Beautiful Waterfront condo completely remodeled and ideally situated on the Bay, offering Gulf access with no bridges. This stunning 2/2-unit features high-end appliances, an in-unit washer and dryer, hurricane impact windows and doors, and breathtaking water views. Located just 5 minutes from downtown 5th Avenue, you'll enjoy world-class dining, shopping, entertainment, and Naples white sand beaches. An exceptional opportunity to experience the ultimate Southwest Florida waterfront lifestyle.
CondoProperty Type
1973Year Built
$302Price/Sq.Ft.
$948/moHOA Dues
Listed by Eliane Potter• Premiere Plus Realty Company
Oyster Bay, located between Naples Bay and East Naples, is a waterfront and residential Naples neighborhood with canal-lined streets and a working-marina feel. The neighborhood’s character concentrates around the Bayshore Drive S corridor near Hamilton Harbor Yacht Club, where boat yards, galleries, and low-key eateries set a salt-air rhythm. Mid-century Florida ranch homes and newer coastal builds sit behind palms, with docks and lifts shaping daily scenery. Celebration Park’s food-truck pods and live music add an after-hours pulse on the bayfront. Nearby, the Naples Botanical Garden brings curated tropical landscapes and shaded paths into the routine. Kayaks and paddleboards slip into the mangroves from local launches, keeping the water close.
Provided by Walk Score and Local Logic
Offer insights
1537 Chesapeake Ave Unit A-4 · $325,900
$323K and above
75% chance or better to win
Why $323K+ is a strong offer
DAYS ON MARKET
88 days
The average home goes pending in 114 days.
SALE-TO-LIST
93.7%
Most homes are selling 6% below list price.
About offer insights
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Interior features
Cable prewire
High-speed internet available
Multiple phone lines
Smoke detectors
Window coverings
Great room floor plan
Screened lanai/porch
Dining area within living space
Bedrooms
2 bedrooms
Master bedroom on ground level
Bathrooms
2 full bathrooms
Master bath with dual sinks and shower (no tub)
Kitchen
Dishwasher
Disposal
Microwave
Range
Self-cleaning oven
Refrigerator/ice maker
Laundry & utility
Washer and dryer included
Flooring
Tile flooring
Heating & cooling
Central electric heat
Central electric air conditioning
Ceiling fans
Exterior features
Patio
Exterior storage
Double-hung and sliding windows
Impact-resistant doors and windows
Canal view
Boat access with boat slip and wooden dock (dock lease)
Gulf access with no bridges
Canal width approximately 31–80 feet
Central irrigation
Home design
Residential unit in a low-rise (1–3) building
2-story building; unit is a corner end-unit in a garden-style apartment
Rear exposure faces northwest
Part of the Oyster Bay development (Chesapeake Landings)
Parking
1 assigned parking space
Security
Impact-resistant doors and windows (storm protection)
Construction
Concrete block construction
Stucco exterior finish
Built-up or flat roof
Originally built in 1973
Utilities
Central water
Central sewer
Cable available
HOA & community
Mandatory HOA with professional management
Quarterly HOA fee
HOA covers insurance, laundry facilities, lawn/land maintenance, exterior pest control, sewer, trash removal and water
Community amenities include common laundry, community boat slip, extra storage, sidewalks and streetlights
Community type: boating, non-gated
Financial info
Total annual recurring HOA fees listed
One-time fees may apply
Other
Part of a complex with 12 units (6 units per building); 1 unit per floor; building has 2 floors
