1399 Osprey Ave, Naples, FL 34102
Property image
Property image
OFF MARKET

$2,207,700

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,500 sqft (on 0.26 acres)

1399 Osprey Ave, Naples, FL 34102

Royal Harbor
Est. Refi. Payment $13,598/mo*
Refinance Your Home
Currently Off Market - Sold Jul 19, 2022 for $2,750,000

Home Value

Trulia Estimate
$2.21M
Since last month
Decreased$38K (-1.7%)
Since last year
Decreased$142K (-6%)
Since last sale
Decreased$542K (-19.7%)
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 +97% in the last 10 years
MonthEstimated value
2026
September 2026$2.21M
August 2026$2.25M
July 2026$2.21M
June 2026$2.25M
May 2026$2.26M
April 2026$2.3M
March 2026$2.29M
February 2026$2.31M
January 2026$2.26M
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
1515 Osprey AVE, Naples, FL
0.11
Single-Family Home
$2,500,000
03/23/26
3
2
2,131
1600 Curlew Ave, Naples, FL
0.19
Single-Family Home
$1,655,000
03/02/26
3
2
1,817
1525 OSPREY AVE, Naples, FL
0.13
Single-Family Home
$1,850,000
12/18/25
4
2
2,240
1456 Curlew AVE, Naples, FL
0.06
Single-Family Home
$5,087,500
07/15/26
4
4.5
3,607
1135 7th ST S, Naples, FL
0.60
Single-Family Home
$2,700,000
09/18/26
3
3
1,640
1506 Jewel Box AVE, Naples, FL
0.40
Single-Family Home
$3,580,000
06/24/26
4
3
2,777
1650 Mullet CT, Naples, FL
0.56
Single-Family Home
$2,975,000
03/09/26
3
2
2,039
2100 Curtis St, Naples, FL
0.38
Single-Family Home
$1,232,220
07/17/26
3
3
2,376
1460 Jewel Box AVE, Naples, FL
0.39
Single-Family Home
$3,800,000
12/12/25
3
3.5
3,192
1407 Marlin DR, Naples, FL
0.63
Single-Family Home
$2,503,500
02/13/26
3
3
2,450

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
1456 Curlew AVE, Naples, FL 34102
0.06
$5,087,500
4
4.5
3,607
Recently Sold
1435 Osprey AVE, Naples, FL 34102
0.04
$6,500,000
4
3.5
3,967
For Sale
1405 Curlew AVE #3, Naples, FL 34102
0.08
$685,000
2
2
1,100
For Sale
1351 Curlew AVE #104, Naples, FL 34102
0.09
$699,999
2
2
1,022
For Sale
1351 Curlew AVE #204, Naples, FL 34102
0.09
$477,100
2
2
1,067
Off Market
1305 Curlew AVE #C, Naples, FL 34102
0.10
$1,399,000
2
3
2,170
Recently Sold
1540 5th AVE S #D-202, Naples, FL 34102
0.12
$1,950,700
3
3.5
2,340
Off Market
1540 5th AVE S #D303, Naples, FL 34102
0.12
$1,760,000
3
3.5
2,318
Recently Sold
1540 5TH AVE S #D305, Naples, FL 34102
0.12
$2,495,000
3
3.5
2,391
For Sale
1530 5th AVE S #C-208, Naples, FL 34102
0.13
$2,800,000
3
4
3,286
Recently Sold
1530 5th AVE S #C-213, Naples, FL 34102
0.13
$2,466,300
3
3.5
3,454
Off Market
1530 5th AVE S #208C, Naples, FL 34102
0.13
$2,800,000
3
4
3,286
Recently Sold

Local Information

  • Map ViewExplore the area around 1399 Osprey Ave.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1973
0.26 acre lot
1,500 sqft
$1,472/sqft
Attached Garage

About this House

Incredible opportunity to own a beautiful canal front home in desirable Golden Shores. Residence has been extensively updated. The inviting backyard provides water views overlooking the boat dock complete with slip and boat lift just feet from Naples Bay. The screened lanai provides peaceful, outdoor living with a quaint, refreshing pool. The ideal location is a boater's dream just minutes to Naples Bay and the Gulf of Mexico with no bridges. Golden Shores provides quick access to the club and amenities of Naples Bay Resort and is ideally located within biking distance from downtown 5th Avenue South's and 3rd Street South's, fine dining, world-class shopping, entertainment, and white sand beaches.
1399 Osprey Ave, Naples, FL 34102 is a 3 bedroom, 3 bathroom, 1,500 sqft single-family home in Royal Harbor, built in 1973. It last sold for $2,750,000 on Jul 19, 2022 (30% below the $3,950,000 asking price). More recently, it was listed as a rental in January 2025 with an asking price of $18,000 per month. That rental listing was removed on September 23, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,207,700.
Contact this Building
Property Website

Home Details for 1399 Osprey Ave

Property Information

Year Built
Year Built: 1973
Property Type / Style
Property Type: Single Family Home

Interior Features

Heating & Cooling
Air Conditioning

Exterior Features

Pool
Pool
Parking & Garage
GarageParking: Garage Attached, Garage Attached

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Sep 23, 2025
Source: NABOR FL #224088820
ListingRemoved
$17,500
Jul 18, 2025
Source: NABOR FL #224088820
PriceChange
$17,500
Price decreased by 3%
Feb 25, 2025
Source: NABOR FL #224088820
PriceChange
$18,000
Price increased by 140%
Feb 23, 2025
Source: NABOR FL #224103092
PriceChange
$7,500
Price decreased by 58%
Jan 11, 2025
Source: NABOR FL #224088820
Listed For Rent
$18,000

Market trends in Naples

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$550K
$18.33KMoM
Sale-to-List Price
95.0%
0.1%MoM
Price per sq ft
$323
$9MoM
Available listings
4452
376MoM

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

Frequently asked questions about 1399 Osprey Ave

  • What is 1399 Osprey Ave estimated to be worth?
    Trulia's estimated value for 1399 Osprey Ave in Naples, FL is $2,207,700.
  • What is the price history for 1399 Osprey Ave?
    1399 Osprey Ave in Naples, FL last sold for $2,750,000 in July 2022.
  • 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.
  • Does 1399 Osprey Ave have a pool?
    Yes, 1399 Osprey Ave in Naples, FL has a pool.
  • How big is the lot at 1399 Osprey Ave?
    The lot at 1399 Osprey Ave in Naples, FL is about 0.26 acres (11,326 sq ft).

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