Kissimmee (Downtown East) Homes with Pool

Kissimmee (Downtown East) Homes with Pool

Welcome to Downtown East Kissimmee, a vibrant gem nestled in the heart of Osceola County, Florida. Known for its delightful blend of small-town charm and modern conveniences, this region offers a unique lifestyle that appeals to families, retirees, and everyone in between. With its proximity to world-renowned attractions like Walt Disney World and Universal Studios, Downtown East Kissimmee is not just a place to live; it’s a gateway to adventure.

The community is characterized by picturesque streets lined with beautiful homes, many of which feature stunning pools that provide a perfect retreat from the Florida sun. Imagine lounging by your own private oasis, sipping a cool drink while the kids splash around. Homes with pools in this area are highly sought after, offering an ideal setting for entertaining friends or enjoying peaceful evenings under the stars.

In addition to its residential appeal, Downtown East Kissimmee boasts a variety of local shops, restaurants, and parks, making it easy to enjoy the best of both worlds. The vibrant community spirit is palpable, with regular events and festivals that bring neighbors together. Whether you’re strolling through the charming streets or enjoying a day at one of the nearby parks, the warmth of the community is evident.

With its ideal location, family-friendly atmosphere, and homes featuring inviting pools, Downtown East Kissimmee is an excellent choice for anyone looking to embrace the quintessential Florida lifestyle. Come discover your dream home in this enchanting region today!

Newest Kissimmee (Downtown East) Homes with Pool

3107 Rio Grande Trail, Kissimmee
$192,000
2 Beds ⋅ 2 Baths ⋅ S5160949 MLS ⋅ N/A BLDG.
This cozy and attractive 2-bedroom, 2-full-bathroom property in the sought-after Kissimmee area (34741) stands out for its strategic location near Highway 192, providing direct and fast access to Disney theme parks and just minutes away from Hunters Creek. Ideal for both investors and those looking for a vacation home, this property allows short-term rentals and offers the convenience of having the community pool just across the street, combining high profitability, excellent connectivity, and an unbeatable lifestyle in the heart of Central Florida.

3107 Rio Grande Trail, Kissimmee
3235 Falcon Point Drive, Kissimmee
$430,000
3 Beds ⋅ 3 Baths ⋅ S5160773 MLS
Discover this spacious two-story home in desirable Herons Landing, offering 3 bedrooms, 2.5 bathrooms, a versatile loft, and a 2-car garage! The open layout features soaring ceilings, abundant natural light, a combined living and dining area, and a kitchen with stainless steel appliances and a breakfast nook. The first-floor primary suite offers a garden tub, separate shower, dual sinks, and a generous walk-in closet. Additional highlights include laminate and tile flooring, a covered patio, and a flexible upstairs loft perfect for an office, playroom, or additional living space. Enjoy community amenities including a pool, walking trail, park, and playground. LOW HOA AND NO CDD FEES! Conveniently located near Hunters Creek, The Loop, shopping, restaurants, major highways, and Disney attractions. Schedule your showing today!

3235 Falcon Point Drive, Kissimmee
2212 San Vittorino Circle Unit 28-107, Kissimmee
$248,000
4 Beds ⋅ 3 Baths ⋅ S5160753 MLS ⋅ 28 BLDG.
MOVE-IN READY! Renovated in 2020 with new wooden kitchen cabinets, Italian granite countertops, and new ceramic tile flooring in the downstairs living area. Please refer to the attached features sheet. This CORNER UNIT offers 4 bedrooms, 3 bathrooms, and TWO PRIMARY SUITES—one on the ground floor and one upstairs. The downstairs primary bathroom was completely remodeled in 2023. The main living area features French-style doors, and both the air conditioning system and the water heater were replaced approximately one year ago. This beautiful townhome is ideal as either a short-term rental property or a primary residence. It is strategically located near schools, restaurants, theme parks, shopping centers, and major highways. The property has been fully updated, including new paint, flooring, bathrooms, and lighting. Venetian Bay is a 24-hour gated community offering resort-style amenities: 4 swimming pools (the main one is heated), a sun deck, 4 playgrounds, a clubhouse with a kitchen, a fitness center, a game room, a sand volleyball court, basketball and tennis courts, picnic areas, a fishing pier, and more. This gem won’t stay on the market for long! Call today to schedule a private viewing!

