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74049 Overseas Highway, Lower Matecumbe, FL 33036

New Listing
$3,999,999
Property Type: Residential Bedrooms: 4 Baths: 4 Square Footage: 1,532 Lot Size (sq. ft.): 21,000 Status: Active
Current Price: $3,999,999 List Date: 4/29/2026 Last Modified: 5/03/2026

Overview

Description

Welcome to Casa Matecumbe, an extraordinary oceanfront sanctuary located at 74049 Overseas Highway in the prestigious Village of Islamorada. This iconic property represents one of the rarest opportunities in the Upper Keys: a private, gated, resort-style compound offering expansive open-water views, unmatched privacy, and the timeless charm of classic Florida Keys architecture. Set on a generous parcel with a sandy beach, and direct ocean access, Casa Matecumbe delivers the ultimate coastal lifestyle--one defined by serenity, natural beauty, and the freedom to enjoy the water at a moment's notice. 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 locat ...

Listing Details MLS# 619687

Location, Tax & Legal

Street #
74049
Street Name
Overseas
Street Suffix
Highway
Key/Island
Lower Matecumbe
State/Province
FL
Zip Code
33036
County
Monroe
Subdivision
Lower Mat Bch (74.0)
Area
22 - Lower Matecumbe
City
ISLAMORADA
Off Shore Island
No
Mile Marker
74.5
Marathon Neighborhood
N/A
Side
Ocean
Flood Zone
VE,AE,VE,VE,VE,AE,AE
Alternate Key #
1478032
Handicap Access
Yes
Parcel #
00389650-000000
Zoning
R1 - Residential Single Family
Deed Restrictions
Unknown
Legal
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
Taxes
20640.7
Tax Year
2024
Pub Sewer HkUp
Yes

Contract Information

Listing Board
Florida Keys
As is Rght to Inspct
Yes
Species List
No

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
Yes
Control Depth
2
Pool
Yes
Year Built
1970
Total Units
Yes
Lot SqFt
21000
Lot Sqft Source
Tax Records
Acres
0.5
Living Apx SqFt
1532
SqFt Source
Tax Records
Total Bedrooms
4
Full Baths
4
Total Baths
4
Rentals Allowed
With Restrictions
Min Rental Days
7

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No
Association Fee $
0

Building Style

Above Flood
Unknown
Stories
2 Stories

More Information

Remarks & Misc

Remarks – Consumer
Welcome to Casa Matecumbe, an extraordinary oceanfront sanctuary located at 74049 Overseas Highway in the prestigious Village of Islamorada. This iconic property represents one of the rarest opportunities in the Upper Keys: a private, gated, resort-style compound offering expansive open-water views, unmatched privacy, and the timeless charm of classic Florida Keys architecture. Set on a generous parcel with a sandy beach, and direct ocean access, Casa Matecumbe delivers the ultimate coastal lifestyle--one defined by serenity, natural beauty, and the freedom to enjoy the water at a moment's notice. 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. Lower-Level Finished area of 1,065 not included in square footage. 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.
Directions
House is located oceanside on Overseas Hwy at the intersection of Overseas Hwy and Sunset Drive

Fee Includes

None
Yes
Other
Yes

Dockage

None
Yes

Tax Exemptions

None
Yes

Appliances

Dishwasher
Yes
Dryer
Yes
Microwave
Yes
Oven
Yes
Range
Yes
Washer
Yes

Pets

Pets Allowed
Yes

Cooling

Ceiling Fans(s)
Yes
Central Air
Yes

Waterfront

Oceanfront
Yes

Waterview

Ocean View
Yes

Floor

Combo
Yes
Tile
Yes

Neighborhood Feature

Beach
Yes
Bike Paths
Yes

Interior Features

Drapes/Blinds Incl
Yes
Quartz Countertops
Yes
Storage
Yes

Property Condition

Updated/Remodeled
Yes

Windows/Doors

Impact Rstnce Doors
Yes
Impact Rstnce Window
Yes

Vehicle Storage

Off Street Parking
Yes

Security

Electric Gate
Yes

Construction

CBS
Yes
Concrete
Yes

Land Size

1/4 - 1/2 Acre
Yes

Furnished

Negotiable
Yes

Terms

Cash
Yes
Conventional
Yes
FHA
Yes
No Seller Finance
Yes

Utilities

Buyer to Verify
Yes
Cable Available
Yes
Elect Separate Meter
Yes
FKAA
Yes
Municipal Sewer
Yes

Porch/Balcony

Deck
Yes
Open Porch/Balcony
Yes

Title

Negotiable
Yes

Exterior Features

Fencing
Yes
Lighting
Yes
Sandy Beach
Yes

Pool Info

In Ground
Yes
Concrete
Yes

Roof

Metal Roof
Yes

Property Features

Fee Includes: None; Other Tax Exemptions: None Waterfront: Oceanfront Waterview: Ocean View Dockage: None Property Condition: Updated/Remodeled Vehicle Storage: Off Street Parking Furnished: Negotiable Cooling: Ceiling Fans(s); Central Air Utilities: Buyer to Verify; Cable Available; Elect Separate Meter; FKAA; Municipal Sewer Interior Features: Drapes/Blinds Incl; Quartz Countertops; Storage Appliances: Dishwasher; Dryer; Microwave; Oven; Range; Washer Exterior Features: Fencing; Lighting; Sandy Beach Pool Info: In Ground; Concrete Construction: CBS; Concrete Floor: Combo; Tile Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Beach; Bike Paths Security: Electric Gate Land Size: 1/4 - 1/2 Acre Terms: Cash; Conventional; FHA; No Seller Finance Title: Negotiable
Listing Office: Paradise Florida Keys Real Estate, a Luxury Brand
Last Updated: May - 03 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.