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185 Tupelo Rd, Naples, FL 34108
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185 Tupelo Rd, Naples, FL 34108 - 6 Bedroom Pool Home in Pine Ridge
$9,950,000
MLS Number
225079634
Bedrooms
6 or More
Bathrooms
9 Baths + 1 Half
Living Area
13,474 sq ft
Total Area
21,262 sq ft
Garage Spaces
4
Year Built
2005
Days on Market
61
home Property Description
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, 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.
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.
fact_check The Basics
Property Type
Single Family
Gulf Access
No
Private Pool
Yes
Private Spa
Yes
Acres
1.17
Furnished
Unfurnished
Last Modified
2 months ago
roofing Building Features
Building Features
DSL/Cable Available
Building Style
2 Story, Florida
Construction Materials
Concrete Block, Stucco
Cooling
Central Electric
Covered Spaces
4
Elevator
None
Floor Plan
Courtyard, Great Room, 2 Story
Floors
2
Garage Spaces
4
Other Structures
Outdoor Kitchen, Storage
Rear Exposure
North
Roof
Tile
Security Features
Security System, Smoke Detector(s)
Storm Protection
Impact Resistant Doors, Impact Resistant Windows, Shutters Electric
View
Landscaped Area
Water Source
Central
Window Features
Window Coverings
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chair Interior Features
Appliances & Equipment
Auto Garage Door, Cooktop - Gas, Dishwasher, Disposal, Double Oven, Dryer, Grill - Gas, Microwave, Refrigerator/Freezer, Security System, Self Cleaning Oven, Smoke Detector, Wall Oven, Warming Tray, Washer, Wine Cooler
Interior Features
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
Additional Rooms
Balcony, Den - Study, Exercise, Family Room, Great Room, Guest Bath, Guest Room, Home Office, Laundry in Residence, Media Room, Open Porch/Lanai, Recreation, Screened Lanai/Porch, Workshop
Kitchen Features
Built-In Desk, Gas Available, Island, Pantry, Walk-In Pantry
Flooring
Carpet, Tile, Wood
Gas
Yes
Laundry
Laundry in Residence, Laundry Tub
holiday_village Neighborhood and Community
Pets Allowed
Yes
Amenities
Underground Utility
Neighborhood
Pine Ridge
Neighborhood Type
Non-Gated
Included in Fees
None
HOA Restrictions
None
school School Zones
Elementary School
Seagate
Middle School
Pine Ridge
High School
Barron Collier
Chris Farrugia, M.B.A.
Realtor® at The Listing Naples Group
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The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS organizations. Copyright 2026 Southwest Florida MLS organizations. 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.
Listing provided by William Raveis Real Estate.
