy convenient access to outdoor recreation just steps from your front door. Inside, enjoy a bright and spacious open-concept layout featuring a modern kitchen with a large center island, comfortable living and dining areas, and a convenient first-floor bedroom with a private bathroom. Upstairs, the primary suite and two additional bedrooms provide plenty of space for family and guests. Step outside to your own PRIVATE HEATED POOL WITH SCREENED LANAI, perfect for relaxing after a day exploring Orlando's attractions! ENJOY THE BEST OF RESORT-STYLE LIVING! Storey Lake features incredible amenities, including multiple resort pools, lazy rivers, waterslides, splash pads, fitness centers, restaurants, tiki bars, sports courts, mini-golf, and kayak rentals. The community’s newer second amenity center, Bronson’s Clubhouse, is just a 10-minute walk away, offering even more resort-style amenities and entertainment just steps from home! UNBEATABLE LOCATION! Just approximately 10 minutes from Walt Disney World, 20 minutes from SeaWorld, Universal Orlando, and Premium Outlets, and 30 minutes from Orlando International Airport. With short-term rentals permitted, this turnkey property is ideal as a family vacation retreat or income-producing investment. DON'T MISS THIS AMAZING OPPORTUNITY!

4377 Quote Street, Kissimmee
2428 Chateau Loop, Kissimmee
$415,000
4 Beds ⋅ 3 Baths ⋅ Tapestry Ph 3 SubDv. ⋅ 34741 Zip Code
Experience resort-style living in the desirable 24-hour security guard-gated Tapestry community! This beautiful two-story home features 4 bedrooms, 2.5 bathrooms, and a spacious two-car garage. The first floor offers easy-care tile flooring, while all four bedrooms are located upstairs for added privacy. Residents enjoy outstanding community amenities, including a resort-style swimming pool with water slide, splash park, fitness center, clubhouse, playground, sports field, BBQ pavilions, and scenic walking and biking trails. Ideally located just minutes from The Loop Shopping Center, restaurants, supermarkets, entertainment, and major roadways. Enjoy the perfect combination of comfort, convenience, and Florida resort-style living in a community.

2428 Chateau Loop, Kissimmee
2591 Santorini Divide, Kissimmee
$595,000
5 Beds ⋅ 5 Baths ⋅ Westside Cay SubDv. ⋅ 34747 Zip Code
Fully upgraded from floor to ceiling, this luxury townhome blends contemporary elegance with high-end functionality — designed specifically for short-term rental success. Located in the exclusive Doppio Westside community in Kissimmee, just 15 minutes from Walt Disney World, this 5-bedroom, 4.5-bath home features an open-concept layout with spacious integrated living, dining, and kitchen areas that flow seamlessly to your own private heated pool. The kitchen is a showstopper with two oversized islands, Level 5 quartz countertops, designer backsplash, slatted wood detail, and Whirlpool stainless steel appliances. All cabinetry throughout the home includes soft-close features and matte hardware for a sleek, modern finish. Each of the five bedrooms is designed with comfort and rental flexibility in mind — including four full en-suites and one located on the first floor. The bathrooms are finished with high-end porcelain tile, glass shower enclosures, built-in niches, and vessel sinks in select locations. Luxury vinyl plank flooring runs throughout the entire home — no carpet anywhere — and 5.5" square baseboards give a clean, elevated look. Additional features include PVC windows, a smart front door lock, a lockable owner’s closet, a hybrid water heater, thermostat, and 2 Car Parking Spot. Construction is full concrete block, including second floor, with an insulated "sandwich" roof system and rubber membrane roofing designed for durability and energy efficiency. Located within a gated community, Doppio Westside offers resort-style amenities such as a lagoon-style pool, full-service restaurant, clubhouse with front desk concierge, fitness center, playground, convention center, and EV charging stations — all exclusively zoned for short-term rental with no public school restrictions. Don't miss this opportunity to invest in one of Central Florida’s most unique STR communities — fully upgraded as standard, and built with both guest experience and investor return in mind.

