5127 Leeward Way | Orlando, FL
Where Summer Lingers and Life Slows Down
Tucked away on a peaceful cul-de-sac with LOW HOA, this 4-bedroom, 3-bath pool home offers the kind of lifestyle that feels like a permanent vacation. Whether you’re spending the day on the water, relaxing in the pool, or enjoying quiet evenings in your backyard oasis, this home brings the best of Florida living right to your doorstep.
The main living area features a spacious open layout with a large eat-in kitchen, granite countertops, stainless steel appliances, and plenty of natural light. A generous upstairs bonus room gives you flexibility for a media space, guest suite, or creative zone.
Out back, the private pool and spa are surrounded by tropical landscaping, fruit-bearing gardens, and winding pathways that invite exploration. Follow the garden trails to your covered boat dock with lift — the perfect launching point for endless days on the Conway Chain of Lakes.
There’s room for everyone and everything, with a 3-car garage, extended driveway, and even a climate-controlled “She Shed” complete with chandelier — ideal for an art studio, home office, or quiet hideaway.
According to Orange County tax records, this property is zoned for Pershing K-8 and Boone High School, both known for their wonderful programs.
As summer winds down everywhere else, here it’s still full of sunshine, fresh-picked fruit, and long weekends on the water. If you’re ready to make your move before fall arrives, 5127 Leeward Way is ready to welcome you home.
Where Summer Lingers and Life Slows Down
Tucked away on a peaceful cul-de-sac with LOW HOA, this 4-bedroom, 3-bath pool home offers the kind of lifestyle that feels like a permanent vacation. Whether you’re spending the day on the water, relaxing in the pool, or enjoying quiet evenings in your backyard oasis, this home brings the best of Florida living right to your doorstep.
The main living area features a spacious open layout with a large eat-in kitchen, granite countertops, stainless steel appliances, and plenty of natural light. A generous upstairs bonus room gives you flexibility for a media space, guest suite, or creative zone.
Out back, the private pool and spa are surrounded by tropical landscaping, fruit-bearing gardens, and winding pathways that invite exploration. Follow the garden trails to your covered boat dock with lift — the perfect launching point for endless days on the Conway Chain of Lakes.
There’s room for everyone and everything, with a 3-car garage, extended driveway, and even a climate-controlled “She Shed” complete with chandelier — ideal for an art studio, home office, or quiet hideaway.
According to Orange County tax records, this property is zoned for Pershing K-8 and Boone High School, both known for their wonderful programs.
As summer winds down everywhere else, here it’s still full of sunshine, fresh-picked fruit, and long weekends on the water. If you’re ready to make your move before fall arrives, 5127 Leeward Way is ready to welcome you home.
Property Details
Price:
$1,590,000
MLS #:
O6309938
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
RIVER OAKS
Neighborhood:
32809 – Orlando/Pinecastle/Oakridge/ Edgewood
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 Sep 06, 2025
3,190
Single Family Listed
103
Avg DOM
284
Avg $ / SqFt
$665,051
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 $1,590,000 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 $414. The average price per square foot for Single Family listings in ORLANDO is $284. The average listing price for Single Family in ORLANDO is $665,051. 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 Internet Data Exchange (IDX) Program of Stellar MLS. 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. Stellar MLS. All rights reserved. 5127 LEEWARD WAY
ORLANDO, FL