5885 Rolling Pines Dr, Naples, FL 34110
OFF MARKET

5885 Rolling Pines Dr
Naples, FL 34110

  • 4 Beds
  • 3.5 Baths
  • 3,486 sqft (on 0.34 acres)

$1,971,500

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $11,431/mo*
Refinance Your Home

$1,971,500

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $11,431/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,486 sqft
(on 0.34 acres)

Local Information

  • Map ViewExplore the area around 5885 Rolling Pines Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

H.9819 - Enjoy the splendor and luxury in the finishes in this fabulous property located across from The Club At The Strand. Excellent floorplan with open kitchen and family room area that spills out to the large outdoor living area and lush golf course and preserve views. Private master suite with rich built-in and dual work areas. Newly renovated master bath with travertine flooring, 3" thick Quartz countertops and dual head walk in shower. No detail left undone and every convenience at your fingertips.Eight televisions, two fireplaces and offset wet bar for easy entertaining. Gorgeous island kitchen with dramatic stove top hood and glass tiled backsplash. Enhanced landscaping with large outdoor under cover entertaining area including pool with waterfall spa spillover, and lots of space for sunning. Built-in outdoor grill and bar area with seating. Fourth bedroom currently staged as pool table room but can easily convert. Air conditioned storage in garage, One year home warranty included.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 5885 Rolling Pines Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Interior Details
Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDryerMicrowaveWasher
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Hot Tub or Spa

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: Stucco
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1999Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price History for 5885 Rolling Pines Dr

DatePriceEventSource
04/14/2021$1,300,000Sold
N/A
05/10/2016$950,000Sold
N/A
01/29/2016$995,000PriceChange
Agent Provided
01/12/2016$1,040,000PriceChange
Agent Provided
10/15/2015$1,045,000Listed For SaleAgent Provided
12/12/2011$900,000Sold
N/A
09/26/2009$1,135,000ListingRemovedAgent Provided
07/12/2009$1,135,000PriceChange
Agent Provided
07/04/2009$1,185,000Listed For SaleAgent Provided
06/11/2009$1,185,000ListingRemovedAgent Provided
05/22/2009$1,185,000Listed For SaleAgent Provided
01/12/2000$724,000Sold
N/A
01/28/1999$128,000Sold
N/A

Market trends in Naples

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$587K
$1.67KMoM
Sale-to-List Price
95.3%
Price per sq ft
$330
$3MoM
Available listings
5954
639MoM
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Property Tax and Assessment

Year2025
Tax$15,139
Assessment$1,565,011
Home facts updated by county records

Comparable Sales for 5885 Rolling Pines Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6004 Fairway CT, Naples, FL
0.50
Single-Family Home
$1,595,000
01/16/26
4
3
2,745
15949 Paseo Ln, Naples, FL
0.77
Single-Family Home
$1,200,000
07/01/25
4
3.5
3,008
6064 Fairway CT, Naples, FL
0.50
Single-Family Home
$1,330,000
03/04/26
3
2.5
2,510
15948 Paseo LN, Naples, FL
0.74
Single-Family Home
$950,000
08/01/25
4
3
3,021
6499 Waverly Green WAY, Naples, FL
0.52
Single-Family Home
$825,000
04/09/26
4
2.5
2,564
5836 Paradise Cir, Naples, FL
0.29
Single-Family Home
$950,000
05/01/26
3
2
1,947
16173 Camden Lakes CIR, Naples, FL
0.59
Single-Family Home
$999,000
01/06/26
5
4
2,918
2092 Imperial CIR, Naples, FL
0.96
Single-Family Home
$1,350,000
06/08/26
4
3.5
3,133
15533 Vallecas LN, Naples, FL
0.78
Single-Family Home
$865,000
11/10/25
4
3
2,424
16301 Camden Lakes Cir, Naples, FL
0.92
Single-Family Home
$1,300,000
06/04/26
4
3
3,078

Nearby homes

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Assigned Schools

These are the assigned schools for 5885 Rolling Pines Dr.
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 1692 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

  • 61 % Say streets are well-lit

  • 61 % Say yards are well-kept

  • 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.
  • 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
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  • 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
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  • Jarek Przada
    "Bingo, pool gymnastics, potluck, every holiday is celebrated in the community. There are pool parties and grill dinners."
    0
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  • Jimandhelensimon
    "This is more of a senior community. There are not many families with children here. The greater community is very family oriented."
    0
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  • 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
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  • Michael.mccann
    "Lovely and quiet. Great location with beach and shopping/dining nearby. Homes are well maintained "
    0
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  • 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
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  • Lisa Ethier
    "Everyone would love living in my neighborhood it’s beautiful. It’s family oriented. Everyone gets along with everyone."
    0
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  • 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
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  • 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
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  • DonnaT
    "Naples is a great place to retire. It is paradise. The cost of living is outrageous but it is worth every penny! "
    0
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  • 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
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  • 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
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  • 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
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  • Trulia User
    "Everyone in Naples is very kind and friendly. The crime rate is very low. It’s a very family friendly city. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Kldaniel29
    "Family neighborhood great place laid back great schools nice place to live but pretty hot. Only set back"
    0
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  • Twalkercillins
    "Mostly retirees. Not a lot of children. Would not recommend for families with young children. Not very walkable."
    0
    Flag
  • Askrodiana
    "The neighborhood is safe for people and dogs to walk. A lot of people do walk their pets each morning and evening. "
    1
    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
  • Jt276297
    "It’s one of the cleanest towns in the United States and has a vast number of culture with in it’s population "
    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
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  • H5hnmg992c
    "none. i like that it isn’t gated. its a friendly neighborhood and people are kind. it’s becoming more accessible to food and restaurants"
    2
    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
  • Naplesjan29
    "The school’s are excellent and close by! It’s a very safe and convenient area!!The school bus picks up here daily."
    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
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  • Trulia User
    "Easy commute. Beautiful area to live in. Lovely people, friendly, helpful, very neighborly and close to everything."
    1
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Homes for sale near 5885 Rolling Pines Dr

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Off Market Homes Near 5885 Rolling Pines Dr

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5885 Rolling Pines Dr, Naples, FL 34110 is a 4 bedroom, 4 bathroom, 3,486 sqft single-family home built in 1999. This property is not currently available for sale. 5885 Rolling Pines Dr was last sold on Apr 14, 2021 for $1,300,000. The current Trulia Estimate for 5885 Rolling Pines Dr is $1,971,500.