2591 Santorini Divide, Kissimmee
5017 Laguna Bay Circle Unit 100, Kissimmee
$225,000
3 Beds ⋅ 2 Baths ⋅ Villas At Laguna Bay, Laguna Bay SubDv. ⋅ 34746 Zip Code
WELCOME TO THE VILLAS AT LAGUNA BAY – SHORT-TERM RENTALS ALLOWED! Amazing opportunity to own a beautifully situated 3-bedroom, 2-bathroom top-floor condominium offering approximately 1,220 square feet of comfortable living space in the heart of Central Florida. Whether you're looking for a primary residence, vacation home, or investment property, this condo offers outstanding flexibility in a desirable resort-style community. Step inside to a bright and inviting open-concept floor plan filled with natural light. Large bay windows enhance the main living and dining areas while providing peaceful views of the surrounding water and wooded landscape—the perfect setting to relax after a day enjoying everything Central Florida has to offer. The spacious primary suite provides a private retreat complete with an ensuite bathroom and tranquil views. Two additional bedrooms offer plenty of flexibility for family, guests, a home office, or additional sleeping accommodations. The well-designed floor plan also features interior laundry, generous living and dining spaces, and plenty of room for entertaining or simply enjoying everyday Florida living. Villas at Laguna Bay offers an impressive selection of resort-style amenities, including a community swimming pool, hot tub/spa, clubhouse, fitness center, sauna, tennis courts, playground, picnic and BBQ areas, and walking paths. Location is another major advantage! The community provides convenient access to Walt Disney World, Central Florida's major theme parks, shopping, restaurants, entertainment, US-192, and major roadways throughout the Orlando and Kissimmee area. With its top-floor location, peaceful water and wooded views, spacious three-bedroom layout, resort-style amenities, and short-term rental flexibility, this property presents an excellent opportunity to own a piece of Central Florida. Financing incentives may also be available for qualified buyers. Don't miss this opportunity—schedule your private showing today!

5017 Laguna Bay Circle Unit 100, Kissimmee
3377 Tranquil Trail, Kissimmee
$344,900
3 Beds ⋅ 3 Baths ⋅ Hub At Westside SubDv. ⋅ 34747 Zip Code
EXCELLENT OPPORTUNITY FOR HOMEOWNERS AND INVESTORS! Welcome to The Hub at Westside, a desirable community in the heart of Kissimmee, offering the perfect combination of comfort, convenience, and location! Built in 2023, this beautifully maintained two-story townhome features 3 spacious bedrooms, 3 full bathrooms, and approximately 1,360 square feet of thoughtfully designed living space. The bright, open-concept floor plan seamlessly connects the living, dining, and kitchen areas, creating an inviting atmosphere for everyday living and entertaining. The modern kitchen features stylish cabinetry, stainless steel appliances, generous counter space, and a functional layout. The property also offers two private en-suite bedrooms, providing added comfort, flexibility, and privacy. Enjoy the convenience of a low-maintenance lifestyle in a community featuring a resort-style clubhouse, swimming pool, fitness center, and gathering spaces. LOCATION, LOCATION, LOCATION! Ideally situated just minutes from Walt Disney World, major attractions, shopping, restaurants, and convenient access to major highways, this property offers an excellent opportunity for primary residents, second-home buyers, or investors looking to expand their rental portfolio in the growing Central Florida market. Whether you're searching for your next home or an investment property, this townhome delivers comfort, functionality, and exceptional location. Don't miss this opportunity! Schedule your private showing today and discover everything The Hub at Westside has to enjoy!

