Osceola Homes with Community Pool type

Osceola Homes with Community Pool type

Welcome to Osceola County, Florida, where sunny skies meet vibrant communities and a lifestyle that embraces both relaxation and adventure. Nestled in the heart of Central Florida, Osceola County is known for its diverse recreational offerings, rich cultural heritage, and proximity to world-renowned attractions like Walt Disney World and Universal Studios. With its beautiful landscapes, charming towns, and welcoming atmosphere, Osceola is the perfect place to call home.

One of the standout features of living in Osceola County is the abundance of homes with community pools. Imagine stepping out of your door and diving into a sparkling pool on a warm Florida day! These community amenities not only provide a refreshing escape from the heat but also foster a sense of camaraderie among neighbors. Whether you’re hosting a summer barbecue, enjoying a leisurely swim, or simply soaking in the sun, community pools offer a fantastic way to connect with friends and family while enjoying the beautiful Florida weather.

Osceola County boasts a variety of neighborhoods that cater to diverse lifestyles, from family-friendly communities to serene retreats. Many of these homes with community pools are designed with modern finishes and open layouts, perfect for entertaining or unwinding after a long day. With an array of options, you’re sure to find the ideal home that fits your needs.

Discover the charm of Osceola County and experience the joy of living in a community where relaxation and recreation go hand in hand. Your dream home with a community pool awaits!

Newest Osceola Homes with Community Pool type

$360,000
3 Beds ⋅ 2 Baths ⋅ Remington Prcl G Ph 2 SubDv. ⋅ 34744 Zip Code
Golf-course investment opportunity in Remington. This well-positioned three-bedroom, two-bath single-family home offers approximately 1,816 square feet of living area, a new roof installed in 2026, direct golf-course views and a covered rear lanai. The property is currently leased at $1,925 per month through February 28, 2027 and is being offered subject to the existing lease. Remington community amenities include golf, recreation facilities, pool, tennis courts and walking trails, subject to HOA confirmation. Conveniently located near Florida’s Turnpike, shopping, schools and dining. Seller will consider up to $5,000 toward buyer closing costs with an acceptable offer, subject to contract terms and lender approval. Property is being sold as-is with the buyer’s right to inspect.

119 Southampton Drive, Kissimmee
$360,000
3 Beds ⋅ 3 Baths ⋅ The Terraces At Storey Lake Condo 3 Ph 12 SubDv. ⋅ 34746 Zip Code
Located in the heart of Storey Lake Resort, this fully furnished 3 bedroom, 2 and half bathroom turnkey condo is ready to welcome guests from day one. Thoughtfully designed and fully equipped, it offers investors a seamless opportunity to step into one of Central Florida's most desirable vacation rental markets. Whether you're expanding your investment portfolio, completing a 1031 Exchange, or purchasing your first vacation rental, this property offers the opportunity to own in one of the highest-demand tourist markets in the world. The thoughtfully designed open floor plan features a spacious living area, a modern kitchen with quartz countertops, stainless steel appliances and beautifully appointed furnishings throughout. Everything has been carefully prepared to provide an exceptional guest experience and allow a seamless transition for the next owner. Location is everything and this one delivers. Just minutes from Walt Disney World, Disney Springs, Orlando Vineland Premium Outlets, world-class restaurants, championship golf courses and Central Florida's top attractions, guests enjoy unmatched convenience while owners benefit from one of the region's strongest vacation rental markets. Storey Lake Resort offers an impressive collection of resort-style amenities, including a Clubhouse, Fitness Center, Gated Community with Guard, Resort-Style Pool, Lazy River, Water Park, Restaurant, Playground, and scenic walking paths, creating the kind of guest experience that drives repeat visits and lasting vacation memories. If you're looking for a property that combines location, lifestyle, and investment potential, this fully furnished, move-in-ready condo is an exceptional opportunity to own in one of Orlando's premier short-term rental destinations.

