Orlando/Chickasaw Homes with Pool Community Features

Orlando/Chickasaw Homes with Pool Community Features

Welcome to the vibrant community of Chickasaw in Orlando, Florida, where sunny skies and a lively atmosphere create the perfect backdrop for your dream home. Nestled in the heart of Orange County, Chickasaw offers residents the ideal blend of suburban tranquility and urban convenience. With its close proximity to major highways, you’ll find yourself just a short drive from the excitement of downtown Orlando, world-renowned theme parks, and beautiful natural parks.

Chickasaw is known for its family-friendly environment, featuring excellent schools, lush green spaces, and a variety of recreational options. Whether you're looking to enjoy a leisurely stroll in one of the local parks or engage in community events, this neighborhood has something for everyone.

One of the standout features of homes in Chickasaw is the abundance of properties with private pools. Imagine stepping into your backyard oasis, where you can unwind and soak up the Florida sun in your very own sparkling pool. These homes offer the perfect setting for entertaining friends and family, hosting summer barbecues, or simply enjoying a peaceful afternoon by the water.

The community is well-maintained, with beautiful landscaping and friendly neighbors, creating a welcoming atmosphere that makes you feel right at home. With a variety of home styles and sizes, you’re sure to find the perfect fit for your lifestyle. Come discover the charm of Chickasaw, where your dream home with a pool awaits!

Newest Orlando/Chickasaw Homes with Pool Community Features

9149 Lee Vista Boulevard Unit 405, Orlando
$230,000
2 Beds ⋅ 2 Baths ⋅ S5157640 MLS ⋅ 9149 BLDG.
Well-located 2-bedroom, 2-bath condo featuring a versatile loft that provides additional space for a home office, guest area, or entertainment room. The functional layout offers comfortable living with the added flexibility of the loft, making this property a great option for a variety of lifestyles. Conveniently located with easy access to shopping, dining, major roads, and everyday essentials. Whether you’re looking for your next home or an investment opportunity, this condo offers space, convenience, and a desirable location. Schedule your showing today! Unit is currently rented a great opportunity for an investor.

9149 Lee Vista Boulevard Unit 405, Orlando
10374 Cressida Aly, Orlando
$519,090
5 Beds ⋅ 3 Baths ⋅ O6447637 MLS
EverBe is a new master planned community where convenience and connections combine to create a new standard for home. Located in Orlando with quick access to 417 & 528, this lifestyle community will offer miles of pathways & trails, wi-fi-enabled green spaces, unique outdoor recreation areas, a fitness center, a clubhouse complex with resort pool, 2G internet, and a waterfront amenity and town center. Get excited for EverBe - everything home should ever be! Introducing the Caden bungalow, a brand-new home that combines modern design and ultimate comfort. Featuring our Coastal exterior, this home includes a charming front porch, 5 spacious bedrooms, 3 full bathrooms, a loft, and a 2-car rear-load attached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. This inviting space is perfect for both everyday living and entertaining. The kitchen boasts a large center island, a convenient storage pantry, and top-of-the-line Whirlpool stainless steel appliances—including a refrigerator. Elkins white cabinets, a decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a secondary bedroom and full bathroom. Upstairs, you’ll find the private owner’s suite and bathroom, three additional bedrooms, another full bathroom, loft, linen closet, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a glass-enclosed shower, quartz-topped dual vanity, and private water closet. Throughout the first-floor living spaces enjoy the beauty of wood-look luxury vinyl plank flooring and the convenience of tile in the bathrooms and laundry room. Plush, stain-resistant Shaw brand carpet covers the stairs, loft, and upstairs bedrooms, adding comfort and style. Smart home features include a smart thermostat, a video doorbell, and additional LED downlights—ensuring your home is as connected as it is stunning. This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

10374 Cressida Aly, Orlando
10366 Cressida Aly, Orlando
$523,090
3 Beds ⋅ 3 Baths ⋅ O6447615 MLS
EverBe is a new master planned community where convenience and connections combine to create a new standard for home. Located in Orlando with quick access to 417 & 528, this lifestyle community will offer miles of pathways & trails, wi-fi-enabled green spaces, unique outdoor recreation areas, a fitness center, a clubhouse complex with resort pool, 2G internet, and a waterfront amenity and town center. Get excited for EverBe - everything home should ever be! Introducing the Haddock bungalow, a brand-new home that combines modern design and ultimate comfort. This home includes 3 spacious bedrooms, 2 full bathrooms, a powder room, a loft, a covered lanai, and a 2-car rear-load detached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. The kitchen boasts a large center island, a convenient storage pantry, and Whirlpool stainless steel appliances—including a refrigerator. Elkins white cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite and en suite bathroom, two spare bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a glass-enclosed shower, quartz-topped dual vanity, private water closet, and linen closet. Throughout the entire first floor you'll find wood-look luxury vinyl plank flooring and in the bathrooms, and laundry room you'll enjoy the beauty and convenience of tile flooring. Plush, stain-resistant Shaw carpet covers the stairs, loft, and bedrooms, adding comfort and style. Smart home features include a smart thermostat, a smart doorbell, and LED downlights—ensuring your home is as connected as it is stunning. For added convenience from day one, this home comes complete with 2" faux wood blinds, as well as a washer and dryer! This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

