Kissimmee Homes with Pool Amenities

Kissimmee Homes with Pool Amenities

Welcome to Kissimmee, Florida – a vibrant city nestled in the heart of Osceola County, just a stone's throw away from the enchanting attractions of Orlando. Known for its warm climate and welcoming community, Kissimmee is the perfect blend of suburban charm and urban excitement. With its rich history, diverse culture, and an array of recreational activities, this area is not just a place to live, but a lifestyle to embrace.

One of the standout features of Kissimmee is its impressive selection of homes with pool amenities. Imagine coming home to your very own oasis, where you can unwind in the sparkling waters of your private pool after a long day. These homes are designed with relaxation and enjoyment in mind, offering spacious backyards perfect for entertaining friends and family or simply soaking up the Florida sun. Whether you’re looking for a cozy single-family home or a luxurious villa, Kissimmee's real estate market has something to suit every taste and budget.

In addition to the allure of poolside living, residents of Kissimmee enjoy easy access to world-class attractions, outdoor adventures, and a thriving local economy. From the breathtaking landscapes of Lake Tohopekaliga to the bustling shops and restaurants along the historic downtown, there's never a dull moment in this lively community.

So, if you're searching for a home that combines comfort, convenience, and a touch of paradise, look no further than Kissimmee, Florida. Dive into the lifestyle you’ve always dreamed of, where every day feels like a vacation!

Newest Kissimmee Homes with Pool Amenities

1894 Cassidy Knoll Drive, Kissimmee
$545,000
5 Beds ⋅ 4 Baths ⋅ Kindred Ph 1e SubDv. ⋅ 34744 Zip Code
Virtually Staged. Welcome to 1894 Cassidy Knoll, an exceptional home in the highly sought-after Kindred community featuring one of the largest and most desirable floor plans ever offered in the neighborhood. No longer available from the builder, this expansive design is known for its generously sized rooms, outstanding functionality, and flexible living spaces. The enormous first-floor primary suite offers exceptional privacy and convenience, complete with a massive walk-in closet and a unique, code-compliant doorway providing direct access to the garage. This thoughtful upgrade allows homeowners to come and go without disturbing the rest of the household. The home also features another spacious bedroom with a private en-suite bathroom, ideal for guests or multigenerational living, along with a versatile flex room that could serve as a formal dining room, home office, or potential sixth bedroom. What truly separates this home from others in Kindred is the extensive investment in aftermarket upgrades. The backyard features a massive 44-by-15-foot professionally installed paver lanai, offering approximately 660 square feet of outdoor entertaining space. A newly fenced backyard and a 7-by-7-foot shed/workshop, which conveys with the property, provide even more functionality. Inside, all carpeted areas have been replaced with premium luxury vinyl plank flooring. Exterior improvements include a widened driveway designed to accommodate larger vehicles and a paver walkway connecting to the driveway. The garage is equally impressive, featuring epoxy flooring, multiple 220-volt outlets suitable for electric vehicle charging equipment, a granite-topped utility sink, and additional washer and dryer hookups. While the main laundry room is upstairs, the garage provides the flexibility for a second laundry area. Two separate garage access points and a newer whole-home water softener and filtration system add even more convenience. Kindred offers an outstanding location just minutes from Florida's Turnpike, allowing residents to bypass much of the congestion along US 192. Shopping, dining, and everyday conveniences are nearby, while Walt Disney World is approximately 25 to 30 minutes away. The community also features its own K-8 school and resort-style amenities, including a swimming pool, clubhouse, fitness center, tennis courts, and basketball courts. A future commercial section is also planned within the community. With its rarely available floor plan, oversized bedrooms, first-floor primary suite, incredible outdoor entertaining space, and extensive upgrades, 1894 Cassidy Knoll offers a combination of size, comfort, and functionality that is increasingly difficult to find in today's new construction.

