$36,500,000
5 Beds
6 Baths
6,883 sqft (on 0.73 acres)
4253 Cutlass LN, Naples, FL 34102
Est. Mortgage $212,227/mo*
Get Pre-QualifiedHome Highlights
Parking
4 Car Garage
Outdoor
Patio, Deck, Pool
HOA
None
Price/Sqft
$5,303
Climate Control
Central, Natural Gas & Central Air, Ceiling Fans
Listed
117 days ago
Local Information
- Map ViewExplore the area around 4253 Cutlass LN.
- Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
An exceptionally rare lot and one-half with one of the most spectacular panoramic views in all of Port Royal. this exceptional waterfront estate offers 147 feet along one of the area’s deepest yacht basins, on no-wake waterfront with bay views —ideal for serious boating enthusiasts. The residence features 5 spacious bedrooms, each with its own ensuite bath, along with two additional half baths for guests. Designed for both comfort and entertaining, the home includes a private study, a dedicated media room, and expansive living spaces filled with natural light. Car collectors will appreciate the four-bay garage, thoughtfully designed with lift capabilities to maximize capacity. Owners are eligible for membership to the exclusive Port Royal Club and Cutlass Cove Beach Club, offering access to one of Naples’ most private beachfront experiences. This is a unique opportunity to own a premier property combining scale, location, and deep-water access in one of Naples’ most sought-after communities.
Last check for updates: about 5 hours ago
Listing courtesy of Bill Earls, PA, (239) 777-6622
John R Wood Properties
Larry Lappin, Jr., (239) 571-8247
John R Wood Properties
Originating MLS: Naples
Source: SWFLMLS, MLS#226016944
Also Listed on SWFLMLS.
Home Details for 4253 Cutlass LN
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Interior Details Number of Rooms: 2Types of Rooms: Bedroom, Dining RoomWet Bar |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 7Number of Bathrooms (full): 5Number of Bathrooms (half): 2 |
Dimensions and Layout Living Area: 6883 Square Feet |
Appliances & Utilities Appliances: Gas Cooktop, Dishwasher, Disposal, Dryer, Freezer, Microwave, OtherDishwasherDisposalDryerLaundry: Inside,Laundry TubMicrowave |
Heating & Cooling Heating: Central,Natural GasHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Central |
Fireplace & Spa Spa: In GroundNo FireplaceHas a Spa |
Gas & Electric Gas: Propane |
Windows, Doors, Floors & Walls Window: Skylight(s), Thermal, Storm Protection (Other)Flooring: Tile, Wood |
Levels, Entrance, & Accessibility Stories: 2Number of Stories: 2Levels: TwoFloors: Tile, Wood |
View Has a ViewView: Basin, Canal |
Security Security: Smoke Detector(s) |
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Exterior Home Features Roof: TilePatio / Porch: Deck, PatioExterior: Dock, Balcony, Outdoor Shower, Boat Lift, Elec Avail at dock, Hoist/Davit, Water Avail at DockFoundation: Concrete BlockHas a Private Pool |
Parking & Garage Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas an Attached GarageParking Spaces: 4Parking: Attached |
Pool Pool: In GroundPool |
Frontage WaterfrontWaterfront: Basin, Canal FrontOn Waterfront |
Farm & Range Not Allowed to Raise Horses |
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Days on Market: 117 |
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Year Built Year Built: 1998 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: House |
Building Building: DSL/Cable AvailableConstruction Materials: Block, StuccoNot a New Construction |
Property Information Parcel Number: 16860880001 |
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Price List Price: $36,500,000Price Per Sqft: $5,303 |
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MLS Status: Active |
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Direction & Address City: NAPLESCommunity: PORT ROYAL |
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Listing Agent Listing ID: 226016944 |
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Building Area Building Area: 10847 Square Feet |
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Community Features: Boating, Non-GatedNot Senior Community |
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Association for this Listing: NaplesNo HOAHOA Fee: No HOA Fee |
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Lot Area: 0.73 acres |
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Mls Number: 226016944Water ViewWater View: Basin, CanalAttribution Contact: 239-777-6622 |
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HOA Amenities: Beach Club Available,Private Beach Pavilion,Private Membership,See RemarksSource Internet Entire Listing Display |
Around this home
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.
