Chickasaw Homes 

Chickasaw in Orlando, FL, is a vibrant and sought-after real estate community known for its charming homes and convenient access to nearby amenities and attractions. The neighborhood boasts a diverse range of residential properties, catering to various preferences and budgets. Its prime location within the Orlando metropolitan area makes Chickasaw an ideal choice for both families and professionals looking to settle in a dynamic and thriving city.

Residents of Chickasaw can enjoy a plethora of nearby amenities, including shopping centers, restaurants, and recreational facilities. The area's proximity to major highways and public transportation hubs ensures easy connectivity to the rest of Orlando, making daily commutes and weekend getaways a breeze. For entertainment and leisure, residents can explore the many attractions Orlando has to offer, such as the world-renowned theme parks like Walt Disney World, Universal Studios, and SeaWorld, as well as museums, theaters, and sporting events, providing endless opportunities for fun and relaxation.

Chickasaw in Orlando, FL, presents an enticing real estate prospect for those seeking a well-rounded and convenient lifestyle. With its range of housing options, access to nearby amenities, and proximity to Orlando's thrilling attractions, Chickasaw is a charming and attractive neighborhood that appeals to a diverse array of individuals and families looking to call this vibrant city their home.

Available Chickasaw Homes For Sale

$350,000
4 Beds ⋅ 2 Baths ⋅ O6419413 MLS
Under contract-accepting backup offers. Now’s your chance to design the home of your dreams right in the heart of Orlando! Situated in the established Chickasaw Oaks community, this single-story home offers 4 bedrooms, 2 bathrooms, and nearly 2,000 square feet of space with a versatile three-way split floor plan designed for both privacy and functionality. Inside, you'll find formal living and dining areas, plus a kitchen that overlooks the family room creating a warm environment suited for gatherings. The enclosed patio adds even more flexible living space and is currently enjoyed as a sunroom but can easily be adapted into an office, play area, or hobby room. For anyone looking to build equity, this home offers a fantastic foundation, and the design options are truly endless! Here, you’re ideally located with easy access to the 417 and 408, you're approximately 15 minutes from Orlando International Airport and 20 minutes from both UCF and Lake Nona. Bring your ideas, bring your vision, and unlock the potential of this beautiful home!

8657 Crossbay Drive, Orlando

Courtesy of REAL BROKER, LLC

$469,900
4 Beds ⋅ 4 Baths ⋅ O6433911 MLS
Are you finally ready to be a homeowner in 2026?  7613 Bear Claw Run in Orlando could be your new home, offering an abundance of useful space in every corner, from top to bottom.  A newly painted front door and trim welcome you to the oversized front porch, where you can spend countless hours rocking back and forth, and enjoying being part of this exceptional neighborhood.  Once inside, you can immediately begin to appreciate the throughout floorplan, which does not include a single stitch of carpet!  A formal living room and dining room are positioned at the front of the home, with convenient access to the open kitchen & living room.  If you like to entertain, host holidays and birthday parties, this is the place where everyone will gravitate.  The open kitchen is the heartbeat of the home, while you prepare appetizers, you and your guests can converse and cherish that quality time.  Your primary bedroom is located separately from the other bedrooms, offering that needed privacy after a long day.  Do you need that extra space in the bathroom to get ready in the mornings?  If you said yes, then your en-suite bathroom will not disappoint. Two sinks make everyone's life much easier, as well as a soaking tub and separate shower.  Once at the top of the stairs, the oversized loft will be the perfect dedicated space for the kids to play and complete their homework, and simply make it a place of their own.  Three other generously sized bedrooms are upstairs, all with laminate flooring, and all serviced by two other full bathrooms...yes you read that correctly....two full bathrooms upstairs!  Only 5 minutes to the 408, 10 minutes to Downtown Orlando, 15 minutes to Waterford Lakes Town Center, 25 minutes to MCO  > LOW HOA | ENTIRELY FENCED IN YARD | ZERO CARPET | 2018 HVAC | 2024 WATER HEATER | 2018 ROOF <