1894 Cassidy Knoll Drive, Kissimmee
1884 Southbury Drive, Kissimmee
$513,985
5 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Under Construction. Kindred presents the Hayden. This amazing all concrete block construction single-family home features 5 bedrooms and 3 bathrooms optimizing living space with an open concept layout. The kitchen overlooks the dining area and great room, while having a view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, beautiful quartz countertops and stainless-steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play, a bedroom, and full bathroom. As we head up to the second floor, we are greeted with bedroom one that features an en suite bathroom as well as three additional bedrooms that surround a second living area, a full bathroom, and a laundry area. Like all homes in Kindred, the Hayden includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1884 Southbury Drive, Kissimmee
1888 Southbury Drive, Kissimmee
$491,790
4 Beds ⋅ 3 Baths ⋅ Kindred SubDv. ⋅ 34744 Zip Code
Under Construction. Inside this beautiful 4-bedroom, 3-bathroom home welcomes the Multi-Gen where you will find 2,077 square feet of comfortable living. The first Bedroom on the left has it’s own bathroom and sitting area with a kitchenette and a private entry to come and go as you please. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect for everyday living and entertaining. The kitchen features modern cabinets, quartz countertops, and sleek stainless-steel appliances. You'll never be too far from the action with the living and dining area right there. Find RevWood Select Flooring throughout a majority of the home including the family room, primary bedroom, kitchen, bathrooms, laundry and foyer. The primary bedroom has its own attached bathroom that features a walk-in closet and 2 sink vanity. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

1888 Southbury Drive, Kissimmee
91 Club Villas Lane, Kissimmee
$289,000
2 Beds ⋅ 2 Baths ⋅ Remington Ph 1 Tr A SubDv. ⋅ 34744 Zip Code
Looking for a maintenance free home where peaceful golf course living meets everyday convenience? You've found it right here in the gated Club Villas community within Remington! Perfectly positioned on a cul-de-sac overlooking the Remington Golf Course, this charming 2-bedroom, 2-bathroom villa offers 1,306 heated square feet of comfortable living space and picturesque views extending across the fairway to a serene pond beyond. Step through the covered, enclosed front porch into a spacious open-concept living area, where the living room features soft carpet flooring and sliding glass doors leading to a second covered and enclosed porch—the perfect place to unwind while taking in the beautiful surroundings. The kitchen offers a bright, crisp aesthetic with white cabinetry, white and grey granite countertops, tile flooring, and an adjoining dining area. A cozy dinette framed by a bay window overlooks the golf course, creating an ideal spot for morning coffee, casual meals, or simply enjoying the view. Both bedrooms are generously sized, while the primary suite features a private en-suite bathroom and dual closets. Beyond the villa, residents enjoy the added privacy of a gated community tucked inside Remington, an active community centered around the Remington Golf Course. The location places you approximately one mile from the Florida Turnpike entrance and within close proximity to shopping, dining, medical facilities, and schools. The Saint Cloud Lakefront is also nearby, offering four miles of walking paths, a splash pad and playground, marina and fishing pier, along with waterfront dining at Crabby Bill’s. With golf course and water views, two enclosed porches, a cul-de-sac location, and convenient access to so many of the area’s amenities, this villa offers a lifestyle and location ready to welcome its new owners.