3191 Paradox Circle Unit 208, Kissimmee
$369,900
3 Beds ⋅ 3 Baths ⋅ Regal Oaks At Old Town SubDv. ⋅ 34746 Zip Code
Discover the Perfect Blend of Comfort, Style, and Investment Potential with this beautifully updated Corner-Unit townhome in Regal Oaks Resort, one of Central Florida's most sought-after Gated vacation rental communities. Built during resort's newest development phase, this rare three-bedroom End-unit townhome offers a more Contemporary Design and layout than many of the earlier homes in the community, making it one of the community's most desirable floor plans. Thoughtfully updated throughout, the home features Elegant Decorative Wood Accent Walls, Stylish Wallpaper, Upgraded Lighting, Modern Fixtures, Premium Faucets and Shower Systems, and beautiful Wide-Plank Luxury Vinyl Flooring throughout the entire second floor and staircase, creating a Warm, Contemporary Atmosphere with exceptional durability and easy maintenance. Large windows throughout the home fill every living space with Abundant Natural Light, creating a Bright, Open, and Inviting atmosphere. The spacious open-concept floor plan seamlessly connects the living room, dining area, and kitchen, creating an inviting space for entertaining or relaxing after a day at the parks. The kitchen features Granite Countertops, Stainless-Steel GE Appliances and ample cabinet space. The laundry area includes a modern GE Washer and Dryer, while the home's GE appliances provide quality and consistency throughout the kitchen. Upstairs, the Spacious Owner's Suite overlooks the protected Conservation Area and offers a Private En-suite bathroom with dual vanities, a relaxing soaking garden tub, and peaceful preserve views. Two additional guest bedrooms and another full bathroom comfortably accommodate family and guests. The Screened Lanai provides a peaceful outdoor retreat overlooking the protected preserve, offering privacy with No Rear Neighbors. The home is being sold FULLY FURNISHED and tastefully DECORATED, making it completely Move-In Ready for personal enjoyment or immediate vacation rental use. Regal Oaks Resort offers an outstanding resort lifestyle with a beautiful Clubhouse, resort-style Swimming Pool with Water Slide, Fitness Center, Tennis Courts, Restaurant, Poolside Bar, Arcade, Scenic Lakes, Walking Trails, and 24-hr Guard-Gated security. Daily Valet Trash Collection, Exterior Maintenance, and Lawn Care are all included through the HOA, allowing owners to enjoy a truly low-maintenance ownership experience. Another valuable advantage is that Regal Oaks has no Community Development District (CDD) fees, helping reduce annual ownership costs compared to many competing resort communities. Ideally located in the heart of Kissimmee—Central Florida's Premier Destination for Vacation Homes—the property is approximately 9 miles from Disney Springs and offers convenient access to Walt Disney World, Universal Orlando Resort, Celebration, Sunset Walk, Margaritaville Resort Orlando, Island H2O Water Park, championship golf courses, shopping, dining, and I-4. This property is an established, income-producing vacation rental with an excellent rental history, Outstanding Guest Reviews & Future Reservations already in place. Subject to management continuity existing reservations may transfer to the new owner, allowing rental income to continue immediately after closing with $400 value photo package. Whether you're searching for a FL vacation home or a proven investment in one of Orlando's strongest vacation rental markets, this exceptional Regal Oaks property offers an outstanding opportunity.

