369 2nd Ave N, Naples, FL 34102
Main guest room
Property image
OFF MARKET

369 2nd Ave N
Naples, FL 34102

Old Naples
  • 4 Beds
  • 4 Baths
  • 2,700 sqft

$3,908,500

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $22,936/mo*

$3,908,500

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $22,936/mo*
4 Beds
4 Baths
2,700 sqft

Local Information

  • Map ViewExplore the area around 369 2nd Ave N.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1992
Living Area
2,700 sqft
Price/Sqft
$1,448
Parking
Garage

Description

See rate sheet for price clarification - $27,500/month is for 4 - 6 month high season. Available right now through season! First time available this charming Olde Naples home is just 3 blocks from the beautiful Gulf beach and is ready for a great tenant! Very fresh, clean, comfortable and classic/casual. Quaint brick paver patio with pergola, is ideal for morning coffee. Pool, fireplace, guest apartment over the garage, with its own kitchenette. The perfect Naples retreat. Approximately 2,700 sq. ft. with 4 Bedrooms + Den and 4 Baths.
369 2nd Ave N, Naples, FL 34102 is a 4 bedroom, 4 bathroom, 2,700 sqft single-family home in Old Naples, built in 1992. It last sold for $2,600,000 on Oct 1, 2020. More recently, it was listed as a rental in July 2025 with an asking price of $43,500 per month. That rental listing was removed on July 2, 2026. It is currently off market. The Trulia Estimate is $3,908,500, with a rent estimate of $35,281/month.

Home Details for 369 2nd Ave N

Interior Features

Heating & Cooling
Heating: Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1992Year Updated: 1992
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Furnished

Exterior Features

Exterior Home Features
Deck
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price History for 369 2nd Ave N

DatePriceEventSource
07/02/2026$43,500ListingRemovedNABOR FL #225060347
07/01/2025$43,500Listed For RentNABOR FL #225060347
01/12/2021ListingRemovedNABOR FL
12/05/2020$27,500Listed For RentAgent Provided
10/01/2020$2,600,000Sold
N/A
09/05/2020$2,900,000PendingN/A
07/14/2020$2,900,000PriceChange
N/A
12/31/2019$2,675,000Listed For SaleN/A
05/30/2019$2,750,000ListingRemovedN/A
03/28/2019$2,750,000Listed For SaleN/A
10/04/2000$1,250,000Sold
N/A
06/21/2000$1,125,000Sold
N/A

Market trends in Old Naples

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$782K
$75K
MoM
Sale-to-List Price
—
Price per sq ft
$815
$3
MoM
Available listings
166
34
MoM
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Property Tax and Assessment

Year2025
Tax$28,624
Assessment$3,662,876
Home facts updated by county records

Comparable Sales for 369 2nd Ave N

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.05
Single-Family Home
$3,600,000
07/08/26
4
3.5
3,971
0.13
Single-Family Home
$6,100,000
10/15/25
4
4
3,818
0.21
Single-Family Home
$4,375,000
11/19/25
4
4
3,570
0.37
Single-Family Home
$2,650,000
09/24/25
3
3
2,029
0.22
Single-Family Home
$4,695,000
06/18/26
4
3.5
4,095
0.06
Single-Family Home
$3,600,000
11/19/25
3
2
1,521
0.29
Single-Family Home
$3,650,000
12/05/25
5
5
4,305
0.24
Single-Family Home
$6,250,000
04/27/26
4
5
4,001
0.39
Single-Family Home
$5,000,000
04/10/26
4
3.5
3,199
0.48
Single-Family Home
$3,000,000
06/03/26
3
2.5
1,983

Nearby homes

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Assigned Schools

These are the assigned schools for 369 2nd Ave N.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

What Locals Say about Old Naples

At least 49 Trulia users voted on each feature.
  • 91 % Say people would walk alone at night

  • 83 % Say it's walkable to restaurants

  • 81 % Say it's dog friendly

  • 77 % Say it's quiet

  • 76 % Say car is needed

  • 71 % Say there are sidewalks

  • 69 % Say they plan to stay for at least 5 years

  • 68 % Say there's holiday spirit

  • 66 % Say streets are well-lit

  • 65 % Say parking is easy

  • 61 % Say yards are well-kept

  • 51 % Say it's walkable to grocery stores

  • 46 % Say there are community events

  • 40 % Say neighbors are friendly

  • 35 % Say kids play outside

  • 34 % Say there's wildlife

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Old Naples is a hotspot for warm weather, beautiful beaches, great restaurants and shopping and the ARTS and tennis/pickleball nuts! A perfect place to retire."
  • Trulia User
    "I see dogs being walked daily. Dogs are friendly, well behaved and cared for. People pick up after their dogs."
  • Trulia User
    "There is live music almost every night, amazing festivals in the park, close to the beach and most restaurants."
  • Trulia User
    "Community and commercial establishments are very dog friendly…….they would not like the amount of cars on the roads"
  • Michelle
    "The town is visually beautiful. We have everything here that a large city would have in a very small town. What more could anyone ask for."
  • Mark W.
    "Olde Naples is a unique area because you have the beach so close and yet you can walk to shopping, great dining, parks and more. I sound like an advertisement for Old Naples, but it's really true!!! It doesn't get any cleaner and low crime that downtown Naples."
  • raytesta
    "We love this house and grounds. You can walk to the beach and the main street with ease. The beaches are beautiful and the whole area is cosmopolitan yest it has a small town feel. There are great restaurants localy and in the nearby Mercato shopping and nightlife area. "
  • cwagon
    "Live nearby and have visited often. Great spot to enjoy the Jul 4th fireworks from the Naples pier, just a few blocks away."

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Homes for sale near 369 2nd Ave N

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Off Market Homes Near 369 2nd Ave N

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