PerformAction
(407) 203-9595
Sign In / Sign Up
 logo  logo
  • What’s My Home Worth
  • Property Search
  • Communities
  • Agents
  • Join Us
  • FRANCHISE WITH US
    • What’s My Home Worth
    • Property Search
    • Communities
    • Agents
    • Join Us
    • FRANCHISE WITH US
Sign In / Sign Up
(407) 203-9595
  • What’s My Home Worth
  • Property Search
  • Communities
  • Agents
  • Join Us
  • FRANCHISE WITH US
    • What’s My Home Worth
    • Property Search
    • Communities
    • Agents
    • Join Us
    • FRANCHISE WITH US
  • Property Info
  • Photo Slideshow
  • Photos
  • Print
  • Save Listing
  • Share Listing
  • Property Info
  • Photos
  • Photo Slideshow
  • Print

9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

 (Sold on )

$5,975,000

  • Open House
  • New Listing
  • Price Reduced$25,000
  • Active
-1 More Schedule
Source MLS Verified
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
1/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
2/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
3/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
4/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
5/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
6/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
7/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
8/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
9/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
10/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
11/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
12/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
13/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
14/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
15/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
16/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
17/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
18/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
19/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
20/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
21/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
22/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
23/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
24/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
25/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
26/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
27/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
28/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
29/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
30/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
31/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
32/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
33/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
34/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
35/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
36/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
37/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
38/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
39/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
40/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
41/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
42/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
43/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
44/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
45/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
46/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
47/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
48/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
49/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
50/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
51/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
52/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
53/54
9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786
54/54
  • 7 BedroomBeds
  • 7 BathroomBaths
  • 8,000Sqft
  • 0Acres
  • Single FamilyType
  • O6370294MLS#
-1 More Schedule

Property Description

Virtually Staged. 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. Some photos have been virtually staged. Private showings are easily accommodated, including same-day requests.

Property Videos And Tours

  • Virtual Tour

Additional Virtual Tour

  • Virtual Tour

Thank you for requesting a showing of this property. A representative will be in touch with you shortly to confirm the requested showing date and time.
Please note that your appointment is not confirmed until someone contacts you.

Request Info/ Schedule Showing

Submit

Property Details 9725 CHESTNUT RIDGE DRIVE, WINDERMERE, FL 34786

Facts & Features

  • MLS #: O6370294
  • Status: Active
  • Date Listed: 01/02/2026
  • Type: Single Family
  • Sub Type: Single Family Residence
  • Year Built: 1999
  • Price: $5,975,000
  • Acres: 0.56
  • Area: 34786 - Windermere
  • County: Orange
  • Subdivision: ISLEWORTH
  • Bedrooms: 7
  • Bathrooms: 7
  • Full Baths: 5
  • Half Baths: 2
  • Total SqFt: 8,000

Amenities

  • Amenities: Clubhouse, Elevators, Fitness Center, Gated, Golf Course, Maintenance, Park, Pickleball Court(s), Playground, Pool, Racquetball, Recreation Facilities, Sauna, Security, Spa/Hot Tub, Storage, Tennis Court(s)
  • Parking: Driveway, Garage Faces Side
  • # of Garages: 3
  • Features: Buyer Approval Required, Clubhouse, Fitness Center, Gated Community - Guard, Golf Carts OK, Golf, No Truck/RV/Motorcycle Parking, Playground, Pool, Racquetball, Restaurant, Tennis Court(s)
  • Waterfront: Yes
  • Waterfront Type: Public
  • Pool: Yes
  • Pool Type: Heated, In Ground, Indoor, Lap, Outside Bath Access, Screen Enclosure, Tile

Interior

  • Interior Features: Built-in Features, Ceiling Fans(s), Elevator, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Wet Bar
  • Flooring: Tile, Travertine, Wood
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer
  • Utilities: Electricity Connected, Water Connected
  • Heating: Central
  • Cooling: Central Air, Zoned
  • # of Stories: 2.00

Exterior

  • Exterior Features: Fire Pit, Outdoor Kitchen
  • Lot Description: Landscaped, Near Golf Course, Paved
  • Roof: Tile
  • Construction: Block, Stucco

