5299 Fairfield Dr, Crestview, FL 32536
OFF MARKET

$383,200

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 1,714 sqft (on 7 acres)

5299 Fairfield Dr, Crestview, FL 32536

Est. Refi. Payment $2,406/mo*
Refinance Your Home
Currently Off Market - Sold Oct 5, 2020 for $170,000

Home Value

Trulia Estimate
$383K
Since last month
Increased$2K (+0.4%)
Since last year
Increased$88K (+30%)
Since last sale
Increased$213K (+125.1%)
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 +96% in the last 10 years
MonthEstimated value
2026
August 2026$383K
July 2026$381K
June 2026$380K
May 2026$385K
April 2026$382K
March 2026$385K
February 2026$381K
January 2026$368K
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
2226 James Lee Blvd, Crestview, FL
0.14
Single-Family Home
$450,000
12/30/25
3
2
2,091
5210 Moore Loop, Crestview, FL
0.70
Single-Family Home
$176,200
11/06/25
4
2
1,625
2260 Tanglewood Ln, Crestview, FL
0.07
Single-Family Home
$49,200
08/04/26
2
2
924
2111 Hagood Loop, Crestview, FL
0.59
Single-Family Home
$326,000
01/26/26
4
2
2,110
5211 Moore Loop, Crestview, FL
0.71
Single-Family Home
$214,000
03/26/26
4
2
2,251
2108 Hagood Loop, Crestview, FL
0.55
Single-Family Home
$330,000
12/17/25
4
2
2,562
106 Huron Trl, Crestview, FL
0.75
Single-Family Home
$319,050
03/24/26
4
2
1,823
215 Seneca Trl, Crestview, FL
0.72
Single-Family Home
$315,000
11/20/25
4
2
2,211
953 Mayo Trl, Crestview, FL
0.70
Single-Family Home
$210,000
08/05/26
3
2
1,204
108 Huron Trl, Crestview, FL
0.77
Single-Family Home
$339,000
01/14/26
4
2
1,823

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
2226 James Lee Blvd, Crestview, FL 32536
0.14
$450,000
3
2
2,091
Recently Sold
5408 Lee Farm Blvd, Crestview, FL 32536
0.45
$336,100
4
2
2,324
Off Market
5302 Marilea Ct, Crestview, FL 32536
0.50
$389,900
4
3
2,988
For Sale
5303 Marilea Ct, Crestview, FL 32536
0.52
$348,000
4
2
2,562
Off Market
5415 Lee Farm Blvd, Crestview, FL 32536
0.53
$310,500
4
2
2,044
Off Market
2118 Hagood Loop, Crestview, FL 32536
0.55
$345,000
4
2
2,314
Off Market
2110 Hagood Loop, Crestview, FL 32536
0.55
$411,000
4
3
2,950
Off Market
2108 Hagood Loop, Crestview, FL 32536
0.55
$330,000
4
2
2,562
Recently Sold
5308 Marilea Ct, Crestview, FL 32536
0.55
$263,200
4
2
1,752
Off Market
5422 Lee Farm Blvd, Crestview, FL 32536
0.56
$307,400
4
2
2,402
Off Market
236 Seneca Trl, Crestview, FL 32536
0.58
$47,500
-
-
-
For Sale
2111 Hagood Loop, Crestview, FL 32536
0.59
$326,000
4
2
2,110
Recently Sold

Local Information

  • Map ViewExplore the area around 5299 Fairfield Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1948
Lot Size
7 acres
Living Area
1,714 sqft
Price/Sqft
$224
Parking
Garage

About this House

This single-family home is located at 5299 Fairfield Dr, Crestview, FL. 5299 Fairfield Dr is in Crestview, FL and in ZIP code 32536. This property has 4 bedrooms, 3 bathrooms and approximately 1,714 sqft of floor space. This property has a lot size of 7.00 acres and was built in 1948.
5299 Fairfield Dr, Crestview, FL 32536 is a 4 bedroom, 3 bathroom, 1,714 sqft single-family home built in 1948. It last sold for $170,000 on Oct 5, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $383,200, with a rent estimate of $2,188/month.

