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 585 Bennett Dr estimated to be worth?

Trulia's estimated value for 585 Bennett Dr in Chipley, FL is $158,100 .

What is the price history for 585 Bennett Dr?

585 Bennett Dr in Chipley, FL last sold for $70,000 in October 2014.

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 585 Bennett Dr have air conditioning?

Yes, 585 Bennett Dr in Chipley, FL has air conditioning.

How big is the lot at 585 Bennett Dr?

The lot at 585 Bennett Dr in Chipley, FL is about 0.17 acres (7,405 sq ft).

OFF MARKET

585 Bennett Dr
Chipley, FL 32428

3 Beds
1 Bath
1,384 sqft

$158,100

Trulia Estimate

as of Aug 21, 2026

Est. Refi. Payment $1,071/mo*

Refinance Your Home

$158,100

Trulia Estimate

as of Aug 21, 2026

Est. Refi. Payment $1,071/mo*

Refinance Your Home

3 Beds

1 Bath

1,384 sqft

Home Value

Trulia Estimate

$158K

Since last month

$2K (-0.9%)

Since last year

$500 (+0.3%)

Since last sale

$88K (+125.1%)

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 +90% in the last 10 years

Month	Estimated value
2026
August 2026	$158K
July 2026	$159K
June 2026	$159K
May 2026	$159K
April 2026	$156K
March 2026	$156K
February 2026	$151K
January 2026	$150K
2025
December 2025	$147K
November 2025	$152K
October 2025	$153K
September 2025	$155K
August 2025	$157K
July 2025	$163K
June 2025	$160K
May 2025	$162K
April 2025	$162K
March 2025	$160K
February 2025	$159K
January 2025	$159K
2024
December 2024	$159K
November 2024	$163K
October 2024	$163K
September 2024	$163K
August 2024	$163K
July 2024	$161K
June 2024	$168K
May 2024	$170K
April 2024	$167K
March 2024	$166K
February 2024	$163K
January 2024	$163K
2023
December 2023	$164K
November 2023	$166K
October 2023	$166K
September 2023	$169K
August 2023	$167K
July 2023	$166K
June 2023	$163K
May 2023	$163K
April 2023	$161K
March 2023	$159K
February 2023	$157K
January 2023	$158K
2022
December 2022	$160K
November 2022	$164K
October 2022	$165K
September 2022	$166K
August 2022	$163K
July 2022	$161K
June 2022	$158K
May 2022	$156K
April 2022	$154K
March 2022	$154K
February 2022	$152K
January 2022	$151K
2021
December 2021	$151K
November 2021	$151K
October 2021	$150K
September 2021	$149K
August 2021	$149K
July 2021	$142K
June 2021	$124K
May 2021	$99K
April 2021	$98K
March 2021	$95K
February 2021	$96K
January 2021	$93K
2020
December 2020	$93K
November 2020	$91K
October 2020	$90K
September 2020	$84K
August 2020	$85K
July 2020	$85K
June 2020	$85K
May 2020	$84K
April 2020	$84K
March 2020	$84K
February 2020	$84K
January 2020	$85K
2019
December 2019	$86K
November 2019	$87K
October 2019	$87K
September 2019	$87K
August 2019	$86K
July 2019	$84K
June 2019	$83K
May 2019	$85K
April 2019	$84K
March 2019	$80K
February 2019	$82K
January 2019	$87K
2018
December 2018	$84K
November 2018	$86K
October 2018	$87K
September 2018	$87K
August 2018	$86K
July 2018	$86K
June 2018	$86K
May 2018	$85K
April 2018	$88K
March 2018	$87K
February 2018	$88K
January 2018	$91K
2017
December 2017	$89K
November 2017	$90K
October 2017	$90K
September 2017	$91K
August 2017	$91K
July 2017	$90K
June 2017	$89K
May 2017	$89K
April 2017	$88K
March 2017	$88K
February 2017	$87K
January 2017	$86K
2016
December 2016	$86K
November 2016	$85K
October 2016	$84K
September 2016	$84K
August 2016	$83K