Property restrictions: deeded, no commercial use, no RVs
Electricity and solar
View estimated energy costs and solar savings for this home
Sale and tax history for 1537 Chesapeake Ave Unit A-4
Sale History
Tax History
Date
Event
Price
NAPLESMLS #226023946
Sep 27, 2026
Pending
—
Sep 23, 2026
Price Changed
$325,900
$302/sq ft
Aug 27, 2026
Price Changed
$399,900
$370/sq ft
Aug 26, 2026
Relisted
—
Aug 19, 2026
Pending
—
Jun 24, 2026
Listed
$439,900
$407/sq ft
NAPLESMLS #225065916
Dec 4, 2025
Rental Removed
$1,900
$2/sq ft
Nov 18, 2025
Price Changed
$1,900
$2/sq ft
Oct 9, 2025
Price Changed
$2,300
$2/sq ft
Aug 6, 2025
Listed for Rent
$2,500
$2/sq ft
NAPLESMLS #224081000
Dec 31, 2025
Listing Removed
—
Nov 17, 2025
Price Changed
$449,000
$416/sq ft
Dec 21, 2024
Price Changed
$499,900
$463/sq ft
Oct 4, 2024
Listed
$599,000
$555/sq ft
NAPLESMLS #225020702
May 13, 2025
Rental Removed
$2,550
$2/sq ft
Feb 24, 2025
Listed for Rent
$2,550
$2/sq ft
NAPLESMLS #224062345
Dec 10, 2024
Rental Removed
$2,550
$2/sq ft
Sep 7, 2024
Price Changed
$2,550
$2/sq ft
Jul 28, 2024
Listed for Rent
$2,850
$3/sq ft
NAPLESMLS #224008735
Jul 24, 2024
Listing Removed
—
Jul 10, 2024
Price Changed
$599,000
$555/sq ft
May 21, 2024
Price Changed
$699,000
$647/sq ft
Mar 19, 2024
Price Changed
$749,000
$694/sq ft
Feb 12, 2024
Price Changed
$790,000
$731/sq ft
Jan 29, 2024
Listed
$825,000
$764/sq ft
NAPLESMLS #222061326
Mar 21, 2023
Sold
$430,000
$398/sq ft
Feb 27, 2023
Pending
—
Feb 23, 2023
Relisted
—
Feb 18, 2023
Pending
—
Feb 7, 2023
Price Changed
$500,000
$463/sq ft
Feb 7, 2023
Relisted
—
Oct 16, 2022
Listing Removed
—
Sep 1, 2022
Listed
$630,000
$583/sq ft
Public Records
Aug 6, 2004
Sold
$280,000
$259/sq ft
Public Records
Jun 19, 2003
Sold
$120,000
$111/sq ft
Public Records
Jan 12, 1999
Sold
$110,000
$102/sq ft
Public Records
Jun 18, 1997
Sold
$77,000
$71/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$4,088 (−0.7%)
$428,000
2024
$4,115 (+214.4%)
$428,000
2023
$1,309 (−60.0%)
2022
$3,276 (+24.5%)
2021
$2,630 (+9.8%)
2020
$2,396 (+1.4%)
$244,400
2019
$2,363 (−3.6%)
$219,560
2018
$2,452 (−4.0%)
$228,200
2017
$2,555 (+6.3%)
$242,240
2016
$2,403 (+12.9%)
$233,600
2015
$2,129 (+63.0%)
$191,200
2014
$1,306
Public record
Public record
Zoning
Beds
—
Baths
—
Stories
—
Lot width
—
Lot depth
—
Lot size
—
Year renovated
1973
Finished Sq. Ft.
1,080
Unfinished Sq. Ft.
—
Total Sq. Ft.
1,080
Year built
1973
Style
Condo/Co-op
County
Collier County
APN
05460000085
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 12, 2026.
R3-12
Multifamily District
The R3-12 district is a residential district which is designed to accommodate a mixture of single-family homes and one-, two- and three-story apartments.
Permitted uses
Include but are not limited to:
Housing-Single unit
Housing-Multiple units
Climate risks
10/10 Flood Factor
Estimated 80%+ chance of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
10/10 Heat Factor
7 days above 107° expected this year, 26 days in 30 years
10/10 Wind Factor
99% chance of strong winds in next 30 years
3/10 Air Factor
3 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Historical weather
Naples, FL • 34102
Average low and high temperatures (°F)
72
55
76
59
81
63
84
67
87
74
90
75
91
78
90
78
89
77
86
73
81
65
77
61
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
89/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.6 hrs
7.2 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 1537 Chesapeake Ave Unit A-4
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $280,000 and $590,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $280K to $590K.