Osceola Homes with Pool View

Osceola Homes with Pool View

Welcome to Osceola County, Florida, a hidden gem that perfectly blends natural beauty with vibrant community living. Nestled in the heart of Central Florida, Osceola is renowned for its picturesque landscapes, rich history, and endless recreational opportunities. With attractions like the iconic Walt Disney World Resort and the stunning Kissimmee Lakefront Park, residents and visitors alike are never far from fun and adventure.

Osceola County is also home to a diverse range of neighborhoods, each offering unique charm and character. For those seeking the ultimate Florida lifestyle, homes with pool views are a quintessential feature in many of these communities. Imagine waking up each morning to the gentle sounds of water lapping against the shore, or enjoying a delightful evening under the stars with a stunning pool view right from your backyard.

Whether you’re looking for a cozy single-family home or a luxurious villa, Osceola County offers an array of properties that cater to all tastes and budgets. Many of these homes boast expansive outdoor spaces, perfect for entertaining friends and family or simply relaxing in the sun. With year-round warm weather, a pool view becomes not just a luxury, but a lifestyle choice that enhances your living experience.

Discover the magic of Osceola County and find your dream home with a pool view today. Embrace the Florida sunshine and create lasting memories in a community that feels like home. Your paradise awaits!

Newest Osceola Homes with Pool View

5 Beds ⋅ 5 Baths ⋅ S5155801 MLS

Welcome to the GATED COMMUNITY of LINDFIELDS RESERVE, ideally located just MINUTES from both the FRONT and BACK GATES of WALT DISNEY WORLD! Enjoy EASY ACCESS to major roadways including US-192, HWY 27, 429, and I-4, connecting you to everything CENTRAL FLORIDA has to offer—from MARGARITAVILLE RESORT ORLANDO and SUNSET WALK to countless RESTAURANTS, SHOPS, and ATTRACTIONS. The ASSOCIATION FEE offers EXCEPTIONAL VALUE and includes WEEKLY POOL MAINTENANCE, MOWING OF ALL GRASSES, WATERING OF ALL LAWNS, HIGH-SPEED INTERNET, BASIC CABLE TV THROUGH BRIGHTHOUSE, EXTERIOR PAINTING EVERY 10 YEARS, AUTOMATIC GATE MAINTENANCE, TENNIS COURT MAINTENANCE, STREET LIGHTING, LIABILITY INSURANCE FOR COMMON AREAS, and COMMON AREA TAXES. This COURTYARD-STYLE, 5-BEDROOM HOME is truly ONE-OF-A-KIND. Step through the elegant DOUBLE DOORS into your PRIVATE POOL and HOT TUB OASIS, surrounded by SLIDING GLASS DOORS that FULLY OPEN to create a seamless INDOOR/OUTDOOR LIVING EXPERIENCE. The POOL AREA has been BEAUTIFULLY RENOVATED, featuring a HIGH-END PEBBLETEC SURFACE, NEW WATERLINE TILE, a MARBLE SLAB beneath the JACUZZI FOUNTAIN, and UPGRADED HEATING EQUIPMENT. Major updates continue with a BRAND-NEW 50-GALLON ELECTRIC WATER HEATER installed in JULY 2026 with a 5-YEAR WARRANTY. All EXTERIOR LANTERNS have been REPLACED and MODERNIZED for a FRESH, WELCOMING GLOW. A TOP-OF-THE-LINE 24-GAUGE STANDING SEAM METAL ROOF was completed in JULY 2020, providing both DURABILITY and STYLE. The KITCHEN underwent a COMPLETE RENOVATION in 2021, showcasing EXTENDED PACIFIC CARRARA CLOUD QUARTZ COUNTERTOPS, CUSTOM SOLID WOOD CAROLINA MAPLE OYSTER CABINETRY with SOFT-CLOSE DOORS, DESIGNER HARDWARE, GLASS SUBWAY TILE BACKSPLASH, a KARRAN QUARTZ SINK, ADDED DRAWER STORAGE, and a SPACIOUS BREAKFAST BAR. Stay comfortable year-round with DUAL HIGH-EFFICIENCY HVAC SYSTEMS (3-TON and 2-TON, 16 SEER). All five bedrooms feature LUXURY VINYL PLANK FLOORING in a PALE PEWTER FINISH, offering a CLEAN, MODERN LOOK with NO CARPET THROUGHOUT. Each of the FIVE ENSUITE BATHROOMS has been FULLY UPDATED, boasting BEAUTIFUL TILE WORK, TILE INLAYS, RE-GLAZED BATHTUBS, RESURFACED COUNTERTOPS, and MODERN LED LIGHT FIXTURES. That’s not all—this property also includes a PRIVATE IN-LAW SUITE complete with its own DINETTE and STAINLESS STEEL APPLIANCES, plus UPDATED CEILING FANS with LED LIGHTING throughout the home. For added PEACE OF MIND and CONVENIENCE, enjoy SMART HOME FEATURES including a NEST THERMOSTAT, NEST HELLO VIDEO DOORBELL, YALE KEYLESS ENTRY, and a COVE SECURITY SYSTEM integrated with SMOKE and CARBON MONOXIDE DETECTORS. Perfect as a PRIMARY RESIDENCE, VACATION HOME, or SHORT-TERM RENTAL INVESTMENT, this property is being sold TURN-KEY—FULLY FURNISHED, FULLY STOCKED, and BEAUTIFULLY DECORATED, right down to the LINENS. DON’T MISS YOUR CHANCE to own this EXCEPTIONAL HOME in an UNBEATABLE LOCATION. SCHEDULE YOUR PRIVATE SHOWING TODAY!

