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 729 Main St estimated to be worth?

Trulia's estimated value for 729 Main St in Chipley, FL is $343,100 .

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 729 Main St?

The closest schools to 729 Main St in Chipley, FL are Chipley High School (rated 4/10), Kate M. Smith Elementary School (rated 4/10), Roulhac Middle School (rated 7/10).

Does 729 Main St have air conditioning?

Yes, 729 Main St in Chipley, FL has air conditioning.

Does 729 Main St have a pool?

Yes, 729 Main St in Chipley, FL has a pool.

OFF MARKET

$343,100

Trulia Estimate

4 Beds
2 Baths
2,971 sqft (on 1.01 acres)

729 Main St, Chipley, FL 32428

Est. Refi. Payment $2,247/mo*

Refinance Your Home

Home Value

Trulia Estimate

$343K

Since last month

$4K (-1.1%)

Since last year

$12K (+3.5%)

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 +149% in the last 10 years

Month	Estimated value
2026
August 2026	$344K
July 2026	$348K
June 2026	$355K
May 2026	$343K
April 2026	$334K
March 2026	$330K
2025
September 2025	$323K
August 2025	$332K
July 2025	$339K
June 2025	$323K
May 2025	$315K
April 2025	$308K
March 2025	$308K
February 2025	$307K
January 2025	$285K
2024
December 2024	$299K
November 2024	$303K
October 2024	$309K
September 2024	$315K
August 2024	$308K
July 2024	$273K
June 2024	$281K
May 2024	$284K
April 2024	$284K
March 2024	$279K
February 2024	$272K
January 2024	$276K
2023
December 2023	$275K
November 2023	$261K
October 2023	$267K
September 2023	$271K
August 2023	$269K
July 2023	$289K
June 2023	$257K
May 2023	$267K
April 2023	$267K
March 2023	$265K
February 2023	$248K
January 2023	$244K
2022
December 2022	$250K
November 2022	$257K
October 2022	$264K
September 2022	$266K
August 2022	$263K
July 2022	$252K
June 2022	$250K
May 2022	$245K
April 2022	$245K
March 2022	$243K
February 2022	$237K
January 2022	$234K
2021
December 2021	$235K
November 2021	$237K
October 2021	$236K
September 2021	$235K
August 2021	$241K
July 2021	$246K
June 2021	$221K
May 2021	$195K
April 2021	$183K
March 2021	$182K
February 2021	$173K
January 2021	$200K
2020
December 2020	$195K
November 2020	$192K
October 2020	$185K
September 2020	$186K
August 2020	$190K
July 2020	$190K
June 2020	$189K
May 2020	$187K
April 2020	$186K
March 2020	$185K
February 2020	$184K
January 2020	$183K
2019
December 2019	$183K
November 2019	$181K
October 2019	$177K
September 2019	$180K
August 2019	$179K
July 2019	$179K
June 2019	$176K
May 2019	$178K
April 2019	$177K
March 2019	$178K
February 2019	$175K
January 2019	$175K
2018
December 2018	$172K
November 2018	$169K
October 2018	$171K
September 2018	$170K
August 2018	$171K
July 2018	$170K
June 2018	$166K
May 2018	$165K
April 2018	$165K
March 2018	$162K
February 2018	$164K
January 2018	$164K
2017
December 2017	$163K
November 2017	$160K
October 2017	$155K
September 2017	$155K
August 2017	$158K
July 2017	$158K
June 2017	$163K
May 2017	$158K
April 2017	$157K
March 2017	$158K
February 2017	$156K
January 2017	$169K
2016
December 2016	$157K
November 2016	$143K
October 2016	$138K
September 2016	$138K

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
632 Main St, Chipley, FL	0.31	Single-Family Home	$260,000	12/19/25	4	2	2,684
1224 Church Ave, Chipley, FL	0.28	Single-Family Home	$264,900	12/11/25	4	3	2,762
1314 Coggin Ave, Chipley, FL	0.23	Single-Family Home	$205,000	04/09/26	3	2	1,724
873 Main St, Chipley, FL	0.49	Single-Family Home	$194,900	06/10/26	4	2	2,114
1342 Old Bonifay Rd, Chipley, FL	0.38	Single-Family Home	$130,000	10/10/25	3	2.5	1,896
1294 Old Bonifay Rd, Chipley, FL	0.17	Single-Family Home	$55,000	01/07/26	3	2	1,337
1286 Wells Ave, Chipley, FL	0.54	Single-Family Home	$265,000	07/30/26	4	2	2,198
576 Martin Luther King Dr, Chipley, FL	0.07	Single-Family Home	$160,000	02/13/26	3	1	1,343
1380 Watts Ave, Chipley, FL	0.55	Single-Family Home	$199,900	04/17/26	3	2	1,480
1228 Church Ave, Chipley, FL	0.27	Single-Family Home	$80,000	01/28/26	3	2	1,080

