5376 Whitten Dr, Naples, FL 34104
Property image
Property image
OFF MARKET

$415,500

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,386 sqft

5376 Whitten Dr, Naples, FL 34104

Est. Refi. Payment $2,620/mo*
Refinance Your Home
Currently Off Market - Sold Aug 26, 2014 for $209,900

Home Value

Trulia Estimate
$416K
Since last month
Decreased$4K (-0.9%)
Since last year
Decreased$3K (-0.7%)
Since last sale
Increased$204K (+97.3%)
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 +54% in the last 10 years
MonthEstimated value
2026
September 2026$414K
August 2026$418K
July 2026$416K
June 2026$416K
May 2026$414K
April 2026$416K
March 2026$417K
February 2026$424K
January 2026$421K
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
5441 Whitten DR #108, Naples, FL
0.10
Single-Family Home
$350,000
01/12/26
3
2
1,386
5441 Whitten Dr, Naples, FL
0.10
Single-Family Home
$350,000
01/14/26
3
2
1,400
5474 Whitten DR #12, Naples, FL
0.15
Single-Family Home
$480,000
07/09/26
2
2
1,386
5433 Whitten DR #106, Naples, FL
0.09
Single-Family Home
$410,000
01/08/26
3
2
1,386
5433 Whitten Dr, Naples, FL
0.09
Single-Family Home
$410,000
01/08/26
3
2
1,400
1178 Jardin DR, Naples, FL
0.24
Single-Family Home
$480,000
04/13/26
2
2
1,604
106 Oceans Blvd, Naples, FL
0.46
Single-Family Home
$235,000
12/03/25
2
2
1,722
318 Leawood CIR, Naples, FL
0.34
Single-Family Home
$235,000
02/17/26
3
2
1,080
932 Marblehead DR, Naples, FL
0.26
Single-Family Home
$459,000
07/01/26
2
2
1,320
920 Marblehead DR #K2, Naples, FL
0.27
Single-Family Home
$450,000
04/15/26
2
2
1,427

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
5356 Whitten DR #37, Naples, FL 34104
0.04
$381,900
3
2
1,386
Off Market
5446 Whitten DR #19, Naples, FL 34104
0.10
$439,000
3
2
1,400
For Sale
5433 Whitten DR #106, Naples, FL 34104
0.09
$410,000
3
2
1,386
Recently Sold
5441 Whitten DR #108, Naples, FL 34104
0.10
$350,000
3
2
1,386
Recently Sold
5717 Lago Villaggio WAY, Naples, FL 34104
0.14
$625,000
3
2
1,897
Recently Sold
1140 Moon Lake DR, Naples, FL 34104
0.08
-
3
2
2,023
Off Market
5725 Lago Villaggio WAY, Naples, FL 34104
0.15
$745,000
3
2
2,309
Recently Sold
1100 Moon Lake DR, Naples, FL 34104
0.11
$550,600
3
2
1,753
Off Market
1090 Moon Lake DR, Naples, FL 34104
0.12
$491,000
3
2
1,568
Off Market
5474 Whitten DR #12, Naples, FL 34104
0.15
$480,000
2
2
1,386
Recently Sold
5520 Whitten Dr #3, Naples, FL 34104
0.16
$420,300
3
2
1,386
Off Market
5801 Lago Villaggio WAY, Naples, FL 34104
0.17
$900,000
4
3
2,742
Recently Sold

Local Information

  • Map ViewExplore the area around 5376 Whitten Dr.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1998
1,386 sqft
$300/sqft

About this House

Property approved for HomePath and HomePath Renovation Financing with as little as 5% down-payment. The seller has directed that all offers on this listing must be made via the HomePath website. Agents, please see confidential remarks for additional information. Attached villa pool home in Whittenberg with a double-car garage. Two bedrooms, two full baths plus a den - den as a closet and can be used as a third bedroom. Large pool, screened-in lanai and an open floor plan. Vaulted ceilings with white cabinets in the kitchen and baths. Small community located just off Davis Boulevard. Close proximity to Olde Naples shopping, dining, Naples Community Hospital and to the beaches.
5376 Whitten Dr, Naples, FL 34104 is a 2 bedroom, 2 bathroom, 1,386 sqft single-family home built in 1998. It last sold for $209,900 on Aug 26, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $415,500, with a rent estimate of $2,392/month.