10366 Cressida Aly, Orlando
10256 Aurora View Alley, Orlando
$520,390
3 Beds ⋅ 3 Baths ⋅ O6447614 MLS
EverBe is a new master planned community where convenience and connections combine to create a new standard for home. Located in Orlando with quick access to 417 & 528, this lifestyle community will offer miles of pathways & trails, wi-fi-enabled green spaces, unique outdoor recreation areas, a fitness center, a clubhouse complex with resort pool, 2G internet, and a waterfront amenity and town center. Get excited for EverBe - everything home should ever be! Introducing the Haddock bungalow, a brand-new home that combines modern design and ultimate comfort. This home includes 3 spacious bedrooms, 2 full bathrooms, a powder room, a loft, a covered lanai, and a 2-car rear-load detached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. The kitchen boasts a large center island, a convenient storage pantry, and Whirlpool stainless steel appliances—including a refrigerator. Elkins white cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite and en suite bathroom, two spare bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a glass-enclosed shower, quartz-topped dual vanity, private water closet, and linen closet. Throughout the entire first floor you'll find wood-look luxury vinyl plank flooring and in the bathrooms, and laundry room you'll enjoy the beauty and convenience of tile flooring. Plush, stain-resistant Shaw carpet covers the stairs, loft, and bedrooms, adding comfort and style. Smart home features include a smart thermostat, a smart doorbell, and LED downlights—ensuring your home is as connected as it is stunning. For added convenience from day one, this home comes complete with 2" faux wood blinds, as well as a washer and dryer! This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

10256 Aurora View Alley, Orlando
10571 Evening Star Street, Orlando
$506,490
3 Beds ⋅ 3 Baths ⋅ O6447612 MLS
Under Construction. EverBe is a new master planned community where convenience and connections combine to create a new standard for home. Located in Orlando with quick access to 417 & 528, this lifestyle community will offer miles of pathways & trails, wi-fi-enabled green spaces, unique outdoor recreation areas, a fitness center, a clubhouse complex with resort pool, 2G internet, and a waterfront amenity and town center. Get excited for EverBe - everything home should ever be! Introducing the Haddock bungalow, a brand-new home that combines modern design and ultimate comfort. This home includes 3 spacious bedrooms, 2 full bathrooms, a powder room, a loft, a covered lanai, and a 2-car rear-load detached garage. The heart of the home is the open-concept kitchen, café, and gathering room, all bathed in natural light. The kitchen boasts a large center island, a convenient storage pantry, and Whirlpool stainless steel appliances—including a refrigerator. Elkins white cabinetry, decorative tile backsplash, and quartz countertops complete the sophisticated look. For added convenience, the first floor includes a powder room and coat closet. Upstairs, you’ll find the private owner’s suite and en suite bathroom, two spare bedrooms, a second full bathroom, and the laundry room. The owner’s suite is a true retreat, featuring a walk-in closet and a luxurious en suite bathroom with a glass-enclosed shower, quartz-topped dual vanity, private water closet, and linen closet. Throughout the entire first floor you'll find wood-look luxury vinyl plank flooring and in the bathrooms, and laundry room you'll enjoy the beauty and convenience of tile flooring. Plush, stain-resistant Shaw carpet covers the stairs, loft, and bedrooms, adding comfort and style. Smart home features include a smart thermostat, a smart doorbell, and LED downlights—ensuring your home is as connected as it is stunning. For added convenience from day one, this home comes complete with 2" faux wood blinds, as well as a washer and dryer! This new construction home perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind.

