34744 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

$1,549,000

5 Beds ⋅ 4 Baths ⋅ Florida Fruit Belt Sls Co SubDv. ⋅ 34744 Zip Code

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

2745 Lloyd Lane, Kissimmee

$549,900

4 Beds ⋅ 2 Baths ⋅ Breckenridge SubDv. ⋅ 34744 Zip Code

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

1730 Kasey Court, Kissimmee

$520,000

4 Beds ⋅ 4 Baths ⋅ Somerset SubDv. ⋅ 34744 Zip Code

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

1017 Berkeley Drive, Kissimmee

$820,000

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

$499,900

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

$399,000

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

$1,938,000

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

$624,999

4 Beds ⋅ 3 Baths ⋅ Ashley Cove Unit Two SubDv. ⋅ 34744 Zip Code

Tucked Away Gated Estate Near Lake Toho & NeoCity – Luxury, Privacy & Strategic Location!Welcome to your private oasis outside the city limits! Nestled in a quiet, low-traffic enclave in the back of a highly desirable gated community, this stunning 4-bedroom, 3-full-bath estate spans 3,015 sq. ft. of pure luxury. Situated on a rare, oversized lot (approx. 1/3 to 1/2 acre) framed by a majestic canopy of mature oaks, this home offers unparalleled peace and privacy. While you are tucked away adjacent to the pastures and world-class bass fishing of Lake Tohopekaliga, you are strategically located just minutes from the Florida Turnpike entrance for an effortless commute to Orlando, and a short drive to NeoCity, Central Florida’s premier technology and innovation hub.The Interior:Pass through the grand entryway to discover soaring, very high ceilings and an abundance of natural light framed by elegant plantation shutters. The floor plan completely eliminates carpet, showcasing premium ceramic tile and luxury vinyl laminate flooring throughout. The gourmet kitchen and all three full baths feature gorgeous granite countertops. Retreat to the massive master suite, complete with a spa-like bath featuring a deep Jacuzzi soaking tub. Above the 3-car garage (which boasts a professionally finished floor), a versatile bonus room awaits—perfect for a private home office, media room, or guest suite.The Outdoor Oasis:Step through the sliders into your massive, fully screened pool lanai. The custom pool is a true tropical retreat, featuring an integrated spa with dual heating systems: gas heat for rapid spa warming and solar heat for eco-friendly, year-round pool enjoyment. The sprawling backyard offers total seclusion, bordered by a peaceful landscape that feels worlds away from the hustle and bustle.Mechanical Peace of Mind:Forget about hidden costs—this home is fully updated and built for efficiency:Newer RoofNewer HVAC (Still under warranty!)Newer Hot Water HeaterEnjoy the ultimate Central Florida lifestyle in a peaceful, low-traffic neighborhood, combining pastoral tranquility with immediate access to major highways and booming tech hubs. Schedule your private tour today!

1648 Marina Lake Drive, Kissimmee

$599,999

3 Beds ⋅ 2 Baths ⋅ Cane Brake Ph 2 SubDv. ⋅ 34744 Zip Code

Welcome to Paradise. This beautifully upgraded solid brick residence offers over $100,000 in premium improvements and the rare luxury of NO HOA, with conservation-area privacy and no rear neighbors. Enjoy a marble foyer and open layout, plus French doors with internal tilt blinds that open to a finished 24’ x 13’ climate controlled addition. The oversized 26’ x 16’ great room is ideal for entertaining. The expansive primary suite includes a dedicated office area, and all three bedrooms are generously sized and can fit king beds. Major updates include new windows and doors, a 2022 roof, and a 2017 A/C serviced annually. Step outside to a private 15’ x 30’ pool with a newly rescreened enclosure featuring 36" privacy kick plates, updated outdoor lighting, and a repainted pool deck, plus low-maintenance stone landscaping. The large backyard is perfect for gatherings and pets, with room for volleyball, wiffle ball, tossing a football, or hosting a barbecue or pool party. The backyard also includes a new 25’ x 30’ concrete pad and a 10’ x 20’ custom shed. Additional upgrades include new carpeting, Levolor blinds, new vinyl plank flooring in master bathroom, tinted windows, hurricane shutters, a hurricane-rated garage door, custom-color seamless gutters, and underground drainage. In the peaceful Cane Brake community, known for its quiet one-entrance design and long-term residents, this home offers exceptional comfort, privacy, and a serene atmosphere that feels like a private retreat. Schedule your showing today.