8807 Crayson Court, Kissimmee

5 Beds ⋅ 5 Baths ⋅ O6434446 MLS

Whether you're looking for an income-producing vacation rental or a personal retreat, this 5-bedroom, 5-bath home in the highly desirable gated community of Windsor Hills is an excellent opportunity. The kitchen is positioned at the front of the home and overlooks the formal dining area, creating a welcoming space for family meals and entertaining. The living room is located at the rear of the home and opens to the screened-in pool deck, offering a relaxing space to enjoy the Florida sunshine. Two bedrooms are conveniently located on the first floor, along with two of the bathrooms, while the remaining bedrooms and bathrooms are upstairs, providing comfort and privacy for guests. The garage has been converted into a fun games room with pool and foosball tables, adding extra appeal for renters. Windsor Hills is one of the closest resorts to Disney and features outstanding amenities, including a resort-style pool with water slides, clubhouse, fitness center, and sports courts. Ideal for short-term rental investment, second home, or full-time residence.

7795 Basnett Circle, Kissimmee

4 Beds ⋅ 3 Baths ⋅ TB8539232 MLS

Welcome to your private oasis in the highly desirable golf community of The Oaks! This beautifully upgraded 4-bedroom, 3-bath home features a spacious open floor plan plus a versatile bonus room that can easily serve as a 5th bedroom, home office, or guest suite. Designed for both everyday living and entertaining, the home features remodeled bathrooms, granite countertops, California Closets, crown molding, electric curtains, upgraded lighting, water softener and purification systems, and premium indoor/outdoor surround sound. Step outside to your own resort-style retreat featuring a screened and fenced heated saltwater pool and spa, cedarwood ceilings, shaded entertaining areas, mature landscaping, and plenty of backyard space. A circular driveway provides ample parking and adds to the home’s impressive curb appeal. The Oaks features an exceptional lifestyle with golf, access to Lake Toho, boating, fishing, tennis and basketball courts, playgrounds, and nature trails. Conveniently located near shopping, dining, schools, medical facilities, airports, theme parks, and all that Central Florida has to enjoy. A move-in-ready home where comfort, entertainment, and Florida living come together beautifully.

