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$1,489,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1,769 Sq. Ft.
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This is it!! Your Florida Key Oasis! Quintessentially Key-z, this home has it all ... and then some. Located in the very desirable Indian Waterways Community of Tavernier on Plantation Key. Stylish Two Bedroom / Two Bath Main house plus a super inviting 1/1 guest house that your guests will never want to leave! Relax and entertain in the canal front Tiki hut as you enjoy tropical breezes. Cool off on the Custom Outdoor Shower after you dock your boat. Composite Dock ensures longtime enjoyment. And an Outstanding Double-sided Garage + storage room is a major Bonus!!! As Well as the personal boat ramp, that is perfect for launching/storing a flats boat, skiff, Jet Ski, or Kayak. Both the Main House and Guest House boast gorgeous, exposed wood-beamed ceilings that are gleaming works of Art. Large Bedrooms and stylishly updated Bathrooms. Great privacy with a nature preserve across the Street CBS Construction and a White Picket Fence add to the irresistible charm of this property that personifies 'Tropical Chic.' Super Close proximity to Tavernier Creek via the famous 'Toilet Set Cut'. World Class deep water, reef, and backcountry fishing are mere minutes away as are incredible diving, snorkeling, Lobstering, and sandbar-ing! Come Grab a slice of Florida Keys Living!

Full Property Details for 157 Caloosa St

General

  • Price: $1,489,000
  • Taxes: $9,745 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 617892
  • Updated: 1/1/2026
  • Added to Site: 16 day(s) ago

Interior

  • Appliances: More Appliances, Stainless Steel Appliance(s), Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Shared Amenities: Community Boat Ramp

Exterior

  • Exterior Features: Chickee Hut, Storage, Outdoor Shower, Detached Guest Qtrs

Parking

  • Garage: Yes
  • Parking: Garage, RV Parking Open, Trailer Storage, Detached

Location

  • Area: 25 - Plantation Key
  • County: Monroe
  • Subdivision: Indian Waterways (89.0)
  • Driving Directions: Overseas Highway to Caloosa

Community

  • Assoc. Fees Include: None
  • Pet Restrictions: See Local Ordinances

Heating & Cooling

  • Cooling Type: Central Air, Ductless, Ceiling Fans(s)

Utilities

  • Water: Canal View
  • Utility Description: FKAA, Buyer to Verify

Structural Information

  • Architectural Style: Single Family
  • Construction: CBS
  • Roof: Metal Roof
  • Square Feet: 1,769
  • Sq. Ft. Source: Tax Records
  • Year Built: 1960

Lot Features

  • Lot Size (Sq. Ft.): 6,600
  • Zoning: R1 - Residential Single Family

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Type: Canal Front
  • Dock Description: Boat Ramp

Financial Considerations

  • Tax Amount: $9,745
  • Tax Year: 2025
  • Terms: Cash, Conventional

Disclosures and Reports

  • Flood Zone: AE

Listed by American Caribbean Real Estate, Christie's International Real Estate, Mykael A. Marinelli (305) 439-7730

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Listing agent

— 157 Caloosa St —

  • Mykael A. Marinelli

    American Caribbean Real Estate, Christie's International Real Estate

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 157 Caloosa St

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Plantation Key School
100 Lake Road, Tavernier, FL 33070
PK-80.2 mi
Coral Shores High School
89901 Old Highway, Tavernier, FL 33070
9-120.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 157 Caloosa St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/01/2026
Listed
$1,489,000
92.13%
MLS
9/07/2018
Sold
$775,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 157 Caloosa St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$9,132
—
$1,176,801
1%
2024
$9,132
7%
$1,159,810
10%
2023
$8,543
11%
$1,049,718
20%
2022
$7,715
14%
$878,241
47%
2021
$6,747
—
$597,344
3%
2021
$6,747
—
$577,835
-1%
2019
$6,733
12%
$581,425
14%
2018
$6,002
6%
$512,077
—
2017
$5,663
5%
$512,077
18%
2016
$5,389
6%
$433,798
5%
2015
$5,105
1%
$414,374
5%
2014
$5,065
5%
$394,389
10%
2013
$4,831
—
$358,536
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 157 Caloosa St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by American Caribbean Real Estate, Christie's International Real Estate, Mykael A. Marinelli (305) 439-7730

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157 Caloosa Street, Islamorada, FL 33070 (MLS# 617892) is a Single Family property with 3 bedrooms and 3 full bathrooms. 157 Caloosa Street is currently listed for $1,489,000 and was received on January 01, 2026. Want to learn more about 157 Caloosa Street? Do you have questions about finding other Single Family real estate for sale in Islamorada? You can browse all Islamorada real estate or contact a Coldwell Banker agent to request more information.

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