Schools

  • Elementary: Windermere Elem
  • Middle: Chain of Lakes Middle
  • High: Olympia High

Additional Information

  • Zoning: P-D

Output format
 

Estimated Monthly Mortgage Calculator

This calculator is provided for informational purposes only by Burrow Services, Inc. You should not make any decisions based simply on the information provided. Values indicated are estimates and may not be accurate and are only to be used as a guide. This calculator should not be relied upon in any way as the sole source of information. Please consult your financial, tax or legal advisers for an accurate assessment of your mortgage payments and any advice relating to your personal circumstances.

Similar Listings

    • New Listing
    • Price Reduced
    • Open House
    • Sold
    • Leased
    • Pending
    • Coming Soon
    • Rental
    9343 TIBET POINTE CIRCLE
    WINDERMERE FL 34786
    $7,450,000
    7 Bed 7 Beds 10 Bath 10 Baths Sq.ft. 8,362
    MLS# O6443379 Single Family
    Listing Courtesy of: NOVA REAL ESTATE SERVICES INC | 407-592-1744
    Listing By:NOVA REAL ESTATE SERVICES INC
    Request Info
    Delete
      • New Listing
      • Price Reduced$345,000
      • Open House
      • Sold
      • Leased
      • Pending
      • Coming Soon
      • Rental
      5074 ISLEWORTH COUNTRY CLUB DRIVE
      WINDERMERE FL 34786
      $7,250,000
      5 Bed 5 Beds 7 Bath 7 Baths Sq.ft. 7,099
      MLS# O6373191 Single Family
      Listing Courtesy of: MEM REALTY GROUP | 407-/58-3702
      Listing By:MEM REALTY GROUP
      Request Info
      Delete
        • New Listing
        • Price Reduced
        • Open House
        • Sold
        • Leased
        • Pending
        • Coming Soon
        • Rental
        5373 ISLEWORTH COUNTRY CLUB DRIVE
        WINDERMERE FL 34786
        $7,200,000
        5 Bed 5 Beds 6 Bath 6 Baths Sq.ft. 5,993
        MLS# O6439156 Single Family
        Listing Courtesy of: STOCKWORTH REALTY GROUP | 407-909-5900
        Listing By:STOCKWORTH REALTY GROUP
        Request Info
        Delete
          • New Listing
          • Price Reduced$405,000
          • Open House
          • Sold
          • Leased
          • Pending
          • Coming Soon
          • Rental
          9349 TIBET POINTE CIRCLE
          WINDERMERE FL 34786
          $6,995,000
          5 Bed 5 Beds 8 Bath 8 Baths Sq.ft. 7,529
          MLS# O6404415 Single Family
          Listing Courtesy of: CORCORAN PREMIER REALTY | 407-965-1155
          Listing By:CORCORAN PREMIER REALTY
          Request Info
          Delete
            • New Listing
            • Price Reduced
            • Open House
            • Sold
            • Leased
            • Pending
            • Coming Soon
            • Rental
            6113 GROSVENOR SHORE DRIVE
            WINDERMERE FL 34786
            $6,950,000
            7 Bed 7 Beds 8 Bath 8 Baths Sq.ft. 8,722
            MLS# O6443311 Single Family
            Listing Courtesy of: COLDWELL BANKER REALTY | 407-647-1211
            Listing By:COLDWELL BANKER REALTY
            Request Info
            Delete
              • New Listing
              • Price Reduced$50,000
              • Open House
              • Sold
              • Leased
              • Pending
              • Coming Soon
              • Rental
              6055 LOUISE COVE DRIVE
              WINDERMERE FL 34786
              $6,850,000
              5 Bed 5 Beds 6 Bath 6 Baths Sq.ft. 7,158
              MLS# O6430931 Single Family
              Listing Courtesy of: STOCKWORTH REALTY GROUP | 407-909-5900
              Listing By:STOCKWORTH REALTY GROUP
              Request Info
              Delete
                • New Listing
                • Price Reduced$100,000
                • Open House
                • Sold
                • Leased
                • Pending
                • Coming Soon
                • Rental
                9061 RON DEN LANE
                WINDERMERE FL 34786
                $6,800,000
                5 Bed 5 Beds 7 Bath 7 Baths Sq.ft. 6,300
                MLS# O6417446 Single Family
                Listing Courtesy of: CORCORAN PREMIER REALTY | 407-965-1155
                Listing By:CORCORAN PREMIER REALTY
                Request Info
                Delete
                  • New Listing
                  • Price Reduced$249,999
