Osceola Homes with Pool Community Features

Osceola Homes with Pool Community Features

Welcome to Osceola County, Florida – a vibrant and picturesque destination that beautifully blends natural beauty with modern living. Nestled in the heart of Central Florida, Osceola County is known for its stunning landscapes, diverse wildlife, and a wealth of recreational opportunities. From the enchanting shores of Lake Tohopekaliga to the lush expanses of the Kissimmee Prairie Preserve, outdoor enthusiasts will find a paradise waiting to be explored.

Osceola County is not just a haven for nature lovers; it’s also a thriving community with a rich cultural tapestry. With charming towns like Kissimmee and St. Cloud, residents enjoy a variety of dining, shopping, and entertainment options. The county is conveniently located near the world-renowned attractions of Orlando, making it the perfect place for families and individuals seeking a balanced lifestyle.

One of the standout features of homes in this delightful region is the abundance of properties with pools. Imagine relaxing in your own backyard oasis, soaking up the Florida sun or hosting delightful gatherings with friends and family. Homes with pool community features in Osceola County offer a perfect blend of comfort and luxury, providing a refreshing escape right outside your door.

Whether you’re looking for a cozy retreat or a spacious family home, Osceola County’s real estate market has something for everyone. Dive into a lifestyle filled with sunshine, community spirit, and endless possibilities. Discover your dream home in Osceola County today, and experience the magic of Florida living at its finest!

Newest Osceola Homes with Pool Community Features

$469,900
3 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 6 SubDv. ⋅ 34747 Zip Code
GORGEOUS 'ONCE UPON A LIME' 3 Bed 3 Bath COTTAGE with Additional Bonus Room at Margaritaville Resort Orlando! This AMAZING Two-Floor Home features an Open Concept Living and Dining Room with Ceiling Fan, a Kitchen with QUARTZ Countertops, Stainless Steel Appliances, Side By-Side Washer and Dryer and Abundant Natural Light. Each of the Three Bedrooms and Living Room has Ceiling Fans, One Bathroom has a Shower/Tub Combo. The Door from the Kitchen Leads you to a Beautiful Patio with Lounge Chairs and Gorgeous Landscaping, Palm Trees and Tropical Foliage. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES Furniture/Housewares Package with Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

8061 Lost Shaker Lane, Kissimmee
$529,900
3 Beds ⋅ 3 Baths ⋅ Twin Lakes Ph 2a-2b SubDv. ⋅ 34772 Zip Code
NEW 4-TON A/C | WHOLE-HOUSE GENERAC GENERATOR | WATER SOFTENER SYSTEM | FRESH EXTERIOR PAINT | PREMIUM 70-FOOT LOT Why wait to build when this exceptional Marco model is already loaded with tens of thousands of dollars in upgrades? Situated on a premium 70-foot lot in the highly sought-after Twin Lakes by Del Webb, this move-in-ready home offers 3 bedrooms, including 2 private primary suites, 3 full bathrooms, and a dedicated office/flex room. Designed for both comfort and entertaining, the open-concept floor plan features soaring ceilings, 8-foot doors, abundant natural light, designer lighting, and upgraded quartz countertops throughout. The gourmet Bistro kitchen boasts white cabinetry with crown molding, a gas cooktop, upgraded stainless steel appliances, newer refrigerator, oversized island with seating for six, and a spacious pantry. The primary suite offers a relaxing retreat with a sitting area, large walk-in closet, and an updated bath featuring a new frameless glass shower enclosure. Additional upgrades include a new high-efficiency 4-ton A/C system, whole-house Generac generator, water softener system, fresh interior and exterior paint, ultra-quiet garage door opener, plantation shutters throughout, widened paver driveway, expansive screened lanai with extended paver patio, tankless gas water heater, professional landscaping with fresh mulch, and a spacious laundry room with cabinetry and utility sink. The low HOA includes lawn care, shrub maintenance, mulch, sod, and irrigation. Residents enjoy resort-style amenities including a beach-entry pool, lap pool, hot tub, 20,000-square-foot clubhouse, 24-hour fitness center with sauna, coffee bar, craft room, chef's kitchen, tennis, pickleball, putting green, walking trails, fishing, and resident-use pontoon and Jon boats. Exciting community enhancements are underway, including additional pickleball courts (expanding to seven total), a pool bar and plaza, event lawn and stage, food truck area, bocce ball, and cornhole. Conveniently located near Lake Nona Medical City, Orlando International Airport, world-famous attractions, beaches, and the Space Coast, this beautifully upgraded home is one of the best values currently available in Twin Lakes. Schedule your private showing today.

