Southwest Florida's Only 1% Commission Specialists — Save $40,000 on a $1M Sale · 35 Years Experience

Realty of Naples FL

1% Commission Specialists

Call Scott

(239) 910-6772

Call Blane

(239) 357-1308

Free Consultation

Search by City

Selling

Tools & Calculators

Guides

Blog

What You Save Our 1% Fee About Us Contact Gated Communities ↗

4440 Smugglers DR, Upper Captiva, FL 33924

Closed

$895,000

Closed

4440 Smugglers DR, Upper Captiva, FL 33924

$895,000

Overview

224031216
Property ID

Stilts, Residential
Property Type

3
Bedrooms

2
Bathrooms

3251 Sqft
Area Size

0.2152 Acres
Land Area

1985
Year Built

Description

FANTASTIC North Captiva Island Opportunity! Prime Rental Opportunity! Welcome to Your Own Private Island Oasis, Great Island Location, Peaceful, One Story, Heated Pool Home surrounded by a Mature Lush and Tropical Landscape. Great Short Term Vacation Rental Property with Upcoming Bookings in Place. Optimal Mid Island Location with Very Short Walk or Golf Cart Ride to the Beach or to the Island Club at North Captiva and all it has to offer! Lovely Island Full Time Residence, Perfect Island Vacation Rental or Combination! Prime Busy and Operating Short Term Vacation Rental. Vibrant Eclectic Kitchen with All Appliances in Place, Plenty of Countertop and Cabinet Space. Large Front Open Balcony and Outdoor Space for Entertaining and Enjoyment. Multiple Sets of French Doors to bring the Outdoors In! Vaulted Bright Main Living and Dining Area. Vaulted Main Bedroom with French Doors to the Open Balcony. SQ Footage includes 860 SQ FT+ in the Upper Living Area consisting of 2 Bedrooms (1 King and 1 Bunk Room with 2 Twins and a Full) and 2 Full Baths with Showers. Additional Finished Lower Level of 432 SQ FT+ with 1 Queen Bedroom with French Doors Out to the Inground Pool, 1 Half Bath, Inside Laundry, and a Large Owners Bonus Room, Storage Room, or another Guest Bedroom! Inside Laundry Closet offers Full Size Washer and Dryer. Private Well and Septic not shared. Being Sold Turnkey Furnished! Nestled Among the Palm Trees "Smugglers Hideaway" is an Island Home that you will want to consider! Fantastic Rental History and Consistent Regular Visits by Owner. Bring Your Offers!

—

Asking Price

—

Bedrooms

—

Bathrooms

—

Sq Ft

—

Type

—

Year Built

Schedule a Showing

Tour this — bed, — bath home in Naples

Scott Cowan has 35 years of experience in the Naples market. He'll walk you through every detail of this property and give you an unfiltered assessment of its value.

Book a Showing →

Own a home in Naples?

A comparable home listed with us saves you $50,000 in commission

Homes like this one — single family residences in Naples — sell for significant commissions at traditional brokerages. We charge 1% and deliver the same full-service listing.

See Exact Savings →

Seller Net Sheet

What would you walk away with on a home at this price?

Our free seller net sheet calculates your proceeds after commission, closing costs, and taxes — so you know exactly what hits your account at closing. No guesswork.

Run the Numbers →

Property Details

Listing Info

Status—

List Price—

Property ID—

County—

Year Built—

Land Area—

Rooms & Parking

Bedrooms—

Bathrooms—

Garages—

Living Area—

HOA / Month—

Parking—

Construction

Style—

Roof—

Flooring—

Cooling—

Heating—

Pool—

Community & Setting

Waterfront—

Property Type—

Features—

Insurance Cost Estimator

What Will You Pay to Insure This Property?

Annual insurance estimates for this ZIP code, property type, and price tier. SWFL-specific breakdown.

Estimated Total Annual Insurance

—

All coverages combined estimate

Monthly Reserve

—

Risk Factors for This Property

Wind Zone—

Flood Zone (typical)—

Hurricane Exposure—

Roof Age ImpactSignificant — verify age

Citizens Eligibility—

Post-Ian MarketRates elevated 30–60% vs 2021

Active Carriers in This Market

Citizens Property Insurance

Florida's insurer of last resort. Available if private market declines. Strict eligibility rules post-2023 reforms.

Universal Property & Casualty

One of the largest private carriers still writing in SWFL. Rates have increased significantly since Ian.

Florida Peninsula Insurance

Active in Collier and Lee County. Competitive for newer construction homes.

