$382,506Average Value$242Average Price per Sq Ft90Homes For Sale
Secluded suburb in eastern Orlando
Ease and accessibility are the cornerstones of this eastern Orlando suburb. Locals can spend their time strolling along the palm tree-lined paved paths that connect the well-constructed subdivisions that cater to a wide range of prospective buyers. Spend the day golfing at Rio Pinar Golf Club or dive into the community at local eateries like Mecatos Bakery and Café or attend annual events like the District 1 Spring Festival in March. Residents here enjoy the benefits of a suburban enclave while reaping the benefits of a quick 10-mile commute into bustling downtown Orlando. Prospective buyers are attracted to the affordable price point, the well-rated school district and the nearby urban amenities at Lee Vista Promenade. “The Chickasaw community is surrounded by mature landscaping, giving residents an impression of a secluded suburb when the city is actually not far at all,” says Raul Otero Jr., Broker at Vista Home Realty with over 9 years of experience selling in the area.
Lakeside homes in Chickasaw offer beautiful views.
Chickasaw feels very suburban but Highway 408 makes downtown a few minutes away.
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Contemporary new-builds and Mediterranean coastal homes
Chickasaw features a range of housing options from traditional ramblers and newly-constructed contemporary styles to coastal homes with Mediterranean influences and multi-family townhouses. While a few townhouses can be found in Chickasaw, most residences are single-family properties built in the 1920s. Streets here are lined with paved sidewalks leading into compact cozy cul-de-sacs dotted with palm trees throughout the community. Chickasaw comprises several subdivision options from golf communities like Rio Pinar to gated 55 and older areas like Gulfstream Harbor and townhouses found in northern areas like Villa Valencia. Homeowners Associations are commonplace in this community but not universal. With a median sales price of $360,000, price points here can range from the mid $100,000s for a manufactured Ranch-style to upwards of $2,000,000 for a 5-bedroom Mediterranean-inspired coastal home in a gated community. Homes within gated communities are subject to increased price points here. Homes here often feature back patios or screened-in pools and are typically fronted by mid-sized lawns with mature landscaping and tropical flora. “The community is very established here with well-constructed homes and lower entry prices, providing the perfect opportunity for young families to enter the area,” says Otero.
Find a modern home with a large yard in Chickasaw.
Mediterranean Coastal style homes add a pop of color to the Chickasaw Neighborhood.
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High-marks at Orange County Public Schools
Students in Chickasaw can attend schools like Deerwood Elementary, Liberty Middle and Winter Park High School, all three of which earned a ranking of B-minus or higher from the educational review site, Niche. Deerwood Elementary School serves over 400 students with a student-teacher ratio of 14:1, while Liberty Middle School offers a variety of arts and electives like Latinos In Action (LIA), and empowers Latino youth in hopes of strengthening their communities. Winter Park High School offers an advanced curriculum with 26 Advanced Placement (AP) courses for higher education preparation. Private institutions like Orlando Christian Prep and Faith Christian Academy are also common here. Those interested in pursuing higher education can look to the University of Central Florida (UCF), which is just 10 miles from Chickasaw.
Deerwood Elementary School serves the Chickasaw community.
Welcome to the main entrance used for kids taking the bus to Liberty Middle School.
Winter Park High School is the home of the Wildcats.
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Tee-Up at the Rio Pinar Golf Club
Golf enthusiasts are in luck with Rio Pinar Golf nearby, which offers an 18-hole course and driving range for golfers to enjoy. The course has hosted championship PGA and LPGA tour events and regularly sees more than 200 golfers on a typical weekend. Visitors can practice their swing at the facility for daily rates or enroll in their golf academy for children ages 7 and older. Glide under the neon lights at Astro Skate of Orlando roller-skating rink, which offers daily open-skate times and private lessons for beginners. Quad or inline skate rentals are available and vary depending on the day starting at $6 on Mondays to $8 on Fridays. Other forms of community activity are centered around South Econ Community Park, which features basketball courts and picnic tables for outdoor dining on-the-go. Also, the recreational center here offers athletic programs and classes ranging from ancient martial arts to jazzercise. Parents also take advantage of the after-school care offered here for students in kindergarten through Grade 5.
