Trade Winds Avenue

Naples | Florida

Where Legacy

Becomes Home

View Photos Watch Film 360° VTour Open House

Maureen Sexson

Presented At

$8,000,000

Bedrooms

Bathrooms

Living

4,669

SQFT

Fireplace

High Ceiling

Library

Office

Stone Countertops

Elevator

Washer Dryer

Bar

Kitchen island

Laundry Room

Jacuzzi

Gas Stovetop

Terrace

Garage

Outdoor Living Space

Garden

Balcony

Fire Pit

Pool

Outdoor Kitchen

Water View

Coastal

Waterfront

New Builds

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273

Trade Winds Avenue

Naples | Florida

273 Trade Winds Avenue, Naples, FL 34108, Naples, Florida, United States. , Naples , Florida 34108

.

Panoramic bayfront living along Vanderbilt Beach. Positioned along the centerline of Conners Bay, this new construction estate-crafted by Milestone Development with interior selections by Tye Interior Design offers mile-long water views and refined living in one of Naples desirable coastal settings. The residence reflects a balance of timeless design and modern luxury. The main living level features 12-foot ceilings, custom ceiling treatments and wide-plank hardwood floors that frame sweeping views of the bay. A chef's kitchen anchors the space, highlighted by a quartzite waterfall island, professional-grade appliances, and a discreet butler's pantry designed with functionality and elegance in mind. Seamless transitions lead to nearly 500 square feet of covered outdoor living with a summer kitchen, fireplace and unobstructed bay views ideal for year-round alfresco entertaining. The primary suite is a private retreat, complete with a dedicated coffee bar and dual custom wardrobes. A separate study on the main floor offers versatile use as a library, office or media room. The third-floor loft provides an additional gathering area or private lounge for three guest en-suite bedrooms, all opening to a covered balcony with commanding water views. Additional features include a heated saltwater pool and spa, a four-plus-car garage, a recreation room and a newly constructed dock with boat lift. With direct access to the Gulf in just seven minutes by water, this is an exceptional opportunity to own a waterfront lifestyle residence distinguished by superior craftsmanship and design pedigree.

Gallery

3D Street View Tour

Property Location

273 Trade Winds Avenue, Naples, FL 34108, Naples, Florida, United States., Naples Florida

Local Weather & Climate

Naples, Florida

Current Conditions Updated recently

55 °F

Broken clouds

Feels Like 54°F

Humidity 79%

Wind 10 mph

Visibility 6.2 mi

Sunrise 11:32 AM

Sunset 11:37 PM

5-Day Forecast

Thu 19 Mar

Clouds

High 74°

Low 56°

Fri 20 Mar

Clear

High 76°

Low 58°

Sat 21 Mar

Clear

High 74°

Low 58°

Sun 22 Mar

Clear

High 75°

Low 61°

Mon 23 Mar

Clear

High 75°

Low 63°

Data from OpenWeatherMap

Walkability & Transit Scores

How easy is it to get around Naples?

Walkability and transit scores for this address come from the EPA National Walkability Index.

Mortgage Calculator

Estimate your monthly payments for this property

Home Price

Down Payment

$100,000

Interest Rate

Loan Term

Estimated Monthly Payment $3,160

Monthly Payment Breakdown

Principal & Interest $2,528

Loan Amount $400,000

Total Interest $337,621

Total Cost $737,621

Potential Tax Benefits (United States)

$0 Est. First Year Interest Deduction

$0 Est. Annual Tax Savings

*Based on post-2017 tax law. Actual deductions depend on filing status, itemization, and current tax laws.

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Important Information

This calculator is for illustrative purposes only and does not constitute a loan offer, pre-approval, or commitment to lend.
Monthly payment estimates do not include property taxes, homeowner's insurance, HOA fees, or other applicable costs which may significantly increase your actual payment.
Interest rates shown are for demonstration only. Actual rates depend on your credit score, down payment, loan type, property location, and current market conditions.
This tool provides estimates only. Consult with a licensed mortgage professional for accurate quotes and personalized advice.
Tax benefit calculations are simplified estimates based on general assumptions for United States. Actual deductions depend on your specific tax situation, filing status, and current tax laws.
Tax Year Information: Tax data shown is based on United States tax year 2025 (fiscal year: January-December), rules effective from 2018 through 2025. Tax laws change frequently and may have been amended since this data was compiled.

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The tax benefit information displayed on this page is provided for general informational and educational purposes only. This information:

Does not constitute tax advice and should not be relied upon as such. Tax laws are complex and vary by jurisdiction, individual circumstances, and are subject to change without notice.
May not be current or accurate for your specific situation. Tax rules are updated frequently by governments, and the information shown may not reflect the most recent changes.
Uses simplified assumptions that may not apply to your circumstances, including filing status, total income, other deductions, alternative minimum tax considerations, and local tax variations.
Should not be used as the basis for any tax planning decisions or financial strategies without consulting a qualified tax professional licensed in your jurisdiction.

Before making any decisions based on potential tax benefits, you should consult with a qualified tax advisor, certified public accountant (CPA), or licensed tax professional who can evaluate your specific circumstances and provide advice tailored to your situation.

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Neighborhood Demographics

ZIP 34108 • 2022 ACS Data

16,401 Population

Median Age: 67.0

$115,182 Median Income

High

$903,100 Median Home Value

Rent: $1,843

59.7% College Graduates

High

Housing

Homeowners 47.9%

Renters 8.1%

Vacancy Rate 44.0%

Employment

2.8% Unemployment

26.5% Work From Home

Education Attainment (Age 25+)

High School+ 96.8%

Bachelor's+ 59.7%

Graduate+ 25.0%

Data from U.S. Census Bureau American Community Survey 2022

Local Market Trends

Real estate market data for Naples

Balanced Market Balanced market conditions

$1,362,000

Median Sale Price

$641

Price per Sq Ft

Avg Days on Market

Data provided by RentCast

Frequently Asked Questions

Common questions about this property

How many bedrooms and bathrooms does 273 Trade Winds Avenue, Naples, FL 34108, Naples, Florida, United States have?

This house at 273 Trade Winds Avenue, Naples, FL 34108, Naples, Florida, United States features 4 bedrooms with 4,669 square feet of living space.

What is the size of 273 Trade Winds Avenue, Naples, FL 34108, Naples, Florida, United States?

This property offers 4,669 square feet of living space.

What is the listing price for 273 Trade Winds Avenue, Naples, FL 34108, Naples, Florida, United States?

This property is listed at $800,000,000, which equals $171343 per square foot.

What type of property is 273 Trade Winds Avenue, Naples, FL 34108, Naples, Florida, United States?

This is a house located in Naples, Florida. The property is situated in an established neighborhood with convenient access to local amenities and services.

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