77340 Overseas Highway, Islamorada FL 33036, ISLAMORADA, FL, 33036
Active148 days on marketListed Mar 13, 2026MLS #B26001957
About this home
77340 Overseas Highway, Islamorada FL 33036
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.
Facts & features
The home at a glance
2
Bedrooms
2
Bathrooms
928
Sqft
0.79 ac
Lot size
1963
Year built
2
Levels
$4,310
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$24,726 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$24,726/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
$/sqft vs Islamorada actives
$4,310 vs $1,291
Days on market
148 vs 83 typical
Where $4,310/sqft sits among the 20 Islamorada actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Islamorada
Get to know Islamorada. See the full Islamorada guide →
ISLAMORADA 33036 — neighborhood snapshot
Population
3,632
Median age
56.1
Median income
$88,214
Median home value
$995,600
Avg household
2.17
Households w/ children
235
For the school run
Monroe County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Islamorada market
$2.9M → $1.5M
Islamorada median sold, yr/yr
89.9%
Sale-to-list ratio (12 mo)
1 of 20
Islamorada actives have cut their price
This home is listed 183% above the ISLAMORADA 33036 median. See the full Islamorada market guide →
Paper trail
This home's history
Reality check
What actually sold near 77340 Overseas Highway
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · May ’26$2,000,000
76434 OVERSEAS HIGHWAY · same community
2 bd · 2 ba · 1,509 sqft · $1,325/sqft · 129 DOM
Sold · May ’26$2,000,000
Nearby listing · same community
2 bd · 2 ba · 1,509 sqft · $1,325/sqft · 132 DOM
Sold · Sep ’25$1,350,000
126 Columbus Dr, Islamorada FL 33036
3 bd · 3 ba · 1,066 sqft · $1,266/sqft · 13 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 77340 Overseas Highway — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 77340 Overseas Highway — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
77340 Overseas Highway FAQs
What would the monthly payment be for 77340 Overseas Highway, Islamorada FL 33036?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $24,726/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 77340 Overseas Highway, Islamorada FL 33036?+
The most recent tax bill on record (2025) was $17,789. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 77340 Overseas Highway, Islamorada FL 33036?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Islamorada?+
At $3,999,999, this home is listed about 11% above the Islamorada median of $3,595,000. The market section on this page shows how the area is trending.
Which schools are assigned to 77340 Overseas Highway, Islamorada FL 33036?+
Coral Shores High School (high) — Monroe County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Miami Association of REALTORS®.
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