Is a car needed in Winter Haven, FL?

As of early 2026, 83% of users say car is needed

Is parking easy in Winter Haven, FL?

As of early 2026, 80% of users say parking is easy

Are yards well-kept in Winter Haven, FL?

As of early 2026, 78% of users say yards are well-kept

Is Winter Haven, FL dog-friendly?

As of early 2026, 76% of users say it's dog friendly

Does Winter Haven, FL show holiday spirit?

As of early 2026, 68% of users say there's holiday spirit

Is Winter Haven, FL quiet?

As of early 2026, 64% of users say it's quiet

Do kids play outside in Winter Haven, FL?

As of early 2026, 61% of users say kids play outside

Would people walk alone at night in Winter Haven, FL?

As of early 2026, 49% of users say people would walk alone at night

Does Winter Haven, FL have sidewalks?

As of early 2026, 48% of users say there are sidewalks

Do residents of Winter Haven, FL plan to stay at least 5 years?

As of early 2026, 47% of users say they plan to stay for at least 5 years

Are the streets well-lit in Winter Haven, FL?

As of early 2026, 46% of users say streets are well-lit

Are neighbors friendly in Winter Haven, FL?

As of early 2026, 44% of users say neighbors are friendly

Is Winter Haven, FL walkable to grocery stores?

As of early 2026, 43% of users say it's walkable to grocery stores

Is there wildlife in Winter Haven, FL?

As of early 2026, 32% of users say there's wildlife

Is Winter Haven, FL walkable to restaurants?

As of early 2026, 30% of users say it's walkable to restaurants

Are there community events in Winter Haven, FL?

As of early 2026, 24% of users say there are community events

What is Pickney Dr estimated to be worth?

Trulia's estimated value for Pickney Dr in Winter Haven, FL is $263,200 .

Is Winter Haven a buyer's or seller's market?

Winter Haven is currently a balanced market, based on recent for-sale activity.

What's the median sale price in Winter Haven?

The median sale price in Winter Haven is $258K. That is down $2.5K from the prior month.

What do residents say about Winter Haven?

Residents describe Winter Haven, FL as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Winter Haven, FL .

How big is the lot at Pickney Dr?

The lot at Pickney Dr in Winter Haven, FL is about 0.26 acres (11,325 sq ft).

OFF MARKET

$263,200

Trulia Estimate

4 Beds
2 Baths
1,478 sqft (on 0.26 acres)

Pickney Dr, Winter Haven, FL 33881

Est. Refi. Payment $1,862/mo*

Refinance Your Home

Home Value

Trulia Estimate

$263K

Since last month

$7K (+2.7%)

Since last year

$118K (+81.4%)

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 +193% in the last 10 years

Month	Estimated value
2026
October 2026	$263K
September 2026	$253K
August 2026	$256K
July 2026	$254K
June 2026	$256K
May 2026	$254K
April 2026	$253K
March 2026	$253K
February 2026	$241K
January 2026	$243K
2025
December 2025	$260K
November 2025	$187K
October 2025	$174K
September 2025	$145K
August 2025	$165K
July 2025	$148K
June 2025	$176K
May 2025	$182K
April 2025	$176K
March 2025	$179K
February 2025	$185K
January 2025	$186K
2024
December 2024	$196K
November 2024	$183K
October 2024	$220K
September 2024	$198K
August 2024	$213K
July 2024	$228K
June 2024	$240K
May 2024	$220K
April 2024	$234K
March 2024	$230K
February 2024	$208K
January 2024	$199K
2023
December 2023	$209K
November 2023	$214K
October 2023	$216K
September 2023	$212K
August 2023	$216K
July 2023	$217K
June 2023	$221K
May 2023	$254K
April 2023	$241K
March 2023	$245K
February 2023	$250K
January 2023	$253K
2022
December 2022	$260K
November 2022	$263K
October 2022	$235K
2020
September 2020	$90K