3034 Boating Boulevard, Kissimmee

3 Beds ⋅ 3 Baths ⋅ O6433073 MLS

Virtually Staged. Prepare to be amazed by this stunning country Homestead located on a quiet dead end city-maintained road. Situated on 2.44 acres of high and dry manicured land, this fully fenced property offers unparalleled privacy and space. The previous owners had horses on this property, and the current owner just added a no climb fence for their Frenchie’s. A concrete circular driveway warmly invites you to where you will notice the Ranch style home with a metal roof and screened in front porch. Step inside to a spacious, open concept floorplan. The updated kitchen features shaker cabinets with a lazy Susan, Crown molding, pull out bottom drawers, soft close drawers and doors, a built-in pantry with pull out shelves’ granite countertops, stainless appliances, including a GAS STOVE and a one of kind 70 x 76 cypress wood island. The living room is located just across from the dining area through the double French doors and features a brick, wood-burning fireplace, two ceiling fans, plant shelves and a sky light. The Primary suite includes a spa-like bathroom to include dual sinks, a walk-in shower, a gorgeous soaker tub, and 3 walk in closets, one of which is fairly large and could easily be transformed into an office or nursery. This split bedroom plan is great for privacy of the primary suite. Bedrooms 2 and 3 share a Jack and Jill bathroom. The laundry room is equipped with a brand-new dryer vent, shelves a laundry tub, and pull-down attic stairs for access to one of three attics for additional storage. A private half bath is perfect for guests. Out back is a 750 square feet enclosed Florida room where you can enter the home from your oversized 30 x 30 2 car garage with huge attic space, the Florida room has a 10 x 10 section (mud room) as you enter from the garage. This home also features an amazing, heated saltwater pool adorned with a rock waterfall. Watch beautiful sunsets over the large pond from 70x30 paver pool deck. The other great feature of this home is the 30'x30' metal building with THREE roll up doors the building has electricity and an outside water source, use it to store your favorite toys or as a workshop but it’s large enough to do both. You will absolutely LOVE the Southern Live Oak Tree between the pool and workshop. There are so many great features in this home such as lighted Niche’s, plant shelves, 14 foot ceilings in the great room, wainscotting, 5 ¼” baseboards, a large linen closet, Pass thru from the kitchen to the Florida room, a water softener, water filtration system, painted garage floor, Rain gutters, NO HOA but the huge pond beyond the property along with the trees and lawn are all maintained by a neighboring HOA. The location is fabulous, just down the street from the new High School, close to shopping, restaurants, an ER and a Walmart coming soon, plus you have easy access to major roads for access to Disney and all the area attractions plus Orlando’s International Airport. Y’all come on out and see this real soon before it’s gone.

1868 Druliner Road, St Cloud (Magnolia Square)

4 Beds ⋅ 3 Baths ⋅ S5155340 MLS

Welcome to 2791 Picadilly Circle, Kissimmee, FL — a beautifully updated 4-bedroom, 2.5-bath pool home offering the perfect combination of modern upgrades, generous living space, privacy, and the Florida lifestyle. From the moment you step inside, you’ll appreciate the bright, open floor plan and thoughtfully upgraded interior. At the heart of the home is the updated gourmet kitchen, designed to impress with stylish finishes and an inviting layout perfect for everything from everyday meals to entertaining family and friends. The bathrooms have also been tastefully updated and upgraded, giving the home a fresh, modern feel throughout. With four spacious bedrooms and 2.5 baths, there’s plenty of room to spread out. The versatile living areas provide flexibility for entertaining, working from home, family gatherings, or simply relaxing at the end of the day. Step outside and discover your own private Florida retreat. The fully fenced backyard features a sparkling swimming pool and plenty of space to relax, entertain, barbecue, or soak up the Florida sunshine. Whether hosting weekend gatherings or enjoying a quiet afternoon poolside, this outdoor space is designed to be enjoyed year-round. Conveniently located in the heart of Kissimmee, 2791 Picadilly Circle puts you just minutes from shopping, dining, schools, major roadways, Orlando-area attractions, and everything Central Florida has to offer. Updated gourmet kitchen. Upgraded bathrooms. Four spacious bedrooms. Private fenced backyard. Sparkling pool. Prime Kissimmee location. This home checks all the boxes and is ready for its next owner. Schedule your private showing today and experience everything 2791 Picadilly Circle has to offer!

