5127 Leeward Way, ORLANDO, FL 32809
Local realty services provided by:Better Homes and Gardens Real Estate Thomas Group



Listed by:natalie rosario
Office:fathom realty fl llc.
MLS#:O6309938
Source:MFRMLS
Price summary
- Price:$1,590,000
- Price per sq. ft.:$321.8
- Monthly HOA dues:$14.58
About this home
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.
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Home facts
- Year built:1972
- Listing Id #:O6309938
- Added:89 day(s) ago
- Updated:August 14, 2025 at 12:18 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:3
- Full bathrooms:3
- Living area:3,836 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central
Structure and exterior
- Roof:Shingle
- Year built:1972
- Building area:3,836 sq. ft.
- Lot area:0.61 Acres
Schools
- High school:Boone High
- Elementary school:Pershing Elem
Utilities
- Water:Public
- Sewer:Public, Septic Tank
Finances and disclosures
- Price:$1,590,000
- Price per sq. ft.:$321.8
- Tax amount:$8,717 (2024)
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