Kissimmee Homes with Sidewalk Exterior Features

Kissimmee Homes with Sidewalk Exterior Features

Welcome to Kissimmee, Florida—a vibrant city where sunshine meets charm! Nestled just south of the bustling Orlando, Kissimmee is a delightful blend of natural beauty, rich history, and modern convenience. Known for its proximity to world-famous attractions like Walt Disney World and Universal Studios, Kissimmee offers an exciting lifestyle that appeals to residents and visitors alike.

As you explore this enchanting city, you’ll discover a variety of neighborhoods, each with its unique character and appeal. One of the standout features of many homes in Kissimmee is their inviting sidewalk exterior. These charming walkways not only enhance the aesthetic appeal of the community but also promote a friendly atmosphere where neighbors can connect. Imagine taking leisurely strolls in the evening, with the warm Florida breeze gently rustling the leaves as you greet fellow residents.

The homes in Kissimmee are designed for modern living, often featuring spacious layouts, contemporary finishes, and outdoor spaces perfect for entertaining. Whether you’re seeking a cozy family home or a luxurious retreat, you’ll find properties that cater to every lifestyle. The sidewalks encourage an active lifestyle, making it easy to enjoy morning jogs or evening walks with loved ones.

Kissimmee is more than just a place to live; it’s a community that embraces the joys of life. With its ideal location, friendly neighborhoods, and beautiful homes with sidewalk features, Kissimmee invites you to create lasting memories in the heart of Florida. Come discover your dream home in this enchanting city!

Newest Kissimmee Homes with Sidewalk Exterior Features

$474,900
4 Beds ⋅ 3 Baths ⋅ Cypress Hammock Ph 2 SubDv. ⋅ 34746 Zip Code
Welcome to 1466 Woodmont Boulevard, a beautifully upgraded two-story home in the Cypress Hammock master-planned community in Kissimmee, FL. Built in 2024, this homes sits on a pond view lot with a stunning view and has 4-bedroom, 2.5-bath and a 2-car garage. The open first floor pairs a combined living and dining area in large ceramic tile with a kitchen featuring granite counters, shaker cabinetry, subway tile backsplash, stainless appliances, walk-in pantry and an island that sits up to four people. A dedicated home office sits just off the main living space, finished with custom built-in desks, cabinetry, and designer accent walls, an ideal setup for remote work. There's also a conveniently located half bath that serves the first floor. Sliding doors open to the covered lanai and fenced yard overlooking the water. Upstairs, a spacious bonus loft opens at the top of the stairs and works beautifully as a media room, playroom, or second gathering space. The primary suite offers luxury vinyl plank (LVP) flooring, an en-suite bath with a dual-sink granite vanity, and a professionally built-in, walk-in closet complete with custom shelving, drawers, and integrated lighting. Three more bedrooms with an additional bathroom complete the second floor. Additional features include a covered rear lanai, a fully fenced backyard with black aluminum picket fencing along the water to keep the view open, a paver driveway, and an interior laundry room with washer and dryer included. Cypress Hammock residents enjoy resort-style amenities including a community pool with water slide, playground, pavilion, and a dock overlooking the lake. All backed by a low monthly HOA and NO CDD. Easy access to Poinciana Boulevard and US-192 puts supermarkets, everyday shopping, and a wide range of restaurants within minutes, including the dining and shopping options of the Old Town entertainment district. Walt Disney World is approximately 9 miles away, with Orlando International Airport about 20 miles east. Don't miss out and schedule your showing today!

1466 Woodmont Boulevard, Kissimmee
$875,000
4 Beds ⋅ 4 Baths ⋅ Celebration Area 5 SubDv. ⋅ 34747 Zip Code
First floor primary bedroom plus upstairs ensuite in desirable Artisan Park. This charming 4-bedroom, 3.5-bath Coastal-style with 2,587 square feet of living space, this home features double front porches and a floor plan designed for comfortable everyday living. The primary suite is conveniently located downstairs, while three additional bedrooms are upstairs, including one with a private bathroom. As you enter the home, you're greeted by a separate dining room and living room, creating a welcoming and traditional entry space. As you continue toward the back of the home, the layout opens into the kitchen and family room, creating a comfortable gathering space for everyday living. The backyard patio provides a great spot for outdoor dining and entertaining, or simply relaxing and enjoying the Florida weather. The home also features fully owned solar panels and a new roof was installed in 2022. Residents of Artisan Park have exclusive access to the private clubhouse, featuring a restaurant and bar, fitness center, and resort-style pool, along with a variety of social events held throughout the month.

