
5199 LATROBE DR, WINDERMERE, FL, 34786
Active54 days on marketListed May 27, 2026MLS #O6409961
About this home
5199 LATROBE DR
Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined Central Florida living at its finest. Perfectly positioned along Isleworth’s celebrated championship golf course, the residence captures sweeping views of the fourth fairway while offering the privacy, comfort, and sophistication synonymous with the community’s distinguished lifestyle.Thoughtfully renovated and impeccably maintained, the home encompasses more than 6,600 square feet of combined indoor living and covered outdoor space, where contemporary finishes, designer lighting, and warm architectural details create an atmosphere that is both elegant and inviting. Every space has been intentionally curated—from the centrally located gourmet kitchen to the well-appointed utility spaces, resulting in a residence designed for effortless everyday living and elevated entertaining alike.The flexible floor plan offers exceptional versatility to suit a variety of lifestyles, accommodating configurations of up to six bedrooms, or alternatively a combination of bedrooms, office space, fitness room, or additional gathering areas. Six full baths and one half bath are finished with timeless materials and meticulous attention to detail throughout.At the heart of the home, the designer kitchen features sleek white cabinetry, quartz countertops, stainless steel appliances, and seamless connectivity to the expansive family room and casual dining area. Large glass openings invite natural light indoors while providing direct access to the screened lanai and resort-style pool environment beyond.The private primary suite serves as a luxurious retreat, highlighted by porcelain plank flooring, a spa-inspired bath with freestanding soaking tub and walk-in shower, and an oversized custom walk-in closet. Additional guest suites provide comfort and flexibility for family and visitors, while the home’s four-car garage and expansive motor court offer abundant space for automobile enthusiasts and guests alike.Outdoors, the estate transforms into a true private sanctuary. A newly redesigned saltwater pool and spa are enclosed within a custom lanai structure and complemented by an expansive new pool deck, creating a year-round setting for relaxation and entertaining. Lush landscaping, a fenced rear lawn, and panoramic golf course vistas further enhance the sense of serenity and exclusivity.Blending timeless elegance with modern livability, this exceptional Isleworth residence offers a rare combination of spacious design, privacy, and premier golf-front surroundings within one of the finest golf club communities in the world.
Facts & features
The home at a glance
6
Bedrooms
6.5
Bathrooms
4,665
Sqft
0.52 ac
Lot size
4
Garage
1993
Year built
One
Levels
$1,136
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.
$35,073 /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
$35,073/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
$1,136 vs $859
Days on market
54 vs 32 typical
Where $1,136/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
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 555% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 5199 LATROBE DR
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$2,900,000
6186 LOUISE COVE DRIVE · same community
4 bd · 5.5 ba · 4,849 sqft · $598/sqft · 0 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 · Sep ’25$2,500,000
5138 FAIRWAY OAKS DRIVE · same community
4 bd · 4.5 ba · 4,330 sqft · $577/sqft · 159 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 5199 LATROBE DR — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5199 LATROBE 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
5199 LATROBE DR FAQs
What would the monthly payment be for 5199 LATROBE DR?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $35,073/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 5199 LATROBE 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 5199 LATROBE DR?+
The most recent tax bill on record (2025) was $37,241. 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 5199 LATROBE 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 $5,300,000, this home is listed about 382% 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 5199 LATROBE 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
Four things that matter here
01Positioned at the premium end
$5,300,000 runs 555% above the WINDERMERE 34786 median — but at 4,665 sqft it's also 46% 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.
04Strong 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 #O6409961.
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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