Kissimmee Homes with Pool View

Kissimmee Homes with Pool View

Located in the heart of Osceola County, Florida, Kissimmee is a vibrant city known for its proximity to world-famous attractions like Walt Disney World Resort and Universal Studios. With its warm climate, Kissimmee offers residents a perfect mix of outdoor activities, entertainment, and a thriving real estate market.

Homes with pool views are a sought-after feature in Kissimmee, allowing residents to enjoy the sunshine and relax in the comfort of their own backyard. Whether you're looking for a cozy single-family home or a spacious villa, Kissimmee offers a variety of options to suit every lifestyle. Imagine waking up to the tranquil sight of a shimmering pool right outside your window, creating a peaceful oasis just steps away from your doorstep.

In Kissimmee, homes with pool views provide not only a luxurious living experience but also a great investment opportunity. Whether you're looking for a vacation home or a permanent residence, Kissimmee's real estate market offers a range of options to fulfill your dream of owning a home with a stunning pool view.

Newest Kissimmee Homes with Pool View

$359,000
3 Beds ⋅ 2 Baths ⋅ Windsong SubDv. ⋅ 34744 Zip Code
Welcome to this beautifully remodeled 3-bedroom, 2-bath, block pool home offering the perfect combination of style, comfort, and convenience. Situated on an oversized, fully fenced backyard, this property provides plenty of space for entertaining, pets, play, or simply relaxing by your private pool. The interior has been completely remodeled with modern finishes, creating a move-in ready home you'll love from the moment you walk in. Conveniently located just minutes from everything Kissimmee has to offer, including approximately 1 mile to AdventHealth Kissimmee, 2 miles to historic Downtown Kissimmee, and only 4 miles to The Loop, where you'll enjoy shopping, dining, and entertainment. With easy access to major highways, Orlando attractions, schools, and everyday conveniences, this is a place you'll be proud to call home. Come see for yourself why this beautiful property is the perfect place to begin your next chapter.

1240 Windway Circle, 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 in a desirable neighborhood!

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
$219,900
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
$339,000
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
$699,500
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
$775,000
6 Beds ⋅ 5 Baths ⋅ North Point Ph 2b-2c SubDv. ⋅ 34744 Zip Code
PRICE JUST REDUCED! MOVE-IN READY! Check out the VIRTUAL TOUR link for full, interactive 3D Matterport Tour! Welcome to this exceptional 6-bedroom, 4.5-bathroom Lennar “Next Gen” home in the gated North Point community of Kissimmee, conveniently located near the Lake Nona area. Built in 2014 and offering approximately 3,899 heated square feet, this spacious two-story residence features an open floorplan, high ceilings, crown molding, ceiling fans, stone counters, and a large eat-in kitchen with an island and appliances included. A standout feature of the home is the attached private-entry in-law suite, complete with private bedroom and bathroom, living area, kitchenette, refrigerator, microwave, washer and dryer, offering excellent flexibility for multigenerational living, extended guests, or added privacy within the home. The interior has been thoughtfully maintained and improved with owner-reported updates including a complete kitchen remodel, remodeled bathrooms, remodeled closets, new woodwork throughout, new fans throughout the home, new Kohler toilets in all bathrooms, updated first-floor outlets with USB connections, new door handles, utility room cabinetry, and multiple updated appliances. Outdoor living is another major highlight, with a heated private in-ground pool, lighting, screen enclosure, covered and screened rear lanai, cleaned and sealed pool deck, AstroTurf around the pool, deck TV area with new fan, landscape rock along both sides of the home, and outdoor furniture on the deck included with the sale. Additional exterior improvements include updated front lighting and porch lighting, sealed front paver/block driveway areas, installed front-side pavers, stone pad sidewalk area, water softener, irrigation system, rain gutters, vinyl fencing, solar, and a 3-car attached garage with overhead storage shelving. Community amenities include a clubhouse, playground, and community pool. This home offers size, flexibility, updates, and a desirable gated location all in one property.

2850 Spring Breeze Way, Kissimmee
$610,000
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
$219,777
2 Beds ⋅ 3 Baths ⋅ Rio Hills Townhouses SubDv. ⋅ 34743 Zip Code
PRICE TO SELL!!!UP TO $4,000 IN BUYER INCENTIVES AVAILABLE! This property may qualify for up to $4,000 in closing cost credit when using the seller's preferred lender. Ask us how to qualify! Welcome to this well-maintained 2-bedroom, 2.5-bath townhouse located in a gated community offering both comfort and convenience. This two-story unit features a functional open floor plan with a spacious living and dining area, perfect for everyday living and entertaining. The kitchen includes ample cabinet space, breakfast bar seating, and flows seamlessly into the main living area. Upstairs, both bedrooms are generously sized and feature their own private bathrooms, providing ideal privacy for residents or tenants. A convenient half bathroom is located on the first floor. Enjoy outdoor living with a private patio area, along with access to the community pool. The property also includes in-unit laundry for added convenience. This property is perfect for homeowners or investors, with strong rental potential in a desirable, gated community setting. Conveniently located near major roadways, and area attractions. Ideally situated near top-rated schools, shopping, dining, hospitals, and daily conveniences—plus just minutes from Disney Parks, Universal Studios, and SeaWorld! Schedule your showing today.

336 Cervantes Drive Unit 336, Kissimmee
$399,000
3 Beds ⋅ 2 Baths ⋅ Bvl Unit 9 6th Add SubDv. ⋅ 34743 Zip Code
This 3 bedrooms, 2 bath pool home with a bonus/family room and two car garage is partially upgraded and ready for your finishing touches. Featuring an open floor plan with a split-bedroom layout, premium tile flooring throughout, vaulted ceilings, and generous living space, this home offers both comfort and functionality. The updated kitchen showcases quartz countertops, 42-inch shaker cabinets, new stainless steel appliances, and a convenient breakfast bar - perfect for everyday living and entertaining. The spacious primary suite includes a large walk-in closet and upgraded bathroom with a beautifully tiled walk-in shower. Situated on an oversized, fully fenced lot, the property offers exceptional privacy and outdoor potential. With minor cosmetic improvements and the right vision, this home can truly shine. Solar panels are paid off. Ideally located just minutes from Medical City, major hospitals, restaurants, shopping, Disney attractions, airport and major roadways. An incredible opportunity you don't want to miss!

247 Competition 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
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