2679 Corvette Lane, Kissimmee
$1,365,000
5 Beds ⋅ 4 Baths ⋅ Celebration East Village Unit 3 SubDv. ⋅ 34747 Zip Code
Updated 4-bedroom and 3-bath home in Celebration's fantastic East Village, with a private 1-bedroom, 1-bath garage apartment. From the moment you arrive, classic Victorian charm, an inviting front porch, and mature landscaping create an unforgettable first impression. Inside, a convenient floor plan is filled with natural light and thoughtfully designed gathering spaces perfect for everyday living and entertaining. The heart of the home is the extensively improved chef's kitchen, featuring granite countertops, custom cabinetry, a six-burner gas range with pot filler, Bosch dishwasher, Liebherr refrigerator, wine cooler, expanded pantry, coffee bar, and abundant storage. The kitchen opens seamlessly into comfortable living spaces including the family room, dining room, and a bright sunroom/game room that steps out to the private outdoor entertaining area. The first floor also offers a full guest bath and a flexible bedroom that easily functions as a private office. Upstairs, the spacious primary suite has been beautifully enhanced with a fully remodeled bath (2023) featuring a luxurious rain shower, electronic temperature controls, custom lighting, and an updated walk-in closet. Two additional bedrooms upstairs: one bedroom with a murphy bed and the newly added fourth bedroom (2026), a laundry area, an updated guest bath complete the second floor. Outdoor living is equally inviting with a courtyard, paver patio, and pergola, a great place to add an outdoor cooking station. The attached garage includes a completely custom-designed one-bedroom apartment with its own private entrance added in 2017, full kitchen with gas range & quartz countertops, living room, laundry, updated bath, and fenced patio; this gives flexibility for families and guests. This home has been continually improved for comfort and efficiency with a new roof (2018), newer A/C, Anderson double-pane windows, engineered wood flooring, spray foam insulation, fresh air ventilation system, gas water heater, EV charger, and a solar panel system that helps provide exceptionally low electric costs. Located just minutes from Celebration's charming downtown, residents enjoy more than 26 miles of walking and biking trails, neighborhood parks, community pools, year-round events, boutique shopping, restaurants, and convenient access to Disney, I-4, SR-417, and US-192. Homes like this rarely become available—a residence where classic Celebration charm meets today's modern conveniences, creating a home that's as beautiful to live in as it is to admire.

828 Morning Glory Lane, Celebration
$380,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook South Ph I-1 & J-1 SubDv. ⋅ 33896 Zip Code
If you're looking for peaceful living in a resort-like community, look no further than the Retreat at Champions Gate. This beautiful 4-bedroom, 3-bath home is move-in ready and allows for short-term rentals. The freshly updated interior boasts a gorgeous open-concept layout and bright interior. Upon entering, you'll notice 10' ceilings. A large open kitchen is the heart of your home with quartz countertops and stainless steel appliances, a peninsula, and a vented range with both 42-inch and floor-to-ceiling cabinetry. Featuring a ground-floor private suite facing north. You will enjoy dual sinks with a vanity and a large walk-in shower. The additional 3 bedrooms are nicely sized and well located upstairs, offering plenty of space for family or guests. Make your way out back where you will love spending time relaxing in the screen-enclosed pool. Only minutes from Disney and Universal Resorts and Disney City Walk. The HOA includes cable, high-speed internet, a resort-style pool and splash pad, mini-golf, arcade, ice cream shop, restaurant and bar, fitness center, playgrounds, and a dog park. This is a Fannie Mae Homepath property.

1592 Moon Valley Drive, Davenport
$525,000
5 Beds ⋅ 5 Baths ⋅ Paradise Palms Resort Ph 4 SubDv. ⋅ 34747 Zip Code
**Exceptional 5-Bedroom Resort-Style Home in Prime Kissimmee Location!!!!This beautifully upgraded home at 2908 Banana Palm Dr puts you minutes from world-famous theme parks, shopping, restaurants, major roads, and the airport. Welcome to the perfect blend of comfort and convenience in one of Florida's most sought-after vacation destinations. Step inside this spacious 2-story home featuring over 3,000 square feet of thoughtfully designed living space. The grand entry showcases custom tile work and elegant shadow box molding that flows through the living room and dining area. Soaring vaulted ceilings and high ceilings throughout create an open, airy feel you'll love. The completely renovated kitchen is a chef's dream with brand new cabinets and porcelain countertops installed May 2025. Premium Forno appliances include a double wall oven, 36-inch French door electric range with convection, oversized 40-inch refrigerator, and a convenient microwave drawer built into the cabinetry. All five bedrooms offer comfortable retreats, with the primary bath featuring a modern bidet toilet. New LVP flooring runs throughout the entire home, while bedrooms feature cozy carpet. Recent upgrades include a new HVAC system (July 2025), hot water heater (April 2025), pool filter (November 2025), and washer/dryer (April 2025). Relax in your private screened pool and spa with privacy screens, backing up to a peaceful nature preserve. The resort-style community amenities are incredible: clubhouse, fitness center, Tiki bar, pool, two hot tubs, splash park, waterslide, movie theater, sauna, and sports courts. With over $100,000 in upgrades, this move-in ready home is approved for short-term rentals, making it perfect for personal use or investment income. Don't miss this incredible opportunity!

