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.
For sale
Price cut: $40K (11/13)
$9,950,000
185 Tupelo RD, NAPLES, FL 34108
6beds
13,474sqft
Est.:
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
- 40 days |
- 430 |
- 19 |
Zillow last checked: 9 hours ago
Listing updated: November 13, 2025 at 09:32am
Listed by:
Ashley Silvers 239-287-5206,
William Raveis Real Estate,
Dani Sinclair 239-595-6098,
William Raveis Real Estate
Source: SWFLMLS,MLS#: 225079634
Originating MLS: Naples
Originating MLS: NaplesTour 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
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 11/13/2025 | Price change | $9,950,000-0.4%$738/sqft |
Source:  SWFLMLS #225079634 Report a problem | ||
| 6/3/2025 | Price change | $9,990,000-0.1%$741/sqft |
Source: SWFLMLS #223064539 Report a problem | ||
| 9/11/2023 | Listed for sale | $10,000,000+0.1%$742/sqft |
Source: SWFLMLS #223064539 Report a problem | ||
| 8/20/2023 | Listing removed | -- |
Source: NABOR FL #222068927 Report a problem | ||
| 8/17/2023 | Listing removed | -- |
Source: SWFLMLS #222071975 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax 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% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$61,124/mo
Principal & interest
$49598
Property taxes
$8043
Home insurance
$3483
Climate risks
Neighborhood: Pine Ridge
Nearby schools
GreatSchools rating
- 10/10Sea Gate Elementary SchoolGrades: PK-5Distance: 2.7 mi
- 9/10Pine Ridge Middle SchoolGrades: 6-8Distance: 2.3 mi
- 8/10Barron Collier High SchoolGrades: 9-12Distance: 2.9 mi
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.
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