Kissimmee Homes with Maintenance Amenities

Kissimmee Homes with Maintenance Amenities

Welcome to Kissimmee, Florida – a vibrant city nestled in the heart of Osceola County, where sunshine and charm meet to create the perfect backdrop for your dream home. Known for its close proximity to world-renowned attractions like Walt Disney World and Universal Studios, Kissimmee offers an unparalleled lifestyle that combines adventure, relaxation, and a strong sense of community.

The real estate market in Kissimmee is diverse, catering to a variety of lifestyles and preferences. From cozy single-family homes to spacious townhouses, there is something for everyone in this enchanting region. Many homes in Kissimmee come equipped with maintenance amenities, ensuring that you can enjoy a worry-free lifestyle. Imagine having access to well-maintained pools, lush landscaping, and community recreational facilities without the hassle of upkeep. These amenities not only enhance your living experience but also foster a sense of community among residents.

Kissimmee is not just about attractions and beautiful homes; it boasts an array of parks, lakes, and outdoor activities that invite you to explore the natural beauty of Florida. With its warm climate, you can enjoy year-round outdoor fun, whether it’s fishing, hiking, or simply soaking up the sun on a lazy afternoon.

As you consider your next move, Kissimmee stands out as a place where comfort meets convenience. With its rich culture, family-friendly activities, and stunning homes with maintenance amenities, this charming city is ready to welcome you home. Discover the magic of Kissimmee today!

Newest Kissimmee Homes with Maintenance Amenities

1827 Southfork Drive, Kissimmee
$396,999
3 Beds ⋅ 2 Baths ⋅ Kindred Ph 3a SubDv. ⋅ 34744 Zip Code
Welcome to this stunning fully upgraded D.R. Horton Allex model, ideally positioned in a picturesque lakefront setting with an extended covered and screened lanai, within the highly desirable Kindred community. Built in 2023, this stylish three-bedroom, two-bathroom home offers modern design, an open split-bedroom floor plan and beautiful water views. The impressive kitchen is the heart of the home, featuring a gorgeous oversized quartz countertop and island with comfortable seating for four, a modern, large, farmhouse-style sink, touchless faucet, stainless steel appliances, abundant cabinetry and a spacious walk-in pantry. Gorgeous chandeliers and updated farmhouse-inspired lighting add warmth, elegance and character throughout the home. The private primary suite features an upgraded ensuite bathroom and a newly installed walk-in closet, giving the suite two walk-in closets and exceptional storage. Both bathrooms have been tastefully upgraded, while two additional bedrooms and the guest bathroom are conveniently positioned away from the master for ultimate privacy. A must see, must have turn key home, beautifully crafted exterior designed for peace, tranquility and luxurious living.

1827 Southfork Drive, Kissimmee
3113 Via Otero Drive, Kissimmee
$299,900
3 Beds ⋅ 3 Baths ⋅ Villa Sol Twnhms Village 6 SubDv. ⋅ 34744 Zip Code
Virtually Staged. NOW UNDER $300K in gated Villa Sol! Built in 2018, this spacious 3-bedroom, 2.5-bath townhome offers 1,584 sq. ft., a 2-car garage, private courtyard, and short-term rental flexibility all in a resort-style community near Lake Nona, Orlando International Airport, and Central Florida attractions. Step inside to an open-concept main level with luxury vinyl wood flooring connecting the kitchen, dining, and living areas. The kitchen features granite countertops, a 2024 Bespoke refrigerator and dishwasher, range, microwave, water softener, and reverse-osmosis filtration system. French doors open to a private brick-paver courtyard, creating a great space for outdoor dining, relaxing, or entertaining. The courtyard also provides direct access to the garage. All three bedrooms are located upstairs, along with the laundry area for added convenience. Villa Sol offers a long list of amenities, including a clubhouse, fitness center, resort-style pool and hot tub, hiking trails, basketball and tennis courts, playground, and access to East Lake Tohopekaliga and the Kissimmee Chain of Lakes through Boggy Creek. The HOA also includes cable, internet, and landscaping. The community is conveniently located near shopping, dining, major roadways, Lake Nona Medical City, Orlando International Airport, Disney, and Universal. Villa Sol is short-term rental approved in Osceola County, providing flexibility for buyers seeking a primary residence, second home, or investment property, subject to HOA rules and county requirements. The home may also be sold furnished, with the exception of one bedroom, subject to acceptable terms. If you have been waiting for a newer Villa Sol townhome with a 2-car garage, private courtyard, resort amenities, and a price under $300K, this one deserves a closer look. Schedule your private showing today.

