5138 FAIRWAY OAKS DR, WINDERMERE, FL, 34786
Active90 days on marketListed Apr 25, 2026MLS #O6401757
About this home
5138 FAIRWAY OAKS DR
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.
Facts & features
The home at a glance
4
Bedrooms
5
Bathrooms
4,330
Sqft
0.5 ac
Lot size
3
Garage
1994
Year built
One
Levels
$1,270
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$34,758 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$34,758/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs ISLEWORTH
$1,270 vs $859
Days on market
90 vs 32 typical
Where $1,270/sqft sits among the 14 homes for sale in ISLEWORTH
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Isleworth
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Windermere. See the full Windermere guide →
Isleworth — neighborhood snapshot
Population
630
Median age
58
Median income
$151,250
Avg household
2
Households w/ children
56%
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Windermere market
$839K → $1.0M
Windermere median sold, yr/yr
96.4%
Sale-to-list ratio (12 mo)
7 of 14
ISLEWORTH have cut their price
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 579% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 5138 FAIRWAY OAKS DR
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$2,500,000
5138 FAIRWAY OAKS DRIVE · same community
4 bd · 4.5 ba · 4,330 sqft · $577/sqft · 159 DOM
Sold · Nov ’25$3,550,000
9310 ISLEWORTH GARDENS DRIVE · same community
3 bd · 4 ba · 4,333 sqft · $819/sqft · 37 DOM
Sold · Feb ’26$2,950,000
4711 JOANNA GARDEN CT · same community
3 bd · 3.5 ba · 4,089 sqft · $721/sqft · 60 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 5138 FAIRWAY OAKS DR — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5138 FAIRWAY OAKS DR — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
5138 FAIRWAY OAKS DR FAQs
What would the monthly payment be for 5138 FAIRWAY OAKS DR?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $34,758/mo — principal and interest, the actual property-tax bill, the $1,224/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 5138 FAIRWAY OAKS DR?+
The association fee works out to $1,224 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 5138 FAIRWAY OAKS DR?+
The most recent tax bill on record (2025) was $19,599. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 5138 FAIRWAY OAKS DR?+
The listing reports pets: Breed Restrictions. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Windermere?+
At $5,500,000, this home is listed about 400% above the Windermere median of $1,099,500. The market section on this page shows how the area is trending.
Which schools are assigned to 5138 FAIRWAY OAKS DR?+
Chain Of Lakes Middle (middle), Olympia High (high), Windermere Elementary (elementary) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$5,500,000 runs 579% above the WINDERMERE 34786 median — but at 4,330 sqft it's also 35% larger than the typical Windermere listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Know the monthly fee
The association fee is $1,224/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Time on market is leverage
90 days on market against a Windermere median of 32 — sellers in this position are usually ready to negotiate.
05Strong assigned schools
Chain Of Lakes Middle, Olympia High, Windermere Elementary — Windermere Elementary rates 5 of 5. Always verify assignments with the district.
Keep looking
Similar homes nearby
Listing courtesy of ISLEWORTH REALTY LLC · Monica Lochmandy. MLS #O6401757.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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