Under contract-accepting backup offers. Welcome to Chickasaw Oaks, where thoughtful UPDATES, a versatile layout and peaceful POND & WOODED VIEWS come together in one well maintained East Orlando home! Major upgrades have already been completed for you – including NEW family room WINDOWS and SLIDING GLASS DOOR (2025), A/C & DUCT WORK (2024), a REMODELED KITCHEN with new cabinetry, sleek QUARTZ COUNTERTOPS and UPDATED STAINLESS STEEL APPLIANCES, custom sliding BARN DOORS added to the primary suite (2024), an UPDATED PRIMARY BATHROOM (2023), FRESH INTERIOR PAINT (2022), lanai rescreening and rain gutters (2022), EXTERIOR PAINT and paver walkway (2021), LUXURY VINYL PLANK FLOORING throughout the main living areas and primary bedroom (2020), plus a newer ROOF (2019) for added peace of mind. The LOW HOA and prime central location only add to the appeal! 4-bedrooms and 2-baths all on one level welcomes you with a charming front porch and a light-filled interior featuring HIGH CEILINGS, formal living and dining spaces, and an open flow designed for everyday living and entertaining. The REMODLED KITCHEN is truly the heart of the home, showcasing stylish quartz countertops, updated cabinetry, modern appliances and a seamless connection to the family room so everyone stays connected. Sellers especially love the open kitchen, abundant natural light and the peaceful views with NO REAR NEIGHBORS.
The desirable SPLIT BEDROOM layout offers privacy and flexibility, with the PRIMARY SUITE in its own wing with a WALK-IN CLOSET and an updated en-suite bath. Three additional bedrooms and a second full bath are positioned on the opposite side of the home, making this layout ideal for guests, family or a home office setup. Sliding glass doors open to a LARGE SCREENED LANAI overlooking the FENCED BACKYARD, where mature landscaping, WATER VIEWS and wooded scenery create a private outdoor retreat. A playground added in 2023 adds even more enjoyment to the outdoor space. Located in the established Chickasaw Oaks community, this home offers quick access to SR 417, 408, 528 and SR 50, making it easy to reach Downtown Orlando, the Orlando International Airport, Lake Nona, Waterford Lakes, Avalon Park, shopping, dining, parks and major employers. MOVE-IN READY with major updates already done, this East Orlando gem delivers the space, style and location you have been looking for. Call today to schedule your tour and fall in love with Red Bay Drive!
The desirable SPLIT BEDROOM layout offers privacy and flexibility, with the PRIMARY SUITE in its own wing with a WALK-IN CLOSET and an updated en-suite bath. Three additional bedrooms and a second full bath are positioned on the opposite side of the home, making this layout ideal for guests, family or a home office setup. Sliding glass doors open to a LARGE SCREENED LANAI overlooking the FENCED BACKYARD, where mature landscaping, WATER VIEWS and wooded scenery create a private outdoor retreat. A playground added in 2023 adds even more enjoyment to the outdoor space. Located in the established Chickasaw Oaks community, this home offers quick access to SR 417, 408, 528 and SR 50, making it easy to reach Downtown Orlando, the Orlando International Airport, Lake Nona, Waterford Lakes, Avalon Park, shopping, dining, parks and major employers. MOVE-IN READY with major updates already done, this East Orlando gem delivers the space, style and location you have been looking for. Call today to schedule your tour and fall in love with Red Bay Drive!
Property Details
Price:
$435,000
MLS #:
O6404624
Status:
Pending
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
CHICKASAW OAKS PH 05
Neighborhood:
32829orlandochickasaw
Listed Date:
May 15, 2026
Finished Sq Ft:
1,888
Total Sq Ft:
2,357
Lot Size:
7,501 sqft / 0.17 acres (approx)
Year Built:
1988
Primary Bedroom Main Floor32829 – Orlando/chickasaw32829orlandochickasawChickasaw Oaks Ph 05Hidden Oaks ElemOdyssey MiddleColonial HighBuyer To Verify Leasing Restrictions With Hoa And/or City/county8-12 MonthsPets Allowed
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Schools
Elementary School:
Hidden Oaks Elem
Middle School:
Odyssey Middle
High School:
Colonial High
Interior
Appliances
Convection Oven, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Luxury Vinyl, Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
Laundry Features
Laundry Room
Levels
One
Exterior
Attached Garage YN
1
Community Features
Sidewalks
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
Northeast
Exterior Features
Lighting, Rain Gutters, Sidewalk, Sliding Doors
Fencing
Chain Link, Fenced, Wood
Garage Spaces
2
Lot Features
Landscaped, Sidewalk
Open Parking YN
1
Parking Features
Driveway, On Street
Patio And Porch Features
Covered, Enclosed, Patio, Rear Porch, Screened
Roof
Shingle
Security Features
Security System, Smoke Detector(s)
View
Trees/Woods, Water
Window Features
Blinds, Rods
Financial
HOA Fee
$236
HOA Fee Frequency
Annually
HOA Name
Community Management Specialists
HOA Phone
407-359-7202
Tax Year
2025
Taxes
$4,136
Map
Community
- Address4866 RED BAY DRIVE ORLANDO FL
- SubdivisionCHICKASAW OAKS PH 05
- CityORLANDO
- CountyOrange
- Zip Code32829
Market Summary
Current real estate data for Single Family in ORLANDO as of Jun 06, 2026
3,095
Single Family Listed
96
Avg DOM
288
Avg $ / SqFt
$681,373
Avg List Price
Property Summary
- Located in the CHICKASAW OAKS PH 05 subdivision, 4866 RED BAY DRIVE ORLANDO FL is a Single Family for sale in ORLANDO, FL, 32829. It is listed for $435,000 and features 4 beds, 2 baths, and has approximately 1,888 square feet of living space, and was originally constructed in 1988. The current price per square foot is $230. The average price per square foot for Single Family listings in ORLANDO is $288. The average listing price for Single Family in ORLANDO is $681,373. To schedule a showing of MLS#o6404624 at 4866 RED BAY DRIVE in ORLANDO, FL, contact your agent at 407-583-9870.
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Courtesy of WEMERT GROUP REALTY LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than include the name of the listing broker. Neither the listing company nor shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 4866 RED BAY DRIVE
ORLANDO, FL