Orlando/Chickasaw Homes for Sale

Orlando/Chickasaw Homes for Sale

Welcome to the vibrant community of Chickasaw, nestled in the heart of Orlando, Florida! Known for its friendly atmosphere and convenient location, Chickasaw is a hidden gem in Orange County that offers an ideal blend of suburban tranquility and urban excitement. Just a stone's throw away from the bustling attractions of Orlando, residents enjoy easy access to world-renowned theme parks, shopping centers, and a diverse culinary scene.

Chickasaw boasts a variety of homes for sale, catering to a range of lifestyles and budgets. Whether you're a first-time homebuyer, a growing family, or looking to downsize, you'll find charming single-family homes, modern townhouses, and spacious condos that fit your needs. Many properties in this area feature beautiful landscaping, open floor plans, and updated amenities, making it easy to find a place you’ll love to call home.

The community is also known for its excellent schools, parks, and recreational facilities, making it a perfect place for families. Enjoy weekends at the nearby parks, where you can indulge in outdoor activities or simply relax in the sun. With a strong sense of community and friendly neighbors, Chickasaw offers a welcoming environment that makes settling in a breeze.

If you're ready to explore the homes for sale in Chickasaw, Orlando, you'll discover a vibrant community that combines the best of Florida living with the comforts of home. Don't miss out on the opportunity to find your dream home in this enchanting neighborhood!

Newest Orlando/Chickasaw Homes for Sale

5762 Covington Cove Way, Orlando
$640,000
5 Beds ⋅ 5 Baths ⋅ O6445163 MLS
Welcome to 5762 Covington Cove Way — where spacious living, thoughtful design and the best of the Florida lifestyle come together. From the moment you step through the front doors, soaring cathedral-height ceilings and an impressive open living and dining area create an immediate sense of space and elegance. A distinctive dual-staircase design adds architectural character while providing an inviting connection between the home’s two levels and living spaces. At the heart of the home is an expansive kitchen with seamless flow into the dinette and family room. The kitchen boasts a large island with seating, expansive 48-inch wood cabinets, more than ample granite countertop space and all stainless steel appliances. Across the back of the home, oversized sliding glass doors fill the home with natural light and extend the living area outdoors to a covered, screened patio and expanded outdoor living space. Beyond, a privacy-fenced backyard overlooks tranquil conservation with no rear neighbors, creating a private and peaceful backdrop for morning coffee, weekend gatherings or simply enjoying the beauty of Florida living. The first floor offers a desirable primary suite with a private bath. There is also a flexible fifth bedroom that can easily serve as a home office or study, featuring elegant double doors. A convenient half bath completes the main level. Upstairs, the versatile floor plan continues with three additional bedrooms, including one with its own ensuite bath. Two other bedrooms share a private full bath. A spacious, open bonus area provides an additional gathering space—perfect for movie nights, a game room, pool table, playroom or second family room, with an adjacent third full bath, perfect for visitors. With multiple living areas and flexible spaces throughout, this home is designed to adapt beautifully to the way you live. Situated in the highly desirable Vista Lakes master-planned community, residents enjoy an exceptional array of resort-style amenities, including the Residents Club, multiple pools, fitness center, tennis and pickleball courts, parks, playgrounds, sports fields and scenic lakeside walking trails. With recreation and activities for all ages, Vista Lakes offers not only an outstanding lifestyle but also a true sense of community. The location is equally impressive, with convenient access to Orlando International Airport, Lake Nona and Medical City, along with shopping, restaurants and major roadways including SR 417 and SR 528. From daily conveniences and easy commuting to weekend adventures throughout Central Florida—from world-famous attractions to Florida’s beautiful beaches—this southeast Orlando location puts it all within easy reach. Check out the 3D Matterport and walk through this home NOW! Additional highlights include a 2023 roof and 2018 HVAC system, offering valuable peace of mind for the next homeowner.

5762 Covington Cove Way, Orlando
3785 Peace Pipe Drive, Orlando
$524,999
5 Beds ⋅ 3 Baths ⋅ O6447013 MLS
Welcome to 3785 Peace Pipe Dr in the established Chickasaw Trails community of Orlando. This spacious 5-bedroom, 3-bath single-family home offers over 3,100 square feet of living space with a flexible layout and plenty of room to spread out. A standout feature is the 440+ square foot in-law suite, complete with a private bedroom, full bathroom, and walk-in closet, making it ideal for extended family, guests, or a private home office setup. The home also features a large enclosed Florida room, freshly painted interior, and a spacious tiled outdoor patio with a retractable awning overlooking the backyard. Established landscaping and fruit trees add character to the property, while a storage shed provides additional outdoor storage. The backyard backs up to a canal and wooded area, offering added privacy and frequent sightings of local wildlife, including deer. Additional features include a two-car garage, roof replaced in 2019, and several windows replaced in 2022. Located near grocery stores, shopping, dining, the Lee Vista area, and major highways, this home offers a convenient Orlando location while still providing a peaceful, established neighborhood setting.

