9743 Chestnut Ridge Dr, Windermere, FL 34786
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Home Description
Nestled at the end of a quiet cul-de-sac on 1.15 acres within the renowned Isleworth Golf & Country Club, this exceptional residence offers refined luxury, thoughtful design, and exceptional grounds designed for outdoor enjoyment all year round. Featuring five bedrooms, six full bathrooms, and a powder room, the home spans more than 6,300 square feet, with lovely architectural style and beautifully appointed interiors. The stunning great room is a true centerpiece, featuring soaring cathedral ceilings, exposed wood beams, and abundant natural light. Formal living and dining rooms provide ideal spaces for entertaining, while the chef’s kitchen boasts granite countertops, white cabinetry, and high-end Bosch and Sub-Zero appliances. The primary suite is a serene retreat, featuring a luxurious en-suite bath and direct access to the pergola and pool for seamless indoor-outdoor living. Upstairs, a versatile bonus room offers flexible space for a yoga studio, home gym, game room or creative retreat, complemented by a stylish loft office perfect for work-from-home needs. Step outside to discover the expansive backyard complete with modern pool is surrounded by low-maintenance artificial turf, expansive lanai spaces for alfresco dining, and multiple seating areas ideal for gatherings or quiet relaxation—all framed by a vast, fenced yard. This extraordinary home offers both comfort and sophistication in a community renowned for its golf, amenities, and lifestyle. A rare opportunity to live luxuriously in a premier setting.
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
- Private Pool: True
- Pool Features: In Ground
- Water Name: LAKE BUTLER CHAIN OF LAKES
- Water Feet: 0
- Water Access: Lake - Chain of Lakes
- Interior Features: Built-in Features,Ceiling Fans(s),High Ceilings,Primary Bedroom Main Floor,Vaulted Ceiling(s),Walk-In Closet(s),Wet Bar
- Appliances: Bar Fridge,Built-In Oven,Dishwasher,Disposal,Dryer,Freezer,Microwave,Refrigerator,Washer,Wine Refrigerator
- Fireplace Desc: Family Room,Primary Bedroom
- Floor Covering: Tile,Wood
- Exterior Features: Awning(s),Lighting
- Exterior Contruction: Concrete
- Foundation: Slab
- Front Exposure: South
- Roof: Tile
- Building Sqft: 7162
Approximate Room Sizes / Descriptions
| Bathroom 1 | | First | |
| Kitchen | | First | |
| Great Room | | First | |
| Living Room | | First | |
| Gym | | Second | |
| Primary Bedroom | | First | |
| Bedroom 2 | | First | |
| Bedroom 3 | | First | |
| Bedroom 4 | | First | |
- Attached Garage: True
- Garage: True
- Garage Spaces: 4
- Garage Feature: Garage Faces Side
- Carport: False
- Carport Spaces: 0
- Air Conditioning: Central Air
- Heating: Central,Electric
- Utilities: BB/HS Internet Available,Cable Connected,Electricity Connected,Natural Gas Connected
- Lot Sqft: 49984.00
- Lot Acres: 1.1500
- Total Acre: 1 to less than 2
- Lot Num: 8
- HOA Fees: $3,129 Quarterly
- HOA Monthly Amount: $1,043
- HOA/Community Assoc: Required
- Senior Community: False
- Style: Single Family Residence
- Location: Landscaped,Oversized Lot
- Pets Allowed: Breed Restrictions
- Pet Restrictions: Per Orange County Breed restrictions, number limits and leash laws.
- : 407-909-9000
Neighborhood
The average asking price of a 5 bedroom Windermere home in this zip code is
$2,513,087 (22.7% less than this home).
This home is priced at $514/sqft,
which is 5.7% less than similar homes
in the 34786 zip code.
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Financial
- Approx Payment:$15,810*
- Taxes:$22,676
Area Stats
These statistics are updated daily from the My Florida Regional MLS. For further analysis or
to obtain statistics not shown below please call EasyStreet Realty at
(407) 967-1435 and speak with one of our real estate consultants.
Popular Homes
$501,008
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141
1.4%
58.2%
88
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589
0.8%
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85
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$689,000
19
5.3%
52.6%
58
$416,931
$405,000
104
1.9%
52.9%
68
$1,281,168
$1,020,000
54
0.0%
51.9%
97
$674,972
$675,000
18
0.0%
38.9%
289
$947,329
$824,500
24
0.0%
37.5%
42
$581,004
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731
0.5%
56.1%
78
$879,545
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11
0.0%
36.4%
60
$475,437
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287
1.0%
60.6%
84
$433,052
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80
0.0%
32.5%
95
$516,036
$440,000
2398
1.9%
52.3%
108
$738,581
$549,000
211
0.9%
54.5%
76
$984,210
$627,450
104
1.9%
59.6%
82
$560,223
$539,495
158
0.0%
46.2%
77
$1,482,852
$1,095,942
49
0.0%
57.1%
124
$527,604
$483,490
174
1.1%
48.3%
75
$677,963
$499,375
3168
1.8%
51.9%
80
$698,202
$599,000
250
0.8%
50.8%
70
$322,621
$310,490
283
1.8%
51.9%
127
$1,753,503
$1,050,000
113
2.7%
48.7%
145
$751,051
$535,000
27
0.0%
55.6%
323
$519,166
$419,990
407
1.2%
52.8%
88
$609,718
$450,920
109
0.9%
45.0%
91
$862,877
$716,195
619
0.5%
52.0%
87
$1,264,423
$775,000
337
0.6%
56.1%
89
$618,059
$489,900
149
0.7%
47.0%
70
Listing Courtesy of ISLEWORTH REALTY LLC.
9743 Chestnut Ridge Dr, Windermere FL is a single family home of 6328 sqft and
is currently priced at $3,250,000
.
This single family home has 5 bedrooms.
A comparable home for sale at 729 Main Street in Windermere is listed at $2,100,000.
In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos, New Homes and Foreclosures
in Windermere, FL.
Chaine Du Lac, Lake Cawood Estates and Reserve At Lake Butler Sound are nearby neighborhoods.
MLS O6314871 has been posted on this site since 6/4/2025 (today).
2025
6/27/2025.