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.
Sold for $1,350,000
$1,350,000
5127 Leeward Way, Orlando, FL 32809
4beds
3,836sqft
Single Family Residence
Built in 1972
0.61 Acres Lot
$1,359,700 Zestimate®
$352/sqft
$4,414 Estimated rent
Home value
$1,359,700
$1.24M - $1.50M
$4,414/mo
Zestimate® history
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List your homeWhat's special
Lakefront livingGranite countertopsFlexible upstairs bonus roomSparkling pool and spaPeaceful cul-de-sacFruit-bearing gardensSpacious eat-in kitchen
Zillow last checked:
Listing updated:
Listing Provided by:
Natalie Rosario 407-468-7465,
FATHOM REALTY FL LLC 888-455-6040
Bought with:
Laura Napoleon, 3056694
KELLER WILLIAMS WINTER PARK
Source: Stellar MLS,MLS#: O6309938
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 418 Square Feet
- Dimensions: 19x22
Bedroom 1
- Features: Built-in Closet
- Level: First
- Area: 110 Square Feet
- Dimensions: 11x10
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 140 Square Feet
- Dimensions: 14x10
Bedroom 3
- Features: Built-in Closet
- Level: First
- Area: 224 Square Feet
- Dimensions: 14x16
Dining room
- Level: First
- Area: 182 Square Feet
- Dimensions: 13x14
Family room
- Level: First
- Area: 432 Square Feet
- Dimensions: 27x16
Florida room
- Level: First
- Area: 462 Square Feet
- Dimensions: 14x33
Game room
- Level: Second
- Area: 792 Square Feet
- Dimensions: 22x36
Kitchen
- Features: No Closet
- Level: First
- Area: 361 Square Feet
- Dimensions: 19x19
Living room
- Level: First
- Area: 182 Square Feet
- Dimensions: 13x14
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer
- Laundry: Laundry Room
Features
- Eating Space In Kitchen, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Tray Ceiling(s)
- Flooring: Ceramic Tile, Hardwood
- Doors: Outdoor Grill, Outdoor Kitchen, Sliding Doors
- Windows: Shutters, Window Treatments
- Has fireplace: No
Interior area
- Total structure area: 4,941
- Total interior livable area: 3,836 sqft
Property
Parking
- Total spaces: 3
- Parking features: Boat, Garage Door Opener, Garage Faces Rear, Guest, On Street, Oversized, Parking Pad, Workshop in Garage
- Garage spaces: 3
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Visitor Bathroom
Features
- Levels: One
- Stories: 1
- Exterior features: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Mailbox
- Has private pool: Yes
- Pool features: Gunite, In Ground, Pool Sweep, Salt Water, Screen Enclosure
- Has spa: Yes
- Spa features: In Ground
- Has view: Yes
- View description: Canal, Lake
- Has water view: Yes
- Water view: Canal,Lake
- Waterfront features: Canal - Freshwater, Canal Front, Freshwater Canal Access, Lake Privileges, Lift, Lift - Covered, Skiing Allowed
- Body of water: CONWAY CHAIN OF LAKES
Lot
- Size: 0.61 Acres
Details
- Parcel number: 132329745600430
- Zoning: R-1AA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block
- Foundation: Block
- Roof: Shingle
Condition
- New construction: No
- Year built: 1972
Utilities & green energy
- Sewer: Septic Tank
- Water: Canal/Lake For Irrigation, Public
- Utilities for property: Cable Available, Public, Street Lights
Community & neighborhood
Location
- Region: Orlando
- Subdivision: RIVER OAKS
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $15 monthly
- Amenities included: Basketball Court
- Association name: River oaks HOA
Other fees
- Pet fee: $0 monthly
Other financial information
- Total actual rent: 0
Other
Other facts
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Road surface type: Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 10/30/2025 | Sold | $1,350,000-6.9%$352/sqft |
Source:  Stellar MLS #O6309938 Report a problem | ||
| 9/30/2025 | Pending sale | $1,450,000$378/sqft |
Source: Stellar MLS #O6309938 Report a problem | ||
| 9/15/2025 | Price change | $1,450,000-8.8%$378/sqft |
Source: Stellar MLS #O6309938 Report a problem | ||
| 6/19/2025 | Price change | $1,590,000-3.6%$414/sqft |
Source: Stellar MLS #O6309938 Report a problem | ||
| 5/17/2025 | Listed for sale | $1,650,000+3875.9%$430/sqft |
Source: Stellar MLS #O6309938 Report a problem | ||
| 8/24/2011 | Sold | $41,500-86.6%$11/sqft |
Source: Public Record Report a problem | ||
| 9/22/2003 | Sold | $310,000$81/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $8,717 +3.4% | $526,540 +3% |
| 2023 | $8,428 +4% | $511,204 +3% |
| 2022 | $8,107 +1.5% | $496,315 +3% |
| 2021 | $7,987 +0.7% | $481,859 +1.4% |
| 2020 | $7,929 +1% | $475,206 +2.4% |
| 2019 | $7,849 +2.5% | $464,033 +1.9% |
| 2018 | $7,661 | $455,381 -33.3% |
| 2017 | $7,661 +1.2% | $683,234 +9.1% |
| 2016 | $7,573 +0.2% | $626,488 +10.7% |
| 2015 | $7,556 -0.9% | $565,842 +14.9% |
| 2014 | $7,622 +2.1% | $492,581 +2.7% |
| 2013 | $7,462 +1.2% | $479,518 +0.1% |
| 2012 | $7,377 +3% | $479,099 +18.4% |
| 2011 | $7,161 +9.1% | $404,770 +1.5% |
| 2010 | $6,562 | $398,898 -26.7% |
| 2009 | -- | $544,469 -23.3% |
| 2008 | $6,791 -4.2% | $709,846 -7% |
| 2007 | $7,092 +62.3% | $763,142 +78.3% |
| 2006 | $4,370 +1.2% | $427,973 +34.3% |
| 2005 | $4,318 +4.4% | $318,669 +35.2% |
| 2004 | $4,138 +23.6% | $235,647 +12% |
| 2003 | $3,348 +2.7% | $210,359 +2.5% |
| 2002 | $3,262 +2% | $205,215 +4.3% |
| 2001 | $3,198 +6.6% | $196,803 +3.4% |
| 2000 | $3,002 | $190,310 |
Find assessor info on the county website
Neighborhood: 32809
Nearby schools
GreatSchools rating
- 7/10Pershing Elementary SchoolGrades: K-8Distance: 1.1 mi
- 6/10William R Boone High SchoolGrades: 9-12Distance: 2.2 mi
Schools provided by the listing agent
- Elementary: Pershing Elem
- High: Boone High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$1,359,700
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,359,700
- Florida
- Orange County
- Edgewood
- 32809
- 5127 Leeward Way
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