185 Tupelo Road, Naples, FL 34108
For Sale $9,950,000
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Scheduled Open Houses
2026-02-01 12:00 pm - 3:00 pm
2026-01-25 12:00 pm - 3:00 pm
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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.
Attic
Wet Bar
Breakfast Bar
Built In Features
Breakfast Area
Bathtub
Tray Ceilings
Closet Cabinetry
Coffered Ceilings
Separate Formal Dining Room
Dual Sinks
Entrance Foyer
Eat In Kitchen
Family Dining Room
French Doors Atrium Doors
Fireplace
High Ceilings
Jetted Tub
Kitchen Island
Living Dining Room
Multiple Shower Heads
Taxes: $24,558.09
Tax Year: 2024
Courtyard
Security High Impact Doors
Sprinkler Irrigation
Outdoor Grill
Outdoor Kitchen
Storage
Shutters Electric
Water Feature
Gas Grill
Built In Oven
Double Oven
Dryer
Dishwasher
Freezer
Gas Cooktop
Disposal
Microwave
Refrigerator
Self Cleaning Oven
Wine Cooler
Warming Drawer
Washer
Elementary School: Seagate
Middle School: Pine Ridge
Junior High: Pine Ridge
High School: Barron Collier
Building Description: Courtyard, Florida, Two Story
MLS Area: Na13 - Pine Ridge Area
Total Square Footage: 21,262
Total Floors: 2
Water: Public
Construction: Block, Concrete, Stucco
Date Listed: 2025-11-13 12:30:42
Pool: Y
Pool Description: Concrete, Electric Heat, Heated, In Ground, Pool Equipment, Screen Enclosure, Outside Bath Access, Pool Spa Combo
Private Spa: Y
Furnished: Unfurnished
Den: Y
Windows: Display Windows, Single Hung, Sliding, Impact Glass, Window Coverings
Parking: Attached, Circular Driveway, Driveway, Garage, Paved, Garage Door Opener
Garage Description: Y
Garage Spaces: 4
Attached Garage: Y
Flooring: Carpet, Tile, Wood
Roof: Tile
Heating: Central, Electric
Cooling: Central Air, Electric
Fireplace: Y
Security: Security System Owned, Burglar Alarm Monitored, Key Card Entry, Security System, Smoke Detectors
Laundry: Inside, Laundry Tub
Irrigation: Municipal
Pets: Yes
Sewer: Septic Tank
Lot Desc.: Oversized Lot, Dead End, Sprinklers Automatic
Listing Courtesy Of: William Raveis Real Estate
ashley.silvers@raveis.com
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.
Property Details
Price: $9,950,000
Sq Ft: 13,474
($738 per sqft)
Bedrooms: 6
Bathrooms: 9
Partial Baths: 1
Unit On Floor: 1
City: Naples
County: Collier
Type: Single Family
Development: Pine Ridge
Acres: 1.17
Year Built: 2005
Listing Number: 225079634
Status Code: A-Active
Taxes: $24,558.09
Tax Year: 2024
Garage:
4.00
/
Y
Furnishings: Unfurnished
Pets Allowed: Yes
Interior Features:
Attic
Wet Bar
Breakfast Bar
Built In Features
Breakfast Area
Bathtub
Tray Ceilings
Closet Cabinetry
Coffered Ceilings
Separate Formal Dining Room
Dual Sinks
Entrance Foyer
Eat In Kitchen
Family Dining Room
French Doors Atrium Doors
Fireplace
High Ceilings
Jetted Tub
Kitchen Island
Living Dining Room
Multiple Shower Heads
Financial Information:
Taxes: $24,558.09
Tax Year: 2024
Exterior Features:
Courtyard
Security High Impact Doors
Sprinkler Irrigation
Outdoor Grill
Outdoor Kitchen
Storage
Shutters Electric
Water Feature
Gas Grill
Equipment:
Built In Oven
Double Oven
Dryer
Dishwasher
Freezer
Gas Cooktop
Disposal
Microwave
Refrigerator
Self Cleaning Oven
Wine Cooler
Warming Drawer
Washer
School Information:
Elementary School: Seagate
Middle School: Pine Ridge
Junior High: Pine Ridge
High School: Barron Collier
Additional Information:
Building Description: Courtyard, Florida, Two Story
MLS Area: Na13 - Pine Ridge Area
Total Square Footage: 21,262
Total Floors: 2
Water: Public
Construction: Block, Concrete, Stucco
Date Listed: 2025-11-13 12:30:42
Pool: Y
Pool Description: Concrete, Electric Heat, Heated, In Ground, Pool Equipment, Screen Enclosure, Outside Bath Access, Pool Spa Combo
Private Spa: Y
Furnished: Unfurnished
Den: Y
Windows: Display Windows, Single Hung, Sliding, Impact Glass, Window Coverings
Parking: Attached, Circular Driveway, Driveway, Garage, Paved, Garage Door Opener
Garage Description: Y
Garage Spaces: 4
Attached Garage: Y
Flooring: Carpet, Tile, Wood
Roof: Tile
Heating: Central, Electric
Cooling: Central Air, Electric
Fireplace: Y
Security: Security System Owned, Burglar Alarm Monitored, Key Card Entry, Security System, Smoke Detectors
Laundry: Inside, Laundry Tub
Irrigation: Municipal
Pets: Yes
Sewer: Septic Tank
Lot Desc.: Oversized Lot, Dead End, Sprinklers Automatic
Map of 185 Tupelo Road, Naples, FL 34108
Listing Courtesy Of: William Raveis Real Estate
ashley.silvers@raveis.com