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 Leonard Dr estimated to be worth?

Trulia's estimated value for Leonard Dr in Chipley, FL is $151,200 .

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 Leonard Dr?

The closest schools to 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 Leonard Dr?

The lot at Leonard Dr in Chipley, FL is about 0.82 acres (35,719 sq ft).

Does Leonard Dr have a garage?

Yes, Leonard Dr in Chipley, FL has a garage.

OFF MARKET

$151,200

Trulia Estimate

3 Beds
2 Baths
1,800 sqft (on 0.82 acres)

Leonard Dr, Chipley, FL 32428

Est. Refi. Payment $1,024/mo*

Refinance Your Home

Home Value

Trulia Estimate

$151K

Since last month

$4K (-2.8%)

Since last year

$5K (+3.3%)

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 +3% in the last 10 years

Month	Estimated value
2026
August 2026	$151K
June 2026	$156K
May 2026	$157K
April 2026	$163K
March 2026	$146K

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
3896 Bricknell Ave, Chipley, FL	0.29	Single-Family Home	$282,400	08/07/26	3	2	1,528
5026 Highway 77, Chipley, FL	0.20	Single-Family Home	$550,000	05/26/26	3	2	2,261
2085 Babcock St, Chipley, FL	0.51	Single-Family Home	$237,451	06/26/26	4	2	1,799
2103 Babcock St, Chipley, FL	0.52	Single-Family Home	$245,000	05/29/26	4	2	1,799
4135 Highland Ave, Chipley, FL	0.53	Single-Family Home	$255,700	08/13/26	4	2	1,799
4113 Gulliver Dr, Chipley, FL	0.51	Single-Family Home	$241,000	06/12/26	4	2	1,799
2236 Shenandoah Blvd, Chipley, FL	0.52	Single-Family Home	$195,000	05/29/26	3	2	1,281
3952 Concord Blvd, Chipley, FL	0.81	Single-Family Home	$264,900	01/14/26	3	2	1,481
2219 Voltaire Dr, Chipley, FL	0.62	Single-Family Home	$229,900	04/02/26	3	2	1,302
2439 Leonard Dr, Chipley, FL	0.53	Single-Family Home	$3,600	04/17/26	3	1	1,004

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
5026 Highway 77, Chipley, FL 32428	0.20	$550,000	3	2	2,261	Recently Sold
Lot 7 Bricknell Ave, Chipley, FL 32428	0.23	$22,000	-	-	-	For Sale
3918 Bricknell Ave, Chipley, FL 32428	0.24	$209,000	3	2	1,259	For Sale
3900 Bricknell Ave, Chipley, FL 32428	0.25	$276,900	3	2	1,279	For Sale
3813 Bricknell Ave, Chipley, FL 32428	0.27	$213,100	3	2	1,290	Off Market
3879 Bricknell Ave, Chipley, FL 32428	0.27	$281,300	4	2	1,787	Off Market
3884 Bricknell Ave, Chipley, FL 32428	0.29	$283,900	3	2	1,528	For Sale
3892 Bricknell Ave, Chipley, FL 32428	0.29	$299,900	3	2	1,760	For Sale
3896 Bricknell Ave, Chipley, FL 32428	0.29	$282,400	3	2	1,528	Recently Sold
Lot 5 Voltaire Dr, Chipley, FL 32428	0.31	$22,000	-	-	-	For Sale
The Emerald B, Chipley, FL 32428	0.33	$273,800+	3	2	1,881	-
The Opal B, Chipley, FL 32428	0.33	$277,500+	3	2	2,160	-

Local Information

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

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1988

Lot Size

0.82 acres

Living Area

1,800 sqft

Price/Sqft

$84

Parking

Garage

About this House

NICE 3 BR. 1 1/2 BATH BRICK HOME ON .82 OF AN ACRE THAT IS CHAINLINK FENCED IN. HOME HAS A NICE FIREPLACE IN THE LIVINGROOM A SPACIOUS KITCHEN WITH WOOD CABINETS. GOOD SIZE DINING ROOM. HOME HAS A LAKE VIEW FROM KITCHEN WINDOW. THERE ARE 3 BEDROOMS WITH A 1/2 BATH WITH WALK-IN CLOSET IN THE MASTER. THERE ARE 2 OTHER BEDROOMS AND A BASEMENT TYPE ROOM UNDER THE HOME. NEW WELL PUMP AND TANK IN JULY 2014 NEW ROOF IN 2002 AND THE LAMINATE FLOOR IN 2007. HOME HAS A COVERED CARPORT AND AN OUT BUILDING. PRICED TO SELL. MAKE YOUR APPOINTMENT TODAY. Brokered And Advertised By: Elite Realty Listing Agent: Joel Robbins

Leonard Dr, Chipley, FL 32428 is a 3 bedroom, 2 bathroom, 1,800 sqft single-family home built in 1988. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $151,200, with a rent estimate of $1,795/month.

Home Details for Leonard Dr

Property Information
Year Built Year Built: 1988
Property Type / Style Property Type: Single Family Home

Interior Features
Fireplace & Spa Fireplace
Interior Details Ceiling Fan

Exterior Features
Exterior Home Features Porch
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached

Lot Information
Lot Area: 0.82 acres

Price and Tax history

Date	Event	Price
Apr 19, 2023 Source: CPAR #725267	ListingRemoved
Apr 18, 2022 Source: CPAR #725267	Listed For Sale	$11,000
Feb 26, 2015 Source: Agent Provided	ListingRemoved	$89,900
Nov 7, 2014 Source: Agent Provided	Listed For Sale	$89,900

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
2w 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."
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."
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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 Leonard Dr

What is Leonard Dr estimated to be worth?
Trulia's estimated value for Leonard Dr in Chipley, FL is $151,200.
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 Leonard Dr?
The closest schools to 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 Leonard Dr?
The lot at Leonard Dr in Chipley, FL is about 0.82 acres (35,719 sq ft).
Does Leonard Dr have a garage?
Yes, Leonard Dr in Chipley, FL has a garage.