Contact Sara Oquendo
Contacting Sara Oquendo
  • All fields are required.
Schedule A Showing
Schedule a Showing.
  • All fields are required.
Check this box to Register with us:
Submit an Offer Now!
Submit an Offer Now!
All fields are required.
Print Flyer
9731 Chestnut Ridge Drive, WINDERMERE, FL 34786
Active
  1. Image 1 of 57 For 9731 Chestnut Ridge Drive
  2. Image 2 of 57 For 9731 Chestnut Ridge Drive
  3. Image 3 of 57 For 9731 Chestnut Ridge Drive
  4. Image 4 of 57 For 9731 Chestnut Ridge Drive
  5. Image 5 of 57 For 9731 Chestnut Ridge Drive
  6. Image 6 of 57 For 9731 Chestnut Ridge Drive
  7. Image 7 of 57 For 9731 Chestnut Ridge Drive
  8. Image 8 of 57 For 9731 Chestnut Ridge Drive
  9. Image 9 of 57 For 9731 Chestnut Ridge Drive
  10. Image 10 of 57 For 9731 Chestnut Ridge Drive
  11. Image 11 of 57 For 9731 Chestnut Ridge Drive
  12. Image 12 of 57 For 9731 Chestnut Ridge Drive
  13. Image 13 of 57 For 9731 Chestnut Ridge Drive
  14. Image 14 of 57 For 9731 Chestnut Ridge Drive
  15. Image 15 of 57 For 9731 Chestnut Ridge Drive
  16. Image 16 of 57 For 9731 Chestnut Ridge Drive
  17. Image 17 of 57 For 9731 Chestnut Ridge Drive
  18. Image 18 of 57 For 9731 Chestnut Ridge Drive
  19. Image 19 of 57 For 9731 Chestnut Ridge Drive
  20. Image 20 of 57 For 9731 Chestnut Ridge Drive
  21. Image 21 of 57 For 9731 Chestnut Ridge Drive
  22. Image 22 of 57 For 9731 Chestnut Ridge Drive
  23. Image 23 of 57 For 9731 Chestnut Ridge Drive
  24. Image 24 of 57 For 9731 Chestnut Ridge Drive
  25. Image 25 of 57 For 9731 Chestnut Ridge Drive
  26. Image 26 of 57 For 9731 Chestnut Ridge Drive
  27. Image 27 of 57 For 9731 Chestnut Ridge Drive
  28. Image 28 of 57 For 9731 Chestnut Ridge Drive
  29. Image 29 of 57 For 9731 Chestnut Ridge Drive
  30. Image 30 of 57 For 9731 Chestnut Ridge Drive
  31. Image 31 of 57 For 9731 Chestnut Ridge Drive
  32. Image 32 of 57 For 9731 Chestnut Ridge Drive
  33. Image 33 of 57 For 9731 Chestnut Ridge Drive
  34. Image 34 of 57 For 9731 Chestnut Ridge Drive
  35. Image 35 of 57 For 9731 Chestnut Ridge Drive
  36. Image 36 of 57 For 9731 Chestnut Ridge Drive
  37. Image 37 of 57 For 9731 Chestnut Ridge Drive
  38. Image 38 of 57 For 9731 Chestnut Ridge Drive
  39. Image 39 of 57 For 9731 Chestnut Ridge Drive
  40. Image 40 of 57 For 9731 Chestnut Ridge Drive
  41. Image 41 of 57 For 9731 Chestnut Ridge Drive
  42. Image 42 of 57 For 9731 Chestnut Ridge Drive
  43. Image 43 of 57 For 9731 Chestnut Ridge Drive
  44. Image 44 of 57 For 9731 Chestnut Ridge Drive
  45. Image 45 of 57 For 9731 Chestnut Ridge Drive
  46. Image 46 of 57 For 9731 Chestnut Ridge Drive
  47. Image 47 of 57 For 9731 Chestnut Ridge Drive
  48. Image 48 of 57 For 9731 Chestnut Ridge Drive
  49. Image 49 of 57 For 9731 Chestnut Ridge Drive
  50. Image 50 of 57 For 9731 Chestnut Ridge Drive
  51. Image 51 of 57 For 9731 Chestnut Ridge Drive
  52. Image 52 of 57 For 9731 Chestnut Ridge Drive
  53. Image 53 of 57 For 9731 Chestnut Ridge Drive
  54. Image 54 of 57 For 9731 Chestnut Ridge Drive
