12,877

Chickasaw Homes

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  • /60

    $649,000

    • 5 Beds
    • 3 Baths
    • 3,338 Sq Ft

    2026 Winding Oaks Dr, Orlando, FL 32825

    Nestled within the Premiere Gated Community of the Preserve at Rio Pinar lies an exquisite opportunity for homeownership. Offering both tranquility and privacy, this immaculately maintained home is all on one story and was constructed on a prime conservation, cul-de-sac lot in the back of the neighborhood, with lush woods beyond the backyard. With 5 bedrooms, 3 baths, and soaring 12ft ceilings,

    Agent Photo

    Bill Bliss

    EXP REALTY LLC

    (321) 346-0827

    2026 Winding Oaks Dr, Orlando, FL 32825
  • /11

    $1,600 per month

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    8026 Brocatel Ct, Orlando, FL 32822

    Apartment of 2 bedrooms and 1 bath for rent located in the beautiful community of Royal Manor Estates. Tile thorough out, refrigerator and stove in the pictures will be replaced with a stainless steel.

    Agent Photo

    Agnes Serrano

    ALIGN RIGHT REALTY WESTSHORE

    (321) 334-3181

    8026 Brocatel Ct, Orlando, FL 32822
  • /2

    $435,000 Sold Jul 21, 2025

    • 1,959 Sq Ft
    • $222/SF
    • 87 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1991

    8509 Black Mesa Dr, Orlando, FL 32829

    This property qualifies for a credit up to $6,750 through the seller's preferred lender & seller may consider buyer concessions if made in an offer~ Fantastic opportunity in East Orlando’s Chickasaw Trails community for a 4-bedroom, 2-bath single story home on a large .20 ACRE LOT with a NEWER ROOF (2022), UPDATED WATER HEATER and a huge Florida room on the back of the home for additional

    Jennifer Wemert WEMERT GROUP REALTY LLC

    8509 Black Mesa Dr, Orlando, FL 32829
    • /2

      Est $346,084 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,292 Sq Ft

      7749 Fort McHenry Ct, Orlando, FL 32822

      7749 Fort McHenry Ct, Orlando, FL 32822
  • /36

    $374,999

    • 3 Beds
    • 2 Baths
    • 1,506 Sq Ft

    324 River Chase Dr, Orlando, FL 32807

    Welcome to 324 River Chase Dr—a beautifully maintained 3-bedroom, 2-bathroom home in the highly desirable River Chase community, just minutes from downtown Orlando! This gem comes with fully owned solar panels, offering immediate energy savings and eco-friendly living from day one. Just one look and you'll fall in love with this charming home in East Orlando's Rive Chase Subdivision.

    Agent Photo

    Waseem Saedi

    LA ROSA REALTY PREMIER LLC

    (321) 343-4710

    324 River Chase Dr, Orlando, FL 32807
  • /46

    $1,666 - $3,579 per month

    Avida

    1-3 Beds

    1000 Avida Village Cir, Orlando, FL 32825

    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

    1000 Avida Village Cir, Orlando, FL 32825
  • /2

    $395,000 Sold Jul 19, 2025

    • 1,662 Sq Ft
    • $238/SF
    • 5 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    8111 Lianna Dr, Orlando, FL 32822

    COMPLETELY REMODELED AND RENOVATED IN APRIL-MAY 2025 AND PRICE TO SELL! This single family home has gone through a detailed remodeling process to allow well appointed modern and functional spaces throughout the house. A brand new modern kitchen featuring 42” white shakers upper cabinets with quartz countertops and base cabinet drawers. Boasting an EIGHT feet island with a large single bowl

    Anna Russu RUSSU REALTY & ASSOCIATES PA

    8111 Lianna Dr, Orlando, FL 32822
    • /2

      Est $403,753 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,516 Sq Ft

      8080 Elsee Dr, Orlando, FL 32822

      8080 Elsee Dr, Orlando, FL 32822
  • /25

    $160,000

    • 1 Bed
    • 1 Bath
    • 615 Sq Ft

    8213 Claire Ann Dr Unit 108, Orlando, FL 32825

    Welcome to 8213 Claire Ann Drive—your ideal home base in the heart of East Orlando. This beautifully maintained 1-bedroom, 1-bathroom ground-floor condo offers the perfect blend of comfort, value, and unbeatable location. Situated just minutes from Valencia College East Campus, University of Central Florida (UCF), and with easy access to FL-417, commuting and exploring all that Central Florida

