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 4474 Osprey Dr estimated to be worth?

Trulia's estimated value for 4474 Osprey Dr in Chipley, FL is $246,700 .

What is the price history for 4474 Osprey Dr?

4474 Osprey Dr in Chipley, FL last sold for $128,900 in January 2008.

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 4474 Osprey Dr have air conditioning?

Yes, 4474 Osprey Dr in Chipley, FL has air conditioning.

How big is the lot at 4474 Osprey Dr?

The lot at 4474 Osprey Dr in Chipley, FL is about 3.6 acres .

OFF MARKET

$246,700

Trulia Estimate

3 Beds
3 Baths
1,980 sqft (on 3.55 acres)

4474 Osprey Dr, Chipley, FL 32428

Est. Refi. Payment $1,656/mo*

Refinance Your Home

Currently Off Market - Sold Jan 31, 2008 for $128,900

Home Value

Trulia Estimate

$247K

Since last month

$8K (-3.3%)

Since last year

$38K (-13.3%)

Since last sale

$118K (+91.2%)

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 +79% in the last 10 years

Month	Estimated value
2026
August 2026	$247K
August 2026	$246K
July 2026	$255K
June 2026	$260K
May 2026	$267K
April 2026	$262K
March 2026	$265K
February 2026	$257K
January 2026	$285K
2025
December 2025	$286K
November 2025	$266K
October 2025	$285K
September 2025	$284K
August 2025	$284K
July 2025	$296K
June 2025	$283K
May 2025	$277K
April 2025	$275K
March 2025	$274K
February 2025	$269K
January 2025	$266K
2024
December 2024	$271K
November 2024	$272K
October 2024	$291K
September 2024	$295K
August 2024	$290K
July 2024	$290K
June 2024	$297K
May 2024	$289K
April 2024	$284K
March 2024	$282K
February 2024	$273K
January 2024	$271K
2023
December 2023	$272K
November 2023	$271K
October 2023	$281K
September 2023	$283K
August 2023	$276K
July 2023	$280K
June 2023	$272K
May 2023	$273K
April 2023	$268K
March 2023	$261K
February 2023	$244K
January 2023	$236K
2022
December 2022	$246K
November 2022	$253K
October 2022	$255K
September 2022	$257K
August 2022	$258K
July 2022	$255K
June 2022	$252K
May 2022	$247K
April 2022	$239K
March 2022	$230K
February 2022	$213K
January 2022	$215K
2021
December 2021	$210K
November 2021	$209K
October 2021	$207K
September 2021	$203K
August 2021	$201K
July 2021	$197K
June 2021	$169K
May 2021	$127K
April 2021	$126K
March 2021	$119K
February 2021	$118K
January 2021	$122K
2020
December 2020	$121K
November 2020	$120K
October 2020	$121K
September 2020	$121K
August 2020	$121K
July 2020	$121K
June 2020	$120K
May 2020	$119K
April 2020	$118K
March 2020	$119K
February 2020	$118K
January 2020	$117K
2019
December 2019	$116K
November 2019	$115K
October 2019	$114K
September 2019	$114K
August 2019	$115K
July 2019	$116K
June 2019	$113K
May 2019	$114K
April 2019	$114K
March 2019	$113K
February 2019	$115K
January 2019	$119K
2018
December 2018	$109K
November 2018	$110K
October 2018	$123K
September 2018	$123K
August 2018	$123K
July 2018	$129K
June 2018	$126K
May 2018	$126K
April 2018	$129K
March 2018	$121K
February 2018	$120K
January 2018	$120K
2017
December 2017	$126K
November 2017	$133K
October 2017	$126K
September 2017	$136K
August 2017	$124K
July 2017	$129K
June 2017	$136K
May 2017	$133K
April 2017	$124K
March 2017	$122K
February 2017	$122K
January 2017	$122K
2016
December 2016	$125K
November 2016	$121K
October 2016	$118K
September 2016	$137K

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
3223 Quail Ridge Dr, Chipley, FL	0.35	Single-Family Home	$200,000	07/21/26	2	2	1,232
3399 Quail Ridge Dr, Chipley, FL	0.70	Single-Family Home	$475,000	04/20/26	4	3	2,294
4526 Leisure Lakes Dr, Chipley, FL	0.87	Single-Family Home	$322,000	08/28/26	4	2.5	2,180
3457 Quail Ridge Dr, Chipley, FL	0.73	Single-Family Home	$318,000	02/09/26	3	2	1,508
3376 Fawn Pl, Chipley, FL	1.20	Single-Family Home	$222,500	06/30/26	3	2	1,285
4904 Partridge Pl, Chipley, FL	0.92	Single-Family Home	$12,000	07/13/26	3	2	1,420
3320 Eagle Ct, Chipley, FL	1.36	Single-Family Home	$340,000	04/15/26	3	2	1,727
3361 Fawn Pl, Chipley, FL	1.24	Single-Family Home	$299,999	09/22/25	2	2	1,408
4427 Leisure Lakes Dr, Chipley, FL	1.26	Single-Family Home	$370,000	06/09/26	3	3	2,124
3520 Lodge Dr, Chipley, FL	0.70	Single-Family Home	$675,000	04/14/26	4	4	3,376