3785 Peace Pipe Drive, Orlando
8494 Lake Waverly Lane, Orlando
$570,000
4 Beds ⋅ 3 Baths ⋅ O6446750 MLS
Welcome to 8494 Lake Waverly Lane, a beautifully cared-for 4-bedroom, 3-bath home located in the desirable Vista Lakes community of Orlando. From the moment you step inside, it’s easy to see the love and attention the homeowner has put into making this house feel like home. The interior features inviting open areas that create a comfortable flow for everyday living and entertaining. An upgraded kitchen serves as the heart of the home, complemented by upgraded flooring that adds a fresh, polished feel throughout the living areas. Whether you're gathering with family, entertaining friends, or simply relaxing at home, the open layout provides plenty of flexibility. Adding even more versatility, the home's second story loft area has been converted and is currently being used as an additional bedroom, providing valuable extra space that could also accommodate guests, a home office, or other needs. A 3-car garage offers excellent space for vehicles, storage, hobbies, or recreational equipment. With four bedrooms and three full bathrooms, the home offers the versatility buyers are looking for while maintaining a warm and welcoming atmosphere. Located in the established Vista Lakes community, the home is conveniently situated near shopping, dining, major roadways & Orlando International Airport. This is more than just a house that has been maintained, it’s a home that has been genuinely loved and cared for. Come see the upgrades, space, and welcoming atmosphere for yourself. Schedule your private showing today and discover what makes 8494 Lake Waverly Lane such a special place to call home!

8494 Lake Waverly Lane, 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
6930 Remington View Court, Orlando
$699,000
5 Beds ⋅ 4 Baths ⋅ O6443869 MLS
A Home and Lifestyle That Has It All! Experience the best of Vista Lakes living at 6930 Remington View Court! This impressive 5-bedroom, 4-bathroom home offers approximately 3,185 square feet of living space on a generous quarter acre lot, creating an exceptional combination of space, comfort, recreation, and location. In addition to space, this home is complemented by the lifestyle that comes with living in Vista Lakes. This is more than a neighborhood, it is a master-planned community designed around recreation, outdoor living, and an active lifestyle. Located in Southeast Orlando, Vista Lakes is conveniently positioned near major roadways, shopping, dining, Orlando International Airport, Lake Nona, and Central Florida’s world-famous attractions. Once inside you will find 12-foot ceilings, open and airy layout, custom finish work, natural light and ample storage throughout. Multiple bedrooms on a split floor plan, including two individual en-suite bedrooms (great for guests and family visits). Primary bedroom is spacious with space for a separate sitting area. Private, screened swimming pool (resurfaced in 2022) with spa and ample space for entertaining. 2026 upgrades include all interior paint, light fixtures, door hardware, all carpeting, plus some new landscaping. Many recent systems updated including new roof in 2024, main AC in 2023, exterior paint 2024, and attic insulation refreshed 2022. Enormous 3 car garage has its own Central AC and a new durable Shark Coating floor. Use this space for auto storage, a workshop, a game room, she-shed or mancave. Vista Lakes Community offers an impressive array of amenities including: <ul> <li>Residents’ Club / clubhouse for gatherings, activities, and private events <li>Five community pools, including the recreational and lap-pool facilities at the main Amenities Center <li>Dedicated fitness center equipped with cardio, strength-training, and functional fitness equipment <li>Four lighted tennis courts <li>Two lighted pickleball courts <li>Four community parks <li>Soccer field <li>Little League-sized baseball/softball field <li>Two batting cages <li>Basketball courts <li>Children’s playgrounds <li>Lakeside walking trails <li>Community boat docks <li>Fishing pier <li>Pavilions and outdoor gathering areas <li>Free Wi-Fi at the Amenities Center/Residents’ Club <li>Community activities, events, and special gatherings <li>Access to the community’s extensive recreational facilities and beautifully maintained common areas <li>Plus, residents special social and recreational privileges through Rio Pinar Golf & Country Club, including preferred golf rates and access to social facilities, subject to the club’s current terms. (Vista Lakes Community Association INC) </ul> Come discover your Home at 6930 Remington View Court in Vista Lakes and experience Florida living at its fullest!

