Kissimmee Homes with Sidewalks Community Features

Kissimmee Homes with Sidewalks Community Features

Welcome to Kissimmee, Florida – a vibrant city where sunshine and charm come together to create the perfect backdrop for your dream home! Nestled in the heart of Central Florida, Kissimmee is renowned for its proximity to world-famous attractions, including Walt Disney World, Universal Studios, and a plethora of outdoor adventures. With its warm climate, friendly atmosphere, and rich cultural heritage, Kissimmee is not just a place to live; it’s a lifestyle waiting to be embraced.

One of the standout features of Kissimmee is its welcoming communities, particularly those with sidewalks that encourage a sense of connection among neighbors. Homes in these communities are designed with your comfort and convenience in mind, featuring spacious layouts and modern amenities. The sidewalks provide a safe and inviting space for morning strolls, evening jogs, or leisurely bike rides, fostering a sense of community and encouraging an active lifestyle.

Imagine waking up to the sound of birds chirping and stepping outside to enjoy your morning coffee while taking in the picturesque views of tree-lined streets. These neighborhoods are not just about the homes; they’re about the lifestyle they promote. With parks, playgrounds, and community events just a stone’s throw away, your family will have endless opportunities to connect, play, and grow.

Kissimmee is more than a destination; it’s a community where memories are made, friendships are forged, and life is lived to the fullest. Explore the homes with sidewalks in Kissimmee and discover the perfect place to call home in this enchanting city!

Newest Kissimmee Homes with Sidewalks Community Features

3 Beds ⋅ 2 Baths ⋅ Lucaya Village Ph 2 SubDv. ⋅ 34746 Zip Code

Welcome to this beautifully renovated and fully furnished townhome located in the highly desirable Lucaya Village Resort! This move-in-ready property features updated interiors, new appliances, and a bright, open-concept living and dining area designed for comfort and functionality. One of the highlights of this home is its convenient location within the community, offering parking spaces directly in front of the property and easy access to the clubhouse, playground, community amenities, and beautiful green areas with ponds, creating a relaxing resort-style setting just steps from your door. Lucaya Village is known for its excellent location in the Kissimmee/Orlando area, providing convenient access to major roads, shopping, dining, entertainment, and Central Florida’s world-famous attractions. Whether you're looking for a vacation home, investment property, or your own Florida retreat, this renovated and well-maintained townhome offers an excellent combination of location, convenience, and resort-style living. Schedule your showing today!

5356 Diplomat Court Unit 102, Kissimmee

15 Beds ⋅ 16 Baths ⋅ Veranda Palms Ph 2a SubDv. ⋅ 34746 Zip Code

Situated in the sought-after Veranda Palms community, this fully furnished, professionally decorated 15-bedroom, 15.5-bath luxury vacation home offers 6,375 square feet of exceptional living and entertaining space and comfortably accommodates more than 30 guests. Whether you’re looking for a high-performing short-term rental, a multi-generational family retreat, or a luxury business getaway, this remarkable property delivers on every level. Each of the 15 bedrooms features its own private bathroom, offering guests exceptional comfort, privacy, and convenience. The open-concept layout includes a spacious large-group kitchen, multiple gathering areas, themed bedrooms, a classic movie-themed cinema room, and a Star Wars-inspired arcade and game room. Outside, enjoy a private pool and spa, a private lot backing to HOA greenspace, and an oversized driveway with ample parking for multiple vehicles. Established as a successful short-term rental with a strong rental history, the home is offered fully furnished and ready for continued rental use or personal enjoyment. Its turnkey condition, impressive amenities, and thoughtful design provide an excellent opportunity for continued income generation with the flexibility to enjoy the property yourself. Veranda Palms offers 24/7 gated security and an outstanding collection of resort-style amenities, including a community pool, jacuzzi, splash park, playground, waterslides, and state-of-the-art fitness center. Lawn maintenance is included in the HOA fee, and there are no CDD fees. Conveniently located just minutes from Walt Disney World, with easy access to Universal Orlando, shopping, dining, golf, entertainment, and Orlando International Airport, this exceptional property puts you in the heart of Central Florida’s world-renowned vacation market. A rare combination of size, amenities, privacy, and established rental performance, this is a property that truly stands apart. Schedule your private showing today!

