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$4,700,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • Updated 9 days ago
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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.

Full Property Details for 166 Bayview Dr

General

  • Price: $4,700,000
  • Taxes: $22,931 (2025)
  • Status: Pending
  • Type: Single Family
  • Source: Greater_Miami
  • MLS ID: A11927254
  • Updated: 7/16/2026
  • Added to Site: 239 day(s) ago

Interior

  • Interior Features: First Floor Entry, Second Floor Entry, Other, Utility Room/Laundry
  • Fireplace: Yes
  • Fireplace(s): Decorative
  • Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Electric Range, Gas Range, Washer
  • Flooring: Ceramic Floor, Marble, Terrazzo

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4
  • Bedroom Features: At Least 1 Bedroom Ground Level, Entry Level, Primary Bath Shower, Primary Bedroom Upstairs

Other Rooms

  • Living Room: Other, Utility Room/Laundr Sq. Ft.
  • Laundry: Utility Room/Laundry

Additional Information

  • Pool: Yes
  • Pool Description: In Ground, Heated, 20 X

Exterior

  • Exterior Features: Barbecue, Lighting, Outdoor Shower
  • Deck/Patio: Deck

Parking

  • Parking Features: Driveway, Guest, Other, Limited # Of Vehicle

Location

  • Area: Safety Harbor
  • County: Monroe County
  • Subdivision: Safety Harbor
  • Building Name: Safety Harbor
  • Direction Faces: East

Community

  • Community Name: Safety Harbor

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Ceiling Fan(s), Central Air
  • Heating Type: Central, Electric, Heat Pump/Reverse Cycle

Utilities

  • Sewer: Public Sewer
  • Water: Municipal Water

Structural Information

  • Architectural Style: Detached, Two Story
  • Structure Type: House
  • Detached/Attached: Detached
  • Construction: Concrete Block Construction, CBS Construction
  • Roof: Other
  • Windows: Hurricane Shutters
  • Doors: High Impact Doors
  • Year Built: 1968

Lot Features

  • Property View: Bay, Water
  • Frontage: Bay
  • Frontage Feet: 200
  • Lot Features: Less Than 1/4 Acre Lot
  • Zoning: 1465
  • Fencing (Description): Fenced

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Ocean Access

Financial Considerations

  • Tax Amount: $22,931
  • Tax Year: 2025
  • Terms: All Cash, Conventional

Disclosures and Reports

  • Legal Description: SAFETY HARBOR SEC-1 PB3-69 LOWER MATECUMBE KEY LOT 6 BK 7 AND ADJ FILLED BAY BTM OR291-526
  • Restrictions: Ok To Lease
  • Inclusions: Deeded Dock, Private Dock, Dock Owned/Included
  • Property ID: 3919500000

Listed by Paradise Florida Keys Real Est

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— 166 Bayview Dr —

  • Paradise Florida Keys Real Est

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 166 Bayview Dr

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Plantation Key School
100 Lake Road, Tavernier, FL 33070
PK-815.6 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1268.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 166 Bayview Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/18/2026
Price Reduced
$4,700,000
-16.07%
MLS
11/29/2025
Listed
$5,600,000
151.69%
MLS
11/18/2004
Sold
$2,225,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 166 Bayview Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$23,887
7%
$2,930,729
1%
2024
$22,353
4%
$2,911,783
2%
2023
$21,417
29%
$2,844,709
75%
2021
$16,617
-8%
$1,623,313
-19%
2022
$18,023
8%
$1,993,008
12%
2021
$16,617
3%
$1,783,238
24%
2019
$16,086
9%
$1,440,784
10%
2018
$14,805
11%
$1,309,804
-10%
2017
$13,294
1%
$1,452,653
3%
2016
$13,145
14%
$1,404,450
43%
2015
$11,488
15%
$984,076
10%
2014
$10,005
4%
$894,615
5%
2013
$9,657
—
$849,533
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Paradise Florida Keys Real Est

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166 Bayview Drive, Islamorada, FL 33036 (MLS# A11927254) is a Single Family property with 4 bedrooms and 4 full bathrooms. 166 Bayview Drive is currently listed for $4,700,000 and was received on November 29, 2025. Want to learn more about 166 Bayview Drive? Do you have questions about finding other Single Family real estate for sale in Islamorada? You can browse all Islamorada real estate or contact a Coldwell Banker agent to request more information.

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