    Agent Photo

    Tim Veigle

    WATSON REALTY CORP

    (321) 252-7064

    8213 Claire Ann Dr Unit 108, Orlando, FL 32825
  • /11

    $2,075 per month

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft
    • House for Rent

    7864 Sagebrush Place, Orlando, FL 32822

    Ready for move in on August 9th, 2025!!!! Enjoy this lovely 3 bedroom 2 bath home in the beautiful community of Village at Curry Ford Woods. When you walk through the door and you are greeted with natural light and an amazing floor plan. The great room serves as a living/dining combo which has been fully tiled. The back yard is already fenced in, so sit back and relax while you enjoy the Florida

    Steve Simpson 407 PROPERTIES

    7864 Sagebrush Place, Orlando, FL 32822
  • /2

    $399,000 Sold Jul 18, 2025

    • 1,666 Sq Ft
    • $239/SF
    • 23 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1980

    8652 Savory Dr, Orlando, FL 32825

    Welcome to this stunning pool home in the highly sought-after East Orlando area! Located in a community known for its top-rated schools, this spacious residence offers a versatile bonus room and a dedicated home office—ideal for work, study, or play. The home features a 3-year-old roof (MAR 2022), offering peace of mind and added value. Step outside to your private backyard oasis with a sparkling

    Jose Martinez Rivera LLC EXP REALTY LLC

    8652 Savory Dr, Orlando, FL 32825
    • /44

      Est $188,817 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft

      8203 Sun Spring Cir Unit E1, Orlando, FL 32825

      8203 Sun Spring Cir Unit E1, Orlando, FL 32825
  • /57

    $559,900 Pending

    • 5 Beds
    • 3 Baths
    • 2,837 Sq Ft

    1055 N Chickasaw Trail, Orlando, FL 32825

    Discover the freedom and flexibility you’ve been searching for—NO HOA, NO CDD, and a spacious, versatile layout that opens the door to endless possibilities. Whether you're accommodating extended family, renting to college students, or starting an assisted living facility, this unique property is ready to meet your vision.With 5 full bedrooms and 3 full bathrooms, the home includes a

    Agent Photo

    Carlos Diaz

    COLLECTIVE GROUP REALTY, CORP

    (321) 450-4297

    1055 N Chickasaw Trail, Orlando, FL 32825
  • /30

    $1,442 - $3,743 per month

    Lakes at 408

    1-2 Beds

    7960 Pine Crossings Cir, Orlando, FL 32807

    Sink into the comfort of a laidback lifestyle at Avisa Lakes in East Orlando, a community offering one and two-bedroom apartments for rent in a relaxed, garden-style community. Inside your home, a spacious layout greets you with contemporary wood-inspired vinyl flooring and a variety of features that will carry you through your daily routine. Cook in a fully equipped kitchen or unwind with movie

    7960 Pine Crossings Cir, Orlando, FL 32807
  • /2

    $282,000 Sold Jul 18, 2025

    • 1,249 Sq Ft
    • $226/SF
    • 63 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1990

    3026 Pigeon Hawk Ct, Orlando, FL 32829

    Welcome to 3026 Pigeon Hawk Ct located in the heart of Orlando, FL. This 1⁄2 duplex, 2 bedrooms and 2 bathrooms is a perfect home for first-time homebuyers, or investors looking to add to their portfolio. The home features an eat-in kitchen space, with a separate living room/ dining room combo, and a generous size pantry. The home boasts two generous size bedrooms. Upstairs is where you find the

    Milscent Julssaint SIERRA REALTY GROUP LLC

    3026 Pigeon Hawk Ct, Orlando, FL 32829
    • /46

      Est $235,173 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,467 Sq Ft

      953 Courtyard Ln Unit 41, Orlando, FL 32825

      953 Courtyard Ln Unit 41, Orlando, FL 32825
  • /25

    $486,000

    • 4 Beds
    • 2 Baths
    • 2,014 Sq Ft

    4021 Eagle Feather Dr, Orlando, FL 32829

    Welcome to this beautifully refreshed home that blends modern updates with everyday functionality. Step inside to discover an open and inviting floor plan, freshly painted throughout with a stylish accent wall that adds a designer touch to the front room. Enjoy natural light paired with room-darkening, remote-control blinds on the sliding glass doors off of the family room —ideal for comfort and

