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$4,400,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 2,555 Sq. Ft.

Next open house:

Open House: 1:00 PM - 4:00 PM

Saturday 1/17 1:00 PM - 4:00 PM

1550 Chesapeake Ave,Naples, FL 34102

1550 Chesapeake AveNaplesFL34102

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Experience waterfront living in this stunning four-bedroom ranch-style residence offering direct, deep-water Gulf access and exceptional privacy. This high and dry property has never experience any storm flooding or damage. Positioned with desirable southern exposure, the home captures tranquil views of lush mangroves and picturesque boat docks, creating a serene Naples backdrop. A highlight of the property is the expansive 1,000-square-foot private dock, ideal for boating enthusiasts, sunset lounging or hosting unforgettable gatherings by the water. Inside, the home features a gourmet kitchen designed to impress, complete with a spectacular 14 foot custom island, premium finishes, and seamless flow for everyday living or entertaining. The elegant dining room includes an integrated built-in bar, offering a sophisticated space for hosting friends and family. Additional features include a three-car garage, spacious bedrooms, and an inviting single-level layout that embodies comfort and coastal ease. Just minutes from 5th Avenue's renowned shops and fine dining, this home offers the ideal blend of luxury, convenience and waterfront charm. A must-see for those seeking exceptional Naples living.

Full Property Details for 1550 Chesapeake Ave

General

  • Price: $4,400,000
  • Taxes: (2024)
  • Status: Active
  • Type: Single Family
  • Source: Bonita_Springs
  • MLS ID: 225079832
  • Updated: 12/8/2025
  • Added to Site: 45 day(s) ago

Interior

  • Interior Features: Split Bedrooms, Bar, Built-In Cabinets, Wired for Data, Pantry
  • Appliances: Gas Cooktop, Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator/Freezer, Washer
  • Furnishings: Unfurnished
  • Flooring: Wood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4
  • Primary Bathroom: Dual Sinks, Shower Only

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Kitchen: Kitchen Island, Pantry
  • Dining Room: Breakfast Bar, Dining - Family
  • Laundry: Washer/Dryer Hookup, Inside

Additional Information

  • Shared Amenities: None, Boating
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Electric Heat, Salt Water
  • Security/Safety: Smoke Detector(s), Smoke Detectors
  • Equipment: Air Purifier

Exterior

  • Exterior Features: Dock, Boat Lift, Elec Avail at dock, Water Avail at Dock, Wooden Dock, Automatic Sprinkler
  • Porch/Patio/Deck: Open Porch/Lanai, Deck

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: Garage Door Opener, Attached

Location

  • Area: NA08 - Royal Harbor-Windstar Are
  • County: Collier
  • Subdivision: OYSTER BAY
  • Building Name: OYSTER BAY
  • Direction Faces: North

Community

  • Assoc. Fees Include: None
  • Units Assoc/Comm: 1
  • Pets Allowed: Yes
  • Management Type: None

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Ceiling Fan(s)
  • Heating Type: Central Electric

Utilities

  • Gas: Propane
  • Sewer: Central
  • Water: Central
  • Cable Available: Yes
  • Utility Description: Propane, Cable Available, Natural Gas Available

Structural Information

  • Description/Design: Single Family Residence
  • Exterior Const.: Concrete Block, Stucco
  • Roof: Tile
  • Windows: Impact Resistant, Single Hung, Sliding, Impact Resistant Windows
  • Doors: Impact Resistant Doors
  • Entry Floor Number: 1
  • Stories/Levels: 1
  • Stories in Building: 1
  • Square Feet: 2,555
  • Sq. Ft. Source: Property Appraiser Office
  • Living Area: 2,555 Sq. Ft.
  • Year Built: 1991

Lot Features

  • Property View: Canal
  • Lot Size Source: Property Appraiser Office
  • Irrigation System: Central
  • Lot Features: Regular
  • Lot Description: Regular

Water Features

  • Water Front: Yes
  • Gulf Access: Yes
  • Water Front Desc.: Canal Front
  • Canal Width: Canal Width 81-120
  • Boat Dock Slip: Yes

Financial Considerations

  • Tax Year: 2024
  • Terms: Buyer Finance/Cash

Disclosures and Reports

  • Ownership: Single Family
  • Legal Description: OYSTER BAY UNIT 5 LOT 5
  • Property ID: 15350200008
  • Section: 10
  • Lot Number: 5

Listed by Premier Sotheby's Int'l Realty

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— 1550 Chesapeake Ave —

  • Premier Sotheby's Int'l Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1550 Chesapeake Ave

School District:Collier County School District
NameGradesDistance
Lake Park Elementary School, Naples, FL
1295 14th Avenue North, Naples, FL 34102
K-52.3 mi
Naples High School
1100 Golden Eagle Circle, Naples, FL 34102
9-122.9 mi
Gulfview Middle School
255 6th Street South, Naples, FL 34102
6-81.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1550 Chesapeake Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/02/2025
Listed
$4,400,000
120%
MLS
6/03/2021
Sold
$2,000,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1550 Chesapeake Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$18,812
2%
$2,008,881
3%
2024
$18,399
2%
$1,952,265
3%
2023
$18,107
110%
$1,895,403
126%
2021
$8,610
-49%
$838,745
-50%
2022
$16,896
96%
$1,678,553
103%
2021
$8,610
4%
$827,165
2%
2019
$8,292
-12%
$808,568
-12%
2018
$9,438
2%
$916,693
2%
2017
$9,288
-10%
$897,838
-9%
2016
$10,339
144%
$991,129
137%
2015
$4,229
—
$417,478
1%
2014
$4,241
—
$414,165
2%
2013
$4,223
—
$408,044
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Premier Sotheby's Int'l Realty

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1550 Chesapeake Ave, Naples, FL 34102 (MLS# 225079832) is a Single Family property with 4 bedrooms and 4 full bathrooms. 1550 Chesapeake Ave is currently listed for $4,400,000 and was received on December 02, 2025. Want to learn more about 1550 Chesapeake Ave? Do you have questions about finding other Single Family real estate for sale in Naples? You can browse all Naples real estate or contact a Coldwell Banker agent to request more information.

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