2606 Meadowedge Loop, St Cloud
$350,000
3 Beds ⋅ 3 Baths ⋅ Hub At Westside SubDv. ⋅ 34747 Zip Code
Welcome to 3357 Tranquil Trail, Kissimmee, FL, a beautifully maintained townhome in one of Central Florida’s most desirable locations. Situated just minutes from ChampionsGate, Four Corners, and the vibrant US 192 corridor, you’ll enjoy endless shopping, dining, and entertainment options. Walt Disney World and other world-famous attractions are only a short drive away. Located within a gated community, the property offers a secure and welcoming environment for residents and guests alike. Resort-style amenities make it ideal for both full-time living and vacation stays. Its prime location and strong rental demand create an outstanding opportunity for Airbnb or short-term rental investors.

3357 Tranquil Trail, Kissimmee
$654,900
7 Beds ⋅ 6 Baths ⋅ Emerald Island Resort Ph 4 SubDv. ⋅ 34747 Zip Code
Turnkey short-term rental home, minutes to Disney! Discover a rare opportunity to own this stunning 7 bedroom, 6 bathroom pool home in the sought after Emerald Island Resort. Boasting the largest layout in the community at 3,667 sq. ft., this home is perfectly suited as a vacation getaway, income-generating investment, or forever family home. Enjoy unparalleled waterfront views framed by lush wooded backdrops, creating a serene and private retreat. The expansive screened lanai, which spans the length of the house, features a partially covered area ideal for year round entertaining. Relax by the sparkling South facing private pool and spa and take in the ultimate Florida lifestyle. Step inside to find a well designed floor plan with ample living space, ideal for families or hosting guests. The stylish kitchen is a chef’s dream with abundant cabinet and countertop space, a breakfast bar, and a breakfast nook overlooking the huge living room and pool, your new favorite spot for morning coffee or casual dining. The main floor also features two bedrooms, a formal dining room and the charming “Harry Potter” closet for extra fun and storage. The upper level is thoughtfully divided by two staircases. One leads to a loft sitting area and three themed bedrooms and the other leads to two additional themed bedrooms, all designed for comfort, as five of the bedrooms feature en-suite bathrooms, while the remaining two share a convenient Jack and Jill bath. The 3 car garage has been transformed into an entertainment haven with air conditioning, complete with a mini movie theatre (seating for 8) and a game room with a pool table. Updates include: A brand new roof (11/24), a new pool heater (04/24), newer exterior paint (01/22) and a newer A/C and heat pump (11/20), replumbed A/C lines (2024) and spa actuators replaced (2024). As part of this premier gated community, you’ll enjoy access to an impressive clubhouse with a resort-style pool, Tiki bar, fitness center, sauna, and sundry shop. Other amenities include tennis and pickleball courts, volleyball, basketball, bike rentals, and 11 acres of natural walking trails. The prime location is conveniently located near Orlando’s major attractions, including theme parks, outlet shopping, restaurants, Promenade at Sunset Walk, and Island H2O Live! water park. This home comes fully furnished and equipped with a strong rental history, ready to generate income as a short term rental or provide your family with a wonderful retreat. Schedule your tour today and experience the ultimate Florida lifestyle in this stunning property.

8557 La Isla Drive, Kissimmee
$4,495,000
4 Beds ⋅ 4 Baths ⋅ Celebration Village Unit 2 SubDv. ⋅ 34747 Zip Code
Welcome to Crescentwood, a truly rare offering in the Main Village of Celebration, a fully reimagined estate set across two homesites, creating a scale and presence seldom found within the community. Thoughtfully renovated with high-end materials and custom finishes throughout, the residence blends timeless architecture with modern luxury in a way that is both refined and highly livable. As you enter, the foyer welcomes you with substantial millwork, curated lighting, and a level of craftsmanship that immediately defines the residence. Formal and casual living spaces are elegantly proportioned, featuring beautiful tile flooring, layered ceiling details with integrated lighting, custom built-ins, French doors and oversized windows that fill the interiors with natural light. A beautiful sitting room framed by eight windows creates an inviting space bathed in natural light throughout the day. At the center of the home, the completely redesigned chef’s kitchen showcases custom Poggenpohl cabinetry, premium integrated appliances, dramatic illuminated stone surfaces, extensive preparation space, and a seamless connection to the adjacent living and dining areas, creating an ideal setting for both entertaining and everyday living. The owner’s suite serves as a luxurious private retreat with a spa-inspired bath finished in striking marble, custom fixtures, and refined architectural detailing. The suite is further enhanced by two walk-in closets, offering exceptional organization and boutique-style functionality. Each secondary bedroom are designed as private ensuite retreats complete with walk-in closets and beautifully updated bathrooms featuring elevated finishes and distinctive design details. The third-story movie room offers a true cinematic experience tucked away as a private entertainment space. Adding to the property’s versatility is a fully upgraded one-bedroom apartment featuring a private entrance, luxurious bath with a freestanding tub and separate shower, eat in space, living room and full-size washer and dryer offering ideal flexibility for guests, extended family or private office space. The main residence includes a two-car garage, while automotive enthusiasts and collectors will especially appreciate the separate temperature controlled oversized three-car garage. Designed with high ceiling height to accommodate vehicle lifts, the space has the potential to house up to six vehicles—an extraordinarily rare amenity within Celebration. The outdoor living experience is equally impressive, featuring a swimming pool and spa surrounded by elegant limestone pavers, summer kitchen, covered entertaining areas, and lush landscaping. A substantial stucco masonry wall encloses the grounds, creating an ultra-private backyard and pool setting rarely found within Celebration’s Main Village. Extensive landscape lighting beautifully illuminates the property and architectural details in the evening, enhancing the estate’s ambiance and presence after sunset. Multiple outdoor gathering spaces further elevate the estate-like atmosphere, creating the feel of a private luxury resort. Crescentwood represents a one-of-one opportunity within Celebration, offering the rarity of a double homesite, a fully renovated luxury residence and a level of finish and scale that is nearly impossible to replicate within the Main Village.

