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Overview

4 bd5 ba4,330 sqft3 car garageSingle Family
TypeSingle Family
HOA$3,672/qtr
Built1994
Lot21,939 sqft
Living area4,330 sqft
Price / sqft$1,155
Garage3 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Built-in FeaturesCeiling Fans(s)Crown MoldingEat-in KitchenKitchen/Family Room ComboLiving Room/Dining Room ComboSolid Surface CountersStone Counters

5138 Fairway Oaks Dr is a 1994-built home in Isleworth, Windermere. Inside you'll find 4 bedrooms, 5 bathrooms, and 4,330 square feet of living space. Listed at $4,999,500 (about $1,155/sqft), 175 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $3,672 quarterly.

From the listing

Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.

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The essentials

Built
1994
Price / sqft
$1,155
On market
175 days
Annual tax
$19,599
HOA
$3,672/qtr
Flood zone
X · Low risk
Lot
21,939 sqft
Type
Single Family Residence

At a glance

Single family
Built 1994
Water views
Golf Course
Private pool
Heated
3 car garage
Circular Driveway
0.50 acres
Lot size

Payment

Est. monthly payment
$31,431/mo
Down payment (20%)
$999,900
Property taxes
$1,633/mo
HOA
$3,672/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1994
Lot
21,939 sqft
Cooling
Central Air, Zoned
Heating
Electric, Natural Gas
Parking
Circular Driveway, Garage Door Opener, Garage Faces Side
Pool
Deck, Heated, In Ground
Days on Market
175
Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Solid Surface Counters
Stone Counters
Thermostat
Walk-in Closet(s)
Lighting
Rain Gutters
Buyer Approval Required
Community Mailbox
Gated Community - Guard
Golf Carts OK
Playground
Street Lights
Bar Fridge
Dishwasher
Disposal
Dryer
Electric Water Heater
Exhaust Fan
Freezer
Ice Maker
Microwave
Range
Range Hood
Refrigerator
Washer
Wine Refrigerator
Elementary
Windermere Elem
Middle
Chain of Lakes Middle
High
Olympia High

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X
Annual Tax (2025)
$19,599
Parcel #
16-23-28-3899-01-080

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Isleworth
County
Orange
MLS Area
34786 - Windermere
Lot Size
21,939 sqft
LandscapedOn Golf CourseOversized Lot
HOA
$3,672/qtr
Dan O’Connell

Price history

Date
Event
Price
8/14/2026
Price change
Source: Stellar MLS #O6401757
$4,999,500-9.1%
$1,155/sqft
4/23/2026
Listed for sale
Source: Stellar MLS #O6401757
$5,500,000
$1,270/sqft

Neighborhood

5138 Fairway Oaks Dr
Windermere, FL, 34786 · 34786 - Windermere

Market insights

Offer Insights

Choose an offer strength

List price: $4,999,500
$4.92M – $5.00M
98.5% – 100% of listTops out right at the list price
80% of listList price
154 of the last 306 home closings in 34786 landed at this number or higher (50%). The median one sat 30 days before it went under contract, and this one is on day 175 after a $500,500 cut.

Sample: 306 closed home sales in 34786 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$31,431/mo
Principal & interest$26,074
Property taxes$1,633
Insurance$2,500
HOA$1,224
Down payment20% · $999,900
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA includes any condo dues reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$4,999,500

$1,155 per sq ft

Beds and baths

4 beds, 5 baths

Size

4,330 sq ft

Time on market

175 days

Year built

1994

Monthly payment

About $31,431/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $19,599 annual tax bill, insurance, and the $3,672/qtr HOA fee.

HOA fee

$3,672/qtr

Managed by Dan O’Connell.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byISLEWORTH REALTY LLCListing agent: Monica LochmandyListing data from Stellar MLS, MLS# O6401757.

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