6930 Remington View Court, Orlando
6735 Reverie Park Avenue, Orlando
$910,000
5 Beds ⋅ 5 Baths ⋅ S5158115 MLS
Imagine coming home to a place where luxury, comfort and nature come together effortlessly. Welcome to this exceptional 2024 Pulte Scarlett residence in EverBe, where elevated finishes, designer details and statement lighting create a distinctive sense of style from the moment you enter. With 5 bedrooms, 4.5 bathrooms, a private office and multiple living spaces, every area of this home has been designed to be enjoyed. At the heart of the home, the gourmet kitchen features quartz countertops, built-in appliances, an oversized island and walk-in pantry, flowing seamlessly into the main living and dining areas. Expansive multi-panel sliding doors open to an impressive covered lanai with a custom outdoor kitchen and bar featuring granite countertops, built-in grill, cooktop, sink, beverage/wine refrigerator, TV and ceiling fans. With no rear neighbor and a peaceful conservation backdrop, indoor and outdoor living blend beautifully. Upstairs, the primary suite features a custom walk-in closet and an elegant bath with dual vanities and an oversized walk-in shower with a ceiling-mounted rain shower, handheld shower and built-in bench. A second en-suite bedroom, additional bedrooms and a spacious upstairs lounge provide remarkable flexibility, while a private first-floor guest suite creates its own welcoming retreat. Additional highlights include motorized window treatments in select rooms, custom closet systems, whole-home water filtration, kitchen reverse osmosis, an upstairs laundry room with cabinetry and utility sink, and an epoxy-finished garage floor. Beyond the home, EverBe offers resort-style amenities, scenic walking trails and green spaces, creating a rare connection to nature while keeping you close to everything Orlando has to enjoy. Convenient access to SR-417 and SR-528 connects you to Lake Nona, Orlando International Airport, shopping, dining and major destinations. Some homes photograph beautifully—this is one you need to experience in person. Schedule your private showing today and discover what makes this EverBe residence truly stand apart. An opportunity this distinctive deserves to be seen before it’s gone.

6735 Reverie Park Avenue, Orlando
5737 Lake Champlain Drive, Orlando
$455,000
4 Beds ⋅ 2 Baths ⋅ O6444577 MLS
LOCATION! LOCATION! LIFESTYLE! Welcome to 5737 Lake Champlain Dr, a beautifully maintained single-story home in the sought-after Vista Lakes community. Offering 4 bedrooms, 2 bathrooms, 2,102 square feet, a 2-car garage, and a desirable split floor plan, this home delivers the space, comfort, and privacy today’s buyers are looking for. Pride of ownership shows throughout, with a functional layout that makes everyday living and entertaining easy. But what truly sets this home apart is the lifestyle. Vista Lakes offers resort-style amenities including pools, a fitness center, tennis and pickleball courts, parks, trails, a fishing pier, and community events — all in an established neighborhood with incredible convenience. Enjoy easy access to Lake Nona, Orlando International Airport, major roadways, shopping, dining, and everything Southeast Orlando has. This is more than just a house — it is an opportunity to enjoy space, community, convenience, and lifestyle all in one. Come see why Vista Lakes continues to be such a desirable place to call home.

5737 Lake Champlain Drive, Orlando
8625 Redskin Court, Orlando
$370,000
3 Beds ⋅ 2 Baths ⋅ O6442696 MLS
VERSATILE BONUS SPACE + BACKYARD ENTERTAINING + CENTRAL ORLANDO LOCATION! This home blends a functional layout, low-maintenance finishes, and flexible living spaces in a convenient Orlando location. The split-bedroom floor plan offers comfortable separation between the primary and secondary bedrooms, while the L-shaped living and dining areas provide flexibility for both everyday living and entertaining. Wood-plank vinyl flooring flows throughout the main living areas for a clean, cohesive look. A standout feature is the spacious, air-conditioned Florida/bonus room with tile flooring, offering valuable additional living space with endless possibilities for a home office, fitness area, hobby space, playroom, or entertainment room. Outside, the beautiful backyard creates an inviting space to relax and entertain, with a recently upgraded deck that’s ready for weekend barbecues, outdoor gatherings, or enjoying the Florida sunshine. Enjoy the peace and quiet of this desirable neighborhood with the added benefit of no monthly HOA fee! Conveniently located near shopping, dining, major roadways, and everyday amenities, yet tucked away from the area's busiest corridors, this home offers accessibility with a more relaxed residential setting. Come see how easily this versatile home can fit your lifestyle—schedule your showing today!

