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$4,700,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 2,478 Sq. Ft.
  • 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
  • HOA FEE: $21/month
  • HOA FEE FREQ.: Yearly
  • Taxes: $22,353 (2024)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 617501
  • Updated: 5/18/2026
  • Added to Site: 179 day(s) ago

Interior

  • Appliances: Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, Washer
  • Flooring: Tile, Terrazzo, Marble

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4

Additional Information

  • Shared Amenities: Bike Paths
  • Pool: Yes
  • Pool Description: Concrete, In Ground

Exterior

  • Exterior Features: Chickee Hut, Fencing, Outdoor Shower, Privacy Wall/Fence
  • Deck/Patio: Open Porch/Balcony
  • Porch/Patio/Deck: Open Porch/Balcony

Parking

  • Parking Features: Off Street

Location

  • Area: 22 - Lower Matecumbe
  • County: Monroe
  • Subdivision: Safety Harbor (74.0)

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air

Structural Information

  • Architectural Style: Above Flood
  • Construction Status: Updated/Remodeled
  • Construction: CBS
  • Windows/Doors: Impact Rstnce Doors, Impact Rstnce Window, Sliding Glass Doors, Shutters
  • Square Feet: 2,478
  • Sq. Ft. Source: Tax Records
  • Year Built: 1968
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: Open Water View, Bay
  • Lot Size (Acres): 0.26
  • Lot Size (Sq. Ft.): 11,275
  • Lot Size Source: Tax Records
  • Zoning: R1 - Residential Single Family

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Bay Front

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $250
  • Assoc Fee Freq.: Yearly
  • Tax Amount: $22,353.13
  • Tax Year: 2024
  • Terms: 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 OR873-1920DC OR1233-1397 OR13
  • Flood Zone: AE, VE, AE, VE
  • APN: 00391950-000000

Listed by Paradise Florida Keys Real Estate, a Luxury Brand, Judy Rossignol (305) 393-0523 and Paradise Florida Keys Real Estate, a Luxury Brand, Richard Trottnow (305) 842-1151

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Listing agents

— 166 Bayview Dr —

  • Judy Rossignol

    Paradise Florida Keys Real Estate, a Luxury Brand

  • Richard Trottnow

    Paradise Florida Keys Real Estate, a Luxury Brand

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
2024
$22,353
—
$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.

Estimate the Cost for 166 Bayview Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Paradise Florida Keys Real Estate, a Luxury Brand, Judy Rossignol (305) 393-0523 and Paradise Florida Keys Real Estate, a Luxury Brand, Richard Trottnow (305) 842-1151

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166 Bayview Drive, Lower Matecumbe, FL 33036 (MLS# 617501) 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 Lower Matecumbe? You can browse all Lower Matecumbe real estate or contact a Coldwell Banker agent to request more information.

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