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

$259,400

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,267 sqft (on 0.46 acres)

102 Windsor Dr, Crestview, FL 32539

Est. Refi. Payment $1,774/mo*
Refinance Your Home
Currently Off Market - Sold Jun 24, 2022 for $260,000

Home Value

Trulia Estimate
$259K
Since last month
Decreased$4K (-1.4%)
Since last year
Decreased$8K (-3.1%)
Since last sale
Decreased$600 (-0.2%)
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 decreased by -3% in the last 10 years
MonthEstimated value
2026
October 2026$259K
September 2026$261K
August 2026$263K
July 2026$264K
June 2026$264K
May 2026$264K
April 2026$264K
March 2026$263K
February 2026$263K
January 2026$264K
2025
2024
2023

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
6109 Tansey St, Crestview, FL
0.09
Single-Family Home
$259,050
10/21/25
3
2
1,315
6114 Clover St, Crestview, FL
0.21
Single-Family Home
$259,050
04/24/26
3
2
1,245
6115 Tansey St, Crestview, FL
0.12
Single-Family Home
$265,000
04/07/26
3
2
1,398
6113 Tansey St, Crestview, FL
0.11
Single-Family Home
$265,000
12/16/25
3
2
1,337
6118 Clover St, Crestview, FL
0.24
Single-Family Home
$259,050
04/20/26
3
2
1,245
6111 Tansey St, Crestview, FL
0.13
Single-Family Home
$265,000
02/13/26
3
2
1,398
101 Stephens Ln, Crestview, FL
0.14
Single-Family Home
$190,000
06/03/26
4
2
1,268
6134 Clover St, Crestview, FL
0.28
Single-Family Home
$260,000
06/03/26
3
2
1,245
101 Stephens Ln #B, Crestview, FL
0.15
Single-Family Home
$314,900
07/20/26
4
2
1,603
6138 Clover St, Crestview, FL
0.32
Single-Family Home
$259,050
06/30/26
3
2
1,245

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
103 Windsor Dr, Crestview, FL 32539
0.03
$203,000
3
2
1,040
Off Market
Windsor Dr, Crestview, FL 32539
0.03
-
-
-
-
Off Market
108 Windsor Dr, Crestview, FL 32539
0.04
$182,000
3
2
1,040
Off Market
105 Windsor Dr, Crestview, FL 32539
0.04
$184,000
3
2
1,000
Off Market
101 Windsor Dr, Crestview, FL 32539
0.05
$223,400
3
2
1,326
Off Market
104 Windsor Dr, Crestview, FL 32539
0.05
$262,000
3
2
1,267
Off Market
110 Windsor Dr, Crestview, FL 32539
0.07
$170,000
3
2
1,014
Off Market
106 Stephens Ln, Crestview, FL 32539
0.07
$244,500
4
2
1,376
Off Market
100 Windsor Dr, Crestview, FL 32539
0.07
$325,900
3
2
1,122
For Sale
Windsor Dr #9, Crestview, FL 32539
0.07
-
-
-
-
Off Market
104 Stephens Ln, Crestview, FL 32539
0.07
$356,400
3
2
1,418
Off Market
87 Acre Windsor Dr, Crestview, FL 32539
0.07
-
-
-
-
Off Market
93 Acre Windsor Dr, Crestview, FL 32539
0.07
-
-
-
-
Off Market
107 Windsor Dr, Crestview, FL 32539
0.07
$239,000
3
2
1,038
For Sale
108 Stephens Ln, Crestview, FL 32539
0.08
$258,000
3
2
1,626
Off Market
112 Windsor Dr, Crestview, FL 32539
0.08
$237,600
3
2
1,028
Off Market
102 Stephens Ln, Crestview, FL 32539
0.09
$213,400
3
2
1,053
Off Market
6065 Sonny Ln, Crestview, FL 32539
0.09
$150,900
3
2
1,120
Off Market
6071 Sonny Ln, Crestview, FL 32539
0.09
-
3
2
1,025
Off Market
6109 Tansey St, Crestview, FL 32539
0.09
$257,200
3
2
1,315
Off Market

Local Information

  • Map ViewExplore the area around 102 Windsor Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2022
0.46 acre lot
1,267 sqft
$205/sqft

About this House

What's unique:Shaker-style cabinetsElegant granite countertopsGenerously sized laundry roomCozy carpetingOpen-concept designLvp flooring
This single-family home is located at 102 Windsor Dr, Crestview, FL. 102 Windsor Dr is in Crestview, FL and in ZIP code 32539. This property has 3 bedrooms, 2 bathrooms and approximately 1,267 sqft of floor space. This property has a lot size of 0.46 acres and was built in 2022.
102 Windsor Dr, Crestview, FL 32539 is a 3 bedroom, 2 bathroom, 1,267 sqft single-family home built in 2022. It last sold for $260,000 on Jun 24, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $259,400, with a rent estimate of $1,701/month.

Home Details for 102 Windsor Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Concrete
Heating & Cooling
Air ConditioningCooling System: Central

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other

Property Information

Year Built
Year Built: 2022
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
Mar 5, 2026
Source: ECAOR #987599
ListingRemoved
$265,000
Oct 15, 2025
Source: ECAOR #987599
Listed For Sale
$265,000
Mar 4, 2025
Source: ECAOR #967691
ListingRemoved
$264,900
Feb 4, 2025
Source: ECAOR #967691
Listed For Sale
$264,900
Feb 1, 2025
Source: ECAOR #956063
ListingRemoved
$274,900

Market trends in Crestview

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$310K
$11.67KMoM
Sale-to-List Price
99.6%
0.1%MoM
Price per sq ft
$169
$2MoM
Available listings
478
19MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Crestview

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 74% say there's holiday spirit
  • 51% say neighbors are friendly
  • 28% say there are sidewalks
Trulia Trick or TreatStart Ghost Hunt
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 102 Windsor Dr

  • What is 102 Windsor Dr estimated to be worth?
    Trulia's estimated value for 102 Windsor Dr in Crestview, FL is $259,400.
  • What is the price history for 102 Windsor Dr?
    102 Windsor Dr in Crestview, FL last sold for $260,000 in June 2022.
  • Is Crestview a buyer's or seller's market?
    Crestview is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Crestview?
    The median sale price in Crestview is $310K. That is down $11.67K from the prior month.
  • Does 102 Windsor Dr have air conditioning?
    Yes, 102 Windsor Dr in Crestview, FL has air conditioning.
  • How big is the lot at 102 Windsor Dr?
    The lot at 102 Windsor Dr in Crestview, FL is about 0.46 acres (20,037 sq ft).

Explore by feature - Pet Friendly

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