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 the price history for 2439 Leonard Dr?

2439 Leonard Dr in Chipley, FL last sold for $3,600 in April 2026.

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 .

What are the closest schools to 2439 Leonard Dr?

The closest schools to 2439 Leonard Dr in Chipley, FL are Chipley High School (rated 4/10), Kate M. Smith Elementary School (rated 4/10), Roulhac Middle School (rated 7/10).

How big is the lot at 2439 Leonard Dr?

The lot at 2439 Leonard Dr in Chipley, FL is about 1.3 acres .

SOLD

APR 17, 2026

$3,600

Last sold price

3 Beds
1 Bath
1,004 sqft (on 1.30 acres)

2439 Leonard Dr, Chipley, FL 32428

Est. Refi. Payment $98/mo*

Refinance Your Home

Currently Off Market - Sold Apr 17, 2026 for $3,600

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
3781 Pine Log Rd, Chipley, FL	0.45	Single-Family Home	$415,000	06/12/26	2	2	2,416
2474 Tiller Cemetery Dr, Chipley, FL	0.29	Single-Family Home	$585,000	08/31/26	4	3	1,941
5026 Highway 77, Chipley, FL	0.45	Single-Family Home	$550,000	05/26/26	3	2	2,261
3896 Bricknell Ave, Chipley, FL	0.80	Single-Family Home	$282,400	08/07/26	3	2	1,528
2391 Shenandoah Blvd, Chipley, FL	0.93	Single-Family Home	$320,000	05/18/26	3	2	1,624
2236 Shenandoah Blvd, Chipley, FL	1.01	Single-Family Home	$195,000	05/29/26	3	2	1,281
4127 Aquarius Dr, Chipley, FL	0.98	Single-Family Home	$227,990	01/29/26	3	2	1,416
2362 Shenandoah Blvd, Chipley, FL	0.96	Single-Family Home	$217,000	02/06/26	4	2	1,458
2387 Aquarius Dr, Chipley, FL	0.93	Single-Family Home	$272,344	04/14/26	4	2	1,728

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
Leonard Dr, Chipley, FL 32428	0.05	-	-	-	-	Off Market
4 Five 6 Angelena Ct, Chipley, FL 32428	0.10	$110,000	-	-	-	For Sale
2461 Angelena Ct, Chipley, FL 32428	0.20	$104,000	2	1	780	Recently Sold
2474 Tiller Cemetary Rd, Chipley, FL 32428	0.21	$584,800	4	3	1,941	Off Market
1 Pine Log Rd, Chipley, FL 32428	0.20	$85,000	-	-	-	For Sale
Lot 7 Angelena Ct, Chipley, FL 32428	0.27	-	-	-	-	Off Market
2474 Tiller Cemetery Dr, Chipley, FL 32428	0.29	$585,000	4	3	1,941	Recently Sold
7 Angelena Ct, Chipley, FL 32428	0.29	-	-	-	-	Off Market
3753 Bunyon Dr, Chipley, FL 32428	0.34	$130,000	-	-	-	For Sale
2416 Victory Rd, Chipley, FL 32428	0.43	$188,200	3	2	1,500	Off Market
2351 Victory Rd, Chipley, FL 32428	0.44	$211,300	3	2	1,152	Off Market
5026 Highway 77, Chipley, FL 32428	0.45	$550,000	3	2	2,261	Recently Sold

Local Information

Map ViewExplore the area around 2439 Leonard Dr.
Schools1 Preschool School4 Elementary Schools4 Middle Schools4 High Schools
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1963

1.3 acre lot

1,004 sqft

$4/sqft

About this House

This single-family home is located at 2439 Leonard Dr, Chipley, FL. 2439 Leonard Dr is in Chipley, FL and in ZIP code 32428. This property has 3 bedrooms, 1 bathroom and approximately 1,004 sqft of floor space. The last sold price per dimension was $4/sqft. This property has a lot size of 1.30 acres and was built in 1963.

2439 Leonard Dr, Chipley, FL 32428 is a 3 bedroom, 1 bathroom, 1,004 sqft single-family home built in 1963. It last sold for $3,600 on Apr 17, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $1,106/month.

Home Details for 2439 Leonard Dr

Interior Features
Levels, Entrance, & Accessibility Stories: 1

Exterior Features
Exterior Home Features Roof: OtherExterior: ShinglePorch

Property Information
Year Built Year Built: 1963Year Updated: 1975
Property Type / Style Property Type: Single Family HomeArchitecture: Other

Price & Status
Price Price Per Sqft: $4/sqft

Lot Information
Lot Area: 1.30 acres

Price and Tax history

Date	Event	Price
Apr 17, 2026 Source: N/A	Sold	$3,600
Feb 19, 2016 Source: Agent Provided	ListingRemoved	$40,000
Feb 10, 2016 Source: Agent Provided	Listed For Sale	$40,000
Dec 6, 2015 Source: Agent Provided	ListingRemoved	$40,000
Jun 24, 2015 Source: Agent Provided	PriceChange	$40,000 Price decreased by 11%
Nov 25, 2014 Source: Agent Provided	Listed For Sale	$45,000

Year	Property tax	Tax assessment
2025	$78	$5,772

Additional Cost

Market trends in Chipley

Last updated July 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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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
3w 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. "
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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."
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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. "
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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 2439 Leonard Dr

What is the price history for 2439 Leonard Dr?
2439 Leonard Dr in Chipley, FL last sold for $3,600 in April 2026.
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.
What are the closest schools to 2439 Leonard Dr?
The closest schools to 2439 Leonard Dr in Chipley, FL are Chipley High School (rated 4/10), Kate M. Smith Elementary School (rated 4/10), Roulhac Middle School (rated 7/10).
How big is the lot at 2439 Leonard Dr?
The lot at 2439 Leonard Dr in Chipley, FL is about 1.3 acres.