Call Now:

Broker IDX Billing System

Broker,REALTOR ®,e-PRO
Broker IDX Sites Inc.
A Winning Team
  1. Home
  2. Property Search
  3. Search results
  4. 9731 Chestnut Ridge Drive, WINDERMERE, FL 34786
Contact Broker IDX Sites Inc.
Contacting Broker IDX Sites Inc.
  • 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
Active
Property Photos
9731 Chestnut Ridge Drive
  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
Image Gallery

PRICED AT ONLY: $3,400,000

Address: 9731 Chestnut Ridge Drive, WINDERMERE, FL 34786

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.

Property Location and Similar Properties

All
Similar
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-
  •   Monthly -
For a Fast & FREE Mortgage Pre-ApprovalApply Now
More Like This
  • MLS#: O6336655 ( Residential )
  • Street Address: 9731 Chestnut Ridge Drive
  • Viewed: 134
  • 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: 169

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.
Request More Information
  • All fields are required.
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: 3129.00
  • 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: 134
  • Zoning Code: P-D
Nearby Subdivisions
Aladar On Lake Butler   Ashlin Fark Ph 2   Ashlin Park Ph 1   Bellaria   Belmere Village   Belmere Village G2 48 65   Casa Del Lago Rep   Chaine De Lac   Creeks Run   Davis Shores   Down Point Sub   Enclave   Enclave At Berkshire Park   Farms   Glenmuir   Glenmuir 48 39   Glenmuir Ut 02 51 42   Gotha Town   Harbor Isle   Isleworth   Isleworth West   Keenes Pointe   Keenes Pointe 46104   Keenes Pointe Ut 06 50 95   Kelso On Lake Butler   Lake Burden South Ph I   Lake Butler Estates   Lake Cawood Estates   Lake Crescent Reserve   Lake Down Estates   Lake Down Reserve   Lake Roper Pointe   Lake Sawyer South Ph 01   Lakes   Lakes Windermere Ph 01 49 108   Lakeswindermere Ph 02a   Lakeswindermere Ph 04   Lakeswindermerepeachtree   Metcalf Park Rep   N/a   Palms At Windermere   Peachtree Park   Preston Square   Providence Ph 02   Reserve At Belmere Ph 02   Reserve At Belmere Ph 02 48 14   Reserve At Belmere Phase Iv   Reserve At Lake Butler Sound   Roberts Landing   Sanctuarylkswindermere   Sawyer Sound   Silver Woods Ph 03   Stillwater Xings Prcl Sc13 2   Summerport   Summerport Ph 03   Summerport Ph 05   Tildens Grove   Tildens Grove Ph 01 4765   Tuscany Ridge 50 141   Vineyardshorizons West Ph 1a   Vineyardshorizons West Ph 1b   Waterford Pointe   Waterstone   Wauseon Ridge   Weatherstone On Lake Olivia   West Point Commons   Westover Reserve Ph 02   Westside Village   Whitney Islesbelmere Ph 02   Willows At Lake Rhea Ph 02   Windemere Sound Ph 2   Windermere   Windermere Isle   Windermere Landings   Windermere Lndgs Fd1   Windermere Lndgs Ph 02   Windermere Pointe   Windermere Rep   Windermere Sound   Windermere Sound Ph 2   Windermere Terrace   Windermere Town   Windermere Town Rep   Windermere Trls Ph 1b   Windermere Trls Ph 1c   Windermere Trls Ph 3b   Windermere Trls Ph 5a   Windsor Hill   Windstone  
Similar Properties

Active
Details for 13643 Lake Cawood Drive, WINDERMERE, FL 34786
$3,590,000.00 ($334.55 / sqft )

13643 Lake Cawood Drive Virtual Tour More Like This

Luxury HOME 8 Bedroom (all Suite) with One acre lot in exclusive Lake Cawood Estates in Windermere. Built from ICF insulated concrete blocks for superior energy efficiency and hurricane protection w

  1. Request Information
  1. Bedrooms: 8
  2. Baths: 8
  3. Approx. 10731 sqft
  4. Approx. 1.00 acres
  1. MLSID: O6285301
  2. Provided by JWJ REALTY LLC
  3. Contact Wenwen Wang
  4. mfrmls
  5. DMCA Notice
74 Pictures and Information
Active
Details for 13305 Bellaria Circle, WINDERMERE, FL 34786
$3,490,000.00 ($386.23 / sqft )

13305 Bellaria Circle More Like This

In the gated Bellaria community, featuring six expansive bedrooms, including two primary suites and four en suites, this residence is an ideal blend of privacy and convenience with a beautiful lake vi

  1. Request Information
  1. Bedrooms: 6
  2. Baths: 8
  3. Approx. 9036 sqft
  1. MLSID: O6286539
  2. Provided by PREMIER SOTHEBYS INT'L REALTY
  3. Contact Alex Minato
  4. mfrmls
  5. DMCA Notice
75 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 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 5024 Sawyer Cove Way, WINDERMERE, FL 34786
$3,600,000.00 ($439.94 / sqft )

5024 Sawyer Cove Way Virtual Tour More Like This

Welcome to The Sounding: a captivating lakefront estate residence with inviting water views and a serene and peaceful setting offering the best of Florida living. Tucked inside this privately gated an

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 7
  3. Approx. 8183 sqft
  1. MLSID: O6348086
  2. Provided by STOCKWORTH REALTY GROUP
  3. Contact Rob Rahter
  4. mfrmls
  5. DMCA Notice
75 Pictures and Information
Active
Details for 4301 Down Point Lane, WINDERMERE, FL 34786
$3,325,000.00 ($331.14 / sqft )

4301 Down Point Lane Virtual Tour More Like This

One or more photo(s) has been virtually staged. EXPERIENCE LUXURY LAKEFRONT LIVING in this rare Mediterranean style estate on 3.5 private acres in WindermereHOA FREE! This stunning 5 bedroom, 4 bath h

  1. Request Information
  1. Bedrooms: 5
  2. Baths: 4
  3. Approx. 10041 sqft
  4. Approx. 3.47 acres
  1. MLSID: O6351950
  2. Provided by MARK SPAIN REAL ESTATE
  3. Contact ARod Rodriguez-Aponte
  4. mfrmls
  5. DMCA Notice
55 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 10870 Bayshore Drive, WINDERMERE, FL 34786
$3,300,000.00 ($525.31 / sqft )

10870 Bayshore Drive Virtual Tour More Like This

Set against the shimmering waters of Little Lake Down, this extraordinary lakefront home offers an elevated expression of luxury living. Thoughtfully designed to maximize sweeping water views, the r

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 5
  3. Approx. 6282 sqft
  1. MLSID: O6371471
  2. Provided by ONE LUXURY INTERNATIONAL LLC
  3. Contact Julie Christensen
  4. mfrmls
  5. DMCA Notice
60 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

Contact Info

Skip to Main Content
  1. Broker IDX Sites Inc.
  2. A Winning Team
Broker IDX Billing System

Looking To Sell Your Property ?

Connecting agents, buyers, and sellers
Call Us Now Get In Touch
Featured Listings
84 Lincoln Avenue
4747 Nw 35th Lane Road
717 Ocean Shore Boulevard
4766 Atlantic Avenue
6436 Grand Cypress Circle
36 Allenwood Look

Copyright ©2006-2026 brokerIDXsites.com   |   All Rights Reserved.