2066 Timberline Dr, Naples, FL 34109
Property image
Property image
OFF MARKET

$1,063,100

Trulia Estimate
as of Sep 20, 2026
  • 4 Beds
  • 3 Baths
  • 2,364 sqft

2066 Timberline Dr, Naples, FL 34109

Home Highlights

Single-Family Home
2,364 sqft
$450/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 2066 Timberline Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

$4,000/mo for Jun-Dec
$5,000/mo for an annual rent

NO SUBLETTING ALLOWED, NO MANAGING PROPOSALS, NO AIRBNB PLEASE!

This spacious home has 3 bedrooms plus a separate room, which could be used as an office or converted into 4th bedroom to accommodate extra guests. Freshly painted and updated with new appliances. Gorgeous lake and private pool view. Split BR floorplan, laundry room, oversized 2 car garage w/extra space. Plantation blinds and additional storage space throughout the home. MBR suite offers two walk-in closets, dual sinks, frameless glass shower and jetted tub. Kitchen has custom-made cabinets w/granite countertop, built in slide out cabinet drawers. A lot of space under the roof in pool area. Saltwater pool, shower and bathroom near pool. Close to all shopping and dining. Great schools. About 10 min drive or 20 min bike ride to Vanderbilt beach.

Owner pays for internet, pool cleaning and landscaping. Renter responsible for water and electricity charges. No smoking is allowed.

Annual rental for $5k/mo is preferred. Other terms are also available. The house is partially furnished with King bed in MBR, two Queen beds, sofa and 3 TVs.

Tenant is responsible to comply with Heron Pointe HOA rules and regulations, including prior approvals and application fees.
2066 Timberline Dr, Naples, FL 34109 is a 4 bedroom, 3 bathroom, 2,364 sqft single-family home. It last sold for $880,000 on Jun 3, 2022 (17,500% above the $5,000 asking price). More recently, it was listed as a rental in March 2026 with an asking price of $5,000 per month. That rental listing was removed on April 7, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,063,100, with a rent estimate of $5,221/month.

Home Details for 2066 Timberline Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

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

Exterior Features

Pool
Pool
Parking & Garage
Parking: Attached, On Site

Comparable Sales for 2066 Timberline Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1904 Timberline DR, Naples, FL
0.17
Single-Family Home
$870,000
11/10/25
3
3
2,604 sqft
1997 Timberline Dr, Naples, FL
0.11
Single-Family Home
$765,000
11/04/25
3
2
1,963 sqft
6821 Il Regalo CIR, Naples, FL
0.28
Single-Family Home
$1,325,000
05/15/26
4
3
2,602 sqft
1930 Blackstone CIR, Naples, FL
0.17
Single-Family Home
$1,150,000
08/31/26
3
2
2,455 sqft
6821 Wellington DR, Naples, FL
0.31
Single-Family Home
$1,310,000
09/11/26
4
3
2,829 sqft
1905 Fairfax CIR, Naples, FL
0.24
Single-Family Home
$1,600,000
05/26/26
4
3
3,135 sqft
2025 Mission DR, Naples, FL
0.32
Single-Family Home
$1,491,860
09/14/26
4
3
2,686 sqft
6865 Il Regalo CIR, Naples, FL
0.31
Single-Family Home
$1,475,000
08/19/26
4
3
3,042 sqft
1909 Fairfax CIR, Naples, FL
0.22
Single-Family Home
$1,325,000
07/07/26
3
2
2,353 sqft
1923 Blackstone CIR, Naples, FL
0.20
Single-Family Home
$1,150,000
03/23/26
3
2
2,883 sqft

Nearby homes

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Rental Market Trends in Naples

Last updated Sep 2026
Trulia Rent Estimate$5,221/mo
Average rent
$5.5K
Available listings
3949
View rental market trends in Naples, FL

Around this home

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

Price and Tax history

DateEventPrice
Apr 7, 2026
Source: Zillow Rentals
ListingRemoved
$5,000
Mar 29, 2026
Source: Zillow Rentals
Listed For Rent
$5,000
May 10, 2025
Source: Zillow Rentals
ListingRemoved
$4,000
Apr 30, 2025
Source: Zillow Rentals
PriceChange
$4,000
Price decreased by 20%
Apr 23, 2025
Source: Zillow Rentals
PriceChange
$5,000
Price increased by 4%

Frequently asked questions about 2066 Timberline Dr

  • What is 2066 Timberline Dr estimated to be worth?
    Trulia's estimated value for 2066 Timberline Dr in Naples, FL is $1,063,100.
  • What is the price history for 2066 Timberline Dr?
    2066 Timberline Dr in Naples, FL last sold for $880,000 in June 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 2066 Timberline Dr have air conditioning?
    Yes, 2066 Timberline Dr in Naples, FL has air conditioning.
  • Does 2066 Timberline Dr have a pool?
    Yes, 2066 Timberline Dr in Naples, FL has a pool.

Homes for rent near 2066 Timberline 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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