77340 Overseas Highway

Islamorada, FL 33036

$3,999,999

$4,310/ft²

2Beds

2Baths

928Sq ft

1963Year built

Single-family homeType

About this home

Estate Opportunity - Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. The 2/2 pool home is updated and ready for refined living.

Features

Waterfront
Private pool

Property details

Listing

MLS #: B26001957
Status: For sale
Listed on: Mar 13, 2026
Days on market: 149 days
Listing data updated: Aug 7, 2026

Interior

Beds: 2
Baths: 2
Living area: 928 ft²
Price per ft²: $4,310/ft²

Building & community

Type: Single-family home
Year built: 1963
County: Monroe

Lot & exterior

Lot size: 34,409 ft²
Waterfront: Yes
Private pool: Yes

Days on market, price per ft² and the monthly HOA amount are calculated by this site from the MLS data shown; the association fee is normalized to a monthly figure.

True monthly cost

Mortgage (principal & interest): $20,226
Property taxes (est.): $3,667
Home insurance (est.): $600
Flood insurance (est.): —

Estimated total$24,493*/mo

* Some cost lines aren't available yet for this listing; the total shown is incomplete.

Based on 20% down, a 6.5% rate and a 30-year loan, plus this home's estimated Florida carrying costs. All figures are illustrative estimates — not quotes, not financial or insurance advice.

Sources: flood zone — FEMA National Flood Hazard Layer; mortgage, taxes and insurance figures — this site's own estimates; HOA / CDD — as reported for this listing.

What will this home really cost you?