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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$40,000,000
88835 & 88845 Old Highway
Plantation Key, FL 33070
MLS# 619826
8 beds  |  11 baths  |  9704 sqft


88835 & 88845
  1 / 48  
88835 & 88845 Oceanfront Compound Aerial View Main House Main House Entryway Main Entry Living Space Living Space Kitchen Kitchen Dining Primary Bedroom Primary Bedroom Primary Bathroom Primary Bathroom Bedroom 2 Upstairs Upstairs Bedroom 3 Bathroom Bathroom Balcony Bedroom 4 Laundry Elevator Pool Beach Access Spa Pool 3 Car Garage Property Entrances House 2 Entrance Living Room Living Room Kitchen Kitchen Primary Bedroom Primary Bedroom Primary Bathroom Guest Bedroom Full Bathroom 2 Half Bathroom Patio Private Boat Basin Aerial Amenity Rendering

Property Description
A rare dual-offering on coveted Millionaire's Row in Tavernier, this extraordinary oceanfront compound spans over multiple acres across two parcels-delivering an unmatched combination of scale, privacy, and future development flexibility in the Florida Keys. At 88845, a newly constructed 8,200SF estate sets a new standard for modern coastal luxury. Thoughtfully designed for both grand entertaining and private retreat, the residence offers 5 bedrooms, 6 full baths & 2 half baths, complemented by a dedicated office, control room, mudroom, and expansive 3-car garage with climate-controlled workshop. Interior finishes are curated at the highest level, including white diamond marble, teak wood flooring, custom millwork & a vapor fireplace, while a full-home sound system, elevator & advanced mechanical infrastructure provide seamless functionality. The chef's kitchen is equipped with top-tier Wolf, SubZero, & Cove appliances, dual dishwashers, farmhouse sinks, refrigerated drawers, wine storage & custom mahogany countertops-designed to accommodate both everyday living and large-scale entertaining. Outdoor living is equally impressive, anchored by a 120-foot resort-style pool with integrated spa, heating & chilling systems, & full smart control. A fully equipped summer kitchen, cabana bath, & multiple covered terraces create a true waterfront lifestyle experience. With 480 feet of water frontage, the protected basin offers exceptional boating capabilities, including 90 feet of dockage & room to expand, a 20,000lb lift, boat ramp & deep-water access. The adjacent parcel at 88835 provides over 3 acres of additional opportunity featuring a renovated 3-bedroom residence completed in 2022, with a transferable TDR allowing for the development of a substantially larger primary home. The property also includes a buildable lot & natural hammock buffer for added privacy. Together, these two properties present a generational opportunity to own a one of a kind waterfront compound.

