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

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
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
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
11139 Rising Sun Street, Orlando
$460,000
3 Beds ⋅ 3 Baths ⋅ O6443620 MLS ⋅ 11129 BLDG.
Welcome to 11139 Rising Sun St, a beautifully designed 3-bedroom, 2.5-bathroom townhome offering 1,652 square feet of thoughtfully laid-out living space in the sought-after EverBe community, built by Pulte Homes in 2024. This nearly-new Foxtail floor plan combines modern design with everyday functionality, featuring an open-concept layout, contemporary finishes, and low-maintenance living — perfect for first-time buyers, downsizers, or investors alike. EverBe is one of East Orlando's newest master-planned communities, offering residents access to resort-style amenities, scenic walking trails, and a true sense of community, all while being conveniently located near major highways, Orlando International Airport, Lake Nona's Medical City, and a variety of shopping and dining options. With builder incentives potentially available and a like-new condition throughout, this home offers the comfort of modern construction without the wait of new build timelines.

11139 Rising Sun Street, Orlando
6735 Reverie Park Avenue, Orlando
$890,000
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
Start Your Search