442 Palm Dr, Islamorada, FL 33036
Property image
Property image
OFF MARKET

$4,017,300

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,058 sqft (on 0.26 acres)

442 Palm Dr, Islamorada, FL 33036

Est. Refi. Payment $24,180/mo*
Refinance Your Home
Currently Off Market - Sold Sep 16, 2025 for $3,900,000

Home Value

Trulia Estimate
$4.02M
Since last month
Increased$60K (+1.5%)
Since last year
Increased$119K (+3%)
Since last sale
Increased$120K (+3.1%)
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 +155% in the last 10 years
MonthEstimated value
2026
September 2026$4.02M
August 2026$3.96M
July 2026$3.93M
June 2026$3.89M
May 2026$3.81M
April 2026$3.85M
March 2026$3.84M
February 2026$3.87M
January 2026$3.87M
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
439 Palm Dr, Islamorada, FL
0.03
Single-Family Home
$1,950,000
06/12/26
4
3
2,294
182 Bayview Dr, Islamorada, FL
0.17
Single-Family Home
$3,950,000
03/06/26
4
3
3,434
166 Bayview Dr, Islamorada, FL
0.25
Single-Family Home
$4,200,000
09/02/26
4
4
2,478
133 Sunset Dr, Islamorada, FL
0.57
Single-Family Home
$3,003,000
06/29/26
4
3
2,519
430 Palm Dr, Lower Matecumbe Key, FL
0.05
Single-Family Home
$5,550,000
09/10/26
5
6
5,153
145 Venetian Dr, Lower Matecumbe Key, FL
0.37
Single-Family Home
$3,250,000
08/06/26
4
3.5
3,182
193 Nautilus Dr, Islamorada, FL
0.39
Single-Family Home
$2,200,000
03/16/26
3
3
1,911
141 El Capitan Dr, Islamorada, FL
0.64
Single-Family Home
$2,500,000
03/13/26
4
3
2,098
172 Venetian Dr, Islamorada, FL
0.30
Single-Family Home
$3,525,000
01/28/26
5
5.5
4,131
230 Biscayne Blvd, Islamorada, FL
0.78
Single-Family Home
$3,205,000
01/22/26
5
3
2,425

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
430 Palm Dr, Lower Matecumbe Key, FL 33036
0.05
$5,550,000
5
6
5,153
Recently Sold
439 Palm Dr, Islamorada, FL 33036
0.03
$1,950,000
4
3
2,294
Recently Sold
445 Palm Dr, Islamorada, FL 33036
0.06
-
-
-
-
Off Market
Buttonwood Ln, Islamorada, FL 33036
0.16
-
-
-
-
Off Market
194 Buttonwood Ln, Islamorada, FL 33036
0.18
$6,150,000
6
7
5,100
For Sale
182 Bayview Dr, Islamorada, FL 33036
0.17
$3,950,000
4
3
3,434
Recently Sold
400 Palm Dr, Islamorada, FL 33036
0.21
$5,762,400
6
7.5
4,700
Off Market
166 Bayview Dr, Islamorada, FL 33036
0.25
$4,200,000
4
4
2,478
Recently Sold
172 Venetian Dr, Islamorada, FL 33036
0.30
$3,525,000
5
5.5
4,131
Recently Sold
162 Bayview Dr, Islamorada, FL 33036
0.26
$7,950,000
8
9
5,392
For Sale
190 Venetian Dr, Islamorada, FL 33036
0.31
$2,154,800
3
3
1,200
Off Market

Local Information

  • Map ViewExplore the area around 442 Palm Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1977
0.26 acre lot
2,058 sqft
$1,952/sqft

About this House

What's unique:Separate guest suiteDeep-water dockagePrivate bedroomStunning turquoise water viewsWaterfront homeBreathtaking views
ACTIVE POOL PERMIT! A truly spectacular waterfront home with 150 feet of prime bay frontage, offering breathtaking views of some of the clearest waters in the Florida Keys. This property has undergone a complete top-to-bottom renovation with exceptional attention to detail. Solid concrete bunker with a concrete roof and impact windows & doors. Boaters will appreciate the deep-water dockage, accommodating nearly any vessel, with easy ocean access through Channel 5.

The main living area upstairs features three bedrooms, two bathrooms, and a beautifully designed kitchen with high-end appliances—all framed by stunning turquoise water views from nearly every room. Downstairs, a separate guest suite includes a private bedroom, bathroom, living room, and kitchen, perfect for visitors or additional living space.

A pool permit is already in place, or you can take a refreshing swim right in the bay. This home is truly one-of-a-kind—don't miss the chance to own a special piece of paradise!
442 Palm Dr, Islamorada, FL 33036 is a 4 bedroom, 3 bathroom, 2,058 sqft single-family home built in 1977. It last sold for $3,900,000 on Sep 16, 2025 (8% below the $4,250,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,017,300.
Last check for updates: about 16 hours ago
Listed by AJ Vetter, (305) 304-8841
Palm House Real Estate
Drew Moret, (305) 393-3331
Palm House Real Estate
Bought with: Alexander Pinero, (305) 450-4541, Pine River Realty, LLC
Source: FLKMLS, MLS#614036

Home Details for 442 Palm Dr

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2058 Square Feet
Appliances & Utilities
Appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Stainless Steel Appliance(s)DishwasherDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Has CoolingAir Conditioning: Central Air,Ductless
Windows, Doors, Floors & Walls
Flooring: Tile
Levels, Entrance, & Accessibility
Floors: Tile
View
No View

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/BalconyFencing: FencedNo Private Pool
Parking & Garage
No Attached Garage
Frontage
WaterfrontOn Waterfront

Property Information

Year Built
Year Built: 1977
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: CBSNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00391220000000

Price & Status

Price
List Price: $4,250,000

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 2058 Square Feet

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 0.26 acres

Miscellaneous

Mls Number: 614036

Price and Tax history

DateEventPrice
Sep 16, 2025
Source: FLKMLS #614036
Sold
$3,900,000
Sep 12, 2025
Source: FLKMLS #614036
Pending
$4,250,000
Sep 8, 2025
Source: FLKMLS #614036
Contingent
$4,250,000
Aug 11, 2025
Source: FLKMLS #614036
PriceChange
$4,250,000
Price decreased by 1%
Jul 1, 2025
Source: Key West AOR #614036
PriceChange
$4,275,000
Price decreased by 3%

Market trends in Islamorada

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
149
11MoM

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 442 Palm Dr

  • What is 442 Palm Dr estimated to be worth?
    Trulia's estimated value for 442 Palm Dr in Islamorada, FL is $4,017,300.
  • What is the price history for 442 Palm Dr?
    442 Palm Dr in Islamorada, FL last sold for $3,900,000 in September 2025.
  • Is Islamorada a buyer's or seller's market?
    Islamorada is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Islamorada?
    Residents describe Islamorada, FL as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Islamorada, FL.
  • Does 442 Palm Dr have air conditioning?
    Yes, 442 Palm Dr in Islamorada, FL has air conditioning.
  • Does 442 Palm Dr have laundry facilities?
    Yes, 442 Palm Dr in Islamorada, FL has in-unit laundry.

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Off Market Homes Near 442 Palm Dr

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