257 Sunset Dr, Islamorada, FL 33036
Property image
Property image
OFF MARKET

$2,816,200

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,674 sqft

257 Sunset Dr, Islamorada, FL 33036

Est. Refi. Payment $16,507/mo*
Refinance Your Home
Currently Off Market - Sold Oct 26, 2020 for $1,650,000

Home Value

Trulia Estimate
$2.82M
Since last month
Increased$16K (+0.6%)
Since last year
Increased$292K (+11.5%)
Since last sale
Increased$1M (+70.7%)
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 +130% in the last 10 years
MonthEstimated value
2026
August 2026$2.82M
August 2026$2.82M
July 2026$2.8M
June 2026$2.72M
May 2026$2.71M
April 2026$2.68M
March 2026$2.65M
February 2026$2.63M
January 2026$2.6M
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
140 Iroquois Dr, Islamorada, FL
0.19
Single-Family Home
$1,490,000
08/11/26
3
3
1,384
321 Tollgate Shores Dr, Islamorada, FL
0.35
Single-Family Home
$1,062,000
08/31/26
2
2
1,532
100 Iroquois Dr #5, Lower Matecumbe Key, FL
0.16
Single-Family Home
$960,000
04/21/26
3
3
1,710
189 Gulfview Dr, Islamorada, FL
0.76
Single-Family Home
$2,200,000
01/12/26
3
2
2,010
64 W Plaza Del Sol, Lower Matecumbe Key, FL
0.86
Single-Family Home
$1,960,000
12/08/25
3
2
1,560
193 Nautilus Dr, Islamorada, FL
0.74
Single-Family Home
$2,200,000
03/16/26
3
3
1,911
133 Sunset Dr, Islamorada, FL
0.35
Single-Family Home
$3,003,000
06/29/26
4
3
2,519
213 Nautilus Dr, Islamorada, FL
0.79
Single-Family Home
$1,300,000
04/01/26
2
2
1,530
439 Palm Dr, Islamorada, FL
0.63
Single-Family Home
$1,950,000
06/12/26
4
3
2,294
104 W Plaza Granada, Islamorada, FL
0.89
Single-Family Home
$2,241,000
12/22/25
3
2
2,200

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
91 Iroquois Dr, Islamorada, FL 33036
0.09
$7,600,000
4
5
4,048
Recently Sold
119 Iroquois Dr, Islamorada, FL 33036
0.12
$2,039,700
4
2
1,857
Off Market
100 Iroquois Dr #3, Islamorada, FL 33036
0.14
$846,000
3
3
1,440
Off Market
100 Iroquois Dr #5, Lower Matecumbe Key, FL 33036
0.16
$999,999
3
3
1,710
For Sale
149 Iroquois Dr, Islamorada, FL 33036
0.17
$825,000
-
-
-
For Sale
140 Iroquois Dr, Islamorada, FL 33036
0.19
$1,490,000
3
3
1,384
Recently Sold
159 Iroquois Dr, Islamorada, FL 33036
0.22
$1,675,000
3
3
2,034
For Sale
158 Iroquois Dr, Islamorada, FL 33036
0.23
$1,392,000
3
3
1,920
Off Market
Iroquois Dr, Islamorada, FL 33036
0.24
-
-
-
-
Off Market
176 Iroquois Dr, Islamorada, FL 33036
0.28
$1,361,000
2
2
960
Off Market
205 Toll Gate Blvd, Islamorada, FL 33036
0.31
$2,220,400
2
2
-
Off Market
322 Toll Gate Shores Dr, Islamorada, FL 33036
0.34
$5,454,500
5
5
3,995
Off Market

Local Information

  • Map ViewExplore the area around 257 Sunset Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1976
1,674 sqft
$1,682/sqft

About this House

One of the best values in all of the Florida Keys in a much sought-after location. Being sold by the home's second owner. The home has been completely upgraded and is ready to enjoy. Sit on the deck and watch the fish swim by, or wade out and hook up. This is a true beach house, with endless ocean views, silky sand beach, and clear Atlantic waters to enjoy. This home has the infrastructure to add a third floor for additional space and views. Upstairs there is one bedroom and one bathroom with a large laundry closet space. Downstairs is comprised of two bedrooms and one bathroom. Both levels offer large porches overlooking the Atlantic Ocean and the property's beautiful beach with views of the sunrise and sunset. Potential for third floor.
257 Sunset Dr, Islamorada, FL 33036 is a 3 bedroom, 2 bathroom, 1,674 sqft single-family home built in 1976. It last sold for $1,650,000 on Oct 26, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,816,200, with a rent estimate of $5,367/month.

Home Details for 257 Sunset Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Types of Rooms: Walk In Closet
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Tile

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: StuccoFoundation Type: PilingPatioPorch

Property Information

Year Built
Year Built: 1976Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 7501 sqft

Price and Tax history

DateEventPrice
Oct 26, 2020
Source: FLKMLS #584078
Sold
$1,650,000
Aug 12, 2020
Source: Agent Provided
PriceChange
$1,700,000
Price decreased by 6%
Jul 27, 2020
Source: Agent Provided
PriceChange
$1,799,999
Price decreased by 10%
Jul 23, 2019
Source: Agent Provided
PriceChange
$1,990,000
Price decreased by 12%
Aug 9, 2018
Source: Agent Provided
PriceChange
$2,249,000
Price decreased by 10%

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

Frequently asked questions about 257 Sunset Dr

  • What is 257 Sunset Dr estimated to be worth?
    Trulia's estimated value for 257 Sunset Dr in Islamorada, FL is $2,816,200.
  • What is the price history for 257 Sunset Dr?
    257 Sunset Dr in Islamorada, FL last sold for $1,650,000 in October 2020.
  • 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 257 Sunset Dr have air conditioning?
    Yes, 257 Sunset Dr in Islamorada, FL has air conditioning.
  • Does 257 Sunset Dr have laundry facilities?
    Yes, 257 Sunset Dr in Islamorada, FL has in-unit laundry.

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