Security First Financial

Writing policies in SWFL. Strong for homes with impact windows and newer roofs.

Chubb / AIG (Luxury tier)

For homes above $1M. Offers agreed-value policies and broader coverage. Rates are higher but coverage is more comprehensive.

🏠

Impact Windows = Lower PremiumVerified impact-rated windows and doors can reduce wind premium by 15–30%. Always request the wind mitigation credit report from seller.

📋

Roof Age is CriticalMost SWFL carriers will not write policies on roofs over 15 years old. A roof over 10 years old triggers higher premiums. Request permit history before making an offer.

📐

Elevation Certificate Saves MoneyFor flood insurance, an elevation certificate showing the home is above Base Flood Elevation can cut NFIP premiums by 50% or more.

⚡

Get Quotes Before ClosingIn SWFL's current market, insurance quotes must be in hand before removing financing contingencies. Some homes in high-risk zones cannot be insured at any reasonable price.

Compare Insurance Rates → Insurance Guide

Insurance estimates are ranges based on current SWFL market conditions, ZIP code risk profiles, property type, and price tier. Actual premiums depend on specific carrier, coverage selections, roof age, construction type, wind mitigation credits, elevation certificate, and claims history. These are estimates only — not quotes. Always obtain binding quotes from licensed Florida insurance agents before closing. The SWFL insurance market has been volatile since Hurricane Ian (2022) and rates continue to change. Estimates reflect approximate 2024-2025 market conditions.

HOA Deep Dive

What Does the HOA Actually Cost — and Cover?

Your true monthly payment goes well beyond the mortgage. Here's the full picture including HOA, taxes, and insurance.

Purchase Price

HOA / Month

Interest Rate

Down Payment

Monthly CostMonthlyAnnual

Monthly Payment Breakdown

Mortgage Only vs True Monthly Cost

What HOA Fees Typically Cover in This Price Range

HOA fee is sourced from MLS listing data. Tax estimate uses Collier/Lee County effective millage rates applied to purchase price. Insurance estimate is based on ZIP code risk profile. Actual costs vary — always request the HOA's current budget, reserve study, and financials before closing. Buyers have a right to review HOA documents during the inspection period.

Property Tax Estimate

Estimated Annual Property Tax — This Property

Based on Collier County millage rates and Florida exemption rules.

Estimated Annual Tax

—

Without homestead exemption

Monthly Tax Reserve

—

Budget this for escrow

Effective Tax Rate

—

Collier County

Millage Rate

—

Per $1,000 assessed value

Florida Tax Exemptions Available

Homestead Exemption

$50,000 off assessed value for primary Florida residence. First $25K applies to all taxes; second $25K applies to non-school levies.

Non-primary

Save Our Homes Cap

Once homestead is established, annual assessed value increases are capped at 3% or CPI — whichever is lower. Massive long-term savings.

If primary

No State Income Tax

Florida has no personal income tax. For high-net-worth buyers relocating from NY, NJ, or CT, this often offsets property tax entirely.

Always applies

Senior / Disability Exemptions

Additional exemptions available for residents 65+ with income below county threshold, and for certain disabilities. County-specific.

Income-based

Tax Breakdown by Millage District

Collier County General—

School Board (state)—

School Board (local)—

Water Management District—

City of Naples (if applicable)—

Special Districts / Other—

Estimated Annual Total—

Tax Scenarios

No Exemption

—

Investment / second home / new buyer first year

With Homestead

—

Primary Florida residence, $50K assessed value reduction

After 5 Years SOH

—

Save Our Homes cap — estimated if market rises 5%/yr

New York Comparison

—

Equivalent NY effective rate ~1.7% — FL is lower

Collier County PAO → Full Tax Guide

Estimates use Collier County Property Appraiser published millage rates for tax year 2024. Assessed value for a new purchase is typically set near the purchase price in the first year; subsequent years are subject to Save Our Homes caps if homestead is established. This is an estimate only — not a tax bill. Verify current millage rates and exemption eligibility with the Collier County PAO and a qualified tax advisor.

What's Nearby

Around this property

Loading nearby places…

Drive Time Analysis

How Far Is Everything from This Property?

Real drive times calculated from this address — not straight-line distance.