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
LOT 195 Whirlaway Ct #B, Chipley, FL 32428	0.10	-	-	-	-	Off Market
Quail Ridge Dr, Chipley, FL 32428	0.25	$69,500	-	-	-	For Sale
Quail Ridge Dr #B-251, Chipley, FL 32428	0.27	$70,000	-	-	-	For Sale
3243 Quail Ridge Dr, Chipley, FL 32428	0.31	$355,000	4	2	1,624	For Sale
B 216 Quail Ridge Dr, Chipley, FL 32428	0.31	$45,500	-	-	-	Recently Sold
A 126 Quail Ridge Dr, Chipley, FL 32428	0.38	$35,000	-	-	-	Recently Sold
Spendabuck Ct, Chipley, FL 32428	0.42	-	-	-	-	Off Market
Fox Ct, Chipley, FL 32428	0.38	$42,900	-	-	-	For Sale
3332 Quail Ridge Dr, Chipley, FL 32428	0.42	-	-	-	-	Off Market
4608 Dove Ct, Chipley, FL 32428	0.47	$445,700	3	2	1,711	Off Market
LOT 180 Spendabuck Ct #B, Chipley, FL 32428	0.50	-	-	-	-	Off Market
Quail Ridge Dr #B-156, Chipley, FL 32428	0.49	-	-	-	-	Off Market

Local Information

Map ViewExplore the area around 4474 Osprey Dr.
Schools1 Preschool School4 Elementary Schools4 Middle Schools4 High Schools
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1970

3.55 acre lot

1,980 sqft

$125/sqft

Garage

About this House

** REDUCED ** Large doublewide home in gated community on 3.79 acs. Lovely wooded area in private, peaceful location; Large storage building included. Has large spacious rooms that include a formal living room, formal dining room, den with fireplace, large modern kitchen with breakfast nook. Has 3 bedrooms and 2 and 1/2 baths. The half bath is located in utility room area. Had a front wooden deck, which has been removed,but has a small rear deck. Copy of old survey in file. Offered for CASH only and "Cash transactions are subject to special deed restrictions."<br/><br/>Brokered And Advertised By: CENTURY 21 Sunny South Properties<br/>Listing Agent: Ouida Morris

4474 Osprey Dr, Chipley, FL 32428 is a 3 bedroom, 3 bathroom, 1,980 sqft single-family home built in 1970. It last sold for $128,900 on Jan 31, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $246,700, with a rent estimate of $2,440/month.

Home Details for 4474 Osprey Dr

Exterior Features
Exterior Home Features Roof: CompositionExterior: Other
Parking & Garage GarageParking: Garage Detached

Property Information
Year Built Year Built: 1970Year Updated: 2002
Property Type / Style Property Type: Single Family Home

Interior Features
Heating & Cooling Air ConditioningCooling System: Central
Fireplace & Spa Fireplace
Levels, Entrance, & Accessibility Floors: Carpet

Community
Units in Building: 1

Lot Information
Lot Area: 3.55 acres

Price and Tax history

Date	Event	Price
Apr 21, 2011 Source: Agent Provided	ListingRemoved	$37,900
Apr 1, 2011 Source: Agent Provided	PriceChange	$37,900 Price decreased by 3%
Mar 15, 2011 Source: Agent Provided	Listed For Sale	$38,900
Jan 31, 2008 Source: N/A	Sold	$128,900
Feb 28, 2000 Source: N/A	Sold	$10,900

Year	Property tax	Tax assessment
2025	$613	$126,109

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
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"
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
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
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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 4474 Osprey Dr

What is 4474 Osprey Dr estimated to be worth?
Trulia's estimated value for 4474 Osprey Dr in Chipley, FL is $246,700.
What is the price history for 4474 Osprey Dr?
4474 Osprey Dr in Chipley, FL last sold for $128,900 in January 2008.
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 4474 Osprey Dr have air conditioning?
Yes, 4474 Osprey Dr in Chipley, FL has air conditioning.
How big is the lot at 4474 Osprey Dr?
The lot at 4474 Osprey Dr in Chipley, FL is about 3.6 acres.