Kissimmee Homes with Private Pool type

Kissimmee Homes with Private Pool type

Welcome to Kissimmee, Florida—a vibrant gem nestled in the heart of Osceola County, just a stone's throw away from the enchanting attractions of Orlando. Known for its rich history, diverse culture, and family-friendly atmosphere, Kissimmee offers a unique blend of urban conveniences and natural beauty. With its picturesque parks, scenic lakes, and abundant recreational opportunities, this area is perfect for those seeking both adventure and tranquility.

One of the standout features of Kissimmee is its stunning homes with private pools. Imagine stepping out into your own personal oasis, where you can soak up the Florida sun, host lively barbecues, or simply unwind after a day of exploring the nearby theme parks. These homes are designed with comfort and leisure in mind, often featuring spacious layouts, modern amenities, and beautiful outdoor spaces that enhance your lifestyle.

Living in Kissimmee means you’re never far from world-renowned attractions such as Walt Disney World, Universal Studios, and SeaWorld. Yet, you can retreat to your serene haven at the end of the day, enjoying the luxury of a private pool that allows you to relax in style. Whether you’re looking for a vacation rental or a permanent residence, Kissimmee’s homes with private pools offer the perfect blend of excitement and relaxation.

Discover the charm of Kissimmee and experience the joy of living in a home where every day feels like a vacation. Embrace the Florida lifestyle and make your dream of owning a home with a private pool a reality in this enchanting region!

Newest Kissimmee Homes with Private Pool type

$1,549,000
5 Beds ⋅ 4 Baths ⋅ Florida Fruit Belt Sls Co SubDv. ⋅ 34744 Zip Code
Experience elevated country living in this rare, custom-built estate compound set on 5.23 fully cleared and fenced acres in the heart of Kissimmee. Designed for both privacy and functionality, the property features two separate concrete driveways with electronic gated entry for seamless access. The main residence offers 5 bedrooms, 3.5 bathrooms, and a 3-car garage, with a thoughtfully designed split, open-concept floor plan. Light-filled living spaces include formal living and dining areas, a spacious family room, and a striking Chicago brick wood-burning fireplace that anchors the home with warmth and character. A large bonus room and screened living area provide flexible space for entertaining and everyday comfort. Outdoors, enjoy a true resort-style experience with a stunning pool and waterfall feature, complemented by a dedicated pool bath for guests. Expansive front and rear views showcase the beauty and scale of the property. For car enthusiasts, hobbyists, or business use, the nearly 4,000 sq ft steel-constructed outbuilding is equipped with upgraded electrical and a car lift, offering exceptional versatility. An additional bonus/play space above the garage adds even more room for recreation or creative use. A unique blend of space, style, and capability—this is a one-of-a-kind opportunity ready for immediate enjoyment.

2745 Lloyd Lane, Kissimmee
$395,995
3 Beds ⋅ 2 Baths ⋅ Bvl Unit 9 6th Add SubDv. ⋅ 34743 Zip Code
POOL HOME + PAID-OFF SOLAR + NO HOA! Your Florida lifestyle starts here! This spacious 3-bedroom, 2-bath home with a two-car garage features an open floor plan, split-bedroom layout, vaulted ceilings, and beautiful tile flooring. The updated kitchen shines with quartz countertops, 42-inch shaker cabinets, stainless steel appliances, and a breakfast bar perfect for entertaining. Unwind in the spacious primary suite featuring a large walk-in closet and an upgraded bathroom with a beautifully tiled walk-in shower. The backyard is where the vibes come alive! Fire up the grill, gather with family and friends on the spacious patio deck, then cool off in your private in-ground pool. The oversized, fully fenced lot provides plenty of privacy and room to enjoy. Best of all, the solar panels are fully paid off—no solar loan or lease payment! Conveniently located near Florida’s Turnpike, Medical City, major hospitals, shopping, dining, Orlando International Airport, and Central Florida attractions. Don’t miss this opportunity—schedule your private showing today!

