166 Bayview Dr

Islamorada, FL 33036

$5,600,000
Price
4
Beds
2,478 Sq. Ft.
$2,260 / Sq. Ft.
2,478
Sq. Ft.
$2,260
per Sq. Ft.
a view of a lake with a big yard
an aerial view of a house with a yard
an aerial view of a house with a yard basket ball court and outdoor seating
a view of a city with lawn chairs
a view of a swimming pool with lawn chairs and plants
an aerial view of residential houses with outdoor space
an aerial view of a house with a garden and lake view
aerial view of a house with swimming pool and large trees
a view of a lake with a table and chairs
a swimming pool with outdoor seating and yard
a front view of a house with a garden
a view of a balcony with furniture
a kitchen with a stove a sink and a refrigerator
a view of a dining room with furniture and a chandelier
a kitchen with stainless steel appliances a refrigerator sink and white cabinets
a kitchen with stainless steel appliances granite countertop a stove a sink and a refrigerator
a living room with furniture a chandelier and a table
a living room with furniture and a lamp
a bedroom with a bed and a painting on the wall
a bedroom with a bed and a flat screen tv
a bathroom with a sink a toilet and shower
a bedroom with a bed and flat screen tv
a bed room with a bed and a television
a bathroom with a sink toilet and shower
a kitchen with stainless steel appliances kitchen island granite countertop a table chairs in it and wooden floors
a dining room with a table chairs and a kitchen view
a bathroom with a sink and a mirror
a living room with furniture and a couch
a bedroom with a bed window and a couch
a bed room with a bed and a window
swimming pool view with a garden space
a swimming pool with a yard
a view of a swimming pool with furniture
a ocean view with seating space
a front view of house with yard and green space
a view of a balcony with lake view
a front view of a house with garden
a view of a house with swimming pool

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,...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.
  1. Listed by Judy Rossignol • Paradise Florida Keys Real Estate, a Luxury Brand
  2. Listed by Richard Trottnow • Paradise Florida Keys Real Estate, a Luxury Brand

Property Details for 166 Bayview Drive

Waterfront
Bay Front
Waterfront
Yes
Zoning
R1 - Residential Single Family
Subdivision
Safety Harbor (74.0)
View
Bay, Water View
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 02/03/2026 12:33 PM

Property Details for 166 Bayview Drive

StatusActive
MLS #617501
Days on Market71
Taxes$22,353 / year
HOA Fees$250 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single
Year Built1968
Lot Size0.26 AC / 11,275 SF
CountyMonroe County

Location

Listing Courtesy of Paradise Florida Keys Real Estate, a Luxury Brand
Add your commute

Building Information for 166 Bayview Drive

Stories2Year Built1968Building Size-Lot Size0.26 AC / 11,275 SF

Payment Calculator

$29,177 per month

30 year fixed, 6.15% Interest

Principal and Interest

$27,293

Property Taxes

$1,863

HOA Dues

$21

The Payment Calculator is for illustrative purposes only.

Property Information for 166 Bayview Drive

Summary
Location and General Information
  • Waterview: Bay/Gulf View, Open Water View
  • Area: 22 - Lower Matecumbe
  • Absolute Longitude: 80.740663
  • Control Depth: 4
  • Listing Board: Florida Keys
  • Side: Bay/Gulf
  • Mile Marker: 74.0
  • Marathon Neighborhood: N/A
  • Neighborhood Feature: Bike Paths
  • Key/Island: Lower Matecumbe
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: Voluntary Home Owners Asc: Yes
  • Association Info: 1st Right of Refusal: No
  • Association Info: Assoc Approval Req: No
  • Fee Includes: None
  • Furnished: Furnished
  • Tax Year: 2024
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.26
  • Parcel #: 00391950-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • Legal: 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
  • MLS Approved: Y
  • SqFt Source: Tax Records
  • Flood Zone: AE,VE,AE,VE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 38
  • Document Count: 0
  • Building Style: Above Flood: Unknown
  • Property Condition: Updated/Remodeled
Utilities
  • Utilities: FKAA, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Species List: No
  • Pool: Yes
  • Handicap Access: No
  • Pool Info: In Ground, Concrete
  • Porch/Balcony: Open Porch/Balcony
Interior and Exterior Features
Interior Features
  • Floor: Tile, Marble, Terrazzo
  • Interior Features: First Floor Entry, Second Floor Entry, Fireplace-Decorative
  • Pre-Wired: Cable
  • Appliances: Washer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Shutters: Clam Shell
  • Dockage: Dock Length: 40
  • Construction: CBS
  • Dockage: Davits
  • Exterior Features: Chickee Hut, Privacy Wall/Fence, Outdoor Shower, Fencing
  • Windows/Doors: Sliding Glass Doors, Impact Rstnce Window, Impact Rstnce Doors

