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

$249,000
3 Beds ⋅ 2 Baths ⋅ O6430896 MLS ⋅ 6265 BLDG.
Exquisite Condo in the Prime Area of LeeVista/Narcoosee, just steps from Lake Nona! The Gated Community of Horizons at Vista Lakes features a Resort-Style Swimming Pool, Tennis Courts, Picketball Court, Basketball Court, Playground, Dog Park and Nature Trails. If outdoor activities are part of your Lifestyle you will LOVE this Location. Freshly painted less than a yr ago, Ceramic Tile throughout and tons of Natural Light. NEWER AC, Split bedroom floorplan, boasting spacious bedrooms and walking closets. The 2nd Bedroom has its own private bathroom and huge walk in closet. Zoned for great schools, tucked in a private yet centric Location, conveniently located less than 10 minutes from the Orlando Airport. Walking distance to shopping! Call today to view it, dont miss out!

6265 Contessa Drive Unit 210, Orlando
$499,000
3 Beds ⋅ 3 Baths ⋅ O6430403 MLS
Welcome to this beautifully updated home that is truly move-in ready! Featuring a new roof (2020) and a new A/C (2025), this home has been thoughtfully renovated with todays modern style in mind. Within the last six years, all flooring has been replaced, with elegant porcelain tile throughout the downstairs living areas and stylish gray luxury vinyl flooring on the stairs and throughout the entire second floor. The stunning kitchen has been completely remodeled with sleek quartz countertops, modern cabinetry, and contemporary finishes. All bathrooms have also been tastefully upgraded, creating a fresh and elegant feel throughout the home. The interior and exterior showcase todays sought-after gray and white color palette, giving the home a clean, bright, and timeless appeal. Loft can be used for a 4th bedroom. Step outside to enjoy the beautiful, fenced backyard overlooking a peaceful pond perfect for relaxing, entertaining, or enjoying the Florida lifestyle. Residents will also enjoy an outstanding community lifestyle with resort-style amenities, including a sparkling community pool, a neighborhood park, tennis courts, and volleyball court- perfect for relaxing, staying active, or spending quality time with family and friends Conveniently located near the airport, hospitals, universities, major highways, shopping, and dining, this home offers both comfort and convenience. Don't miss this exceptional opportunity- this beauty is priced to sell and won't last long. Schedule your private showing today.

9773 Bennington Chase Drive, Orlando
$585,000
3 Beds ⋅ 3 Baths ⋅ O6426803 MLS
Welcome home! You're going to fall in love with this beautiful 3-bedroom, 2.5 bath home located in Oak Crest at Tivoli Woods. As soon as you enter, you'll appreciate the bright, spacious openness of this floor plan with formal and informal spaces downstairs and a large, remodeled kitchen, solid woods cabinets and new counter tops open to the family room for easy interaction with your family. Off of the family room is a covered porch overlooking your fenced backyard where you're sure to make many memories. Upstairs you'll find an open loft perfect for an office space or game room. Also, there's 2 bedrooms separated by a full bath to one side of the loft and just on the other is the laundry room. Just down from there you enter the spacious master bedroom with a tray ceiling, large walk-in closet with built-ins for organization and a large master bath with double sinks, tub and separate shower. There's also a community pool, playground and basketball court just a couple blocks from this home. This community also has a tennis court for more fun out in the Florida sun. All of this and convenient access to many major roadways, the Orlando International Airport, theme parks, downtown Orlando, Lake Nona and much more!

10114 Oak Crest Road, Orlando
$465,000
3 Beds ⋅ 2 Baths ⋅ O6418831 MLS
Welcome home to this beautifully renovated 3-bedroom, 2-bath home that is truly move-in ready! Nearly every detail has been thoughtfully updated, including a brand-new architectural ROOF (7/2026), new plumbing (7/2026), new WATER HEATER (7/2026), fresh interior and exterior paint (7/2026), a fully painted garage, new 5¼-inch baseboards, a new front door, stylish new light fixtures throughout, and new 2-inch faux wood blinds. The stunning kitchen is a true showstopper, featuring brand-new 36-inch cabinetry, gorgeous quartz countertops, brand-new stainless steel appliances, and designer finishes that perfectly combine style and functionality. Both bathrooms have been completely remodeled with contemporary fixtures and elegant finishes. Step outside to your private backyard oasis, complete with a brand-new wood privacy fence, fresh landscaping, and a new sprinkler system, creating the perfect setting for entertaining, relaxing, pets, or play. A separate air-conditioned backyard office provides the ideal flex space for working from home, a fitness room, art studio, hobby room, or private retreat. The detached shed has been thoughtfully converted into this comfortable, climate-controlled workspace, adding exceptional versatility to the property. The fully painted garage, complete with a newer garage door, offers a clean, finished appearance that's perfect for parking, storage, a workshop, or additional hobby space. This turnkey home showcases quality craftsmanship, modern finishes, and extensive upgrades throughout, offering peace of mind for years to come. Conveniently located near shopping, dining, schools, and major highways, this exceptional property is ready for its new owners. Don't miss this incredible opportunity to own a beautifully updated home with the added bonus of a private backyard office!