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
2426 6TH ST NE, Winter Haven, FL	0.13	Single-Family Home	$30,000	03/03/26	3	2	1,447
2455 MARY JEWETT CIRCLE, Winter Haven, FL	0.15	Single-Family Home	$390,000	10/17/25	4	3	2,236
2303 S Swan Ct NE, Winter Haven, FL	0.37	Single-Family Home	$210,900	09/01/26	3	2	1,536
2438 4TH STREET NE, Winter Haven, FL	0.18	Single-Family Home	$245,000	05/15/26	3	2	1,135
316 LAKE SMART CIRCLE, Winter Haven, FL	0.35	Single-Family Home	$260,000	09/17/26	3	2	1,500
2015 6TH STREET NE, Winter Haven, FL	0.38	Single-Family Home	$248,000	09/03/26	3	2	1,542
2118 EDWIN, Winter Haven, FL	0.32	Single-Family Home	$237,900	02/11/26	3	2	1,215
343 LAKE SMART CIRCLE, Winter Haven, FL	0.37	Single-Family Home	$295,000	04/23/26	3	2	1,450
548 Martin Luther King Blvd NE, Winter Haven, FL	0.44	Single-Family Home	$160,000	06/18/26	3	2.5	2,182
2209 9TH COURT NE, Winter Haven, FL	0.45	Single-Family Home	$178,000	09/09/26	3	1.5	1,261

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Price	Bed	Bath	Sqft	Status
LAKE ALFRED RD, WINTER HAVEN, FL 33881	-	-	-	-	Off Market
Crosstower Dr, Winter haven, FL 33881	-	-	-	528	Off Market
Brigham Rd, Winter haven, FL 33881	-	-	-	-	Off Market
Winter Ter, Winter Haven, FL 33881	-	Studio	-	-	Off Market
Winter Ter, Winter Haven, FL 33881	-	Studio	-	-	Off Market
Winter Ter, Winter Haven, FL 33881	-	Studio	-	-	Off Market
NW, Winter Haven, FL 33881	-	Studio	-	-	Off Market
Winter Ter, Winter Haven, FL 33881	-	Studio	-	-	Off Market
Winter Ter, Winter Haven, FL 33881	-	Studio	-	-	Off Market
Winter Ter, Winter Haven, FL 33881	-	Studio	-	-	Off Market
Winter Ter, Winter Haven, FL 33881	-	Studio	-	-	Off Market
NW, Winter Haven, FL 33881	-	Studio	-	-	Off Market
DUNDEE ROAD, Winter Haven, FL 33881	-	-	-	-	Off Market
Sage Rd, Winter Haven, FL 33881	-	-	-	-	Off Market
Palm Nut Dr, Winter Haven, FL 33881	-	-	-	-	Off Market
INMAN DR NW, Winter Haven, FL 33881	-	-	-	-	Off Market
Lake Dr NW, Winter Haven, FL 33881	-	-	-	-	Off Market
0 Lake Cannon Dr, Winter Haven, FL 33881	-	-	-	-	Off Market
Palm Nut Dr #9-10, Winter Haven, FL 33881	-	-	-	-	Off Market
Pinewood Ln, Winter Haven, FL 33881	-	2	-	1,520	Off Market

Local Information

Map ViewExplore the area around Pickney Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

0.26 acre lot

1,478 sqft

$178/sqft

About this House

UNDER CONSTRUCTION ~ Quality built home by Legendary Construction set to be complete July 2017. There are 4 bedrooms and 2 full bathrooms with a split bedroom floor plan. There is still time to choose architectural elements as well as choose paint colors, cabinets, and flooring!

Pickney Dr, Winter Haven, FL 33881 is a 4 bedroom, 2 bathroom, 1,478 sqft single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $263,200, with a rent estimate of $2,003/month.

Home Details for Pickney Dr

Property Information
Property Type / Style Property Type: Single Family HomeArchitecture: Other

Exterior Features
Exterior Home Features DeckPatioPorch

Lot Information
Lot Area: 0.26 acres

Price and Tax history

Date	Event	Price
Apr 26, 2017 Source: Agent Provided	ListingRemoved	$170,000
Apr 21, 2017 Source: Agent Provided	PriceChange	$170,000 Price decreased by 6%
Jan 14, 2017 Source: Agent Provided	PriceChange	$180,000 Price increased by 13%
Nov 8, 2016 Source: Agent Provided	Listed For Sale	$160,000

Additional Cost

Market trends in Winter Haven

Last updated August 2026

Avg. sale price

$258K

$2.5KMoM

Sale-to-List Price

98.3%

0.1%MoM

Price per sq ft

$160

$1MoM

Available listings

771

7MoM

Around this home

Elbert Elementary School
PK-5
Public
729 Students
Polk County Public Schools
2/10
GreatSchools Rating
Parent Rating Average
The worst experience I’ve had with a school. I understand they had to change facilities and everyone was acclimating to the change, but that does not excuse the lack of communication. My daughter’s teacher was fantastic and excellent at communicating (she of course went to another school). My son’s teacher changed and I never heard anything from his new teacher. He was harmed regularly at school by other kids because the teacher had zero control. He was stabbed in the face by another child with a pencil and the office called me to tell me. They told me the teacher would be calling to explain and she never did. I hope in the future they’re able to better staff the school so teachers aren’t so overwhelmed, but I wouldn’t recommend this school.
Parent Review
2y 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 Winter Haven

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.