2212 San Vittorino Circle Unit 28-107, Kissimmee
2218 Grand Cayman Court Unit 1325, Kissimmee
$198,000
2 Beds ⋅ 2 Baths ⋅ S5160663 MLS ⋅ 2218 BLDG.
Beautiful, freshly painted, and well-maintained 2-bedroom, 2-bathroom condo located on the second floor in the gated, resort-style community of Villa del Sol, featuring controlled access through the Envera system and convenient access to parking. This fully renovated unit offers ceramic tile flooring throughout and spacious walk-in closets in both bedrooms. The community is well maintained, and the buildings have recently been refreshed with a modern exterior color palette. Amenities include a clubhouse, fitness center, two swimming pools, on-site laundry facilities, a car wash area, BBQ and picnic areas, a playground, and tennis courts. An excellent opportunity for a primary residence or investment property. Short-term rentals are permitted, subject to community rules and applicable requirements. Conveniently located near The Loop shopping center, restaurants, parks, and attractions, with easy access to Osceola Parkway, US-192, SR-417, and I-4. The unit is vacant and move-in ready!

2218 Grand Cayman Court Unit 1325, Kissimmee
1386 Isleta Loop, Kissimmee
$335,000
3 Beds ⋅ 3 Baths ⋅ O6454134 MLS ⋅ 1386 BLDG.
Virtually Staged. MODERN 2024 TOWNHOME IN KISSIMMEE | 3 BEDROOMS | 2.5 BATHROOMS | 1-CAR GARAGE Rent-to-Own/ Lease Option Opportunity. Discover the opportunity to own a newer-construction townhome in Kissimmee! Welcome to 1386 Isleta Loop, located in the Osceola Village Townhomes community. Built in 2024, this two-story residence offers 1,676 square feet of living space, featuring 3 bedrooms, 2 full bathrooms, a convenient half bath, and a 1-car garage. If you've been searching for a newer home in Kissimmee without the uncertainty and wait of building from the ground up, this property deserves your attention. The two-story layout offers a practical separation between living and private spaces, while the three-bedroom design provides flexibility for everyday living, working from home, or accommodating guests. Enjoy the advantages of newer construction, including a home built in 2024, in an established residential setting in the heart of the Kissimmee area. Whether you're looking for your next home, relocating to Central Florida, or exploring homeownership opportunities in Osceola County, this property is one to put on your list. Conveniently located in Kissimmee, with access to the surrounding Central Florida area, this home offers an opportunity to enjoy the lifestyle and conveniences of the greater Orlando region. Don't settle for just another listing. Discover the possibilities at 1386 Isleta Loop! Schedule your private showing today.

1386 Isleta Loop, Kissimmee
3261 Whooping Crane Run, Kissimmee
$449,900
3 Beds ⋅ 2 Baths ⋅ S5160545 MLS
Welcome home to this lovely three-bedroom, two bath residence located in the desired community of Eagle's Reserve. The home is well maintained and features vaulted ceilings offering plenty of natural light throughout the home. You will enjoy having tile and laminate floors throughout, giving a clean, cohesive feel and perfect for Florida living! This beauty offers a formal living area, dining area and family room creating a wonderful area to entertain guests. The kitchen features an open floorplan offering updated cabinets with crown molding and stainless appliances. The primary bedroom provides plenty of room to relax at the end of the day and the bathroom provides a separate tub and shower. Take in the tranquil outdoor setting from your large, covered patio. This beauty is set on a corner lot with peaceful pond views and a beautiful fountain offering a calm setting you'll love to come home to! Imagine enjoying your morning coffee or evening libation in your covered patio and making this charming space your own! The community pool is across the street from the home. You will appreciate the vinyl fence on the left side of the house. All this and a new AC unit and new roof in 2025!!! Do not miss this opportunity to see this wonderful home!

