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 1444 Wolf Bay Rd estimated to be worth?

Trulia's estimated value for 1444 Wolf Bay Rd in Chipley, FL is $409,300 .

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 1444 Wolf Bay Rd?

The closest schools to 1444 Wolf Bay Rd in Chipley, FL are Chipley High School (rated 4/10), Kate M. Smith Elementary School (rated 4/10), Roulhac Middle School (rated 7/10).

OFF MARKET

$409,300

Trulia Estimate

3 Beds
2 Baths
1,881 sqft

1444 Wolf Bay Rd, Chipley, FL 32428

Est. Refi. Payment $2,738/mo*

Refinance Your Home

Home Value

Trulia Estimate

$409K

Since last month

$2K (+0.6%)

Since last year

$23K (+6.1%)

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 decreased by -3% in the last 10 years

Month	Estimated value
2026
September 2026	$409K
August 2026	$407K
July 2026	$414K
June 2026	$408K
May 2026	$399K
April 2026	$397K
March 2026	$417K
February 2026	$414K
January 2026	$388K
2025
December 2025	$350K
November 2025	$391K
October 2025	$385K
September 2025	$386K
August 2025	$378K
July 2025	$379K
June 2025	$407K
May 2025	$421K

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
220 Highway 77, Chipley, FL	1.29	Single-Family Home	$235,000	06/24/26	3	2	2,170
3721 Highway 77, Graceville, FL	1.61	Single-Family Home	$205,000	02/06/26	3	2	1,775
470 2nd St, Chipley, FL	1.97	Single-Family Home	$160,000	08/26/26	4	2	1,481
1264 Plum Ave, Chipley, FL	2.11	Single-Family Home	$292,000	03/26/26	3	2	1,425
1275 Morris Ave, Chipley, FL	2.26	Single-Family Home	$164,900	11/25/25	3	2	1,245
500 2nd St, Chipley, FL	2.08	Single-Family Home	$150,000	09/02/26	3	1	1,300
345 Carr Rd, Chipley, FL	2.21	Single-Family Home	$57,000	11/13/25	3	2	1,092
1239 Holley Ave, Chipley, FL	2.41	Single-Family Home	$194,500	08/11/26	2	2	1,338
632 Main St, Chipley, FL	2.47	Single-Family Home	$260,000	12/19/25	4	2	2,684
1342 Old Bonifay Rd, Chipley, FL	2.57	Single-Family Home	$130,000	10/10/25	3	2.5	1,896

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
59 Enfinger Rd, Chipley, FL 32428	0.30	$271,600	3	2	1,606	Off Market
1561 Snell Rd, Chipley, FL 32428	0.65	$350,000	3	2.5	2,763	For Sale
3646 Earlston Rd, Graceville, FL 32440	0.96	$59,400	3	2	1,392	Off Market
1353 Williams Rd, Chipley, FL 32428	1.17	$365,600	3	2	2,423	Off Market
220 Highway 77, Chipley, FL 32428	1.29	$235,000	3	2	2,170	Recently Sold
226 Highway 77, Chipley, FL 32428	1.30	$189,900	3	1	1,198	For Sale
541 Gum Creek Rd, Graceville, FL 32440	1.49	$232,200	3	1.5	1,731	Off Market
Cope Rd, Chipley, FL 32428	1.55	-	-	-	-	Off Market

Local Information

Map ViewExplore the area around 1444 Wolf Bay Rd.
Schools1 Preschool School4 Elementary Schools4 Middle Schools4 High Schools
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1998

1,881 sqft

$218/sqft

About this House

Picturesque and private turn key Horse Farm/Gentleman's Estate. The home sits atop a hill in the center of the 40 acre estate providing panoramic views of the emerald green pastures and two stocked fish ponds. You feel right at home in the large living room with a cozy brick wood burning fireplace with thermostatic controlled insert. The kitchen has an abundance of solid oak cabinets that picture frame all new appliances. There are three bedrooms, a large master suite with spacious master bath and a bonus room currently used for an office that could become a 4th bedroom. Relax and have a tall glass of ice tea on your back porch that is fully screened located near the deck of the 30 ft. swimming pool. The horse barn/full shop has 8 stalls and a concreted tack room and a man's dream insulated shop 24x36 with air. Pre-Qualified Buyers only. Brokered And Advertised By: SUNRISE NORTHWEST REALTY, INC. Listing Agent: Cindy Willis

1444 Wolf Bay Rd, Chipley, FL 32428 is a 3 bedroom, 2 bathroom, 1,881 sqft single-family home built in 1998. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $409,300, with a rent estimate of $1,892/month.

Home Details for 1444 Wolf Bay Rd

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

Price and Tax history

Date	Event	Price
May 9, 2013 Source: Agent Provided	ListingRemoved	$299,000
Mar 20, 2013 Source: Agent Provided	Pending	$299,000
Feb 17, 2013 Source: Agent Provided	PriceChange	$299,000 Price decreased by 15%
Aug 22, 2012 Source: Agent Provided	PriceChange	$350,000 Price decreased by 7%
Mar 7, 2012 Source: Agent Provided	Listed For Sale	$375,000

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. "
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."
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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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Frequently asked questions about 1444 Wolf Bay Rd

What is 1444 Wolf Bay Rd estimated to be worth?
Trulia's estimated value for 1444 Wolf Bay Rd in Chipley, FL is $409,300.
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 1444 Wolf Bay Rd?
The closest schools to 1444 Wolf Bay Rd in Chipley, FL are Chipley High School (rated 4/10), Kate M. Smith Elementary School (rated 4/10), Roulhac Middle School (rated 7/10).