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253 Cheshire Way

Naples, FL 34110

$4,495,000

Status: For Sale

Type: Resale Property

Days on Site: 267

Listing ID: 225010140

4 Bed

4 Full Bath

& 2 ½ Bath

6,026 Sq. Ft.

Built: 2002

Furnishings: Negotiable

Virtual Tour
Contact Agent

239-450-3763

Total Annual Recurring Fees

$21,792

Total One Time Fees

$66,100

2024 Total Taxes

$22,833

List Price / Square Foot

$745.93

Community

Audubon

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

Exceptional Estate in Audubon Golf & Country Club

This meticulously updated estate combines timeless elegance with today’s most sought-after design features. With 4 bedrooms, 6 bathrooms, and sweeping southern golf course views, this residence embodies refined luxury inside and out.

As you arrive, a newly paved driveway leads to a stately entrance framed by fresh exterior and interior paint. Inside, soaring ceilings, gleaming marble floors, and custom finishes create an atmosphere of sophistication. Expansive pocketed sliding doors seamlessly blend indoor and outdoor living, opening to spectacular golf and pool views.

Gourmet Kitchen & Living Spaces
At the heart of the home lies the chef’s kitchen, featuring custom high-end cabinetry, professional-grade appliances, and dual oversized islands—perfect for cooking, entertaining, and gathering. The adjoining living and dining areas are bathed in natural light from floor-to-ceiling windows, enhancing the home’s open flow and panoramic views.

Owner’s Retreat
The luxurious main suite offers a private seating area that could double as an office. The newly remodeled spa-inspired bathroom showcases modern finishes, while his-and-hers bathrooms provide ultimate comfort and convenience.

Resort-Style Outdoor Living
Step outside to the newly renovated pool area with a sun shelf, spa, and spectacular golf course backdrop—an ideal setting for Florida sunsets. The separate gazebo with a fully equipped outdoor kitchen and bar creates the perfect entertaining space, while lush landscaping ensures privacy and tranquility year-round.

Guest Accommodations
A dedicated upstairs wing includes two elegant guest suites with private baths. A comfortable living room with kitchenette opens to a balcony offering panoramic Gulf Coast views—ideal for enjoying sunset skies.

Community & Amenities
Located within the private, gated Audubon Golf & Country Club, residents enjoy world-class amenities including an 18-hole championship golf course, tennis and pickleball courts, fitness center, heated lap pool, courtside café, and vibrant dining and social events. Nature lovers will appreciate the scenic trails and kayak launch that make Audubon truly unique.

Additional Highlights
Designer furnishings are available, allowing you to make this exceptional residence move-in ready.

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 10/22/2025 11:00am.

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 10 min
Bonita Beach 3.7 mi 10 min
Delnor-Wiggins Pass State Park 4.1 mi 10 min
Vanderbilt Beach Park 5.2 mi 14 min
Pelican Bay Beach (Private) 7.5 mi 25 min
Lovers Key State Park 8.5 mi 21 min
Clam Pass Park 9 mi 25 min
Via Miramar Beach 12.1 mi 28 min
Lowdermilk Park 12.9 mi 30 min
Naples Municipal Beach and Pier 15 mi 38 min
Name Miles ETA
Mercato 6.1 mi 17 min
Coconut Point 8.2 mi 24 min
Galleria Shoppes at Vanderbilt 8.3 mi 21 min
Waterside Shops 8.8 mi 20 min
Venetian Village 9.9 mi 26 min
Coastland Mall 12.7 mi 29 min
5th Avenue South 13.7 mi 32 min
Miromar Outlets 14.5 mi 34 min
Third Street South 14.9 mi 38 min
Gulf Coast Town Center 18.6 mi 35 min
Name Miles ETA
Artis-Naples 8.3 mi 22 min
Sugden Community Theatre 13.8 mi 34 min
Gulfshore Playhouse 14 mi 31 min
Music & Arts Community Center 23.7 mi 43 min
Barbara B. Mann Performing Arts Hall 27.9 mi 56 min
Name Miles ETA
Naples Comprehensive Health (North Naples Hospital) 5.5 mi 16 min
Physicians Regional (Pine Ridge Rd.) 13.2 mi 31 min
Naples Comprehensive Health (NCH Baker Downtown) 13.4 mi 32 min
Physicians Regional (Collier Blvd.) 24.3 mi 39 min
Name Miles ETA
Naples Airport (APF) 15.5 mi 34 min
SW Florida Int'l (RSW) 25.1 mi 41 min
Marco Island Executive Airport (MKY) 33.6 mi 55 min
Name Miles ETA
North Collier Regional Park 9.1 mi 25 min
Fred W. Coyle Freedom Park 12.8 mi 30 min
Gordon River Greenway 12.9 mi 28 min
Naples Zoo 13.2 mi 31 min
Baker Park 14.1 mi 31 min
Cambier Park 14.2 mi 35 min
Sugden Regional Park 17.1 mi 41 min
Naples Botanical Garden 17.4 mi 39 min
Big Corkscrew Island Regional Park 19.8 mi 43 min
Paradise Coast Sports Complex 22.3 mi 36 min