2908 Banana Palm Drive, Kissimmee
$695,000
5 Beds ⋅ 6 Baths ⋅ Reunion West Ph 1 East SubDv. ⋅ 34747 Zip Code
Welcome to 7564 Marker Avenue, an outstanding turnkey investment and lifestyle opportunity in the highly desirable gated resort community of Encore at Reunion, just minutes from Walt Disney World and Orlando’s world-class attractions. This fully furnished, professionally themed 5-bedroom, 5.5-bath luxury home offers over 3,300 square feet of thoughtfully designed living space, blending comfort, style, and strong short-term rental potential. The open-concept main level features a spacious family room, dining area, and modern kitchen, with the primary suite conveniently located on the first floor for added privacy and functionality. Upstairs, guests will find additional themed bedrooms and a versatile bonus/game room, creating an immersive vacation experience that consistently appeals to short-term rental guests. The home is designed for maximum occupancy appeal while still offering a warm and inviting feel for personal use. Step outside to your private resort-style pool and spa, complete with outdoor lounging space ideal for relaxing or entertaining after a day at the parks. All furnishings are included, making this a true turnkey purchase opportunity ready for immediate enjoyment or rental income. Located within Encore at Reunion, residents and guests enjoy world-class amenities including a water park, clubhouse, fitness center, tennis courts, and 24-hour gated security. With its prime location, strong vacation rental demand, and resort-style features, this property represents an exceptional opportunity for both personal enjoyment and income-producing investment.

7564 Marker Avenue, Kissimmee
$389,900
3 Beds ⋅ 2 Baths ⋅ East Lake Preserve Ph 3 SubDv. ⋅ 34744 Zip Code
Welcome to this beautifully designed 3-bedroom, 2-bath home plus a versatile bonus room featuring a walk-in closet; ideal as a home office, playroom, guest room, or 4th bedroom. Enjoy indoor and outdoor living with a welcoming front porch and a covered screened lanai overlooking the fenced backyard. The open concept layout offers a spacious living area, ideal for everyday living and entertaining. The kitchen features granite countertops, a large island, espresso 42-inch cabinetry with crown molding, stainless steel appliances, undermount sink, and ample storage. The private owner's suite includes a walk-in closet and an en-suite bath with dual granite vanities and glass enclosed shower. Two additional bedrooms, a second full bathroom, and a generously sized utility room complete the home. Additional highlights include in-wall pest control, dual-pane windows, and barrier roof sheathing for energy efficiency. Community amenities include a pool, playground, dog park, and internet service included in the HOA dues. Ideally located with easy access to SR-417, this home is just 5 miles from Boxi Park and Lake Nona Medical City, 7 miles from Orlando International Airport, and short distance to shopping, dining, and top-rated schools. Experience the perfect combination of modern comfort, community amenities, and great location.

2732 E Lake Pointe Drive, Kissimmee
$325,000
3 Beds ⋅ 3 Baths ⋅ Storey Lake Tr K SubDv. ⋅ 34746 Zip Code
Virtually Staged. Welcome Home to 2935 Theme St! Move-in ready, this 3-bedroom, 2.5-bath townhome offers 1,859 sq ft of open-concept living in the heart of Central Florida. From the moment you arrive, the home's charming coastal-craftsman exterior — with paver driveway and manicured landscaping — sets the tone for what's inside... Step through the front door into a spacious great room that flows seamlessly into the kitchen and dining area, all finished with tile flooring throughout the main level. The kitchen features espresso cabinetry, stainless steel appliances, a subway tile backsplash, and a center island with pendant lighting. Upstairs, the primary suite offers a peaceful retreat with a tray ceiling, walk-in closet, and en-suite bath, while two additional bedrooms provide flexible space for family, guests, or a home office. A convenient half bath downstairs and in-unit laundry add everyday functionality. Outside, enjoy a private patio and an insulated 2-car garage that stays cool year-round. HOA includes access to a community pool, dog park, cable, and WiFi. Located just minutes from Orlando's world-famous attractions, shopping, dining, and major highways, this townhome combines comfort, style, and unbeatable convenience. Don't miss this one and schedule your private showing today!

