Are yards well-kept in Chipley, FL?

As of early 2026, 92% of users say yards are well-kept

Is a car needed in Chipley, FL?

As of early 2026, 88% of users say car is needed

Is parking easy in Chipley, FL?

As of early 2026, 86% of users say parking is easy

Does Chipley, FL show holiday spirit?

As of early 2026, 86% of users say there's holiday spirit

Is Chipley, FL quiet?

As of early 2026, 83% of users say it's quiet

Would people walk alone at night in Chipley, FL?

As of early 2026, 64% of users say people would walk alone at night

Is Chipley, FL dog-friendly?

As of early 2026, 62% of users say it's dog friendly

Do kids play outside in Chipley, FL?

As of early 2026, 55% of users say kids play outside

Is there wildlife in Chipley, FL?

As of early 2026, 53% of users say there's wildlife

Are neighbors friendly in Chipley, FL?

As of early 2026, 51% of users say neighbors are friendly

Does Chipley, FL have sidewalks?

As of early 2026, 50% of users say there are sidewalks

Do residents of Chipley, FL plan to stay at least 5 years?

As of early 2026, 48% of users say they plan to stay for at least 5 years

Is Chipley, FL walkable to grocery stores?

As of early 2026, 41% of users say it's walkable to grocery stores

Are the streets well-lit in Chipley, FL?

As of early 2026, 34% of users say streets are well-lit

Is Chipley, FL walkable to restaurants?

As of early 2026, 31% of users say it's walkable to restaurants

Are there community events in Chipley, FL?

As of early 2026, 29% of users say there are community events

What is Caroline Dr estimated to be worth?

Trulia's estimated value for Caroline Dr in Chipley, FL is $202,600 .

What is the price history for Caroline Dr?

Caroline Dr in Chipley, FL last sold for $95,000 in March 2005.

Is Chipley a buyer's or seller's market?

Chipley is currently a buyer's market, based on recent for-sale activity.

What do residents say about Chipley?

Residents describe Chipley, FL as well-kept, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Chipley, FL .

How big is the lot at Caroline Dr?

The lot at Caroline Dr in Chipley, FL is about 7.5 acres .

OFF MARKET

Caroline Dr
Chipley, FL 32428

Studio

$202,600

Trulia Estimate

as of Aug 25, 2026

Est. Refi. Payment $1,359/mo*

Refinance Your Home

$202,600

Trulia Estimate

as of Aug 25, 2026

Est. Refi. Payment $1,359/mo*

Refinance Your Home

Studio

(on 7.50 acres)

Home Value

Trulia Estimate

$203K

Since last month

$1K (+0.5%)

Since last year

$14K (+7.3%)

Since last sale

$107K (+112.9%)

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 +35% in the last 10 years

Month	Estimated value
2026
August 2026	$202K
July 2026	$201K
June 2026	$195K
May 2026	$197K
April 2026	$198K
March 2026	$191K
February 2026	$179K
January 2026	$172K
2025
November 2025	$173K
October 2025	$191K
September 2025	$190K
July 2025	$189K
June 2025	$200K
April 2025	$198K
March 2025	$183K
February 2025	$142K
January 2025	$196K
2024
December 2024	$150K

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
77 Highway, Chipley, FL	0.77	Single-Family Home	$130,000	12/18/25		-	-
4427 Leisure Lakes Dr, Chipley, FL	0.79	Single-Family Home	$370,000	06/09/26	3	3	2,124
4812 Derby Dr, Chipley, FL	0.88	Single-Family Home	$340,000	02/17/26	3	2	1,489
4385 Leisure Lakes Dr, Chipley, FL	0.86	Single-Family Home	$340,000	01/02/26	3	2	1,634
3097 Woodymarion Dr, Chipley, FL	1.22	Single-Family Home	$5,100	01/21/26	3	2	1,496
4904 Partridge Pl, Chipley, FL	1.02	Single-Family Home	$12,000	07/13/26	3	2	1,420
5084 Spring Pond Rd, Chipley, FL	1.41	Single-Family Home	$750,000	10/17/25	4	3.5	3,048
5068 Airpark Blvd, Chipley, FL	1.58	Single-Family Home	$350,100	10/17/25	1	1	3,500
3376 Fawn Pl, Chipley, FL	1.74	Single-Family Home	$222,500	06/30/26	3	2	1,285
2789 Summer Dr, Chipley, FL	1.47	Single-Family Home	$700,000	05/15/26	3	2.5	2,324

