Under contract-accepting backup offers. 5127 Leeward Way | Orlando, FL — A Lakefront Retreat for Every Season
Set at the end of a peaceful cul-de-sac, this 4-bedroom, 3-bath pool home blends lakefront living with cozy fall charm. From golden afternoons on the Conway Chain of Lakes to crisp evenings by the firepit, every day feels like a getaway.
Inside, the spacious eat-in kitchen features granite countertops, stainless steel appliances, and plenty of room for both everyday meals and seasonal gatherings. A flexible upstairs bonus room offers space for a media lounge, guest suite, or creative retreat.
Outdoors, tropical landscaping and fruit-bearing gardens line winding paths that lead to the sparkling pool and spa. At the water’s edge, a covered boat dock with lift invites you to savor sunrise paddleboarding, autumn sunsets, or weekend boating adventures.
Practical design meets personality with a 3-car garage, extended driveway, and a climate-controlled She Shed complete with chandelier — perfect for an office, art studio, or private hideaway.
According to Orange County tax records, the home is zoned for Pershing K-8 and Boone High School, both known for strong academic programs.
Here, summer fun blends seamlessly into fall evenings under starlit skies. 5127 Leeward Way is more than a house — it’s a retreat ready for every season.
Set at the end of a peaceful cul-de-sac, this 4-bedroom, 3-bath pool home blends lakefront living with cozy fall charm. From golden afternoons on the Conway Chain of Lakes to crisp evenings by the firepit, every day feels like a getaway.
Inside, the spacious eat-in kitchen features granite countertops, stainless steel appliances, and plenty of room for both everyday meals and seasonal gatherings. A flexible upstairs bonus room offers space for a media lounge, guest suite, or creative retreat.
Outdoors, tropical landscaping and fruit-bearing gardens line winding paths that lead to the sparkling pool and spa. At the water’s edge, a covered boat dock with lift invites you to savor sunrise paddleboarding, autumn sunsets, or weekend boating adventures.
Practical design meets personality with a 3-car garage, extended driveway, and a climate-controlled She Shed complete with chandelier — perfect for an office, art studio, or private hideaway.
According to Orange County tax records, the home is zoned for Pershing K-8 and Boone High School, both known for strong academic programs.
Here, summer fun blends seamlessly into fall evenings under starlit skies. 5127 Leeward Way is more than a house — it’s a retreat ready for every season.
Property Details
Price:
$1,450,000
MLS #:
O6309938
Status:
Pending
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
RIVER OAKS
Neighborhood:
32809orlandopinecastleoakridgeedgewood
Listed Date:
May 17, 2025
Finished Sq Ft:
3,836
Total Sq Ft:
4,941
Lot Size:
26,636 sqft / 0.61 acres (approx)
Year Built:
1972
See this Listing
Schools
Elementary School:
Pershing Elem
High School:
Boone High
Interior
Appliances
Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Ceramic Tile, Hardwood
Heating
Central
Laundry Features
Laundry Room
Exterior
Association Amenities
Basketball Court
Construction Materials
Block
Exterior Features
Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Mailbox, Sliding Doors
Parking Features
Boat, Garage Door Opener, Garage Faces Rear, Guest, On Street, Oversized, Parking Pad, Workshop in Garage
Roof
Shingle
Financial
HOA Fee
$175
HOA Frequency
Annually
HOA Name
River oaks HOA
Tax Year
2024
Taxes
$8,717
Map
Community
- Address5127 LEEWARD WAY ORLANDO FL
- SubdivisionRIVER OAKS
- CityORLANDO
- CountyOrange
- Zip Code32809
Market Summary
Current real estate data for Single Family in ORLANDO as of Oct 02, 2025
3,099
Single Family Listed
105
Avg DOM
285
Avg $ / SqFt
$657,374
Avg List Price
Property Summary
- Located in the RIVER OAKS subdivision, 5127 LEEWARD WAY ORLANDO FL is a Single Family for sale in ORLANDO, FL, 32809. It is listed for $1,450,000 and features 4 beds, 3 baths, and has approximately 3,836 square feet of living space, and was originally constructed in 1972. The current price per square foot is $378. The average price per square foot for Single Family listings in ORLANDO is $285. The average listing price for Single Family in ORLANDO is $657,374. To schedule a showing of MLS#o6309938 at 5127 LEEWARD WAY in ORLANDO, FL, contact your Stonecrest International Realty agent at 561-707-9933.
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Courtesy of FATHOM REALTY FL 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 Stonecrest International Realty include the name of the listing broker. Neither the listing company nor Stonecrest International Realty 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 2025. Orlando/Tampa – FL. All rights reserved. 5127 LEEWARD WAY
ORLANDO, FL