1114 Tapestry Drive, Celebration
$290,000
2 Beds ⋅ 2 Baths ⋅ Pebble Creek SubDv. ⋅ 34744 Zip Code
Welcome to 1374 Boulder Dr, a well-maintained 2-bedroom, 2-bath home offering 1,063 sq. ft. of comfortable living space in the desirable Pebble Creek area of Kissimmee. Whether you are a first-time homebuyer looking for an affordable place to call home or an investor searching for a great opportunity in a convenient Central Florida location, this property offers excellent potential. Built in 1984 with continuous footing construction, the home features a 2024 HVAC system, 2017 roof, and 2017 water heater. Its ready to move in, minimalist style provides a blank canvas ready for you to personalize and make your own. Best of all NO HOA and NO CDD! Enjoy an excellent location just approximately 5 minutes from Walmart near Osceola Parkway and Michigan Avenue, Florida’s Turnpike, and Valencia College, with convenient access to shopping, dining, schools, and major roadways. A great combination of location, affordability, flexibility, and investment potential. schedule your showing today!

1374 Boulder Drive, Kissimmee
$450,000
4 Beds ⋅ 3 Baths ⋅ Lindfields Unit 4 SubDv. ⋅ 34747 Zip Code
Welcome to 2791 Picadilly Circle, Kissimmee, FL — a beautifully updated 4-bedroom, 2.5-bath pool home offering the perfect combination of modern upgrades, generous living space, privacy, and the Florida lifestyle. From the moment you step inside, you’ll appreciate the bright, open floor plan and thoughtfully upgraded interior. At the heart of the home is the updated gourmet kitchen, designed to impress with stylish finishes and an inviting layout perfect for everything from everyday meals to entertaining family and friends. The bathrooms have also been tastefully updated and upgraded, giving the home a fresh, modern feel throughout. With four spacious bedrooms and 2.5 baths, there’s plenty of room to spread out. The versatile living areas provide flexibility for entertaining, working from home, family gatherings, or simply relaxing at the end of the day. Step outside and discover your own private Florida retreat. The fully fenced backyard features a sparkling swimming pool and plenty of space to relax, entertain, barbecue, or soak up the Florida sunshine. Whether hosting weekend gatherings or enjoying a quiet afternoon poolside, this outdoor space is designed to be enjoyed year-round. Conveniently located in the heart of Kissimmee, 2791 Picadilly Circle puts you just minutes from shopping, dining, schools, major roadways, Orlando-area attractions, and everything Central Florida has to offer. Updated gourmet kitchen. Upgraded bathrooms. Four spacious bedrooms. Private fenced backyard. Sparkling pool. Prime Kissimmee location. This home checks all the boxes and is ready for its next owner. Schedule your private showing today and experience everything 2791 Picadilly Circle has to offer!

2791 Picadilly Circle, Kissimmee
$724,900
6 Beds ⋅ 9 Baths ⋅ Bellavida Ph 2c SubDv. ⋅ 34746 Zip Code
Experience resort-style living in this massive pool home, perfect for large families or short-term guests. The chef’s kitchen is built for entertaining, boasting an oversized stone island, dual refrigerators, and dual dishwashers. Melt into the open-concept layout that flows straight out to your private, screened pool deck. With dual primary suites (one on each floor) and a massive upstairs loft, everyone gets their own space. Enjoy 24/7 guard-gated security, premium community amenities, and a prime location minutes from Disney, championship golf, and top Central Florida dining.

222 Marcello Boulevard, Kissimmee
$299,900
4 Beds ⋅ 2 Baths ⋅ Peppertree At Cyp Wds U1 SubDv. ⋅ 34758 Zip Code
Short Sale. This exceptional 4-bedroom, 2-bathroom single-story home is in pristine, move-in ready condition, offering effortless, stairs-free living paired with the convenience of an attached 2-car garage. The interior is dramatically highlighted by striking cathedral and vaulted ceilings that enhance the natural light and create an open, expansive atmosphere throughout the living spaces. At the heart of the home, the impressive kitchen comes fully outfitted with elegant granite countertops and a sleek suite of stainless steel appliances, offering a stylish, high-performing hub for all your daily culinary and entertaining needs. Spotlessly prepared and meticulously maintained from top to bottom, this turnkey residence is completely ready for a stress-free transition into a comfortable lifestyle.

