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$1,399,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,006 Sq. Ft.
  • Updated 2 hours ago
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Welcome to 27416 Tobago Lane, where waterfront living and the Florida Keys lifestyle come together. This home offers open-water views and an abundance of indoor and outdoor spaces designed to make the most of island living. Boaters will appreciate the 10,000-lb boat lift and Jet Ski davit, while the fenced yard, lush tropical landscaping and multiple outdoor areas create your own private retreat. One of the home's most memorable features is the 3rd-story observation and sun deck. Take in the open-water views and ocean breeze during the day, then enjoy unobstructed stargazing and meteor showers at night. Tucked into the tropical landscaping you'll also discover a private meditation garden, orchid garden, mature fruit trees and a charming outdoor shower -- special spaces that give this property a personality all its own. Inside, high-end custom finishes and electric fireplaces add comfort and character, while an enclosed garage and oversized storage rooms provide the practical space that's so valuable in the Keys. Recent improvements include a 2025 A/C system along with a 2026 pool pump and saltwater system. Whether your perfect Keys day means heading out on the boat, relaxing by the pool, enjoying the gardens or ending the evening under the stars, 27416 Tobago Lane offers so many ways to enjoy life in the Florida Keys. Come see what makes this home special.

Full Property Details for 27416 Tobago Ln

General

  • Price: $1,399,000
  • Taxes: $7,962 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 621530
  • Updated: Today (10/7/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 1
  • Interior Features: Entrance Foyer, Fireplace(s), Quartz Countertops, Smoke Alarms, Storage
  • Appliances: Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Microwave, Oven, Refrigerator, Washer
  • Flooring: Wood, Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Pool: Yes
  • Pool Description: In Ground

Exterior

  • Exterior Features: Fencing, Fruit Tree(s), Outdoor Shower, Privacy Wall/Fence, Sprinkler System, Storage
  • Deck/Patio: Roof Top Deck, Deck
  • Porch/Patio/Deck: Roof Top Deck, Deck

Parking

  • Garage: Yes
  • Parking Features: Garage Door Opener

Location

  • Area: 09 - Ramrod Key
  • County: Monroe
  • Subdivision: Breezeswept Bch Est (27.5)

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air, Ceiling Fans(s)
  • Heating Type: Forced Air, Fireplace(s)

Utilities

  • Water: Cistern

Structural Information

  • Architectural Style: Above Flood
  • Construction Status: Updated/Remodeled
  • Construction: Frame
  • Roof: Metal
  • Windows/Doors: Shutters
  • Square Feet: 2,006
  • Sq. Ft. Source: Property Data Card
  • Year Built: 1998
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: Ocean
  • Lot Size (Acres): 0.14
  • Lot Size (Sq. Ft.): 6,000
  • Lot Dimensions: 60 x 100
  • Zoning: IS - Improved Subivision District

Water Features

  • Water Front: Yes
  • Water Front Desc.: Canal Front

Financial Considerations

  • Tax Amount: $7,962.35
  • Tax Year: 2025
  • Terms: Cash, Conventional, VA Loan

Disclosures and Reports

  • Legal Description: BK 10 LT 22 BREEZESWEPT BEACH ESTATES RAMROD KEY PB4-143 OR583-223 OR830-2209 OR1441-231/34GUARD OR1456-2467 OR1522-297
  • Flood Zone: AE
  • APN: 00204090-000000

Listed by KeyIsle Realty, Sandra Dolowy (574) 621-4857

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Listing agent

— 27416 Tobago Ln —

  • Sandra Dolowy

    KeyIsle Realty

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 27416 Tobago Ln

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Sugarloaf School
255 Crane Boulevard, Summerland Key, FL 33042
PK-87.9 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1224.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27416 Tobago Ln Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/07/2026
Listed
$1,399,000
225.35%
MLS
6/11/2010
Sold
$430,000
—
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 27416 Tobago Ln

Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,556
—
$865,620
3%
2024
$7,556
4%
$841,225
3%
2023
$7,285
21%
$816,724
40%
2021
$6,011
-15%
$582,652
-26%
2022
$7,052
17%
$783,713
49%
2021
$6,011
13%
$525,552
6%
2019
$5,300
-5%
$495,302
-3%
2018
$5,565
2%
$509,547
1%
2017
$5,477
3%
$505,156
7%
2016
$5,304
5%
$472,827
10%
2015
$5,052
6%
$429,267
1%
2014
$4,786
-1%
$426,753
2%
2013
$4,848
—
$420,446
—
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 27416 Tobago Ln

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

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with our affiliated lender
NMLS#: 1598647

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Listed by KeyIsle Realty, Sandra Dolowy (574) 621-4857

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27416 Tobago Lane, Ramrod Key, FL 33042 (MLS# 621530) is a Single Family property with 3 bedrooms and 2 full bathrooms. 27416 Tobago Lane is currently listed for $1,399,000 and was received on October 07, 2026. Want to learn more about 27416 Tobago Lane? Do you have questions about finding other Single Family real estate for sale in Ramrod Key? You can browse all Ramrod Key real estate or contact a Coldwell Banker agent to request more information.

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