
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL, 34786
Active202 days on marketListed Jan 2, 2026MLS #O6370294
About this home
9725 CHESTNUT RIDGE DRIVE
Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed. The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.
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
$750
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.
$38,249 /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
$38,249/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.
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
$839K → $1.0M
Windermere median sold, yr/yr
96.4%
Sale-to-list ratio (12 mo)
Median sold price, Windermere, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 634% above the WINDERMERE 34786 median. See the full Windermere market guide →
Paper trail
This home's history
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 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
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
9725 CHESTNUT RIDGE DRIVE FAQs
What would the monthly payment be for 9725 CHESTNUT RIDGE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $38,249/mo — principal and interest, the actual property-tax bill, the $1,043/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 9725 CHESTNUT RIDGE DRIVE?+
The association fee works out to $1,043 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 9725 CHESTNUT RIDGE DRIVE?+
The most recent tax bill on record (2024) was $29,046. 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 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 $6,000,000, this home is listed about 446% 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 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
Five things that matter here
01Positioned at the premium end
$6,000,000 runs 634% above the WINDERMERE 34786 median — but at 8,000 sqft it's also nearly 2 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 $1,043/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
04Time on market is leverage
202 days on market against a Windermere median of 32 — 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.
Listing courtesy of DOUGLAS ELLIMAN · Dianna Desboyaux. MLS #O6370294.
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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