Kissimmee Homes with Pool View

Kissimmee Homes with Pool View

Welcome to Kissimmee, Florida – a vibrant city that perfectly blends the excitement of theme parks with the charm of a close-knit community. Nestled in Osceola County, Kissimmee is renowned for its beautiful weather, making it an ideal destination for outdoor enthusiasts and families alike. With its proximity to world-famous attractions like Walt Disney World and Universal Studios, residents enjoy a lifestyle filled with adventure and entertainment.

One of the standout features of Kissimmee's real estate market is the abundance of homes with stunning pool views. Imagine waking up each morning to the serene sight of shimmering water right from your backyard. These properties not only offer a refreshing escape from the Florida heat but also provide a perfect setting for entertaining friends and family. Whether you're hosting a summer barbecue or simply enjoying a quiet evening under the stars, a home with a pool view elevates your living experience.

Kissimmee's neighborhoods boast a variety of architectural styles, from charming single-family homes to luxurious villas, ensuring there's something for everyone. Many of these residences are located within gated communities, offering added security and amenities such as clubhouses, fitness centers, and recreational areas.

Living in Kissimmee means embracing a lifestyle that balances relaxation and excitement. With its beautiful homes featuring pool views, this enchanting city invites you to create lasting memories in a picturesque setting. Discover your dream home in Kissimmee today, where sunshine and serenity await!

Newest Kissimmee Homes with Pool View

4 Beds ⋅ 2 Baths ⋅ Remington Prcl M1 SubDv. ⋅ 34744 Zip Code

Virtually Staged. Welcome to this beautiful 4-bedroom, 2-bath POOL home located in the highly sought-after Windsor Park neighborhood within the gated Remington Golf & Country Club community. Perfectly positioned on a scenic pond-front homesite, this move-in-ready residence offers the ideal blend of comfort, convenience, and Florida lifestyle living. Step inside to an open and airy floor plan featuring stylish laminate flooring, abundant natural light, and spacious living areas designed for both everyday living and entertaining. The well-appointed kitchen overlooks the living and dining spaces, creating a seamless flow for gatherings with family and friends. Sliding glass doors open to your private screened-in pool and lanai, where you can relax and enjoy tranquil pond views year-round. The spacious primary suite offers a walk-in closet and an upgraded ensuite bathroom, while the additional bedrooms are generously sized with ample closet space and ceiling fans throughout. Whether you're searching for a primary residence, vacation home, or income-producing property, this home offers exceptional flexibility with zoning that allows short-term rentals. Lawn care is included in the HOA dues, and the CDD is conveniently included in the annual property tax bill. Residents of Remington enjoy an impressive array of amenities, including a clubhouse, fitness center, recreation room, lap pool, kiddie pool, playground, tennis courts, basketball courts, beach volleyball, baseball and soccer fields, walking trails, and access to the community's beautiful golf course setting. Conveniently located near major highways, shopping, dining, schools, Orlando International Airport, world-famous theme parks, and Central Florida attractions, this exceptional home offers the perfect opportunity to enjoy resort-style living in one of Kissimmee's most desirable golf communities. Come experience the best of Florida living—your private pool retreat awaits