Downtown Naples

— min

5th Avenue South

Dining, galleries & boutiques

RSW Airport

— min

SW Florida Intl Airport

Fort Myers — nearest major airport

Luxury Shopping

— min

Mercato

Dining, Whole Foods & boutiques

Top Hospital

— min

NCH Baker Hospital

Naples Community Health — Level II

🏖

Gulf Beach

— min

Naples Beach (Gulf Shore Blvd)

🛒

Whole Foods

— min

Whole Foods Naples

✈

Naples Airport

— min

Naples Municipal (APF)

🏌

Tiburón Golf

— min

Tiburón at Ritz-Carlton

Drive times calculated using OSRM open-source routing via OpenStreetMap road network data. Times reflect typical driving conditions and may vary with traffic. Distances shown in miles.

True Cost of Ownership

What Will This Home Actually Cost Over 5 & 10 Years?

Beyond the mortgage — taxes, insurance, HOA, maintenance, and projected equity. Pre-filled from this listing.

Purchase Price

Down Payment

Interest Rate

HOA / Month

5-Year View

10-Year View

Equity & Appreciation

Cost CategoryAnnualYear 3Year 55-Yr Total

5-Year Cost Breakdown by Category

Cost CategoryAnnualYear 5Year 1010-Yr Total

10-Year Cost Breakdown by Category

Scenario5-Year Equity10-Year Equity

Equity Growth vs Total Cost Paid — Naples Historical Avg (~5%/yr)

True cost of ownership calculations are estimates based on inputs provided and SWFL market averages. Mortgage P&I uses standard amortization. Property tax uses the effective rate at purchase price. Insurance uses ZIP-based estimates. Maintenance reserve is set at 1% of purchase price annually — a conservative industry standard. HOA fees are pre-filled from MLS data where available. Appreciation scenarios are illustrative — Naples has averaged approximately 5% annual appreciation over the past 10 years but past performance does not guarantee future results. This calculator is for planning purposes only and is not a financial guarantee.

Neighborhood Profile

Who Lives Here — and What Has the Market Done?

Demographics and 5-year price trends for this area. Key data for buyers relocating from the Northeast.

DemographicThis ZIPFL Avg

Household Income Distribution

Median Home Price — 5-Year History

Where Buyers Are Coming From — Top States Moving to SWFL

Demographic data is sourced from U.S. Census Bureau American Community Survey (ACS) 5-year estimates and USPS migration data. Median home prices are based on SWFL MLS closed sales data and Zillow Research ZIP-level estimates. Migration data sourced from IRS SOI migration patterns and Florida Department of Revenue. All figures are estimates and may not reflect the most current market conditions. For current market data, contact Scott Cowan for a full market analysis.

Listing History

Days on Market & Price History

Listing activity for this property.

Days on market and price history are sourced from MLS data fields available on this page. For closed or off-market listings, full history may not be available in the public feed. Always verify current listing status with your agent.

School District

Schools Serving This Property

Public school assignments for this address based on ZIP code boundaries.

School District

—

District Rating

—

County

—

District Website

View →

Notable Private Schools in the Area

School assignments are based on ZIP code boundaries and are subject to change. Always verify current school zoning directly with the district before purchasing. Ratings sourced from Florida Department of Education school grades and GreatSchools data. Florida DOE School Grades →

Pricing Analysis

Price Per Sq Ft — How Does This Home Compare?

This Home
—
per sq ft asking price

ZIP Average

—

Active listings in this ZIP

vs ZIP Average

—

vs area market

Home Size

—

sq ft living area

$/Sq Ft — This Home vs Naples Market Benchmarks

ZIP code averages are estimated benchmarks based on publicly available Southwest Florida MLS data ranges and are provided for context only — not a formal appraisal. Actual market averages change daily. Contact Scott Cowan for a current comparative market analysis (CMA) at no obligation.

Flood Zone & Insurance Risk

Flood Risk Assessment — This Property

FEMA Flood Zone

—

Loading…

Flood Insurance

—

Annual estimate

Flood Required?

—

If federally backed mortgage

Annual Risk Level

—

Chance of flooding per year

FEMA Flood Zone Reference

Zone X

Minimal risk — outside 500-yr flood plain

Zone AE

High risk — 1% annual chance, base flood elevations determined

Zone VE

Highest risk — coastal with wave action, mandatory insurance

Zone A

High risk — 1% annual chance, no base elevation data

Run Full Flood Zone Lookup → Compare Insurance Rates → View FEMA Flood Map ↗

Flood zone data sourced from the FEMA National Flood Hazard Layer (NFHL) via the FEMA Map Service Center API. Insurance estimates are ranges based on FEMA NFIP rate tables for Southwest Florida and are not a quote. Actual premiums depend on elevation certificate, building characteristics, and coverage selections. Always obtain a formal flood insurance quote before closing. Verify on FEMA.gov →

Hurricane Risk

Hurricane Risk Assessment — This Property

Historical storm track data and risk scoring for this ZIP code.

