Skip main navigation
For sale
    • $9,950,000

    185 Tupelo RD, NAPLES, FL 34108

    6beds
    13,474sqft
    : 
    Single Family Residence
    Built in 2005
    1.17 Acres Lot
    $-- Zestimate®
    $738/sqft
    $-- HOA

    What's special

    Prep islandWaterfall grottoFour-car garageResort-style outdoor livingDiscreet service corridorDual laundry areasCedar-lined sauna
    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.
    136 days
    |
    511
    |
    17
    |

    Zillow last checked: 7 hours ago

    Listing updated: January 26, 2026 at 10:16am

    Listed by:

    Ashley Silvers 239-287-5206,

    William Raveis Real Estate,

    Dani Sinclair 239-595-6098,

    William Raveis Real Estate

    Source: SWFLMLS,MLS#: 225079634MLS LogoOriginating MLS: Naples

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 10
      • Full bathrooms: 9
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Balcony, Den - Study, Exercise Room, Family Room, Great Room, Guest Bath, Guest Room, Office, Media Room, Open Porch/Lanai, Recreation, Screened Lanai/Porch, Workshop, 6 or More Beds
      Dining room
      • Features: Breakfast Bar, Breakfast Room, Dining - Family, Dining - Living, Eat-in Kitchen, Formal
      Kitchen
      • Features: Built-In Desk, Gas Available, Island, Pantry, Walk-In Pantry
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Grill - Gas, Microwave, Refrigerator/Freezer, Self Cleaning Oven, Oven, Warming Tray, Washer, Wine Cooler
      • Laundry: Inside, Laundry Tub
      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, 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
      • Flooring: Carpet, Tile, Wood
      • Doors: French Doors, Zero/Corner Door Sliders, Impact Resistant Doors
      • Windows: Window Coverings, Impact Resistant Windows, Shutters Electric
      • Has fireplace: Yes
      Interior area
      • Total structure area: 21,262
      • Total interior livable area: 13,474 sqft

      Property

      Parking
      • Total spaces: 4
      • Parking features: Circular Driveway, Driveway, Attached
      • Attached garage spaces: 4
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Open Porch/Lanai, Screened Lanai/Porch
      • Exterior features: Balcony, Outdoor Grill, Courtyard, Outdoor Kitchen, Storage
      • Has private pool: Yes
      • Pool features: Pool/Spa Combo, In Ground, Concrete, Custom Upgrades, Equipment Stays, Electric Heat, Pool Bath, Screen Enclosure
      • Has spa: Yes
      • Spa features: In Ground, Concrete, Equipment Stays, Heated, Pool Bath, Pool Integrated, Screened, Bath
      • Has view: Yes
      • View description: Landscaped Area
      • Waterfront features: None
      Lot
      • Size: 1.17 Acres
      • Features: Oversize
      Details
      • Additional structures: Outdoor Kitchen, Storage
      • Parcel number: 67341400001
      • Horses can be raised: Yes

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Florida
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Concrete Block
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 2005

      Utilities & green energy

      • Gas: Propane
      • Sewer: Septic Tank
      • Water: Central

      Community & HOA

      Community
      • Features: Non-Gated
      • Security: Security System, Smoke Detector(s)
      • Subdivision: PINE RIDGE
      HOA
      • Has HOA: No
      • Amenities included: Underground Utility
      Location
      • Region: Naples

      Financial & listing details

      • Price per square foot: $738/sqft
      • Tax assessed value: $5,019,102
      • Annual tax amount: $24,558
      • Date on market: 11/13/2025
      • Lease term: Buyer Finance/Cash
      • Road surface type: Paved
      Get pre-qualifiedBe ready to make an offer.
      Connect with an agentGet info on this home, tour, and more.
      Calculate monthly paymentSee if you can afford this home.

