166 Bayview Dr, Islamorada, FL 33036
Property image
Property image
SOLD
SEP 2, 2026

$4,197,600

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 2,478 sqft (on 0.26 acres)

166 Bayview Dr, Islamorada, FL 33036

Est. Refi. Payment $24,746/mo*
Refinance Your Home
Currently Off Market - Sold Sep 2, 2026 for $4,200,000 (11% below list price)

Home Value

Trulia Estimate
$4.2M
Since last month
Decreased$22K (-0.5%)
Since last year
Increased$387K (+10.2%)
Since last sale
Decreased$10K (-0.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +104% in the last 10 years
MonthEstimated value
2026
August 2026$4.19M
August 2026$4.19M
July 2026$4.21M
June 2026$4.2M
March 2026$5.01M
February 2026$5M
January 2026$5M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
182 Bayview Dr, Islamorada, FL
0.08
Single-Family Home
$3,950,000
03/06/26
4
3
3,434
442 Palm Dr, Islamorada, FL
0.25
Single-Family Home
$3,900,000
09/16/25
4
3
2,058
439 Palm Dr, Islamorada, FL
0.22
Single-Family Home
$1,950,000
06/12/26
4
3
2,294
133 Sunset Dr, Islamorada, FL
0.56
Single-Family Home
$3,003,000
06/29/26
4
3
2,519
145 Venetian Dr, Lower Matecumbe Key, FL
0.51
Single-Family Home
$3,250,000
08/06/26
4
3.5
3,182
172 Venetian Dr, Islamorada, FL
0.49
Single-Family Home
$3,525,000
01/28/26
5
5.5
4,131
91 Iroquois Dr, Islamorada, FL
0.42
Single-Family Home
$7,600,000
06/26/26
4
5
4,048
72 W Plaza Granada, Islamorada, FL
0.75
Single-Family Home
$2,300,000
02/27/26
4
3.5
2,937
193 Nautilus Dr, Islamorada, FL
0.57
Single-Family Home
$2,200,000
03/16/26
3
3
1,911

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
162 Bayview Dr, Islamorada, FL 33036
0.02
$7,950,000
8
9
5,392
For Sale
257 Tollgate Blvd, Islamorada, FL 33036
0.07
$6,619,600
4
4.5
3,907
Off Market
234 Tollgate Blvd, Islamorada, FL 33036
0.10
$3,133,800
2
2
-
Off Market
237 Toll Gate Blvd, Islamorada, FL 33036
0.11
$2,020,000
2
2
-
Off Market
182 Bayview Dr, Islamorada, FL 33036
0.08
$3,950,000
4
3
3,434
Recently Sold
317 Toll Gate Shores Dr, Islamorada, FL 33036
0.13
$950,900
2
2
1,008
Off Market
186 & 165 Bayview Dr, Islamorada, FL 33036
0.10
$10,900,000
6
4.5
4,394
For Sale
321 Tollgate Shores Dr, Islamorada, FL 33036
0.16
$1,062,000
2
2
1,532
Recently Sold
194 Buttonwood Ln, Islamorada, FL 33036
0.13
$6,150,000
6
7
5,100
For Sale
322 Toll Gate Shores Dr, Islamorada, FL 33036
0.18
$5,454,500
5
5
3,995
Off Market
205 Toll Gate Blvd, Islamorada, FL 33036
0.19
$2,220,400
2
2
-
Off Market

Local Information

  • Map ViewExplore the area around 166 Bayview Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1968
0.26 acre lot
2,478 sqft
$1,695/sqft
HOA $21/mo

About this House

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.
166 Bayview Dr, Islamorada, FL 33036 is a 4 bedroom, 4 bathroom, 2,478 sqft single-family home built in 1968. It last sold for $4,200,000 on Sep 2, 2026 (11% below the $4,700,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,197,600, with a rent estimate of $7,754/month.
Last check for updates: about 7 hours ago
Listed by Judy Rossignol, (305) 393-0523
Paradise Florida Keys Real Estate, a Luxury Brand
Richard Trottnow, (305) 842-1151
Paradise Florida Keys Real Estate, a Luxury Brand
Bought with: Drew Moret, (305) 393-3331, Palm House Real Estate
Source: FLKMLS, MLS#617501

Home Details for 166 Bayview Dr

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 2478 Square Feet
Appliances & Utilities
Appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, MicrowaveDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air
Windows, Doors, Floors & Walls
Flooring: Tile, Terrazzo, Marble
Levels, Entrance, & Accessibility
Floors: Tile, Terrazzo, Marble
View
No View

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/BalconyFencing: Fenced, PrivacyExterior: Chickee Hut, Outdoor ShowerHas a Private Pool
Parking & Garage
No Attached Garage
Pool
Pool: In Ground, ConcretePool
Frontage
WaterfrontOn Waterfront

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: CBSNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00391950000000

Price & Status

Price
List Price: $4,700,000Price Per Sqft: $1,695/sqft

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Lower MatecumbeCommunity: Safety Harbor (74.0)

