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.
Sold for $3,250,000
$3,250,000
9743 Chestnut Ridge Dr, Windermere, FL 34786
5beds
6,328sqft
Single Family Residence
Built in 1987
1.15 Acres Lot
$3,210,800 Zestimate®
$514/sqft
$9,023 Estimated rent
Home value
$3,210,800
$2.92M - $3.50M
$9,023/mo
Zestimate® history
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Zillow last checked: 8 hours ago
Listing updated: September 26, 2025 at 09:43am
Listing Provided by:
Carey Sheffield 407-961-2979,
ISLEWORTH REALTY LLC 407-909-9000,
Michelle Corbin 407-491-2690,
ISLEWORTH REALTY LLC
Bought with:
Rob Rahter, 3129153
STOCKWORTH REALTY GROUP
Source: Stellar MLS,MLS#: O6314871
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 7
- Full bathrooms: 6
- 1/2 bathrooms: 1
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
Bedroom 2
- Features: Built-in Closet
- Level: First
Bedroom 3
- Features: Built-in Closet
- Level: First
Bedroom 4
- Features: Built-in Closet
- Level: First
Bathroom 1
- Features: Built-in Closet
- Level: First
Great room
- Level: First
Gym
- Level: Second
Kitchen
- Level: First
Living room
- Level: First
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Bar Fridge, Oven, Dishwasher, Disposal, Dryer, Freezer, Microwave, Refrigerator, Washer, Wine Refrigerator
- Laundry: Inside, Laundry Room
Features
- Built-in Features, Ceiling Fan(s), High Ceilings, Primary Bedroom Main Floor, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
- Flooring: Tile, Hardwood
- Windows: ENERGY STAR Qualified Windows, Window Treatments
- Has fireplace: Yes
- Fireplace features: Family Room, Master Bedroom
Interior area
- Total structure area: 7,162
- Total interior livable area: 6,328 sqft
Property
Parking
- Total spaces: 4
- Parking features: Garage Faces Side
- Attached garage spaces: 4
Features
- Levels: Two
- Stories: 2
- Exterior features: Awning(s), Irrigation System, Lighting
- Has private pool: Yes
- Pool features: In Ground
- Has view: Yes
- View description: Pool
- Waterfront features: Lake Privileges
- Body of water: LAKE BUTLER CHAIN OF LAKES
Lot
- Size: 1.15 Acres
- Features: Landscaped, Oversized Lot
Details
- Parcel number: 162328389900080
- Zoning: P-D
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Concrete
- Foundation: Slab
- Roof: Tile
Condition
- New construction: No
- Year built: 1987
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected
Community & neighborhood
Location
- Region: Windermere
- Subdivision: ISLEWORTH
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $1,043 monthly
- Association name: Dan O’Connell
- Association phone: 407-909-2071
Other fees
- Pet fee: $0 monthly
Other financial information
- Total actual rent: 0
Other
Other facts
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 9/26/2025 | Sold | $3,250,000$514/sqft |
Source:  Stellar MLS #O6314871 Report a problem | ||
| 6/11/2025 | Pending sale | $3,250,000$514/sqft |
Source: Stellar MLS #O6314871 Report a problem | ||
| 6/4/2025 | Listed for sale | $3,250,000+170.8%$514/sqft |
Source: Stellar MLS #O6314871 Report a problem | ||
| 6/15/2004 | Sold | $1,200,000+42%$190/sqft |
Source: Public Record Report a problem | ||
| 7/18/2001 | Sold | $845,000+47%$134/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $22,676 +7.2% | $1,404,165 +3% |
| 2023 | $21,149 +2.9% | $1,363,267 +3% |
| 2022 | $20,547 +1.2% | $1,323,560 +3% |
Find assessor info on the county website
Neighborhood: 34786
Nearby schools
GreatSchools rating
- 10/10Windermere Elementary SchoolGrades: PK-5Distance: 1.6 mi
- 3/10Chain Of Lakes Middle SchoolGrades: 6-8Distance: 1.2 mi
- 5/10Olympia High SchoolGrades: 9-12Distance: 1.1 mi
Schools provided by the listing agent
- Elementary: Windermere Elem
- Middle: Chain of Lakes Middle
- High: Olympia High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$3,210,800
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$3,210,800
- Florida
- Orange County
- Windermere
- 34786
- 9743 Chestnut Ridge Dr