108 Windsor Dr, Crestview, FL 32539
Property image
Property image
OFF MARKET

108 Windsor Dr
Crestview, FL 32539

  • 3 Beds
  • 2 Baths
  • 1,040 sqft (on 1 acre)

$183,100

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $1,198/mo*
Refinance Your Home

$183,100

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $1,198/mo*
Refinance Your Home
3 Beds
2 Baths
1,040 sqft
(on 1 acre)

Home Value

Trulia Estimate
$183K
Since last month
Increased$4K (+2%)
Since last year
Decreased$9K (-4.5%)
Since last sale
Increased$108K (+143.3%)
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 +141% in the last 10 years
MonthEstimated value
2026
August 2026$183K
July 2026$179K
June 2026$195K
May 2026$197K
April 2026$199K
March 2026$198K
February 2026$191K
January 2026$190K
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
105 Windsor Dr, Crestview, FL
0.06
Single-Family Home
$185,000
12/01/25
3
2
1,000
3382 Polly Ln, Crestview, FL
0.24
Single-Family Home
$118,000
02/11/26
3
1
1,046
118 Stephens Ln, Crestview, FL
0.20
Single-Family Home
$235,000
05/19/26
4
2
1,444
6133 Sonny Ln, Crestview, FL
0.35
Single-Family Home
$240,000
03/16/26
3
1.5
1,375
101 Stephens Ln, Crestview, FL
0.18
Single-Family Home
$190,000
06/03/26
4
2
1,268
3365 Auburn Rd, Crestview, FL
0.39
Single-Family Home
$205,000
07/24/26
3
2
1,270
6109 Tansey St, Crestview, FL
0.12
Single-Family Home
$259,050
10/21/25
3
2
1,315
6119 Tansey St, Crestview, FL
0.16
Single-Family Home
$259,000
10/10/25
3
2
1,337
6117 Tansey St, Crestview, FL
0.16
Single-Family Home
$269,000
08/28/25
3
2
1,398
6115 Tansey St, Crestview, FL
0.15
Single-Family Home
$265,000
04/07/26
3
2
1,398

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
105 Windsor Dr, Crestview, FL 32539
0.06
$185,000
3
2
1,000
Recently Sold
100 Windsor Dr, Crestview, FL 32539
0.08
$325,900
3
2
1,122
For Sale
107 Windsor Dr, Crestview, FL 32539
0.08
$239,000
3
2
1,038
For Sale
104 Stephens Ln, Crestview, FL 32539
0.11
$365,000
3
2
1,418
For Sale
6109 Tansey St, Crestview, FL 32539
0.12
$259,050
3
2
1,315
Recently Sold
Sonny Ln, Crestview, FL 32539
0.12
-
-
-
-
Off Market
6113 Tansey St, Crestview, FL 32539
0.14
$265,000
3
2
1,337
Recently Sold
6115 Tansey St, Crestview, FL 32539
0.15
$265,000
3
2
1,398
Recently Sold
80 Harrington St, Crestview, FL 32539
0.15
$347,200
3
2
1,430
Off Market
6111 Tansey St, Crestview, FL 32539
0.15
$265,000
3
2
1,398
Recently Sold
6119 Tansey St, Crestview, FL 32539
0.16
$257,300
3
2
1,337
Off Market
6117 Tansey St, Crestview, FL 32539
0.16
$267,100
3
2
1,398
Off Market

Local Information

  • Map ViewExplore the area around 108 Windsor 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
1988
Lot Size
1 acre
Living Area
1,040 sqft
Price/Sqft
$176

About this House

Beautiful like new remodeled home on an acre of water front land. Enjoy a quiet living in a peaceful neighborhood. This home features new kitchen with granite countertops. Stainless steel appliances. Energy saving LED lights. Three bedrooms And two bathrooms. Bathrooms also have granite countertops and then cabinets. There is a walk-in closet in the master bedroom. Large deck to enjoy tranquil water view. Non-smoking and no pets.
108 Windsor Dr, Crestview, FL 32539 is a 3 bedroom, 2 bathroom, 1,040 sqft single-family home built in 1988. It last sold for $75,000 on Jan 22, 2020. More recently, it was listed as a rental in May 2020 with an asking price of $1,400 per month. That rental listing was removed on June 10, 2020. It is currently off market. The Trulia Estimate is $183,100, with a rent estimate of $1,504/month.

Home Details for 108 Windsor Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Linoleum Vinyl
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Interior Details
Ceiling Fan

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other, VinylPatio

Property Information

Year Built
Year Built: 1988Year Updated: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price and Tax history

DateEventPrice
Jun 10, 2020
Source: Agent Provided
ListingRemoved
$1,335
May 25, 2020
Source: Agent Provided
PriceChange
$1,335
Price decreased by 5%
May 20, 2020
Source: Agent Provided
Listed For Rent
$1,400
Jan 22, 2020
Source: N/A
Sold
$75,000
Jan 1, 2000
Source: N/A
Sold
$75,000

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 108 Windsor Dr

  • What is 108 Windsor Dr estimated to be worth?
    Trulia's estimated value for 108 Windsor Dr in Crestview, FL is $183,100.
  • What is the price history for 108 Windsor Dr?
    108 Windsor Dr in Crestview, FL last sold for $75,000 in January 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 108 Windsor Dr have air conditioning?
    Yes, 108 Windsor Dr in Crestview, FL has air conditioning.
  • How big is the lot at 108 Windsor Dr?
    The lot at 108 Windsor Dr in Crestview, FL is about 1 acre.

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