3113 Via Otero Drive, Kissimmee
2756 Summer Retreat Lane, Kissimmee
$310,000
3 Beds ⋅ 2 Baths ⋅ Tohoqua Ph 5b SubDv. ⋅ 34744 Zip Code
Virtually Staged. Welcome to 2756 Summer Retreat, where comfort meets charm in one of Central Florida's most desirable 55+ communities. This beautifully upgraded home offers 2 bedrooms, 2 full bathrooms, and a versatile flex room that can easily serve as a third bedroom, home office, or den. Built in 2024, this inviting residence welcomes you with attractive curb appeal, a beautifully maintained yard, and a warm entrance. Inside, you'll find a bright open-concept floor plan filled with natural light, creating the perfect space for both everyday living and entertaining. The stylish kitchen features upgraded high cabinetry, a designer backsplash, and modern finishes that blend functionality with elegance. Thoughtful upgrades throughout the home include easy-to-maintain LVP flooring in the main living areas, unique ceiling fans in every room, outdoor lighting, and a covered patio designed for year-round enjoyment. A transferable pest control plan is also available for added peace of mind. The spacious primary suite features a large walk-in closet and an upgraded bathroom with a built-in shower bench. Secondary bedrooms are generously sized and offer ample storage. Every detail has been carefully selected to create a home that is both beautiful and practical. Residents enjoy access to exceptional community amenities, including a resort-style pool, tennis courts, dog park, clubhouse, and state-of-the-art fitness center. Conveniently located near historic Downtown Kissimmee, Florida's Turnpike, Walt Disney World, and Orlando International Airport, this home offers easy access to shopping, dining, entertainment, and major attractions. Don't miss this incredible opportunity to enjoy comfort, convenience, and an active lifestyle in a vibrant community. Schedule your private showing today!

2756 Summer Retreat Lane, Kissimmee
1534 Oak Reserve Drive, Kissimmee
$420,000
4 Beds ⋅ 2 Baths ⋅ Kindred Ph 2c & 2d SubDv. ⋅ 34744 Zip Code
Set in the heart of Kissimmee, 1534 Oak Reserve Dr keeps shopping, restaurants, theme parks, the airport, and major roads all within easy reach. This new listing pairs a connected address with a bright, move-in ready interior built for comfortable Florida living. Inside, 1,846 square feet of open, welcoming space await. High ceilings lend each room an airy feel, while the open floor plan links the main living areas for smooth, natural flow. Hard flooring runs through the shared spaces for effortless upkeep, and cozy carpet warms every bedroom, adding a soft, restful touch where it counts. At the center of the home, the kitchen shines with granite countertops and stainless steel appliances, making everyday cooking and casual entertaining simple. A smart split floor plan tucks the primary bedroom away for added privacy, creating a peaceful retreat at day's end. Three additional bedrooms flex easily for family, guests, or a home office, and the seller has added custom closets in the kids'rooms for extra storage. Two full bathrooms keep busy mornings running smoothly. Out back, a screened-in porch invites you to sip morning coffee or unwind in the shade, while a fully fenced yard offers privacy and room to play, garden, or gather. Residents also enjoy community perks like multiple pools and parks. With its handy location, thoughtful layout, and move-in ready condition, this Kissimmee charmer checks every box. Schedule your private showing today and see it for yourself.