3377 Tranquil Trail, Kissimmee
2940 Benton Lane, Kissimmee
$462,000
4 Beds ⋅ 3 Baths ⋅ Oak Hammock Preserve Unit 1 SubDv. ⋅ 34746 Zip Code
SPACE, FLEXIBILITY & LOCATION! Welcome to this spacious home nestled in a desirable community, offering plenty of room to live, relax, and entertain! Designed with versatility in mind, this home features multiple living areas, providing endless possibilities for everyday living, entertaining, or creating your ideal space. In addition to the generously sized bedrooms, you’ll find a bonus fifth room that can be customized to suit your needs, whether you envision a home office, fitness room, creative studio, or additional flex space. Enjoy the convenience of community amenities, including a refreshing community pool, perfect for soaking up the Florida sunshine without the maintenance of a private pool. With its spacious layout, flexible living options, and inviting neighborhood atmosphere, this property offers an incredible opportunity to make it your own. Existing FHA mortgage may be eligible for assumption by a qualified buyer, subject to lender approval and applicable requirements. Inquire for additional details! Don’t miss your opportunity to explore everything this home has. Schedule your private showing today!

2940 Benton Lane, Kissimmee
1835 Caribbean View Terrace, Kissimmee
$750,000
9 Beds ⋅ 6 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Your perfect retreat in Kissimmee! This spectacular, fully furnished two-story property combines spaciousness, style, and ultimate comfort, making it ideal for everyday living or the vacation rental market. With 9 spacious bedrooms and 6 full bathrooms, the layout offers the perfect space to accommodate large families or groups with complete privacy. The master suite stands out for its generous size and private walk-in closet, while the additional bedrooms feature built-in closets. The ground floor seamlessly integrates the living and dining areas in an open-concept layout filled with natural light. The kitchen blends elegance and functionality, featuring solid wood cabinetry, stone countertops, and included appliances. Additionally, there is a separate laundry room equipped with a washer and dryer. The living space is complemented by an incredible themed game room and a private outdoor oasis—featuring an in-ground pool with a spa and a screened-in lanai, perfect for enjoying the Florida weather year-round. The property includes an attached 2-car garage and boasts a prime location near major roadways, shops, restaurants, and highly-rated schools. A turnkey gem ready to be enjoyed or rented out from day one!

1835 Caribbean View Terrace, Kissimmee
3210 Guana Way, Kissimmee
$320,000
4 Beds ⋅ 3 Baths ⋅ West Lucaya Village SubDv. ⋅ 34747 Zip Code
Amazing 4BR/3BA Furnished Townhome Resort-Style in Kissimmee near Disney, live or rent this bright, elegant and spacious property that give you an ultimate flexibility whether you are looking for OWNER OCCUPIED as a First or Second home or as INVESTOR of a high potential rental property, SHORT TERM OR LONG-TERM RENT zoned. Enjoy a modern turnkey layout with plenty of space for family, guests, tourists or tenants. Prime Central Florida location, just minutes from major attractions as world famous Disney parks, shopping malls, restaurants, and entertainment. Easy access to major road makes trips to Orlando and the area top attractions quick and convenient. Act now to schedule your showing today!

3210 Guana Way, Kissimmee
3200 Guana Way, Kissimmee
$320,000
4 Beds ⋅ 3 Baths ⋅ West Lucaya Village SubDv. ⋅ 34747 Zip Code
Amazing 4BR/3BA Furnished Townhome Resort-Style in Kissimmee near Disney, live or rent this bright, elegant and spacious property that give you an ultimate flexibility whether you are looking for OWNER OCCUPIED as a First or Second home or as INVESTOR of a high potential rental property, SHORT TERM OR LONG-TERM RENT zoned. Enjoy a modern turnkey layout with plenty of space for family, guests, tourists or tenants. Prime Central Florida location, just minutes from major attractions as world famous Disney parks, shopping malls, restaurants, and entertainment. Easy access to major road makes trips to Orlando and the area top attractions quick and convenient. Act now to schedule your showing today!