    Nicole Dege REDFIN CORPORATION

    4021 Eagle Feather Dr, Orlando, FL 32829
  • /17

    $2,067 per month

    • 3 Beds
    • 2 Baths
    • 1,278 Sq Ft
    • House for Rent

    7931 Merrimac Cove Dr, Orlando, FL 32822

    3Bed/2Bath in Curry Ford Area Available Now!Priced Low, Call Now, Very Clean Property, Move in Ready, 1 Car Garage, Pond View, No Rear Neighbors, Large Backyard, Backyard Patio, Huge Master Suite, Living and Dining Rooms, Walk in Closet, Granite Countertops, Upgraded Kitchen, Eat in Kitchen, Luxury Vinyl Plank Flooring Throughout, Ceiling Fans in Many Rooms, JUST 20 MINUTES To The Airport,

    Jay Myers ORLANDO REALTY & PROPERTY MGNT

    7931 Merrimac Cove Dr, Orlando, FL 32822
  • /2

    $188,000 Sold Jul 17, 2025

    • 1,120 Sq Ft
    • $168/SF
    • 6 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1984

    954 Courtyard Ln Unit 52, Orlando, FL 32825

    Are you ready to live in an Amazing Condominium Community? Well, you have found it!! Welcome to, The Club at Orlando and, 954 Courtyard Lane, Unit #52. This community is conveniently located within minutes of Expressways, UCF, Valencia College, Siemens Energy, Lockheed Martin, shopping, schools, and restaurants. You DO Not want to miss out on this little gem of a property! This lovely 2 bedroom,

    J. Hope Carter Snoap FUTURE HOME REALTY INC

    954 Courtyard Ln Unit 52, Orlando, FL 32825
    • /26

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,064 Sq Ft

      8215 Sun Spring Cir Unit 11, Orlando, FL 32825

      8215 Sun Spring Cir Unit 11, Orlando, FL 32825
  • /25

    $417,000

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft

    8453 Mattituck Cir, Orlando, FL 32829

    One or more photo(s) has been virtually staged. East Orlando Pool Home! 2024 ROOF!! NO HOA!!! This 3-bedroom, 2-bath home features an additional flex room, perfect for a 4th bedroom or home office. The tile flooring throughout is not only stylish but also low-maintenance and ideal for keeping cool during Florida summers. The primary ensuite offers direct access to the pool and backyard through a

    Sheri Malin REDFIN CORPORATION

    8453 Mattituck Cir, Orlando, FL 32829
  • /15

    $1,196 - $2,891 per month

    The Woodlands Apartments

    1-3 Beds

    604 Laurel Cove Ct, Orlando, FL 32825

    The Woodlands features gorgeous East Orlando apartments in the heart of the Sutton Ridge neighborhood. Enjoy coming home to our beautifully designed apartments in Orlando, FL with the area's best dining, shopping, and recreation right at your fingertips. Our apartments feature a variety of spacious one, two, and three bedroom floor plans with fully-equipped kitchens and screened balconies or

    604 Laurel Cove Ct, Orlando, FL 32825
  • /2

    $405,000 Sold Jul 16, 2025

    • 1,334 Sq Ft
    • $304/SF
    • 81 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1991

    3043 Autumn Run Ct, Orlando, FL 32822

    Stunning Pool Home in Autumn Run – Updated, Move-In Ready, and Energy Efficient with Paid-Off Solar Panels! Welcome to 3043 Autumn Run Court, a meticulously maintained 3-bedroom, 2-bathroom pool home, perfectly situated on a premium cul-de-sac lot in the highly sought-after Autumn Run community. Nestled against a tranquil conservation area with no rear neighbors, this home offers the ultimate