414 Spice Court, Kissimmee
$648,800
5 Beds ⋅ 5 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
Welcome to this exceptional home in Solara Resort. This is a rare opportunity! Although located in one of Orlando’s most sought-after short-term rental communities, this home has never been used as a vacation rental. It has had only one owner and has been enjoyed exclusively by the same family since it was built. The home has been very well cared for and remains in outstanding condition. The first floor features a large suite, perfect for the owners or guests. Upstairs, there is a loft that can be used as a media room, game room, or family lounge, plus another spacious suite and three additional bedrooms. Two of the bedrooms share a convenient Jack and Jill bathroom. Offered fully furnished and move-in ready, this home is located just minutes from Walt Disney World, Universal Orlando, shopping, dining, and entertainment. Solara Resort offers great amenities including a clubhouse, resort-style pool, splash park, FlowRider® surf simulator, fitness center, sports courts, playgrounds, restaurant, café, and 24-hour gated security. Perfect as a primary residence, vacation home, or investment property with excellent short-term rental potential.

9083 Sunshine Ridge Loop, Kissimmee
$265,000
4 Beds ⋅ 3 Baths ⋅ Club Cortile SubDv. ⋅ 34746 Zip Code
Welcome to this newly renovated 4-bedroom, 3-bathroom townhome located in the desirable Club Cortile gated community in the heart of Kissimmee. This move-in-ready property features brand-new flooring, fresh interior paint, a new microwave, and a new dishwasher, creating a clean and updated living space. The open-concept floor plan seamlessly connects the living, dining, and kitchen areas, providing plenty of natural light and functional living space. The kitchen features ample cabinetry, generous countertop space, and modern appliances for everyday convenience. The thoughtfully designed layout includes four spacious bedrooms and three full bathrooms, providing flexibility for family living, guests, or a home office. The primary suite includes a private en-suite bathroom and generous closet space. Step outside to the private screened lanai, providing a comfortable outdoor space for relaxing or entertaining. Residents of Club Cortile enjoy access to community amenities including a gated entrance, clubhouse, resort-style swimming pool and spa, fitness center, tennis courts, basketball court, playground, and beautifully maintained common areas. Conveniently located just minutes from Walt Disney World, Universal Orlando, SeaWorld, shopping, dining, golf courses, and major roadways including US-192, Osceola Parkway, SR 417, and Florida's Turnpike, this home provides convenient access to Central Florida's attractions and everyday amenities.

2848 Club Cortile Circle, Kissimmee
$470,000
4 Beds ⋅ 2 Baths ⋅ Oaks Ph 1 B2 SubDv. ⋅ 34746 Zip Code
2111 Eagleview Ct, Kissimmee, FL 34746 The Oaks – Golf & Lake Community Welcome home to this beautifully maintained 4-bedroom, 2-bath pool home nestled on a quiet cul-de-sac in the sought-after Oaks golf community. Enjoy front-row views of the 9th tee box along with a peaceful water and nature backdrop right from your screened lanai. Inside, soaring 10'6" ceilings and 18x18 tile set the stage in the open kitchen/family room combo, while separate formal living and dining rooms add versatility for entertaining. The well-appointed kitchen features a closet pantry, breakfast bar, crown-molded cabinetry, and stainless steel appliances. The thoughtful 3-way split floor plan places all four bedrooms for maximum privacy, and the spacious primary suite offers a large walk-in closet, dual sinks, garden tub, and separate shower. Step outside to your private, heated in-ground pool with screen enclosure and child safety fence — the perfect spot to soak up the Florida sunshine. A 2-car garage with drop-down attic stairs adds extra storage. Additional highlights: NEW ROOF (2024), newer water heater, rounded corners, chair rail, decorative columns, and lighted display niche. The Oaks offers resort-style amenities including an 18-hole championship golf course winding through century-old oaks, tennis and basketball courts, a playground, and community lake access with a boat ramp and lift on Lake Toho — plus RV/boat storage available for a fee. Conveniently located near shopping, dining, top schools, medical facilities, theme parks, and the airport. Don't miss this rare opportunity to enjoy the Florida lifestyle in a premier golf and lake community! Beds: 4 | Baths: 2 | Heated SF: 2,109 | Total SF: 2,925 | Year Built: 2005 | Lot: 0.18 acres | Garage: 2-car attached | Pool: Private, heated, screened | HOA: $288/yr | CDD: $543/yr | Flood Zone: X

