5036 LATROBE DRIVE, WINDERMERE, FL, 34786
Active6 days on marketListed Sep 14, 2026MLS #O6441249
About this home
5036 LATROBE DRIVE
Virtually Staged. Pre-Construction. To be built. Poised on a remarkable .69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare opportunity to create a substantial private estate in one of Isleworth’s most coveted lakefront settings. Designed and to be built by Supreme International Construction, the residence will encompass approximately 15,337 square feet of living space across three levels, with six bedrooms, including two private primary suites, an elevator and a four-car garage accommodating up to eight vehicles with lifts. Created for both grand entertaining and effortless everyday living, the main level will feature a dramatic great hall, formal dining room, family room, expansive kitchen, private study and serene primary retreat. Soaring architectural spaces and multiple covered balconies create a natural connection to the lakefront setting. The lower level is envisioned as a private destination for leisure, with a beautifully appointed theater delivering an immersive viewing experience, complemented by a separate popcorn and snack room for added convenience and fun. A generous entertainment area, bar, summer kitchen, gym, yoga/Pilates studio, sauna and spa complete the level. The upper floor offers a second primary suite, additional bedroom suites, viewing lounge and PJ lounge. The outdoor living space is designed to maximize the breathtaking lakefront setting. Landlocked and private, Lake Bessie offers an intimate waterfront experience for boating, water sports and fishing, with no public access to the lake. This rare pre-construction opportunity offers the privilege of securing an extraordinary lakefront residence while personalizing select finishes as the residence takes shape. Within Isleworth’s 600-acre residential community, Isleworth Golf & Country Club, consistently recognized among the world’s finest private clubs, offers an exceptional lifestyle, with Membership offered separately and subject to application and approval.
Facts & features
The home at a glance
6
Bedrooms
8
Bathrooms
15,337
Sqft
0.69 ac
Lot size
4
Garage
2027
Year built
Three Or More
Levels
$1,223
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.
$111,109 /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
$111,109/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
$1,223 vs $948
Days on market
6 vs 48 typical
Where $1,223/sqft sits among the 18 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
$875K → $840K
Windermere median sold, yr/yr
96.5%
Sale-to-list ratio (12 mo)
10 of 18
ISLEWORTH have cut their price
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 2657% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 5036 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 · Oct ’25$9,000,000
9832 LAUREL VALLEY DRIVE · same community
6 bd · 8.5 ba · 11,100 sqft · $811/sqft · 0 DOM
Sold · May ’26$11,500,000
5525 ISLEWORTH COUNTRY CLUB DR · same community
5 bd · 5.5 ba · 9,511 sqft · $1,209/sqft · 333 DOM
Sold · Sep ’25$3,250,000
9743 CHESTNUT RIDGE DRIVE · same community
5 bd · 6.5 ba · 6,328 sqft · $514/sqft · 6 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
Colleen Brown
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 5036 LATROBE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5036 LATROBE DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Colleen's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
5036 LATROBE DRIVE FAQs
What would the monthly payment be for 5036 LATROBE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $111,109/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 5036 LATROBE DRIVE?+
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 5036 LATROBE DRIVE?+
The most recent tax bill on record (2026) was $18,230. 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 5036 LATROBE DRIVE?+
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 $18,750,000, this home is listed about 1621% above the Windermere median of $1,089,500. The market section on this page shows how the area is trending.
Which schools are assigned to 5036 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
$18,750,000 runs 2657% above the WINDERMERE 34786 median — but at 15,337 sqft it's also nearly 5 times the size of the typical Windermere listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
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.
04Fresh on the market
Only 6 days on market in a Windermere market that averages 48 — if it fits, move quickly.
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 #O6441249.
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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