247 Competition Drive, Kissimmee
$549,900
4 Beds ⋅ 2 Baths ⋅ Breckenridge SubDv. ⋅ 34744 Zip Code
Virtually Staged. Welcome to Breckenridge, an all-age community located just off Kings Highway in Kissimmee. This 4-bedroom, 2-bathroom fenced home offers expansive living on nearly half an acre with versatile spaces and major mechanical peace of mind. The front entryway opens directly to formal living and dining areas designed for fluid entertaining. In the heart of the home, a generous kitchen equipped with stainless steel appliances provides clear views out to the sparkling pool and overlooks the family room, complete with a cozy wood-burning fireplace and a casual dinette area. The primary retreat offers exceptional privacy, featuring a large walk-in closet and an en-suite layout with two separate vanities located in individual rooms—each featuring its own sink—alongside a soaking jacuzzi tub and separate shower. On the opposite wing, two comfortable guest bedrooms share a full bath with dual sinks, conveniently positioned near the interior laundry room. The fourth bedroom was converted from a one-car garage into a true bedroom complete with a closet and central air, while the fifth room is an air-conditioned bonus room converted into an office with private exterior access out to the spacious yard, all while still maintaining a functional two-car garage. Outdoor living shines with a 12x30 fiberglass pool and an outdoor prep sink within the fully fenced yard. The expansive parking footprint includes the two-car garage alongside a massive driveway built to accommodate 8 to 11 vehicles, offering ample space for multi-vehicle households and guest parking. Major capital improvements have all been completed, including a new roof installed in October 2024, energy-efficient replacement windows rated to withstand 140mph winds from 2021, and both the central air conditioning system and water heater replaced in April 2025. Make this your new home and schedule your private tour today!

1730 Kasey Court, Kissimmee
$625,000
4 Beds ⋅ 6 Baths ⋅ Remington Ph 1 Tr C SubDv. ⋅ 34744 Zip Code
STUNNING POOL HOME IN THE GATED GOLF COMMUNITY OF REMINGTON! New Roof (Jan. 2025) New Water Heater (May 2025) Exceptional 4-bedroom, 5½-bath pool home offering 4,146 heated square feet of living space in the highly sought-after gated community of Remington in Kissimmee. From the moment you arrive, you'll appreciate the expansive 3-CAR SIDE-ENTRY GARAGE, complete with a WORKSHOP AREA and EV CHARGER. Step inside to a welcoming first floor with the spacious family room features a GAS FIREPLACE, while the large kitchen offers plenty of cabinetry, workspace, and a comfortable dinette area. A separate FORMAL DINING ROOM provides an elegant space for special occasions. The PRIVATE OFFICE, enclosed by French doors and accented by a beautiful chandelier, is ideal for working from home. The first-floor guest bedroom offers convenient access to a bathroom, making it perfect for guests or multigenerational living. A DEDICATED LAUNDRY ROOM with Washer and Dryer plus additional storage. Upstairs, the IMPRESSIVE PRIMARY SUITE that offers a luxurious private retreat. Step outside on your PRIVATE BALCONY overlooking the sparkling pool and golf course—the perfect spot to enjoy your morning tea or unwind at the end of the day. The spacious en-suite bathroom features a garden tub, separate shower, water closet, dual sinks, and THREE WALK IN CLOSETS! The second bedroom is an incredible 23' x 13' and includes a sitting area, TWO closets, and a private en-suite bath. The third upstairs bedroom also features its own en-suite bath and two closets. You will have plenty of storage throughout. For movie nights and entertaining, head to the dedicated movie room, creating the perfect space for family fun or just relaxing at home. Step outside to your private SCREENED POOL AND SPA, where Florida living comes to life. The outdoor space includes a FULL POOL BATH with shower, making it easy to enjoy the pool without having to track water through the home. The pool heater and indoor fireplace are both powered by gas. Located in the GATED GOLF COURSE COMMUNITY of Remington with amenities that include FITNESS CENTER, POOL, Basketball Courts, Tennis Courts, Baseball Field, Sand Volleyball, Security, and Playgrounds. This home offers a desirable location with a community atmosphere and convenient access to Central Florida's world-class attractions, shopping, dining, and major roadways. With an abundance of living space, generously sized bedrooms and closets, private pool and spa, balcony overlooking the pool and golf course, three-car garage, movie room, office, and recent major upgrades, this is an exceptional opportunity to enjoy spacious Florida living in a sought-after gated golf community. Don't miss the opportunity to make this remarkable home yours!