68% say there's holiday spirit
48% say there are sidewalks
44% say neighbors are friendly

Trulia Trick or TreatStart Ghost Hunt

At least 800 Trulia users voted on each feature.

83 % Say car is needed
80 % Say parking is easy
78 % Say yards are well-kept
76 % Say it's dog friendly
68 % Say there's holiday spirit
64 % Say it's quiet
61 % Say kids play outside
49 % Say people would walk alone at night
48 % Say there are sidewalks
47 % Say they plan to stay for at least 5 years
46 % Say streets are well-lit
44 % Say neighbors are friendly
43 % Say it's walkable to grocery stores
32 % Say there's wildlife
30 % Say it's walkable to restaurants
24 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Cathyharris1222
Resident
2mo ago
"Safe area for children and families "
0
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Cocobrownie3
Resident
5mo ago
"Freindly neighbors, Holloween is wonderful here, everyone loves to BBQ , and Santa Clause comes on Chismas Eve. Wonderful place to live. However, to schools are not so good. "
0
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William David Evans
Resident
1y ago
"We have our personal cars have used uber a few times but not really necessary for us because we live close to most of the stores and restaurants "
1
Flag
Morgan Ivey-trask
Resident
1y ago
"Everyone is friendly and so nice. I like it here but I will be moving out soon to live in North Carolina to get my kids back and live a new life "
2
Flag
Madeline R
Resident
1y ago
"Its neighborly and quiet while still being close to the theme parks and airport. Ive lived here for 5 years and it was the best decision we made."
0
Flag
Miguel Catalano
Resident
1y ago
"Quiet neighborhood, everything you need is close by and affordable, and places of worship for everyone. Light traffic all the time and great restaurants all over town with views of the lake. Serenity is everywhere in Winter Haven."
0
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Z64p52x99r
Resident
1y ago
"I don’t go to the community events in the area I solely go to work and home I enjoy this peace in the neighborhood "
0
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John Van Volkenburgh
Resident
2y ago
"Quick. No issues as long as you don’t work in Orlando or Tampa. Rural and central to the state. Small town. I’m "
0
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Jenna Strickler
Resident
2y ago
"Food giveaways, law enforcement always circling/passing by Security feels safe Not the best neighborhood overall, but I have not had an issue since living here. "
0
Flag
Emily Torres
Resident
2y ago
"I’ve lived close to this area for 3 years now and worked there for a year and a half. Very nice area !"
1
Flag
Anonymous
Resident
2y ago
"You can walk your dogs with no problems. Many houses are fenced. Dogs will bark but not bite. Dogs ca"
0
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Bianca Nieves
Resident
2y ago
"A lot of cats on the NE side of winter haven other than that winter haven lots of parks for children good schools "
4
Flag
Nicole Horton
Resident
2y ago
"I don’t feel safe for my 13 year old son to walk to the middle school by himself. I drive him and pick him up every day."
0
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Chris M
Resident
2y ago
"There is a farmers market every weekend. A lot of community activities every weekend. Christmas parade happened a few weekends ago. "
1
Flag
Yoflyboys
Resident
2y ago
"NW Winter Haven has turned into a dump site. Homeless has taken over bus stop. Inman park and the surrounding areas."
4
Flag
Oo7legend
Resident
5y ago
"Great for families to live in and feel part of a community. Needs more retailers, restaurants and higher rated schools."
30
Flag
April_stylist
Resident
5y ago
"Quiet hard working families, no issues with traffic or safety we love this area. Very friendly folks"
5
Flag
Angmartinez05
Resident
5y ago
"Not much to do in terms of attractions but safe everywhere. 45 min from either Orlando or Tampa. Friendly people "
0
Flag
Katia S.
Resident
6y ago
"I live there for 3 years ,it’s quiet,I don’t have any complaint against it.I recommend it for a start,no to stay for a long time .I live close to the park.i like it and I feel safe."
1
Flag
Atrollergirl
Prev. Resident
6y ago
"My commute is nice. I live 1 mile from Wahneta and I'm located near Bartow, Eagle Lake, Winter Haven."
