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253 Cheshire Way, Naples, FL 34110

$3,999,000
  • 253 Cheshire Way, Naples, FL 34110 Main Photo
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Pending Price Reduced by $496,000 on February 26th, 2026
BEDS4 BATHS4 full 2 partial SQUARE FEET6,026 MLS#225084896
STATUSPending PROPERTY TYPEResidential - Single Family SUBDIVISIONAUDUBON COUNTRY CLUB

Property Description

Your Naples Sanctuary Awaits – Completely Reimagined for 2026 Imagine your perfect Naples winter: morning coffee overlooking championship fairways, afternoons by your resort pool, sunset cocktails as Gulf Coast skies ignite in color. This meticulously transformed Audubon estate delivers it all. No Expense Spared Every surface, every finish thoughtfully updated to todays most discerning standards. Fresh paving, new exterior and interior paint, soaring ceilings, gleaming marble floors, and custom finishes throughout. Expansive pocketing doors erase boundaries between indoor and outdoor living, framing spectacular southern golf course views. Chefs Kitchen & Living Spaces The show-stopping kitchen features custom cabinetry, professional appliances, and dual oversized islands—the natural gathering spot. Floor-to-ceiling windows bathe living and dining areas in natural light while showcasing panoramic views. Owners exclusive retreat area designed for indoor/outdoor meditation & yoga. Master Suite Sanctuary Your private retreat offers a sitting area perfect for morning reflection or remote work. The completely reimagined spa bathroom showcases modern finishes, while his-and-hers facilities ensure personal luxury. Resort-Style Outdoor Living Newly renovated pool with sun shelf and spa. Designer gazebo with full outdoor kitchen and bar. Spectacular golf course backdrop. Lush landscaping ensures privacy while showcasing sweeping views. Every sunset becomes an event. Guest Wing Excellence Dedicated upstairs wing with two elegant suites, private baths, living room with kitchenette, and balcony offering panoramic Gulf Coast views. Audubon Country Club Private, gated community featuring championship 18-hole golf, tennis, pickleball, fitness center, heated lap pool, courtside café, vibrant social events, scenic nature trails, and kayak launch. The Opportunity 4 bedrooms | 6 bathrooms | Southern golf course views | Completely updated | Fresh to market January 2026 After extensive renovations, this estate represents exceptional value in Naples most desirable private golf community. Your winter escape awaits.

253 Cheshire Way | MLS# 225084896

This single family home located at 253 Cheshire Way, Naples, FL 34110 is currently listed for sale with an asking price of $3,999,000. This property was built in 2002 and has 4 bedrooms and 4 full and 2 partial baths with 6026 sq. ft. Cheshire Way is located in the AUDUBON COUNTRY CLUB subdivision. Search AUDUBON COUNTRY CLUB real estate on www.realtymark.net today.

Property Features

Property Type: Residential - Single Family
Cooling: Ceiling Fans, Central Electric
Garage: 3
Garage: Attached
Heating: Central Electric
Lot Size: 0.41 Acres
Roof Type: Tile
Stories: 2.0
Taxes: $22,833
Year Built: 2002

Amenities

Built In Grill
Gazebo
Outdoor Kitchen
Patio
Sprinkler Auto

Feature Descriptions

Additional Rooms: Balcony, Den - Study, Family Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Loft, Screened Lanai/Porch
Amenities: Bocce Court, Cabana, Clubhouse, Community Park, Community Pool, Community Room, Exercise Room, Fishing Pier, Golf Course, Internet Access, Lap Pool, Library, Pickleball, Putting Green, Restaurant, Sidewalk, Streetlight, Tennis Court, Underground Utility
Bedroom/Den: 4 - Den
Bedroom: Master BR Ground, Master BR Sitting Area
Building Design: Single Family
Community Type: Gated, Golf Course, Tennis
Construction: Concrete Block, Wood Frame
Days on Site: 60
Den: Yes
Dining: Eat-in Kitchen, Formal
Equipment: Auto Garage Door, Cooktop - Gas, Dishwasher, Disposal, Double Oven, Dryer, Freezer, Generator, Grill - Gas, Home Automation, Microwave, Range, Refrigerator/Icemaker, Reverse Osmosis, Security System, Smoke Detector, Washer, Wine Cooler
Exterior: Stucco
Flooring: Marble, Wood
Furnished: Unfurnished
GEO Area: NA01 - N/O 111th Ave Bonita Beach
Golf Type: Golf Non Equity
Hoa Type: Mandatory
Interior: Fireplace, Foyer, Laundry Tub, Volume Ceiling, Walk-In Closet, Window Coverings, Zero/Corner Door Sliders
Irrigation: Other
Lot: Golf Course, Oversize
Lot Frontage: 150
Maintenance: Cable, Internet/WiFi Access, Legal/Accounting, Manager, Master Assn. Fee Included, Reserve, Security, Street Lights, Street Maintenance
Management: Professional
Mandatory Club Fee: $10855.00/Annually
Master Bath: 2 Masters, Multiple Shower Heads, Separate Tub And Shower
Master Hoa Fee: $6175.00/Annually
Minimum Lease Days: 60
One Time Mandatory Club Fee: $92500
Parcel #: 22510006750
Parking: Circle Drive
Pets: No Approval Needed
Pool: Below Ground, Custom Upgrades, Heated Gas
Rear Exposure: S
Restrictions: Deeded
Road: Private Road
Security: yes
Sewer: Central
Spa: Yes
Spa: Below Ground, Heated Gas, Pool Integrated, Screened
SQFT Total: 8271
Storm Protection: Impact Resistant Windows, Other, Shutters Electric
Swimming Pool: Yes
Total Recurring Fees: 17030
Transfer Fee: 3700.00
Units in Building: 1
Units in Complex: 1
View: Golf Course
Water: Central
Windows: Impact Resistant, Single Hung

Local Schools

High School: AUBREY ROGERS
Middle School: NORTH NAPLES
Elementary School: NAPLES PARK

Listed By / Shown By

Listed By

Agency Name: Downing Frye Realty Inc.
Agency Phone: 239-261-2244

Shown By

Agency Title: RealtyMark
Agency Phone: 888-260-0040

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Estimated Payment

$ 11,969.17 per month $8,900.04 Principal & Interest $1,902.75 Property Tax $1,166.38 Homeowner's Insurance

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All commissions are negotiable Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/04/2026. The listing information on this page last changed on 03/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 03/04/2026 12:00:06 AM EST) or Stellar MLS (last updated Tue 03/03/2026 11:44:00 PM EST) or GSMLS (last updated Tue 03/03/2026 11:53:52 PM EST) or Emerald Coast MLS (last updated Tue 03/03/2026 11:55:21 PM EST) or Central Panhandle Association of Realtors (last updated Tue 03/03/2026 11:57:16 PM EST) or Beaches MLS (last updated Tue 03/03/2026 11:55:48 PM EST) or Naples MLS (last updated Tue 03/03/2026 11:40:52 PM EST) or Bright MLS (last updated Tue 03/03/2026 11:50:12 PM EST) or OneKey MLS (last updated Tue 03/03/2026 11:53:04 PM EST). Real estate listings held by brokerage firms other than RealtyMark may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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