156 Burrell Circle, Kissimmee
$549,900
4 Beds ⋅ 3 Baths ⋅ Pebble Pointe SubDv. ⋅ 34743 Zip Code
Welcome to 2753 Woodstream Circle, a spacious 4-bedroom, 2.5-bath pool home in the desirable Pebble Pointe community of Kissimmee, Florida. Offering approximately 2,341 square feet of living space on a quarter-acre homesite, this two-story Central Florida home combines generous indoor living areas with a private screened pool, heated spa, fenced backyard, and an excellent location near shopping, dining, major roadways, and Orlando-area attractions. Step inside to an impressive open interior featuring vaulted and high ceilings, abundant natural light, wood flooring, and ceramic tile. The functional floor plan places the primary suite on the first floor, providing additional privacy and convenience, while three secondary bedrooms and a spacious bonus room are located upstairs—ideal for a home office, media room, playroom, or additional living space. At the heart of the home is a spacious kitchen featuring granite/stone countertops, extensive wood cabinetry, stainless-steel appliances, a large center island with seating, and an open connection to the family room, making the space perfect for everyday living and entertaining. The first-floor primary suite offers generous space and an updated en-suite bathroom highlighted by a large walk-in tiled shower with frameless glass enclosure, dual shower fixtures, dual sinks, granite countertops, and abundant vanity storage. Then step outside and experience one of this home's standout features: your own private Florida outdoor retreat. Enjoy a screen-enclosed gunite swimming pool and heated spa, expansive pool deck, fenced backyard, courtyard-style outdoor areas, mature landscaping, and extensive paver surfaces providing plenty of room for relaxing and entertaining. Additional features include an attached 2-car garage, interior laundry room, block/stucco construction, shingle roof, public water and sewer, and a low-maintenance outdoor lifestyle. Located in Kissimmee, Osceola County, this home provides convenient access to Central Florida shopping, restaurants, schools, recreation, major transportation corridors, and everything the Orlando/Kissimmee area has to offer.

2753 Woodstream Circle, Kissimmee
$499,900
4 Beds ⋅ 3 Baths ⋅ Woods At Kings Crest The Ph 1 SubDv. ⋅ 34744 Zip Code
*This home can be purchased with NO MONEY DOWN or NO INCOME VERIFICATION* Welcome to 2207 Jessica Lane, a beautifully maintained 4-bedroom, 2.5-bath pool home situated on an oversized .34-acre lot in the established Woods at King’s Crest community. Offering nearly 2,000 square feet of living space, this home combines comfort, space, and thoughtful updates throughout. Major improvements and finishes have been updated within the last 10 years, including a newer roof, giving the next owner added peace of mind. Step outside to your own private Florida retreat featuring a screened-in pool and spacious backyard with plenty of room to relax, entertain, or enjoy year-round outdoor living. Inside, the functional floor plan provides generous living and entertaining spaces, four well-sized bedrooms, and the convenience of 2.5 bathrooms. The property also features a two-car garage, public water, and an established neighborhood setting with NO CDD. Conveniently located near shopping, dining, schools, major roadways, and everything Central Florida has to offer. Whether you’re hosting by the pool or enjoying a quiet evening at home, 2207 Jessica Lane offers the space and lifestyle you’ve been looking for. Schedule your private showing today!