2791 Picadilly Circle, Kissimmee

4 Beds ⋅ 4 Baths ⋅ S5155317 MLS

Step inside the foyer and experience a light-filled, open floor plan designed for effortless living and entertaining. The expansive family room flows seamlessly into the gourmet kitchen, featuring stainless steel appliances, quartz countertops, oversized cabinetry with abundant storage, and a cozy breakfast nook—perfect for morning coffee or casual dining. Elegant French doors open to your private backyard oasis, where the screened lanai offers plenty of room to relax in the shade, soak up the sun, or entertain guests poolside. The spacious primary suite provides a peaceful retreat, with room for a king-sized bed and a beautifully appointed ensuite featuring dual vanities, a step-in shower, and a relaxing soaking tub. Bedrooms two and three have generous space and walk-in closets, providing comfort and ample storage for family or guests. The property also features an attached, air-conditioned garage, plus an oversized detached garage with abundant storage and additional parking. Both garage doors are heavily insulated and have UV protective windows. Above the detached garage, you’ll find a versatile mother-in-law suite complete with a kitchenette, private bedroom, full bathroom, and walk-in closet—ideal for extended family, guests, a home office, or additional living space. Located in desirable Northshore, residents enjoy exclusive access to Lake Lizzie, part of the beautiful Alligator Chain of Lakes. With a private community dock and boat ramp, you’ll have endless opportunities for boating, fishing, and enjoying Florida’s waterfront lifestyle. This exceptional property offers the perfect combination of spacious living, resort-style outdoor enjoyment, versatile guest accommodations, and exclusive lake access—all in one incredible home.

1803 Charles Court, St Cloud (Magnolia Square)

4 Beds ⋅ 3 Baths ⋅ O6430008 MLS

Virtually Staged. SPANISH-MEDITERRANEAN WATERVIEW OASIS WITH PRIVATE IN-LAW SUITE Located in the gated community of Villa Sol, this 4 Bed / 3 Bath single-story residence (2,351 sq ft heated) features a private pool, spa, and direct pond views—plus a dedicated, attached in-law suite with its own exterior entry. PROPERTY HIGHLIGHTS: In-Law / Guest Suite: Private exterior back entrance, separate bedroom, and full bath. Outdoor Living: Screen-enclosed heated pool and integrated spa set on an oversized lot with peaceful water views. Chef’s Kitchen: Granite countertops, multi-level breakfast bar, stainless steel appliances, and pendant lighting. Primary Suite: Vaulted ceilings, luxury vinyl plank flooring, walk-in closet, direct pool access, and en-suite with a jetted soaking tub and dual-sink vanity. Interior Design: Open layout, vaulted ceilings, polished porcelain tile, and architectural archways. LOCATION & COMMUNITY VALUE: Low HOA ($160/mo): Includes high-speed fiber internet, cable TV, and ground maintenance. Resort Amenities: Gated entry, clubhouse, fitness center, resort pool, tennis & basketball courts, and playground. Prime Location: Fast access to SR-417, US-192, Lake Nona Medical City, and MCO Airport. Zoned for top local schools.