1534 Oak Reserve Drive, Kissimmee
2925 Siesta View Drive, Kissimmee
$465,000
4 Beds ⋅ 3 Baths ⋅ Villa Sol Village 02 SubDv. ⋅ 34744 Zip Code
Welcome to the former Model Home, the only one like this in the entire community. HOA PAID TILL 2027. Discover the perfect blend of comfort & convenience in this spacious 4-bedroom, 3-full-bathroom home. With 2 generous living spaces designed for both everyday living & entertaining. This home offers flexibility for growing families, multi-generational living, or hosting guests. Full kitchen appliances, a fire place, window treatments, plantation shutters, tiled floors, granite countertops, light fixtures and barn doors. The home sits on a premium cul de sac lot with no rear neighbors. Enjoy the view from your expansive 10 x 24 screen in Florida room. Many extras added. Great air b & b, short term rental allowed. This gated community offers all you need, pool, fitness center, tennis & basketball courts. Your HOA includes internet, cable and lawn care. Kissimmee delivers an unbeatable Central Florida lifestyle: you’re just minutes from Walt Disney World & Central Florida’s top attractions, with easy access to shopping, dining, and Lake Tohopekaliga for outdoor recreation. Whether you’re drawn by the theme parks, the warm year-round climate, or the strong sense of community, this location puts it all within reach. 24 hour appointment only please no showings allowed Sunday, Monday or Thursday.

2925 Siesta View Drive, Kissimmee
26 Las Palmas Way Unit 1, Kissimmee
$224,999
2 Beds ⋅ 2 Baths ⋅ Las Palmas Villas SubDv. ⋅ 34743 Zip Code
Discover this well-maintained 2-bedroom, 2-bathdroom block-construction villa offering 960 sq ft of bright, single-level living on a 0.04acre corner lot with a BRAND-NEW roof just installed in 2026! Enjoy a private covered & enclosed rear porch perfect for morning coffee, sliding doors to the patio, and low maintenance living with community pool and sidewalks. With paved asphalt streets and assigned parking, and a prime Kissimmee location minutes to shopping, dining, schools & 192, this move -in ready home is perfect for first time buyers, investors, or those seeking Florida convenience. . Don't miss this incredible opportunity schedule your private showing today!

26 Las Palmas Way Unit 1, Kissimmee
1876 Cassidy Knoll Drive, Kissimmee
$495,000
5 Beds ⋅ 4 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code
Stunning Corner Lot Home with Exceptional Value! Don’t miss this incredible opportunity to own this spacious 5-bedroom, 3.5-bathroom home, priced below appraised value and offering up to $15,000 toward the buyer’s closing costs or rate buy-down. Designed with both comfort and functionality in mind, this beautiful home features a first-floor primary suite, providing privacy and convenience. The main level also includes a versatile flex room/den, perfect for a home office, playroom, study, or guest space. Upstairs, you’ll find a generous loft, ideal as a second living area, media room, game room, or entertainment space giving everyone room to relax and enjoy. Situated on a desirable corner lot, the property boasts a huge, fully fenced backyard with durable vinyl fencing, offering plenty of space for outdoor entertaining, pets, family gatherings, or even a future pool. With its spacious layout, premium corner location, oversized backyard, and outstanding buyer incentives, this home is an exceptional value that you won’t want to miss. Ask about available lender incentives toward buyer closing costs through select loan programs. Subject to lender approval and borrower qualification. Schedule your private showing today!

1876 Cassidy Knoll Drive, Kissimmee
3028 Camino Real Drive S, Kissimmee
$439,995
4 Beds ⋅ 2 Baths ⋅ Villa Sol Ph 02 Village 03 SubDv. ⋅ 34744 Zip Code
WELCOME TO 3028 CAMINO REAL DR S – YOUR PRIVATE POOL HOME IN THE UPSCALE GATED COMMUNITY OF VILLA SOL! Welcome to this beautiful pool home offering the perfect blend of comfort, privacy, and resort-style living in one of Kissimmee's most desirable communities. Whether you're searching for your primary residence, a vacation home, or an investment opportunity, this move-in-ready property checks all the boxes. Step inside to a spacious, open-concept floor plan filled with natural light, featuring generous living and dining areas that are perfect for everyday living and entertaining. The well-appointed kitchen offers ample cabinet and counter space and overlooks the main living area, making it ideal for gatherings. The spacious primary suite serves as a private retreat with a walk-in closet and en-suite bathroom, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your private screened-in pool, where you can relax, entertain, or enjoy Florida's year-round sunshine in your own backyard oasis. Located in the highly sought-after Villa Sol gated community, residents enjoy resort-style amenities including a clubhouse, community pool, fitness center, tennis courts, playground, walking trails, and beautifully maintained grounds. Conveniently located just minutes from Lake Nona Medical City, Orlando International Airport, SR-417, Florida's Turnpike, shopping, dining, golf courses, and world-famous attractions including Walt Disney World, Universal Orlando, and SeaWorld. Don't miss this incredible opportunity to own a private pool home in an unbeatable location. Schedule your private showing today before it's gone!

