185 Tupelo RD, NAPLES, FL 34108 - Naples Life & Homes

$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

Listing courtesy of William Raveis Real Estate.

Listing Snapshot

Days Online

Last Updated

Nov 25, 2025

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

21,262

Lot Size

1.17 Acres

Year Built

2005

MLS Number

225079634

30 Days Snapshot Of 34108

$1.59M

-41%

(avg) sold price

-50%

homes sold

211

+39%

(avg) days on market

Snapshot

Area Map

Additional Details

Property Access

Road surface type: "Paved"

Appliances & Equipment

"Gas Cooktop", "Dishwasher", "Disposal", "Double Oven", "Dryer", "Grill - Gas", "Microwave", "Refrigerator/Freezer", "Self Cleaning Oven", "Wall Oven", "Warming Tray", "Washer", "Wine Cooler"

Building

Built in 2005, Building area units: Square Feet, 1 total unit, Living area: 13,474, Construction materials: "Concrete Block", "Stucco", Other structures: "Outdoor Kitchen", "Storage", 2 total stories, "DSL/Cable Available"

Cooling

"Central Electric"

Doors

"French Doors", "Zero/Corner Door Sliders"

Exterior Features

"Balcony", "Open Porch/Lanai", "Screened Lanai/Porch", "Built In Grill", "Courtyard", "Outdoor Kitchen", "Storage"

Floors

"Carpet", "Tile", "Wood"

Garage

4 spaces

Heating

"Central Electric"

Interior Features

Furnished: Unfurnished, "Bar", "Built-In Cabinets", "Closet Cabinets", "Coffered Ceiling(s)", "Custom Mirrors", "Fireplace", "Foyer", "French Doors", "Laundry Tub", "Pantry", "Pull Down Stairs", "Smoke Detectors", "Wired for Sound", "Tray Ceiling(s)", "Vaulted Ceiling(s)", "Volume Ceiling", "Walk-In Closet(s)", "Wet Bar", "Window Coverings", "Zero/Corner Door Sliders"

Laundry

"Laundry in Residence", "Laundry Tub"

Lot

1.17 acres, 50,965 square feet, "Oversize"

Parking

4 covered spaces, 4 total parkings, "Circular Driveway", "Driveway Paved", "Attached"

Pets Policy

Pets allowed: "Yes"

Pool

"Pool/Spa Combo", "Below Ground", "Concrete", "Custom Upgrades", "Equipment Stays", "Electric Heat", "Pool Bath", "Screen Enclosure"

Property

"None", "Landscaped Area"

Roof

"Tile"

Security Features

"Security System", "Smoke Detector(s)"

Sewer

"Septic Tank"

Spa

"Below Ground", "Concrete", "Equipment Stays", "Heated Electric", "Pool Bath", "Pool Integrated", "Screened", "Jetted Tub"

Taxes

Tax annual amount: $24,558, Tax year: 2024

Windows

"Window Coverings"

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