Details
Maps
Contract Information
Listing Board: Florida Keys
As is Rght to Inspct: Yes
Current Price: $40,000,000
Listing Date: 2026-05-08
List Price: $40,000,000
Location, Tax & Legal
City: Tavernier
Mile Marker: 89
Marathon Neighborhood: N/A
Side: Ocean
Flood Zone: AE,AE,VE,VE,AE,0.2 P
Alternate Key #: 1511498
Parcel #: 00415240-000000
Zoning: RE - Residential Estate
Deed Restrictions: Unknown
Legal: LT 2 PEARL CITY PLANTATION KEY PB2-134 G43-412 G75-103 OR455-470 OR710-894 OR762-729 OR793-1145 OR831-2031 OR921-314 OR9
Taxes: 28698
Tax Year: 2025
Pub Sewer HkUp: Yes
Street #: 88835
Street Name: & 88845 Old
Street Suffix: Highway
Key/Island: Plantation Key
State/Province: FL
Zip Code: 33070
County: Monroe
Subdivision: Pearl City (89.0)
Area: 25 - Plantation Key
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 8
Lot Size: X
Lot SqFt: 183017
Pool: Yes
Lot Sqft Source: Property Data Card
Total Units: 0
Acres: 2.05
SqFt Source: Seller
Rentals Allowed: Yes
Min Rental Days: 7
Style: Single Family
Year Built: 2022
Living Apx SqFt: 9704
Total Bedrooms: 8
Full Baths: 8
Half Baths: 3
Total Baths: 11
Remarks & Misc
Remarks – Consumer: A rare dual-offering on coveted Millionaire's Row in Tavernier, this extraordinary oceanfront compound spans over multiple acres across two parcels-delivering an unmatched combination of scale, privacy, and future development flexibility in the Florida Keys. At 88845, a newly constructed 8,200SF estate sets a new standard for modern coastal luxury. Thoughtfully designed for both grand entertaining and private retreat, the residence offers 5 bedrooms, 6 full baths & 2 half baths, complemented by a dedicated office, control room, mudroom, and expansive 3-car garage with climate-controlled workshop. Interior finishes are curated at the highest level, including white diamond marble, teak wood flooring, custom millwork & a vapor fireplace, while a full-home sound system, elevator & advanced mechanical infrastructure provide seamless functionality. The chef's kitchen is equipped with top-tier Wolf, SubZero, & Cove appliances, dual dishwashers, farmhouse sinks, refrigerated drawers, wine storage & custom mahogany countertops-designed to accommodate both everyday living and large-scale entertaining. Outdoor living is equally impressive, anchored by a 120-foot resort-style pool with integrated spa, heating & chilling systems, & full smart control. A fully equipped summer kitchen, cabana bath, & multiple covered terraces create a true waterfront lifestyle experience. With 480 feet of water frontage, the protected basin offers exceptional boating capabilities, including 90 feet of dockage & room to expand, a 20,000lb lift, boat ramp & deep-water access. The adjacent parcel at 88835 provides over 3 acres of additional opportunity featuring a renovated 3-bedroom residence completed in 2022, with a transferable TDR allowing for the development of a substantially larger primary home. The property also includes a buildable lot & natural hammock buffer for added privacy. Together, these two properties present a generational opportunity to own a one of a kind waterfront compound.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
Dock Length: 90
Basin: 1
Boat Lift: 1
Boat Ramp: 1
Boat Slip: 1
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Disposal: 1
Dryer: 1
Freezer: 1
Microwave: 1
More Appliances: 1
Oven: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Wine Cooler: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Waterfront
Oceanfront: 1
Open Water: 1
Waterview
Ocean View: 1
Open Water View: 1
Floor
Marble: 1
Tile: 1
Wood: 1
Interior Features
Built-in Cabinets: 1
Elevator: 1
Entrance Foyer: 1
Security System: 1
Storage: 1
Walk-in Closet(s): 1
Property Condition
New Construction: 1
Specialty Rooms
Laundry Room: 1
Utility Room: 1
Workshop: 1
Building Style
Above Flood: Unknown
Windows/Doors
Impact Rstnce Doors: 1
Impact Rstnce Window: 1
Sliding Glass Doors: 1
Vehicle Storage
Carport: 1
Covered Parking: 1
Garage: 1
Open Parking: 1
Auto Door Opener: 1
Off Street Parking: 1
Trailer Storage: 1
Construction
CBS: 1
Concrete: 1
Land Size
5 Less Than 10 Acres: 1
Furnished
Negotiable: 1
Utilities
Buyer to Verify: 1
Cable Available: 1
FKAA: 1
Porch/Balcony
Open Porch/Balcony: 1
Title
Title Ins - Buyer: 1
Exterior Features
Built-in Grill: 1
Hot Tub: 1
Lighting: 1
Outdoor Kitchen: 1
Sandy Beach: 1
Storage: 1
Pool Info
Concrete: 1
Pre-Wired
Cable: 1
Surround Sound: 1
Roof
Metal Roof: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Oceanfront; Open Water
Waterview: Ocean View; Open Water View
Dockage: Basin; Boat Lift; Boat Ramp; Boat Slip
Property Condition: New Construction
Vehicle Storage: Garage; Carport; Auto Door Opener; Covered Parking; Off Street Parking; Open Parking; Trailer Storage
Furnished: Negotiable
Cooling: Ceiling Fans(s); Central Air
Utilities: Buyer to Verify; Cable Available; FKAA
Interior Features: Built-in Cabinets; Elevator; Entrance Foyer; Security System; Storage; Walk-in Closet(s)
Pre-Wired: Cable; Surround Sound
Specialty Rooms: Laundry Room; Utility Room; Workshop
Appliances: Dishwasher; Disposal; Dryer; Freezer; Microwave; More Appliances; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Exterior Features: Built-in Grill; Hot Tub; Lighting; Outdoor Kitchen; Sandy Beach; Storage
Pool Info: Concrete
Construction: CBS; Concrete
Floor: Marble; Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Land Size: 5 Less Than 10 Acres
Title: Title Ins - Buyer

Listing Office: Serhant Florida LLC - Coconut Grove

Last Updated: May - 08 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.


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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)