2935 Theme Street, Kissimmee
$144,900
1 Beds ⋅ 1 Baths ⋅ Gables At Lakeside Condo SubDv. ⋅ 34741 Zip Code
Discover a fantastic lake-view opportunity at The Gables at Lakeside in the heart of Kissimmee! Located on the second floor, this condominium offers beautiful water views, a feature not available with every unit in the community. The HVAC system was replaced in 2025, providing a valuable recent update. Currently vacant and ready for a quick closing, the property was previously leased for $1,575 per month, offering flexibility for an owner-occupant or investor. Community amenities include a swimming pool and tennis courts. Enjoy comfortable condominium living with a scenic lake view and convenient access to all that Kissimmee has to offer.

1229 Bermuda Lakes Lane Unit 206, Kissimmee
$889,999
7 Beds ⋅ 6 Baths ⋅ Split Oak Estates Ph 2 SubDv. ⋅ 34771 Zip Code
Wow!! 5,486 square feet under air! This is a true 7 bedroom 5/1/2 bathroom home with a full size loft and game room! This home is still under the builder warranty and is fully equipped with all the appliances, water filtration system and tons of storage space. There are 2 master suites. All the bedrooms have a private walk-in closet and 3 bedrooms have an onsuite bathroom. There are too many upgrades to list with a kitchen equipped for entertaining with a waterfall island, quartz countertops and stainless steel appliances. The showpiece of this beautiful home is the large backyard paver patio with a full size outdoor kitchen. The extended paver patio is 50x25! All this in the growing Sunbridge area but without expensive HOA fees and no CDD fee.

2764 Matera Drive, St Cloud
$439,900
4 Beds ⋅ 2 Baths ⋅ Wyndham Palms Ph 3 SubDv. ⋅ 34747 Zip Code
Do you visit Orlando so much that it simply makes more sense to own a vacation home there?  Do you often stay at hotels and Airbnbs and wish you had more of a "home" feel to enjoy your stay?  If you answered yes to any of these.....then 2220 Wyndham Palms Way in Kissimmee could be your next home away from home!  Securely located in a 24-hour guard-gated community, this fully furnished home has just undergone a very successful renovation and is now ready for its new owners.  Once across the threshold you can instantly appreciate the sellers have done for you; starting with a 100% updated kitchen that includes new quartz countertops, new cabinetry, new hardware, floating shelves and updated appliances, making this an entertainer's dream.  New laminate flooring leads you from the entryway and throughout the entire home, leaving not one stitch of carpet to walk on or worry about cleaning.  A two-way split floor plan creates additional privacy, with the primary bedroom located on the right side of the home, tastefully updated with custom woodwork and sconces that flank the brand new bedroom set.  Your hotel-like en-suite bathroom does not fall short in any way; and has matching quartz and cabinetry as the kitchen and secondary bathroom.  Three other generously sized bedrooms are on the opposite side of the home, each with its own brand new bedroom set and serviced by its own, very well-updated bathroom.  A thoroughly outfitted game room includes a billiards table, games for your guests, as well as its own private TV.  If you're ready to enjoy the Florida sun, this stunning back patio and pool area will not disappoint!  Tea lights set the backdrop for movie night by the pool, where you can create endless memories with your friends and family, and have guests leaving 5 stars after their stay.  > BRAND NEW FURNITURE | 100% UPDATED KITCHEN & BATHROOMS | LAMINATE FLOORING THROUGHOUT | 2018 ROOF | 2021 HVAC | 2024 POOL PUMP | 2020 POOL HEATER | 2022 WATER HEATER | < UP TO 70% OCCUPANCY & POTENTIAL NOI OF $35,000+.  Don't you deserve to own a piece of the Florida sunshine in 2026?

2220 Wyndham Palms Way, Kissimmee
Start Your Search