5199 Latrobe Dr, photo 1
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Overview

6 bd7 ba4,665 sqft4 car garageSingle Family
TypeSingle Family
HOA$3,672/qtr
Built1993
Lot22,749 sqft
Living area4,665 sqft
Price / sqft$1,136
Garage4 car

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About this home

Primary Bedroom Main FloorStone CountersWalk-in Closet(s)French DoorsRain GuttersBuyer Approval RequiredCommunity MailboxGated Community - Guard

5199 Latrobe Dr is a 1993-built home in Isleworth, Windermere. Inside you'll find 6 bedrooms, 7 bathrooms, and 4,665 square feet of living space. Listed at $5,300,000 (about $1,136/sqft), 143 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $3,672 quarterly.

From the listing

Virtually Staged. 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.

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The essentials

Built
1993
Price / sqft
$1,136
On market
143 days
Annual tax
$37,241
HOA
$3,672/qtr
Flood zone
X · Low risk
Lot
22,749 sqft
Type
Single Family Residence

At a glance

Single family
Built 1993
Water views
Golf Course
Private pool
Heated
4 car garage
Driveway
0.52 acres
Lot size

Payment

Est. monthly payment
$34,619/mo
Down payment (20%)
$1,060,000
Property taxes
$3,103/mo
HOA
$3,672/qtr
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1993
Lot
22,749 sqft
Cooling
Central Air, Zoned
Heating
Central, Electric, Zoned
Parking
Driveway, Garage
Pool
Deck, Gunite, Heated, In Ground, Lighting, Screen Enclosure
Days on Market
143
Primary Bedroom Main Floor
Stone Counters
Walk-in Closet(s)
French Doors
Rain Gutters
Buyer Approval Required
Community Mailbox
Gated Community - Guard
Golf Carts OK
Golf
Park
Street Lights
Built-in Oven
Dishwasher
Disposal
Exhaust Fan
Microwave
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)
$37,241
Parcel #
16-23-28-3899-03-150

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
22,749 sqft
LandscapedOn Golf CoursePaved
HOA
$3,672/qtr
Dan O’Connell

Price history

Date
Event
Price
5/25/2026
Listed for sale
Source: Stellar MLS #O6409961
$5,300,000
$1,136/sqft

Neighborhood

5199 Latrobe Dr
Windermere, FL, 34786 · 34786 - Windermere

Market insights

Offer Insights

Choose an offer strength

List price: $5,300,000
$5.22M – $5.30M
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 143.

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

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Calculator

Est. monthly payment
$34,619/mo
Principal & interest$27,642
Property taxes$3,103
Insurance$2,650
HOA$1,224
Down payment20% · $1,060,000
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

$5,300,000

$1,136 per sq ft

Beds and baths

6 beds, 7 baths

Size

4,665 sq ft

Time on market

143 days

Year built

1993

Monthly payment

About $34,619/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $37,241 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# O6409961.

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