    Ryan Leitter CHARLES RUTENBERG REALTY ORLANDO

    3043 Autumn Run Ct, Orlando, FL 32822
    • /15

      Est $490,394 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,067 Sq Ft

      2730 Arbor Trail Way, Orlando, FL 32829

      2730 Arbor Trail Way, Orlando, FL 32829
  • /33

    $520,000

    • 5 Beds
    • 4.5 Baths
    • 2,630 Sq Ft

    7551 Bear Claw Run, Orlando, FL 32825

    One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged.PRICE IMPROVEMENT – NOW $520,000 | MOTIVATED SELLER!Beautifully updated 5BD/4.5BA home in Chickasaw Place, East Orlando! Over 2,500 sq. ft. with a smart layout ideal for families, multi-gen living, or rental income. Primary suite downstairs, two renovated baths with bidets (2023), and major

    Sheyla Apuy KELLER WILLIAMS ADVANTAGE III

    7551 Bear Claw Run, Orlando, FL 32825
  • /11

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,132 Sq Ft
    • Townhouse for Rent

    Unlisted Address

    Charming 3-Bedroom Duplex in Rio Pinar Lake with Water view! Featuring ceramic tile flooring throughout, a spacious living and dining area, and ceiling fans in various rooms - this home is truly designed for easy living. Enjoy the outdoors with a screened-in back patio perfect for relaxation or entertaining. Living in Rio Pinar Lakes means that there is always something to do nearby! Additional

    Ingrid Desantiago VIROAN REALTY, LLC

    Unlisted Address
  • /2

    $540,000 Sold Jul 15, 2025

    • 2,167 Sq Ft
    • $249/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1978

    1529 Ensenada Dr, Orlando, FL 32825

    Charming Traditional Pool Home on a lovely 1/3-acre lot in the highly desirable Rio Pinar golf course community!! Classic brick exterior and lush landscaping welcome you to step inside and experience an inviting Open floor plan that blends Spaciousness with comfort! Living area features an amazing, vaulted Wood ceiling, new Luxury Vinyl flooring, and and a warm, wood-burning brick Fireplace in

    Amy Hodges RE/MAX 200 REALTY

    1529 Ensenada Dr, Orlando, FL 32825
    • /10

      Est $187,081 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,046 Sq Ft

      8136 Claire Ann Dr Unit 207, Orlando, FL 32825

      8136 Claire Ann Dr Unit 207, Orlando, FL 32825
  • /34

    $514,900 Pending

    • 3 Beds
    • 2 Baths
    • 2,367 Sq Ft

    9330 Shadow Pinar Ct, Orlando, FL 32825

    Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Step into comfort and convenience with this charming home located in the desirable Villages of Rio Pinar. The home offers FULLY PAID OFF SOLAR PANELS and 2023 ROOF, Situated on a peaceful cul-de-sac, this beautifully maintained property boasts a spacious, open-concept layout perfect for modern living. The

    Abby Nelson RE/MAX 200 REALTY

    9330 Shadow Pinar Ct, Orlando, FL 32825
  • /50

    $1,794 - $2,525 per month

    The Avery

    1-3 Beds

    1000 Avery Village Loop, Orlando, FL 32825

    Immerse yourself in the excitement of Orlando living at The Avery, your luxurious urban oasis. Our community offers a peaceful retreat with all the modern amenities you need, all while being surrounded by Orlando’s stunning landscape and lively cultural scene. Whether you’re exploring world-class dining, entertainment, or the nearby attractions, The Avery is your perfect home base for an

    1000 Avery Village Loop, Orlando, FL 32825
  • /2

    $235,000 Sold Jul 14, 2025

    • 850 Sq Ft
    • $276/SF
    • 42 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1984

    1138 Easton St, Orlando, FL 32825

    Spacious 2 Bedroom / 1 Bath / 2 Car Garage Duplex located in the East Orlando Area. Available Now. Home has new roof and new ac replaced on 04/2021. Tile flooring in the entire home. Fenced back yard with large screened patio porch. All with a Community Pool. Excellent location and super LOW HOA. Pride in home ownership beams here! Walk-in with no worries. This property is on septic. Comfort

    Graham Hardy TRUSTHOME PROPERTIES INC

    1138 Easton St, Orlando, FL 32825
    • /28

      Est $432,311 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,646 Sq Ft

      8525 Fort Thomas Way, Orlando, FL 32822

      8525 Fort Thomas Way, Orlando, FL 32822
  • /24

    $425,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,506 Sq Ft

    1002 Royalton Rd, Orlando, FL 32825

    Under contract-accepting backup offers. Taking back up offers. This beautifully updated 3 bedroom 2 bath home offers modern upgrades, extra space, and the freedom to make it your own in a quiet neighborhood! Enjoy peace of mind with a *brand new roof* and hot water heater! Sellers are currently replacing both and work is scheduled to be completed before closing. Featuring *new flooring, *updated