3028 Camino Real Drive S, Kissimmee
2705 Emerald Lake Ct Unit 2705, Kissimmee
$240,000
2 Beds ⋅ 2 Baths ⋅ Villas Of Emerald Lake Condo Ph 4 SubDv. ⋅ 34744 Zip Code
Virtually Staged. Welcome to Villas of Emerald Lake, where peaceful waterfront living meets everyday convenience. This beautifully updated first floor condo offers 2 bedrooms, 2 bathrooms, 1,240 square feet of comfortable living space, and a setting that's hard to find. Inside, you'll love the remodeled kitchen featuring quartz countertops, updated lighting, and wood-look tile throughout the main living areas. A wet bar, inside laundry closet, and detached one-car garage with an automatic opener add everyday convenience. The living room opens to a screened patio overlooking Fish Lake and your private dock, creating the perfect place to enjoy your morning coffee or unwind at the end of the day. The spacious primary suite features a walk-in closet with a window overlooking the lake and an en suite bathroom with a relaxing garden tub. Residents also enjoy a community pool, mature oak trees, and beautifully maintained grounds. Tucked away on a quiet street just off Highway 192, this hidden gem is ideally located on the border of St. Cloud and Kissimmee, less than five minutes from shopping, dining, medical facilities, and the Florida Turnpike. You'll also enjoy easy access to Downtown St. Cloud, Downtown Kissimmee, Orlando International Airport, and the Brightline station. If you've been looking for a move-in-ready home that offers low-maintenance living, peaceful water views, and an unbeatable location, this is one you won't want to miss.

2705 Emerald Lake Ct Unit 2705, Kissimmee
2024 Cypress Bay Boulevard, Kissimmee
$293,999
3 Beds ⋅ 3 Baths ⋅ Cypress Lakes Twnhms Ph 2 Unit 1 SubDv. ⋅ 34743 Zip Code
Welcome to this spacious and well-maintained 3-bedroom, 2.5-bath townhome located in the gated Cypress Lakes community in Kissimmee. Offering over 1,800 square feet of living space, this home features a functional and comfortable layout with updated flooring, neutral tones, and plenty of natural light throughout. The kitchen is equipped with stainless steel appliances, ample cabinet space, and a convenient breakfast bar that opens to the living and dining areas, making it perfect for both everyday living and entertaining. One of the highlights of this home is the primary bedroom and bathroom conveniently located on the first floor, providing privacy and easy access. Upstairs you will find two additional bedrooms, a full bathroom, and a spacious loft area that works perfectly as a second living room, entertainment space, home office, or play area. This property also includes a garage and assigned parking, and residents enjoy the benefits of living in a gated community with access to a community pool and well-maintained grounds. Ideally located near shopping, restaurants, schools, major highways, and just a short drive to Disney and other Central Florida attractions, this home offers comfort, security, and convenience.

2024 Cypress Bay Boulevard, Kissimmee
3204 Tidewater Drive, Kissimmee
$240,000
2 Beds ⋅ 2 Baths ⋅ Raintree Park Ph 1 SubDv. ⋅ 34743 Zip Code
An updated kitchen, extra space and everything on one level. This single-story, 2-bedroom, 2-bath townhome at 3204 Tidewater Drive combines an updated interior with easy everyday living in Raintree Park. The spacious, fully renovated kitchen features modern finishes, a practical layout and an oversized counter with plenty of room for meal preparation and serving. Updated flooring throughout means no carpet to maintain, while an HVAC system replaced less than a year ago adds to the home’s recent improvements. A professionally enclosed rear porch with its own A/C vent provides additional usable space for a reading retreat, hobby area or a comfortable place to unwind. Positioned near the community entrance and a short walk from the pool, the home makes it easy to enjoy the neighborhood’s conveniences. HOA-covered exterior maintenance helps reduce upkeep responsibilities, leaving more time to enjoy your home. Whether you’re purchasing your first home, downsizing or exploring an investment opportunity, this townhome offers a practical combination of updates, flexible space and single-level comfort.

3204 Tidewater Drive, Kissimmee
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