253 Cheshire Way


$3,600,000

Status: Sold

Type: Resale Property

Days on Site: 96

Closed Date: 03/31/2026

Listing ID: 225084896


4 Bed

4 Full Bath

& 2 ½ Bath

6,026 Sq. Ft.

Built: 2002

Furnishings: Unfurnished

Total Annual Recurring Fees

$17,030

Total One Time Fees

$96,350

2024 Total Taxes

$22,833

List Price / Square Foot

$663.62

Community

Subdivision/Building

Audubon Country Club

Ownership

Single Family

Building Style

Two Story, Single Family

Floor Plan

2 Story

Lot/Land

Acres: 0.41

Description

Golf Course, Oversize

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 today’s 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.
Chef’s 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.

Garage

Yes

Car Port

No

Parking Spots

3

Parking Description

Circular Driveway, Attached

Private Pool

Yes

Private Spa

Yes

Community Pool

Yes

Pool Description

Community, Pool/Spa Combo, Below Ground, Custom Upgrades, Gas Heat

Spa Description

Below Ground, Heated Gas, Pool Integrated, Screened

View

Golf Course

Rear Exposure

South

Interior Features

Fireplace, Foyer, Laundry Tub, Volume Ceiling, Walk-In Closet(s), Window Coverings, Zero/Corner Door Sliders

Flooring

Marble, Wood

Kitchen

N/A

Appliances

Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Freezer, Grill – Gas, Microwave, Range, Refrigerator/Icemaker, Reverse Osmosis, Washer, Wine Cooler

Dining

Eat-in Kitchen, Formal

Construction

Concrete Block, Wood Frame, Stucco

Roof

Tile

Cooling

Ceiling Fan(s), Central Electric

Bedroom Details

Master BR Ground, Master BR Sitting Area

Additional Rooms

Balcony, Den – Study, Family Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Loft, Screened Lanai/Porch

Exterior Details

Balcony, Screened Lanai/Porch, Built In Grill, Outdoor Kitchen

Storm Protection

Impact Resistant Windows, Other, Shutters Electric

Accessibility

N/A

Elevator

None

Security

Security System, Smoke Detector(s), Gated Community

Amenities

Bocce Court, Cabana, Clubhouse, Park, Pool, Community Room, Fitness Center, Fishing Pier, Golf Course, Internet Access, Library, Pickleball, Putting Green, Restaurant, Sidewalk, Streetlight, Tennis Court(s), Underground Utility

Golf

Golf Non Equity

Maintenance

Cable, Internet/WiFi Access, Legal/Accounting, Manager, Master Assn. Fee Included, Reserve, Security, Street Lights, Street Maintenance

Waterfront

No

Description

None

Gulf Access

No

Gulf Access Type

N/A

Canal Info.

None

Boat / Dock

None

Pets Allowed?

Yes

Number Allowed

N/A

Weight Limit (lbs.)

N/A

Breed Limits

N/A

Other

N/A

Leasing

Number of Leases Allowed per Year

2

Minimum Days of Each Lease

60

Restrictions

Deeded

Elementary School

NAPLES PARK

Middle School

NORTH NAPLES

High School

AUBREY ROGERS

This property listing is courtesy of Downing Frye Realty Inc.: 239-261-2244. The data relating to real estate for sale displayed on this Website comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc., under License No. SL3295589. Properties listed with brokerage firms other than Premiere Plus Realty, Co. are marked with the “BR House” logo. Detailed information about such properties includes the name of the listing broker. The properties displayed may not be all the properties listed with brokerage firms participating in the M.L.S. of Naples, Inc. BR Program, or contained in the database compilation of the M.L.S. of Naples, Inc. This listing was last modified 03/31/2026 06:00pm.

The source of this real property information is the copyrighted and proprietary database compilation of the M.L.S. of Naples, Inc. Copyright 2023 M.L.S. of Naples, Inc. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.