706 Golfpark Drive, Celebration
$650,000
5 Beds ⋅ 4 Baths ⋅ Amelia Groves Ph 2 SubDv. ⋅ 34771 Zip Code
Perfectly positioned in the desirable Amelia Groves community, this stunning 5-bedroom, 4-bathroom Pulte Ashby Grand offers over 3,300 square feet of thoughtfully designed living space with modern finishes, peaceful wooded views, and no rear neighbors. Built in 2025, this move-in ready home combines contemporary style with exceptional functionality. The open-concept floor plan is filled with natural light and features expansive sliding glass doors that seamlessly connect the living area to the oversized covered lanai, creating the perfect indoor-outdoor living experience while showcasing the private backyard and tranquil wooded backdrop. At the heart of the home, the chef-inspired kitchen is designed to impress with quartz countertops, a large center island with seating, stainless steel appliances, built-in wall oven and microwave, subway tile backsplash, abundant cabinetry, a walk-in pantry, and stylish pendant lighting. The spacious living and dining areas provide an ideal setting for both everyday living and entertaining. The thoughtfully designed split floor plan offers privacy for the luxurious primary suite, complete with tray ceilings, generous space for a sitting area, oversized walk-in closet, and a spa-like ensuite featuring dual vanities, quartz countertops, an oversized walk-in shower with upgraded tile, and a private water closet. Three additional bedrooms are conveniently located on the first floor, including one with its own ensuite bathroom, making it perfect for guests or multigenerational living. Upstairs, you'll find an expansive loft, additional bedroom, and full bathroom, offering endless possibilities for a media room, game room, home office, fitness space, playroom, or private guest retreat. Step outside to enjoy the oversized covered lanai overlooking the private backyard and peaceful wooded views with no rear neighbors, creating the perfect setting to relax, entertain, or enjoy Florida's beautiful weather year-round. Additional highlights include wood-look tile flooring throughout the main living areas, plush carpeting upstairs, recessed lighting, modern fixtures, a spacious laundry room, and a 3-car garage offering plenty of room for vehicles, storage, or hobbies. Residents of Amelia Groves enjoy outstanding community amenities, including a sparkling pool with cabana, playground, scenic walking trails, and open green spaces, providing plenty of opportunities for recreation, relaxation, and outdoor enjoyment. Located in the sought-after Amelia Groves community, residents also enjoy convenient access to top-rated schools, shopping, dining, Lake Nona Medical City, Orlando International Airport, major highways, and Central Florida attractions. This beautifully maintained home offers the perfect combination of luxury, comfort, privacy, and convenience.

