$6,200,900
- 5 Beds
- 5 Baths
- 5,164 sqft (on 0.65 acres)
9730 Chestnut Ridge Dr, Windermere, FL 34786
Est. Refi. Payment $44,152/mo*
Refinance Your HomeCurrently Off Market - Sold Oct 28, 2016 for $3,500,000
Home Value
Trulia Estimate
$6.2MSince last month
Decreased$8K (-0.1%)Since last year
Increased$422K (+7.5%)Since last sale
Increased$3M (+72.7%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +63% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $6.04M |
| August 2026 | $6.2M |
| July 2026 | $6.05M |
| June 2026 | $6.15M |
| May 2026 | $6M |
| April 2026 | $5.94M |
| March 2026 | $5.89M |
| February 2026 | $5.94M |
| January 2026 | $5.7M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.08 | Single-Family Home | $4,350,000 | 07/15/26 | 6 | 8 | 15,337 | |
0.10 | Single-Family Home | $3,250,000 | 09/26/25 | 5 | 6.5 | 6,328 | |
0.19 | Single-Family Home | $2,750,000 | 10/31/25 | 5 | 7 | 6,219 | |
0.16 | Single-Family Home | $4,500,000 | 03/11/26 | 6 | 7 | 6,816 | |
0.24 | Single-Family Home | $3,100,000 | 09/05/26 | 5 | 7 | 7,940 | |
0.20 | Single-Family Home | $6,000,000 | 05/06/26 | 6 | 5.5 | 6,706 | |
0.26 | Single-Family Home | $2,100,000 | 06/10/26 | 4 | 3.5 | 3,525 | |
0.41 | Single-Family Home | $4,400,000 | 12/30/25 | 6 | 8.5 | 5,721 | |
0.43 | Single-Family Home | $3,900,000 | 08/20/26 | 5 | 6 | 5,695 | |
0.34 | Single-Family Home | $2,175,000 | 06/18/26 | 4 | 4.5 | 4,471 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.02 | $4,284,400 | 5 | 6 | 5,557 | Off Market | |
0.10 | $5,975,000 | 7 | 6 | 8,000 | For Sale | |
0.10 | $3,231,300 | 5 | 6.5 | 6,328 | Off Market | |
0.08 | $18,750,000 | 6 | 8 | 15,337 | For Sale | |
0.16 | $4,500,000 | 6 | 7 | 6,816 | Recently Sold | |
0.17 | $1,295,000 | 3 | 2.5 | 3,021 | Recently Sold | |
0.19 | $2,741,200 | 5 | 7 | 6,219 | Off Market | |
0.20 | $6,000,000 | 6 | 5.5 | 6,706 | Recently Sold | |
0.21 | $2,800,000 | 4 | 5 | 4,706 | For Sale | |
0.24 | $3,100,000 | 5 | 7 | 7,940 | Recently Sold | |
0.26 | $2,100,000 | 4 | 3.5 | 3,525 | Recently Sold | |
0.25 | $3,189,000 | 4 | 4.5 | 3,365 | For Sale |
Local Information
-- mins to
Home Highlights
Single-Family Home
Built in 1995
0.65 acre lot
5,164 sqft
$1,201/sqft
Garage
About this House
Rare Find! NEW 5 bed/5 bath European-inspired transitional home w/ picturesque lake frontage in Isleworth. Stripped down to four walls and a slab, this custom masterpiece was re-built w/ state-of-the-art technology, open floorplan & a contemporary design without sacrificing 'warmth' of a home. Upon entry you are immediately greeted by wall-to-wall unobstructed views over Lake Bessie & openness that has to be seen to appreciate. Modern design includes linear tray & false ceilings, 24" porcelain floors, custom moldings, sleek cabinetry & fixtures, & chic glass-front gas fireplace. Equipped w/ home automation, enjoy the power of complete control of media, changeable LED accent lighting, shades, cameras & many other hidden features from your tablet. The home is centered around the living spaces & lake front views w/ the kitchen, formal rooms and family room all unimpeded by walls. Large kitchen boasts induction & gas stoves, 2 refrigerators, wine cooler, and bar seating. Master suite has a large walk-in closet, multiple wardrobes, a private patio looking over the lake, and a bath with dual sinks, walk-in shower and soaking tub. The outdoor living is superb with covered & uncovered areas that can be separated by electric screens & shades for privacy or opened up for entertaining or taking in views of the lake, golf course, & fireworks. The pit-master will appreciate a full outdoor kitchen with grill, sinks, refrigerators and bar seating, as everyone can enjoy the sandy beach, covered dock and sparkling pool.