7613 Bear Claw Run, Orlando

Courtesy of RE/MAX PRIME PROPERTIES

$354,900
3 Beds ⋅ 2 Baths ⋅ O6433171 MLS
Under contract-accepting backup offers. Ready to Welcome You Home! This fantastic 3-bedroom, 2-bath single-family home with a 2-car garage is ready just in time for the holidays! Nestled on a spacious corner lot in a well-established neighborhood, this move-in-ready gem offers the perfect blend of comfort, updates, and convenience. Step inside to an open, split floor plan featuring an updated kitchen with stainless steel appliances (2019), a refreshed guest bath, and a spacious living area perfect for relaxing or entertaining. Enjoy outdoor living year-round on the large screened-in patio overlooking a fully fenced yard - ideal for pets, play, or simply unwinding. Major updates include a new roof (2022), updated windows (2020), A/C (2019), and freshly textured and painted ceilings (2022), giving you peace of mind for years to come. Located with easy access to shopping, schools, theme parks, and major highways, this home checks all the boxes. Don't miss your chance to make it yours - schedule your tour today!

4702 Hopespring Drive, Orlando

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

$445,000
3 Beds ⋅ 2 Baths ⋅ O6418831 MLS
Under contract-accepting backup offers. MULTIPLE OFFERS !! BEAUTIFULLY UPDATED & MOVE-IN READY! Beautiful 3-bedroom, 2-bath FULLY FENCED IN home with a SHED/OFFICE in desirable CHICKASAW TRAILS community with NUMEROUS 2026 IMPROVEMENTS and a LOW HOA. Major updates include a new ARCHITECTURAL ROOF (7/2026), full replumb (7/2026), new WATER HEATER (7/2026), fresh interior and exterior paint, new 5¼-inch baseboards, new entry door, updated lighting, new ceiling fans, and new 2-inch faux wood blinds throughout. The A/C motor was replaced in 4/2026. The updated KITCHEN features new 36-inch all-wood cabinetry, quartz countertops, stainless steel appliances, recessed lighting, pendant lights, and a new garbage disposal. Both bathrooms have been beautifully remodeled, including a spacious 72-inch dual-sink vanity in the primary bath, new fixtures, toilets, and finishes. Additional improvements include new landscaping, a new IRRIGATION control box and sprinkler heads, a new wood privacy fence and gate, new pantry and closet shelving, and a freshly painted two-car garage with a newly painted garage floor. A standout feature is the DETACHED AC'D BACKYARD OFFICE , which has been rebuilt and updated with a new roof, flooring, baseboards, exterior drywall, and window A/C. This flexible space is perfect for a home office, gym, studio, hobby room, or private retreat. Conveniently located near shopping, dining, schools, and major roadways, this well-maintained and extensively updated home offers comfort, style, and many major improvements already completed. Schedule your private showing today!

4040 Eagle Feather Drive, Orlando

Courtesy of INVESTOR'S REAL ESTATE LLC

$530,000
4 Beds ⋅ 3 Baths ⋅ O6428014 MLS
Experience the perfect blend of comfort, style, and lasting value in this beautifully update 4-bedroom, 2.5 bath home in the highly sought after Chickasaw Trails community. Major updates include a. New roof (2021), solar panels (2021), a new HVAC system, and a new hot water heater, Offering energy efficiency and peace of mind for years to come. Inside, soaring vaulted ceilings, a cozy wood burning fireplace, and an open concept layout create a bright and inviting living space. The updated Kitchen features granite counter tops, modern appliances and stylish new cabinetry, flowing seamlessly into the spacious family room. The first-floor primary suite offers privacy and convenience, while three generously sized, well separated upstairs bedrooms provide the perfect Space for children, guests, or a home office. Relax on the screened lanai overlooking a peaceful conservation area with added backyard privacy. Unwind in the private hot tub or enjoy outdoor Gatherings around the barbecue while embracing Florida's year-round lifestyle. Additional highlights include a two-car garage, mature landscaping, low HOA fees, a middle school just a 10 min walk away, and quick access to SR-417 Shopping, dining and everyday conveniences. Movie-in ready, this exceptional home is a rare opportunity. Schedule your showing today!

