249 Sunset Dr, Islamorada, FL 33036
OFF MARKET

249 Sunset Dr
Islamorada, FL 33036

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

$4,939,300

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $27,396/mo*
Refinance Your Home

$4,939,300

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $27,396/mo*
Refinance Your Home
3 Beds
3 Baths
2,070 sqft
(on 0.57 acres)

Homes for sale near 249 Sunset Dr

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Apartments for Rent

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Local Information

Map showing home location
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-- mins to
Commute Destination

Description

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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 249 Sunset Dr

DatePriceEventSource
08/28/2009$1,900,000ListingRemovedAgent Provided
04/23/2009$2,100,000Sold
FLKMLS #545881
07/23/2008$1,900,000PriceChange
Agent Provided
01/18/2008$3,200,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$35,563
Assessment$3,865,391
Home facts updated by county records

Comparable Sales for 249 Sunset Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
119 Iroquois Dr, Islamorada, FL
0.10
Single-Family Home
$1,650,000
07/08/25
4
2
1,857
158 Iroquois Dr, Islamorada, FL
0.21
Single-Family Home
$1,375,000
05/30/25
3
3
1,920
100 Iroquois Dr #5, Lower Matecumbe Key, FL
0.13
Single-Family Home
$960,000
04/21/26
4
3
1,710
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
178 Gulfview Dr, Islamorada, FL
0.71
Single-Family Home
$1,670,000
05/23/25
3
3
1,804
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
71 W Plaza Del Lago, Islamorada, FL
0.73
Single-Family Home
$2,295,000
06/04/25
4
3
2,082
176 Iroquois Dr, Islamorada, FL
0.26
Single-Family Home
$1,342,000
07/25/25
2
2
960

Assigned Schools

These are the assigned schools for 249 Sunset Dr.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

  • 66 % 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 there's wildlife

  • 54 % Say neighbors are friendly

  • 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

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
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  • Jessica
    "It is near the high school and close to Winn Dixie along with close by gas stations .................."
    0
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  • Amie B.
    "we've lived her for 1 year and lovve it, beautiful ocean views and multi million dollar homes atl around. "
    0
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  • 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
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  • 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
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  • 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

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Homes for rent near 249 Sunset Dr

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Off Market Homes Near 249 Sunset Dr

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249 Sunset Dr, Islamorada, FL 33036 is a 3 bedroom, 3 bathroom, 2,070 sqft single-family home built in 1967. This property is not currently available for sale. 249 Sunset Dr was last sold on Apr 23, 2009 for $2,100,000. The current Trulia Estimate for 249 Sunset Dr is $4,939,300.