2562 Shanti Drive, Kissimmee

3 Beds ⋅ 2 Baths ⋅ Blackstone Landing Ph 3 SubDv. ⋅ 34758 Zip Code

Welcome to 5551 Sycamore Canyon Drive! This spacious 3-bedroom, 2-bathroom home offers an inviting open floor plan with comfortable living spaces and thoughtful updates throughout. The primary suite features a convenient tub/shower combination, while the home also offers updated vinyl flooring and an updated re-pipe for added peace of mind. The house has newer roof (2021) and brand-new HVAC system to be installed prior to closing add even more value. Enjoy Florida living from the screened-in patio, overlooking a private setting with no rear neighbors. Located in the quiet Blackstone Landings community, residents have access to a neighborhood park and basketball court. Conveniently situated near schools, shopping, fitness, entertainment, Disney, and much more, this home offers a great combination of comfort, privacy, and location. Come see all that 5551 Sycamore Canyon Drive has and make it your next home!

5551 Sycamore Canyon Drive, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Trafalgar Village Ph 2 SubDv. ⋅ 34758 Zip Code

WELCOME HOME TO THIS BEAUTIFULLY MAINTAINED 4-BEDROOM, 4-BATHROOM HOME IN A GATED, GUARD-SECURED COMMUNITY, WHERE COMFORT, RESORT-STYLE LIVING, AND INVESTMENT POTENTIAL COME TOGETHER! This spacious home features an OPEN FLOOR PLAN designed for entertaining, relaxing, and enjoying time with family and friends. The impressive primary suite is truly a retreat, featuring double-door entry, generous space, a beautiful an-suite bathroom, and a walk-in closet. The upgrades make this home even more appealing: ROOF (2026), A/C (2022), TANKLESS WATER HEATER (2020), POOL EQUIPMENT (2021), TILE FLOORING (2021), APPLIANCES (2022), and AUTOMATIC SPRINKLER SYSTEM (2024). A WHOLE-HOUSE WATER SOFTENER provides added comfort, while the security cameras will remain with the property. The WASHER AND DRYER ARE ALSO INCLUDED. Step outside and enjoy your PRIVATE HEATED POOL AND SPA, perfect for Florida living year-round. The outdoor area also features a GAS BBQ, making it ideal for entertaining or simply enjoying a relaxing evening at home. The attached one-car garage and spacious driveway provide parking for up to three vehicles. Located in a desirable guard-gated community offering an impressive array of amenities, including a THEATER, GYM, LARGE COMMUNITY POOL, TRAILS, BOULEVARD, BASKETBALL COURTS, AND MORE. Whether you're looking for a full-time residence, a vacation home, or an investment property, this home offers exceptional flexibility with opportunities for BOTH SHORT-TERM AND LONG-TERM RENTALS, subject to community rules and applicable regulations. Enjoy the home during your holidays and generate rental income when you're away! This is the kind of property you need to EXPERIENCE IN PERSON to truly appreciate. Schedule your private showing today and come see everything this exceptional Florida home has to offer!

4978 Pall Mall Street W, Kissimmee

2 Beds ⋅ 2 Baths ⋅ Carlyle Residences South At Celebration Condo SubDv. ⋅ 34747 Zip Code

This NEWLY RENOVATED Carlyle Residences condo sits in the HEART OF CELEBRATION with restaurants, shopping and entertainment right outside of your door! Enter to find new VINYL PLANK FLOORING (2026), CEILING FANS (2026), LIGHT FIXTURES (2026) and FRESH PAINT (2026) throughout the home along with TALL CEILINGS and CROWN MOLDING. There are new QUARTZ COUNTERTOPS, sink and faucet (2026) in the eat-in kitchen which also has a spacious breakfast bar at the island, a closet pantry and a dinette. The OPEN FLOORPLAN is filled with natural light from the large windows and 2 sets of FRENCH DOORS that lead to the PRIVATE BALCONY overlooking Celebration Avenue! The FLEX SPACE will make a great 3rd bedroom, office, or home gym and has new French doors (2026) for privacy. The primary bedroom has a large WALK-IN CLOSET, spacious en-suite bathroom with double sinks, separate shower and garden tub. The 2nd bedroom is spacious with a walk-in closet. There is a laundry closet with a storage rack and appliances that convey. This condo includes a private 1-car GARAGE located conveniently at the stairs that lead to the condo. The garage was also recently painted and has an EPOXY FLOOR (2026). The building has an ELEVATOR for easy access. Celebration is a golf cart community, and the amenities include pools, playground, tennis courts, a dog park and so much more!