3920 Running Water Drive, Orlando

Courtesy of PREMIER SOTHEBYS INT'L REALTY

$419,900
4 Beds ⋅ 2 Baths ⋅ S5152914 MLS
Beautifully maintained 4-bedroom, 2-bath pool home in the desirable Chickasaw Oaks community! This move-in-ready home features tile flooring throughout (no carpet), high ceilings, abundant natural light, stainless steel appliances, a fully fenced backyard, and a private pool perfect for entertaining. Recent updates include a 2025 roof and freshly painted interior and exterior. Conveniently located with easy access to SR 417, SR 408, Orlando International Airport (approximately 7–10 minutes), schools, shopping, dining, Lake Nona, Lee Vista, and Waterford Lakes. Owner occupied and easy to show. Please text Kenia to schedule an appointment.

4901 Reginald Road, Orlando

Courtesy of LA ROSA REALTY ORLANDO LLC

$419,900
4 Beds ⋅ 2 Baths ⋅ O6421665 MLS
WOW! FULLY RENOVATED ORLANDO POOL HOME • NEW PERMITTED ROOF JULY 2026 • NEW A/C • LOW HOA • 4 BEDROOMS • SCREENED POOL • 0.27-ACRE LOT • REPIPE 2022 • 2-CAR GARAGE • SELLER MOTIVATED! Welcome to 4768 Crossbow Ct, Orlando, FL 32829, a beautifully renovated 4-bedroom, 2-bath pool home combining major updates, an oversized lot, and inviting indoor-outdoor living. Major improvements include a NEW permitted roof installed July 2026, NEW A/C, and whole-home repipe completed in 2022. Inside, enjoy a bright open-concept layout with extensive updates throughout. The renovated kitchen features granite countertops, new stainless steel appliances, abundant cabinetry, and generous preparation space. Both bathrooms have been tastefully renovated with contemporary finishes. Additional improvements include new flooring throughout, modern lighting and fixtures, fresh interior and exterior paint, and updated landscaping. The spacious primary bedroom features sliding glass doors opening directly to the screened swimming pool and patio. Three additional bedrooms provide flexible space for a variety of needs. Outside, enjoy the screened pool, covered outdoor space, and oversized 0.27-acre lot with room for entertaining, recreation, gardening, and outdoor dining. The attached 2-car garage features finished flooring and additional storage. Conveniently located in East Orlando with access to Orlando International Airport (MCO), SR-408, SR-417, SR-528, Waterford Lakes Town Center, UCF, Valencia College, shopping, dining, parks, healthcare facilities, and major employment areas. NEW ROOF + NEW A/C + POOL + LOW HOA + RENOVATED + OVERSIZED LOT! SELLER MOTIVATED — SCHEDULE YOUR PRIVATE SHOWING TODAY! ALTERNATIVE HOMEOWNERSHIP OPTION MAY BE AVAILABLE: A bank-funded lease-to-own/homeownership program offered through an independent third-party provider may be available to qualified applicants. Depending on program requirements, income may be documented using recent bank statements, including the most recent three months, instead of traditional tax-return documentation. Eligibility, income verification, credit requirements, available funds, property eligibility, terms, and final approval are determined solely by the third-party provider. Not seller financing. Approval is not guaranteed. Equal Housing Opportunity. Ask for program details.

4768 Crossbow Court, Orlando

Courtesy of IAD REAL ESTATE

$389,000
4 Beds ⋅ 2 Baths ⋅ S5145852 MLS
NO HOA | HUGE BACKYARD | MINUTES FROM DISNEY & AIRPORT! This 4-bedroom, 2-bath home offers a rare combination of location, space, and flexibility. Centrally located near major attractions, shopping, dining, and with quick access to the airport, this property is perfect for both homeowners and investors. Featuring a functional layout and well-maintained interior, the highlight is the oversized backyard—ideal for entertaining, future expansion, or creating your own outdoor oasis with no HOA restrictions. Opportunities like this don’t come up often in this area, schedule your showing today!

8509 Lyonia Drive, Orlando

Courtesy of EXP REALTY LLC

$390,000
3 Beds ⋅ 2 Baths ⋅ L4960327 MLS
Welcome to 8830 Scioto Court, Orlando, FL 32829—a well-maintained 3-bedroom, 2-bath pool home located on a quiet cul-de-sac with mature trees, offering privacy and a peaceful neighborhood setting.The home features kitchen and bathroom renovations completed in September 2021, providing updated finishes and a refreshed interior. Major updates include a new roof installed in November 2023, and the AC system is approximately 15 years old.Step outside to enjoy the private backyard pool, perfect for relaxing or entertaining. The pool area includes a safety gate, creating a great outdoor space for families and pet owners.The location provides convenient access to many of Central Florida’s top destinations. The home is less than 20 minutes from Orlando International Airport, about 10 minutes from SR-417, 15 mins drive to downtown Orlando Via SR-408 and close to Lake Nona, Medical City, shopping, dining, and everyday conveniences. It’s also approximately 35–40 minutes from Walt Disney World, making it easy to enjoy one of Central Florida’s most popular attractions

