1376 Chesapeake Ave, Naples, FL 34102
Property image
Property image
OFF MARKET

$415,300

Trulia Estimate
as of Sep 23, 2026
  • 2 Beds
  • 2 Baths
  • 1,218 sqft

1376 Chesapeake Ave, Naples, FL 34102

Royal Harbor

Home Highlights

Apartment
1,218 sqft
$341/sqft

Local Information

  • Map ViewExplore the area around 1376 Chesapeake Ave.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Screened lanaiTwo parking spacesSpacious second floor
Spacious second floor walk up 2 BD 2 BH with Office/Den. New stainless steel kitchen appliances, washer/dryer combo in unit, new living room/dining room carpet, screened lanai. Two parking spaces and storage unit included. Located close to Downtown, Beaches, Naples Bay, Tin City and more.

Owner pays water/sewer. Renter responsible for electric, internet, cable TV.
First and last month rent due at signing. No smoking allowed in unit. Up to 1 cat will be allowed.
1376 Chesapeake Ave, Naples, FL 34102 is a 2 bedroom, 2 bathroom, 1,218 sqft apartment in Royal Harbor. More recently, it was listed as a rental in September 2025 with an asking price of $2,500 per month. That rental listing was removed on October 27, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $415,300.

Home Details for 1376 Chesapeake Ave

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Carpet, Tile

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 1376 Chesapeake Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1055 Sandpiper St, Naples, FL
0.39
Apartment
$730,000
02/10/26
2
2
1,307 sqft
801 River Point Dr #206A, Naples, FL
0.57
Apartment
$415,000
03/27/26
2
2
1,100 sqft
1490 5th Ave S #221, Naples, FL
0.50
Apartment
$1,633,000
06/03/26
2
2
1,797 sqft
985 Sandpiper St, Naples, FL
0.39
Apartment
$975,000
06/09/26
3
2
1,769 sqft
1100 8th Ave S #211B, Naples, FL
0.60
Apartment
$490,000
10/10/25
2
2
924 sqft
676 12th Ave S, Naples, FL
0.64
Apartment
$345,500
05/06/26
2
1
865 sqft
1035 3rd Ave S #215, Naples, FL
0.97
Apartment
$1,020,000
04/30/26
2
2
1,268 sqft
221 9th St S #102, Naples, FL
1.03
Apartment
$160,540
02/17/26
2
2
1,086 sqft
950 7th Ave S #23, Naples, FL
0.68
Apartment
$460,000
10/14/25
1
1
631 sqft
229 7th Ave S #202, Naples, FL
1.16
Apartment
$1,300,000
01/23/26
3
2
1,473 sqft
Home facts updated by county records

Nearby homes

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Rental Market Trends in Royal Harbor

Last updated Sep 2026
Average rent
$5.81K
$311MoM
Available listings
39
View rental market trends in Naples, FL

Around this home

Neighborhood Overview

Royal Harbor
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Royal Harbor

At least 2 Trulia users voted on each feature.

  • 100 % Say it's quiet

  • 100 % Say car is needed

  • 100 % Say people would walk alone at night

  • 100 % Say parking is easy

  • 100 % Say yards are well-kept

  • 75 % Say there's holiday spirit

  • 67 % Say it's dog friendly

  • 53 % Say neighbors are friendly

  • 50 % Say kids play outside

  • 50 % Say they plan to stay for at least 5 years

  • 50 % Say there's wildlife

  • 33 % Say it's walkable to restaurants

  • 25 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Super nice location ! Close to beaches, downtown, everything you might want. Friendly neighbors. Close to restaurants, groceries, cafes. Beautiful homes. Historic homes "
    0
    Flag
  • Trulia User
    "It’s a great cozy quaint historic neighborhood. Close to downtown, beaches, everything Naples has to offer. Great for walking, biking. Fantastic location!"
    0
    Flag
  • Trulia User
    "Living here, is like being on vacation 24/7. Southwest Florida is a piece of paradise. It's easy living with convenient access to everything including the pristine beaches."
    0
    Flag
  • Huckbabe
    "Live in Four Winds; beautiful feeling of community! Everyone loves being there and treats it like the do!"
    0
    Flag
  • jchdwck
    "All houses are on the water. Excellent area for those interested in boating. Also close to everything - downtown shopping, beach, dining, etc."
    10
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Oct 27, 2025
Source: Zillow Rentals
ListingRemoved
$2,500
Sep 17, 2025
Source: Zillow Rentals
Listed For Rent
$2,500

Frequently asked questions about 1376 Chesapeake Ave

  • What is 1376 Chesapeake Ave estimated to be worth?
    Trulia's estimated value for 1376 Chesapeake Ave in Naples, FL is $415,300.
  • Is Naples a buyer's or seller's market?
    Naples is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Naples?
    The median sale price in Naples is $550K. That is down $18.33K from the prior month.
  • What are the closest schools to 1376 Chesapeake Ave?
    The closest schools to 1376 Chesapeake Ave 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).
  • Does 1376 Chesapeake Ave have air conditioning?
    Yes, 1376 Chesapeake Ave in Naples, FL has air conditioning.
  • Does 1376 Chesapeake Ave have laundry facilities?
    Yes, 1376 Chesapeake Ave in Naples, FL has in-unit laundry.

Homes for rent near 1376 Chesapeake Ave

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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