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

249 Sunset Dr
Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 2,070 sqft (on 0.57 acres)

$5,191,600

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $29,957/mo*
Refinance Your Home

$5,191,600

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $29,957/mo*
Refinance Your Home
3 Beds
3 Baths
2,070 sqft
(on 0.57 acres)

Home Value

Trulia Estimate
$5.19M
Since last month
Decreased$40K (-0.8%)
Since last year
Increased$536K (+11.5%)
Since last sale
Increased$3M (+147.2%)
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 +188% in the last 10 years
MonthEstimated value
2026
August 2026$5.19M
July 2026$5.23M
June 2026$4.98M
May 2026$5.01M
April 2026$4.92M
March 2026$4.93M
February 2026$4.88M
January 2026$4.87M
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
140 Iroquois Dr, Islamorada, FL
0.16
Single-Family Home
$1,490,000
08/11/26
3
3
1,384
133 Sunset Dr, Islamorada, FL
0.34
Single-Family Home
$3,003,000
06/29/26
4
3
2,519
91 Iroquois Dr, Islamorada, FL
0.06
Single-Family Home
$7,600,000
06/26/26
4
5
4,048
100 Iroquois Dr #5, Lower Matecumbe Key, FL
0.12
Single-Family Home
$960,000
04/21/26
4
3
1,710
439 Palm Dr, Islamorada, FL
0.60
Single-Family Home
$1,950,000
06/12/26
4
3
2,294
193 Nautilus Dr, Islamorada, FL
0.72
Single-Family Home
$2,200,000
03/16/26
3
3
1,911
442 Palm Dr, Islamorada, FL
0.62
Single-Family Home
$3,900,000
09/16/25
4
3
2,058
169 Venetian Dr, Islamorada, FL
0.67
Single-Family Home
$1,303,500
09/03/25
3
3
2,150
182 Bayview Dr, Islamorada, FL
0.52
Single-Family Home
$3,950,000
03/06/26
4
3
3,434
189 Gulfview Dr, Islamorada, FL
0.74
Single-Family Home
$2,200,000
01/12/26
3
2
2,010

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
119 Iroquois Dr, Islamorada, FL 33036
0.10
$2,036,100
4
2
1,857
Off Market
91 Iroquois Dr, Islamorada, FL 33036
0.06
$7,600,000
4
5
4,048
Recently Sold
100 Iroquois Dr #3, Islamorada, FL 33036
0.11
$848,400
3
3
1,440
Off Market
100 Iroquois Dr #5, Lower Matecumbe Key, FL 33036
0.12
$960,000
4
3
1,710
Recently Sold
149 Iroquois Dr, Islamorada, FL 33036
0.14
$825,000
-
-
-
For Sale
140 Iroquois Dr, Islamorada, FL 33036
0.16
$1,490,000
3
3
1,384
Recently Sold
159 Iroquois Dr, Islamorada, FL 33036
0.21
$1,675,000
3
3
2,034
For Sale
158 Iroquois Dr, Islamorada, FL 33036
0.21
$1,359,100
3
3
1,920
Off Market
Iroquois Dr, Islamorada, FL 33036
0.23
-
-
-
-
Off Market
176 Iroquois Dr, Islamorada, FL 33036
0.26
$1,331,800
2
2
960
Off Market
205 Toll Gate Blvd, Islamorada, FL 33036
0.28
$2,226,300
2
2
-
Off Market
133 Sunset Dr, Islamorada, FL 33036
0.34
$3,003,000
4
3
2,519
Recently Sold

Local Information

  • Map ViewExplore the area around 249 Sunset Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1967
Lot Size
0.57 acres
Living Area
2,070 sqft
Price/Sqft
$2,508
Parking
Garage

About this House

THE MOST BEAUTIFUL BEACH IN THE KEYS! This outstanding property is located on one of the only true white sandy beaches in the Fl, Keys, offering a 3br/3ba CBS home directly on the ocean with outstanding ocean views, tile floors, gourmet kitchen, garage, work shop, & more! 7,000sf ocean view lot available with 100ft. of dockage for additional price. $1,900,000 ID#545881
249 Sunset Dr, Islamorada, FL 33036 is a 3 bedroom, 3 bathroom, 2,070 sqft single-family home built in 1967. It last sold for $2,100,000 on Apr 23, 2009. It is currently off market. The Trulia Estimate is $5,191,600, with a rent estimate of $5,905/month.

Home Details for 249 Sunset Dr

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Other

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: StuccoFoundation Type: Piling
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1967Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.57 acres

Price and Tax history

DateEventPrice
Aug 28, 2009
Source: Agent Provided
ListingRemoved
$1,900,000
Apr 23, 2009
Source: FLKMLS #545881
Sold
$2,100,000
Jul 23, 2008
Source: Agent Provided
PriceChange
$1,900,000
Price decreased by 41%
Jan 18, 2008
Source: Agent Provided
Listed For Sale
$3,200,000

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

Frequently asked questions about 249 Sunset Dr

  • What is 249 Sunset Dr estimated to be worth?
    Trulia's estimated value for 249 Sunset Dr in Islamorada, FL is $5,191,600.
  • What is the price history for 249 Sunset Dr?
    249 Sunset Dr in Islamorada, FL last sold for $2,100,000 in April 2009.
  • 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.
  • How big is the lot at 249 Sunset Dr?
    The lot at 249 Sunset Dr in Islamorada, FL is about 0.57 acres (24,915 sq ft).
  • Does 249 Sunset Dr have a garage?
    Yes, 249 Sunset Dr in Islamorada, FL has a garage.

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Off Market Homes Near 249 Sunset Dr

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