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 family-friendly atmosphere and lush landscapes, Chickasaw is a hidden gem that offers a perfect blend of suburban tranquility and urban convenience.

Situated in Orange County, Chickasaw is ideally located just a short drive from Orlando's world-famous attractions, including Walt Disney World, Universal Studios, and SeaWorld. This makes it not only a fantastic place to live but also an exciting destination for visitors. The community boasts a rich tapestry of parks, recreational facilities, and scenic walking trails, perfect for outdoor enthusiasts and families alike. The nearby Lake Underhill Park offers serene views and ample space for picnics, jogging, and enjoying the beautiful Florida weather.

Chickasaw is also known for its strong sense of community. Residents enjoy a variety of local events and gatherings that foster connections among neighbors. The area is served by highly-rated schools, making it an ideal location for families looking to provide their children with quality education.

For those who love shopping and dining, the nearby Waterford Lakes Town Center offers a delightful mix of retail stores, restaurants, and entertainment options. Whether you're in the mood for a casual meal or a night out, you'll find plenty of choices to satisfy your cravings.

In Chickasaw, you’ll find more than just a place to live; you’ll discover a community that embraces the spirit of Orlando while offering a peaceful retreat from the hustle and bustle. Explore the charm of Chickasaw, where your dream home awaits!

Newest Listings in Orlando/Chickasaw

8609 Crossbay Drive, Orlando
$390,000
3 Beds ⋅ 2 Baths ⋅ O6448980 MLS
Welcome to your dream home in the Chickasaw Oaks subdivision, where an exceptional three-bedroom, two-bathroom residence awaits you. This charming residence provides the ideal space for relaxation, unwinding, or entertaining guests. With approximately 1,615 square feet of living space, this home is thoughtfully designed to maximize functionality and comfort. You will find a spacious dining room perfect for the entire family. The well-appointed kitchen overlooks the family room and features granite countertop, 42-inch kitchen cabinets and stainless-steel appliances. The inviting family room is perfect for Sunday football games, and the kitchen is designed for effortless entertaining. The split floor plan ensures privacy for everyone, featuring an expansive master suite with a generous closet and an en-suite bathroom complete with dual shower space and refined finishes. Each additional bedroom offers comfortable and adaptable living space to suit your evolving needs. The home also includes a dedicated relaxation room and an indoor laundry room, enhancing the practical and functional layout. Enjoy Florida’s beautiful climate year-round on the screened patio with a spa, perfect for hosting gatherings or unwinding in a serene setting. Attention to detail is evident throughout this home, combining durability and style with modern amenities that cater to a contemporary lifestyle. This neighborhood is friendly atmosphere, and convenient access to an array of amenities. From local parks and recreational facilities to schools and shopping centers, everything you need is within easy reach. Don't miss this opportunity to own a piece of Chickasaw Oaks paradise. Conveniently located near Vista Lakes, Lake Nona (Medical City), MCO (Orlando International Airport), 528, and 417 Expressway. Just minutes from many major attractions and theme parks.

8609 Crossbay Drive, Orlando
8352 Lake Amhurst Trail, Orlando
$379,900
3 Beds ⋅ 2 Baths ⋅ O6451686 MLS
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 8352 Lake Amhurst Trail, a charming, well cared for single-story home featuring 3 bedrooms, 2 bathrooms, and approximately 1,748 square feet of living space in the desirable Vista Lakes community of Orlando. Nestled in the established Amhurst neighborhood, this home offers a comfortable setting for everyday living and entertaining. Step inside to discover a functional split layout with inviting living spaces, a kitchen, and a dining area ideal for everyday meals and gatherings. The bedrooms provide comfortable accommodations and flexibility for guests or a home office. Additional features include an attached two-car garage and a welcoming front porch. Step outside to the covered patio, perfect for relaxing, enjoying the Florida weather, or entertaining guests. Residents of Vista Lakes enjoy access to community amenities, including swimming pools, a clubhouse, fitness center, tennis and basketball courts, playgrounds, parks, and scenic walking trails. The nearby Amhurst Park also offers recreational areas and outdoor activities. Conveniently located in Southeast Orlando, this home provides easy access to nearby schools, shopping, dining, and entertainment. With close proximity to Lee Vista Boulevard, State Road 417, State Road 528, and Orlando International Airport, commuting throughout Central Florida is convenient. Offering a combination of comfortable living, community amenities, and an excellent location, this home is a wonderful opportunity to enjoy the Orlando lifestyle. Recent updates include a roof replacement in 2019, HVAC system in 2021, and hot water heater in 2021.