Work on your swing at Rio Pinar Golf and Country Club in the heart of Chickasaw.
Rio Pinar Golf and Country Club offers public play and memberships in Chickasaw.
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Central Florida’s District 1 Spring Festival
In March, the District 1 Commissioner partners with the Orlando Police and Fire Departments in hosting the annual District 1 Spring Festival at Amhurst Park from 11:00 am to 3:00 pm. Visitors can visit vendor tents, enjoy free hot dogs and hamburgers and participate in activities like hayrides, face painting and bounce houses. It is also recommended to bring canned goods as the Second Harvest Food Bank will be accepting donations.
Shopping at Lee Vista Promenade
Residents here can shop at Lee Vista Promenade, which offers a variety of department stores and retailers to choose from, like Michaels, HomeGoods and Ross Dress for Less. Groceries and other everyday essentials are available at nearby stores like Walmart, Publix and Walgreens Pharmacy. When dining in the area, locals can begin their day at Mecatos Bakery and Café for specialty Colombian coffee and Latin-inspired pastries. For deep-fried French toast and Cuban-inspired comfort food, head to Jack and Mary's Restaurant. And check out Don Julio Mexican Kitchen Chickasaw for authentic Mexican cuisine, margaritas and a wide selection of vibrant cocktails.
Lee Vista Promenade provides Chickasaw residents with a variety of shopping options.
Not far from Chickasaw you will find the Lee Vista Promenade shopping center that locals love.
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Nearby healthcare and transportation around Chickasaw
Chickasaw relies on U.S. Route 408 and Curry Ford Road for easy access to downtown Orlando and neighboring areas like Cypress Springs and Lee Vista. Residents seeking public transit options can take the LYNX local bus service for trips in and around Chickasaw starting at $2.00 for adults one-way. Chickasaw riders can start their ride on bus route 3, which operates along South Chickasaw Trail and stops throughout the community. For those seeking to travel longer distances, the Orlando International Airport is only 8 miles away from Chickasaw. When seeking healthcare, residents are just 4 miles from AdventHealth East Orlando. Homes in Orange County may experience emissions from the Orange County Landfill located on Young Pine Road and are encouraged to report any odors to maintain upkeep.
The large Advent health Orlando Hospital is conveniently located in Chickasaw.
Taking the Lynx Bus connects Chickasaw to the rest of the Orlando area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Chickasaw neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Chickasaw
US
Homicide
3
4
Sexual Assault
3
4
Assault with Weapon
4
4
Robbery
4
4
Burglary
4
4
Motor Vehicle Theft
4
4
Larceny
3
4
Crime Score
3
4
Source: WhatIsMyCrimeRisk.com
Chickasaw Demographics and Home Trends
On average, homes in Chickasaw, Azalea Park sell after 49 days on the market compared to the national average of 54 days. The median sale price for homes in Chickasaw, Azalea Park over the last 12 months is $365,000, down 5% from the median home sale price over the previous 12 months.
