2885 Naples Dr, Winter Park, FL 32789
Property image
Property image
OFF MARKET

$366,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,284 sqft

2885 Naples Dr, Winter Park, FL 32789

Fairview Shores
Est. Refi. Payment $2,696/mo*
Refinance Your Home
Currently Off Market - Sold Mar 14, 2014 for $150,000

Home Value

Trulia Estimate
$367K
Since last month
Increased$5K (+1.4%)
Since last year
Increased$12K (+3.4%)
Since last sale
Increased$217K (+144.7%)
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 +114% in the last 10 years
MonthEstimated value
2026
September 2026$367K
August 2026$362K
July 2026$364K
June 2026$366K
May 2026$363K
April 2026$364K
March 2026$360K
February 2026$354K
January 2026$352K
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
0.10
Single-Family Home
$360,000
10/27/25
3
2
1,398
0.12
Single-Family Home
$417,500
06/05/26
3
2
1,208
0.20
Single-Family Home
$415,000
05/01/26
3
2
1,354
0.18
Single-Family Home
$450,000
09/29/25
3
2
1,372
0.26
Single-Family Home
$390,000
04/07/26
3
2
1,365
0.20
Single-Family Home
$256,250
08/25/26
4
2
1,665
0.30
Single-Family Home
$305,000
07/23/26
3
2
1,050
0.24
Single-Family Home
$426,000
08/06/26
3
2
1,681
0.28
Single-Family Home
$398,000
05/27/26
3
2
1,299
0.14
Single-Family Home
$335,000
11/03/25
3
1
1,069

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
0.02
$522,300
4
2
1,899
Off Market
0.04
$435,000
3
2
-
Recently Sold
0.07
$396,600
3
2
1,356
Off Market
0.10
$495,000
5
3
2,194
Recently Sold
0.09
-
-
-
-
Off Market
0.10
$355,100
3
2
1,398
Off Market
0.08
$420,000
3
2
1,485
Off Market
0.11
$190,100
2
1
939
Off Market
0.11
$402,400
3
2
1,650
Off Market
0.11
$457,200
2
2
1,030
Off Market
0.12
$417,500
3
2
1,208
Recently Sold
0.16
$341,600
3
2
1,188
Off Market

Local Information

  • Map ViewExplore the area around 2885 Naples Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1957
1,284 sqft
$286/sqft
Garage

About this House

Under Contract Taking Backups - This charming 3 bedroom, 2 bathroom home is bound to be a family pleaser! Centrally located in Winter Park. Featuring a Formal Dining with a Living/Great room. Master Suite with a private bath/walk-in closet. Bonus room or 4th bedroom. Hardwood floors in living areas with ceramic tile in kitchen and baths. Large fenced back yard with screened in Lanai overlooking a large pool area. Perfect for entertaining family and friends! New Septic and Drain Field in 2011 With NO HOA this home is a MUST SEE!
2885 Naples Dr, Winter Park, FL 32789 is a 3 bedroom, 2 bathroom, 1,284 sqft single-family home in Fairview Shores, built in 1957. It last sold for $150,000 on Mar 14, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $366,800, with a rent estimate of $2,267/month.

Home Details for 2885 Naples Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Interior Details
Types of Rooms: Dining Room
Appliances & Utilities
DishwasherRefrigerator

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other
Pool
Pool
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1957Year Updated: 1980
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 8632 sqft

Price and Tax history

DateEventPrice
Mar 14, 2014
Source: Stellar MLS #O5202798
Sold
$150,000
Jan 10, 2014
Source: Agent Provided
Listed For Sale
$163,900
Aug 18, 2011
Source: N/A
Sold
$120,000

Market trends in Orlando

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$387K
$2.53K
MoM
Sale-to-List Price
98.1%
Price per sq ft
$233
$1
MoM
Available listings
4176
24
MoM

Around this home

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

Neighborhood Overview

Neighborhood stats provided by third party data sources.

What Locals Say about Fairview Shores

At least 91 Trulia users voted on each feature.
  • 81 % Say parking is easy

  • 80 % Say car is needed

  • 77 % Say yards are well-kept

  • 75 % Say it's dog friendly

  • 70 % Say it's quiet

  • 68 % Say there are sidewalks

  • 65 % Say there's holiday spirit

  • 58 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 53 % Say streets are well-lit

  • 51 % Say it's walkable to restaurants

  • 44 % Say people would walk alone at night

  • 42 % Say neighbors are friendly

  • 41 % Say they plan to stay for at least 5 years

  • 37 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Cinthya Dantas-LeBlanc
    "The house is at kingswood manor. The neighborhood is very safe and quiet. There are lots of families, children playing around, people walking their dogs and exercising. They also have a nice park with a playground, swimming pool, tennis and basketball. "
  • Trulia User
    "This neighborhood is not safe. Frequent shootings heard off in the distance, helicopters searching for people at night. It used to be quiet a few years ago but it’s going downhill."
  • Cakingston
    "Easy commute with easy access to multiple highways. Edgewater is busy at high school drop off time for both public and private school. "
  • Trulia User
    "The neighborhood has many families and is safe place, very friendly. Great shops and cafes very close."
  • Torie B.
    "car and bus as well as uber or Lyft rides when available also it is safe here where I live and reside"
  • Risa G.
    "It’s quiet even though the main roads are busy and the people who live around the area are always friendly and helpful"
  • Carolina B. B.
    "Great neighborhood, cool restaurants in The downtown, nice parks, quite. Great community. Lake is clean"
  • Temia J.
    "Quite spacious yards brick houses older neighborhood convenient neighborhood park with pool and community events "
  • Temia J.
    "I have lived here for 6 years. It’s quite and convenient to shops and major road ways. Schools are near by within walking distance."
  • Shanlyn1117
    "Nothing much to speak of. We do have community yard sales a couple times a year. I believe there is a Christmas party but I don’t go cause I am usually working."
  • Jason Al
    "The location is great. Downtown 12 mins. Maitland 7 mins. Altamonte springs 13 mins. College Park. 4 mins.The neighborhood is nice and you are pretty close to everything"
  • Jason A.
    "This neighbor hood is quiet, beautiful, safe, and the location in orlando Florida is perfect. Everything is close, downtown orlando, college park, , I4. Excellent"
  • David V.
    "I don't loke that we don't have a dog park in our area. Most people like the peace and quiet and low traffic."
  • Danny N.
    "nice neighborhood to live in... nice neighbors and pet friendly. great places to eat and shop as well"
  • Rbriana38
    "nothing this is a terrible neighborhood the security here is so rude there's trash everywhere I people here is so rude "

LGBTQ Local Legal Protections

Frequently asked questions about 2885 Naples Dr

  • What is 2885 Naples Dr estimated to be worth?
    Trulia's estimated value for 2885 Naples Dr in Winter Park, FL is $366,800.
  • What is the price history for 2885 Naples Dr?
    2885 Naples Dr in Winter Park, FL last sold for $150,000 in March 2014.
  • Is Winter Park a buyer's or seller's market?
    Winter Park is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Park?
    The median sale price in Winter Park is $387K. That is up $2.53K from the prior month.
  • Does 2885 Naples Dr have air conditioning?
    Yes, 2885 Naples Dr in Winter Park, FL has air conditioning.
  • Does 2885 Naples Dr have a pool?
    Yes, 2885 Naples Dr in Winter Park, FL has a pool.

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