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
735 Main St, Chipley, FL 32428	0.03	$295,500	4	3	3,121	Off Market
576 Martin Luther King Dr, Chipley, FL 32428	0.07	$160,000	3	1	1,343	Recently Sold
704 Main St, Chipley, FL 32428	0.09	$175,000	3	2	1,644	For Sale
700 Main St, Chipley, FL 32428	0.10	$207,500	3	2	2,030	Off Market
643 5th St, Chipley, FL 32428	0.16	$192,300	2	1	1,283	Off Market
768 Main St, Chipley, FL 32428	0.16	$189,000	4	2	2,299	For Sale
5th St, Chipley, FL 32428	0.15	-	-	-	-	Off Market
644 Pearson St, Chipley, FL 32428	0.18	$329,500	3	3.5	2,328	Off Market
781 Main St, Chipley, FL 32428	0.18	$153,000	3	2	1,938	Off Market
Watts Ave, Chipley, FL 32428	0.19	-	-	-	-	Off Market
586 N 5th St, Chipley, FL 32428	0.19	$150,300	3	2	1,340	Off Market
620 4th St, Chipley, FL 32428	0.20	$485,000	4	3	3,756	For Sale

Local Information

Map ViewExplore the area around 729 Main St.
Schools1 Preschool School4 Elementary Schools4 Middle Schools4 High Schools
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1925

Lot Size

1.01 acres

Living Area

2,971 sqft

Price/Sqft

$115

Parking

Garage

About this House

This 4BR/2BA craftsman beauty, known as the ''Kate M. Smith'' home, has lots to offer with a in town location. First floor features oversized living room, office/sitting room, dining room with original built ins, wainscoting, kitchen with plenty of cabinet space, original showcase stairs, oversized master bedroom with updated master bath, w/ cypress ceiling and walls w/ whirlpool. Upstairs is spacious and includes sitting area, 3BR/1BA. Original hardwood floors can be found in most of home along with original built ins and 5 fireplaces. Outside boasts 1 acre with lots of room to grow. With a possible city zoning change, this would make a great office. This home is being sold AS IS.

729 Main St, Chipley, FL 32428 is a 4 bedroom, 2 bathroom, 2,971 sqft single-family home built in 1925. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $343,100, with a rent estimate of $2,993/month.

Home Details for 729 Main St

Interior Features
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood
Appliances & Utilities Refrigerator
Heating & Cooling Air ConditioningCooling System: Central
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: MetalExterior: Other, Stucco, WoodPatio
Pool Pool
Parking & Garage GarageParking: Carport, Garage Attached

Property Information
Year Built Year Built: 1925Year Updated: 1972
Property Type / Style Property Type: Single Family HomeArchitecture: Craftsman

Community
Units in Building: 1

Lot Information
Lot Area: 1.01 acres

Price and Tax history

Date	Event	Price
Sep 8, 2016 Source: Agent Provided	ListingRemoved	$149,500
Mar 9, 2016 Source: Agent Provided	Listed For Sale	$149,500

Year	Property tax	Tax assessment
2025	$1,261	$284,511

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"
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
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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
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
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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
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 729 Main St

What is 729 Main St estimated to be worth?
Trulia's estimated value for 729 Main St in Chipley, FL is $343,100.
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 729 Main St?
The closest schools to 729 Main St in Chipley, FL are Chipley High School (rated 4/10), Kate M. Smith Elementary School (rated 4/10), Roulhac Middle School (rated 7/10).
Does 729 Main St have air conditioning?
Yes, 729 Main St in Chipley, FL has air conditioning.
Does 729 Main St have a pool?
Yes, 729 Main St in Chipley, FL has a pool.