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
3053 Caroline Dr, Chipley, FL 32428	0.09	$48,000	-	-	-	Recently Sold
3004 Caroline Dr, Chipley, FL 32428	0.16	$173,100	3	2	2,662	Off Market
2940 Caroline Dr, Chipley, FL 32428	0.19	$224,000	4	1	1,376	Off Market
4905 Tiger Trl, Chipley, FL 32428	0.56	$210,600	3	2	1,216	Off Market
2941 Carter Cir, Chipley, FL 32428	0.71	$411,000	3	2	1,380	Off Market
4390 Leisure Lakes Dr, Chipley, FL 32428	0.76	$139,900	-	-	-	For Sale
4427 Leisure Lakes Dr, Chipley, FL 32428	0.79	$370,000	3	3	2,124	Recently Sold
Woodymarion Dr, Chipley, FL 32428	0.76	-	-	-	-	Off Market
4399 Leisure Lakes Dr, Chipley, FL 32428	0.80	$262,800	2	2	1,250	Off Market
4393 Leisure Lakes Dr, Chipley, FL 32428	0.84	$135,000	-	-	-	Recently Sold
Woodymarion Dr #&-100, Chipley, FL 32428	0.81	$46,500	-	-	-	For Sale
4385 Leisure Lakes Dr, Chipley, FL 32428	0.86	$340,000	3	2	1,634	Recently Sold

Local Information

Map ViewExplore the area around Caroline Dr.
Schools1 Preschool School4 Elementary Schools4 Middle Schools4 High Schools
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Lot Size

7.5 acres

About this House

This single-family home is located at Caroline Dr, Chipley, FL. Caroline Dr is in Chipley, FL and in ZIP code 32428. This property has a lot size of 7.50 acres.

Caroline Dr, Chipley, FL 32428 is a studio single-family home. It last sold for $95,000 on Mar 3, 2005. It is currently off market. The Trulia Estimate is $202,600, with a rent estimate of $1,332/month.

Home Details for Caroline Dr

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 7.50 acres

Price and Tax history

Date	Event	Price
Mar 3, 2005 Source: N/A	Sold	$95,000

Year	Property tax	Tax assessment
2025	$19	$51,000

Additional Cost

Market trends in Chipley

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

111

1MoM

Around this home

Vernon Elementary School
PK-5
Public
623 Students
Washington County School District
4/10
GreatSchools Rating
Parent Rating Average
DisrespectfulWill not listen to you with your concerns and take them seriously. Don't move your children here not what it seems to be. Very judgemental woman here that wants to talk drama not school or their job. Public schools are supposed to be a safe haven. Not safe here.
Other Review
5mo ago
7 Reviews

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 Chipley

At least 24 Trulia users voted on each feature.

92 % Say yards are well-kept
88 % Say car is needed
86 % Say parking is easy
86 % Say there's holiday spirit
83 % Say it's quiet
64 % Say people would walk alone at night
62 % Say it's dog friendly
55 % Say kids play outside
53 % Say there's wildlife
51 % Say neighbors are friendly
50 % Say there are sidewalks
48 % Say they plan to stay for at least 5 years
41 % Say it's walkable to grocery stores
34 % Say streets are well-lit
31 % Say it's walkable to restaurants
29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Merissa Woods
Resident
1w ago
"I don’t have a neighborhood I live out in the woods, but Chipley itself is very good for dogs and walking dogs in the sidewalks and the capabilities of doing that. "
0
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Mandi W.
Resident
6y ago
"golf course, ponds, lakes, dirt roads, Halloween tons of tricker treating. keep main grass area cut. looks very homie"
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Carol
Resident
6y ago
"I have lived in this neighborhood for three years. Our neighbors seem to be very nice. There is government housing down the road and a lot of people walk up and down the sidewalks. All seem to be nice. "
1
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Tonya G. H.
Resident
6y ago
"if you like a country feel but still belong to a community this is the place. Woods and ponds to explore but also have neighbors and community functions. "
0
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Kayla H.
Resident
6y ago
"Home town feeling wether it is your home town or not. Your neighbor is my neighbor. If you ever need a helping hand just reach out they are everywhere here."
0
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Dafuss39
Resident
7y ago
"I live at the end of the road on the lake with traffic no trick-or-treaters and no visitors very safe neighborhood"
1
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Troyrackley
Resident
7y ago
"This area is a great place to walk your dog. Courteous neighbors, friendly passers-by, and a lovely area overall. I would highly recommend living here. "
0
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Wanda S.
12y ago
"It's okay, it's a long way to town, but you get used to it. We have a general store, a volunteer fire department, a library, and a Baptist Mission. We are also surrounded by nearby churches in neighboring areas. We have a fresh spring lake nearby, great for camping and cookouts if you have an ATV. Dependable transportation is a MUST. Military Retirees especially welcome. I'm a vet, and would LOVE some friendly, Christ Loving Peers. Must Love Animals (4 legged types.) i'm at 537. Come on by."
0
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Peaden
16y ago
"Great hunting, fishing, swimming, golfing. Very quiet area. Low crime. 35 miles to beaches. "
0
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LGBTQ Local Legal Protections

Frequently asked questions about Caroline Dr

What is Caroline Dr estimated to be worth?
Trulia's estimated value for Caroline Dr in Chipley, FL is $202,600.
What is the price history for Caroline Dr?
Caroline Dr in Chipley, FL last sold for $95,000 in March 2005.
Is Chipley a buyer's or seller's market?
Chipley is currently a buyer's market, based on recent for-sale activity.
What do residents say about Chipley?
Residents describe Chipley, FL as well-kept, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Chipley, FL.
How big is the lot at Caroline Dr?
The lot at Caroline Dr in Chipley, FL is about 7.5 acres.