  55. Image 55 of 57 For 9731 Chestnut Ridge Drive
  56. Image 56 of 57 For 9731 Chestnut Ridge Drive
  57. Image 57 of 57 For 9731 Chestnut Ridge Drive
Property Photos
9731 Chestnut Ridge Drive
Image Gallery
Would you like to sell your home before you purchase this one?
Priced at Only: $3,400,000
For more Information Call:
Address: 9731 Chestnut Ridge Drive, WINDERMERE, FL 34786
Property Location and Similar Properties
All
Similar
  1. Image 1 of 57 For 9731 Chestnut Ridge Drive
  2. Image 2 of 57 For 9731 Chestnut Ridge Drive
  3. Image 3 of 57 For 9731 Chestnut Ridge Drive
  4. Image 4 of 57 For 9731 Chestnut Ridge Drive
  5. Image 5 of 57 For 9731 Chestnut Ridge Drive
  6. Image 6 of 57 For 9731 Chestnut Ridge Drive
  7. Image 7 of 57 For 9731 Chestnut Ridge Drive
  8. Image 8 of 57 For 9731 Chestnut Ridge Drive
  9. Image 9 of 57 For 9731 Chestnut Ridge Drive
  10. Image 10 of 57 For 9731 Chestnut Ridge Drive
  11. Image 11 of 57 For 9731 Chestnut Ridge Drive
  12. Image 12 of 57 For 9731 Chestnut Ridge Drive
  13. Image 13 of 57 For 9731 Chestnut Ridge Drive
  14. Image 14 of 57 For 9731 Chestnut Ridge Drive
  15. Image 15 of 57 For 9731 Chestnut Ridge Drive
  16. Image 16 of 57 For 9731 Chestnut Ridge Drive
  17. Image 17 of 57 For 9731 Chestnut Ridge Drive
  18. Image 18 of 57 For 9731 Chestnut Ridge Drive
  19. Image 19 of 57 For 9731 Chestnut Ridge Drive
  20. Image 20 of 57 For 9731 Chestnut Ridge Drive
  21. Image 21 of 57 For 9731 Chestnut Ridge Drive
  22. Image 22 of 57 For 9731 Chestnut Ridge Drive
  23. Image 23 of 57 For 9731 Chestnut Ridge Drive
  24. Image 24 of 57 For 9731 Chestnut Ridge Drive
  25. Image 25 of 57 For 9731 Chestnut Ridge Drive
  26. Image 26 of 57 For 9731 Chestnut Ridge Drive
  27. Image 27 of 57 For 9731 Chestnut Ridge Drive
  28. Image 28 of 57 For 9731 Chestnut Ridge Drive
  29. Image 29 of 57 For 9731 Chestnut Ridge Drive
  30. Image 30 of 57 For 9731 Chestnut Ridge Drive
  31. Image 31 of 57 For 9731 Chestnut Ridge Drive
  32. Image 32 of 57 For 9731 Chestnut Ridge Drive
  33. Image 33 of 57 For 9731 Chestnut Ridge Drive
  34. Image 34 of 57 For 9731 Chestnut Ridge Drive
  35. Image 35 of 57 For 9731 Chestnut Ridge Drive
  36. Image 36 of 57 For 9731 Chestnut Ridge Drive
  37. Image 37 of 57 For 9731 Chestnut Ridge Drive
  38. Image 38 of 57 For 9731 Chestnut Ridge Drive
  39. Image 39 of 57 For 9731 Chestnut Ridge Drive
  40. Image 40 of 57 For 9731 Chestnut Ridge Drive
  41. Image 41 of 57 For 9731 Chestnut Ridge Drive
  42. Image 42 of 57 For 9731 Chestnut Ridge Drive
  43. Image 43 of 57 For 9731 Chestnut Ridge Drive
  44. Image 44 of 57 For 9731 Chestnut Ridge Drive
  45. Image 45 of 57 For 9731 Chestnut Ridge Drive
  46. Image 46 of 57 For 9731 Chestnut Ridge Drive
  47. Image 47 of 57 For 9731 Chestnut Ridge Drive
  48. Image 48 of 57 For 9731 Chestnut Ridge Drive
  49. Image 49 of 57 For 9731 Chestnut Ridge Drive
  50. Image 50 of 57 For 9731 Chestnut Ridge Drive
  51. Image 51 of 57 For 9731 Chestnut Ridge Drive
  52. Image 52 of 57 For 9731 Chestnut Ridge Drive