Market trends in Naples
Last updated July 2026
Avg. sale price
$568K
Sale-to-List Price
95.2%
Price per sq ft
$331
$1MoM
Available listings
4813
415MoM
Home Value
Trulia Estimate
$31.8MSince last month
Increased$199K (+0.6%)Since last year
Increased$16M (+108.6%)Since last sale
Increased$30M (+1,818.1%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +201% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $31.65M |
| July 2026 | $31.45M |
| June 2026 | $31.76M |
| April 2026 | $15.34M |
| March 2026 | $15.06M |
| February 2026 | $15.99M |
| January 2026 | $14.18M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.12 | Single-Family Home | $25,000,000 | 02/25/26 | 6 | 7 | 6,291 | |
0.52 | Single-Family Home | $15,900,000 | 05/11/26 | 5 | 5.5 | 6,816 | |
0.43 | Single-Family Home | $40,000,000 | 04/13/26 | 5 | 6 | 11,559 | |
0.37 | Single-Family Home | $36,500,000 | 07/22/26 | 6 | 7 | 9,074 | |
0.55 | Single-Family Home | $20,500,000 | 08/29/25 | 5 | 7 | 7,751 | |
0.65 | Single-Family Home | $8,550,000 | 04/30/26 | 6 | 6 | 4,584 | |
0.69 | Single-Family Home | $28,250,000 | 04/21/26 | 5 | 7 | 7,835 | |
0.68 | Single-Family Home | $13,000,000 | 03/16/26 | 6 | 7.5 | 8,044 | |
0.23 | Single-Family Home | $10,950,000 | 07/29/26 | 4 | 4.5 | 5,416 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.05 | $55,000,000 | 6 | 10.5 | 15,309 | Recently Sold | |
0.12 | $25,000,000 | 6 | 7 | 6,291 | Recently Sold | |
0.11 | $14,338,400 | 6 | 6.5 | 7,964 | Off Market | |
0.18 | $12,485,000 | 4 | 6.5 | 7,454 | Off Market | |
0.23 | - | 3 | 3 | 2,544 | Off Market | |
0.23 | $10,950,000 | 4 | 4.5 | 5,416 | Recently Sold | |
0.28 | - | 6 | 6.5 | 6,044 | Off Market | |
0.27 | $8,251,400 | 3 | 2 | 3,091 | Off Market | |
0.23 | $800,000 | - | - | - | Recently Sold | |
0.30 | $24,430,500 | 5 | 6 | 7,640 | Off Market | |
0.24 | $3,812,000 | - | - | - | Off Market |
Price and Tax history
| Date | Event | Price |
|---|---|---|
May 2, 2026 Source: SWFLMLS #226016944 | Listed For Sale | $36,500,000 |
Apr 14, 1995 Source: N/A | Sold | $1,650,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $119,187 | $13,727,329 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Bill Earls, PA, John R Wood Properties
Agent Phone: (239) 777-6622
The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS. Copyright 2026 Southwest Florida MLS. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.
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Frequently asked questions about 4253 Cutlass LN
- What is the estimated monthly payment for 4253 Cutlass LN?Based on a $36,500,000 list price with 20% down at today's rates, the estimated monthly payment for 4253 Cutlass LN in Naples, FL is approximately $217,942 (about $188,363 principal & interest, $29,504 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- How does the list price for 4253 Cutlass LN compare to homes in Naples?4253 Cutlass LN in Naples, FL is listed at $36,500,000, about 6322% above the $568K median sale price in Naples.
- What are the closest schools to 4253 Cutlass LN?The closest schools to 4253 Cutlass LN in Naples, FL are Gulfview Middle School (rated 9/10), Lake Park Elementary School (Pre-K, rated 10/10), Naples High School (Pre-K, rated 6/10).
- What is 4253 Cutlass LN estimated to be worth?Trulia's estimated value for 4253 Cutlass LN in Naples, FL is $31,775,100.
- Does 4253 Cutlass LN have air conditioning?Yes, 4253 Cutlass LN in Naples, FL has air conditioning.
- Does 4253 Cutlass LN have a pool?Yes, 4253 Cutlass LN in Naples, FL has a pool.
4253 Cutlass LN, Naples, FL 34102 is a 5 bedroom, 7 bathroom, 6,883 sqft single-family home built in 1998. 4253 Cutlass LN is located in Port Royal, Naples. This property is currently available for sale and was listed by SWFLMLS on May 2, 2026. The MLS # for this home is MLS# 226016944.