                  • Open House
                  • Sold
                  • Leased
                  • Pending
                  • Coming Soon
                  • Rental
                  9621 WINDY RIDGE ROAD
                  WINDERMERE FL 34786
                  $6,750,000
                  9 Bed 9 Beds 16 Bath 16 Baths Sq.ft. 20,445
                  MLS# O6451612 Single Family
                  Listing Courtesy of: CITARELLI REALTY GROUP LLC | 321-303-4238
                  Listing By:CITARELLI REALTY GROUP LLC
                  Request Info
                  Delete
                    • New Listing
                    • Price Reduced
                    • Open House
                    • Sold
                    • Leased
                    • Pending
                    • Coming Soon
                    • Rental
                    11103 BRIDGE HOUSE ROAD
                    WINDERMERE FL 34786
                    $6,750,000
                    5 Bed 5 Beds 8 Bath 8 Baths Sq.ft. 9,403
                    MLS# O6453159 Single Family
                    Listing Courtesy of: STOCKWORTH REALTY GROUP | 407-909-5900
                    Listing By:STOCKWORTH REALTY GROUP
                    Request Info
                    Delete
                      • New Listing
                      • Price Reduced
                      • Open House
                      • Sold
                      • Leased
                      • Pending
                      • Coming Soon
                      • Rental
                      8342 BOYLA COURT
                      WINDERMERE FL 34786
                      $6,700,000
                      8 Bed 8 Beds 10 Bath 10 Baths Sq.ft. 8,133
                      MLS# O6422852 Single Family
                      Listing Courtesy of: THE SIMON SIMAAN GROUP | 407-558-1396
                      Listing By:THE SIMON SIMAAN GROUP
                      Request Info
                      Delete
                        • New Listing
                        • Price Reduced
                        • Open House
                        • Sold
                        • Leased
                        • Pending
                        • Coming Soon
                        • Rental
                        9921 LAKE LOUISE DRIVE
                        WINDERMERE FL 34786
                        $6,650,000
                        5 Bed 5 Beds 7 Bath 7 Baths Sq.ft. 6,970
                        MLS# O6429164 Single Family
                        Listing Courtesy of: ISLEWORTH REALTY LLC | 407-909-9000
                        Listing By:ISLEWORTH REALTY LLC
                        Request Info
                        Delete
                          • New Listing
                          • Price Reduced$95,001
                          • Open House
                          • Sold
                          • Leased
                          • Pending
                          • Coming Soon
                          • Rental
                          6462 DEACON CIR
                          WINDERMERE FL 34786
                          $6,595,000
                          5 Bed 5 Beds 6 Bath 6 Baths Sq.ft. 7,178
                          MLS# O6407107 Single Family
                          Listing Courtesy of: ISLEWORTH REALTY LLC | 407-909-9000
                          Listing By:ISLEWORTH REALTY LLC
                          Request Info
                          Delete
                           Ironvalley Realtors Logo

                          WE GOTyourBACK.

                          OFFICES

                          • Orlando Office

                          • 7680 Universal Blvd, Suite 300 Orlando FL 32819 Contact: (407) 203-9595

                          SEARCH

                          Residential Commercial Lot & Land Multi-Family
                          ©2026 IVRE Orlando.
                          Contact Blog Privacy Policy Accessibility Fair Housing DMCA Notice Agent Login
                          Iron Valley Real Estate, LLC is a real estate franchise company. Each Iron Valley Real Estate office is Independently Owned and Operated. Iron Valley Real Estate, LLC is an Equal Opportunity Employer and supports the Fair Housing Act.
                          Iron Valley Real Estate is powered by Burrow Services, Inc.
                          • Comparison List   0