  53. Image 53 of 57 For 9731 Chestnut Ridge Drive
  54. Image 54 of 57 For 9731 Chestnut Ridge Drive
  55. Image 55 of 57 For 9731 Chestnut Ridge Drive
  56. Image 56 of 57 For 9731 Chestnut Ridge Drive
  57. Image 57 of 57 For 9731 Chestnut Ridge Drive
Request More Information
  • All fields are required.
Virtual Tour
More Like This
  • MLS#: O6336655 ( Residential )
  • Street Address: 9731 Chestnut Ridge Drive
  • Viewed: 156
  • Price: $3,400,000
  • Price sqft: $553
  • Waterfront: No
  • Year Built: 1986
  • Bldg sqft: 6151
  • Bedrooms: 4
  • Total Baths: 4
  • Full Baths: 4
  • Garage / Parking Spaces: 2
  • Days On Market: 245
  • Additional Information
  • Geolocation: 28.4928 / -81.5227
  • County: ORANGE
  • City: WINDERMERE
  • Zipcode: 34786
  • Subdivision: Isleworth
  • Elementary School: Windermere Elem
  • Middle School: Chain of Lakes
  • High School: Olympia
  • Provided by: ISLEWORTH REALTY LLC
  • Contact: Monica Lochmandy
  • 407-909-9000
  • mfrmls
  • DMCA Notice
  • 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 homes 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.
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-
  •   Monthly -
For a Fast & FREE Mortgage Pre-ApprovalApply Now
Features
Building and Construction
  • Covered Spaces: 0.00
  • Exterior Features: Balcony, Outdoor Grill, Rain Gutters
  • Flooring: Marble, Travertine
  • Living Area: 4877.00
  • Roof: Tile
Land Information
  • Lot Features: Landscaped, Near Golf Course, Paved
School Information
  • High School: Olympia High
  • Middle School: Chain of Lakes Middle
  • School Elementary: Windermere Elem
Garage and Parking
  • Garage Spaces: 2.00
  • Open Parking Spaces: 0.00
  • Parking Features: Circular Driveway, Golf Cart Garage
Eco-Communities
  • Pool Features: Heated, In Ground, Lighting, Self Cleaning
  • Water Source: Public
Utilities
  • Carport Spaces: 0.00
  • Cooling: Central Air, Zoned
  • Heating: Central, Electric, Natural Gas
  • Pets Allowed: Breed Restrictions
  • Sewer: Septic Tank
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Water Connected
Amenities
  • Association Amenities: Cable TV, Playground, Security
Finance and Tax Information
  • Home Owners Association Fee Includes: Guard - 24 Hour, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance, Security
  • Home Owners Association Fee: 3672.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
  • Tax Year: 2024
Other Features
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Trash Compactor, Washer, Water Filtration System, Water Purifier, Water Softener
  • Association Name: Dan O'Connell
  • Association Phone: 407-909-2071
  • Country: US
  • Interior Features: Cathedral Ceiling(s), Ceiling Fans(s), Kitchen/Family Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s)
  • Legal Description: ISLEWORTH 16/118 LOT 7
  • Levels: Two
  • Area Major: 34786 - Windermere
  • Occupant Type: Owner
  • Parcel Number: 16-23-28-3899-00-070
  • View: Pool
  • Views: 156
  • Zoning Code: P-D
Similar Properties