Composite Hurricane Risk Score

—

/100

Loading…

Storms Within 50mi

—

Since 1851 (NOAA records)

Cat 3+ Within 50mi

—

Major hurricane tracks

Last Direct Hit

—

Nearest landfall

Avg Return Period

—

Years between major events

Notable Storms — Collier & Lee County (1950–2024)

Ian

2022

Cat 5

Irma

2017

Cat 3

Wilma

2005

Cat 3

Charley

2004

Cat 4

Donna

1960

Cat 4

Milton

2024

Cat 3

What to Ask Before You Buy

✅

Impact Windows & Doors

Verify all openings are impact-rated. Retrofitting after purchase costs $30,000–$80,000+ on a large home. Ask seller for permits.

📋

Roof Age & Material

Insurance carriers in SWFL require roofs under 15 years old. Metal or concrete tile preferred. Request roof permit and last inspection report.

🔌

Generator & Transfer Switch

Whole-home generator is standard at the luxury tier. Verify fuel type (natural gas preferred), capacity, and last service date.

🏘

Evacuation Zone

Collier County uses zones A–E. Zone A is highest risk and evacuates first. Check Collier County EM for this address.

Check Evacuation Zone → Hurricane Guide

Risk scoring is based on NOAA HURDAT2 historical storm track data (1851–2024) and Collier/Lee County proximity analysis. This is a historical risk assessment, not a forecast. All construction in Florida must meet the Florida Building Code hurricane standards enacted after 2002. Verify current insurance availability and windstorm coverage requirements with a licensed Florida insurance agent before purchase.

Mortgage Calculator

Estimate Your Monthly Payment

Pre-filled with data from this listing. Adjust any field.

Purchase PriceFrom this listing

Down Payment

Interest Rate

Loan Term

years

Property Tax Rate

Home InsuranceAnnual premium

Monthly HOA Fees

PMI RateRequired if down payment < 20%

⚠️ Your down payment is below 20% — PMI is included in the total. PMI is typically removed once you reach 20% equity. At this price tier most lenders require jumbo loan terms; consult your lender for exact PMI structure.

This calculator provides estimates only. Actual payments depend on lender-specific rates, points, closing costs, and escrow requirements. Property tax uses the effective rate applied to purchase price — assessed value may differ after purchase. Consult a licensed mortgage professional before making financial decisions.

Estimated Monthly Payment

—/mo

P&I

—

Tax

—

HOA

—

Insurance

—

PMI

—

Purchase Price —

Down Payment —

Loan Amount —

Principal & Interest —

Property Tax —

Home Insurance —

Monthly HOA —

PMI —

Monthly Total —

Talk to Scott About Financing →

Realty of Naples — 1% Commission

Interested in this property?

Realty of Naples represents buyers and sellers across Southwest Florida at 1% commission. Whether you want to schedule a showing or list your own home, our team saves you tens of thousands compared to a traditional brokerage.

Schedule a Showing — Talk to Scott Calculate Your Savings

Selling in Naples? 1% Commission

Listing price —

Traditional agent (6%) —

Realty of Naples (1%) —

You keep

—

more at closing vs a 6% agent

Based on this listing's asking price. No obligation, no pressure.

Active For Rent

$2,200

Active For Rent

1882 Tarpon Bay S DR, Naples, FL 34119

$2,200

1882 Tarpon Bay S DR , 34119, NAPLES

Beds: 2
Baths: 2
Low Rise (1-3), Residential Lease

Details

Naples Realty

6 minutes ago

Naples Realty

6 minutes ago

Active For Rent

$3,600

Active For Rent

4060 Ice Castle WAY, Naples, FL 34112

$3,600

4060 Ice Castle WAY , 34112, NAPLES

Beds: 2
Baths: 2
Low Rise (1-3), Residential Lease

Details

Naples Realty

6 minutes ago

Naples Realty

6 minutes ago

Details

Property ID 224031216
Price $895,000
Property Size 3251 Sqft
Land Area 0.2152 Acres
Bedrooms 3
Bathrooms 2
Garage Size x x
Year Built 1985
Property Status Closed
Property Type Stilts, Residential

Additional details

Roof Shingle
Sewer Septic Tank
Cooling Ceiling Fan(s),Central Electric
Heating Central Electric
Flooring Laminate,Tile
County Lee
Property Type Residential
Pool Below Ground,Fiberglass,Electric Heat,Pool Bath
Parking Driveway Unpaved,Attached Carport
Waterfront None
Architectural Style Single Family