8352 Lake Amhurst Trail, Orlando
10938 Felicity Alley, Orlando
$510,000
3 Beds ⋅ 3 Baths ⋅ S5160073 MLS
Virtually Staged. Better then NEW !!! Very well maintain 3 bedrooms, 2 bathrooms Home with Loft in Desire EverBe Community!! The first floor is great for entertaining, with its combined living room , kitchen, powder room, and gorgeous Lighthouse wood-look luxury vinyl plank flooring. The kitchen features a center island, storage pantry, stainless steel Whirlpool appliances, 42" soft close Stone Gray cabinets and Lyra quartz countertops. The second floor offers privacy and space for everyone with the owner’s suite, two additional bedrooms, the second bathroom, the laundry room and loft. Your master bedroom features a walk-in closet, bathroom with a private water closet, linen closet, walk-in shower and dual sink quartz-topped Stone Gray vanity. EverBee community close to main roads and all activities. This lifestyle community offering 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. EverBe - everything home should ever be!

10938 Felicity Alley, Orlando
3626 Benson Park Boulevard, Orlando
$479,000
3 Beds ⋅ 2 Baths ⋅ R4912202 MLS
Welcome to your beautiful home with everything you are looking for with comfort, quiet and convenience! Prime location ready to move into now with quick access to 417, 408 and Beeline and just minutes from grocery, shopping, and dining. Very sought after location for convenience getting around Orlando easily. Situated in a peaceful community known for its family safety and neighbors. This 3 bedroom/2 bath home offers comfortable single-story living, a two-car garage and park setting next door so only neighbors on one side! Beautiful conservation woods give back yard views inviting you to relaxing time on your lanai. Great open plan layout flows easily with family room and kitchen. Call or text to view this home and make it yours today! Staged photos.

3626 Benson Park Boulevard, Orlando
5803 Cheshire Cove Terrace, Orlando
$615,000
4 Beds ⋅ 4 Baths ⋅ O6451153 MLS
priced to sell AS IS, need personal cosmetic touch to make it stunning home, located in highly desirable Vista Lake - Avon community, four bed /3 full bath, with powder room, features double open stairs with high ceilings, master suit and laundry in first floor, large living/dining area, spacious kitchen/family room, patio with pond view to relax and entertain with Family and guest, upstairs come with large loft, one bedroom with bathroom attached, and shared bathroom for other two bedrooms, BONUS -easy access to SR417/528, Lake Nona medical center, tourist attraction/ UCF college/Orlando international airport / beaches , community features pool, basketball/tennis court, club house, fitness center, play ground

5803 Cheshire Cove Terrace, Orlando
8509 Lyonia Drive, Orlando
$385,000
4 Beds ⋅ 2 Baths ⋅ O6451431 MLS
Are you in the market looking to purchase a Single-Family Residence in Orange County Florida? I recommend you have 8509 Lyonia Drive on your list and make it a must-see property because of its size, a quarter acre lot with an oversized backyard, no homeowner's association (HOA), fenced backyard with fruit trees, and the best part of it no rear neighbor. It also boasts of two sheds, a screened-in porch and a covered patio with concrete floor. Driving on Chickasaw Trail to the property feels like you are on a country road. The location of the property gives you easy access to shopping centers, major highways and MCO Orlando International airport. The property in the public record shows as a 3/2. However, it is being listed as a 4/2 because the garage was converted into a fourth bedroom. As per the Seller, the property was purchased as a 4/2. If you are looking for an extra bedroom, here it is for you. The family room has a wood-burning fireplace. The septic tank was pumped out in March 2026, electrical panel was replaced in June 2021, and roof was replaced in May 2021. The floor covering for the whole house is ceramic tiles and most of the wall paneling with laminate. Property comes with video security system. Primary and secondary bathrooms are ungraded. The kitchen has wood cabinets, laminate countertops with backsplash. As you have read, this property offers you comfort and convenience so come on in and take a tour!

