Orlando/Chickasaw Real Estate

Orlando/Chickasaw Real Estate

Welcome to Chickasaw, a vibrant and inviting neighborhood nestled in the heart of Orlando, Florida! Known for its friendly atmosphere and beautiful landscapes, Chickasaw offers a unique blend of suburban charm and urban convenience, making it an ideal destination for families, young professionals, and retirees alike.

As part of Orange County, Chickasaw boasts a prime location just minutes away from Orlando's world-renowned attractions, including Walt Disney World, Universal Studios, and a plethora of shopping and dining options. Residents enjoy easy access to major highways, making commuting a breeze and allowing for quick weekend getaways to the stunning beaches of the Atlantic coast.

Chickasaw is characterized by its lush greenery and well-maintained parks, providing ample opportunities for outdoor activities. The area features several community parks equipped with playgrounds, sports fields, and walking trails, perfect for family outings or leisurely strolls with your furry friends. The community spirit here is palpable, with local events and gatherings fostering connections among neighbors.

Education is a priority in Chickasaw, with highly-rated schools serving the area, ensuring that children receive a quality education in a nurturing environment. Additionally, the proximity to higher education institutions, such as the University of Central Florida, offers residents lifelong learning opportunities.

Whether you're looking to buy your first home, invest in a rental property, or find a cozy place to retire, Chickasaw offers diverse real estate options to suit every lifestyle. Experience the warmth and charm of this delightful Orlando neighborhood—where community, convenience, and comfort come together beautifully!

Newest Listings in Orlando/Chickasaw

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
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. Buy with added peace of mind knowing this home has been thoughtfully maintained and improved over the years. Major updates include a roof replacement in 2021, remodeled kitchen in 2020, larger A/C unit replaced in 2022 and smaller A/C unit replaced in 2026, water heater replaced in 2023, and interior and exterior painting completed in 2021. Additional improvements include patio tile completed in 2023, new carpet in the loft in 2026, and new tile in the primary bathroom shower in 2026. These updates reflect the continued care and attention the homeowner has invested in the property. 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
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
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