2747 Callaway Lane, Kissimmee

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

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

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

4 Beds ⋅ 3 Baths ⋅ Pennyroyal SubDv. ⋅ 34744 Zip Code

A truly distinctive residence where thoughtful design, craftsmanship, and sophisticated finishes come together to create a home unlike the ordinary. Extensively remodeled with exceptional attention to detail, this property showcases a warm contemporary aesthetic carried throughout with natural wood elements, designer lighting, custom accent walls, modern fixtures, and carefully selected finishes. Nearly every room reveals an unexpected architectural or design element, resulting in a level of customization rarely found in comparable homes. At the heart of the home is a truly exceptional chef-inspired kitchen where custom design and functionality come together beautifully. Calacatta quartz countertops, a generous center island, a sophisticated combination of crisp white and natural wood cabinetry, floor-to-ceiling storage, integrated appliances, designer lighting, geometric backsplash, pot filler, and thoughtfully incorporated accent lighting create a space that feels completely custom. A dedicated coffee station with floating wood shelving and a beverage/wine refrigerator adds another distinctive touch. The adjacent dining area continues the custom concept with a built-in dining island/table designed as an integral part of the space, creating a unique setting for everyday dining and entertaining. The Great Room is a showpiece of its own, featuring exposed wood beams, an impressive fireplace feature wall accented with stone and integrated wood storage, and a striking custom glass-enclosed wine display with warm wood detailing. Together, these architectural elements create a sophisticated yet inviting setting designed for both everyday living and entertaining. Even the staircase becomes part of the home's design, combining natural wood with contemporary black metal railings and distinctive lighting. The creativity continues into the bedrooms. One secondary bedroom features a one-of-a-kind custom built-in bunk/loft system with an integrated desk, shelving, and climbing features, creating an imaginative and highly functional space. The primary suite offers its own distinctive character with warm wood detailing and a fireplace feature, creating a relaxing private retreat. The bathrooms are equally impressive, with spa-inspired finishes including dramatic tilework, vessel sinks, contemporary black fixtures, frameless glass showers, custom vanities, illuminated mirrors, warm wood accents, and a freestanding soaking tub in the primary bath. Every space has been thoughtfully incorporated into the home's overall design rather than treated as an afterthought. Step outside and discover a private backyard oasis centered around a beautiful pool and spa completed in 2025. Its contemporary design, water features, integrated spa, generous paver decking, and multiple areas for relaxing and entertaining create a resort-inspired setting right at home. A covered patio extends the living space outdoors and provides the perfect place to enjoy the Florida lifestyle throughout the year. Solar panels provide an additional energy-conscious feature. From its highly customized interiors to its private outdoor retreat, this is far more than a typical remodeled home it is a residence transformed with creativity, personality, craftsmanship, and an extraordinary level of detail. This is a home that truly needs to be experienced in person to appreciate everything that makes it special. Furnishings may be available for purchase separately

1582 Sepal Street, Kissimmee

3 Beds ⋅ 3 Baths ⋅ Bvl Unit 9 5th Add SubDv. ⋅ 34743 Zip Code

Welcome to 412 Everwood Dr! a beautiful pool home offering the perfect combination of comfort, privacy, and Florida living with NO HOA and NO CDD! Whether you’re looking for your next home or a great investment opportunity, this property has so much to offer. Enjoy a remodeled kitchen, spacious primary bedroom with walk-in closet, and a large covered back terrace overlooking the pool and peaceful pond view the perfect setting for BBQs, entertaining, or simply relaxing at the end of the day. The fully fenced backyard adds privacy, while two driveways provide additional parking and convenience. Major improvements include a 2021 roof, 2025 A/C, washer and dryer, garage door opener, and special exterior paint designed to help withstand Florida’s intense heat. With its private pool, pond view, outdoor entertaining space, updated features, and no HOA or CDD fees, this home checks all the boxes. Home Warranty INCLUDED! Buyer may receive up to $5,000 toward closing costs when financing through preferred lender. Don’t miss the opportunity to make it yours, schedule your showing today!

412 Everwood Drive, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Villa Sol Ph 1 Village 5 SubDv. ⋅ 34744 Zip Code

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

3 Beds ⋅ 2 Baths ⋅ Monterey Village Ph 1 Unit 1 SubDv. ⋅ 34743 Zip Code

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

3 Beds ⋅ 2 Baths ⋅ Oaks At Mill Run Unit 2 The SubDv. ⋅ 34744 Zip Code

Welcome to this well-maintained one-story home in the heart of Kissimmee! This beautiful property features 3 bedrooms, 2 bathrooms, a spacious kitchen, new roof, new plumbing, new fence, sold fully furnished and an attached 2-car garage. Best of all, there is no HOA. Situated on a large corner lot, the home offers a private indoor pool and a fully fenced backyard, perfect for entertaining, gardening, pets, or simply relaxing outdoors.Enjoy a great location close to a public park and community pool, with quick access to the Florida Turnpike. You're just minutes from SeaWorld, Universal Studios, CityWalk, Downtown Orlando, and many other Central Florida attractions. Don't miss this opportunity to own a wonderful home.