3200 Guana Way, Kissimmee
2966 Lucayan Harbour Circle Unit 103, Kissimmee
$270,000
3 Beds ⋅ 2 Baths ⋅ Lucaya Village Ph 1 SubDv. ⋅ 34746 Zip Code
LOCATION, LOCATION, LOCATION, Resort-Style near Disney, discover an extraordinary opportunity to own this amazing bright, spacious and fully furnished, three-bedroom, two-bathroom Townhome in a gate community near Disney Parks, enjoy a resort-style setting with shopping, dining, and entertainment just steps away from the community. Whether you are looking for a comfortable life as a FIRST Or SECOND HOME BUYER or if you are an INVESTOR, this townhome offers a high rental potential, for SHORT OR LONG-TERM RENT. Its appealing combination of great location, amenities and flexibility and its proximity to Central Florida major attractions make the difference. Act now schedule your showing today!

2966 Lucayan Harbour Circle Unit 103, Kissimmee
4447 Scene Lane, Kissimmee
$539,990
4 Beds ⋅ 3 Baths ⋅ Cove At Storey Lake 5 SubDv. ⋅ 34746 Zip Code
This charming townhouse, located in the desirable Storey Lake community, offers a fantastic vacation experience with a private pool and plenty of space for up to 10 guests. The home features 4 bedrooms and 3 bathrooms, with the first floor offering a cozy bedroom with a Queen bed, accommodating 2 guests with a bathroom just down the hallway. On the second floor, the master suite includes a King bed and a private bathroom, perfect for 2 guests. There are two themed rooms: one with a Mickey theme featuring a Full bed and a Twin bed (sleeps 3), and another with an Avengers theme offering a Full bed and a Twin bed (sleeps 3), both sharing a bathroom in the hallway. The home is fully equipped with everything you need for a comfortable stay, including a cozy living and dining area, a fully equipped kitchen with a dishwasher, a washer and dryer, and new linens for bed, bath, and table. Additional amenities include board games, a PS5 video game console, free high-speed Wi-Fi, cable TV, and free local calls. Guests can enjoy the private pool and access to the community’s recreational area. Please note that the use of the grill and pool heating are available for an additional fee, and certain activities in the recreational area may require on-site payment, such as arcade games, kayaking, and mini-golf. The home’s prime location makes it ideal for visiting Orlando's top attractions, with Walt Disney World just 20 minutes away (16 km) and Universal Studios around 25 minutes (22 km) from your doorstep. Whether you’re here for a family getaway or a group trip, this home offers everything you need for a relaxing and memorable stay.

4447 Scene Lane, Kissimmee
5025 Windermere Avenue, Kissimmee
$519,990
4 Beds ⋅ 3 Baths ⋅ Storey Lake Ph 3 SubDv. ⋅ 34746 Zip Code
Welcome to your dream vacation retreat in the highly desirable Storey Lake Resort! This stunning, professionally decorated and fully furnished home is ready to deliver both unforgettable family experiences and immediate rental income. Perfectly located in the heart of Orlando, just minutes from Walt Disney World, Universal Studios, SeaWorld, and Orlando International Airport, with premier shopping, dining, and golf all nearby—this is Central Florida living at its best! Featuring 4 spacious bedrooms and 3 full bathrooms, this home is a standout with its thoughtfully designed themed bedrooms, including a magical Mickey Mouse room and a playful Minions room—perfect for delighting guests of all ages. Additional highlights include upgraded tile and carpet throughout, quartz countertops, stainless steel appliances, and an inviting open-concept living area that flows seamlessly to your private screened-in pool. Whether you're an investor looking for a high-performing short-term rental or a family searching for the perfect second home, this property offers incredible value, style, and location. As part of Storey Lake, you’ll enjoy resort- style amenities such as a stunning clubhouse, sparkling swimming pool, lazy river, waterslides, splash pad, mini-golf, fitness center, sports courts, and so much more. Don't miss this rare opportunity—homes like this in Storey Lake don’t last long! Schedule your showing today!

5025 Windermere Avenue, Kissimmee
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