3133 Riachuelo Lane, Kissimmee

5 Beds ⋅ 2 Baths ⋅ O6431912 MLS

Welcome to 3605 Daydream Place—an opportunity that stands out in the low-HOA Esprit community! Tucked away on a cul-de-sac, this spacious 5-bedroom, 2-bath home offers 2,028 sq ft, a 2-car garage, .27-acre fully fenced lot AND your own heated saltwater pool—a combination that can be hard to find, especially at this price point. From the covered front porch and beautiful landscaping with concrete curbing to the brick pavers widening the driveway, this home makes a great first impression. Step inside to an inviting home filled with natural light and plenty of room to spread out. Easy-care ceramic 12x24 tiles flow throughout with no carpet anywhere, while blinds on every window and ceiling fans in all bedrooms, the living room and family room add everyday comfort. The floor plan offers both living and family rooms along with a smart bedroom layout. Three secondary bedrooms are grouped together down one hallway, while another bedroom is positioned at the front of the home, providing separation and flexibility as a guest room, home office or hobby space. The kitchen features stainless steel appliances, an island, ample cabinetry and an adjoining dining area. The generously sized primary bedroom provides a comfortable retreat with plenty of room for larger furniture. The ensuite bath features dual sinks, a garden tub and separate shower, while the huge walk-in closet provides an impressive amount of storage. The backyard is where this home truly delivers the Florida lifestyle. Step from the covered lanai into the screened enclosure and your own heated saltwater pool—perfect for morning swims, weekend gatherings or relaxing at the end of the day. There’s plenty of room for lounging and entertaining, while the fully fenced yard still offers additional green space. A convenient dog door adds to the pet-friendly setup, and the pool enclosure screens were replaced approximately two years ago. Even more value comes from major improvements include a 2022 roof, new A/C (2024) with Blue Light bacteria system added in 2025, fresh exterior paint in 2026 and paid-off solar panels—helping reduce monthly electric costs without the added expense of a solar loan or lease. The garage features an epoxy floor, pull-down attic access and wooden storage shelving that stays. Shopping, dining and everyday necessities are approximately 10 minutes away, with convenient access to the Florida Turnpike. Orlando International Airport is approximately 30–35 minutes away, with Walt Disney World and the Orlando theme park corridor roughly 35–45 minutes from home. Melbourne and the Atlantic beaches are approximately an hour away, making a beach day an easy getaway. With a private heated saltwater pool, oversized fenced lot, cul-de-sac location, low HOA, paid-off solar and several big-ticket improvements already completed, finding this much home and lifestyle at this price is an opportunity worth seeing in person. Don’t overlook everything 3605 Daydream Place has to offer—schedule your showing and come experience it for yourself!

3605 Daydream Place, St Cloud (Narcoossee Road)

3 Beds ⋅ 2 Baths ⋅ O6431242 MLS

At the end of a quiet cul-de-sac, you'll find something that's getting harder to come by... privacy. With no rear neighbors now or ever, the backyard feels like your own little escape. No backdoor neighbors. No one peeking over the fence. Just mature trees, peace and quiet. The screened pool and covered lanai make it easy to enjoy Florida year-round, whether it's coffee before work, jumping in the pool after a long day, or firing up the grill on the weekend. Inside, this beautifully updated 3-bedroom, 2-bath home feels fresh from the moment you walk in. Luxury vinyl plank flooring runs throughout, the kitchen has been completely updated with quartz countertops, stainless steel appliances, and modern finishes, and both bathrooms have been beautifully renovated. The split-bedroom floor plan gives the primary suite a little separation from the secondary bedrooms, while the open living and dining spaces feel bright, comfortable, and easy to live in. The super low HOA is just one more thing to appreciate, giving you the benefits of the neighborhood without the high monthly dues that have become so common. The location checks all the right boxes. You're about 15 minutes from The Loop, putting shopping, restaurants, and everyday errands close by, with easy access to Florida's Turnpike and Osceola Parkway for an easy commute. Walt Disney World, Universal Orlando, Lake Nona, Orlando International Airport, and countless other Central Florida destinations are all within easy reach. Close to everything. Far from the noise.