Active
Details for 11002 Lake Butler Boulevard, WINDERMERE, FL 34786
$3,999,999.00 ($438.26 / sqft )

11002 Lake Butler Boulevard Virtual Tour More Like This

Price Adjustment! Lakefront Living in the Heart of Windermere A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseon Baypart of the world renowned

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 8
  3. Approx. 9127 sqft
  4. Approx. 1.15 acres
  1. MLSID: O6284922
  2. Provided by SERENDIPITY REALTY LLC
  3. Contact Sean Oakley
  4. mfrmls
  5. DMCA Notice
71 Pictures and Information
Active
Details for 12132 Montalcino Circle, WINDERMERE, FL 34786
$3,950,000.00 ($472.66 / sqft )

12132 Montalcino Circle Virtual Tour More Like This

Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Winderm

  1. Request Information
  1. Bedrooms: 6
  2. Baths: 7
  3. Approx. 8357 sqft
  1. MLSID: O6319854
  2. Provided by BELLA VIEW REALTY LLC
  3. Contact Caroline Perotti
  4. mfrmls
  5. DMCA Notice
91 Pictures and Information
Active
Details for 4819 Alexandra Garden Court, WINDERMERE, FL 34786
$3,200,000.00 ($495.28 / sqft )

4819 Alexandra Garden Court Virtual Tour More Like This

Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this beautiful four bedroom, four bathroom custom villa, whe

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 6461 sqft
  1. MLSID: O6330108
  2. Provided by ISLEWORTH REALTY LLC
  3. Contact Michelle Corbin
  4. mfrmls
  5. DMCA Notice
44 Pictures and Information
Active
Details for 13448 Bellaria Circle, WINDERMERE, FL 34786
$3,200,000.00 ($405.12 / sqft )

13448 Bellaria Circle Virtual Tour More Like This

Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! This exceptional Florida residence is perfectly sited on an acre within the exclusive guard gat

  1. Request Information
  1. Bedrooms: 6
  2. Baths: 7
  3. Approx. 7899 sqft
  1. MLSID: O6346484
  2. Provided by KENNEDY REALTY GROUP LLC
  3. Contact Shawn Kennedy
  4. mfrmls
  5. DMCA Notice
65 Pictures and Information
Active
Details for 6130 Grosvenor Shore Drive, WINDERMERE, FL 34786
$3,500,000.00 ($458.24 / sqft )

6130 Grosvenor Shore Drive Virtual Tour More Like This

Remarkable Waterview Estate in Keenes Pointe! Heated Saltwater Pool, Main Floor Living, and Expansive Outdoor Living Space. Discover an exceptional custom Goehring & Morgan home offering the perfe

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 7638 sqft
  1. MLSID: O6361099
  2. Provided by DOUGLAS ELLIMAN
  3. Contact Dianna Desboyaux
  4. mfrmls
  5. DMCA Notice
47 Pictures and Information
Active
Details for 58 Main Street, WINDERMERE, FL 34786
$3,725,000.00 ($586.15 / sqft )

58 Main Street Virtual Tour More Like This

Nestled in the heart of Old Town Windermere, this exceptional lakefront residence offers direct access to the Butler Chain of Lakes from the tranquil waters of Wauseon Bay, prized for its reduced boat

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 4
  3. Approx. 6355 sqft
  1. MLSID: O6370886
  2. Provided by LPT REALTY, LLC
  3. Contact Michelle Ingrassia
  4. mfrmls
  5. DMCA Notice
52 Pictures and Information
Active
Details for 5538 Lake Butler Road, WINDERMERE, FL 34786
$3,495,000.00 ($399.66 / sqft )

5538 Lake Butler Road Virtual Tour More Like This

Welcome to 5538 W Lake Butler Roadan expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Floridas most coveted locations, Kelso on Lake Butler. What d

  1. Request Information
  1. Bedrooms: 6
  2. Baths: 6
  3. Approx. 8745 sqft
  4. Approx. 1.90 acres
  1. MLSID: O6376859
  2. Provided by STOCKWORTH REALTY GROUP
  3. Contact Julie Bettosini, PA
  4. mfrmls
  5. DMCA Notice
71 Pictures and Information
Active
Details for 10577 Down Lakeview Circle, WINDERMERE, FL 34786
$3,500,000.00 ($474.71 / sqft )

10577 Down Lakeview Circle Virtual Tour More Like This

Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping pano

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 7373 sqft
  4. Approx. 2.97 acres
  1. MLSID: O6377244
  2. Provided by THE SIMON SIMAAN GROUP
  3. Contact Simon Simaan
  4. mfrmls
  5. DMCA Notice
100 Pictures and Information
Active
Details for 9940 Grosvenor Pointe Circle, WINDERMERE, FL 34786
$3,195,000.00 ($393.81 / sqft )