91 Club Villas Lane, Kissimmee
2963 Sera Bella Way, Kissimmee
$500,000
3 Beds ⋅ 3 Baths ⋅ Sera Bella SubDv. ⋅ 34744 Zip Code
A 3-bed single family residence in Sera Bella with water views, a private entrance in-law suite, and potential 4th bedroom flexibility is hard to find in Kissimmee. This 2-story home offers 2,416 heated square feet, 2.5 baths, a 2-car garage, pond views with fountains and lights, and access to Sera Bella community amenities. This beautifully maintained home in Kissimmee’s 34744 area delivers the space, layout, and location buyers want. The inviting exterior features a brick paver driveway, covered entry, landscaped curb appeal, sidewalks, and an attached 2-car garage. Inside, the bright floor plan offers ceramic tile flooring, formal dining, a spacious living room, and a comfortable family room that flows naturally into the kitchen. The kitchen features granite counters, stainless steel appliances, a center island, closet pantry, stone counters, and generous workspace for everyday meals or entertaining. One of the home’s most valuable features is the attached in-law suite with a kitchenette, studio layout, and private entrance, creating added flexibility for guests, extended stay needs, a work-from-home setup, or a private retreat. Upstairs, the primary suite offers tray ceilings, a walk-in closet, dual sinks, granite counters, a garden bath, and a separate shower. Two additional bedrooms, an upstairs laundry room, and a spacious loft complete the second floor. The loft has excellent potential to become a 4th bedroom, with an existing built-in area intended for a closet. The covered, enclosed, screened rear porch overlooks the pond, where fountains and evening lights create a peaceful backdrop for relaxing or entertaining. Convenient to Lake Nona, Medical City, shopping, dining, major roads, Orlando International Airport, and Central Florida attractions.

2963 Sera Bella Way, Kissimmee
1512 Fernmeadow Street, Kissimmee
$360,000
3 Beds ⋅ 2 Baths ⋅ Kindred Ph 2c & 2d SubDv. ⋅ 34744 Zip Code
Welcome to 1512 Fernmeadow Street in the desirable Kindred community. This nearly new DR Horton Jemison floorplan features an open layout with a bright great room, stainless steel appliances, an oversized walk-in pantry, and smart home features. The private primary suite offers an ensuite bath with double vanity and walk-in closet, while two additional bedrooms provide space for guests, an office, or flexible living. Kindred offers resort-style amenities including pools, clubhouses, a fitness center, playgrounds, sports fields, a dog park, picnic areas, and walking and biking trails. Conveniently located near US-192 and Florida’s Turnpike, with easy access to NeoCity, Lake Nona, Orlando International Airport, Disney, shopping, dining, and downtown Kissimmee. Enjoy low-maintenance living with great amenities and convenient access to everything Central Florida has to offer.

1512 Fernmeadow Street, Kissimmee
2578 Autumn Peace Drive, Kissimmee
$469,500
3 Beds ⋅ 2 Baths ⋅ Tohoqua SubDv. ⋅ 34744 Zip Code
Welcome to this beautiful single-family home in the desirable Tohoqua community, built by Pulte in 2022. This modern home offers 3 bedrooms, 2 bathrooms, and a versatile flex room that can be used as a home office, den, playroom, or additional living space. The home features a modern look and thoughtfully designed layout, with an open-concept living area that creates a comfortable flow for everyday living and entertaining. Step outside to enjoy the fenced backyard and screened-in lanai, providing a comfortable outdoor space to relax, enjoy the Florida weather, or entertain guests. Built with modern construction and contemporary design, this home provides the benefits of newer construction in a desirable community. Tohoqua offers a variety of amenities and a convenient location with easy access to shopping, dining, major roads, and the surrounding Central Florida area. Don't miss the opportunity to make this beautiful home your own!

2578 Autumn Peace Drive, Kissimmee
2512 Brookstone Drive, Kissimmee
$452,000
4 Beds ⋅ 3 Baths ⋅ Remington Prcl I SubDv. ⋅ 34744 Zip Code
Virtually Staged. MUST SEE! Discover an exceptional combination of space, flexibility, and indoor-outdoor living in this impressive 2,469-square-foot home located in the gated Remington Golf Resort community. Featuring 4 bedrooms, a flexible bonus room that can be used as a fifth bedroom, 3 full bathrooms, and a 3-car garage, this home offers the generous living space and versatility today’s buyers are searching for. Even better—a NEW ROOF will be installed before closing with a full price offer! Step inside to a bright, expansive floor plan with updated flooring, refreshed lighting, updated bathroom spaces, abundant natural light, and generously sized rooms throughout. The flexible bonus room provides valuable additional living space and can be used as a fifth bedroom, home office, media room, playroom, or guest retreat. The spacious primary suite opens through French doors to a private deck—an ideal setting for morning coffee, evening relaxation, or your own outdoor retreat. A separate screened patio creates even more space to relax, entertain, and enjoy Florida living throughout the year. The freshly painted exterior makes a striking first impression with Web Gray, Extra White accents, and a Loyal Blue front door. Additional highlights include Ring cameras positioned at the front, side, and rear of the home; dusk-to-dawn front exterior lighting; storage; multiple flexible living areas; a 3-car garage; a low HOA; and the added value of a new roof before closing. Conveniently located near shopping, dining, major roadways, Central Florida attractions, and area recreation, this move-in-ready home delivers the space, updates, and lifestyle features that are increasingly difficult to find. Schedule your private showing—this is a must-see opportunity!

