258 Gulfview Dr, Islamorada, FL 33036
Property image
Property image
OFF MARKET

$3,479,700

Trulia Estimate
  • 2 Beds
  • 3 Baths
  • 1,152 sqft

258 Gulfview Dr, Islamorada, FL 33036

Est. Refi. Payment $20,342/mo*
Refinance Your Home
Currently Off Market - Sold May 28, 2015 for $1,395,000

Home Value

Trulia Estimate
$3.48M
Since last month
Increased$99K (+2.9%)
Since last year
Increased$276K (+8.6%)
Since last sale
Increased$2M (+150.5%)
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 +245% in the last 10 years
MonthEstimated value
2026
August 2026$3.49M
August 2026$3.48M
July 2026$3.4M
June 2026$3.46M
May 2026$3.46M
April 2026$3.49M
March 2026$3.5M
February 2026$3.43M
January 2026$3.39M
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
202 Gulfview Dr, Islamorada, FL
0.13
Single-Family Home
$1,200,000
12/01/25
3
3
1,104
213 Nautilus Dr, Islamorada, FL
0.09
Single-Family Home
$1,300,000
04/01/26
2
2
1,530
193 Nautilus Dr, Islamorada, FL
0.15
Single-Family Home
$2,200,000
03/16/26
3
3
1,911
189 Gulfview Dr, Islamorada, FL
0.19
Single-Family Home
$2,200,000
01/12/26
3
2
2,010
140 Iroquois Dr, Islamorada, FL
0.61
Single-Family Home
$1,490,000
08/11/26
3
3
1,384
439 Palm Dr, Islamorada, FL
0.32
Single-Family Home
$1,950,000
06/12/26
4
3
2,294
64 W Plaza Del Sol, Lower Matecumbe Key, FL
0.39
Single-Family Home
$1,960,000
12/08/25
3
2
1,560
104 W Plaza Granada, Islamorada, FL
0.27
Single-Family Home
$2,241,000
12/22/25
3
2
2,200
125 Porto Vista Ct, Islamorada, FL
0.40
Single-Family Home
$3,000,000
07/07/26
3
2
1,562
154 Biscayne Blvd, Islamorada, FL
0.50
Single-Family Home
$2,500,000
08/12/26
3
2
1,368

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
233 Gulfview Dr, Islamorada, FL 33036
0.06
$2,980,200
3
3.5
2,228
Off Market
190 Venetian Dr, Islamorada, FL 33036
0.07
$2,150,600
3
3
1,200
Off Market
189 Venetian Dr, Lower Matecumbe Key, FL 33036
0.07
-
-
-
-
Off Market
218 Gulfview Dr, Islamorada, FL 33036
0.10
$3,549,400
3
3
3,660
Off Market
213 Nautilus Dr, Islamorada, FL 33036
0.09
$1,300,000
2
2
1,530
Recently Sold
172 Venetian Dr, Islamorada, FL 33036
0.11
$3,525,000
5
5.5
4,131
Recently Sold
109 Costa Bravo Dr, Islamorada, FL 33036
0.15
$900,000
2
1.5
1,322
Recently Sold
103 Costa Bravo Dr #103, Islamorada, FL 33036
0.15
$905,200
2
1.5
1,206
Off Market
164 Venetian Dr, Islamorada, FL 33036
0.14
$1,549,000
4
2
1,680
For Sale
193 Nautilus Dr, Islamorada, FL 33036
0.15
$2,200,000
3
3
1,911
Recently Sold
119 W Plaza Del Lago, Islamorada, FL 33036
0.17
$3,034,400
4
3.5
3,332
Off Market
190 Gulfview Dr, Islamorada, FL 33036
0.16
$1,772,300
4
3
1,629
Off Market

Local Information

  • Map ViewExplore the area around 258 Gulfview Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1980
1,152 sqft
$3,021/sqft

About this House

BEACHFRONT in Islamorada! You will fall in love with this location in White Marlin Beach, right on the beach with endless views of the bay. Gated for privacy, you will feel as if you are at your private beachfront resort. The living area opens to a spacious porch overlooking the bay through 2 sets of sliding glass doors. Each bedroom opens onto a porch and has its own bath.
258 Gulfview Dr, Islamorada, FL 33036 is a 2 bedroom, 3 bathroom, 1,152 sqft single-family home built in 1980. It last sold for $1,395,000 on May 28, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,479,700, with a rent estimate of $4,674/month.

Home Details for 258 Gulfview Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Tile

Exterior Features

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

Property Information

Year Built
Year Built: 1980Year Updated: 1992
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Lot Information

Lot Area: 8712 sqft

Price and Tax history

DateEventPrice
May 28, 2015
Source: FLKMLS #566752
Sold
$1,395,000
Apr 10, 2015
Source: Agent Provided
Pending
$1,515,000
Feb 21, 2015
Source: Agent Provided
Listed For Sale
$1,515,000

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 258 Gulfview Dr

  • What is 258 Gulfview Dr estimated to be worth?
    Trulia's estimated value for 258 Gulfview Dr in Islamorada, FL is $3,479,700.
  • What is the price history for 258 Gulfview Dr?
    258 Gulfview Dr in Islamorada, FL last sold for $1,395,000 in May 2015.
  • 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 258 Gulfview Dr have air conditioning?
    Yes, 258 Gulfview Dr in Islamorada, FL has air conditioning.
  • Does 258 Gulfview Dr have laundry facilities?
    Yes, 258 Gulfview Dr in Islamorada, FL has in-unit laundry.

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