2220 Emperor Drive, Kissimmee

$315,900

3 Beds ⋅ 1 Baths ⋅ Dellwood Park SubDv. ⋅ 34744 Zip Code

Great price on this beautifully renovated home, updated just three years ago! A proven, well-maintained rental with excellent income potential, this solid block 3-bedroom, 1-bath home offers side-yard parking behind fencing plus EV (electric vehicle) hookups. Renovated throughout, the home features all 3-year old appliances, ceramic tile flooring, a fully updated kitchen with 42” soft-close cabinets and stunning quartz countertops, recessed lighting, ceiling fans, tankless water heater, updated plumbing and electrical, 5/8” drywall, doors, paint, and updated ductwork. A/C (2017) and maintained. Enjoy outdoor living with a large covered back porch overlooking a refinished in-ground pool (2019), outdoor shower, RV concrete pad with electric, water, and security lighting, and a roof with solar attic vent. Additional upgrades include hurricane-certified double-pane vinyl windows. Ideally located near downtown Kissimmee, close to Osceola Parkway for shopping, schools, parks, major attractions, and easy access to both East and West Coast beaches. Move-in ready and investment-friendly—this one won’t last!

103 Dellwood Drive, Kissimmee

$3,499,000

10 Beds ⋅ 8 Baths ⋅ Florida Fruit Belt Sales Co 1 SubDv. ⋅ 34744 Zip Code

Discover the epitome of equestrian luxury with this pristine 5.85-acre estate, featuring a state-of-the-art four-stall barn, premier riding ring, and a meticulously designed custom home and guest house. Strategically in Central Florida, just minutes from major roadways and an easy location to all the major horse shows and events Florida offers. Property also backs up to an 18-hole beautiful golf course, adding to the privacy of this property. This exceptional estate’s main residence boasts 8,261 sf of luxury living with seven bedrooms, five baths, all carefully renovated with designer selections. Gorgeous formal dining room can seat 12, ideal for those special holidays. An incredible chef’s kitchen features a bar-style center island, all opening to large gathering space, which features a gorgeous fireplace with custom-built mantle. The chef’s kitchen is home to updated stainless appliances, custom wood cabinetry, center island with sink and bar seating, granite counters, hidden pantry, double refrigerator and freezer, and generous counter space to spread out. The back of house has views from an incredible window and door bank, which allows beautiful ambient light through the house and overlooks the outdoor resort-style pool and entertaining area. This is the home your friends and family will gather in and want to stay! The home office or flex room is designed for a golf simulator, so practice your game while taking those work calls. As you go outside, an outdoor paradise awaits, where the pool takes center stage for a staycation at home with a lazy river, spa, pool cabana and firepit, and deck that wraps the pool, providing plenty of space for a large crowd. The covered lanai extends across the back and includes a fully appointed summer kitchen with room for alfresco dining space to soak in the Florida weather. Primary suite with spa-like bath, which includes dual vanities, steam station of clothing, makeup vanity, double head shower, jetted tub and built-in jewelry cabinet. Two of the seven bedrooms are upstairs with great landing area. Home has terrific storage and every detail accounted for. The equestrian amenities are designed for horse lovers and include four stables, a tack room, sliding doors on three sides, an incredible 1,800-square-foot garage with roll-up doors for ease of parking your vehicles and toys, as well as a Tesla charger. A 1,324-square-foot porte-cochere connects the main house to guest house. Guest house or in-law suite is 1,620 square feet, three bedrooms and two baths, providing privacy for all. The function of this property is designed for the serious equestrian in a serene location while being close to a city lifestyle. Other features of the unique property include whole-house generator (Generac), inside laundry organization center with pet washing area, plantation shutters, Icynene insulation, irrigation (not in pastures), crown molding and chair rail, central vacuum system, in-floor outlets, tankless water heater, garage roof 2022, upstairs air conditioner 2023, and more. This property was carefully designed with the highest quality architectural details and craftsmanship, so expect to be impressed. If the equestrian lifestyle is what you are looking for, this location and property cannot be matched. In the heart of Central Florida, it is close to attractions, airports, downtown Orlando and more. Only five minutes by golf cart to Kissimmee Bay Country Club and golf course. Inquire about a private tour.

2780 Vickie Court, Kissimmee

34744 Homes with Pool View

Newest 34744 Homes with Pool View