4040 Eagle Feather Drive, Orlando
$425,000
4 Beds ⋅ 2 Baths ⋅ O6429384 MLS
Are you looking for a Beautiful and Affordable Home in Orlando? This Home really does have it all with so many features including New Exterior Paint and Landscaping, New Fence, LVP Flooring, LED lighting, & Whole home water filtration system. Watch a movie in the awesome Theater room in-ceiling speakers, projector and theater screen. You will enjoy time with the family in the large enclosed lanai and backyard which is large enough for your pets and entertaining guests. Save Money with a super low HOA! The location is highly desirable and close to the 417, 408, Lee Vista and the airport. *All information is intended to be accurate but is not guaranteed. ** Theater Room / Fully Fenced Backyard / Large Lanai / New exterior paint / Landscaping / LOW HOA **

4613 Flatwood Lane, Orlando
$479,999
4 Beds ⋅ 3 Baths ⋅ O6429057 MLS ⋅ 6926 BLDG.
DON'T WAIT TO BUILD!!! Welcome to EverBe, Orlando's exciting new master-planned community offering resort-style amenities and an unbeatable location with quick access to SR 417 and SR 528. Enjoy miles of walking and biking trails, a state-of-the-art fitness center, resort-style pool, clubhouse, waterfront spaces, and a future town center. This beautifully designed Trailwood townhome features 4 bedrooms, 3 full bathrooms, a private courtyard, and a rear-entry 2-car garage. The open floor plan is perfect for entertaining, with a gourmet kitchen showcasing quartz countertops, stainless steel appliances, ample cabinetry, plus the refrigerator, washer, and dryer are all included. The first floor offers a bedroom and full bath, making it ideal for guests, a home office, or multigenerational living. Upstairs, the spacious owner's suite features a walk-in closet and a beautifully finished ensuite with dual vanities and a frameless glass shower. Two additional bedrooms, another full bath, and an upstairs laundry room complete the second floor. Additional upgrades include tile flooring throughout the main living areas, a whole-house water softener, and a location just a short walk from EverBe's incredible amenities. If you're looking for low-maintenance living in one of Orlando's newest communities, this home is a must-see. Schedule your private showing today!

6926 Reverie Park Avenue, Orlando
$400,000
3 Beds ⋅ 3 Baths ⋅ O6427156 MLS ⋅ 5133 BLDG.
Welcome home to this beautifully upgraded townhome where thoughtful design and modern finishes come together. From the moment you step inside, you'll appreciate the wood-look ceramic tile flooring throughout the main living areas, a stylish kitchen featuring granite countertops, a granite farmhouse-style sink, decorative tile backsplash, upgraded stainless steel appliances, pendant lighting, and plenty of space to gather with family and friends. The bathrooms continue the home's upgraded feel with quartz countertops, designer tile surrounds, and a seamless glass shower enclosure in the spacious primary suite. The primary bedroom also features a custom-designed walk-in closet with built-in shelving, providing exceptional organization and storage. Upstairs, upgraded carpet and premium padding add comfort throughout the second level. Step outside to enjoy your own private courtyard, perfect for relaxing or entertaining, along with the convenience of a rear-entry two-car garage. Located within the desirable Pinewood Reserve community, residents enjoy approximately 140 acres of wooded conservation, a resort-style community pool with cabana, playgrounds, and beautifully maintained common areas. Conveniently situated near major highways, you'll have easy access to Downtown Orlando, Orlando International Airport, Lake Nona Medical City, world-famous theme parks, beautiful Florida beaches, shopping, dining, and everyday conveniences. This move-in ready home offers the perfect combination of quality upgrades, low-maintenance living, and an outstanding location. Schedule your private showing today and discover everything this exceptional home has to offer.

5133 Sapling Sprout Drive, Orlando
$465,000
3 Beds ⋅ 2 Baths ⋅ O6428096 MLS
Welcome to this beautifully maintained home in the heart of Orlando! Featuring a desirable open-concept floor plan, this home offers a bright and inviting living space that's perfect for both everyday living and entertaining. The home's scenic front view overlooks a beautiful wooded area, creating a private, peaceful setting and enhancing the home's curb appeal. The stunning kitchen is the centerpiece of the home, boasting a large center island, beautiful upgraded cabinetry, quartz countertops, stainless steel appliances, and a spacious closet pantry. Designed with both style and functionality in mind. A versatile bonus room provides endless possibilities and can easily serve as a home office, playroom, media room, fitness space, or whatever best suits your lifestyle. Enjoy added peace of mind with a 2021 roof. Conveniently located with easy access to major highways, Orlando International Airport, Lake Nona, shopping, dining, and Orlando's world-renowned attractions, this home offers the perfect combination of comfort and convenience. Don't miss the opportunity to make this exceptional home yours!

