Date
Details
Price
Change
Source
8/06/2026
Listed
$3,850,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$3,850,000
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Property Description
Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing property is being sold fully furnished, allowing the new owner to seamlessly continue operating it as a successful vacation rental from day one or immediately begin enjoying it as a private island retreat. Designed with flexibility in mind, this two-story home features a total of 4 bedrooms, 4 bathrooms, and two full kitchens. The upper level offers 3 bedrooms, 2 bathrooms, a full kitchen, and a private balcony, while the lower level offers a handicap-friendly layout, with a 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen. Step outside to your private pool, then take just a few steps to your own private beach, creating the ultimate island experience. A new A/C system and metal roof also adds comfort and peace of mind. Conveniently located just minutes from Robbie's Marina and Theater of the Sea, you'll enjoy world class fishing, boating, snorkeling, waterfront dining, and everything that makes Islamorada one of the premier destinations in the Florida Keys.
Full Property Details
Full Property Details for 74049 Overseas Hwy
General
- Price: $3,850,000
- Taxes: $24,268 (2025)
- Status: Active
- Type: Single Family
- Source: Greater_Miami
- MLS ID: A12064940
- Updated: 8/14/2026
- Added to Site: 16 day(s) ago
Interior
- Interior Features: First Floor Entry, Second Floor Entry, Garage Converted
- Appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Washer
- Flooring: Tile
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 4
Bedrooms
- Total Bedrooms: 4
- Bedroom Features: At Least 1 Bedroom Ground Level, Primary Bedroom Ground Level
Other Rooms
- Living Room: Garage Converted Sq. Ft.
- Dining Room: Family/Dining Combination
Additional Information
- Pool: Yes
- Pool Description: In Ground
Exterior
- Exterior Features: Open Balcony
- Deck/Patio: Open Balcony, Patio
Parking
- Carport Spaces: 1
- Covered Spaces: 1
- Parking Features: Driveway
Location
- Area: Lower Matecumbe Beach
- County: Monroe County
- Subdivision: LOWER MATECUMBE BEACH
- Building Name: LOWER MATECUMBE BEACH
- Direction Faces: Northwest
Community
- Community Name: Lower Matecumbe Beach
Heating & Cooling
- Air Conditioning: Yes
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Municipal Water
Structural Information
- Architectural Style: Detached, Two Story
- Structure Type: House
- Detached/Attached: Detached
- Construction: CBS Construction
- Roof: Metal Roof
- Building Size: 5054
- Square Feet: 2,596
- Living Area: 2,596 Sq. Ft.
- Year Built: 1970
Lot Features
- Property View: Ocean, Direct Ocean, Pool
- Lot Size (Sq. Ft.): 21,600
- Frontage Feet: 30
- Lot Features: 1/2 To Less Than 3/4 Acre Lot
- Zoning: SINGLE FAMILY RESID
- Fencing (Description): Fenced
Water Features
- Water Front: Yes
- Water Front Desc.: Ocean Access, Ocean Front
Financial Considerations
- Price Per Sq. Ft.: $1,483.05
- Tax Amount: $24,268
- Tax Year: 2025
- Terms: All Cash, Conventional
Disclosures and Reports
- Legal Description: BK 4 LOT 2 & SW'LY 30' OF NE'LY 110' TR B LOWER MATECUMBE BEACH PB3-34 LOWER MATECUMBE OR426-786 OR1368-1165 OR3185-2211 OR3275-1588
- Restrictions: Ok To Lease With Res
- Inclusions: Other
- Property ID: 00389650-000000
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Schools
Schools serving 74049 Overseas Hwy
School District:Monroe County School District, Middle Torch Key, FL
| Name | Grades | Distance |
|---|---|---|
Plantation Key School 100 Lake Road, Tavernier, FL 33070 | PK-8 | 15.1 mi |
Coral Shores High School 89901 Old Highway, Tavernier, FL 33070 | 9-12 | 15.5 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 74049 Overseas Hwy
Tax History
Tax History for 74049 Overseas Hwy
Year
Property Taxes
Change
Tax Assessment
Change
2025
$21,327
3%
$2,272,746
3%
2024
$20,641
—
$2,210,100
2%
2023
$20,652
1%
$2,160,897
7%
2021
$20,515
1%
$2,028,438
-3%
2022
$20,227
-1%
$2,092,893
-1%
2021
$20,515
13%
$2,111,665
27%
2019
$18,219
15%
$1,662,066
10%
2018
$15,819
1%
$1,510,969
-5%
2017
$15,653
1%
$1,597,514
2%
2016
$15,540
17%
$1,566,213
27%
2015
$13,294
-6%
$1,230,954
-5%
2014
$14,120
9%
$1,289,894
10%
2013
$12,948
—
$1,172,631
—
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
Estimate the Cost for 74049 Overseas Hwy
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74049 Overseas Hwy, Islamorada, FL 33036 (MLS# A12064940) is a Single Family property with 4 bedrooms and 4 full bathrooms. 74049 Overseas Hwy is currently listed for $3,850,000 and was received on August 06, 2026. Want to learn more about 74049 Overseas Hwy? 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.