4255 Gordon Dr, Naples, FL 34102
Property image
Property image
OFF MARKET

4255 Gordon Dr
Naples, FL 34102

Port Royal
  • 3 Beds
  • 3.5 Baths
  • 4,037 sqft (on 0.80 acres)

$18,118,900

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $107,200/mo*

$18,118,900

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $107,200/mo*
3 Beds
3.5 Baths
4,037 sqft
(on 0.80 acres)

Local Information

  • Map ViewExplore the area around 4255 Gordon Dr.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1981
Lot Size
0.8 acres
Living Area
4,037 sqft
Price/Sqft
$4,488
Parking
Garage

About this House

H.12797 - One of a kind property located on prestigious south Gordon Dr. with approximately 131 ft of big beautiful waterfront vistas and perfectly situated to overlook Cutlass Cove all the way out into Admiralty Bay. Charming house with 4,037 Sq.ft. of living space with features such as wood siding, pine tongue and groove ceiling detail, wood flooring, custom millwork, fireplace and large balcony with water views. Eligible for immediate Port Royal membership as well as the Cutlass Cove Beach Club. The Cutlass Cove Beach Club allows beach access and private tranquility only a short stroll away. Don't miss one of the best opportunities in Port Royal today!
4255 Gordon Dr, Naples, FL 34102 is a 3 bedroom, 4 bathroom, 4,037 sqft single-family home in Port Royal, built in 1981. It last sold for $7,900,000 on Oct 16, 2018. It is currently off market. The Trulia Estimate is $18,118,900, with a rent estimate of $153,928/month.

Home Details for 4255 Gordon Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Interior Details
Number of Rooms: 2Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: Wood
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1981Year Updated: 1981
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.80 acres

Price History for 4255 Gordon Dr

DatePriceEventSource
10/16/2018$7,900,000Sold
N/A
09/18/2018$8,600,000PendingAgent Provided
02/16/2018$8,600,000Listed For SaleAgent Provided
01/01/2018$8,900,000ListingRemovedAgent Provided
02/14/2017$8,900,000PriceChange
Agent Provided
07/11/2016$9,500,000Listed For SaleAgent Provided
05/22/2002$3,500,000Sold
N/A

Market trends in Naples

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$568K
$19K
MoM
Sale-to-List Price
95.2%
0.1%
MoM
Price per sq ft
$330
$0
MoM
Available listings
5204
766
MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$147,351
Assessment$21,542,413
Home facts updated by county records

Comparable Sales for 4255 Gordon Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.60
Single-Family Home
$7,200,000
10/27/25
4
3
2,755
0.81
Single-Family Home
$8,900,000
12/29/25
4
5
3,568
0.23
Single-Family Home
$10,950,000
07/29/26
4
4.5
5,416
0.16
Single-Family Home
$25,000,000
02/25/26
6
7
6,291
0.73
Single-Family Home
$8,550,000
04/30/26
6
6
4,584
0.80
Single-Family Home
$6,075,000
12/17/25
4
5.5
5,935
0.61
Single-Family Home
$15,900,000
05/11/26
5
5.5
6,816
1.17
Single-Family Home
$6,300,000
10/23/25
3
3.5
3,098
0.35
Single-Family Home
$36,500,000
07/22/26
6
7
9,074
0.62
Single-Family Home
$20,500,000
08/29/25
5
7
7,751

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 4255 Gordon Dr.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

What Locals Say about Port Royal

At least 4 Trulia users voted on each feature.
  • 100 % Say parking is easy

  • 100 % Say it's dog friendly

  • 100 % Say people would walk alone at night

  • 100 % Say car is needed

  • 78 % Say it's quiet

  • 75 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 50 % Say yards are well-kept

  • 43 % Say there's wildlife

  • 39 % Say neighbors are friendly

  • 25 % Say streets are well-lit

  • 17 % Say it's walkable to restaurants

  • 17 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Eurobaby
    "I've done a fair amount of travel throughout the US-but never have I found a more perfectly planned and aesthetically pleasing place. Whether you're young, middle-aged, senior, living w/ children or empty nester, it just doesn't get much better than this on planet earth. "

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

Explore by feature - Garage

Explore by feature - Air Conditioning

Explore by feature - Pool

Explore by feature - Washer/dryer

Explore by feature - Outdoor Space

Homes for sale near 4255 Gordon Dr

Skip to last item
Skip to first item

Off Market Homes Near 4255 Gordon Dr

Skip to last item
Skip to first item