$3,850,000
74049 Overseas Highway
Islamorada, FL 33036
LOWER MATECUMBE BEACH
Explore the area: Monroe County real estate
Price Check
How this price compares
- List price
- $3,850,000
- Price per sq ft
- $1,483
- Original price
- Unchanged
- Days on market
- 52
This 4-bedroom single-family home is listed at $3,850,000, or $1,483 per square foot. It has been on the market for 52 days.
Estimated monthly payment
$20,233 /mo
Principal and interest only, based on $770,000 down (20%), a 6.875% 30-year fixed rate. Property taxes, homeowners insurance are not included.
Customize this estimateListing Snapshot
- Price
- $3,850,000
- Days on Site
- 52 Days
- Bedrooms
- 4
- Total Baths
- 4
- Full Baths
- 4
- Partial Baths
- 0
- Living Area
- 2,596 sqft
- Total Sq Ft
- 5,054 sqft
- Lot Size
- 0.5 Acres
- Year Built
- 1970
- Property Type
- Single Family
- MLS #
- A12064940
- Property Tax
- $24,268 (2025)
- Subdivision
- LOWER MATECUMBE BEACH
- County
- Monroe
- Status
- Active
- Special Conditions
- Listed As Is
About This Property
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.
Virtual TourGeneral Features
- Property Type
- Single Family
- Status
- Active
- Year Built
- 1970
- Property Condition
- Resale
- Number of Stories
- 2
- Levels
- Two
- Garage Spaces
- 0
- Parking
- Driveway
- Direction Faces
- Northwest
- Lot Size (Acres)
- 0.5
- Living Sq Ft
- 2,596
- Total Sq Ft
- 5,054
- Sewer
- Public Sewer
- Water Source
- Public
- Zoning
- SINGLE FAMILY RESID
Interior Features
- Appliances
- Dryer / Dishwasher / Electric Range / Microwave / Refrigerator / Washer
- Cooling
- Central Air
- Heating
- Central
- Flooring
- Tile
- Interior Features
- Family Dining Room / Main Level Primary
Exterior Features
- Construction
- Block
- Roof
- Metal
- Exterior Features
- Balcony / Outdoor Living Area
- Private Pool
- Yes
- Pool Features
- In Ground
- Patio & Porch
- Open / Patio / Balcony
- Waterfront
- Yes
- Waterfront Features
- Ocean Access / Ocean Front / Other
- Frontage
- Waterfront
- Frontage Length
- 30.00 ft
- View
- Ocean / Pool
Community & HOA
- Association Amenities
- Other
- Financing Terms
- Cash / Conventional
- Restrictions
- Ok To Lease / Rental Restriction
- MLS Area
- 5940 - Other Florida County
Schools
- Elementary School
- Plantation Key
- Middle School
- Plantation Key
- High School
- Coral Shores
About the Area
- Homes for Sale
- 41
- Median List Price
- $2,950,000
- Median $/Sq Ft
- $1,474
- Avg Days on Market
- 149
Frequently Asked Questions
- How do I schedule a tour of 74049 Overseas Highway, Islamorada, FL 33036?
- Use the Tour button on this listing to request a showing of 74049 Overseas Highway, Islamorada, FL 33036. Pick a day and time and choose an in-person or video-chat tour, and a Pure Equity agent will confirm your visit, often the same day.
- Is 74049 Overseas Highway, Islamorada, FL 33036 still available?
- 74049 Overseas Highway, Islamorada, FL 33036 is currently listed as Active, and has been on the market 52 days. Status updates directly from the MLS as homes go under contract, so ask us to confirm availability before you plan a visit.
- How much is the monthly payment for 74049 Overseas Highway, Islamorada, FL 33036?
- With 20% down ($770,000) on the $3,850,000 list price and a 30-year fixed loan at an illustrative 6.875% rate, the estimated principal & interest for 74049 Overseas Highway, Islamorada, FL 33036 is about $20,233/mo, before property taxes, insurance. Use the payment estimate on this page to adjust the down payment and rate.
- How do I get pre-approved to buy 74049 Overseas Highway, Islamorada, FL 33036?
- Getting pre-approved shows sellers you're a serious buyer and clarifies your true budget before you offer on 74049 Overseas Highway, Islamorada, FL 33036. Contact Pure Equity and we'll connect you with a trusted local lender to review your financing options, no obligation.
- What schools serve 74049 Overseas Highway, Islamorada, FL 33036?
- 74049 Overseas Highway, Islamorada, FL 33036 is zoned for Plantation Key (elementary), Plantation Key (middle), Coral Shores (high). School assignments and boundaries can change year to year, so confirm current zoning with the local school district before you buy.
- Can I negotiate the price of 74049 Overseas Highway, Islamorada, FL 33036?
- Often, yes. The right offer on 74049 Overseas Highway, Islamorada, FL 33036 depends on how it's priced against comparable single family sales in Islamorada, how long it's been listed, and how motivated the seller is. Pure Equity will run the comps and help you craft a competitive, well-supported offer.
Listing courtesy of Luxe Properties
Listing information is provided by BeachesMLS, Inc.and is deemed reliable but not guaranteed accurate by the MLS or Pure Equity. Information is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties. © 2026 BeachesMLS, Inc. Last updated August 7, 2026.
$3,850,000
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Listed by Kimberly Farias, Luxe Properties
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