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        Price history
        DateEventPrice
        11/13/2025Price change$9,950,000-0.4%$738/sqft
        Source: SWFLMLS #225079634 Report a problem
        6/3/2025Price change$9,990,000-0.1%$741/sqft
        Source: SWFLMLS #223064539 Report a problem
        9/11/2023Listed for sale$10,000,000+0.1%$742/sqft
        Source: SWFLMLS #223064539 Report a problem
        8/20/2023Listing removed--
        Source: NABOR FL #222068927 Report a problem
        8/17/2023Listing removed--
        Source: SWFLMLS #222071975 Report a problem
        7/31/2023Listed for rent$85,000$6/sqft
        Source: NABOR FL #222068927 Report a problem
        1/10/2023Price change$9,995,000-8.3%$742/sqft
        Source: SWFLMLS #222071975 Report a problem
        10/3/2022Listed for sale$10,900,000-12.8%$809/sqft
        Source: SWFLMLS #222071975 Report a problem
        8/4/2022Listing removed--
        Source: Douglas Elliman Report a problem
        3/4/2022Listed for sale$12,500,000+212.5%$928/sqft
        Source: Stellar MLS #C7455295 Report a problem
        3/3/2021Listing removed--
        Source: SWFLMLS #219083483 Report a problem
        10/26/2020Price change$4,000,000-10.1%$297/sqft
        Source: Compass Florida LLC #219083483 Report a problem
        8/19/2020Price change$4,450,000-8.7%$330/sqft
        Source: Compass Florida LLC #219083483 Report a problem
        3/6/2020Price change$4,875,000+2.6%$362/sqft
        Source: Compass Florida Naples #219083483 Report a problem
        3/5/2020Price change$4,750,000-20.2%$353/sqft
        Source: Compass Florida Naples #219083483 Report a problem
        1/11/2020Listed for sale$5,950,000-8.5%$442/sqft
        Source: Compass Florida Naples #219083483 Report a problem
        12/14/2019Listing removed$6,500,000$482/sqft
        Source: Premiere Plus Realty Co. #219017487 Report a problem
        3/8/2019Listed for sale$6,500,000+30%$482/sqft
        Source: Premiere Plus Realty Co. #219017487 Report a problem
        9/14/2018Listing removed$4,999,000$371/sqft
        Source: Allison James Estates & Homes #218035678 Report a problem
        2/2/2018Listed for sale$4,999,000-9.1%$371/sqft
        Source: Gulf Breeze Real Estate LC #218009292 Report a problem
        9/3/2017Listing removed$5,499,000$408/sqft
        Source: Premiere Plus Realty Co. #216033010 Report a problem
        10/13/2014Listed for sale$5,499,000-4.4%$408/sqft
        Source: Premiere Plus Realty, Co. #214053627 Report a problem
        7/15/2014Listing removed$5,750,000$427/sqft
        Source: Gulf Coast International Prop #214000739 Report a problem
        2/8/2014Listed for sale$5,750,000-17.3%$427/sqft
        Source: Gulf Coast International Prop #214000739 Report a problem
        10/4/2012Listing removed$6,950,000+2178.7%$516/sqft
        Source: Listhub #211513059 Report a problem
        10/10/1997Sold$305,000+4.4%$23/sqft
        Source: Public Record Report a problem
        12/5/1995Sold$292,200+6.6%$22/sqft
        Source: Public Record Report a problem
        7/5/1994Sold$274,000$20/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2024$24,558 +2.7%$2,551,485 +3%
        2023$23,922 -3.4%$2,477,170 +3%
        2022$24,753 -1.3%$2,405,019 +3%
        2021$25,070 +2.4%$2,334,970 +1.4%
        2020$24,474 +1.6%$2,302,732 +2.3%
        2019$24,096 +2.1%$2,250,960 +1.9%
        2018$23,597 -1.8%$2,208,989 +2.1%
        2017$24,024 +1.3%$2,163,554 +2.1%
        2016$23,708 +2.3%$2,119,054 +0.7%
        2015$23,174 -0.8%$2,104,324 +3.3%
        2014$23,363 +1.2%$2,037,623 +1.5%
        2013$23,085 +0.4%$2,006,771 +1.7%
        2012$22,990 -0.4%$1,972,390 -0.9%
        2011$23,078 -9.6%$1,990,918 -2.6%
        2010$25,528 -10.9%$2,044,545 -8.6%
        2009$28,638 $2,237,157 -17.7%
        2008$28,638 -23.1%$2,717,192 -15.7%
        2007$37,257 +637.4%$3,224,719 +2.5%
        2006$5,053 $3,146,067 +690.9%
        2005$5,053 +5.3%$397,800 +6.3%
        2004$4,797 -18.7%$374,400 -16.7%
        2003$5,899 +3.8%$449,504 +5.2%
        2002$5,682 -39.3%$427,216 +23.8%
        2001$9,366 +126.9%$345,163
        2000$4,128 --

        Find assessor info on the county website

        BuyAbility℠ payment

        Est. payment
        $58,759/mo
        Principal & interest
        $50716
        Property taxes
        $8043
        More affordability tools

          Climate risks

          Neighborhood: Pine Ridge

          Getting around

          6 / 100
          Car-Dependent
          51 / 100
          Bikeable

          Nearby schools

          GreatSchools rating
          Schools provided by the listing agent
          • Elementary: SEAGATE
          • Middle: PINE RIDGE
          • High: BARRON COLLIER

          Source: SWFLMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

          Skip to the end of the carouselSkip to the beginning of the carousel

          Local experts in 34108

          Similar homes

          Skip to the end of the carouselSkip to the beginning of the carousel

            Nearby cities

            Nearby neighborhoods

            Nearby zip codes

            Other Naples Topics