166 Bayview Drive, Islamorada FL 33036, ISLAMORADA, FL, 33036
Pending255 days on marketListed Nov 29, 2025MLS #A11927254
About this home
166 Bayview Drive, Islamorada FL 33036
Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene. The home enjoys unobstructed water views and nightly sunsets that paint the sky in brilliant hues. A Tiki at the water's edge provides a perfect perch for morning coffee or evening cocktails, while mature landscaping adds privacy and tropical charm. Boaters will appreciate the deep-water dockage with davits, ideal for quick access to open water. The 2,478-square-foot residence features 4 bedrooms and 4 bathrooms, with tile flooring throughout and expansive windows that frame the bay. The open-concept living and dining areas flow into a well-appointed kitchen. The primary suite offers direct water views and private outdoor access. Outdoor living is elevated with a spacious pool and deck area, balcony, and brick paver walkways. The white picket fencing and lush landscaping complete the coastal aesthetic. Additional features include CBS construction, off-street parking, FKAA water service, septic system, and low HOA fees. Pets are welcome. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, 166 Bayview Drive delivers unmatched location, views, and lifestyle in the Florida Keys.
Facts & features
The home at a glance
4
Bedrooms
4
Bathrooms
1968
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.
$29,194 /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
$29,194/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 233% above the ISLAMORADA 33036 median. See the full Islamorada market guide →
Paper trail
This home's history
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
Frantreshia Miller
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 166 Bayview Drive — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 166 Bayview Drive — before you fall in love.
See it in person
Schedule a tour
Live availability from Frantreshia's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
166 Bayview Drive FAQs
What would the monthly payment be for 166 Bayview Drive, Islamorada FL 33036?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $29,194/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 166 Bayview Drive, Islamorada FL 33036?+
The most recent tax bill on record (2025) was $22,931. 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 $4,700,000, this home is listed about 31% 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 166 Bayview Drive, Islamorada FL 33036?+
Coral Shores High School (high) — Monroe County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$4,700,000 runs 233% above the ISLAMORADA 33036 median.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Time on market is leverage
255 days on market against a Islamorada median of 83 — sellers in this position are usually ready to negotiate.
04The price has already moved
Listed at $5,600,000, now $4,700,000 — a $900K cut. The full history is in the market section below.
Listing courtesy of Paradise Florida Keys Real Est · Judy Rossignol. MLS #A11927254.
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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