3261 Whooping Crane Run, Kissimmee
2530 Avian Loop, Kissimmee
$499,000
4 Beds ⋅ 3 Baths ⋅ S5160399 MLS
Welcome home—you’ve found the upgrades you want and the spaces you’ll love! Located in guard-gated Tapestry, this contemporary residence pairs stylish interiors with a climate-controlled home gym, a covered upstairs balcony, and a backyard made for enjoying Florida living. From the distinctive exterior and paver driveway to the thoughtful details inside, 2530 Avian Loop makes a memorable first impression. The bright, open main living area connects the kitchen, dining, and living spaces for effortless entertaining and everyday comfort. White cabinetry, stainless steel appliances, a subway tile backsplash, and a contrasting island with breakfast-bar seating create a stylish kitchen at the heart of the home. In the living room, decorative wall trim and a fireplace feature wall add warmth and character. A separate den with glass-paneled doors provides an inviting setting for a home office, study, or quiet retreat. Eight-foot interior doors create an elevated sense of space, while luxury vinyl plank flooring throughout the upstairs, den, and staircase brings warmth and continuity to the home. An upgraded stair railing completes the polished look, showcasing the attention to detail found throughout. Upstairs, the spacious primary suite features an en suite bathroom with dual sinks and a glass-enclosed shower. The covered balcony offers another welcoming place to enjoy your morning coffee or wind down in the evening. A standout feature is the garage, converted into a dedicated home gym with its own mini-split air-conditioning unit for comfortable, year-round workouts. Enjoy the convenience of a personal fitness space just steps from your living room. Outside, the generously sized backyard extends your living space with a covered patio, additional pavers, a garden area, storage shed, and playground. From weekend barbecues and gardening to afternoons at play, there’s space to make the most of your time at home. Beyond your front door, Tapestry offers resort-style amenities, including a community pool, splash area, clubhouse, fitness center, playgrounds, and walking trails. Shopping, dining, and entertainment at The Loop and Loop West are nearby, with convenient access to Osceola Parkway, John Young Parkway, and Central Florida’s attractions. Come experience the upgrades, explore the possibilities, and picture your next chapter here. Schedule your private tour today!

2530 Avian Loop, Kissimmee
1218 Bermuda Lakes Lane Unit 203, Kissimmee
$184,900
2 Beds ⋅ 2 Baths ⋅ S5160297 MLS ⋅ The Gables At Lakeside A Condo BLDG.
LOCATION, LOCATION, LOCATION! MOVE-IN READY CONDO IN ONE OF KISSIMMEE'S MOST CONVENIENT AREAS! Discover this spacious 2-bedroom, 2-bathroom condo offering 1,103 square feet of comfortable living space in The Gables at Lakeside community. Ideally situated near the Kissimmee–Hunters Creek area, this property offers convenient access to John Young Parkway, Osceola Parkway, and major roadways connecting Kissimmee to Orlando. ENJOY THE CONVENIENCE OF HAVING EVERYTHING NEARBY! Just minutes from The Loop shopping and entertainment district, Regal Cinemas, popular restaurants, supermarkets, retail stores, medical facilities, and everyday essentials. Its strategic location provides convenient commuting options to employment centers throughout Kissimmee, Hunters Creek, Orlando, and surrounding areas. The condo features an open floor plan, spacious living and dining areas, laminate and ceramic tile flooring, and two generously sized bedrooms with walk-in closets. RECENT IMPROVEMENTS INCLUDE A BRAND-NEW REFRIGERATOR, NEW RANGE, AND AN UPDATED ELECTRICAL PANEL! A washer and dryer are also included, adding convenience for the next owner. Residents can enjoy community amenities including a swimming pool, fitness center, clubhouse, tennis courts, playground, and recreational areas. PERFECT FOR HOMEOWNERS AND INVESTORS ALIKE! Whether you're looking for a primary residence with convenient access to shopping, dining, entertainment, and employment opportunities, or seeking to expand your real estate investment portfolio, this property offers flexibility and long-term potential. Rental use is subject to current condominium association rules and requirements. An excellent opportunity to own a well-located condo in the growing Central Florida market. SCHEDULE YOUR PRIVATE SHOWING TODAY!

1218 Bermuda Lakes Lane Unit 203, Kissimmee
4002 Venetian Bay Drive Unit 101, Kissimmee
$209,990
4 Beds ⋅ 3 Baths ⋅ O6452616 MLS ⋅ 4002 BLDG.
Welcome to 4002 Venetian Bay Drive, Unit 101! This fully furnished corner-unit condo offers a desirable floor plan, resort-style community amenities, and a convenient location approximately 11 miles from Walt Disney World property. The open-concept first floor features a primary suite on the main level, an upgraded kitchen with granite countertops, and French doors leading to a patio. A newer stainless steel refrigerator, purchased in 2024, adds to the kitchen's appeal. One of the property's standout features is the two primary suites, with one on each floor. Both suites include private ensuite bathrooms with whirlpool tubs, offering added comfort and flexibility for owners and guests. A newer washer and dryer are also included, making this furnished property ready to enjoy. The community offers a variety of amenities, including a heated swimming pool, clubhouse, hot tub, BBQ area, and a scenic pond with a walking path. The 24/7 guard-gated entrance provides controlled community access. With short-term rentals allowed, subject to association rules and applicable restrictions, this property offers flexibility for use as a vacation home, investment property, or personal retreat in Central Florida. Enjoy the combination of a functional two-suite layout, community amenities, and convenient access to Disney and the area's many attractions. This home can be purchased with no money down.