2207 Jessica Lane, Kissimmee
$378,000
3 Beds ⋅ 2 Baths ⋅ Bvl Unit 10 3rd Add SubDv. ⋅ 34743 Zip Code
WATER VIEW + PRIVATE POOL! Welcome to this beautiful 3-bedroom, 2-bath home featuring a bright and spacious open floor plan designed for comfortable Florida living. The generous living area offers plenty of space for relaxing and entertaining, while tile flooring throughout the entire home provides easy maintenance and a clean, cohesive look. Step outside to your private backyard oasis featuring a sparkling pool and beautiful water views—the perfect setting to relax, entertain, and enjoy Florida’s outdoor lifestyle. A brand-new fence was recently installed to provide additional privacy while still preserving the beautiful water view. Major improvements include a NEW ROOF installed in June 2022 and a NEW HVAC system installed in January 2026, offering added peace of mind for the next owner. With its open layout, private pool, peaceful water view, spacious living area, and valuable recent upgrades, this home is ready for its new owner.

168 Seabreeze Circle, Kissimmee
$410,000
3 Beds ⋅ 2 Baths ⋅ Sheffield At Lakeside Estates Ph 3 SubDv. ⋅ 34743 Zip Code
Very comfortable and spacious 3 bedroom 2 bath with an inground pool. Come and make it yours.

1837 Wimbledon Street, Kissimmee
$659,900
4 Beds ⋅ 3 Baths ⋅ Rustic Acres Unit 3 SubDv. ⋅ 34744 Zip Code
Beautiful single-story pool home situated on more than half an acre in the peaceful, tree-lined neighborhood of Rustic Acres, conveniently located near the vibrant Lake Nona area. Step through the impressive double front doors into a bright, open interior featuring soaring 10-foot ceilings and oversized windows that fill the home with natural light. The thoughtfully designed split-bedroom floor plan is ideal for both everyday living and entertaining. The chef-friendly kitchen features double ovens, granite countertops, upgraded real wood cabinetry, and beautiful backsplash. Expansive folding sliders open wide to create a seamless connection between the indoor and outdoor living spaces. Step outside to the spacious screened lanai and enjoy your own private Florida retreat, complete with a sparkling pool, relaxing spa, and convenient pool bath. Mature trees and established landscaping surround the property, providing an added sense of privacy and tranquility. This 4-bedroom, 3-bathroom home also features a dedicated office, stunning grey wood-look plank tile flooring throughout, an indoor laundry room with utility sink, and an oversized 3-car garage. The extended driveway provides ample parking for multiple vehicles, making the home perfect for entertaining family and friends. Major upgrades add tremendous value and peace of mind, including a private well updated in 2026, PAID-OFF solar panels that convey free and clear, high-impact Storm Stoppers hurricane window protection rated up to 145 mph, a roof replaced in 2020, and a water heater installed in 2023. The location offers the perfect combination of privacy and convenience. Enjoy quick access to Lake Nona's shopping, dining, and Medical City, including the Orlando VA Medical Center, Nemours Children's Hospital, and UCF College of Medicine. State Road 417 and Orlando International Airport are also easily accessible. Central Florida's world-famous attractions—including Walt Disney World, Universal Studios, SeaWorld, Gatorland, and Nona Adventure Park—are within easy reach, while Florida's beaches and Kennedy Space Center are approximately an hour away. If you're looking for a spacious single-story pool home with over half an acre, privacy, valuable upgrades, and convenient access to everything Central Florida has to offer, this Rustic Acres gem is ready to welcome you home!

