# 9731 CHESTNUT RIDGE DRIVE, Windermere, FL 34786

> **TL;DR:** 4bd/4ba single family, $3,400,000 ($697/sqft), built 1986, 4,877 sqft.
> Pool. Est. $14,733/mo. Listed 306 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $3,400,000 |
| Price/sqft | $697 |
| Bedrooms | 4 |
| Bathrooms | 4 full |
| Square Feet | 4,877 |
| Year Built | 1986 |
| Lot Size | 23,522 sqft (0.54 acres) |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 306 |

## Why This Home Stands Out

- **Pool** - Private pool

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $14,733 |
| **Total** | **$14,733** |

## Nearby Schools

- **Elementary:** Windermere Elem
- **Middle:** Chain of Lakes Middle
- **High:** Olympia High

## Key Amenities

- Pool

## Property Highlights

- Built in 1986
- 0.54 acre lot
- Private pool

## Description

### Agent Description
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style.  The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living.  Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets.  Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function.  The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun.  Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.

## Location

- **Address:** 9731 CHESTNUT RIDGE DRIVE, Windermere, FL 34786
- **County:** Orange
- **Neighborhood:** ISLEWORTH
- **Coordinates:** 28.492813, -81.522664
- **Google Maps:** https://www.google.com/maps?q=28.492813,-81.522664

## Listing Agent

- **Name:** Monica Lochmandy
- **Brokerage:** ISLEWORTH REALTY LLC
- **Phone:** 4072306888
- **Email:** mlochmandy@isleworth.com

## Primary Photo

![9731 CHESTNUT RIDGE DRIVE - Primary Photo](http://lh.rdcpix.com/1ce75b3244d86509f65045eea77f0d44l-f3511329782r.jpg)

*57 total photos available on [listing page](https://www.propertysimple.com/listing/9731-chestnut-ridge-drive-windermere-fl-34786-o6336655)*

---

**MLS#:** O6336655 | **Updated:** 2026-06-17
**Source:** listhub

*Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.com/listing/9731-chestnut-ridge-drive-windermere-fl-34786-o6336655)

---

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