6035 Blue View Way, St Cloud
$515,000
2 Beds ⋅ 2 Baths ⋅ Mirasol At Celebration Condo SubDv. ⋅ 34747 Zip Code
The best homes don't just offer a place to live—they offer a lifestyle. Welcome to this beautifully maintained third-floor condominium in the highly sought-after Mirasol at Celebration, where elegant living meets the timeless charm of one of Central Florida's most iconic communities. With 2 bedrooms, 2 bathrooms, and the convenience of elevator access, this residence offers the perfect blend of comfort, sophistication, and low-maintenance living. Step inside to an inviting open-concept floor plan where rich wood flooring flows throughout the main living areas, creating a warm and refined atmosphere. At the heart of the home, the beautifully appointed kitchen features gleaming quartz countertops, stainless steel appliances, a spacious eat-in dining area, and a built-in desk—perfect for working from home, meal planning, or keeping everyday life organized. The thoughtfully designed split-bedroom floor plan provides privacy for owners and guests alike, while plush carpeting adds warmth and comfort to each bedroom. The spacious primary suite serves as a peaceful retreat, complete with an oversized walk-in closet and a spa-inspired ensuite bath featuring a double sink vanity, relaxing garden tub, and separate walk-in shower. Beyond your front door, Mirasol offers an impressive collection of resort-style amenities designed to complement your lifestyle. Residents enjoy a heated swimming pool and spa, a 24-hour fitness center, an on-site day spa and salon, a resident clubroom with billiards, a library, business center with conference room, cyber café, concierge service, and beautifully maintained grounds—all just moments from Celebration's charming downtown. From morning walks along Celebration's scenic trails to evenings spent dining at award-winning restaurants, browsing boutique shops, or attending one of the community's many events, every day feels like a getaway. Conveniently located just minutes from Walt Disney World, Orlando International Airport, and major highways, this exceptional residence offers the perfect balance of tranquility, accessibility, and luxury. Whether you're searching for a full-time residence, a seasonal retreat, or a place to simply enjoy life at a slower pace, this exceptional condominium delivers the Celebration lifestyle you've been waiting for. Welcome home to Mirasol at Celebration—where luxury, convenience, and community come together beautifully.

501 Mirasol Circle Unit 313, Celebration
$529,990
4 Beds ⋅ 4 Baths ⋅ Waterlin 45'S SubDv. ⋅ 34772 Zip Code
Virtually Staged. Under Construction. The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering five bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully positioned for privacy. An additional bedroom and a flexible bonus room on the second floor provide ample space for everyone. Sample Image

224 Cypress Fork Trail, St Cloud
$849,999
3 Beds ⋅ 3 Baths ⋅ Celebration South Village Unit 5 SubDv. ⋅ 34747 Zip Code
Welcome to this beautifully appointed David Weekley “Arabella” Craftsman, ideally situated on a quiet, tree-lined cul-de-sac and nestled against a peaceful conservation setting. A charming covered front porch and distinctive ribbon driveway create an inviting first impression, while a decorative mosaic medallion in the entryway adds an elegant custom touch. Inside, the bright and airy floor plan is filled with abundant natural light and thoughtfully designed for both everyday living and entertaining. Luxury vinyl plank flooring flows throughout the main living areas, while an electric fireplace creates a warm and inviting focal point in the spacious great room. The adjoining sunroom offers a wonderful additional living space, perfect for morning coffee, reading, or enjoying the tranquil surroundings. The updated kitchen features granite countertops, a convenient bar-height countertop for casual dining and entertaining, and all-new appliances. The formal dining room, kitchen, and bathrooms feature new light fixtures, adding fresh finishing touch throughout the home. A versatile office/flex room provides additional space for a home office, study, or hobby room. Upstairs, all three bedrooms provide privacy and comfort, along with a charming open balcony overlooking the great room below, creating a dramatic sense of space and architectural character. The primary suite features newly installed ceramic tile and a spacious walk-in closet, while the third bedroom also includes a walk-in closet. New carpeting throughout the second floor completes the fresh, updated feel. Outside, the large conservation lot offers a peaceful backdrop and generous backyard space. The covered front porch provides the perfect spot to relax and enjoy the quiet surroundings. Recent improvements provide added peace of mind, including fresh paint completed in December, a roof approximately five years old with gutters, and a 2017 water heater. An oversized 2½-car garage provides exceptional flexibility for vehicles, storage, hobbies, or additional workspace. With its classic Craftsman architecture, elegant custom details, extensive updates, inviting sunroom, open upstairs balcony, generous storage, oversized garage, and serene conservation setting, this exceptional Arabella offers a blend of timeless charm, contemporary comfort, and everyday Florida living.