2111 Eagleview Court, Kissimmee
$345,000
2 Beds ⋅ 2 Baths ⋅ Four Seasons At Orlando Pb 3b & 4a SubDv. ⋅ 34747 Zip Code
Experience resort-style Florida living in this beautifully upgraded 2-bedroom, 2-bath home located in the highly desirable Four Seasons 55+ guard-gated community in Kissimmee. Move-in ready and thoughtfully enhanced throughout, this home combines stylish upgrades, excellent storage, comfortable living spaces, and an exceptional amenity-filled lifestyle. Inside, you'll find upgraded flooring extending through the living areas, bedroom and closets, along with beautiful French doors, window blinds and draperies, upgraded ceiling fans and lighting throughout, and an elegant upgraded dining room light fixture. The kitchen features a stylish backsplash, additional cabinetry and cupboards, an added bank of drawers for convenient storage, decorative cabinet and drawer pulls, and an exhaust fan over the stove. These thoughtful additions provide both functionality and an attractive finished look. The laundry room offers additional cabinetry and storage, decorative hardware, a coordinating backsplash and plumbing already in place for a laundry sink. Both bathrooms feature attractive finishes, including a guest shower and an upgraded beveled-edge finish in the primary shower. Enjoy Florida's beautiful weather from the screened-in lanai, creating an inviting additional space for morning coffee, relaxing, entertaining family and friends, or simply enjoying the Florida lifestyle. Additional improvements include gutters and upgraded garage shelving, providing even more convenient storage and organization. And the lifestyle doesn't stop at your front door. Four Seasons offers an outstanding resort-style 55+ lifestyle within a guard-gated community, complete with an impressive clubhouse offering a wide variety of activities and social opportunities, oversized swimming pools, fitness center, pickleball courts, tennis courts, golf, and much more. Whether you enjoy staying active, playing golf, relaxing poolside, participating in community activities, or spending time with friends at the clubhouse, Four Seasons offers something for virtually every lifestyle. With extensive upgrades already completed, generous living and storage space, outstanding community amenities, and a desirable Kissimmee location, this home offers the opportunity to simply move in and start enjoying everything Central Florida has to enjoy. This is more than a home—it's the Florida lifestyle you've been looking for. Schedule your private showing today and experience Four Seasons for yourself!

1667 Key Bay Trail, Kissimmee
$400,000
3 Beds ⋅ 3 Baths ⋅ Soleil At Westside SubDv. ⋅ 34747 Zip Code
Short Sale. Welcome to Soleil at Westside! This beautiful two-story home features a spacious open-concept floor plan, ideal for modern living and entertaining. The property offers 4 bedrooms, 2.5 bathrooms, a well-appointed kitchen with solid surface countertops, and a bright living area. Located in a resort-style gated community with top-tier amenities including a community pool, clubhouse, fitness center, playground, and park. Conveniently situated near major highways, dining, shopping, and Orlando's world-famous attractions. POTENTIAL SHORT SALE: Sale of this property is subject to third-party approval by the seller's mortgage lender(s).

1090 Boardwalk Place, Kissimmee
$330,000
4 Beds ⋅ 3 Baths ⋅ West Lucaya Village SubDv. ⋅ 34747 Zip Code
Beautiful fully furnished 4-bedroom, 3-bathroom townhome located in the highly sought-after gated community of West Lucaya Village. This spacious two-story home features an open-concept floor plan, a modern kitchen with ample cabinet and counter space, and comfortable living and dining areas designed for family living or vacation stays. The primary suite includes a walk-in closet and private bathroom, while the additional bedrooms provide plenty of space for family and guests. West Lucaya Village offers outstanding resort-style amenities, including a clubhouse, community pool, fitness center, playground, and beautifully maintained grounds. Ideally located just minutes from Walt Disney World, major attractions, shopping, restaurants, and Orlando's main highways. Zoned for short-term rentals, this property is an excellent opportunity as a primary residence, vacation home, or income-producing investment. Move-in ready and being sold fully furnished.

3200 Cupid Place, Kissimmee
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