762 Celebration Avenue Unit 2201, Celebration

4 Beds ⋅ 4 Baths ⋅ Compass Bay Unit 4 SubDv. ⋅ 34746 Zip Code

FULLY FURNISHED, SHORT-TERM RENTAL READY & GATED – this 4-bedroom, 3.5-bath townhome in the sought-after Compass Bay community of Kissimmee offers everything you want in a vacation home, investment property or Central Florida getaway! Modern furnishings, THEMED BEDROOMS, upgraded lighting, DOUBLE-PANE WINDOWS with window treatments and a HYBRID ELECTRIC/HEAT PUMP WATER HEATER add comfort, efficiency and style. The tiled OPEN-CONCEPT MAIN FLOOR makes everyday living and entertaining easy, with a spacious living and dining area flowing into a well-appointed kitchen featuring STAINLESS STEEL APPLIANCES and a long BREAKFAST BAR with plenty of seating for casual meals. A convenient half bath off the foyer completes the first floor. All four bedrooms are upstairs, creating separation from the main living areas. The PRIMARY SUITE features its own full en-suite bath, while the SECOND BEDROOM is a JUNIOR SUITE setup with another private bath. Bedrooms three and four share a third full bathroom, and the UPSTAIRS LAUNDRY closet keeps it close to the bedrooms. Outside, enjoy the large PAVER PATIO with VINYL PRIVACY FENCING – an inviting space to relax after a long day at the parks and a COVERED FRONT PORCH that welcomes you home. Compass Bay delivers LOW-MAINTENANCE TOWNHOME LIVING in a GATED COMMUNITY with a COMMUNITY POOL and an excellent Kissimmee location. With easy access to Osceola Parkway, US-192/530, SR 535 and SR 417, you are just minutes from Central Florida’s THEME PARKS, RESORT AREAS, shopping, dining and entertainment. Whether you are looking for a fully furnished short term rental, vacation home or a place of your own near Orlando’s world-famous attractions, this Compass Bay townhome delivers the space, location and flexibility to make it happen. Call today for more information and schedule a tour!

5109 Killarney Way, Kissimmee

N/A SubDv. ⋅ 34758 Zip Code

THIS PROPERTY IS A FLAG LOT WITH GREAT POTENTIAL FOR YOUR FUTURE HOME OR AN INVESTMENT PROPERTY.MAKE YOUR MOVE BEFORE IT'S TAKEN.

Aurelia Ct, Kissimmee

5 Beds ⋅ 4 Baths ⋅ Storey Lake SubDv. ⋅ 34746 Zip Code

Pride of ownership shines throughout this upgraded turnkey 5-bedroom, 3.5-bath home with a first-floor primary suite in the gated resort community of Storey Lake. Lovingly maintained by its original owner and never rented, this nearly 4,000-square-foot residence is ready for you to move right in. Inside, rich hardwood and elegant tile flooring flow throughout, and the kitchen features beautiful granite countertops. The first-floor primary suite, finished with warm wood floors, offers privacy and convenience, while a separate dedicated office makes working from home easy. Upstairs, an expansive loft is ready to become a media room, game room, playroom, or second living area. Everyday living is easier with TWO laundry rooms, one on each floor, plus a security system for added peace of mind. Outside, enjoy a fully fenced backyard and screened patio, ideal for morning coffee or weekend barbecues. Best of all, a private gate in the fence opens right across from the clubhouse, putting the resort-style pool, fitness center, playgrounds, and dog park just steps away. A paver driveway, custom concrete curbing, and a sought-after 3-car garage complete the curb appeal. Living in Storey Lake feels like a vacation every day, just minutes from Central Florida's world-famous attractions, shopping, and dining. Homes this well-maintained don't come along often. Schedule your private showing today!