9730 Chestnut Ridge Dr, Windermere, FL 34786 is a 5 bedroom, 5 bathroom, 5,164 sqft single-family home built in 1995. It last sold for $3,500,000 on Oct 28, 2016. More recently, it was listed as a rental in December 2013 with an asking price of $6,500 per month. That rental listing was removed on April 8, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $6,200,900.
Home Details for 9730 Chestnut Ridge Dr
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Interior Details BasementTypes of Rooms: Walk In Closet, Dining RoomCeiling Fan |
Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 1Floors: Tile, Carpet |
Appliances & Utilities Cable ReadyDishwasherMicrowaveRefrigerator |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: TileDeckExterior: StuccoPatioPorch |
Pool Pool |
Parking & Garage GarageParking Spaces: 2Parking: Carport, Garage Attached |
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Year Built Year Built: 1995Year Updated: 1995 |
Property Type / Style Property Type: Single Family HomeArchitecture: Other |
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Units in Building: 1 |
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Lot Area: 0.65 acres |
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Community rooms Fitness Center |
Fitness & Sports Tennis Court |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Oct 28, 2016 Source: Stellar MLS #O5439585 | Sold | $3,500,000 |
Sep 8, 2016 Source: Agent Provided | Pending | $3,949,000 |
May 13, 2016 Source: Agent Provided | Listed For Sale | $3,949,000 |
Apr 8, 2014 Source: Agent Provided | ListingRemoved | $6,500 |
Dec 10, 2013 Source: Agent Provided | Listed For Rent | $6,500 |
Apr 26, 2013 Source: Stellar MLS #O5037027 | Sold | $1,150,000 |
Jan 22, 2013 Source: Agent Provided | PriceChange | $1,550,000 Price decreased by 21% |
Mar 30, 2011 Source: Agent Provided | Listed For Sale | $1,950,000 |
Jun 4, 2010 Source: Agent Provided | ListingRemoved | $7,500 |
Jan 7, 2010 Source: Agent Provided | Listed For Sale | $7,500 |
Apr 18, 2007 Source: N/A | Sold | $2,900,000 |
Apr 1, 1999 Source: N/A | Sold | $1,589,900 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2024 | $71,280 | $4,709,129 |
Home facts updated by county records
Market trends in Windermere
Last updated August 2026
Avg. sale price
$856K
$41.5KMoM
Sale-to-List Price
96.8%
0.4%MoM
Price per sq ft
$297
$5MoM
Available listings
274
22MoM
Around this home
What Locals Say about Windermere
At least 271 Trulia users voted on each feature.
93 % Say it's dog friendly
92 % Say there are sidewalks
87 % Say car is needed
87 % Say parking is easy
81 % Say people would walk alone at night
80 % Say it's quiet
80 % Say there's holiday spirit
78 % Say kids play outside
75 % Say streets are well-lit
64 % Say yards are well-kept
60 % Say they plan to stay for at least 5 years
59 % Say it's walkable to grocery stores
56 % Say there's wildlife
55 % Say it's walkable to restaurants
54 % Say neighbors are friendly
40 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Frequently asked questions about 9730 Chestnut Ridge Dr
- What is 9730 Chestnut Ridge Dr estimated to be worth?Trulia's estimated value for 9730 Chestnut Ridge Dr in Windermere, FL is $6,200,900.
- What is the price history for 9730 Chestnut Ridge Dr?9730 Chestnut Ridge Dr in Windermere, FL last sold for $3,500,000 in October 2016.
- Is Windermere a buyer's or seller's market?Windermere is currently a balanced market, based on recent for-sale activity.
- What's the median sale price in Windermere?The median sale price in Windermere is $856K. That is up $41.5K from the prior month.
- Does 9730 Chestnut Ridge Dr have air conditioning?Yes, 9730 Chestnut Ridge Dr in Windermere, FL has air conditioning.
- Does 9730 Chestnut Ridge Dr have a pool?Yes, 9730 Chestnut Ridge Dr in Windermere, FL has a pool.