3918 Watersend Drive, Orlando
$759,000
4 Beds ⋅ 3 Baths ⋅ O6428049 MLS
Welcome home to this 4 bedroom, 3 bath property with a den/study, situated on a coveted corner lot in the sought after Vista Lakes Village of Pembroke. Extensive private outdoor space and exceptional curb appeal greet you, with a landscaped front yard featuring a peaceful brick courtyard, tropical plants, and a fountain. Step through the ornate custom front doors into an open layout with porcelain tile flooring and floor to ceiling impact resistant windows that fill the space with natural light. Beyond the formal dining room and den off the foyer, the gorgeous kitchen features quartz countertops, stainless steel appliances (including a wine fridge), and storage that extends to the ceiling. A dining nook and a massive island with seating for a crowd complete the space. A stunning stone fireplace anchors the living room, which opens to the backyard. Outside, a covered patio runs the length of the property is perfect for lounging, entertaining, grilling, and games. The fully fenced backyard also includes a large sun drenched patio and lush yard. The main level offers a full bathroom and a den with additional built ins. Upstairs, all bedrooms feature beautiful Brazilian rosewood hardwood floors. The primary suite boasts French doors leading to a private breezy balcony and a custom walk in closet the size of another bedroom. The spa like ensuite includes his and her vanities, a modern free standing soaking tub, and a huge luxury shower with a rainfall shower-head. Guest rooms feature crown molding, with bathrooms offering the same luxury finishes found throughout the home. Ample storage in the laundry room and an immaculate 2 car garage round out this exceptional property. Residents of Vista Lakes Village of Pembroke enjoy private parks, playgrounds, and a community pool. You’ll be less than 3 minutes from Publix, 10 minutes from the airport, and close to Lake Nona Medical City. Easy access to highways 408, 528, and 417 puts Orlando and all the theme parks less than half an hour away!

6527 Bayboro Court, Orlando
$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
$780,000
4 Beds ⋅ 2 Baths ⋅ O6426729 MLS
Experience modern living in this beautifully upgraded home featuring contemporary design, quality finishes, and thoughtful enhancements throughout. The open concept layout showcases large format polished porcelain tile flooring all throughout the home, upgraded designer lighting, custom feature walls with modern finishes, and a stunning custom LED backlit mirror in the living area. The upgraded kitchen offers soft close cabinetry and drawers, stainless steel appliances, and a beautiful space designed for both everyday living and entertaining. The home continues to impress with custom closets throughout the bedrooms, including integrated lighting in the primary suite, upgraded bathroom vanities, remote controlled blackout blinds, a whole house water filtration system with alkaline drinking water, and a smart home security system with exterior cameras, smart lock, and app controlled garage access, and all appliances conveying for a truly move in ready experience. The epoxy coated garage floor adds another polished touch! The oversized backyard offers endless possibilities with ample space for a pool, outdoor kitchen, or custom outdoor living area. With extensive upgrades and high end finishes throughout, this home offers the opportunity to enjoy a move in ready property with modern design and elevated details.

6976 Rosy Sky Avenue, Orlando
$635,000
4 Beds ⋅ 3 Baths ⋅ O6427530 MLS
Welcome to this stunning **Pulte Homes Tower floor plan**, offering **4 bedrooms, 2.5 bathrooms**, and a spacious two-story design that perfectly balances comfortable everyday living with stylish entertaining. Barely lived in and meticulously maintained, this home truly feels **like new**. Step inside to an open-concept layout featuring a gorgeous designer kitchen with rich **maple cabinetry, granite countertops, upgraded faucets, stainless steel appliances, and an oversized center island** that overlooks the main living and dining areas—perfect for hosting family and friends. A private first-floor study provides the flexibility to serve as a home office, playroom, or even a fifth bedroom. Upstairs, you'll find all four bedrooms along with an expansive loft that's ideal for movie nights, a game room, or additional living space. The luxurious Owner's Suite is a peaceful retreat complete with a spacious walk-in closet and a private en-suite bath. Thoughtful upgrades throughout the home include **new stone landscaping**, a **new whole-home water filtration system (2025)**, **new ceiling fans throughout**, custom window treatments that remain, and beautiful custom paintings that convey with the home, adding a unique designer touch. Outside, enjoy one of the home's standout features—a **massive, fully fenced backyard** with endless possibilities for pets, play, entertaining, or creating your own outdoor oasis. Located in the highly desirable **Pinewood Reserve** community, residents enjoy a **low HOA of just $103 monthLY**, which includes an expansive resort-style community pool with cabana, playground, sidewalks, and beautifully maintained common areas. Situated just off **State Road 417 and Lee Vista Boulevard**, this home offers an incredibly convenient commute to Lake Nona Medical City, Orlando International Airport, downtown Orlando, shopping, dining, and major employment centers. If you've been searching for a move-in-ready home with modern finishes, generous living space, and an unbeatable location, this exceptional Pinewood Reserve home is one you won't want to miss!

5729 Wooden Pine Drive, Orlando
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