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$4,200,000
166 Bayview Drive
Lower Matecumbe, FL 33036
MLS# 617501
Status: Closed
4 beds  |  4 baths  |  2478 sqft


Looking West
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Looking West Osprey's View Corner Lot Hurricane Hole Bayfront!! Lower Matecumbe Safety Harbor Privacy Fencing Aerial View Open Water Views Streetside Looking West Dining with a View Upstairs Kitchen Upstairs Kitchen Prep with a view Open Living area Views everywhere Upstairs Primary Bedroom More views Upstairs Bath in Primary Bedroom Cozy and Comfortable Upstairs Bedroom #2 Bathroom #2 upstairs Downstairs Kitchen Downstairs Breakfast Table Bathroom #3 Downstairs @nd Bedroom Downstairs 4 total bedrooms Downstairs Primary Waiting for the Green Flash Endless Views Tiki by the Bay Dock with lift Lounge Lizards Welcome Sunsets on the Bay Evening Magic ISLAMORADA!!

Property Description
Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene. The home enjoys unobstructed water views and nightly sunsets that paint the sky in brilliant hues. A Tiki at the water's edge provides a perfect perch for morning coffee or evening cocktails, while mature landscaping adds privacy and tropical charm. Boaters will appreciate the deep-water dockage with davits, ideal for quick access to open water. The 2,478-square-foot residence features 4 bedrooms and 4 bathrooms, with tile flooring throughout and expansive windows that frame the bay. The open-concept living and dining areas flow into a well-appointed kitchen. The primary suite offers direct water views and private outdoor access. Outdoor living is elevated with a spacious pool and deck area, balcony, and brick paver walkways. The white picket fencing and lush landscaping complete the coastal aesthetic. Additional features include CBS construction, off-street parking, FKAA water service, septic system, and low HOA fees. Pets are welcome. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, 166 Bayview Drive delivers unmatched location, views, and lifestyle in the Florida Keys.

Details
Maps
Contract Information
Current Price: $4,200,000
Listing Date: 2025-11-29
Listing Board: Florida Keys
Leased Price Monthly: $4,200,000
As is Rght to Inspct: Yes
Species List: No
Location, Tax & Legal
Street #: 166
Street Name: Bayview
Street Suffix: Drive
Key/Island: Lower Matecumbe
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Safety Harbor (74.0)
Area: 22 - Lower Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 4
Pool: Yes
Year Built: 1968
Lot SqFt: 11275
Lot Sqft Source: Tax Records
Acres: 0.26
Living Apx SqFt: 2478
SqFt Source: Tax Records
Total Bedrooms: 4
Full Baths: 4
Total Baths: 4
Rentals Allowed: With Restrictions
Association Info
Mandatory Home Owners Asc: No
Voluntary Home Owners Asc: Yes
1st Right of Refusal: No
Assoc Approval Req: No
Association Fee $: 250
Assoc/Mnt Fee Per: Yearly
Dockage
Dock Length: 40
Building Style
Above Flood: Unknown
# Stories: 2 Stories
Status Change Info
Under Contract Date: 2026-07-14
Leased Date: 2026-09-02
Leased Price Monthly: $4,200,000
Status: Closed
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front
Waterview: Bay/Gulf View; Open Water View
Dockage: Davits
Property Condition: Updated/Remodeled
Vehicle Storage: Off Street Parking
Furnished: Furnished
Cooling: Central Air
Utilities: Buyer to Verify; FKAA; Municipal Sewer
Pre-Wired: Cable
Appliances: Dishwasher; Dryer; Microwave; Oven; Range; Refrigerator; Washer
Exterior Features: Chickee Hut; Fencing; Outdoor Shower; Privacy Wall/Fence
Pool Info: In Ground; Concrete
Construction: CBS
Shutters: Clam Shell
Floor: Marble; Terrazzo; Tile
Pets: Pets Allowed
Neighborhood Feature: Bike Paths
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional

Listing Office: Paradise Florida Keys Real Estate, a Luxury Brand

Last Updated: September - 03 - 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.