
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL, 34786
Active27 days on marketListed Aug 26, 2026MLS #O6436860
About this home
9725 CHESTNUT RIDGE DRIVE
A rare opportunity to lease a beautifully renovated residence within Isleworth, offering exceptional space, privacy, comfort, and an elevated Central Florida lifestyle. Newly renovated and exceptionally private, this sophisticated Isleworth residence offers approximately 8,000 square feet of beautifully designed living space, combining refined luxury with the comfort and functionality of an exceptional home. Rich walnut cabinetry and custom wood detailing bring warmth and character throughout, while elegant living spaces, a fireplace, and wine cellar create an inviting setting for both everyday living and entertaining. At the heart of the home, the impressive chef’s kitchen features Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, steam oven, dual dishwashers, and a discreet hidden pantry. Two separate laundry areas add convenience for a residence of this scale. The flexible floor plan includes six bedrooms, a dedicated office, and a bonus room with a closet that may serve as an additional bedroom, guest suite, fitness room, or private retreat. Five full and two half baths are beautifully finished with a calm, contemporary aesthetic, while an elevator provides effortless access between levels. Outdoors, complete privacy and peaceful pond views create a wonderful sense of retreat. A gas-heated pool and spa, expansive outdoor living areas, and summer kitchen provide an ideal setting for relaxing, dining, and entertaining year-round. The residence also features four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors. Some photos have been virtually staged. Private showings are easily accommodated, including same-day requests.
Facts & features
The home at a glance
7
Bedrooms
6
Bathrooms
8,000
Sqft
0.56 ac
Lot size
3
Garage
1999
Year built
Three Or More
Levels
$4
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Principal and interest plus estimated taxes and insurance. Run your own numbers below.
$370 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
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
Estimated payment
$370/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Estimates only — taxes at 1.1%/yr and typical insurance; 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
$4 vs $948
Days on market
27 vs 48 typical
Where $4/sqft sits among the 20 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 20
ISLEWORTH have cut their price
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 96% below the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
Reality check
What actually sold near 9725 CHESTNUT RIDGE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
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
Sold · Oct ’25$2,750,000
5067 LATROBE DRIVE · same community
5 bd · 7 ba · 6,219 sqft · $442/sqft · 123 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
Moe Thouk Oo
Licensed Realtor® · CENTURY 21 Edge
Tours, negotiation, and every question about 9725 CHESTNUT RIDGE DRIVE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 9725 CHESTNUT RIDGE DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Moe's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
9725 CHESTNUT RIDGE DRIVE FAQs
What would the monthly payment be for 9725 CHESTNUT RIDGE DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $370/mo — principal and interest, estimated property taxes 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.
Are pets allowed at 9725 CHESTNUT RIDGE DRIVE?+
The listing reports pets: Yes. 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 $29,000, this home is listed about 97% below the Windermere median of $1,089,500. The market section on this page shows how the area is trending.
Which schools are assigned to 9725 CHESTNUT RIDGE 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
Three things that matter here
01Under the WINDERMERE 34786 market on paper
$29,000 is 96% below the WINDERMERE 34786 median of $680,000, and at $4/sqft it sits under the Windermere average of $448.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Strong 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 DOUGLAS ELLIMAN · Dianna Desboyaux. MLS #O6436860.
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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