9940 Grosvenor Pointe Circle Virtual Tour More Like This

Welcome to an extraordinary custom residence located within the prestigious guard gated golf community of Keenes Pointe, one of Windermeres most sought after luxury enclaves. Built in 2014 and set

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 7
  3. Approx. 8113 sqft
  1. MLSID: O6380812
  2. Provided by DOUGLAS ELLIMAN
  3. Contact Dianna Desboyaux
  4. mfrmls
  5. DMCA Notice
50 Pictures and Information
Active
Details for 5145 Latrobe Drive, WINDERMERE, FL 34786
$3,449,000.00 ($525.36 / sqft )

5145 Latrobe Drive Virtual Tour More Like This

Welcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar and a dramatic two story living room with a fireplace

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 6565 sqft
  1. MLSID: O6382287
  2. Provided by SOUTHERN REALTY GROUP LLC
  3. Contact Teresa Stewart
  4. mfrmls
  5. DMCA Notice
73 Pictures and Information
Nearby Subdivisions
Balmoral   Bellaria   Belmere Village   Belmere Village G2 48 65   Butler Bay   Casa Del Lago   Casa Del Lago Rep   Casa Del Lagoreplat   Casabella   Chaine Du Lac   Davis Shores   Diamondhead   Down Point Sub   Edens Hammock   Enclave   Enclaveberkshire Park B G H I   Estanciawindermere   Farms   Gardensisleworth   Glenmuir   Glenmuir 48 39   Glenmuir Ut 02 51 42   Gotha   Gotha Town   Harbor Isle   Isles Windermere   Isleworth   Keenes Pointe   Keenes Pointe 46104   Keenes Pointe Ut 04 Sec 29 48    Keenes Pointe Ut 04 Sec 31 48    Kelso On Lake Butler   Lake Burden South Ph I   Lake Butler Estates   Lake Butler Park Pt Rep   Lake Crescent Reserve   Lake Down Estates   Lake Down Pointe 50 42   Lake Olivia Reserve   Lake Roper Pointe   Lake Sawyer South Ph 01   Lake Sawyer South Ph 02   Lake Sawyer South Ph 1   Lakes   Lakes Of Windermere   Lakes Windermere Ph 01 49 108   Lakeswindermere   Lakeswindermere Ph 01 49 108   Lakeswindermere Ph 02a   Lakeswindermere Ph 04   Lakeswindermerepeachtree   Landings At Lake Sawyer   Metcalf Park Rep   Oxford Moor 47/30   Palms At Windermere   Peachtree Park   Preston Square   Providence   Providence Ph 01 50 03   Reserve At Belmere   Reserve At Belmere Phase Iv   Reserve At Lake Butler Sound   Roberts Landing   Sanctuarylkswindermere   Sawyer Shores Sub   Sawyer Sound   Silver Woods   Silver Woods Ph 01   Silver Woods Ph 05   Silver Woods Ph 3   Stillwater Xings Prcl Sc13 Ph   Summerport   Summerport Ph 03   Summerport Ph 05   Summerport Ph 5   Sunset Bay   Tildens Grove   Tildens Grove Ph 01 4765   Tildens Grove Ph 02   Waterford Pointe Ph 02 Rep   Waterstone   Wauseon Ridge   Weatherstone On Lake Olivia   Westover Club Ph 1 Rep   Westside Village   Whitney Islesbelmere Ph 02   Wickham Park   Willows At Lake Rhea Ph 02   Windermere   Windermere Grande   Windermere Isle   Windermere Isle Ph 2   Windermere Landings Ph 2   Windermere Lndgs Fd1   Windermere Lndgs Ph 02   Windermere Pointe   Windermere Sound   Windermere Terrace   Windermere Town   Windermere Town Rep   Windermere Trls Ph 1a   Windermere Trls Ph 1b   Windermere Trls Ph 1c   Windermere Trls Ph 3b   Windermere Trls Ph 4b   Windermere Trls Ph 5b   Windsor Hill   Windstone  
Skip to Main Content
Headshot for Associate Sara Oquendo
  1. Sara Oquendo, REALTOR ®
  2. Tropic Shores Realty
  3. Mobile: 352.428.8657
  4. saraoquendo1972@gmail.com