Home Details for 5299 Fairfield Dr

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1Floors: Linoleum Vinyl
Interior Details
Types of Rooms: Master Bath, Office, Pantry, Workshop
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: MetalExterior: BrickLawnPatioPorch
Parking & Garage
GarageParking: Carport, Garage Detached, Off Street

Property Information

Year Built
Year Built: 1948Year Updated: 1948
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 7.00 acres

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
Apr 21, 2024
Source: ECAOR #938907
Pending
$325,000
Apr 18, 2024
Source: ECAOR #938907
PriceChange
$325,000
Price decreased by 8%
Apr 11, 2024
Source: ECAOR #938907
PriceChange
$354,000
Price decreased by 1%
Mar 27, 2024
Source: ECAOR #938907
PendingToActive
$359,000
Mar 15, 2024
Source: ECAOR #938907
Pending
$359,000

Market trends in Crestview

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$316K
$5KMoM
Sale-to-List Price
99.7%
Price per sq ft
$166
$0MoM
Available listings
527
20MoM

Around this home

What Locals Say about Crestview

At least 380 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 83 % Say parking is easy

  • 82 % Say yards are well-kept

  • 78 % Say it's dog friendly

  • 74 % Say there's holiday spirit

  • 67 % Say kids play outside

  • 67 % Say it's quiet

  • 57 % Say people would walk alone at night

  • 51 % Say neighbors are friendly

  • 48 % Say there's wildlife

  • 38 % Say they plan to stay for at least 5 years

  • 28 % Say there are sidewalks

  • 28 % Say streets are well-lit

  • 25 % Say it's walkable to grocery stores

  • 20 % Say it's walkable to restaurants

  • 18 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Numberonly33
    "I’ve been here for 10 years and my kids have a good experience in school as well as the neighborhood I live in the Auburn area. Yard Neighbourhood downtown area looks really good. Most areas of the town maintain well.."
    0
    Flag
  • Hazel Diane Fetter
    "Nothing it’s very quiet and safe place to walk. The neighbors are friendly. The neighborhood is clean and safe. "
    0
    Flag
  • Vym6nt6t2s
    "It’s nice here for the most part of course we have some neighbors that are not nice and make comments and are holy then thou kinda people but for the most part everyone’s nice here"
    1
    Flag
  • Martin Paras
    "Almost 2 years living here honestly I don’t see lots of dogs in our area. There’s some but definitely dog owners will love to live here because the roads are not busy. Neighborhood our pet friendly. "
    0
    Flag
  • Eperez009
    "I drive everywhere. There really isn't great city infrastructure. No sidewalks in most communities. 2 main roads go up and down the city, which creates heavy traffic. "
    0
    Flag
  • Teresa W.
    "I have lived here for almost forty years. Our small town has grown into a decent sized smaller city. People are friendly and helpful to others if they need it. Lots of different things to do. Pet friendly"
    5
    Flag
  • Aliciabyrd1227
    "There are a bunch of Stray cats. Other dog owners don’t clean up after their dogs while on walks. Some of the fences make it easy for dogs to escape."
    0
    Flag
  • Tabathaworkman
    "I don’t really know I have only lived here 2yrs so I haven’t been out in the community. Twin Hills park is nice, for walking and walking dogs also a nice park for kids"
    0
    Flag
  • Kelcie
    "Dog owners would love the roads and subdivisions they can walk their dog. It’s very quiet here and relaxing. "
    7
    Flag
  • Tabathaworkman
    "New to the area, not sure of a lot of things. Fireworks on Fourth of July and family movie nights that are free."
    0
    Flag
  • Christina B.
    "Lived here 5yrs. Neighborhood is friendly and everyone looks out for one another. We have our own FB page where we share happenings in our neighborhood/community. "
    1
    Flag
  • Kody P.
    "I have lived here for a year and am surprised I haven't been robbed yet. Seriously, if you're going to live in this city live on the south side, not the north..or don't live here. It's truly a drug infested violent area. No place to raise a family...on the north side that is. South Crestview isn't too bad, with the city expanding and new homes being built next to nicer newer homes and apartment complexes. Be wise. "
    2
    Flag
  • Shaye_murphy
    "People are friendly towards pets as long as you pick up after them and don’t let them bark all hours of the night. Just simple pet courtesies."
    0
    Flag
  • Elisha B.
    "quiet neighborhoods. friendly neighborhoods. large backyards for pets to enjoy. definitely a great place to have a pet. "
    0
    Flag
  • Justin T.
    "Have a dog yard. Everyone has the dogs on leash when walking I don’t really know what else to say jckxbxoxbxjxbx"
    0
    Flag
  • Taylormindy25
