74049 Overseas, Islamorada FL 33036, ISLAMORADA, FL, 33036
Active99 days on marketListed Apr 29, 2026MLS #A12010138
About this home
74049 Overseas, Islamorada FL 33036
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.
Facts & features
The home at a glance
4
Bedrooms
4
Bathrooms
1970
Year built
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.
$25,074 /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
$25,074/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.
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)
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 74049 Overseas
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$975,000
101 Gulfview Drive, Islam 101 Gulfview Drive # 116D, Islamorada FL 33036
3 bd · 2.5 ba · 30 DOM
Sold · Dec ’25$2,900,000
109 Sapodilla Dr, Islamorada FL 33036
4 bd · 3.5 ba · 127 DOM
Sold · Jun ’26$1,457,000
121 Venetian Dr, Islamorada FL 33036
3 bd · 2 ba · 1,278 sqft · $1,140/sqft · 556 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 74049 Overseas — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 74049 Overseas — 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
74049 Overseas FAQs
What would the monthly payment be for 74049 Overseas, Islamorada FL 33036?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $25,074/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 74049 Overseas, Islamorada FL 33036?+
The most recent tax bill on record (2025) was $21,966. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
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 74049 Overseas, 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
Listing courtesy of Paradise Florida Keys Real Est · Judy Rossignol. MLS #A12010138.
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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