Home Details for 5376 Whitten Dr

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
Types of Rooms: Dining Room

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other, Cement ConcretePatio
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 1998Year Updated: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 2

Lot Information

Lot Area: 5227 sqft

Price and Tax history

DateEventPrice
Aug 26, 2014
Source: N/A
Sold
$209,900
May 10, 2014
Source: Agent Provided
Listed For Sale
$217,500
Jan 24, 2012
Source: N/A
Sold
$7,400
Dec 22, 1998
Source: N/A
Sold
$155,600

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

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Naples

At least 1698 Trulia users voted on each feature.

  • 86 % Say it's dog friendly

  • 83 % Say car is needed

  • 78 % Say parking is easy

  • 75 % Say it's quiet

  • 69 % Say people would walk alone at night

  • 69 % Say there's holiday spirit

  • 67 % Say there are sidewalks

  • 62 % Say yards are well-kept

  • 61 % Say streets are well-lit

  • 60 % Say they plan to stay for at least 5 years

  • 53 % Say neighbors are friendly

  • 51 % Say there's wildlife

  • 48 % Say kids play outside

  • 47 % Say it's walkable to grocery stores

  • 46 % Say it's walkable to restaurants

  • 39 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Silvia Polgati
    "Is a quiet neighborhood we really enjoy "
    0
    Flag
  • Mfontaine21
    "Many community events at our town center including food trucks, swim and dance parties and weekly bingo"
    0
    Flag
  • Jeff W
    "What an awesome community. From the beach, to the restaurants, the berm, the amenities, people … just love Pelican Bay. "
    1
    Flag
  • Trulia User
    "Safe neighborhoods but be wary of some of the complexes as you move east. Naples is amazing if you do your homework "
    1
    Flag
  • Swatson645
    "There is so much space to walk your dog on nice sidewalks."
    0
    Flag
  • Chad Roberson
    "Quiet, people leave you alone here. No hoa, can expand on your property. Weather is amazing 6-8 months out of the year. You’ll see amazing wildlife everywhere in this area. "
    0
    Flag
  • Jimandhelensimon
    "We have an excellent location to access numerous beaches and have an enormous amount of well landscaped green space. Our pool feels like a resort pool."
    0
    Flag
  • Jarek Przada
    "Bingo, pool gymnastics, potluck, every holiday is celebrated in the community. There are pool parties and grill dinners."
    0
    Flag
  • Jimandhelensimon
    "This is more of a senior community. There are not many families with children here. The greater community is very family oriented."
    0
    Flag
  • James
    "lots of green space in the area and there are dog parks that also can be visited by dog owners and the place is always well groomed"
    1
    Flag
  • Sandra Decain
    "Great friendly people - love the dining access to water amazing weather. Could not ask for more. "
    0
    Flag
  • Michael.mccann
    "Lovely and quiet. Great location with beach and shopping/dining nearby. Homes are well maintained "
    0
    Flag
  • Michelle SanFillipo
    "Great dog parks and open spaces for recreational activities. Safe and secure. Well lit at night. Wide sidewalks and others are respectful of dogs and clean up."
    1
    Flag
  • Cristiano Machado
    "Friendly and safe neighborhood Close to schools, lhospital and grocery stores plus great restaurants and pubs"
    0
    Flag
  • Lisa Ethier
    "Everyone would love living in my neighborhood it’s beautiful. It’s family oriented. Everyone gets along with everyone."
    0
    Flag
  • Brian.bird
    "Fun people and safe gated community with golf and tennis and good food. Homes are nice and the grounds are well kept"
    0
    Flag
  • waterman46
    "Pet friendly all dogs on leashes . We have never had a problem and 99% pick up after their dogs. Just a really nice pet friendly area."
    1
    Flag
  • Jimandhelensimon
    "It’s dog friendly but dogs must be on a leash. The dogs must be twenty pounds or less unless they are an emotional support dog."
    0
    Flag
  • DonnaT
    "Naples is a great place to retire. It is paradise. The cost of living is outrageous but it is worth every penny! "
    0
    Flag
  • Wheeler04
    "The Isles is surrounded by nature with 1/2 of its 2,400 acres dedicated to preserve and waterways. Such a friendly and active community! "
    0
    Flag
  • Airwavessystem
