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 $164,300 .

What is the price history for Caroline Dr?

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

Does Caroline Dr have air conditioning?

Yes, Caroline Dr in Chipley, FL has air conditioning.

How big is the lot at Caroline Dr?

The lot at Caroline Dr in Chipley, FL is about 2.5 acres .

OFF MARKET

$164,300

Trulia Estimate

Studio
2 Baths
1,064 sqft (on 2.50 acres)

Caroline Dr, Chipley, FL 32428

Est. Refi. Payment $1,172/mo*

Refinance Your Home

Currently Off Market - Sold Jan 28, 2005 for $95,000

Home Value

Trulia Estimate

$164K

Since last month

$5K (+3%)

Since last year

$8K (+4.9%)

Since last sale

$69K (+72.9%)

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 decreased by -3% in the last 10 years

Month	Estimated value
2026
September 2026	$164K
August 2026	$160K
July 2026	$165K
June 2026	$168K
May 2026	$168K
April 2026	$165K
March 2026	$159K
February 2026	$145K
January 2026	$145K
2025
December 2025	$117K
November 2025	$134K
October 2025	$153K
September 2025	$157K
August 2025	$161K
July 2025	$163K
June 2025	$164K
May 2025	$161K
April 2025	$162K
March 2025	$160K
February 2025	$156K
January 2025	$156K
2024
December 2024	$161K
November 2024	$161K
October 2024	$185K
September 2024	$185K
August 2024	$193K
2023
October 2023	$170K
September 2023	$178K
August 2023	$176K
July 2023	$189K
June 2023	$169K

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
4812 Derby Dr, Chipley, FL	0.84	Single-Family Home	$340,000	02/17/26	3	2	1,489
4385 Leisure Lakes Dr, Chipley, FL	0.82	Single-Family Home	$340,000	01/02/26	3	2	1,634
4904 Partridge Pl, Chipley, FL	0.97	Single-Family Home	$12,000	07/13/26	3	2	1,420
4427 Leisure Lakes Dr, Chipley, FL	0.73	Single-Family Home	$370,000	06/09/26	3	3	2,124
4526 Leisure Lakes Dr, Chipley, FL	1.08	Single-Family Home	$322,000	08/28/26	4	2.5	2,180
3223 Quail Ridge Dr, Chipley, FL	1.56	Single-Family Home	$200,000	07/21/26	2	2	1,232
2774 Rolling Pines Rd, Chipley, FL	1.71	Single-Family Home	$222,000	09/25/26	2	2	1,176
3320 Eagle Ct, Chipley, FL	1.54	Single-Family Home	$340,000	04/15/26	3	2	1,727
3376 Fawn Pl, Chipley, FL	1.69	Single-Family Home	$222,500	06/30/26	3	2	1,285
3097 Woodymarion Dr, Chipley, FL	1.25	Single-Family Home	$5,100	01/21/26	3	2	1,573

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
Caroline Dr, Chipley, FL 32428	0.06	$210,300	Studio	-	-	Off Market
Caroline Dr, Chipley, FL 32428	0.07	$202,900	Studio	2	816	Off Market
Caroline Dr, Chipley, FL 32428	0.11	-	-	-	-	Off Market
2939 Caroline Dr, Chipley, FL 32428	0.11	$219,800	Studio	2	1,176	Off Market
3053 Caroline Dr, Chipley, FL 32428	0.12	$48,000	-	-	-	Recently Sold
2968 Caroline Dr, Chipley, FL 32428	0.13	$99,000	1	1	912	Off Market
2993 Caroline Dr, Chipley, FL 32428	0.14	$166,200	3	2	1,216	Off Market
Caroline Dr, Chipley, FL 32428	0.14	-	-	-	-	Off Market
Caroline Dr, Chipley, FL 32428	0.14	-	-	-	-	Off Market
3044 Caroline Dr, Chipley, FL 32428	0.17	$238,300	Studio	2	1,624	Off Market
2992 Caroline Dr, Chipley, FL 32428	0.18	-	2	2	896	Off Market
2940 Caroline Dr, Chipley, FL 32428	0.18	$223,400	4	1	1,376	Off Market
3041 Caroline Dr, Chipley, FL 32428	0.18	$263,400	4	3	2,280	Off Market
3029 Caroline Dr, Chipley, FL 32428	0.19	$245,300	3	2	2,160	Off Market
3003 Caroline Dr, Chipley, FL 32428	0.20	$146,300	1	1	924	Off Market
3004 Caroline Dr, Chipley, FL 32428	0.21	$172,500	3	2	2,662	Off Market
3008 Caroline Dr, Chipley, FL 32428	0.24	$170,600	3	2	1,248	Off Market
3022 Caroline Dr, Chipley, FL 32428	0.26	$178,800	3	3	1,440	Off Market
2982 Caroline Ln, Chipley, FL 32428	0.28	-	-	-	-	Off Market
3014 Caroline Dr, Chipley, FL 32428	0.31	$211,300	3	2	1,774	Off Market

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

Single-Family Home

Built in 1998

2.5 acre lot

1,064 sqft

$154/sqft

Garage

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 2 bathrooms and approximately 1,064 sqft of floor space. This property has a lot size of 2.50 acres and was built in 1998.

Caroline Dr, Chipley, FL 32428 is a studio, 2 bathroom, 1,064 sqft single-family home built in 1998. It last sold for $95,000 on Jan 28, 2005. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $164,300, with a rent estimate of $1,162/month.

Home Details for Caroline Dr

Interior Features
Heating & Cooling Heating: Forced AirCooling System: RefrigeratorHeating Fuel: Forced Air

Exterior Features
Exterior Home Features Roof: Composition
Parking & Garage GarageParking: Garage Detached

Property Information
Year Built Year Built: 1998Year Updated: 1998
Property Type / Style Property Type: Single Family Home

Community
Units in Building: 1

Lot Information
Lot Area: 2.50 acres

Price and Tax history

Date	Event	Price
Jan 28, 2005 Source: N/A	Sold	$95,000

Year	Property tax	Tax assessment
2025	$330	$40,416

Additional Cost

Market trends in Chipley

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

116

5MoM

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
6mo 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
1mo 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. "
1
Flag
Mandi W.
Resident
6y ago
"golf course, ponds, lakes, dirt roads, Halloween tons of tricker treating. keep main grass area cut. looks very homie"
0
Flag
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
Flag
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
Flag
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
Flag
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
Flag
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
Flag
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
Flag
Peaden
16y ago
"Great hunting, fishing, swimming, golfing. Very quiet area. Low crime. 35 miles to beaches. "
0
Flag

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 $164,300.
What is the price history for Caroline Dr?
Caroline Dr in Chipley, FL last sold for $95,000 in January 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.
Does Caroline Dr have air conditioning?
Yes, Caroline Dr in Chipley, FL has air conditioning.
How big is the lot at Caroline Dr?
The lot at Caroline Dr in Chipley, FL is about 2.5 acres.