$1,590,000
$60K PRICE DROP

Estimated payment $9,388/month

Total Views 11,782
4 Beds
3 Baths
3,836 Sq Ft
$414 Price per Sq Ft

Highlights

  • Dock has access to electricity
  • Parking available for a boat
  • Access To Lake
  • Boone High School Rated A
  • Boat Lift
  • Screened Pool

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.

Listing Agent

Natalie Rosario

FATHOM REALTY FL LLC Brokerage Phone: 888-455-6040 License #679586 Listed on: 05/17/2025

FATHOM REALTY FL LLC

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $8,717

Year Built

  • Built in 1972

Lot Details

  • 0.61 Acre Lot
  • Property fronts a freshwater canal
  • West Facing Home
  • Irrigation Equipment
  • Property is zoned R-1AA

HOA Fees

  • $15 Monthly HOA Fees

Parking

  • 3 Car Garage
  • Parking Pad
  • Workshop in Garage
  • Rear-Facing Garage
  • Garage Door Opener
  • On-Street Parking
  • Parking available for a boat

Property Views

  • Chain Of Lake
  • Canal

Home Design

  • Block Foundation
  • Shingle Roof
  • Block Exterior

Interior Spaces

  • 3,836 Sq Ft Home
  • Tray Ceiling
  • Shutters
  • Sliding Doors
  • Family Room
  • Combination Dining and Living Room
  • Game Room
  • Sun or Florida Room

Kitchen

  • Eat-In Kitchen
  • Built-In Convection Oven
  • Cooktop
  • Microwave
  • Ice Maker
  • Dishwasher
  • Stone Countertops
  • Disposal

Flooring

  • Wood
  • Ceramic Tile

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Primary Bedroom on Main
  • Split Bedroom Floorplan
  • 3 Full Bathrooms

Laundry

  • Laundry Room
  • Dryer
  • Washer

Accessible Home Design

  • Visitor Bathroom

Pool

  • Screened Pool
  • In Ground Pool
  • In Ground Spa
  • Gunite Pool
  • Saltwater Pool
  • Fence Around Pool
  • Pool Sweep

Outdoor Features

  • Access To Lake
  • Access To Chain Of Lakes
  • Access to Freshwater Canal
  • Water Skiing Allowed
  • Boat Lift
  • Covered Boat Lift
  • Dock has access to electricity
  • Covered Dock
  • Dock made with wood
  • Outdoor Kitchen
  • Exterior Lighting
  • Outdoor Grill
  • Private Mailbox

Schools

  • Pershing Elementary School
  • Boone High School

Utilities

  • Central Heating and Cooling System
  • Tankless Water Heater
  • Septic Tank
  • Cable TV Available

Listing and Financial Details

Community Details

Overview

  • River Oaks HOA
  • River Oaks Subdivision

Recreation

  • Community Basketball Court

Home Details

Home Type

Single Family

Est. Annual Taxes

$8,717

Year Built

Built in 1972

Lot Details

0

HOA Fees

$15 per month

Parking

3

Listing Details

  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Construction Materials: Block
  • Fireplace: No
  • Living Area: 3836
  • Lot Size Acres: 0.61
  • New Construction: No
  • Year Built: 1972
  • Accessibility Features: Visitor Bathroom
  • Building Area Total: 4941
  • Lot Size Sq Ft: 26636
  • Directions to Property: Orange Ave south to harbour island east to leeward north
  • Status: Active
  • Ownership: Fee Simple
  • Available for Lease YN: 0
  • Escrow State: FL
  • List Office Head Office Key Nume: 172132292
  • RATIO Current Price By Calculate: 414.49
  • Total Acreage: 1/2 to less than 1
  • Unit Number YN: 0
  • Water Access YN: 1
  • MFR_InLawSuiteYN: 0
  • MFR_DockDescription: Dock - Covered,Dock - Wood,Dock w/Electric
  • MFR_DockYN: 1
  • Attribution Contact: 888-455-6040
  • Tax Year: 2024
  • Special Features: VirtualTour

