299 James St, Crestview, FL 32536
OFF MARKET

299 James St
Crestview, FL 32536

  • 4 Beds
  • 3 Baths
  • 1,945 sqft (on 0.93 acres)

$414,800

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $2,597/mo*
Refinance Your Home

$414,800

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $2,597/mo*
Refinance Your Home
4 Beds
3 Baths
1,945 sqft
(on 0.93 acres)

Local Information

  • Map ViewExplore the area around 299 James St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1984
Lot Size
0.93 acres
Living Area
1,945 sqft
Price/Sqft
$213
Parking
Garage

About this House

Hidden Gem situated on almost an acre lot in the heart of Crestview! Many upgrades to this home in the last 3 years. From the master bedroom suite to the patio and deck, this home is incredible. Here are just some of the upgrades/remodeling: (in th e last 12 months) Florida room (aka-office/family room/media room); converted the wood burning fireplace to a ventless gas fireplace;, installed electric fireplace in Florida room; added concrete driveway to accomodate RV/Boat/Trailer; 12 x 30 Utilit y Shed with full power; new septic drain field installed using bio-domes technology; hurricane rate garage door; and security system. Approx 1 1/2 years ago, converted attached garage into a large master suite with full bath, large built-in cedar che st, and walk-in closet, the main master bedroom suite was completely remodeled; 2nd HVAC unit installed; Rinnai tankless hot water system installed. 3 years ago, sellers added the screened porch with ceiling fans, floor drain and there's even water and a drain for a future sink; concreted the patio area and added a decorative stone wall; multi-level decking; new dimensional shingle roof on home and detached garage; additional storage area was added to the detached garage.
299 James St, Crestview, FL 32536 is a 4 bedroom, 3 bathroom, 1,945 sqft single-family home built in 1984. It last sold for $272,800 on Mar 10, 2010. It is currently off market. The Trulia Estimate is $414,800, with a rent estimate of $2,128/month.

Home Details for 299 James St

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Other, Hardwood
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other, Brick
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1984Year Updated: 1988
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.93 acres

Price History for 299 James St

DatePriceEventSource
03/10/2010$272,800Sold
N/A
11/22/2009$299,850ListingRemovedAgent Provided
10/04/2009$299,850Listed For SaleAgent Provided
04/03/2000$129,700Sold
N/A

Market trends in Crestview

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$311K
$13.3KMoM
Sale-to-List Price
99.7%
0.2%MoM
Price per sq ft
$165
$1MoM
Available listings
507
6MoM
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Property Tax and Assessment

Year2025
Tax$3,188
Assessment$372,283
Home facts updated by county records

Comparable Sales for 299 James St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
295 Garden St, Crestview, FL
0.25
Single-Family Home
$353,000
04/03/26
3
4
3,160
309 Gil Ava St, Crestview, FL
0.18
Single-Family Home
$324,900
06/22/26
4
2
1,670
1310 Texas Pkwy, Crestview, FL
0.12
Single-Family Home
$282,715
05/11/26
3
2
1,573
211 Jones Rd, Crestview, FL
0.24
Single-Family Home
$305,650
09/05/25
4
2
1,567
1912 N Pearl St, Crestview, FL
0.56
Single-Family Home
$285,000
03/04/26
4
3
1,848
147 Gillis Dr, Crestview, FL
0.54
Single-Family Home
$395,000
02/04/26
4
2.5
2,402
786 9th Ave, Crestview, FL
0.30
Single-Family Home
$180,000
09/19/25
3
2
1,582
970 Texas Pkwy, Crestview, FL
0.26
Single-Family Home
$306,000
04/16/26
4
2
1,858
107 Jeff Dr, Crestview, FL
0.25
Single-Family Home
$299,900
04/29/26
3
2
1,467
968 Texas Pkwy, Crestview, FL
0.31
Single-Family Home
$311,500
03/02/26
4
2
1,858

Nearby homes

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Assigned Schools

These are the assigned schools for 299 James St.
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 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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Homes for sale near 299 James St

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Off Market Homes Near 299 James St

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Frequently asked questions about 299 James St

  • What is 299 James St estimated to be worth?
    Trulia's estimated value for 299 James St in Crestview, FL is $414,800.
  • What is the price history for 299 James St?
    299 James St in Crestview, FL last sold for $272,800 in March 2010.
  • 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 $311K. That is up $13.3K from the prior month.
  • Does 299 James St have air conditioning?
    Yes, 299 James St in Crestview, FL has air conditioning.
  • How big is the lot at 299 James St?
    The lot at 299 James St in Crestview, FL is about 0.93 acres (40,510 sq ft).