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
1222 Campbellton Ave, Chipley, FL	0.14	Single-Family Home	$60,000	08/07/26	3	1	1,064
1228 Church Ave, Chipley, FL	0.38	Single-Family Home	$80,000	01/28/26	3	2	1,080
576 Martin Luther King Dr, Chipley, FL	0.28	Single-Family Home	$160,000	02/13/26	3	1	1,343
1294 Old Bonifay Rd, Chipley, FL	0.44	Single-Family Home	$55,000	01/07/26	3	2	1,337
1331 Coggin Ave, Chipley, FL	0.66	Single-Family Home	$180,000	05/05/26	3	1	1,316
550 Bennett Dr, Chipley, FL	0.15	Single-Family Home	$60,000	02/26/26		2	1,107
540 4th St, Chipley, FL	0.53	Single-Family Home	$136,000	02/27/26	3	1	1,004
1275 Morris Ave, Chipley, FL	0.52	Single-Family Home	$164,900	11/25/25	3	2	1,245
1322 Coggin Ave, Chipley, FL	0.60	Single-Family Home	$158,000	12/15/25	2	1	1,383
716 Orange St, Chipley, FL	0.66	Single-Family Home	$65,000	01/07/26	3	2	1,878

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
1222 Campbellton Ave, Chipley, FL 32428	0.14	$60,000	3	1	1,064	Recently Sold
1203 Old Bonifay Rd, Chipley, FL 32428	0.14	$108,900	3	1	1,113	Off Market
632 Bennett Dr, Chipley, FL 32428	0.23	-	1	1	876	Off Market
534 Martin Luther King Dr, Chipley, FL 32428	0.27	$90,000	1	1	1,916	For Sale
660 Highway 273, Chipley, FL 32428	0.31	$779,000	4	3.5	4,212	For Sale
576 Martin Luther King Dr, Chipley, FL 32428	0.28	$160,000	3	1	1,343	Recently Sold
1239 Holley Ave, Chipley, FL 32428	0.33	$194,500	2	2	1,338	Recently Sold
1172 Glory Ln, Chipley, FL 32428	0.35	$132,300	2	2	1,216	Off Market
581 7th St, Chipley, FL 32428	0.34	-	3	1	856	Off Market
657 Main St, Chipley, FL 32428	0.33	$268,800	3	2	1,804	Off Market
644 Pearson St, Chipley, FL 32428	0.33	$332,600	3	3.5	2,328	Off Market
1181 Glory Ln, Chipley, FL 32428	0.41	$180,100	3	2	1,352	Off Market

Local Information

Map ViewExplore the area around 585 Bennett 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

1994

Living Area

1,384 sqft

Price/Sqft

$114

Parking

Garage

About this House

Nice 3/1 brick home in town.This home has all new hardwood flooring in living,dinning,kitchen area and new carpet in bedrooms.Home was completely repainted through out and has new light fixtures.New roof and new central heating/cooling unit.This home is ready for its new family.Call today for your appointment . Brokered And Advertised By: SOUTHERN WAY REALTY, INC. Listing Agent: Wanda Raney

585 Bennett Dr, Chipley, FL 32428 is a 3 bedroom, 1 bathroom, 1,384 sqft single-family home built in 1994. It last sold for $70,000 on Oct 14, 2014. It is currently off market. The Trulia Estimate is $158,100, with a rent estimate of $1,305/month.

Home Details for 585 Bennett Dr

Exterior Features
Exterior Home Features Roof: CompositionExterior: Brick
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached

Property Information
Year Built Year Built: 1994Year Updated: 1996
Property Type / Style Property Type: Single Family Home

Interior Features
Heating & Cooling Air ConditioningCooling System: Central
Levels, Entrance, & Accessibility Floors: Hardwood
Interior Details Ceiling Fan

Community
Units in Building: 1

Lot Information
Lot Area: 7405 sqft

Price and Tax history

Date	Event	Price
Oct 14, 2014 Source: N/A	Sold	$70,000
Mar 13, 2013 Source: Agent Provided	ListingRemoved	$69,000
Feb 4, 2013 Source: Agent Provided	PriceChange	$69,000 Price decreased by 7%
Sep 17, 2012 Source: Agent Provided	Listed For Sale	$74,000
Jun 1, 2012 Source: N/A	Sold	$26,100

Year	Property tax	Tax assessment
2025	$521	$118,090

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
0w 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"
0
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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
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
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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
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 585 Bennett Dr

What is 585 Bennett Dr estimated to be worth?
Trulia's estimated value for 585 Bennett Dr in Chipley, FL is $158,100.
What is the price history for 585 Bennett Dr?
585 Bennett Dr in Chipley, FL last sold for $70,000 in October 2014.
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 585 Bennett Dr have air conditioning?
Yes, 585 Bennett Dr in Chipley, FL has air conditioning.
How big is the lot at 585 Bennett Dr?
The lot at 585 Bennett Dr in Chipley, FL is about 0.17 acres (7,405 sq ft).