Interior Features

  • Living Area Units: Square Feet
  • Flooring: Ceramic Tile, Wood
  • Full Bathrooms: 3
  • Interior Amenities: Eat-in Kitchen, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Tray Ceiling(s), Window Treatments
  • Appliances Included: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer
  • Foundation Details: Block
  • Total Bedrooms: 4
  • Levels: One
  • Other Equipment: Irrigation Equipment
  • Spa Features: In Ground
  • Spa Yn: Yes
  • Window Features: Shutters, Window Treatments
  • Street Number Modifier: 5127
  • Living Area Meters: 356.38
  • Room Count: 10

Exterior Features

  • Direction Faces: West
  • Pool Features: Gunite, In Ground, Pool Sweep, Salt Water, Screen Enclosure
  • Exterior Features: Lighting, Outdoor Grill, Outdoor Kitchen, Private Mailbox, Sliding Doors
  • Roof: Shingle
  • Pool Private: Yes
  • Water Body Name: CONWAY CHAIN OF LAKES
  • Waterfront: Yes
  • Road Surface Type: Asphalt
  • Water Access: Canal - Freshwater,Lake,Lake - Chain of Lakes
  • Water Extras: Lift,Lift - Covered,Skiing Allowed
  • Water Extras YN: 1
  • Water View: Canal,Lake - Chain of Lakes
  • Water View YN: 1
  • Waterfront Feet Total: 0
  • Flood Zone Date: 2009-09-25
  • Flood Zone Panel: 12095C0430F
  • Additional Water Information: Beautiful waterfront property nestled between Lake Gatlin and Lil Lake Conway with access to the entire Conway chain of lakes

Garage/Parking

  • Attached Garage: No
  • Carport Y N: No
  • Garage Spaces: 3
  • Garage Yn: Yes
  • Parking Features: Boat, Garage Door Opener, Garage Faces Rear, Guest, On Street, Oversized, Parking Pad, Workshop in Garage

Utilities

  • Utilities: Cable Available, Public
  • Cooling: Central Air
  • Heating: Central
  • Laundry Features: Laundry Room
  • Sewer: Septic Tank
  • Water Source: Canal/Lake For Irrigation, Public

Condo/Co-op/Association

  • Community Features: Street Lights
  • Association Amenities: Basketball Court
  • Association Fee: 175
  • Association Fee Frequency: Annually
  • Association Name: River oaks HOA
  • Association: Yes
  • Senior Community: No
  • Association 2 YN: 0
  • Association Fee Requirement: Required

Fee Information

  • Total Annual Fees: 175.00
  • Total Monthly Fees: 14.58
  • Monthly HOA Amount: 14.58

Schools

  • Elementary School: Pershing Elem
  • High School: Boone High

Lot Info

  • Zoning: R-1AA
  • Parcel Number: 13-23-29-7456-00-430
  • Additional Parcels: No
  • Flood Zone Code: X
  • Homestead YN: 1
  • Lot Size Square Meters: 2475

Green Features

  • Green Verification Count: 0

Rental Info

  • Pets Allowed: No

Tax Info

  • Tax Annual Amount: 8717
  • Tax Block: 00
  • Tax Book Number: 1-147
  • Tax Lot: 43

Multi Family

  • Waterfront Features: Canal - Freshwater, Canal Front

Map

Range of Values:

Collateral Analytics

Collateral Analytics Collateral Analytics AVMs (Automated Valuation Model) employ a number of statistical approaches combined with neighborhood-specific comparable selection guarantees the most up-to-date and precise valuations.

Not Available

Collateral Analytics does not have data for the current month. Please view the chart for historical values.

ICE

ICE Mortgage Technology ICE Mortgage Technology’s AVM (Automated Valuation Model) is a state-of-the-art online residential property valuation tool that provides a quick and accurate estimate of the value of almost any home in the U.S.

Not Available

ICE Mortgage Technology does not have data for the current month. Please view the chart for historical values.