0
Flag
Carly.m.williams
Prev. Resident
6y ago
"The area is a family friendly area. High traffic area also. Schools and shopping nearby. Legoland brings in a lot of traffic also"
0
Flag
Nakeem G.
Resident
6y ago
"My neighborhood in walking distance to a college, police station, farmers market, hair store, hospital/clinics and parks"
11
Flag
Joan
Resident
6y ago
"I live in this great neighborhood with great neighbors who get along. Quiet neighborhood. It feels safe."
0
Flag
Angela S.
Resident
6y ago
"Very busy front Street with big trucks daily passing by. Car speed a lot on the main road thru the area. "
0
Flag
Carly.m.williams
Resident
6y ago
"The area is very family friendly in my opinion. Never had any issues with neighbors. Quite a few stray cats but no issues."
0
Flag
Nancy F.
Resident
6y ago
"I see people walking there dogs daily. we have a dog park in the community very nice area they are allowed off the leash in the fenced in area, they can run and play freely, very friendly area for them all maintained spayed often to keep fleas away.. pet friendly area. "
1
Flag
Jennycomp
Prev. Resident
6y ago
"There are no sidewalks or places to walk your dogs. They are forced to use people’s yards and they get upset."
0
Flag
Gina K.
Resident
6y ago
"Halloween is great here!!! Trick or treating is like a giant party and there’s so much fun going on. "
0
Flag
Shelley P.
Resident
6y ago
"the downtown markets on 2and saturday, the water show @ lake howard things that go on at the church's and community centers n parks. I love Winter Haven I can go on and on just being able to walk lake"
22
Flag
Martha K.
Resident
6y ago
"My neighborhood is nice and quiet and their isn’t any crimes they maintain over here but sometimes the neighbors can be loud."
0
Flag
Shelley P.
Resident
6y ago
"traffic can be a little heavy on the main roads n have a tendency to speed thru the side streets. But overall the traffic is decent."
5
Flag
John D. B.
Resident
6y ago
"very quiet,peaceful...laid back family oriented neighborhoods... older community.... spirit lake road can get busy with traffic noice.... best to live away from spirit lake road.."
0
Flag
Basapooh81
Resident
6y ago
"Winter Haven holds a lot of community events. They have something going on mostly every weekend in downtown winter Haven. Winter Haven has Legoland park and water park also. "
10
Flag
Cdixon496
Resident
6y ago
"Dog owners would like the fact that there is plenty of open fields and place for the dogs to run around."
0
Flag
Victoria W.
Resident
6y ago
"Some people don’t pick up after their dogs and some dog parks aren’t well kept. You can walk your dog easily with a lot of sidewalks and areas to walk to"
14
Flag
Mp19601
Visitor
6y ago
"I just work around the area and every time i talk to sombody there nice and no complane for nothing...maybe i move in this area one fay"
0
Flag
Solomon G. .
Visitor
6y ago
"Yes it’s nice area to be in no issues what so ever I like it very much . Can’t say anything bad nor good "
1
Flag
Norma.G
Resident
7y ago
"Well the associated need to be more strict,and severe with the Owners each property, how they park at the street, not at the grass, do not allow any car on the side of street,they should park at there own driveway ,and the driving at the neighbors area should be limited speed,driving to fast can cause hitting someone."
0
Flag
DR
Resident
7y ago
"Work is minutes away. Hardly ever go anywhere but Orlando as I don’t feel theres anything to do around here."
0
Flag
Ctjohns34
Resident
7y ago
"Neighbors complain about walking dogs, dogs only recently became allowed in this community and some neighbors resist change "
0
Flag

LGBTQ Local Legal Protections

Frequently asked questions about Pickney Dr

What is Pickney Dr estimated to be worth?
Trulia's estimated value for Pickney Dr in Winter Haven, FL is $263,200.
Is Winter Haven a buyer's or seller's market?
Winter Haven is currently a balanced market, based on recent for-sale activity.
What's the median sale price in Winter Haven?
The median sale price in Winter Haven is $258K. That is down $2.5K from the prior month.
What do residents say about Winter Haven?
Residents describe Winter Haven, FL as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Winter Haven, FL.
How big is the lot at Pickney Dr?
The lot at Pickney Dr in Winter Haven, FL is about 0.26 acres (11,325 sq ft).