9144 ISLEWORTH GARDENS DRIVE, WINDERMERE, FL, 34786
Active123 days on marketListed Apr 9, 2026MLS #O6397842
About this home
9144 ISLEWORTH GARDENS DRIVE
Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This impeccably designed residence offers three expansive bedrooms, each with its own beautifully appointed en-suite bathroom, along with two elegant half baths to accommodate guests with ease. From the moment you arrive, the home’s striking Mediterranean-inspired architecture, circular tower entry, and meticulously landscaped grounds set the tone for the sophistication that awaits inside. Step through the grand entrance into interiors defined by soaring ceilings, abundant natural light, and exquisite craftsmanship at every turn. The gourmet kitchen serves as the heart of the home, showcasing custom cabinetry, premium Sub-Zero appliances, an oversized center island, and designer finishes that seamlessly blend form and function—perfect for both intimate family moments and upscale entertaining. Flowing effortlessly into the main living areas, the open-concept layout creates a warm yet refined atmosphere, enhanced by elegant lighting, stone flooring, and thoughtful architectural details throughout. Retreat to the luxurious primary suite, a private sanctuary featuring a spa-inspired bathroom with soaking tub, walk-in shower, dual vanities, and custom finishes that evoke a five-star resort experience. Each additional bedroom offers generous proportions, privacy, ensuring comfort and convenience for family members and guests alike. The inclusion of two half bathrooms further elevates the home’s functionality for entertaining. The outdoor living spaces are equally impressive, offering the perfect backdrop for enjoying Florida’s year-round sunshine. Whether hosting gatherings or savoring quiet evenings, the seamless indoor-outdoor connection enhances the overall living experience. Located within the exclusive Isleworth community—renowned for its world-class golf, privacy, and unparalleled lifestyle, this residence presents a rare opportunity to own a home that embodies elegance, comfort, and timeless design in one of Central Florida’s most sought-after communities while being close to shopping, world class dining and attractions.
Facts & features
The home at a glance
3
Bedrooms
4
Bathrooms
5,004
Sqft
0.26 ac
Lot size
3
Garage
2019
Year built
One
Levels
$859
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.
$29,074 /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
$29,074/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
$859 vs $954
Days on market
123 vs 47 typical
Where $859/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 Gardens Of Isleworth
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Windermere. See the full Windermere guide →
Gardens Of Isleworth — neighborhood snapshot
Population
43
Median age
58
Median income
$151,250
Avg household
2
Households w/ children
5%
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 → $975K
Windermere median sold, yr/yr
96.5%
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 476% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 9144 ISLEWORTH GARDENS DRIVE
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 · Jul ’26$4,350,000
5036 LATROBE DRIVE · same community
5 bd · 4.5 ba · 5,548 sqft · $784/sqft · 175 DOM
Sold · Nov ’25$3,550,000
9310 ISLEWORTH GARDENS DRIVE · same community
3 bd · 4 ba · 4,333 sqft · $819/sqft · 37 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 9144 ISLEWORTH GARDENS DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 9144 ISLEWORTH GARDENS DRIVE — 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
9144 ISLEWORTH GARDENS DRIVE FAQs
What would the monthly payment be for 9144 ISLEWORTH GARDENS DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $29,074/mo — principal and interest, the actual property-tax bill, the $1,146/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 9144 ISLEWORTH GARDENS DRIVE?+
The association fee works out to $1,146 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 9144 ISLEWORTH GARDENS DRIVE?+
The most recent tax bill on record (2025) was $35,432. 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 9144 ISLEWORTH GARDENS DRIVE?+
The listing reports pets: Breed Restrictions, Cats OK, Dogs OK, Number Limit, Size Limit. 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 $4,300,000, this home is listed about 296% above the Windermere median of $1,084,500. The market section on this page shows how the area is trending.
Which schools are assigned to 9144 ISLEWORTH GARDENS 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
$4,300,000 runs 476% above the WINDERMERE 34786 median — but at 5,004 sqft it's also 57% 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 $1,146/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Time on market is leverage
123 days on market against a Windermere median of 47 — 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 MEGAN DOWDY REALTY, LLC · Megan Dowdy. MLS #O6397842.
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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