5355 Whitten Dr, Naples, FL 34104
Property image
Property image
OFF MARKET

$378,700

Trulia Estimate
as of Sep 3, 2026
  • 3 Beds
  • 2 Baths
  • 1,386 sqft
  • 3 Beds
  • 2 Baths
  • 1,386 sqft

5355 Whitten Dr, Naples, FL 34104

Home Highlights

Property Type
Single-Family Home
Living Area
1,386 sqft
Price/Sqft
$273
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 5355 Whitten Dr.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

FULLY FURNISHED - READY TO MOVE IN

Discover the perfect blend of comfort, convenience, and style in this fully furnished, recently renovated home nestled within a quiet, gated community. This move-in-ready gem boasts modern upgrades, including sleek countertops, updated appliances, and elegant finishes throughout.

Located just minutes from public transit, top-rated dining, shopping centers, and popular local attractions, this home offers the ideal balance of tranquility and accessibility. Enjoy exclusive community amenities, beautifully maintained surroundings, and a secure, peaceful environment.

Whether you're looking for a turnkey residence or a stylish retreat close to everything, this home is a must-see! Contact us today for a private showing. Owner does not live on-site.

Owner is willing to negotiate utilities and include those cost into rent.
5355 Whitten Dr, Naples, FL 34104 is a 3 bedroom, 2 bathroom, 1,386 sqft single-family home. It last sold for $398,000 on Oct 7, 2022 (12,338% above the $3,200 asking price). More recently, it was listed as a rental in July 2025 with an asking price of $4,500 per month. That rental listing was removed on August 7, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $378,700, with a rent estimate of $2,752/month.

Home Details for 5355 Whitten Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Interior Features

Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central Air

Exterior Features

Pool
Pool
Parking & Garage
Parking: Attached, On Site

Comparable Sales for 5355 Whitten Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5313 Whitten Dr, Naples, FL
0.05
Single-Family Home
$450,000
06/18/26
3
2
1,400 sqft
5433 Whitten DR #106, Naples, FL
0.13
Single-Family Home
$410,000
01/08/26
3
2
1,386 sqft
5433 Whitten Dr, Naples, FL
0.13
Single-Family Home
$410,000
01/08/26
3
2
1,400 sqft
5441 Whitten DR #108, Naples, FL
0.14
Single-Family Home
$350,000
01/12/26
3
2
1,386 sqft
5441 Whitten Dr, Naples, FL
0.14
Single-Family Home
$350,000
01/14/26
3
2
1,400 sqft
5520 Whitten Dr #3, Naples, FL
0.21
Single-Family Home
$415,000
11/12/25
3
2
1,386 sqft
1175 Moon Lake DR, Naples, FL
0.14
Single-Family Home
$460,000
03/03/26
3
2
1,575 sqft
1115 Moon Lake DR, Naples, FL
0.15
Single-Family Home
$560,000
05/18/26
3
2
1,779 sqft
5474 Whitten DR #12, Naples, FL
0.19
Single-Family Home
$480,000
07/09/26
2
2
1,386 sqft
5572 Lago Villaggio WAY, Naples, FL
0.19
Single-Family Home
$560,000
10/07/25
3
2
1,784 sqft

Nearby homes

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Rental Market Trends in Naples

Last updated Sep 2026
Trulia Rent Estimate$2,752/mo
Average rent
$5.5K
$250MoM
Available listings
3987
View rental market trends in Naples, FL

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.
  • 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. "
    0
    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 "
    0
    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
  • Kim
    "Very well kept sidewalks and community areas, yards are well maintained it’s so easily accessible to markets and stores very easy to walk around , biking is also easy to do there are nice friendly people "
    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

Price and Tax history

DateEventPrice
Aug 7, 2025
Source: NABOR FL #225064128
ListingRemoved
$4,500
Jul 21, 2025
Source: NABOR FL #225064128
Listed For Rent
$4,500
Apr 23, 2025
Source: Zillow Rentals
ListingRemoved
$3,200
Apr 3, 2025
Source: Zillow Rentals
PriceChange
$3,200
Price decreased by 6%
Mar 21, 2025
Source: Zillow Rentals
PriceChange
$3,400
Price decreased by 6%

Frequently asked questions about 5355 Whitten Dr

  • What is 5355 Whitten Dr estimated to be worth?
    Trulia's estimated value for 5355 Whitten Dr in Naples, FL is $378,700.
  • What is the price history for 5355 Whitten Dr?
    5355 Whitten Dr in Naples, FL last sold for $398,000 in October 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 $568K. That is roughly unchanged from the prior month.
  • Does 5355 Whitten Dr have air conditioning?
    Yes, 5355 Whitten Dr in Naples, FL has air conditioning.
  • Does 5355 Whitten Dr have a pool?
    Yes, 5355 Whitten Dr in Naples, FL has a pool.

Homes for rent near 5355 Whitten Dr

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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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