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185 Tupelo, Naples, FL 34108

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For Sale

$9,950,000

6 beds • 9 baths • 1 half baths • 13,474 sqft

Estimated Payment

$      /mo. †

APR for 30 years

Change Loan Terms

  • Single Family Detached
    Property type

  • Newly Listed
    Time on Century 21

  • $738.46
    Price per square foot

  • 11-20 Years Old
    Age

Explore this Property

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.
MLS# 225079634

Courtesy Of William Raveis Real Estate

(239) 231-3380

Property Features

  • Age
    11-20 Years Old
  • Amenities
    Porch, Vaulted Ceiling, Wet Bar
  • Appliances
    Cooktop, Cooktop - Gas, Dishwasher, Dryer, Freezer, Garbage Disposer, Microwave, Oven - Double, Refrigerator, Washer
  • Architecture Style
    Other
  • Exterior Type
    Block, Concrete, Stucco
  • Fireplace
    Fireplace
  • Floor Covering
    Carpet, Tile, Wood
  • Lot Size
    1.17 Acres
  • Roof Type
    Tile

Map and Directions

Directions to 185 Tupelo, Naples, FL 34108

Home seller CENTURY 21 SUNBELT REALTY

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(239) 561-5645
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Copyright © 2025 Naples Area Board of REALTORS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.