2512 Brookstone Drive, Kissimmee
72 Pine Island Circle, Kissimmee
$290,000
3 Beds ⋅ 2 Baths ⋅ Pine Island Villas At Bvl SubDv. ⋅ 34743 Zip Code
Virtually Staged. POND VIEWS, vaulted ceilings, and a FIRST-FLOOR PRIMARY SUITE—this townhome has the features buyers look for. Natural light fills the open living and dining area, which leads to a screened patio overlooking the water. The kitchen pairs granite countertops with two pantries and a handy pass-through for serving and entertaining. The primary suite offers a walk-in closet and private bath, while two bedrooms, a full bath, and laundry are upstairs. You’ll also find luxury vinyl flooring, granite in the baths, a screened front porch with a generous storage closet, and TWO ASSIGNED PARKING SPACES. A/C was replaced in 2022 and windows and doors in 2023. Close to Disney, Universal, SeaWorld, shopping, and dining, with convenient access to the Turnpike, SR 417, and Orlando International Airport.

72 Pine Island Circle, Kissimmee
1178 Jade East Lane, Kissimmee
$305,000
3 Beds ⋅ 2 Baths ⋅ Jade East Unit 2 SubDv. ⋅ 34744 Zip Code
Affordable, Updated & Move-In Ready! Welcome to this charming 3-bedroom, 2-bath townhome in the desirable gated Jade East community! This home offers an excellent opportunity for a first-time buyer, second home, or investor looking for an affordable property with strong potential. Enjoy an open and comfortable layout, all vinyl flooring, updated appliances, HVAC replaced in 2019, and roof replaced in 2018. The spacious primary suite offers added privacy, while the additional bedrooms provide flexibility for guests, family, or a home office. Conveniently located near shopping, supermarket right across the subdivision, school less than 5 minutes, dining, major highways, and Florida’s Turnpike. Low-maintenance living at an affordable price — a great opportunity you won’t want to miss!

1178 Jade East Lane, Kissimmee
1827 Southfork Drive, Kissimmee
$399,999
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 form 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
2949 Gavin Sky Drive, Kissimmee
$540,000
4 Beds ⋅ 2 Baths ⋅ Seasons At Big Sky SubDv. ⋅ 34744 Zip Code
LAKE VIEWS & OPEN-CONCEPT LIVING! Welcome to this beautiful 4-bedroom, 2-bathroom home in the desirable St. Cloud at the Seasons at Big Sky community in Kissimmee. This inviting home features a bright, open-concept layout with a spacious kitchen, an oversized island with plenty of seating, abundant cabinetry, modern pendant lighting, and a seamless connection to the dining and living areas. Large sliding glass doors bring in plenty of natural light and showcase the beautiful lake views, creating a relaxing setting for everyday living and entertaining. Enjoy the lifestyle Seasons at Big Sky has with resort-style amenities, including a community pool, playground, sports courts, walking trails, and beautifully maintained open spaces. Conveniently located near US-192, major highways, shopping, dining, and Central Florida's world-famous attractions. Come experience the comfort, views, and convenience this home offers!

2949 Gavin Sky Drive, Kissimmee
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