8509 Lyonia Drive, Orlando
3805 Running Water Drive, Orlando
$439,000
3 Beds ⋅ 2 Baths ⋅ O6450836 MLS
Virtually Staged. Welcome to this beautifully maintained 3-bedroom, 2-bath home in Orlando’s established Chickasaw Trails community. Offering approximately 1,940 square feet of living space, this home blends comfortable gathering areas with a desirable split floor plan. Separate formal living and dining rooms provide flexibility for entertaining or everyday living, while the updated kitchen features granite countertops and opens to the family room, keeping everyone connected. The primary suite features wood flooring, a walk-in closet, and an ensuite bathroom with a double vanity, separate walk-in shower, and garden tub. Two additional bedrooms and a full bathroom occupy the opposite side of the home, providing added privacy. Ceramic tile flooring throughout the rest of the home offers a cohesive look and easy maintenance. Unwind on the enclosed porch or enjoy the fenced backyard, where mature trees create an inviting setting for outdoor gatherings and quiet afternoons. Major improvements include a roof replaced in 2024, a water heater replaced in 2021, and windows replaced in 2018. A two-car garage adds convenience and storage. Enjoy convenient access to UCF, the Orlando VA Medical Center, AdventHealth facilities, Orlando International Airport, and downtown Orlando, along with nearby shopping and dining. Orlando’s renowned attractions and entertainment destinations are also within driving distance. Discover the space, comfort, and location this home has to offer. Schedule your private showing today!

3805 Running Water Drive, Orlando
5975 Winchester Isle Road, Orlando
$650,000
5 Beds ⋅ 3 Baths ⋅ O6450633 MLS
Welcome to this stunning home in the highly sought-after Vista Lakes community! With 5 bedrooms, 3 bathrooms, and approximately 3,007 sf of living space, 5975 Winchester Isle Rd offers a perfect blend of modern comfort and resort-style lifestyle The generous floor-plan features a spacious downstairs guest bedroom (ideal for mother-in-law suite or multi-gen living) and a newly remodeled first floor bathroom. Upstairs, the master suite impresses with dual walk-in closets, his & hers vanities, garden tub and separate shower stall — all designed for everyday luxury. Gourmet kitchen boasting 42” cabinetry, double ovens, stainless steel appliances and open-flow into family and dining spaces makes entertaining effortless. Gorgeous water-view from the second-floor porch invites quiet mornings or peaceful evenings overlooking the pond. The oversized backyard is ready for your private pool oasis (pool bathroom already in place!) and features a covered lanai – perfect for Florida outdoor living and entertaining. Located in a vibrant amenity-rich community: resort-style pool, tennis and basketball courts, fitness center, sidewalks, and close proximity to Lake Nona Medical City, major Orlando attractions and easy access to Orlando International Airport. Don’t miss the opportunity to call this move-in ready, beautifully maintained home your own. Contact us for a private showing today!

5975 Winchester Isle Road, Orlando
3701 Beaver Ridge Drive, Orlando
$490,000
3 Beds ⋅ 3 Baths ⋅ O6444062 MLS
Professional photos coming soon. Make the most of Florida living in this Chickasaw Trails POOL home on a spacious corner lot. A screened saltwater pool and spa take center stage in the backyard, ready for refreshing swims and relaxing evenings. The expansive covered lanai offers plenty of space for outdoor dining, lounging, and entertaining. Fencing and established privacy hedges create a secluded feel in the backyard, while a storage shed provides room for tools and outdoor essentials. Inside, the great room welcomes you with a soaring two-story vaulted ceiling and numerous windows that fill the space with natural light. A separate dining room provides a dedicated setting for meals and gatherings. The kitchen features stainless steel appliances and a breakfast bar, while the adjacent breakfast nook enjoys views of the backyard through a bay window. The first-floor primary suite includes a spacious walk-in closet. Its en-suite bathroom features dual sinks, a marble countertop, a generous walk-in shower, and a soaking tub. Direct access to the lanai makes pool days more convenient. Upstairs, an open loft overlooks the great room and offers flexible space for an office, reading nook, or additional living area. Two additional bedrooms each feature a walk-in closet and share an upstairs bathroom. A separate laundry room includes the washer and dryer. A two-car garage completes the home. Major updates include the roof (2022), A/C (July 2026), water heater (December 2023), and interior and exterior electrical panels (September 2022). The pool was resurfaced in 2020, the washer and dryer were replaced in May 2023, and the dishwasher and microwave were replaced in 2026. Established Chickasaw Trails offers a community playground, low HOA fees, and no CDD fees. Trail access connects the neighborhood to South Econ Community Park and Recreation Center. Nearby SR 417 provides convenient connections to Lake Nona, Orlando International Airport, UCF, and Valencia College, with shopping and dining close by.