2346 Cordova Court, Kissimmee

4 Beds ⋅ 2 Baths ⋅ O6429805 MLS

Welcome to 1513 Indian Oaks Trail, a spacious 4-bedroom, 2-bath pool home offering a flexible floor plan, low HOA fees, and an excellent location near Central Florida’s world-famous attractions. The welcoming single-story exterior features a screened front entry, attached two-car garage, mature palm trees, low-maintenance landscaping, and a spacious driveway that creates inviting curb appeal. Inside, the open-concept living area features vaulted ceilings, tile flooring, recessed lighting, neutral finishes, and a seamless flow into the kitchen and screened outdoor living area. The bright dining space offers sliding glass doors that fill the room with natural light and provide convenient access to the lanai and pool. The kitchen features bright cabinetry, solid-surface countertops, stainless steel appliances, ample preparation space, an eat-in area, and a spacious breakfast bar overlooking the main living area. The primary bedroom offers wood-look flooring, neutral finishes, natural light, and convenient access to the private en-suite bathroom. The primary bath features a dual-sink vanity with abundant cabinet storage, an oversized mirror, tile flooring, a walk-in shower, and a large soaking tub positioned beneath a window. A spacious walk-in closet provides wraparound shelving, generous hanging space, and plenty of organized storage. Bedrooms two through four offer comfortable layouts, neutral finishes, natural light, and ample closet space. Two bedrooms feature wood-look flooring, while another includes carpeting and decorative chair-rail molding, creating flexible options for family, guests, or a home office. The updated second bathroom includes a tiled tub and shower combination with subway tile surround, a modern vanity, updated fixtures, and a window providing natural light. Step outside to an inviting covered and screened lanai, ideal for relaxing or entertaining. The screened-in pool features a safety fence, expansive pool deck, and privacy fencing, creating a private setting for enjoying Florida’s year-round sunshine. Located just minutes from Walt Disney World, with Universal Orlando, SeaWorld, and the attractions corridor within easy reach. Restaurants, grocery stores, shopping, and entertainment along US-192 are nearby, while convenient access to SR-429 and I-4 provides an easy connection to downtown Orlando and Orlando International Airport. The community offers a neighborhood pool, tennis court, playground, and park surrounded by mature shade trees. The neighborhood may also allow both short-term and long-term rentals, offering potential flexibility for a primary residence, vacation home, second home, or investment property. Buyers should independently verify all rental restrictions, zoning requirements, and permitting with the HOA and Osceola County. Schedule your private showing today!

1513 Indian Oaks Trail, Kissimmee

3 Beds ⋅ 2 Baths ⋅ O6430477 MLS ⋅ 7505 BLDG.

Experience effortless resort living in this beautifully updated, fully furnished 3-bedroom, 2-bathroom condo in the gated Reunion Resort community. Thoughtfully enhanced by the current owner, the residence features luxury vinyl flooring throughout, new appliances, updated fixtures, and a wine refrigerator, creating a stylish, move-in-ready retreat. Located in an elevator building, the condo also offers a private balcony, its own one-car garage, and a private driveway. Whether you're looking for a primary residence, second home, vacation getaway, or short-term rental opportunity, this property offers exceptional flexibility in one of Central Florida's premier resort communities. The Terraces at Reunion features a community pool, barbecue area, and park, while Reunion Resort offers an impressive collection of amenities, including three signature golf courses designed by Jack Nicklaus, Arnold Palmer, and Tom Watson, a multi-level water park, miniature golf, tennis, fitness and spa facilities, multiple community pools, and a variety of restaurants and dining options. Ideally located approximately 30 minutes from Orlando International Airport and just a short drive from Central Florida's world-famous theme parks and attractions, Reunion combines convenience with a true resort-style experience. With 24-hour gated access and a golf-cart-friendly setting, this turnkey, fully furnished residence offers the perfect opportunity to enjoy the Florida resort lifestyle from day one.

7505 Mourning Dove Circle Unit 303, Kissimmee

5 Beds ⋅ 5 Baths ⋅ O6430843 MLS ⋅ N/A BLDG.

Where else can you live in Florida feeling like you are on Vacation everyday?! Resort style pools, Lazy River, Water Playground, Fitness Center, Restaurant & Club House, Pond and Pier and so much more! Those are just the amenities; lets talk about this 5 Bedroom & 5 Bath with a private garage in paradise. You have enough space for the family and some including a theatre area for all to enjoy. Subtle taste of Disney throughout the home and a very nice size kitchen for all to gather. Don't want to stop the fun from the community pool? Well bring it home since you'll have your very own private pool and patio area to enjoy. Its spacious, its clean and comes completely furnished as you see it all you need is the key to make it yours. You can enjoy this home as little or as much as you'd like as short term rental is allowed as well as long term if you'd choose. Want the best of both worlds? Why not leave your vehicle stored in the garage and some personal items in your very own, owners closet's throughout the house. Having too many options is never a bad thing when you either way you are making the right choice. Schedule your next appointment today!

9025 Rhodes Street, Kissimmee

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