4237 Rolling Oaks Dr, Winter Haven, FL 33880
Property image
Property image
OFF MARKET

4237 Rolling Oaks Dr
Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,032 sqft

$153,300

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $1,047/mo*
Refinance Your Home

$153,300

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $1,047/mo*
Refinance Your Home
2 Beds
2 Baths
1,032 sqft

Home Value

Trulia Estimate
$153K
Since last month
Decreased$3K (-1.9%)
Since last year
Decreased$3K (-1.9%)
Since last sale
Increased$70K (+84.7%)
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 +201% in the last 10 years
MonthEstimated value
2026
August 2026$153K
July 2026$156K
June 2026$157K
May 2026$158K
April 2026$156K
March 2026$155K
February 2026$156K
January 2026$154K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
11 ROBIN LANE, Winter Haven, FL
0.23
Mobile / Manufactured
$69,000
03/06/26
2
2
1,056
4607 BALSAWOOD STREET, Winter Haven, FL
0.05
Mobile / Manufactured
$60,000
07/31/26
2
2
960
4034 ROLLING OAKS DRIVE, Winter Haven, FL
0.16
Mobile / Manufactured
$95,000
10/22/25
2
2
1,032
2115 Spirit Lake Rd, Winter Haven, FL
0.17
Mobile / Manufactured
$58,500
05/22/26
2
2
1,320
4908 ROSEWOOD STREET, Winter Haven, FL
0.12
Mobile / Manufactured
$108,000
07/08/26
2
2
1,056
4027 ROLLING OAKS DRIVE, Winter Haven, FL
0.12
Mobile / Manufactured
$65,000
08/14/26
2
2
1,200
4067 ROLLING OAKS DRIVE, Winter Haven, FL
0.28
Mobile / Manufactured
$85,000
12/23/25
2
1.5
992
4102 SPRUCEWOOD STREET, Winter Haven, FL
0.15
Mobile / Manufactured
$68,500
09/03/25
2
1.5
768
4118 SPRUCEWOOD STREET, Winter Haven, FL
0.22
Mobile / Manufactured
$110,000
04/10/26
2
2
1,114
4109 SPRUCEWOOD STREET, Winter Haven, FL
0.22
Mobile / Manufactured
$65,000
06/09/26
2
2
1,176

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
4606 BALSAWOOD STREET, Winter Haven, FL 33880
0.03
$124,500
2
2
1,248
Off Market
4234 ROLLING OAKS DRIVE, Winter Haven, FL 33880
0.02
$139,900
2
2
1,804
For Sale
4607 BALSAWOOD STREET, Winter Haven, FL 33880
0.05
$60,000
2
2
960
Recently Sold
4704 DOGWOOD STREET, Winter Haven, FL 33880
0.07
$116,600
2
2
1,152
Off Market
4710 DOGWOOD STREET, Winter Haven, FL 33880
0.06
$96,200
2
2
1,440
Off Market
4017 ROLLING OAKS DRIVE, Winter Haven, FL 33880
0.09
-
2
2
1,056
Off Market
3131 SPIRIT LAKE ROAD LOT 17, Winter Haven, FL 33880
0.03
$94,900
-
-
-
For Sale
3128 SPIRIT LAKE ROAD, Winter Haven, FL 33880
0.07
$189,000
2
1
592
Off Market
3130 SPIRIT LAKE ROAD LOT 3, Winter Haven, FL 33880
0.07
$369,900
-
-
-
Recently Sold
3130 - Lot 1 SPIRIT LAKE ROAD LOT 1, Winter Haven, FL 33880
0.07
$123,300
-
-
-
Recently Sold
3130 - Lot 2 SPIRIT LAKE ROAD LOT 2, Winter Haven, FL 33880
0.07
$123,300
-
-
-
Recently Sold
3130 - Lot 3 SPIRIT LAKE ROAD LOT 3, Winter Haven, FL 33880
0.07
$123,300
-
-
-
Recently Sold

Local Information

  • Map ViewExplore the area around 4237 Rolling Oaks Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Mobile/Manufactured
Year Built
1981
Living Area
1,032 sqft
Price/Sqft
$149

About this House

"Water front" Picture yourself on a warm summer day ,In your Florida Room which over looks lake with a glass of tea, Just waiting to view the beautiful sunset right from your front roll seat! This beautiful water front home has been remodeled with blk diamond granite counter tops, membrane roof with life time warranty less than 2 years,Plaster walls rounded with texture, warranty on roof can be transferred for $395.00 to new owners, C/H/A less than two years. Plaster walls with rounded corner's through out. Rear Florida room that over looks the lake.From The time you walk through the front door you feel at home in this gorgeous home and can watch years of Florida sunsets right from your Florida Room.Located in a five star, gated park with low maintenance! This is a water Front, Home is a co op so public record's do not reflect waterfront!
4237 Rolling Oaks Dr, Winter Haven, FL 33880 is a 2 bedroom, 2 bathroom, 1,032 sqft mobile/manufactured built in 1981. It last sold for $83,000 on Dec 1, 2009. It is currently off market. The Trulia Estimate is $153,300, with a rent estimate of $1,538/month.