First American

First American First American Data & Analytics’ next-generation AVM combines unrivaled data assets with a blended ensemble of valuation models to produce highly accurate, reliable valuations you can trust.

Not Available

First American does not have data for the current month. Please view the chart for historical values.

Quantarium

Quantarium Quantarium’s valuation service, repeatedly proven the industry’s most accurate and comprehensive, is supercharged with a self-learning and auto-tuning AI engine that continually becomes smarter and more accurate as it processes daily inputs from the industry’s leading RE data lake.

Not Available

Quantarium does not have data for the current month. Please view the chart for historical values.

Average Value
Not Available
List Price
Sold Price
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $8,717 $541,810 -- --
2024 $8,428 $541,810 -- --
2023 $8,428 $511,204 $0 $0
2022 $8,107 $496,315 $0 $0
2021 $7,987 $481,859 $0 $0
2020 $7,612 $475,206 $0 $0
2019 $7,849 $464,033 $0 $0
2018 $7,661 $455,381 $0 $0
2017 $7,573 $683,234 $245,000 $438,234
2016 $7,556 $626,488 $235,000 $391,488
2015 $7,672 $565,842 $200,000 $365,842
2014 $7,622 $492,581 $200,000 $292,581
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
06/19/2025 06/19/25 Price Changed $1,590,000 -3.6% $414 / Sq Ft
05/17/2025 05/17/25 For Sale $1,650,000 -- $430 / Sq Ft
Source: Stellar MLS

Purchase History

Date Type Sale Price Title Company
Warranty Deed -- None Listed On Document
Warranty Deed $41,500 Attorney
Warranty Deed $310,000 Metro Title
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $285,000 New Conventional
Previous Owner $252,000 Credit Line Revolving
Previous Owner $254,900 Unknown
Previous Owner $75,750 Credit Line Revolving
Previous Owner $248,000 Purchase Money Mortgage
Source: Public Records

Similar Homes in Orlando, FL

  • 500 Linson Ct, Orlando, FL 32809

    $1,495,000

    • 4 Beds
    • 4 Baths
    • 3,175 Sq Ft
    • 500 Linson Ct
    • Orlando, FL

    Welcome to 500 Linson Ct. - Where Life Happens BeautifullyWhen you desire more than just a house, you want to live within a piece of architectural artistry. This exceptional home was designed by the renowned architectural firm of Nils M. Schweizer, Frank Lloyd Wright's on-site supervising architect for the construction of Florida Southern College in Lakeland, as well as numerous churches and

    Adam Judd METROPOLIS R.E. SOLUTIONS, LLC

    Section Image
  • 1518 Cloverlawn Ave, Orlando, FL 32806

    $1,169,000

    • 5 Beds
    • 4.5 Baths
    • 3,749 Sq Ft
    • 1518 Cloverlawn Ave
    • Orlando, FL

    Welcome to 1518 Cloverlawn Avenue — a stunning, newly reimagined modern day home nestled in the vibrant Hourglass District of Orlando. This 5-bedroom, 4.5-bathroom property offers nearly 3,750 square feet of beautifully designed living space, including an attached 1-bedroom, 1-bathroom guest house/ADU, perfect for rental income, a home office, or extended family.The main home features a

    Paul Jimenez URBANISTA BROKERS

    Section Image
  • 1521 Harwood St, Orlando, FL 32803

    $1,299,999

    • 5 Beds
    • 4.5 Baths
    • 3,230 Sq Ft
    • 1521 Harwood St
    • Orlando, FL

    Eclectic Elegance in Eola Heights Nestled in the heart of the charming and historic Eola Heights neighborhood of Orlando, this brand-new Colonial-style residence is a perfect fit among the tree-lined streets and timeless architecture that define the area. At first glance, the classic exterior — complete with a symmetrical facade, shuttered windows, and a broad front porch—blends