Building

Building Area
Building Area: 2478 Square Feet

Community

Community Features: Bike Paths

HOA

HOA Fee Includes: NoneNo HOAHOA Fee: $250/Annually

Lot Information

Lot Area: 0.26 acres

Offer

Listing Terms: Cash, Conventional

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 617501

Additional Information

Bike Paths

Price and Tax history

DateEventPrice
Sep 2, 2026
Source: FLKMLS #617501
Sold
$4,200,000
Jul 16, 2026
Source: FLKMLS #617501
Pending
$4,700,000
May 18, 2026
Source: Key West AOR #617501
PriceChange
$4,700,000
Price decreased by 16%
Nov 29, 2025
Source: FLKMLS #617501
Listed For Sale
$5,600,000
Oct 26, 2013
Source: Agent Provided
ListingRemoved
$1,249,000

Market trends in Islamorada

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.09M
$8.17KMoM
Sale-to-List Price
—
Price per sq ft
$724
$14MoM
Available listings
159
2MoM

Around this home

What Locals Say about Islamorada

At least 24 Trulia users voted on each feature.

  • 88 % Say people would walk alone at night

  • 88 % Say parking is easy

  • 84 % Say it's dog friendly

  • 83 % Say yards are well-kept

  • 79 % Say car is needed

  • 72 % Say kids play outside

  • 70 % Say it's quiet

  • 67 % Say it's walkable to restaurants

  • 58 % Say they plan to stay for at least 5 years

  • 56 % Say there's holiday spirit

  • 55 % Say neighbors are friendly

  • 53 % Say there's wildlife

  • 44 % Say there are community events

  • 41 % Say it's walkable to grocery stores

  • 39 % Say streets are well-lit

  • 23 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • John Hermansen
    "Fishing tournaments and HOA lunches are nice. The marina is a great community and everyone on the airstrip are very kind. Great place for kids and dogs. "
    1
    Flag
  • Jnmarcil
    "The area is awesome. Safe, clean , everyone knows everyone and keep an eye out for our neighbors best place to live. "
    0
    Flag
  • Trulia User
    "Neighborhood feels safe and secure. I love the area. Live right near the Montessori school. Beware because there are sometimes fast drivers. "
    0
    Flag
  • Trulia User
    "Lots of grass to play in. Easy living in the Keys. Lots of places to run you dogs. Pebbles & Bambam enjoy it. "
    0
    Flag
  • Fabelomaribel
    "I've lived in this neighborhood for a while and the people are very nice I love my neighbor's the schools are closed by"
    1
    Flag
  • Cinnapep
    "Beautiful area with friendly people. Clean neighborhood and low crime rate. Very walkable with great galleries and restaurants. "
    0
    Flag
  • Jessica G.
    "I’ve lived here for almost 2 years now and i live net the boat ramp and everyone is very nice and the schools are close as they can be"
    0
    Flag
  • Jessica
    "It is near the high school and close to Winn Dixie along with close by gas stations .................."
    0
    Flag
  • Amie B.
    "we've lived her for 1 year and lovve it, beautiful ocean views and multi million dollar homes atl around. "
    0
    Flag
  • Lynne G.
    "Love it here in Safety Harbor. Everything about this home and neighborhood is wonderful. Kind neigbors, lovely views, best of Islamorada communities. Plenty to do if you are looking for it and plenty of peace & privacy at the same time. "
    0
    Flag
  • Lucytwo259
    "This is one of the best areas in Islamorada, It is a beautiful ocean-side location with easy ocean access. It is far enough away from the hustle and noise of the commercial area but not so far that it is inconvenient."
    0
    Flag
  • Kathy D.
    "Coral Harbour Club is located in the heart of Islamorada near shopping and dining."
    0
    Flag
  • Interested I. A.
    "Islamorada is a wonderful community with lots of things to do for all ages and lifestyles. Fishing, bird watching, hiking, swimming, snorkeling, kayaking, biking, running, great nightlife and restaurants. All around fun and relaxation!"
    0
    Flag

LGBTQ Local Legal Protections

MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.

Frequently asked questions about 166 Bayview Dr

  • What is 166 Bayview Dr estimated to be worth?
    Trulia's estimated value for 166 Bayview Dr in Islamorada, FL is $4,197,600.
  • What is the price history for 166 Bayview Dr?
    166 Bayview Dr in Islamorada, FL last sold for $4,200,000 in September 2026.
  • Is Islamorada a buyer's or seller's market?
    Islamorada is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Islamorada?
    The median sale price in Islamorada is $1.09M. That is up $8.17K from the prior month.
  • Does 166 Bayview Dr have air conditioning?
    Yes, 166 Bayview Dr in Islamorada, FL has air conditioning.
  • Does 166 Bayview Dr have a pool?
    Yes, 166 Bayview Dr in Islamorada, FL has a pool.

Explore by feature - Pet Friendly

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