Destinations, Distances & ETAs

Name Miles ETA
Barefoot Beach Preserve 3.5 mi 9 min
Bonita Beach 3.7 mi 9 min
Delnor-Wiggins Pass State Park 4.1 mi 10 min
Vanderbilt Beach Park 5.2 mi 13 min
Pelican Bay Beach (Private) 7.5 mi 24 min
Lovers Key State Park 8.5 mi 19 min
Clam Pass Park 9 mi 24 min
Via Miramar Beach 11.8 mi 27 min
Lowdermilk Park 12.7 mi 29 min
Naples Municipal Beach and Pier 14.8 mi 36 min
Name Miles ETA
Mercato 6.3 mi 17 min
Galleria Shoppes at Vanderbilt 8 mi 21 min
Coconut Point 8.2 mi 23 min
Waterside Shops 8.6 mi 19 min
Venetian Village 10.7 mi 24 min
Coastland Mall 11.7 mi 28 min
5th Avenue South 13.5 mi 30 min
Miromar Outlets 14.5 mi 29 min
Third Street South 14.7 mi 35 min
Gulf Coast Town Center 18.6 mi 33 min
Name Miles ETA
Artis-Naples 8.5 mi 19 min
Sugden Community Theatre 13.6 mi 33 min
Gulfshore Playhouse 13.8 mi 30 min
Music & Arts Community Center 23.7 mi 37 min
Barbara B. Mann Performing Arts Hall 27.9 mi 47 min
Name Miles ETA
Naples Comprehensive Health (North Naples Hospital) 5.9 mi 16 min
Naples Comprehensive Health (NCH Baker Downtown) 13.2 mi 31 min
Physicians Regional (Pine Ridge Rd.) 15.3 mi 28 min
Physicians Regional (Collier Blvd.) 24.3 mi 37 min
Name Miles ETA
Naples Airport (APF) 20.8 mi 34 min
SW Florida Int'l (RSW) 25.1 mi 37 min
Marco Island Executive Airport (MKY) 33.6 mi 52 min
Name Miles ETA
North Collier Regional Park 9.1 mi 24 min
Fred W. Coyle Freedom Park 12.5 mi 29 min
Gordon River Greenway 12.6 mi 28 min
Naples Zoo 12.9 mi 31 min
Baker Park 13.8 mi 31 min
Cambier Park 14 mi 34 min
Sugden Regional Park 16.9 mi 39 min
Naples Botanical Garden 17.2 mi 39 min
Big Corkscrew Island Regional Park 22 mi 42 min
Paradise Coast Sports Complex 22.3 mi 33 min

Destinations, Distances & ETAs

Name Miles ETA
Barefoot Beach Preserve 3.5 mi 9 min
Bonita Beach 3.7 mi 9 min
Delnor-Wiggins Pass State Park 4.1 mi 10 min
Vanderbilt Beach Park 5.2 mi 13 min
Pelican Bay Beach (Private) 7.5 mi 24 min
Lovers Key State Park 8.5 mi 19 min
Clam Pass Park 9 mi 24 min
Via Miramar Beach 11.8 mi 27 min
Lowdermilk Park 12.7 mi 29 min
Naples Municipal Beach and Pier 14.8 mi 36 min
Name Miles ETA
Mercato 6.3 mi 17 min
Galleria Shoppes at Vanderbilt 8 mi 21 min
Coconut Point 8.2 mi 23 min
Waterside Shops 8.6 mi 19 min
Venetian Village 10.7 mi 24 min
Coastland Mall 11.7 mi 28 min
5th Avenue South 13.5 mi 30 min
Miromar Outlets 14.5 mi 29 min
Third Street South 14.7 mi 35 min
Gulf Coast Town Center 18.6 mi 33 min
Name Miles ETA
Artis-Naples 8.5 mi 19 min
Sugden Community Theatre 13.6 mi 33 min
Gulfshore Playhouse 13.8 mi 30 min
Music & Arts Community Center 23.7 mi 37 min
Barbara B. Mann Performing Arts Hall 27.9 mi 47 min
Name Miles ETA
Naples Comprehensive Health (North Naples Hospital) 5.9 mi 16 min
Naples Comprehensive Health (NCH Baker Downtown) 13.2 mi 31 min
Physicians Regional (Pine Ridge Rd.) 15.3 mi 28 min
Physicians Regional (Collier Blvd.) 24.3 mi 37 min
Name Miles ETA
Naples Airport (APF) 20.8 mi 34 min
SW Florida Int'l (RSW) 25.1 mi 37 min
Marco Island Executive Airport (MKY) 33.6 mi 52 min
Name Miles ETA
North Collier Regional Park 9.1 mi 24 min
Fred W. Coyle Freedom Park 12.5 mi 29 min
Gordon River Greenway 12.6 mi 28 min
Naples Zoo 12.9 mi 31 min
Baker Park 13.8 mi 31 min
Cambier Park 14 mi 34 min
Sugden Regional Park 16.9 mi 39 min
Naples Botanical Garden 17.2 mi 39 min
Big Corkscrew Island Regional Park 22 mi 42 min
Paradise Coast Sports Complex 22.3 mi 33 min

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