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$1,350,000
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Property Description
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.
Full Property Details
Full Property Details for 5127 Leeward Way
General
- Sold For: $1,350,000
- HOA FEE: $15/month
- HOA FEE FREQ.: Annually
- Taxes: $8,717 (2024)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6309938
- Added to Site: 279 day(s) ago
Interior
- Number of Rooms: 10
- Interior Features: Eating Space In Kitchen, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Tray Ceiling(s), Window Treatments
- Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer
- Flooring: Ceramic Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Basketball Court
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground, Pool Sweep, Salt Water, Screen Enclosure
- Spa: Yes
- Spa Description: In Ground
Exterior
- Exterior Features: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Mailbox, Sliding Doors
Parking
- Garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Boat, Garage Door Opener, Garage Faces Rear, Guest, On Street, Oversized, Parking Pad, Workshop in Garage
Location
- Area: 32809 - Orlando/Pinecastle/Oakridge/ Edgewood
- County: Orange
- Development Name: 32809 - Orlando/Pinecastle/Oakridge/ Edgewood
- Subdivision: RIVER OAKS
- Driving Directions: Orange Ave south to harbour island east to leeward north
- Direction Faces: West
School Information
- Elementary School: Pershing Elem
- High School: Boone High
Community
- Community Name: 32809 - Orlando/Pinecastle/Oakridge/ Edgewood
- Optional Amenities: Basketball Court
- Association: Yes
- Assoc. Name: River oaks HOA
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Septic Tank
- Water District: CONWAY CHAIN OF LAKES
- Water: Canal/Lake For Irrigation, Public
- Utility Description: Cable TV Available, Public, Street Lights
Structural Information
- Exterior Const.: Block
- Roof: Shingle
- Windows: Shutters, Window Treatments
- Stories/Levels: One
- Square Feet: 3,836
- Sq. Ft. Source: Public Records
- Living Area: 3,836 Sq. Ft.
- Year Built: 1972
Lot Features
- Lot Size (Acres): 0.61
- Lot Size (Sq. Ft.): 26,636
- Lot Size: 26636
- Street/Road Desc.: Asphalt
Water Features
- Water Front: Yes
- Water Access: Yes
- Water Access Desc: Canal - Freshwater, Lake, Lake - Chain of Lakes
- Water Extras: Yes
- Water Front Name: CONWAY CHAIN OF LAKES
- Water Front Desc.: Freshwater Canal, Canal Front
Financial Considerations
- Association Fee: $175
- Assoc Fee Freq.: Annually
- Assoc Fee Desc.: Required
- Tax Amount: $8,717
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: RIVER OAKS 1/147 LOT 43
- Flood Zone Info: X
- APN: 132329745600430
- Property ID: 132329745600430
Listed by Fathom Realty Fl Llc
Sold by Keller Williams Winter Park
Get Pre-Approved Today
Schools
Schools serving 5127 Leeward Way
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Pershing Elementary School 905 Waltham Avenue, Orlando, FL 32809 | K-8 | 0.9 mi |
William R Boone High School 1000 East Kaley Street, Orlando, FL 32806 | 9-12 | 2.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5127 Leeward Way
Date
Details
Price
Change
Source
10/30/2025
Sold
$1,350,000
-6.9%
MLS
9/15/2025
Price Reduced
$1,450,000
-8.81%
MLS
6/19/2025
Price Reduced
$1,590,000
-3.64%
MLS
5/17/2025
Listed
$1,650,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
5127 Leeward Way, Orlando, FL 32809 (MLS# O6309938) is a Single Family property that was sold at $1,350,000 on October 30, 2025. Want to learn more about 5127 Leeward Way? Do you have questions about finding other Single Family real estate for sale in Orlando? You can browse all Orlando real estate or contact a Coldwell Banker agent to request more information.