10571 Evening Star Street, Orlando
10969 Heather Haven Street, Orlando
$524,990
4 Beds ⋅ 2 Baths ⋅ O6447602 MLS
Under Construction. EverBe is a new master planned community where convenience and connections combine to create a new standard for home. Located in Orlando with quick access to 417 & 528, this lifestyle community will offer miles of pathways & trails, wi-fi-enabled green spaces, unique outdoor recreation areas, a fitness center, a clubhouse complex with resort pool, 2G internet, and a waterfront amenity and town center. Get excited for EverBe - everything home should ever be! The new construction Dylan bungalow offers a seamless blend of convenience and elegance. Featuring 4 spacious bedrooms, 2 bathrooms, a covered lanai, and a 2-car rear load garage. Step inside to discover a layout that prioritizes both function and flow. At the front, you'll find three spare bedrooms and a bathroom. As you move toward the heart of the home, natural light floods the gathering room and café through large windows, creating a bright, inviting space. The kitchen is a chef’s dream, featuring a large corner walk-in pantry, stainless steel Whirlpool appliances, white cabinetry, quartz countertops, and a decorative subway tile backsplash. The owner’s suite, thoughtfully tucked away for privacy, offers a peaceful retreat from the rest of the home. The en suite bathroom features a dual-sink, quartz-topped vanity, a glass door enclosed shower, and a spacious walk-in closet, ensuring you have all the space and comfort you need. This home’s design selections are equally impressive, with wood-look luxury vinyl plank flooring throughout the living areas, tile flooring spanning the bathrooms and laundry room, and plush, stain-resistant carpet in the bedrooms. For modern convenience, the home is equipped with a smart thermostat and a video doorbell. The Dylan includes everything you need to get started—refrigerator, washer, dryer, and blinds—so you can relax and enjoy the luxury of your new home from day one. Schedule an appointment today and see for yourself how this dream home can become your reality!

10969 Heather Haven Street, Orlando
9672 Doris Lane, Orlando
$339,900
3 Beds ⋅ 3 Baths ⋅ A4708513 MLS ⋅ - BLDG.
SPACE, STYLE & FLEXIBILITY! This Mediterranean-style END-UNIT townhome stands out with soaring high ceilings, an impressive grand loft, 2024 A/C system, and approximately 1,659 sq. ft. of versatile living space. Featuring 3 bedrooms, 2.5 baths, a private lanai, and attached 1-car garage, it offers the extra space and flexibility today's buyers are looking for—all within a gated community with a community pool. Inside, enjoy spacious living and dining areas, an eat-in kitchen, and an upstairs loft overlooking the living space—perfect for a home office, media room, playroom, or second living area. The kitchen features Corian countertops and stainless steel appliances, including a glass-top range, refrigerator, and dishwasher. The upstairs primary suite offers a walk-in closet and private bath with walk-in shower, plus two additional bedrooms. INVESTMENT OPPORTUNITY! Currently tenant occupied with tenants in good standing, offering an attractive opportunity for investors seeking an income-producing property. Conveniently located minutes from Downtown Orlando, Lake Nona, Orlando International Airport, shopping, attractions, UCF, and Valencia College. A standout combination of space, style, versatility, and convenience!

9672 Doris Lane, Orlando
5264 Sapling Sprout Drive, Orlando
$399,900
4 Beds ⋅ 3 Baths ⋅ O6444333 MLS ⋅ 5264 BLDG.
Welcome to Pinewood Reserve! Built in 2021 and beautifully maintained, this spacious 4-BEDROOM, 3-BATHROOM townhome offers 1,809 square feet of thoughtfully designed living space, a 2-CAR REAR-ENTRY GARAGE, and upgraded hard-surface flooring throughout. Step inside to a bright, open-concept main living area where the kitchen, dining and family spaces flow together beautifully. The kitchen features STONE COUNTERTOPS and plenty of room for gathering and entertaining. A FIRST-FLOOR BEDROOM AND FULL BATH provide added flexibility for guests, a home office, or multigenerational living. Upstairs, you'll find the spacious PRIMARY SUITE with an en-suite bath featuring dual sinks and a walk-in closet, along with two additional bedrooms, another full bath, a loft area and conveniently located UPSTAIRS LAUNDRY. Updated interior paint, light fixtures and ceiling fans add to the home's fresh, move-in-ready feel. Enjoy Florida living from the home's PRIVATE COURTYARD AND PATIO, with a park and playground conveniently located across the street. Pinewood Reserve offers fantastic community amenities including a POOL, DOG PARK, PLAYGROUND, WALKING TRAILS, SIDEWALKS AND FISHING POND, along with exterior and grounds maintenance included through the association. Conveniently located near SR 417, shopping, dining and everything the Orlando area has to offer, this nearly-new townhome combines space, convenience and low-maintenance living in a great Central Florida location.