    "We take are children trick or treating every year in Crestview. We go where ever we live up and down the road so we feel more safe about letting them eat the candy"
    0
    Flag
  • Taylormindy25
    "It’s a great place to live and to rise your children. Crestview can be good and bad it’s What you make it, there jobs and school and church. The only down side is that there not really anything for children to do in this town so it easy for kids go down the wrong path. "
    0
    Flag
  • Julia R.
    "wonderful neighbors! Quiet neighborhood. ❤ Beautiful trees and well kept yards. Dogwood Estates is a perfect little gem close to shopping"
    0
    Flag
  • Christian M.
    "20miles one way very traffic congested and lots of accidents ........................................."
    0
    Flag
  • Sheronda M. T.
    "Pretty safe and the neighborhood is very nice everyone is very mindful of each others property. Crestview is a nice place to live and close to the beach. "
    0
    Flag
  • Matt H.
    "Far from everything. Takes 45 minutes to go to a real town with restaurants and shopping areas. Average age is 55+ years old and has no younger community activities. "
    0
    Flag
  • Henrycook76
    "plenty of walking around spaces up and down roads and trails. nice neighbors generally. and easy drives in and out of town "
    0
    Flag
  • Aggie909
    "Very peaceful area. No loud music, no loud kids. Fun during Halloween as this is the spot. Yards are kept up and people are nice."
    0
    Flag
  • Ashton S.
    "Newer housing is well maintained and friendly, the closer to downtown you are the worse you can expect morning commute traffic to be "
    0
    Flag
  • Aggie909
    "Very peaceful place to live. Neighbors are quiet and kids are respectful. No loud parties, or music. I feel safe here overall , even as my husband works overnight. "
    0
    Flag
  • Sylvia R.
    "This is a great area for families but it could use more sidewalks. Plenty of restaurants and a good variety."
    0
    Flag
  • KP
    "Living on the south side makes my drive to Destin about 20 minutes less then living on the north side. "
    0
    Flag
  • Fabphleb
    "40 mins by car through airforce base, with no exits for detours. Not terrible, but not ideal when lanes are closed on highway."
    0
    Flag
  • TD
    "There are many families is this small neighborhood and it is very quiet and pretty, well maintained. "
    0
    Flag
  • Jtjones513
    "I’ve lived in this neighborhood since 1994, many families move in & out real quick if they’re in the military. Fairly quiet & peaceful around here. Not far from highway & I-10, but not too close. "
    3
    Flag
  • CLocK
    "Great community!! Growing city military economic dependency, small town feel. Plenty of churches, plenty of room to expand"
    1
    Flag
  • AS
    "Quaint town with lots of traffic near i10 highway and a small town feel. Sometimes backed up for miles."
    0
    Flag
  • Mjautry
    "Traffic on 85 is awful. It can take 45 minutes to get home. We need more transportation development to keep traffic flowing."
    0
    Flag
  • Galaxymlp
    "I commute very far for work. I commute 46 miles into Pensacola to work everyday. Traffic is light in that direction. "
    0
    Flag
  • Mysticangelsdesires
    "live in neighborhood. military or retired military. easy access to highway 85 and interstate 10. friendly neighborhood. kids play in street. "
    1
    Flag
  • Mfzee
    "I don't know much about the area but what I do know is there are not many places to go shopping in the immediate area. The nearest Target is 40 min away."
    0
    Flag
  • Jerryconesr
    "The area we are at is at the very edge of city limits so you definitely need a vehicle to get to anything. It’s quiet and safe. Don’t really know why but the kids here just hide in their houses all day and night."
    0
    Flag
  • Theqsters
    "neighbors tend to stay to there self its a safe nice neighborhood close to main roads and reasturant "
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5299 Fairfield Dr

  • What is 5299 Fairfield Dr estimated to be worth?
    Trulia's estimated value for 5299 Fairfield Dr in Crestview, FL is $383,200.
  • What is the price history for 5299 Fairfield Dr?
    5299 Fairfield Dr in Crestview, FL last sold for $170,000 in October 2020.
  • Is Crestview a buyer's or seller's market?
    Crestview is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Crestview?
    The median sale price in Crestview is $316K. That is up $5K from the prior month.
  • Does 5299 Fairfield Dr have air conditioning?
    Yes, 5299 Fairfield Dr in Crestview, FL has air conditioning.
  • Does 5299 Fairfield Dr have laundry facilities?
    Yes, 5299 Fairfield Dr in Crestview, FL has in-unit laundry.

Explore by feature - Pet Friendly

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