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185 Tupelo Road

Naples, FL 34108

6 beds
10 baths
13,474 sqft
1 sqft lot
$741 per sqft
2005 build
– on site

One Property. Many Possibilities. Welcome to an unparalleled legacy estate spanning 13,474 sq/ft under air (over 21,000 sq/ft total) on a secluded 1.17-acre parcel in the prestigious Pine Ridge Estates. With 12 bedrooms and 9½ baths, this architectural masterpiece delivers privacy, style and sophistication for multigenerational living, grand-scale entertaining and bespoke work, wellness, or creative zones. Grand Arrival & Formal Entertaining Enter through wrought iron double doors into a soaring foyer flanked by a luminous living salon and a formal dining pavilion beneath a sculptural chandelier. Hand troweled walls, custom millwork and gallery style lighting evoke timeless craftsmanship and hospitality. Culinary Heart & Casual Gathering The chef’s domain boasts professional grade Viking appliances, prep island, expansive butler’s pantry complete with wine and bar station. A breakfast nook beneath a tray ceiling opens seamlessly to the courtyard. Resort Style Outdoor Living The central courtyard reveals an impressive free form lagoon pool, waterfall grotto and integrated spa. An outdoor kitchen with built in grill, stone topped bar seating and alfresco dining invites endless possibilities for lounging and entertaining under the Florida sun. A pool bath, cedar lined sauna and separate steam shower complete this private resort experience. Resting Places A serene primary suite features bay window seating, dual walk-in closets and a spa bath with a deep soaking tub and lux shower with multiple shower heads. This residence was designed for large scale hosting and quiet moments alike—with over eleven additional beautifully styled private zones for sleeping, lounging, or working in peace. Cinema, Service & Convenience This estate also boasts a state-of-the-art home theater, multi-level posh seating, cinematic sound system creates the ultimate cinematic experience in the comfort of your own home. A four-car garage, mudroom, dual laundry stations and discreet service corridor maintain impeccable flow for daily living or staffed events. A DESIRABLE ADDRESS Consistently ranked #1 Best Place to Live and #1 Best Place to Retire by U.S. News & World Report, Naples is celebrated for its world class white sand beaches and championship golf—aptly nicknamed the “Golf Capital of the World.” Waterside Shops and Mercato offer haute couture retail, while award winning restaurants and curated arts venues enrich daily life. Private beach clubs, pro level sporting events and an elevated social scene ensure every desire is fulfilled. Moments from beaches, cultural attractions, and world-renowned golf, this is a rare legacy estate for those whose vision of home embraces style, scale, and the power to bring people together. 185 Tupelo Road represents unparalleled value—offering the lowest price per square foot of any home available in Pine Ridge, making it a compelling investment for discerning buyers. One home. Endless opportunity.

Listing courtesy of FGCMLS / John R Wood Properties

Last checked: Checking… • Last updated Jun 3, 2025 •

MLS# 223064539 —

This home is listed in more than one place. See it here.

The Building

Year Built:

2005
Construction Materials:

Block,Concrete,Stucco
Building Area Total:

21262.0
Building Area Source:

Appraiser
Architectural Style:

MultiLevel,Other,TwoStory
Roof:

Tile
Exterior Features:

Courtyard,SecurityHighImpactDoors,SprinklerIrrigation,OutdoorKitchen,Storage,ShuttersElectric,GasGrill
Door Features:

FrenchDoors
Window Features:

SingleHung,Sliding,ImpactGlass,WindowCoverings
Patio And Porch Features:

Lanai,Porch,Screened
Security Features:

SecuritySystemOwned,BurglarAlarmMonitored,KeyCardEntry,SecuritySystem,SmokeDetectors
Stories:

2
Stories Total:

2
Entry Level:

1
Levels:

Two
Direction Faces:

South

Interior

Interior Features:

Attic,WetBar,BreakfastBar,BuiltInFeatures,BedroomOnMainLevel,BreakfastArea,Bathtub,TrayCeilings,ClosetCabinetry,CofferedCeilings,SeparateFormalDiningRoom,DualSinks,EntranceFoyer,EatInKitchen,FamilyDiningRoom,FrenchDoorsAtriumDoors,Fireplace,HighCeilings,JettedTub,KitchenIsland,LivingDiningRoom
Furnished:

Unfurnished
Flooring:

Carpet,Tile,Wood
Fireplace:

true
Laundry Features:

Inside,LaundryTub

Room Dimensions

Living Area:

13474.0
Living Area Source:

Appraiser

Financial & Terms

Possession:

CloseOfEscrow

Location

Latitude:

26.247917
Longitude:

-81.79356

The Property

Property Type:

Residential
Property Subtype:

SingleFamilyResidence
Property Subtype Additional:

SingleFamilyResidence
Property Condition:

Resale
View:

Landscaped,Pool,Water
Lot Features:

IrregularLot,SprinklersAutomatic
Lot Size Acres:

1.17
Lot Size Area:

1.17
Lot Size Units:

Acres
Lot Size Source:

Appraiser
Lot Size Dimensions:

170 x 274 x 175 x 319
Lot Dimensions Source:

Appraiser
Parcel Number:

67341400001
Waterfront:

false
Waterfront Features:

None
Road Surface Type:

Paved

Listing Agent

Contact info:

Taxes

Tax Year:

2022
Tax Lot:

16
Tax Legal Description:

PINE RIDGE 2ND EXT BLK 2 LOT 16
Tax Annual Amount:

25214.14

Beds

Total Bedrooms:

6

Baths

Total Baths:

10
Half Baths:

1
Full Baths:

9

The Listing

Virtual Tour URL Unbranded:

https://listings.boutiqueimagery.com/sites/ymwjwva/unbranded

Heating & Cooling

Heating:

Central,Electric
Heating:

true
Cooling:

CentralAir,Electric
Cooling:

true

Utilities

Utilities:

CableAvailable,NaturalGasAvailable,HighSpeedInternetAvailable,UndergroundUtilities
Sewer:

SepticTank
Water Source:

Public

Appliances

Appliances:

BuiltInOven,DoubleOven,Dryer,Dishwasher,Freezer,GasCooktop,Disposal,Microwave,Refrigerator,SelfCleaningOven,WineCooler,Washer

Schools

Elementary School:

SEAGATE
Middle Or Junior School:

PINE RIDGE
High School:

BARRON COLLIER

The Community

Subdivision Name:

PINE RIDGE
Community Features:

NonGated
# of Units In Community:

1
Association:

false
Association Fee Includes:

None
Association Amenities:

None,SeeRemarks
Spa:

true
Spa Features:

ElectricHeat,Gunite,InGround
Pool Features:

Concrete,ElectricHeat,Heated,InGround,PoolEquipment,OutsideBathAccess
Pool Private:

true
Pets Allowed:

Yes

Parking

Garage:

true
Garage Spaces:

4.0
Attached Garage:

true
Carport:

false
Covered Spaces:

4.0
Parking Features:

Attached,CircularDriveway,Driveway,Garage,Paved,GarageDoorOpener

Monthly cost estimate

Asking price

$9,990,000

Expense	Monthly cost
Mortgage	$53,493
Taxes	$2,101
Insurance	$2,747
Utilities	$566 See report
Total	$58,907/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

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This house located in North Naples, Pine Ridge, FL 34108 is currently for sale for $9,990,000. 185 Tupelo Road is a 13,474 square foot house with 6 beds and 10 baths that has been on Estately for 348 days. 185 Tupelo Road is in the North Naples neighborhood of Pine Ridge and has a WalkScore® of 7, making it car-dependent. This house is in the attendance area of Pine Ridge Middle School, Sea Gate Elementary School, and Barron Collier High School.

Listing Courtesy of: FGCMLS and John R Wood Properties. Data displayed here has not been verified by Estately. Disclaimers