4002 Venetian Bay Drive Unit 101, Kissimmee
2578 Amati Drive, Kissimmee
$350,000
3 Beds ⋅ 3 Baths ⋅ S5160145 MLS ⋅ 2578 BLDG.
WELCOME HOME TO TAPESTRY! Discover this beautifully maintained 3-bedroom, 2.5-bath CORNER UNIT located in the highly desirable gated community of Tapestry in Kissimmee. Immaculately kept and move-in ready, this home offers a wonderful combination of comfort, style, and low-maintenance living. The corner-unit location provides an added sense of privacy and natural light, while the thoughtfully designed floor plan offers comfortable spaces for everyday living and entertaining. Pride of ownership is evident throughout—this is a home that has been truly cared for and is ready for its next owner. But life at Tapestry is about much more than the home—it’s about the LIFESTYLE! This beautiful gated community offers resort-style amenities designed for relaxation, recreation, and connection. Enjoy the impressive clubhouse, resort-style swimming pool, fitness center, playgrounds, walking areas, and inviting community spaces where neighbors can gather and enjoy the Florida lifestyle. Conveniently located near The Loop, shopping, dining, entertainment, major roadways, Orlando International Airport, and Central Florida’s world-famous attractions, Tapestry provides the perfect balance between a peaceful residential community and easy access to everything Kissimmee and Orlando have to offer. Whether relaxing at home, enjoying the community amenities, or exploring everything Central Florida has to offer, this immaculate corner unit delivers LOCATION, LIFESTYLE, and CONVENIENCE all in one. Schedule your private showing and come experience the Tapestry lifestyle!

2578 Amati Drive, Kissimmee
2204 Key West Court Unit 511, Kissimmee
$164,000
1 Beds ⋅ 1 Baths ⋅ O6452365 MLS ⋅ 2204 BLDG.
Virtually Staged. ATTENTION INVESTORS! DAILY, SHORT and LONG -TERM RENTALS allowed/ AIRBNB POTENTIAL! LOW HOA FEES! Welcome to VILLA DEL SOL in Kissimmee 34741! This charming CONER GROUND-FLOOR, 1-bedroom, 1-bathroom condo is ideal for vacation rentals or long-term investment. Features include ceramic tile flooring, laminate flooring in the bedroom, a spacious walk-in closet, Whirlpool stainless steel kitchen appliances, a bathroom with dual access, and a laundry room with a full-size washer and dryer. CURRENTLY RENTED TO A GOOD TENANT ON A MONTH-TO-MONTH LEASE! Enjoy RESORT-STYLE AMENITIES in this gated community, including a clubhouse, fitness center, 2 swimming pools, spas, tennis courts, playground, and scenic pond views. Building just painted! DAILY, SHORT and LONG -TERM RENTALS allowed. Great opportunity for investors or future owner-occupants! Schedule your showing today!

2204 Key West Court Unit 511, Kissimmee
4021 Venetian Bay Drive Unit 103, Kissimmee
$195,000
3 Beds ⋅ 2 Baths ⋅ S5159954 MLS ⋅ 4021 BLDG.
INVESTOR ALERT! INCOME-PRODUCING PROPERTY! Excellent investment opportunity in the desirable Venetian Bay Villages resort-style community in Kissimmee! This 3-bedroom, 2-bath condo is ALREADY RENTED FOR $1,800 MONTHLY, GENERATING $21,600 IN ANNUAL GROSS RENTAL INCOME! Major improvements include REPLACED HVAC SYSTEM, WATER HEATER, AND ELECTRICAL PANEL COMPONETS, offering added value and peace of mind! Enjoy outstanding rental flexibility, from short-term stays with a 7-day minimum to annual leases, subject to association requirements. This 24-hour guard-gated community features multiple swimming pools, a clubhouse, fitness center, tennis and basketball courts, and playgrounds. PRIME LOCATION NEAR ALL MAJOR CENTRAL FLORIDA THEME PARKS, INCLUDING WALT DISNEY WORLD, UNIVERSAL ORLANDO, AND SEAWORLD! Just minutes from The Loop shopping center, restaurants, entertainment, and major highways. IMMEDIATE RENTAL INCOME, MAJOR UPGRADES, AND EXCELLENT INVESTMENT POTENTIAL! Don't miss this opportunity!

4021 Venetian Bay Drive Unit 103, Kissimmee
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