133 Sunset Dr, Islamorada, FL 33036
Property image
Property image
SOLD
JUN 29, 2026

$2,896,100

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,519 sqft (on 0.28 acres)

133 Sunset Dr, Islamorada, FL 33036

Est. Refi. Payment $16,714/mo*
Refinance Your Home
Currently Off Market - Sold Jun 29, 2026 for $3,003,000 (6% below list price)

Home Value

Trulia Estimate
$2.9M
Since last month
Decreased$105K (-3.5%)
Since last year
Decreased$504K (-14.8%)
Since last sale
Decreased$97K (-3.2%)
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 +76% in the last 10 years
MonthEstimated value
2026
August 2026$2.91M
August 2026$2.91M
July 2026$3.01M
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
145 Venetian Dr, Lower Matecumbe Key, FL
0.36
Single-Family Home
$3,250,000
08/06/26
4
3.5
3,182
141 El Capitan Dr, Islamorada, FL
0.42
Single-Family Home
$2,500,000
03/13/26
4
3
2,098
442 Palm Dr, Islamorada, FL
0.57
Single-Family Home
$3,900,000
09/16/25
4
3
2,058
230 Biscayne Blvd, Islamorada, FL
0.57
Single-Family Home
$3,205,000
01/22/26
5
3
2,425
439 Palm Dr, Islamorada, FL
0.55
Single-Family Home
$1,950,000
06/12/26
4
3
2,294
182 Bayview Dr, Islamorada, FL
0.56
Single-Family Home
$3,950,000
03/06/26
4
3
3,434
140 Iroquois Dr, Islamorada, FL
0.21
Single-Family Home
$1,490,000
08/11/26
3
3
1,384
117 Sandy Cove Ave, Islamorada, FL
0.63
Single-Family Home
$1,900,000
09/15/25
4
3
1,960
193 Nautilus Dr, Islamorada, FL
0.47
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
176 Iroquois Dr, Islamorada, FL 33036
0.11
$1,356,000
2
2
960
Off Market
Sunset Dr, Islamorada, FL 33036
0.09
-
-
-
-
Off Market
Iroquois Dr, Islamorada, FL 33036
0.13
-
-
-
-
Off Market
74049 Overseas Hwy, Islamorada, FL 33036
0.11
$3,850,000
4
4
2,596
For Sale
159 Iroquois Dr, Islamorada, FL 33036
0.15
$1,675,000
3
3
2,034
For Sale
158 Iroquois Dr, Islamorada, FL 33036
0.16
$1,387,100
3
3
1,920
Off Market
Venetian Dr, Islamorada, FL 33036
0.18
-
-
-
-
Off Market
140 Iroquois Dr, Islamorada, FL 33036
0.21
$1,490,000
3
3
1,384
Recently Sold
74450 Overseas Hwy, Islamorada, FL 33036
0.21
$1,680,000
3
2
1,980
For Sale
109 Nautilus Dr, Islamorada, FL 33036
0.22
$1,056,400
2
1
900
Off Market
119 Iroquois Dr, Islamorada, FL 33036
0.26
$2,026,400
4
2
1,857
Off Market

Local Information

  • Map ViewExplore the area around 133 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
1974
Lot Size
0.28 acres
Living Area
2,519 sqft
Price/Sqft
$1,192/sqft
Parking
Garage
HOA
None

About this House

The Ospreys are back! Welcome to The Osprey's Nest; your perch by the Ocean in one of Islamorada's most coveted locations. Wake up to the sunrise and take a stroll down the turtle nesting beach, while also having the convenience of protected canalside dockage across the street. 20' dock but brought in stern-to, can accommodate larger boats. Spacious floor plan for all to enjoy, third story primary suite and beachside pool with heater and chiller for those hot summer days. True island living is here on Sunset Drive.

Listing includes canal parcel with dock across the street RE#00389220-000100
133 Sunset Dr, Islamorada, FL 33036 is a 4 bedroom, 3 bathroom, 2,519 sqft single-family home built in 1974. It last sold for $3,003,000 on Jun 29, 2026 (6% below the $3,200,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,896,100, with a rent estimate of $7,850/month.
Last check for updates: 23 minutes ago
Listed by Sabrina Wampler & Sarah Ewald, (305) 393-0585
Ocean Sotheby's International Realty
Bought with: outside of mls, Outside Of MLS
Source: FLKMLS, MLS#612438

Home Details for 133 Sunset Dr

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2519 Square Feet
Appliances & Utilities
Appliances: Refrigerator, Range, Oven, Stainless Steel Appliance(s)Refrigerator
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central Air,Ceiling Fans(s)Has HeatingHeating Fuel: Has Heating Unspecified Type
Windows, Doors, Floors & Walls
Flooring: Tile
Levels, Entrance, & Accessibility
Floors: Tile
View
No View

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/BalconyExterior: Sandy Beach, StorageHas a Private Pool
Parking & Garage
Has a GarageNo Attached GarageHas Open ParkingParking: Open
Pool
Pool: In Ground, Salt WaterPool
Frontage
WaterfrontOn Waterfront

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: CBS, Concrete
Property Information
Parcel Number: 00389750000000

Price & Status

Price
List Price: $3,200,000Price Per Sqft: $1,192/sqft

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Lower MatecumbeCommunity: Lower Mat Bch (74.0)

Building

Building Area
Building Area: 2519 Square Feet

Community

Community Features: Beach

HOA

HOA Fee Includes: NoneNo HOA

Lot Information

Lot Area: 0.28 acres

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 612438

Additional Information

Beach

Price and Tax history

DateEventPrice
Jun 29, 2026
Source: FLKMLS #612438
Sold
$3,003,000
Jun 24, 2026
Source: FLKMLS #612438
Contingent
$3,200,000
Jun 16, 2026
Source: FLKMLS #612438
PendingToActive
$3,200,000
Apr 29, 2026
Source: Key West AOR #612438
Contingent
$3,200,000
Apr 19, 2026
Source: FLKMLS #612438
PriceChange
$3,200,000
Price decreased by 9%

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 133 Sunset Dr

  • What is 133 Sunset Dr estimated to be worth?
    Trulia's estimated value for 133 Sunset Dr in Islamorada, FL is $2,896,100.
  • What is the price history for 133 Sunset Dr?
    133 Sunset Dr in Islamorada, FL last sold for $3,003,000 in June 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 133 Sunset Dr have air conditioning?
    Yes, 133 Sunset Dr in Islamorada, FL has air conditioning.
  • Does 133 Sunset Dr have a pool?
    Yes, 133 Sunset Dr in Islamorada, FL has a pool.

Explore by feature - Pet Friendly

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