    "I great community to live close to everything shops supermarkets and the beach. 15 minutes to the mall and 5 minutes to the main highway 75 to tampa Orlando or to miami."
    0
    Flag
  • Scottjohnnewhouse
    "I’ve lived in Naples for 33 years. It is growing at an alarming rate but it is such a safe place to live…."
    0
    Flag
  • Trulia User
    "Everyone in Naples is very kind and friendly. The crime rate is very low. It’s a very family friendly city. "
    0
    Flag
  • Eric
    "There are a lot of young families with children out playing with each other. The community center is well equipped with gym equipment and a beautiful pool."
    0
    Flag
  • Oditth Ricardo
    "Peaceful and safe. No issues and no problems most of the time. Great schools. Great place to start a family and raise kids. "
    0
    Flag
  • Jimandhelensimon
    "Beautiful open spaces and amenities. Beaches and large variety of restaurants and entertainment. The shopping is awesome and the people are fun loving."
    0
    Flag
  • Laurel
    "This is a family friendly neighborhood. It is close to the beach, the Greenway, the zoo, parks, theater, shopping, and dining. It’s close to downtown Naples and just a few miles to The Mercato. "
    0
    Flag
  • Nmarranca
    "I am here on vacation and it is a wonderful community. We are in Beachwalk, which is very close to the beach and walking distance and we have a big pool."
    0
    Flag
  • Kldaniel29
    "Family neighborhood great place laid back great schools nice place to live but pretty hot. Only set back"
    0
    Flag
  • Twalkercillins
    "Mostly retirees. Not a lot of children. Would not recommend for families with young children. Not very walkable."
    0
    Flag
  • Mccartneyjosh
    "It is a standard city commute with lengthy traffic lights and moderate to heavy traffic, but generally it is a normal commute "
    0
    Flag
  • Amolter
    "Lake park is close to everything anyone would want. Mall, restaurants, parks, dog park, hospital, grocery store, zoo, move theatre,downtown, boat launch to the bay, and the beach!!"
    0
    Flag
  • Blondbasket
    "Great groups of people live in the area. Everything is relatively easy and close to the house. I know my neighbors and they are so far very helpful and all around happy people. "
    0
    Flag
  • Kim
    "Activities are organized by HOA director they always have lots of activities planned lots of fun "
    0
    Flag
  • Swatson645
    "Very convenient to major roads and businesses but quiet neighborhoods. Love this area! Just beautiful!!!"
    0
    Flag
  • Juntig5
    "Naples is a lovely place, tends to get crowded in the season, nice beaches and the city is clean with lots of restaurants. Pleasant weather. "
    0
    Flag
  • Jkgc11
    "There are Lots of community parks and activities for children. Miles of bike paths. Near the beach. "
    0
    Flag
  • Trulia User
    "Close to the beaches restaurant downtown feel like you on vacation family friendly and pet friendly neighborhood. Very clean and safe. Beautiful area "
    0
    Flag
  • 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
    "Easy commute. Beautiful area to live in. Lovely people, friendly, helpful, very neighborly and close to everything."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5376 Whitten Dr

  • What is 5376 Whitten Dr estimated to be worth?
    Trulia's estimated value for 5376 Whitten Dr in Naples, FL is $415,500.
  • What is the price history for 5376 Whitten Dr?
    5376 Whitten Dr in Naples, FL last sold for $209,900 in August 2014.
  • 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 5376 Whitten Dr have air conditioning?
    Yes, 5376 Whitten Dr in Naples, FL has air conditioning.
  • How big is the lot at 5376 Whitten Dr?
    The lot at 5376 Whitten Dr in Naples, FL is about 0.12 acres (5,227 sq ft).

Explore by feature - Pet Friendly

357 pet-friendly rentals in Naples, FL

Explore by feature - Garage

2012 rentals with a garage in Naples, FL

Explore by feature - Air Conditioning

3031 rentals with air conditioning in Naples, FL

Explore by feature - Pool

3262 rentals with a pool in Naples, FL

Explore by feature - Washer/dryer

3261 rentals with a washer/dryer in Naples, FL

Explore by feature - Outdoor Space

195 rentals with an outdoor space in Naples, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 5376 Whitten Dr

Skip to last item
Skip to first item

Homes for sale near 5376 Whitten Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item