Step into comfort, convenience, and effortless Florida living in this beautifully maintained home, perfectly positioned in the desirable Stonebridge Village community of East Orlando. From the moment you arrive, you’ll feel the welcoming energy and thoughtful flow of this spacious, light-filled floor plan — designed to make everyday living feel easy and enjoyable. The open living areas create a
Beautifully updated home in the established Shadow Bay community offering character, natural light, and extensive major upgrades for true move-in-ready living. Step inside to a dramatic recessed living area featuring cathedral ceilings, expansive high windows, and a cozy fireplace—creating a warm and inviting central gathering space. A striking interior live plant atrium brings abundant natural
Welcome to this unique manufactured home in the desirable Shadow Hills Family Community. This property offers 3 bedrooms and 2 bathrooms, including a 2 bedroom 1 bath main home plus a 1 bedroom 1 bath in law suite with its own kitchenette and private entrance. The home features vinyl flooring throughout, remodeled kitchen and bathrooms, and a laundry area in the shed. The in law suite also
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Experience an extraordinary confluence of generous space, refined privacy, and effortless convenience in this elegant single-family sanctuary, serenely poised on a picturesque half-acre along the storied 7th fairway of the scenic Rio Pinar Golf Course. A gentle veil of mature, whispering forestry preserves enchanting vistas while ensuring discreet seclusion—mere minutes from vibrant Downtown
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* Open kitchen overlooking great room * Primary bedroom at rear of home for added privacy * Walk-in closet at primary bedroom * Dual-sink vanity at primary bath * Stainless steel appliance package * Designer-selected light fixtures * Open floor plan * Split-bedroom layout * Spacious great room * Dedicated laundry room * WaterSense labeled faucets * ENERGY STAR certified home * Near local schools
* Open kitchen overlooking great room * Walk-in closet at primary bedroom * Powder bath * Spacious secondary bedrooms * Dual-sink vanity at primary bath * Stainless steel appliance package * Open floor plan * Spacious great room * Den * Dedicated laundry room * Expansive primary suite * ENERGY STAR certified home * Near local schools * Close to family friendly parks * Close to medical facilities
* Open kitchen overlooking great room * Primary bedroom at rear of home for added privacy * Walk-in closet at primary bedroom * Dual-sink vanity at primary bath * Garage access from laundry room * Stainless steel appliances * Open floor plan * Split-bedroom layout * Spacious great room * Walk-in kitchen pantry * Dedicated laundry room * ENERGY STAR certified home * Near local schools * Close to
* Open floor plan * Primary suite at rear of home for added privacy * Oversized walk-in closet at primary bedroom * Dual-sink vanity at primary bath * Low-VOC interior paint * Stainless steel appliance package * Split-bedroom layout * Spacious great room * Walk-in kitchen pantry * Den * Dedicated laundry room * ENERGY STAR certified home * Near local schools * Close to family friendly parks *
Available to view Jan. 15th. Photos coming soon! You'll love this adorable 3 bedroom, 2 bathroom half of a duplex that has been remodeled and ready to for you! The kitchen has room for a large dining table and has beautiful white cabinets and stone counters. The kitchen overlooks the large family room with vinyl flooring and sliding doors out to the back yard. The bedrooms have carpeting and
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Well-Maintained Rental in Convenient Orlando LocationThis well-kept unit is located in an established Orlando community, offering comfort, functionality, and a convenient location close to everyday necessities.The home features a practical layout with inviting living spaces, ideal for long-term tenancy. Set within a quiet community, it provides a pleasant living environment while
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Upon entering this lovely 4-bedroom, 2-bathroom home, you will first notice the plank style wood look luxury vinyl flooring and fresh paint throughout. Both bathrooms have been updated, including modern vanities and tastefully tiled showers. There are 1,593 total square feet, with 1,193 square ft under air. This home also offers a newer AC system, one-car garage with washer and dryer hook-ups,
Discover Avida, where style meets comfort and convenience. Our one-, two-, and three-bedroom apartment homes feature spacious living areas, gourmet kitchens with stainless steel appliances, and your choice of two stylish finish packages. Just beyond your door, enjoy resort-style living with our pool surrounded by comfortable seating, loungers, and cabanas. Entertain friends and family with our
Welcome to your next extraordinary chapter in living — a resplendent four-bedroom, three-bathroom residence nestled within one of Orlando's most coveted neighborhoods, now available for lease. Step beyond the striking stone facade and lush palm-lined landscaping into an open, airy split floor plan bathed in natural light. Wood tile floors guide you through seamlessly connected living and dining
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Discover effortless living in this elegant second-floor 1 Bedroom condo at Villa Valencia. This unit features an open floor plan that blendsfunctionality with style, starting from the welcoming hallway to the cozy dining area and modern kitchen, perfect for culinary exploration. The living room, drenched in natural light, opens to a peaceful covered lanai — ideal for both relaxation and
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