185 Tupelo Road, Naples, FL 34108 - SW Florida Gulf Coast Properties

$9,950,000

A true Pine Ridge compound, 185 Tupelo Road is designed for people who live, host, and work on a large scale. Set on a secluded 1.17-acre homesite, this residence offers approximately 13,474 square feet under air (over 21,000 square feet total), with 12 bedrooms, 9.5 baths, two full guest houses,… Read More a private theater, and resort-style outdoor living. Inside the main home, a grand entry opens to multiple living and dining areas that comfortably handle everything from everyday life to large gatherings. The central kitchen is outfitted with professional-grade Viking appliances, a prep island, and an expansive butler’s pantry with wine and bar service, anchoring the home for serious cooking and effortless entertaining. The floor plan offers tremendous flexibility with numerous additional rooms for offices, playrooms, fitness, or creative spaces. The spacious primary suite includes a sitting area, dual walk-in closets, and a spa-style bath with soaking tub and multi-head shower. Two separate guest houses/in-law suites make this property stand out. Each offers its own living room, kitchenette, bedroom, and bath, ideal for long-term guests, multi-generational living, staff, or a private work retreat - while maintaining privacy from the main residence. At the heart of the property is a dramatic courtyard with a free-form lagoon pool, waterfall grotto, integrated spa, and generous deck space for lounging in the sun or shade. An outdoor kitchen with built-in grill and bar seating makes entertaining simple, while a pool bath, cedar-lined sauna, and separate steam shower turn the courtyard into a true at-home resort. A dedicated home theater with multi-level seating and immersive sound delivers a true cinema experience without ever leaving the property. Practical features include a four-car garage, mudroom, dual laundry areas, and a discreet service corridor to keep daily life and larger events running smoothly. Located in highly sought-after Pine Ridge Estates, minutes to Naples’ Gulf beaches, Waterside Shops, Mercato, fine dining, and cultural venues - 185 Tupelo Road offers the scale of a private estate with the convenience of an in-town address. A rare opportunity for buyers seeking space, privacy, and versatility in one of Naples’ most coveted neighborhoods. Read Less

Courtesy of Ashley Silvers, William Raveis Real Estate.

Listing Snapshot

Days Online

Last Updated

Nov 23, 2025

Property Type

SingleFamilyResidence

Beds

Full Baths

Partial Baths

Square Ft.

13,474

Lot Size

1.17 Acres

Year Built

2005

MLS Number

225079634

30 Days Snapshot Of 34108

$1.74M

+13%

(avg) sold price

-13%

homes sold

163

-8%

(avg) days on market

Snapshot

Area Map

Additional Details

Property Access

Road responsibility: PublicMaintainedRoad, Road surface type: Paved

Appliances & Equipment

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

Building

Built in 2005, Architectural style: Courtyard, Florida, TwoStory, Construction materials: Block, Concrete, Stucco, Levels: Two, 2, 2 total stories, Other structures: Outbuilding, Toal building area: 21262

Community

NonGated

Cooling

CentralAir, Electric

Doors

FrenchDoors, SlidingDoors

Exterior Features

Courtyard, SecurityHighImpactDoors, SprinklerIrrigation, OutdoorGrill, OutdoorKitchen, Storage, ShuttersElectric, WaterFeature, GasGrill

Floors

Carpet, Tile, Wood

Garage

4 garage spaces

Water Features

None

Heating

Central, Electric

Interior Features

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

Laundry

Inside, LaundryTub

Lot

1.17 acres, OversizedLot, DeadEnd, SprinklersAutomatic

Parking

4 covered spaces, Attached, CircularDriveway, Driveway, Garage, Paved, GarageDoorOpener

Pets Policy

Horse amenities: HorsesAllowed, Yes

Pool

Concrete, ElectricHeat, Heated, InGround, PoolEquipment, ScreenEnclosure, OutsideBathAccess, PoolSpaCombo

Property

Patio and porch features: Balcony, Lanai, Open, Porch, Screened, Landscaped

Roof

Tile

Security Features

SecuritySystemOwned, BurglarAlarmMonitored, KeyCardEntry, SecuritySystem, SmokeDetectors

Sewer

SepticTank

Spa

ElectricHeat, Gunite, InGround, Screened

Taxes

Year: 2024

Utilities

CableAvailable, NaturalGasAvailable, HighSpeedInternetAvailable, UndergroundUtilities

Windows

DisplayWindows, SingleHung, Sliding, ImpactGlass, WindowCoverings

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