Destinations, Distances & ETAs

Name Miles ETA
Barefoot Beach Preserve 3.5 mi 10 min
Bonita Beach 3.7 mi 10 min
Delnor-Wiggins Pass State Park 4.1 mi 10 min
Vanderbilt Beach Park 5.2 mi 14 min
Pelican Bay Beach (Private) 7.5 mi 25 min
Lovers Key State Park 8.5 mi 21 min
Clam Pass Park 9 mi 25 min
Via Miramar Beach 12.1 mi 28 min
Lowdermilk Park 12.9 mi 30 min
Naples Municipal Beach and Pier 15 mi 38 min
Name Miles ETA
Mercato 6.1 mi 17 min
Coconut Point 8.2 mi 24 min
Galleria Shoppes at Vanderbilt 8.3 mi 21 min
Waterside Shops 8.8 mi 20 min
Venetian Village 9.9 mi 26 min
Coastland Mall 12.7 mi 29 min
5th Avenue South 13.7 mi 32 min
Miromar Outlets 14.5 mi 34 min
Third Street South 14.9 mi 38 min
Gulf Coast Town Center 18.6 mi 35 min
Name Miles ETA
Artis-Naples 8.3 mi 22 min
Sugden Community Theatre 13.8 mi 34 min
Gulfshore Playhouse 14 mi 31 min
Music & Arts Community Center 23.7 mi 43 min
Barbara B. Mann Performing Arts Hall 27.9 mi 56 min
Name Miles ETA
Naples Comprehensive Health (North Naples Hospital) 5.5 mi 16 min
Physicians Regional (Pine Ridge Rd.) 13.2 mi 31 min
Naples Comprehensive Health (NCH Baker Downtown) 13.4 mi 32 min
Physicians Regional (Collier Blvd.) 24.3 mi 39 min
Name Miles ETA
Naples Airport (APF) 15.5 mi 34 min
SW Florida Int'l (RSW) 25.1 mi 41 min
Marco Island Executive Airport (MKY) 33.6 mi 55 min
Name Miles ETA
North Collier Regional Park 9.1 mi 25 min
Fred W. Coyle Freedom Park 12.8 mi 30 min
Gordon River Greenway 12.9 mi 28 min
Naples Zoo 13.2 mi 31 min
Baker Park 14.1 mi 31 min
Cambier Park 14.2 mi 35 min
Sugden Regional Park 17.1 mi 41 min
Naples Botanical Garden 17.4 mi 39 min
Big Corkscrew Island Regional Park 19.8 mi 43 min
Paradise Coast Sports Complex 22.3 mi 36 min

Please flip your mobile to landscape view or use a device with a larger screen to see these destinations mapped.

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