    Amanda Varmuza CHARLES RUTENBERG REALTY ORLANDO

    1002 Royalton Rd, Orlando, FL 32825
  • /3

    $2,500 per month

    • 4 Beds
    • 1.5 Baths
    • 1,354 Sq Ft
    • House for Rent

    7751 Segovia St, Orlando, FL 32822

    4 bed 1.5 bath Single Family Home with large fenced backyard. Washer and Dryer available. Located in quiet neighborhood near shops and entertainment. Plenty of space to park. Great lot for boat owners or if you need to store tools. Home is in great condition ready to move in. Schedule a showing today.

    Abel Henriquez AMERICAN REALTY EXPERTS

    7751 Segovia St, Orlando, FL 32822
  • /2

    $365,000 Sold Jul 11, 2025

    • 1,064 Sq Ft
    • $343/SF
    • 28 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1971

    1007 Maya Ave, Orlando, FL 32822

    Welcome to this beautifully upgraded 3 bedroom, 2 bathroom pool home offering 1,064 heated square feet of cozy, comfortable living. Perfect as a starter home or investment property, it’s ideally located just 17 minutes from the airport and close to shopping, restaurants, and world-famous theme parks. Inside, you’ll find a modern kitchen with stainless steel appliances, pantry, crown molding

    Christina Laidley LA ROSA REALTY KISSIMMEE

    1007 Maya Ave, Orlando, FL 32822
    • /22

      Est $194,011 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,111 Sq Ft

      952 Courtyard Ln Unit E1, Orlando, FL 32825

      952 Courtyard Ln Unit E1, Orlando, FL 32825
  • /44

    $605,000 Pending

    • 5 Beds
    • 4 Baths
    • 2,663 Sq Ft

    9047 Tuscan Valley Place, Orlando, FL 32825

    Under contract-accepting backup offers. Two-Story Waterfront Home in East Orlando. This spacious floor plan provides 2,663 heated square feet of immaculate living space consisting of 4 bedrooms, 4 bathrooms, a flex room/loft (or 5th bedroom!), living room/dining room combo, remodeled kitchen, breakfast nook, family room with updated electric fireplace, and interior laundry. The optional 5th

    Sheri Malin REDFIN CORPORATION

    9047 Tuscan Valley Place, Orlando, FL 32825
  • /15

    $1,311 - $1,766 per month

    Windrift Apartment Homes

    1-2 Beds

    949 Crowsnest Cir, Orlando, FL 32825

    Welcome home to Windrift Apartment Homes!

    949 Crowsnest Cir, Orlando, FL 32825
  • /2

    $315,000 Sold Jul 11, 2025

    • 1,157 Sq Ft
    • $272/SF
    • 258 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    7685 Ceres Dr, Orlando, FL 32822

    This 3-bedroom home sits directly on the community pond (no rear neighbors!) The cement-block single-story house features a spacious kitchen with a storage pantry, dining nook, and a water view. There’s a large area to BBQ & entertain and a fenced-in yard. The backyard also includes a large storage shed and plenty of space for a fire pit area, garden, and playscape. Lots of bonus storage in the

    Michael Giordano, Jr COLDWELL BANKER RESIDENTIAL RE

    7685 Ceres Dr, Orlando, FL 32822
    • /13

      Est $642,689 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,530 Sq Ft

      9242 Eagles Perch Place, Alafaya, FL 32825

      9242 Eagles Perch Place, Alafaya, FL 32825

Showing Results 1 - 40, Page 1 of 18

Home Trends in Chickasaw, FL

Housing Trends

Median Sale Price
$409,000
Median Single Family Sale Price
$395,000
Median Townhouse Sale Price
$450,000
Median 2 Bedroom Sale Price
$495,000
Median 1 Bedroom Sale Price
$1,315,000
Average Price Per Sq Ft
$320
Number of Homes for Sale
39
Last 12 months Home Sales
138
Months of Supply
3.40
Median List Price
$449,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
1%
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