3074 White Horse Court, Kissimmee

3 Beds ⋅ 4 Baths ⋅ Charleston Place SubDv. ⋅ 34747 Zip Code

Virtually Staged. Welcome to Charleston Place in Celebration’s desirable North Village, where classic neighborhood charm meets beautifully updated interiors and an exceptional amount of living space. Offering more than 2,500 square feet across three levels, this impressive townhome features three generously sized bedrooms, each with its own private ensuite bath and walk-in closet, plus a convenient first-floor half bath. The home has undergone an extensive series of recent updates, creating a fresh, polished and beautifully cohesive interior. Walls, ceilings and doors have been completely repainted, with new blinds, ceiling fans and light fixtures throughout. Additional updates include new door handles, hinges and hardware, along with updated light switches and outlets. The open-concept main level offers spacious living and dining areas flowing naturally into the kitchen, where quartz countertops provide a clean, sophisticated finish. Beautiful porcelain wood-look plank flooring extends throughout the first floor, combining the warmth of wood with the durability of porcelain tile. A true highlight is the collection of recently remodeled bathrooms, beautifully finished with a luxurious contemporary aesthetic. Updates include designer vanities with quartz and marble tops, new showers and tubs, toilets, faucets, shower controls, mirrors and lighting, along with premium large-format porcelain tile on the walls and floors. The result is a series of stylish, spa-inspired spaces that feel fresh, refined and move-in ready. The second floor features two oversized bedrooms, each with a private ensuite bath and large walk-in closet. A conveniently located laundry closet is just steps away. The entire third floor is dedicated to an expansive, apartment-sized bedroom suite with its own full bath and walk-in closet. New luxury vinyl plank flooring enhances this private level, making it ideal for guests, extended family, a home office or anyone who appreciates additional privacy. Outside, a secluded garden courtyard surrounded by mature landscaping provides a peaceful setting for morning coffee, evening cocktails or simply enjoying Florida’s year-round outdoor lifestyle. A detached two-car garage offers excellent parking and storage. Additional improvements include an A/C replaced in 2021 and water heater replaced in 2024. And then there’s the Celebration lifestyle! North Village offers the inviting neighborhood atmosphere that makes Celebration such a distinctive place to call home. Residents enjoy community pools, parks, playgrounds and recreational amenities, along with picturesque paths, lakes and tree-lined streets perfect for walking and biking. Celebration Town Center is nearby, offering restaurants, cafés, boutiques and year-round community events. Walt Disney World and Central Florida’s world-famous attractions are just minutes away, while convenient access to I-4 connects you with Orlando, Tampa and surrounding communities. Orlando International Airport is approximately 30 minutes away, with Florida’s Atlantic and Gulf Coast beaches within easy reach. With more than 2,500 square feet, three private bedroom suites, extensive recent renovations, a two-car garage and a sought-after North Village location, this home delivers the space, style and lifestyle that make Celebration living so special.

319 Celebration Boulevard, Celebration

9 Beds ⋅ 10 Baths ⋅ Whitemarsh Cove SubDv. ⋅ 34747 Zip Code

Virtually Staged. LUXURY REUNION RESORT INVESTMENT ESTATE | 9 En Suite BEDROOMS | PRIVATE POOL & SPA | THEMED VACATION RENTAL OPPORTUNITY Welcome to 7626 Whitemarsh Way, an exceptional luxury vacation home located within the exclusive gated enclave of Whitemarsh Cove in Reunion Resort, the only community in Reunion with the option to purchase a very exclusive, very hard to obtain Golf Membership. Designed for both luxury living and high-performing short-term rental potential, this expansive 9-bedroom, 10-bathroom estate offers over-the-top accommodations for large families, corporate retreats, golf groups, and Disney vacationers seeking an elevated resort experience just minutes from Walt Disney World. Inside, guests are welcomed by a bright open-concept floor plan featuring expansive gathering spaces, a chef-inspired kitchen with oversized island, multiple entertainment areas, themed bunk rooms, and a dedicated game room designed to maximize guest enjoyment and rental appeal. With sleeping accommodations for 20+ guests, this property is ideally positioned to capitalize on Orlando's thriving vacation rental market. Step outside to your private resort-style oasis featuring a heated pool, spa, spacious lanai, and outdoor entertaining areas overlooking one of Florida's premier golf resort communities. Just moments away, enjoy access to Reunion Resort's world-class amenities and championship golf experiences. Spanning more than 2,300 acres, Reunion Resort offers an unmatched luxury lifestyle featuring three signature golf courses designed by Arnold Palmer, Jack Nicklaus, and Tom Watson, along with a water park, lazy river, waterslides, tennis courts, pickleball, fitness center, multiple dining venues, and year-round resort activities. Located just minutes from Walt Disney World, Universal Orlando, world-class shopping, dining, and entertainment, this property offers the perfect combination of luxury ownership, lifestyle, and investment opportunity. Guests and owners alike enjoy convenient access to Orlando's top attractions, including shuttle service to Disney. Whether you're seeking a luxury second home, a themed Airbnb investment property, a golf retreat, or a high-income-producing vacation rental, this exceptional Reunion Resort estate delivers the ultimate Central Florida resort lifestyle. Schedule your private showing today and discover why Reunion Resort continues to be one of Orlando's premier destinations for luxury living and vacation home investment. Home will come with an option to buy a Reunion Resort Membership. ** FOUNDERS CLUB Pricing subject to change, please inquire. **