8625 Redskin Court, Orlando
6738 Vista Park Boulevard, Orlando
$669,500
4 Beds ⋅ 3 Baths ⋅ O6440029 MLS
RELAX AND ENJOY THE FLORIDA LIFESTYLE! LAKE VIEW HOME COMPLETE WITH SOLAR HEATED, SCREENED POOL! DESIRABLE 4 BEDROOM, 3 FULL BATH HOME WITH ADDITIONAL UPPER LEVEL BONUS ROOM PERFECT FOR GAME ROOM, CRAFT ROOM OR ADDITIONAL LIVING AREA! SPLIT BEDROOM PLAN! WOOD LOOK PLANK-TILE FLOORING THRU OUT THE MAIN LIVING AREA INCLUDING THE MASTER BEDROOM! NO CARPET! FORMAL LIVING AND DINING ROOM COMBO! VAULTED CEILINGS! NUMEROUS BUILT INS THRU OUT AND LOTS OF DETAILING AS THIS WAS A FORMER MODEL HOME! OPEN AND AIRY KITCHEN, FAMILY ROOM COMBO LEADS TO PATIO AND SCREENED POOL! OWNED WHOLE HOUSE SOLAR SYSTEM! KITCHEN FEATURES GRANITE COUNTERS, UPDATED CABINETRY WITH PULLOUT DRAWERS AND STAINLESS APPLIANCES! INSIDE LAUNDRY ROOM! 3 CAR OVERSIZED GARAGE! ROOF 2018! 15 SEER A/C 2017! VISTA LAKES OFFERS INCREDIBLE RESORT LIKE AMENITIES! OVERSIZED COMMUNITY POOL WITH A WATER SLIDE, PLUS A SEPARATE LAP POOL, KIDDIE POOL, FITNESS CENTER, PICKLE BALL COURTS, TENNIS COURTS ETC. ETC. SOMETHING FOR EVERYONE AND MINUTES FROM YOUR HOME AS A RESIDENT OF VISTA LAKES! AMAZINGLY BEAUTIFUL! WITHIN YOUR OWN GATED COMMUNITY YOU CAN ENJOY THE WALKING TRAIL AROUND THE LAKE, THE PRIVATE DOCK AS WELL AS A PLAYGROUND! WELCOME HOME!

6738 Vista Park Boulevard, Orlando
8818 Hastings Beach Boulevard, Orlando
$474,900
4 Beds ⋅ 3 Baths ⋅ S5156567 MLS
Welcome home to this beautifully maintained and impressively spacious residence, perfectly situated in a beautiful neighborhood. From the moment you enter, you’ll appreciate the seamless open-concept design, ideal for both everyday living and effortless entertaining. The main level showcases elegant tile flooring throughout, including the staircase, offering a clean and modern feel. The first-floor primary suite provides both comfort and privacy, creating a peaceful retreat conveniently located away from the additional bedrooms. Upstairs, you’ll find three generously sized bedrooms along with a versatile loft space—perfect for a home office, media room, or additional living area to suit your lifestyle. The home also features 2.5 bathrooms and a spacious two-car garage. Step outside to your oversized backyard, offering endless potential to design your own private oasis, with ample room to add a custom pool and outdoor living space. Opportunities like this don’t come often—schedule your private showing today and experience all this home has.

8818 Hastings Beach Boulevard, Orlando
8251 Newbury Sound Ln, Orlando
$429,000
4 Beds ⋅ 2 Baths ⋅ O6436205 MLS
Welcome to 8251 Newbury Sound Ln! Beautiful 4-bedroom, 2-bath home offering 1,864 sq. ft. of living space on a desirable 0.19-acre lot in Orlando. Huge backyard space to make your own or even install a pool! The home features fresh interior paint, a spacious and functional floor plan, comfortable living areas, and generously sized bedrooms. Big 2 car Garage! Fresh Landscaping! A/C is 2017! Conveniently located near major highways, shopping, dining, schools, and Orlando’s many attractions. A great opportunity for homeowners or investors looking for a well-located property in the 32829 area.

8251 Newbury Sound Ln, Orlando
10710 Leafy Laurel Street, Orlando
$524,990
3 Beds ⋅ 2 Baths ⋅ O6435782 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 3 spacious bedrooms, 2 bathrooms, an enclosed flex room, and a 2-car rear garage. Step inside to discover a layout that prioritizes both function and flow. An enclosed flex room, two spare bedrooms, and a guest bathroom are situated at the front of the home. As you move toward the heart of the home, natural light pours through the large windows in the gathering room and cafe, creating a bright and open living 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 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 main living areas, plush, stain resistant carpeting in the bedrooms, and tile flooring in the bathrooms and laundry room. For modern convenience, the home is equipped with a smart thermostat and a video doorbell. This home 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!

10710 Leafy Laurel Street, Orlando
Start Your Search