    David Gilmore PREFERRED REAL ESTATE BROKERS II

    Section Image
  • 5224 Vistamere Ct, Orlando, FL 32819

    $1,250,000

    • 5 Beds
    • 3.5 Baths
    • 3,615 Sq Ft
    • 5224 Vistamere Ct
    • Orlando, FL

    WOW! A Custom Home That Truly Impresses – In the Heart of Dr. Phillips Step into style and comfort in this stunning 5-bedroom, 3.5-bathroom custom home, tucked away in the quiet and exclusive Vistamere community. With the interior painted and tile flooring throughout the entire home, this property offers a fresh, modern feel with timeless details. From the curb, you'll notice the tile roof,

    Farid Premjee REALTY HUB

    Section Image
  • 8612 Summerville Place, Orlando, FL 32819

    $1,375,000

    • 6 Beds
    • 5 Baths
    • 3,925 Sq Ft
    • 8612 Summerville Place
    • Orlando, FL

    Under contract-accepting backup offers. Welcome to an exquisite six-bedroom five bath showcase home featuring a separate mother-in-law suite with private entrance nestled on a beautifully landscape half-acre lot in Orlando. The impressive residence remodeled in 2019 offers exceptional curb appeal, and a thoughtful layout design for comfort and entertainment. The lush, professionally landscaped

    Max Cawal PREMIER SOTHEBYS INT'L REALTY

    Section Image
  • 10819 Savona Way, Orlando, FL 32827

    $1,549,000

    • 5 Beds
    • 5.5 Baths
    • 5,437 Sq Ft
    • 10819 Savona Way
    • Orlando, FL

    Located in the prestigious Lake Nona community of Orlando, this exceptional residence showcases the desirable Sunchase floor plan, offering thoughtfully designed living spaces and elegant finishes throughout. Enhanced by stunning landscaping, this home exudes curb appeal from the moment you arrive. A private, gated courtyard welcomes you to the front entry and sets the tone for the refined

    Valentino Sanchez EXP REALTY LLC

    Section Image
  • 8059 Leaf Grove Cir, Orlando, FL 32836

    $1,250,000

    • 4 Beds
    • 4 Baths
    • 4,205 Sq Ft
    • 8059 Leaf Grove Cir
    • Orlando, FL

    Reduced Price!! $15,000 towards Closing Costs!! This Jewel is nested in the heart of one of the newest community of Dr Phillips, one of Orlando’s upper-class communities with A+ rated Schools and minutes from shopping and restaurants. This lovely home offers over 3,000 sq/ft of living space, boast an open floor plan with vaulted ceilings, formal dining room. A fully equipped Kitchen has plenty

    Liz Morales FUSION FLORIDA REALTY LLC

    Section Image
  • 14025 Hench Ln, Orlando, FL 32827

    $1,435,000

    • 5 Beds
    • 4.5 Baths
    • 3,802 Sq Ft
    • 14025 Hench Ln
    • Orlando, FL

    Seller will consider buyer closing cost/incentives with acceptable offer! This home is a MUST See! This Reef model built by David Weekley offers a highly desired floor plan for the main house and a detached garage apartment. Situated on a Mew in Laureate Park, this home has a serene front view. Upon entry, you will adore the front wrap around side porch. As you enter the home you will appreciate

    Crystal Grohowski CORCORAN PREMIER REALTY

    Section Image
  • 5526 Parkdale Dr, Orlando, FL 32839

    $1,599,999

    • 5 Beds
    • 5 Baths
    • 4,389 Sq Ft
    • 5526 Parkdale Dr
    • Orlando, FL

    Priced below appraised value, this stunningly reimagined lakefront residence on Lake Jessamine offers anunmatched blend of craftsmanship, comfort, and character. With over 140 feet of shimmering shoreline anda private dock, the setting is nothing short of exceptional, offering uninterrupted sunrises and apeaceful, natural backdrop for daily living. Step inside to a bright and fluid

    Parker Blanchard OLDE TOWN BROKERS INC

    Section Image

Source: Stellar MLS

MLS Number: O6309938

Stellar MLS

APN: 13-2329-7456-00-430