423 Bobby Dr, Crestview, FL 32536
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Property image
OFF MARKET

423 Bobby Dr
Crestview, FL 32536

  • 3 Beds
  • 2 Baths
  • 1,783 sqft

$297,900

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $1,899/mo*
Refinance Your Home

$297,900

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $1,899/mo*
Refinance Your Home
3 Beds
2 Baths
1,783 sqft

Home Value

Trulia Estimate
$298K
Since last month
Decreased$6K (-1.8%)
Since last year
Decreased$3K (-0.9%)
Since last sale
Increased$8K (+2.8%)
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 +83% in the last 10 years
MonthEstimated value
2026
August 2026$297K
July 2026$297K
June 2026$303K
May 2026$301K
April 2026$302K
March 2026$301K
February 2026$300K
January 2026$298K
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
417 Bobby Dr, Crestview, FL
0.06
Single-Family Home
$290,000
01/06/26
3
2
1,943
300 Peggy Dr, Crestview, FL
0.11
Single-Family Home
$334,900
06/30/26
3
2
1,762
193 Villacrest Dr, Crestview, FL
0.24
Single-Family Home
$283,900
06/08/26
3
2
1,796
314 Peggy Dr, Crestview, FL
0.11
Single-Family Home
$315,000
01/13/26
4
2
1,962
403 Juniper Dr, Crestview, FL
0.17
Single-Family Home
$305,000
04/29/26
3
2
1,370
407 Bobby Dr, Crestview, FL
0.15
Single-Family Home
$300,000
01/27/26
4
2
1,988
306 Island Dr, Crestview, FL
0.20
Single-Family Home
$252,500
11/04/25
3
2
1,508
1312 Jeffrine Dr, Crestview, FL
0.22
Single-Family Home
$273,990
02/06/26
3
2
1,465
1226 Northview Dr, Crestview, FL
0.17
Single-Family Home
$269,000
06/03/26
4
2
1,666
204 Villacrest Dr, Crestview, FL
0.29
Single-Family Home
$280,000
07/14/26
3
2
1,737

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
244 Trish Dr, Crestview, FL 32536
0.03
$314,000
4
2
2,099
Off Market
242 Trish Dr, Crestview, FL 32536
0.02
$294,100
3
2
1,548
Off Market
238 Trish Dr, Crestview, FL 32536
0.04
$325,000
4
2
2,034
For Sale
419 Bobby Dr, Crestview, FL 32536
0.04
$305,200
4
2
1,962
Off Market
250 Trish Dr, Crestview, FL 32536
0.08
$268,600
4
2
1,870
Off Market
417 Bobby Dr, Crestview, FL 32536
0.06
$290,000
3
2
1,943
Recently Sold
252 Trish Dr, Crestview, FL 32536
0.10
$314,000
4
2
2,090
Off Market
300 Peggy Dr, Crestview, FL 32536
0.11
$334,900
3
2
1,762
Recently Sold
1327 Jeffrine Dr, Crestview, FL 32536
0.08
$258,900
3
2
1,404
For Sale
102 Loop Dr, Crestview, FL 32536
0.12
$288,500
3
2
1,370
Off Market
318 Peggy Dr, Crestview, FL 32536
0.10
$333,500
4
2
2,225
Off Market
314 Peggy Dr, Crestview, FL 32536
0.11
$315,000
4
2
1,962
Recently Sold

Local Information

  • Map ViewExplore the area around 423 Bobby Dr.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Living Area
1,783 sqft
Price/Sqft
$167

About this House

AVAILABLE MAY 12, 2025! $50 MILITARY DISCOUNT! Introducing a charming 3 bedroom, 2 bathroom home located in the desirable South Crestview area. This lovely house features a split floor plan, perfect for added privacy. The open-concept floorplan creates a spacious and inviting atmosphere, ideal for entertaining guests or simply relaxing at home. The large kitchen offers plenty of counter space, center island, and tons of storage. Outside, enjoy the privacy of a fenced backyard, perfect for outdoor activities or simply enjoying the fresh air. Conveniently located to the area's military bases, shopping, dining, and entertainment, this home offers both comfort and convenience.

No smoking and NO cats allowed due to medical allergy. Dogs allowed.......

regardless of if they own a pet or not. Applicants with an ESA are also required to complete the application.

** Fees Required once an application is approved include, but may not be limited to: Security Deposit, Non-Refundable Fees (cleaning and rekey), $20 Certified Mail Fee, and Pet Fees (when applicable).
423 Bobby Dr, Crestview, FL 32536 is a 3 bedroom, 2 bathroom, 1,783 sqft single-family home. It last sold for $289,000 on Jul 8, 2022 (15,111% above the $1,900 asking price). More recently, it was listed as a rental in April 2025 with an asking price of $1,900 per month. That rental listing was removed on April 22, 2025. It is currently off market. The Trulia Estimate is $297,900, with a rent estimate of $1,820/month.

Home Details for 423 Bobby Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For DetailsAvailable: now

Interior Features

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

Price and Tax history

DateEventPrice
Apr 22, 2025
Source: Zillow Rentals
ListingRemoved
$1,900
Apr 8, 2025
Source: Zillow Rentals
Listed For Rent
$1,900
Feb 11, 2025
Source: Zillow Rentals
ListingRemoved
$1,850
Feb 8, 2025
Source: Zillow Rentals
PriceChange
$1,850
Price decreased by 14%
Jan 26, 2025
Source: Zillow Rentals
Listed For Rent
$2,150

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
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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

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Apartments for Rent

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Explore by feature - Pet Friendly

107 pet-friendly rentals in Crestview, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

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Homes for sale near 423 Bobby Dr

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Off Market Homes Near 423 Bobby Dr

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Frequently asked questions about 423 Bobby Dr

  • What is 423 Bobby Dr estimated to be worth?
    Trulia's estimated value for 423 Bobby Dr in Crestview, FL is $297,900.
  • What is the price history for 423 Bobby Dr?
    423 Bobby Dr in Crestview, FL last sold for $289,000 in July 2022.
  • 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 423 Bobby Dr have air conditioning?
    Yes, 423 Bobby Dr in Crestview, FL has air conditioning.
  • Does 423 Bobby Dr have laundry facilities?
    Yes, 423 Bobby Dr in Crestview, FL has in-unit laundry.