5264 Sapling Sprout Drive, Orlando
7438 Chelsea Harbour Drive, Orlando
$554,900
4 Beds ⋅ 3 Baths ⋅ S5158515 MLS
PRIVACY, SPACE & RESORT-STYLE LIVING in a convenient Orlando location! Welcome to this beautifully updated 4-bedroom, 3-full-bath home with 2,629 sq. ft. in the GATED Vista Lakes community. What makes this home especially inviting is its setting—enjoy open green space and a dog park in front rather than another row of homes, plus NO REAR NEIGHBORS and a peaceful wooded backdrop behind the fenced backyard. It’s a wonderful combination of neighborhood living and breathing room. Step inside to a bright, spacious and move-in-ready interior featuring fresh paint and renovated kitchen. The flexible first floor includes a bedroom and full bathroom, ideal as additional living or guest space, along with a generous flex area that can adapt as an office, game room, media room or second living area. A reverse-osmosis drinking-water filtration system, spacious laundry room and generous storage add everyday convenience. Upstairs, the oversized primary suite offers a spacious bathroom and walk-in closet, with two additional bedrooms completing the second floor. Outside, the 8,732-sq.-ft. lot features a spacious fenced backyard with mature landscaping and fruit trees—an inviting setting for relaxing, entertaining or creating your own outdoor retreat. A 2-car attached garage and generous driveway provide plenty of parking. Located in FEMA Flood Zone X. Living in Vista Lakes is about more than the house. Enjoy community amenities including walking and jogging paths, playgrounds and a resort-style pool complex with multiple pools and a water slide. The location puts you close to everything in Orlando, with convenient access to Orlando International Airport, SR-417, SR-528, Lake Nona/Medical City, Downtown Orlando, major theme parks, shopping, dining and Central Florida attractions. Updated, gated, spacious and surrounded by privacy in both the front and back—come experience what makes this Vista Lakes home special.

7438 Chelsea Harbour Drive, Orlando
7888 Emerald Palm Street, Orlando
$424,990
3 Beds ⋅ 3 Baths ⋅ O6445491 MLS ⋅ 35 BLDG.
Under Construction. EverBe is a new master planned community where convenience and connections combine to create a new standard for home. Located in Orlando with quick access to 417 & 528, this lifestyle community will offer miles of pathways & trails, wi-fi-enabled green spaces, unique outdoor recreation areas, a fitness center, a clubhouse complex with resort pool, 2G internet, and a waterfront amenity and town center. Get excited for EverBe - everything home should ever be! This FH townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-facing garage, all complemented by our Move-In Ready appliance and window blinds package. The first floor is designed with entertaining in mind, offering an open-concept kitchen, café, and gathering room that flow together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Elkins White cabinetry, a decorative tile backsplash, quartz countertops, and stainless-steel appliances, including a refrigerator and vented microwave. The first-floor powder room adds an extra layer of convenience for guests. The entire first floor, including the kitchen, café, and gathering room is finished with elegant Luxury Vinyl Plank Flooring, and the bathrooms and laundry room finished with Ceramic Tile. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. With thoughtful design, high-end finishes, and a focus on everyday convenience, the Dahlia townhome is a perfect blend of style and practicality, offering a truly elevated living experience.

7888 Emerald Palm Street, Orlando
7876 Emerald Palm Street, Orlando
$424,990
3 Beds ⋅ 3 Baths ⋅ O6445123 MLS ⋅ 35 BLDG.
Under Construction. EverBe is a new master planned community where convenience and connections combine to create a new standard for home. Located in Orlando with quick access to 417 & 528, this lifestyle community will offer miles of pathways & trails, wi-fi-enabled green spaces, unique outdoor recreation areas, a fitness center, a clubhouse complex with resort pool, 2G internet, and a waterfront amenity and town center. Get excited for EverBe - everything home should ever be! This FH townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-facing garage, all complemented by our Move-In Ready appliance and window blinds package. The first floor is designed with entertaining in mind, offering an open-concept kitchen, café, and gathering room that flow together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Elkins White cabinetry, a decorative tile backsplash, quartz countertops, and stainless-steel appliances, including a refrigerator and vented microwave. The first-floor powder room adds an extra layer of convenience for guests. The entire first floor, including the kitchen, café, and gathering room is finished with elegant Luxury Vinyl Plank Flooring, and the bathrooms and laundry room finished with Tile. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. With thoughtful design, high-end finishes, and a focus on everyday convenience, the Dahlia townhome is a perfect blend of style and practicality, offering a truly elevated living experience.

7876 Emerald Palm Street, Orlando
3423 Wilshire Way Road Unit 27, Orlando
$229,900
2 Beds ⋅ 3 Baths ⋅ O6441767 MLS ⋅ 3423 BLDG.
Welcome to this 2-bedroom, 2.5-bathroom condo tucked inside the gated community of Victoria Pines. High ceilings create an open, airy feel throughout, while luxury vinyl plank flooring flows through the main living areas. Recent upgrades include a newly tiled primary bathroom shower, new AC 2026, fresh interior paint, updated blinds, new fans and light fixtures, a newer washer and dryer, a 2023 roof, and fresh exterior paint. Ideally located near top-rated schools, shopping, and dining, this condo offers the perfect blend of comfort, style, and low-maintenance living. Don't miss your chance to make it yours!

3423 Wilshire Way Road Unit 27, Orlando
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