1066 Highlands Dr, Naples, FL 34103
Property image
Property image
OFF MARKET

$512,400

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,381 sqft

1066 Highlands Dr, Naples, FL 34103

Est. Refi. Payment $3,213/mo*
Refinance Your Home

Home Value

Trulia Estimate
$512K
Since last month
$200 (0%)
Since last year
Increased$120K (+26.5%)
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 +134% in the last 10 years
MonthEstimated value
2026
September 2026$571K
August 2026$571K
July 2026$571K
June 2026$509K
May 2026$513K
April 2026$525K
March 2026$457K
February 2026$455K
January 2026$447K
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
1097 Sperling AVE, Naples, FL
0.09
Single-Family Home
$540,000
06/12/26
3
2
1,100
1139 Michigan AVE, Naples, FL
0.16
Single-Family Home
$920,000
07/27/26
3
2
1,865
1258 Solana Rd, Naples, FL
0.16
Single-Family Home
$725,000
02/20/26
3
2
1,692
1336 Highlands DR, Naples, FL
0.23
Single-Family Home
$430,000
04/13/26
3
2
945
1060 S Alhambra Cir, Naples, FL
0.31
Single-Family Home
$420,000
02/12/26
3
2
1,327
1125 Hilltop DR, Naples, FL
0.30
Single-Family Home
$534,000
02/10/26
3
2
1,464
1324 Highlands DR, Naples, FL
0.22
Single-Family Home
$495,000
10/21/25
2
2
973
1246 Hilltop DR, Naples, FL
0.30
Single-Family Home
$440,000
10/02/25
3
2
1,080
1051 Cypress Woods Dr, Naples, FL
0.21
Single-Family Home
$717,500
04/16/26
2
2
1,360
1136 Trail Terrace DR, Naples, FL
0.10
Single-Family Home
$1,600,000
01/07/26
3
3.5
2,340

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
1025 Trail Terrace DR, Naples, FL 34103
0.05
$477,600
2
2
986
Off Market
1201 Solana RD #9, Naples, FL 34103
0.08
$278,900
2
2
1,160
Off Market
1201 Solana RD #3, Naples, FL 34103
0.10
$243,800
2
2.5
1,230
Off Market
1097 Sperling AVE, Naples, FL 34103
0.09
$540,000
3
2
1,100
Recently Sold
1210 Shady Rest LN #11, Naples, FL 34103
0.11
$328,200
2
2
1,160
Off Market
1134 Trail Terrace DR, Naples, FL 34103
0.09
$1,595,000
3
3.5
2,499
For Sale
1136 Trail Terrace DR, Naples, FL 34103
0.10
$1,600,000
3
3.5
2,340
Recently Sold
1022 Sperling AVE, Naples, FL 34103
0.13
$503,900
2
2
1,188
Off Market
3920 10th ST N, Naples, FL 34103
0.14
$798,900
4
3
1,979
For Sale
1147 Shady Rest LN, Naples, FL 34103
0.14
$510,000
3
2
1,852
Off Market
1245 Solana RD, Naples, FL 34103
0.13
$550,000
2
2
1,728
For Sale
1245 Solana RD #G-1, Naples, FL 34103
0.13
$467,200
2
2
1,728
Off Market

Local Information

  • Map ViewExplore the area around 1066 Highlands Dr.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1979
1,381 sqft
$371/sqft
Garage

About this House

The best location just steps from the Park Shore ! Single family home without any association fees . This 3/2 with garage is CBS with metal roof and remodeled with tile throughout and updated kitchen and bathrooms. No H.O.A's and fence and privacy hedge. Quiet, safe, conveniently located to the beach (less than a mile!!), Venetian Village, The Waterside Shops, Parkshore, US41, Goodlette Rd, and Pine ridge road with access to I75.
1066 Highlands Dr, Naples, FL 34103 is a 3 bedroom, 2 bathroom, 1,381 sqft single-family home built in 1979. It last sold for $0 on Apr 26, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $512,400, with a rent estimate of $3,706/month.

Home Details for 1066 Highlands Dr

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Laminate
Interior Details
Types of Rooms: Walk In Closet
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: MetalExterior: StuccoPorch
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1979Year Updated: 1977
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 6534 sqft

Price and Tax history

DateEventPrice
Sep 20, 2026
Source: MIAMI #A12005272
ListingRemoved
$539,977
Jul 18, 2026
Source: SWFLMLS #226025958
PriceChange
$584,900
Price increased by 8%
Apr 22, 2026
Source: MIAMI #A12005272
Listed For Sale
$539,977
Apr 26, 2017
Source: N/A
Sold
$0
Apr 12, 2017
Source: Agent Provided
Listed For Sale
$325,000

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

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 1066 Highlands Dr

  • What is 1066 Highlands Dr estimated to be worth?
    Trulia's estimated value for 1066 Highlands Dr in Naples, FL is $512,400.
  • What is the price history for 1066 Highlands Dr?
    1066 Highlands Dr in Naples, FL last sold in April 2017.
  • 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 1066 Highlands Dr have air conditioning?
    Yes, 1066 Highlands Dr in Naples, FL has air conditioning.
  • Does 1066 Highlands Dr have laundry facilities?
    Yes, 1066 Highlands Dr in Naples, FL has in-unit laundry.

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