3701 Beaver Ridge Drive, Orlando
3548 Benson Park Boulevard, Orlando
$389,000
3 Beds ⋅ 2 Baths ⋅ O6449166 MLS
A wooded conservation backdrop, an established neighborhood, and the appeal of East Orlando suburban living. Welcome to this home in the Young Pine community, where a natural setting complements everyday comfort and convenience. This three-bedroom, two-bathroom home offers comfortable single-story living, a two-car garage, and an outdoor setting designed for relaxation and everyday enjoyment. The spacious backyard features open green space, mature landscaping, and a wooded conservation backdrop. A patio extends your living space outdoors, creating an inviting setting for morning coffee, weekend gatherings, or simply unwinding at the end of the day. Inside, the home offers a comfortable, functional layout that accommodates the rhythm of everyday life, from quiet mornings and relaxed evenings to entertaining friends and gathering around the table. Three bedrooms provide flexibility for a variety of needs, while the single-story design creates a natural connection between indoor comfort and outdoor living. Beyond the property, enjoy the appeal of East Orlando suburban living, where established neighborhoods and residential surroundings create a welcome retreat from the busier parts of Central Florida. Located near the Lake Nona area with convenient access to major roadways, shopping and dining at Waterford Lakes, Orlando's theme parks, Downtown Orlando, and Orlando International Airport are all within a manageable drive. It's a location that has the comfort of suburban living while keeping the area's entertainment, recreation, and everyday conveniences within reach. For buyers exploring homes for sale in East Orlando, this property brings together comfortable single-story living, generous outdoor space, a patio, and a conservation backdrop in an established East Orlando community. Come experience the setting, explore the possibilities, and discover how this East Orlando home could complement your lifestyle. Schedule your private showing.

3548 Benson Park Boulevard, Orlando
9715 Brown Burrow Street, Orlando
$539,900
4 Beds ⋅ 2 Baths ⋅ O6448991 MLS ⋅ 9715 BLDG.
Welcome to Pinewood Reserve! This beautifully upgraded, move-in-ready single-story home offers 4 bedrooms, 2 bathrooms, a 2-car garage, and no rear neighbors, combining modern finishes with privacy and an exceptional Orlando location. The owners thoughtfully selected numerous upgrades throughout the home, including gray wood-look ceramic tile flooring, tray ceilings in the main living area, and a built-in gourmet kitchen featuring modern stainless steel appliances. Additional upgrades include a utility sink in the laundry room with a modern washer and dryer, an upgraded elevation, and extensive pavers enhancing the driveway, extended front walkway, and backyard. Step outside and enjoy one of the home's standout features—no rear neighbors and peaceful views of the conservation area, creating a private and tranquil setting to enjoy your backyard. Pinewood Reserve offers wonderful community amenities, with the community pool and playground within walking distance of the home. The location is equally impressive, with convenient access to SR-417 less than two minutes away, providing easy connectivity throughout Central Florida, and Orlando International Airport less than 10 minutes away. With its combination of upgrades, privacy, community amenities, and convenient location, this home is ready for its next owner. Schedule your private showing today and come see everything this Pinewood Reserve home has to offer!

9715 Brown Burrow Street, Orlando
5742 Essex Isle Drive, Orlando
$449,900
4 Beds ⋅ 2 Baths ⋅ O6437464 MLS
Welcome! This one-story, move-in-ready home features 4 bedrooms and 2 bathrooms, with a brand-new roof, HVAC system, and water heater, providing peace of mind for years to come. Additional updates include fresh interior and exterior paint, new carpet, and new granite countertops in the kitchen. Inside, an open floor plan connects the living spaces beautifully, with the vaulted ceiling extending throughout the main living areas, creating a light and airy atmosphere. Tile flooring flows through key spaces, offering a durable foundation for daily living, while new carpet in each bedroom delivers maximum comfort. The kitchen showcases new granite countertops, along with an island, generous countertop space, and a breakfast bar that invites both cooking and gathering no matter the occasion. With major systems like the roof, HVAC, and water heater recently replaced, as well as multiple other major aspects, you can move in with confidence, knowing you can simply unpack and start enjoying your new space right away. Not only is this home move-in-ready, but the community offers a host of amenities, including resort-style pools, a clubhouse, fitness center, tennis/pickleball courts, basketball courts, baseball/softball field and batting cages, multiple parks/green spaces, dog park, and playground. Schedule your private showing today!

5742 Essex Isle Drive, Orlando
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