74049 Overseas Islamorada, FL $ 3,999,999
74049 Overseas
$ 3,999,999
Recently Listed
Open House 5/2 12pm - 4pm
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74049 Overseas

Islamorada, FL, 33036
$ 3,999,999
Bedrooms4 Baths4.0

Monthly Estimate*

$ 24,629

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Single Family Home for sale in Islamorada, FL

for $3,999,999 with 4 bedrooms and 4 full baths. This home was built in 1970.

The gated entrance supplies a perfect level of privacy. The approach sets the tone for the entire experience: peaceful, secluded, and authentically 'Old Florida,' yet elevated with the sophistication expected in a luxury Keys residence. Whether used as a full-time home, a seasonal retreat, or a legacy property to be enjoyed for generations, Casa Matecumbe offers a rare combination of location, land, and lifestyle that is nearly impossible to replicate. The main residence is thoughtfully positioned to maximize panoramic ocean views from nearly every room. Expansive windows and glass doors frame the turquoise water, inviting natural light to fill the interior spaces throughout the day. Upstairs there are 3 bedrooms and 2 baths as well as a gorgeous kitchen an open concept with dining under air conditioning or al fresco, Downstairs includes a large en-suite bedroom with water views as well as an additional kitchen and dining living area. Both levels offer a breezy indoor-outdoor living--with modern comforts including updated finishes, impact windows, and spacious living areas. This 4-bedroom House is the perfect vacation home for larger families wishing to enjoy the pool, the beach and the ocean in a private setting.

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Open House

5/2/2026 12:00 PM - 4:00 PM
74049 Overseas Islamorada, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 3,999,999

Bedrooms

4

Full Bath

4

Property Type

Single Family

Taxes

$ 21,966

Style

Year Built

1970

Town/City

Islamorada

County/Region

Monroe

MLS | Web ID

A12010138

Features
General
Sewer Public Sewer
Heating Heat Pump
Cooling Central Air Ceiling Fan(s)
Possession Closing & Funding
Roof Metal
Appliances Dryer Dishwasher Electric Range Microwave Refrigerator Self Cleaning Oven Washer
Garage Spaces 0
Patio/Porch Features Deck Open Patio Porch
Architectural Style Detached Two Story
Pool Features Concrete Heated In Ground Pool
Restrictions OK To Lease Rental Restriction
Construction Materials Block
Year Built 1970
View Ocean
Stories Count 2
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Waterfront Features Ocean Front
County Monroe
Property Type Residential
Subdivision Name Lower Matecumbe
Facing Direction Northwest
Garage Y/N false
Total Rooms 0
Full Baths 4
Special Listing Conditions Listed As-Is
Status Active
City Islamorada
Disclosures Owner Is Listing Agent
Senior Community Y/N false
Zoning Description SFH R1
MLS Area 98 Florida Keys
Lot Size Units Square Feet
Lot Size Square Feet 21000
Carport Spaces 1
Carport Y/N true
Listing Terms Cash Conventional
Year Built Details Unknown
Tax Annual Amount 21966
MLS Area Minor Other Geographic Area (Out Of Area Only)
Lease Considered Y/N true
Virtual Tour https://player.vimeo.com/video/1137336788
Standard Status Active
Occupancy Type Call Agent
Property Sub Type Additional Single Family Residence
Legal Description BK 4 LOT 2 & SW'LY 30' OF NE'LY 110' TR B LOWER MATECUMBE BEACH PB3-34 LOWER MATECUMBE OR426-
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Interior
Interior Amenities Bedroom on Main Level Second Floor Entry First Floor Entry Handicap Access Main Level Primary Upper Level Primary
Flooring Tile
Air Conditioning Y/N true
Heating Y/N true
Total Bedrooms 4
Total Baths 4
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Exterior
Exterior Amenities Deck Fence Security/High Impact Doors Lighting Porch Patio
Parking Features Guest RV Access/Parking
Lot Features 1/4 to 1/2 Acre Lot
Water Source Public
Lot Size Area 21000
Frontage Length 104
Waterfront Y/N true
Covered Spaces 1
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* Excluded Features
List By
Paradise Florida Keys Real Est

Broker

islamoradajudy@gmail.com

Email

Affordability Calculator

$26,459
Per Month
93%
7%
0%
Monthly Principal & Interest
$24,629
Monthly Property Taxes
$1,831
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
4/30/2026$3,999,999 Listed Price

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74049 Overseas, Islamorada, FL, 33036 is a Single Family Home for sale at $3,999,999. 74049 Overseas has 4 bedrooms, 4.0 baths, and was built in 1970. The property's zip code is 33036 which is in Islamorada, FL