1103 Banks Rose Court, Celebration
$455,000
3 Beds ⋅ 2 Baths ⋅ Del Webb Sunbridge Ph 2a SubDv. ⋅ 34771 Zip Code
Why wait to build when this like-new waterfront Hallmark home in Del Webb Sunbridge already offers panoramic pond views, completed upgrades and an exceptional move-in-ready Florida lifestyle? Located in St. Cloud’s premier gated 55+ active-adult community, this beautifully maintained, single-story home features the highly desirable HALLMARK FLOOR PLAN—NO LONGER OFFERED FOR NEW CONSTRUCTION in Del Webb Sunbridge. Built in 2023, it offers approximately 1,650 square feet with three bedrooms, two full bathrooms and a two-car garage—giving buyers the benefits of newer construction without the wait or added expense of completing major improvements after closing. The light-filled, open-concept floor plan seamlessly connects the kitchen, dining and gathering areas for comfortable everyday living and entertaining. The kitchen features quartz countertops, stainless-steel appliances, a natural-gas cooktop, built in oven and microwaves, pull-out cabinetry and a custom pantry with built-in shelving. Tile flooring flows throughout the entire home with no carpet, while a custom credenza and tinted-glass front door add style and functionality. Privately positioned at the rear of the home, the primary suite enjoys peaceful water views, a custom-designed walk-in closet and an upgraded walk-in shower with a built-in bench. Two secondary bedrooms are thoughtfully located away from the primary suite near the second full bathroom, creating excellent privacy and flexibility for overnight guests, hobbies or a home office. The true showpiece is the OVERSIZED SCREENED LANAI with an extended paver patio and PANORAMIC WATER VIEWS. Already PRE-PLUMBED FOR A FUTURE SUMMER KITCHEN, this exceptional outdoor living space is ready for sunset cocktails, relaxed mornings and year-round entertaining. Additional upgrades include a spacious laundry room with added cabinetry, generous storage and a utility sink; a salt-free water-softening system; natural gas servicing the tankless water heater and dryer; an epoxy-coated garage floor; and an insulated garage door. DEL WEBB SUNBRIDGE IS A GATED 55+ ACTIVE-ADULT COMMUNITY centered around the 27,000-square-foot Hammock Club, offering resort-style pools, a heated spa, fitness center, pickleball and tennis courts, walking trails, dog park, Tavern & Grille, resident clubs and a full social calendar. All outdoor yard maintenance and internet service are included for a convenient, low-maintenance lifestyle. Ideally located near Lake Nona, Orlando International Airport, Brightline and routes to Port Canaveral, this is the perfect lock-and-leave home base for enjoying Florida, traveling and staying close to family.

2499 Cliff Way, St Cloud
$485,000
4 Beds ⋅ 3 Baths ⋅ Storey Creek 40s SubDv. ⋅ 34746 Zip Code
Welcome to 1952 Rock Maple Bend, Kissimmee, FL, a beautifully maintained home featuring a spacious and thoughtfully designed floor plan for comfortable Florida living. The open-concept layout seamlessly connects the living room, dining area, and modern kitchen, creating an inviting space for everyday living and entertaining. The private primary suite includes a well-appointed bathroom and a generous walk-in closet, while the additional bedrooms provide flexibility for family, guests, or a home office. Large windows bring in abundant natural light, creating a bright and welcoming atmosphere throughout the home. Located in a desirable community, residents enjoy exceptional amenities including a resort-style swimming pool, clubhouse, playground, walking trails, parks, and beautifully maintained common areas. The convenient Kissimmee location provides easy access to shopping, restaurants, schools, healthcare facilities, and Central Florida's renowned attractions, including Walt Disney World Resort. Nearby major highways such as US-192, US-17/92, and Florida's Turnpike make commuting to Orlando, Lake Nona, and surrounding areas simple and convenient. The application process is easy and straightforward, making it simple to take the next step toward making this beautiful property your new home.

1952 Rock Maple Bend, Kissimmee
$330,000
3 Beds ⋅ 3 Baths ⋅ Hub At Westside Reserve SubDv. ⋅ 34747 Zip Code
Welcome to 3239 Sustainable Way, Kissimmee, FL, a beautiful home featuring a spacious and modern floor plan designed for comfortable Florida living. This residence offers an open-concept layout with a bright living area, a well-appointed kitchen with modern finishes, a dining space, and comfortable bedrooms designed for relaxation and privacy. The primary suite provides a peaceful retreat with a private bathroom, while additional bedrooms create flexibility for family members, guests, or a home office. The thoughtfully designed floor plan provides a great combination of functionality, style, and everyday convenience. Located in a desirable Kissimmee community, residents enjoy excellent amenities including a resort-style pool, clubhouse, playground, fitness center, walking trails, and recreational spaces. The community’s prime location provides easy access to shopping, restaurants, schools, healthcare facilities, and Central Florida’s famous theme parks and attractions. With convenient access to major highways, traveling to Orlando, Lake Nona, and surrounding areas is quick and convenient. The application process is simple and straightforward, making it easy to take the next step toward making this wonderful property your new home.

3239 Sustainable Way, Kissimmee
Start Your Search