7626 Whitemarsh Way, Reunion

3 Beds ⋅ 2 Baths ⋅ Wyndham Palms Condo Ph 2 SubDv. ⋅ 34747 Zip Code

Welcome to your fully furnished first-floor condo with 3 bedrooms and 2 bathrooms. (One bath is very large with a shared en suite entrance from a bedroom and a hall entrance. The other is entirely en suite with another bedroom). It is located in the desirable and centrally located Windsor Palms, 24-hour gated community in Kissimmee! This condo is in a prime location, positioned directly across the parking lot from the large clubhouse, providing exceptionally easy access to all the community’s many resort-style amenities, described below, without having to walk far. The first-floor location (no steps) provides level, easy walk-in accessibility from your vehicle. There is ample parking available throughout the community. Located just minutes from Magic Kingdom and conveniently close to Central Florida’s world-renowned theme parks, shopping, dining, and entertainment, this fully furnished condo offers the flexibility to serve as a vacation home, a turnkey short-term rental, or full-time residence. This fully furnished condo allows the new owner to enjoy the property or begin using it as a rental with minimal preparation. Windsor Palms offers an impressive selection of resort-style amenities designed for both relaxation and entertainment, including: a large resort-style swimming pool; hot tub; splash pad; tiki bar; movie theater; clubhouse; fitness center; business center; and picnic areas with BBQ grills. For those who enjoy an active lifestyle, the community also features basketball, tennis, and volleyball courts, providing plenty of options for recreation. The 24-hour manned gated entrance offers added security. Additional conveniences included with the property include: valet trash service; internet; water; cable; exterior building maintenance; including; roof repairs and replacements; and exterior painting. Whether you're looking for a vacation retreat, a turnkey investment property with short-term rental potential, or a place to call home, this furnished condo combines a prime location directly opposite the clubhouse, convenient access to multiple amenities, and an ideal location near Central Florida’s world-famous attractions. Don't miss the opportunity to own a piece of Central Florida in one of Kissimmee's sought-after vacation communities. Be sure to check out the virtual tour video for a closer look at the property and community.

2305 Butterfly Palm Way Unit 102, Kissimmee

4 Beds ⋅ 2 Baths ⋅ Eagle Bay Ph 1 SubDv. ⋅ 34743 Zip Code

Welcome to this spacious 4-bedroom, 2-bath home situated on a desirable CORNER LOT in the Eagle Bay community of Kissimmee! Offering approximately 1,874 sq. ft. of living space, this home features a functional layout with a living/dining room combination and a kitchen/family room combination, providing comfortable spaces for everyday living and entertaining. The kitchen features an eat-in area and generous workspace, and all kitchen appliances are included, along with the washer and dryer. Vaulted ceilings enhance the open feel of the main living areas. The primary suite features a private bath with dual sinks, a garden tub, and a separate shower. Step outside to the screened lanai and fenced patio, an inviting space to relax and enjoy Florida living. Additional highlights include a ROOF REPLACED IN 2025, a 2-car garage, and the additional outdoor space provided by this corner lot. LOW HOA of approximately $37 monthly, with community amenities including a swimming pool, playground, basketball court, and volleyball area. Location is another highlight! Enjoy convenient access to supermarkets, shopping, dining, and everyday essentials, as well as Simpson Road and Osceola Parkway, providing convenient connections to Florida’s Turnpike and SR-417 (Central Florida GreeneWay). The property is also conveniently positioned for access to Lake Nona Medical City, Orlando International Airport, and the greater Orlando area. Schedule your private showing and discover this Eagle Bay home today!

2580 Hunley Loop, Kissimmee

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