5001 LATROBE DRIVE, WINDERMERE, FL, 34786
Active128 days on marketListed Mar 17, 2026MLS #O6389183
About this home
5001 LATROBE DRIVE
One or more photo(s) has been virtually staged. Traditional five-bedroom four and a half bath pool home with an open layout in Isleworth Golf & Country Club. Perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lake Bessie. Offering 4,417 square feet of refined living space, this elegant two-story residence features two primary suites downstairs with private en-suites and large walk-in closets, and three bedrooms upstairs, with one of the upstairs bedrooms having a private ensuite. This home underwent a $400,000 update in 2019. Looking for an open layout with the kitchen overlooking the family room? Look no further! Updated ivory cabinetry, a Viking gas range with a French hood, double islands, and three ovens are ideal for daily meal prep and for hosting get-togethers with friends and family. There is ample seating, perfect for accommodating family and guests, with a formal dining room that flows into a family room with panoramic views overlooking the 6th tee. The family room shares a double-sided fireplace with the living room, which is open to the kitchen and has French doors to the covered, screened-in patio. Enjoy the Florida lifestyle with a large covered travertine patio, summer kitchen, heated pool, and an open-air travertine courtyard overlooking Lake Bessie at sunset. A three-car garage and expansive paver driveway provide ample parking. This is an ideal first home in Isleworth or as a vacation home. This is the perfect size and layout for real, everyday livable luxury in Isleworth. All offers will be considered. Schedule your private showing today.
Facts & features
The home at a glance
5
Bedrooms
4.5
Bathrooms
4,417
Sqft
0.61 ac
Lot size
3
Garage
1990
Year built
Two
Levels
$747
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.
$22,785 /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
$22,785/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.
vs edgeAI estimate
+111.4%
$/sqft vs ISLEWORTH
$747 vs $868
Days on market
128 vs 32 typical
Where $747/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)
6 of 14
ISLEWORTH have cut their price
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 304% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 5001 LATROBE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Nov ’25$3,550,000
9310 ISLEWORTH GARDENS DRIVE · same community
3 bd · 4 ba · 4,333 sqft · $819/sqft · 37 DOM
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 · 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
Eric Chery
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 5001 LATROBE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5001 LATROBE DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Eric's phone and CRM.
Straight answers
5001 LATROBE DRIVE FAQs
What would the monthly payment be for 5001 LATROBE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $22,785/mo — principal and interest, the actual property-tax bill, the $1,043/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 5001 LATROBE DRIVE?+
The association fee works out to $1,043 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 5001 LATROBE DRIVE?+
The most recent tax bill on record (2024) was $30,452. 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 5001 LATROBE DRIVE?+
The listing reports pets: Cats OK, Dogs OK. 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 $3,299,999, this home is listed about 200% 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 5001 LATROBE DRIVE?+
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
$3,299,999 runs 304% above the WINDERMERE 34786 median — but at 4,417 sqft it's also 38% 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 $1,043/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Time on market is leverage
128 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 Q BOUTIQUE SPECIALTY REALTY INC · Laura Diss. MLS #O6389183.
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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