8830 Scioto Ct, Orlando

Courtesy of WATERS REAL ESTATE GROUP

$449,000
4 Beds ⋅ 4 Baths ⋅ O6385029 MLS
Welcome to this beautifully maintained home nestled in a quiet, established East Orlando neighborhood, offering the perfect balance of comfort, functionality, and exceptional location convenience. This move-in-ready property is ideal for homeowners, families, or investors seeking long-term value in one of Orlando’s most accessible areas. ust minutes from University of Central Florida, one of the nation’s largest universities Close to Valencia College (East Campus) Easy access to SR-408 (East-West Expressway) and SR-417 (Central Florida Greeneway) for convenient commuting

7430 Bear Claw Run, Orlando

Courtesy of MMYM SERVICES, LLC

$375,000
3 Beds ⋅ 2 Baths ⋅ O6380339 MLS
Nestled within the highly desirable Chickasaw Trails neighborhood, this charming residence offers an overside corner lot, volume ceiling, a new roof (2026), tiled flooring, a spacious gourmet kitchen with a breakfast bar, and a large family room overlooking the backyard. Step into an inviting open floor plan featuring a spacious living and dining area with tile floors and vaulted ceilings. The kitchen is a chef’s delight, equipped with granite countertops and an eat-in nook. The thoughtfully designed split-bedroom layout ensures privacy in the primary suite. On the opposite side, you will find two additional bedrooms with a shower/tub combination. Enjoy Florida living on the screened patio overlooking the backyard, where you can relax and soak up the sun. Additional features include a two-car garage and washer/dryer hookups. The interior exudes elegance with stunning tile floor, while the outdoor space is equally impressive, featuring towering oak trees that provide shade and charm. Zoned for the highly sought-after Hidden Oaks Elementary School, it is just minutes away from Rio Pinar Country Club, where you can enjoy golf, social events, and more. Commute and travel are made easy with quick access to major highways, including 417, 408, and 528, connecting you seamlessly to Downtown Orlando, hospitals, Lake Nona, and MCO (Orlando International Airport).

8818 Reservation Drive, Orlando

Courtesy of FLORIDA REALTY INVESTMENTS

$289,000
O6296834 MLS
THIS LISTING IS FOR TWO PARCELS OF LAND BEING SOLD TOGETHER, ON EITHER SIDE OF SUBURBAN DRIVE IN CHICKASAW TRAILS AREA - CONVENIENT TO AIRPORT AND DOWN TOWN ORLANDO! NORTHERLY LOT IS OVER 3 ACRES; SOUTHERLY LOT IS NEARLY HALF ACRE! Where else can you find Gorgeous Private Wooded Acres so close to down town Orlando???? Location -- Location—Location --- Build your PERFECT wooded country estate! Past consultation with county indicated possible site for town-homes – or perhaps multi-home site, or worship center, adult day care, etc. Partially Fenced with sidewalk along Suburban Drive, check out the possibilities on this large vacant parcel. Seller may consider financing with good down - Let's Collaborate. Convenient to Hidden Oaks Elementary School. NOTE: Buyer to verify all information of import to Buyer. This Northerly parcel appears to have some ISOLATED wetland, and partial HIGH LANDS. This is isolated land (Meaning there is no runoff to any other property or body of water (no culvert under the road)) may lend an easier time for development for this Wooded Home Site. Convenient to Hidden Oaks Elementary School. NOTE: Buyer to verify all information of import to Buyer. OWNER IS DESIRING TO ACCOMPANY BUYER TO COUNTY MEETING(S) TO HELP PUSH YOUR PROJECT THROUGH. WE HAVE LETTER FROM COUNTY INDICATING BUILDABILITY, BUT FURTHER ENVIRONMENTAL STUDY IS NOT COMPLETE.

Suburban Drive, Orlando

Courtesy of REALTY GROUP SPECIALISTS, LLC

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