Property History for 166 Bayview Drive

DateEvent & SourcePriceAppreciation
Nov 29, 2025

Listed (Active)

MiamiRE #A11927254

$5,600,000—
Nov 29, 2025

Listed (Active)

FKMLS #617501

$5,600,000—
Nov 8, 2013

Expired

FKMLS #556306

—
Nov 8, 2011

Listed (Active)

FKMLS #556306

$1,249,000—
Nov 7, 2011

Temp Off Market

FKMLS #550191

—
Nov 5, 2009

Listed (Active)

FKMLS #550191

$2,399,999—
Nov 18, 2004

Sold (Public Record)

Public Record #147864012

$2,225,000—
Nov 5, 2004

Sold

FKMLS #521781

$2,225,000—
Oct 1, 2004

Pending

FKMLS #521781

—
May 4, 2004

Listed (Active)

FKMLS #521781

$2,400,000—
DateEvent & SourcePrice
11/29/2025

Listed (Active)

MiamiRE #A11927254

$5,600,000
11/29/2025

Listed (Active)

FKMLS #617501

$5,600,000
11/08/2013

Expired

FKMLS #556306

—
11/08/2011

Listed (Active)

FKMLS #556306

$1,249,000
11/07/2011

Temp Off Market

FKMLS #550191

—
11/05/2009

Listed (Active)

FKMLS #550191

$2,399,999
11/18/2004

Sold (Public Record)

Public Record #147864012

$2,225,000
11/05/2004

Sold

FKMLS #521781

$2,225,000
10/01/2004

Pending

FKMLS #521781

—
05/04/2004

Listed (Active)

FKMLS #521781

$2,400,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 166 Bayview Drive

Taxable ValueLand$2,559,425Additions$371,304Total$2,930,729
Tax Record2024$22,353 ($1,863 / month)
Home Facts
Beds3Baths3Total Finished SqFt2,184 SqFtAbove Grade Finished SqFt2,184 SqFtStories2Lot Size11,033 SqFtStyleSingle Family ResidenceYear Built1968Year Renovated1995CountyMONROEAPN00391950-000000Fireplace TypeHas Fireplace

Schools near 166 Bayview Drive

This home is within Monroe.
Rating
School
Type
Grades
Distance
Plantation Key School
Public - PK to 8
Coral Shores High School
Public - 9 to 12
Treasure Village Montessori Charter School
Charter - PK to 8
Upper Keys Academic Connections for Excellence
Public - 6 to 12
Rating
School
Distance
Plantation Key School
PublicPK to 8

Coral Shores High School
Public9 to 12

Treasure Village Montessori Charter School
CharterPK to 8

Upper Keys Academic Connections for Excellence
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 166 Bayview Drive, Islamorada, FL 33036

166 Bayview Drive is a single family home for sale in Islamorada, FL 33036. This property was listed for sale on November 29, 2025 by Paradise Florida Keys Real Estate, a Luxury Brand, it's currently listed at $5,600,000. It has been on the market for a total of 71 days and was last sold on November 18, 2004. This listing's school district is Monroe. Nearby schools include Plantation Key School, Coral Shores High School and Treasure Village Montessori Charter School. 166 Bayview Drive is a 4-bed, 4-bath, 2,478 sqft single family home built in 1968.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Paradise Florida Keys Real Estate, a Luxury Brand

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.