3162 Harvest Lane, Kissimmee
$499,000
6 Beds ⋅ 4 Baths ⋅ Villa Sol Ph 2 Village 3 SubDv. ⋅ 34744 Zip Code
Nestled within a prestigious gated community, this meticulously maintained sanctuary offers an exceptional blend of elegance, peace of mind, and modern convenience. Step inside to discover a luminous, light-filled interior showcasing fresh, neutral paint and beautiful, low-maintenance luxury vinyl plank flooring that flows seamlessly throughout the main level. At the heart of the home lies a newly transformed chef’s kitchen, thoughtfully designed with stunning granite countertops, a spacious central island for effortless entertaining, sleek stainless steel appliances, and abundant storage to keep everything beautifully organized. Designed with flexibility and indulgence in mind, the residence boasts two primary suites, including a private retreat ideal for a mother-in-law suite, guest sanctuary, or multi-generational living. Unwind at the end of the day in your private backyard oasis, featuring a serene screened-in pool and spa designed for effortless outdoor lounging without the hassle of pests. Beyond your private retreat, resort-style community amenities elevate daily living with access to a sprawling clubhouse, fully equipped fitness center, shimmering pool, tennis and basketball courts, and a charming neighborhood park, offering a perfect balance of active living and peaceful relaxation.

2986 Siesta View Drive, Kissimmee
$520,000
4 Beds ⋅ 4 Baths ⋅ Somerset SubDv. ⋅ 34744 Zip Code
Fully renovated pool home in Remington. This 4-bedroom, 3.5-bath two-story delivers a designer kitchen, a private screened pool and spa, a NEW ROOF (2024), and no carpet anywhere. The showpiece is the chef's kitchen: high-gloss cabinetry to the ceiling with lighted glass display uppers, an oversized quartz waterfall island with bar seating and a built-in dual-zone beverage fridge, double wall ovens, a stainless chimney hood, farmhouse sink, and crystal pendant lighting. The open main level flows from the kitchen through the dining area into a 16x16 great room with sliders to the pool deck, plus a separate formal living room with a dramatic 3D accent wall. Tile runs throughout the first floor with wood-look flooring upstairs. All four bedrooms are up, including a 17x16 primary suite with an en-suite bath featuring a garden tub and separate shower, and an 11x9 custom walk-in closet with built-in drawers and shoe storage. Every bathroom has been updated, including a guest bath with floor-to-ceiling designer tile, a frameless-style glass shower, and a vessel sink. Out back, the covered and screened lanai wraps a sparkling pool with shade sails and string lighting, framed by a turf privacy wall and a paved deck made for entertaining, all backing to the community wall with no rear neighbors. Roof 2024, AC 2018, full interior laundry room, and a 2-car garage. Remington is a golf-cart-friendly community with a clubhouse, pool, tennis and pickleball courts, playgrounds, and a public golf course, with a low HOA. Minutes to Lake Toho, downtown Kissimmee, the Turnpike, and Lake Nona Medical City, about 25 minutes to Orlando International Airport and the parks. Schedule your private showing today.

1017 Berkeley Drive, Kissimmee
$510,000
4 Beds ⋅ 2 Baths ⋅ Villa Sol Ph 2 Village 3 SubDv. ⋅ 34744 Zip Code
Welcome to this STUNNING 4 bed/2 bath POOL home in the GATED COMMUNITY of Villa Sol. This Energy-Efficient home is loaded with UPGRADES and character from the moment you walk through the door! Features include 2 additional DEN/OFFICE rooms, NEWER AC (2023), FULLY OWNED SOLAR PANELS, slat wall panels in the living room, modern fixtures, NEWER APPLIANCES (2023) and an open layout. The gourmet kitchen boasts QUARTZ countertops, a KITCHEN ISLAND with breakfast bar, soft-close drawers, stainless steel appliances and a built-in oven. The spacious primary suite offers an en-suite bathroom with a separate tub and shower, generous vanity space and a WALK-IN CLOSET. Step outside to your private backyard oasis, complete with a SCREEN-ENCLOSED pool (Resurfaced 2024), OUTDOOR KITCHEN with built-in grill, storage shed and plenty of covered space for entertaining! The HOA INCLUDES CABLE, INTERNET & LAWN CARE in addition to the community pool, fitness center, basketball courts, tennis/pickleball courts and clubhouse. Conveniently located near The Loop, shopping, dining, major highways and theme parks. If you’re looking for a beautiful house with incredible indoor and outdoor living, Welcome Home!

3016 Camino Real Drive S, Kissimmee
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