2808 Mill Run Boulevard, Kissimmee

6 Beds ⋅ 5 Baths ⋅ Acreage & Unrec SubDv. ⋅ 34744 Zip Code

Rare 6.46-Acre Waterfront Development Opportunity on East Lake Tohopekaliga An exceptional opportunity to acquire 6.46± acres of waterfront property in one of Central Florida's fastest-growing areas. This offering includes two parcels totaling approximately 6.46 acres, consisting of a 2.66-acre improved parcel and an adjacent 3.80-acre vacant parcel, providing incredible flexibility for investors, developers, builders, or those seeking a private waterfront estate. The improved parcel currently features multiple residential units that generate approximately $30,000 in annual rental income, with the opportunity to increase income by approximately $18,000 annually through leasing the remaining units. Generate cash flow while planning your future vision. The true value of this property lies in its land, location, and development potential. With expansive frontage, mature oak trees, and direct access to beautiful East Lake Tohopekaliga, this is a rare opportunity to create a luxury waterfront enclave or private family compound. Preliminary concepts may allow for multiple estate-sized homes with guest houses, subject to county approvals and buyer due diligence. Located just minutes from Lake Nona, Medical City, Orlando International Airport, major highways, shopping, and dining, properties of this size with waterfront acreage are becoming increasingly difficult to find. Property Highlights • 6.46± acres across two parcels • 2.66-acre improved parcel • 3.80-acre adjacent vacant parcel • Direct waterfront location on East Lake Tohopekaliga • Existing income-producing improvements • Approximately $30,000 annual rental income with additional upside • Excellent investment, redevelopment, or estate opportunity • Potential for future subdivision or luxury estate development (subject to county approval) • Minutes from Lake Nona, Medical City, Orlando International Airport, and major roadways Opportunities of this scale, location, and potential are exceptionally rare in Central Florida.

2690 E Lake Road, Kissimmee

2 Beds ⋅ 2 Baths ⋅ Rio Hills Townhomes SubDv. ⋅ 34743 Zip Code

Welcome to Rio Hills, a quaint, gated townhome community offering a peaceful residential feel and a low-maintenance lifestyle. This move-in ready 2-bedroom, 1.5-bathroom unit enjoys a premium location directly across from the community pool and clubhouse, tucked into an established neighborhood with an inviting local vibe.Enjoy ultimate peace of mind with massive, high-ticket structural and mechanical upgrades, including a New Roof (2025), New HVAC (2026), and a New Hot Water Heater (2026). THE INTERIOR:Step inside to find extensive modern updates, featuring freshly painted walls, sleek laminate flooring, and an open kitchen elevated by a custom-tiled backsplash. The functional first floor seamlessly connects the living room, kitchen, and a versatile dining/flex space, complete with a guest half-bath and direct access to the back patio. Upstairs serves as a quiet retreat, offering a restful primary suite, a full bathroom with a luxury walk-in shower (2024), and a comfortable secondary bedroom completely refreshed with a new ceiling and flooring (2025). COMMUNITY & PARKING:The HOA covers private gates, common area maintenance, and access to the pool and clubhouse. Parking is a breeze with your designated spot right in front of the unit (marked with the unit number), plus visitor parking conveniently located next to the pool (restrictions apply). PETS: Bring your furry friends! The community allows a maximum of 3 pets (restrictions apply). INVESTORS: Will love this stable, high-demand area—long-term renting is permitted with a 12-month minimum lease (no short-term rentals). THE LOCATION:Perfectly situated near local dining, shopping, top-rated schools, and major highways. You are just minutes away from Orlando's world-famous theme parks, attractions, and a short drive to Florida’s beautiful beaches.

344 Cervantes Drive, Kissimmee

4 Beds ⋅ 3 Baths ⋅ Heritage Run SubDv. ⋅ 34744 Zip Code

RARE 4-BED/2.5-BATH TOWNHOME WITH 2-CAR GARAGE & PREMIUM POOL VIEW! Welcome to Heritage Run, a premier guard-gated community offering resort-style living with an incredibly low HOA of just $158/month covering gated security, a resort pool, and a playground! This expansive 1,935 sq ft contemporary home offers the space of a single-family home with zero exterior maintenance. The bright, open-concept main floor features ceramic tile, a spacious kitchen with sleek granite countertops, and seamless entertaining space. Slide open the glass doors to your private, screened-in lanai to unwind with peaceful views looking right toward the community pool. Upstairs, the massive primary suite features a grand walk-in layout and soaking tub. Three additional large bedrooms offer total flexibility for family, a home office, or media room, right next to the convenient 2nd-floor laundry. Under 10 mins to the exploding NeoCity tech hub, with rapid access to the Turnpike and Osceola Pkwy. Strongest value in 34744!

1205 Teton Drive, Kissimmee

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