Home Details for 4237 Rolling Oaks Dr

Property Information

Year Built
Year Built: 1981Year Updated: 1981
Property Type / Style
Property Type: Mobile ManufacturedArchitecture: manufactured

Exterior Features

Pool
Pool
Parking & Garage
Parking Spaces: 2Parking: Carport

Community

Units in Building: 1

Lot Information

Lot Area: 6612 sqft

Price and Tax history

DateEventPrice
Apr 18, 2019
Source: Agent Provided
ListingRemoved
$114,900
Mar 18, 2019
Source: Agent Provided
Listed For Sale
$114,900
Dec 1, 2009
Source: N/A
Sold
$83,000
Sep 28, 2007
Source: N/A
Sold
$72,000

Market trends in Winter Haven

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$260K
$3.28KMoM
Sale-to-List Price
98.4%
0.2%MoM
Price per sq ft
$161
$4MoM
Available listings
778
10MoM

Around this home

What Locals Say about Winter Haven

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
    "Safe area for children and families "
    0
    Flag
  • Cocobrownie3
    "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
    Flag
  • William David Evans
    "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
    "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
    "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
    "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
    Flag
  • Z64p52x99r
    "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
    Flag
  • John Van Volkenburgh
    "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
    Flag
  • Jenna Strickler
    "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
    "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
    "You can walk your dogs with no problems. Many houses are fenced. Dogs will bark but not bite. Dogs ca"
    0
    Flag
  • Bianca Nieves
    "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
    "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
    Flag
  • Chris M
    "There is a farmers market every weekend. A lot of community activities every weekend. Christmas parade happened a few weekends ago. "
    1
    Flag
  • Yoflyboys
    "NW Winter Haven has turned into a dump site. Homeless has taken over bus stop. Inman park and the surrounding areas."
    4
    Flag
  • Oo7legend
    "Great for families to live in and feel part of a community. Needs more retailers, restaurants and higher rated schools."
    30
    Flag
  • April_stylist
    "Quiet hard working families, no issues with traffic or safety we love this area. Very friendly folks"
    5
    Flag
  • Angmartinez05
    "Not much to do in terms of attractions but safe everywhere. 45 min from either Orlando or Tampa. Friendly people "
    0
    Flag
  • Katia S.
    "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
    "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
    "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.
    "My neighborhood in walking distance to a college, police station, farmers market, hair store, hospital/clinics and parks"
    11
    Flag
  • Joan
    "I live in this great neighborhood with great neighbors who get along. Quiet neighborhood. It feels safe."
    0
    Flag
  • Angela S.
    "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
    "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.
    "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
    "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.
    "Halloween is great here!!! Trick or treating is like a giant party and there’s so much fun going on. "
    0
    Flag
  • Shelley P.
    "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.
    "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.
    "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.
    "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
    "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
    "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.
    "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
    "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. .
    "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
    "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
    "Work is minutes away. Hardly ever go anywhere but Orlando as I don’t feel theres anything to do around here."
    0
    Flag
  • Ctjohns34
    "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 4237 Rolling Oaks Dr

  • What is 4237 Rolling Oaks Dr estimated to be worth?
    Trulia's estimated value for 4237 Rolling Oaks Dr in Winter Haven, FL is $153,300.
  • What is the price history for 4237 Rolling Oaks Dr?
    4237 Rolling Oaks Dr in Winter Haven, FL last sold for $83,000 in December 2009.
  • 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 $260K. That is up $3.28K from the prior month.
  • Does 4237 Rolling Oaks Dr have a pool?
    Yes, 4237 Rolling Oaks Dr in Winter Haven, FL has a pool.
  • How big is the lot at 4237 Rolling Oaks Dr?
    The lot at 4237 Rolling Oaks Dr in Winter Haven, FL is about 0.15 acres (6,612 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 4237 Rolling Oaks Dr

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