4258 Roberta Dr, Winter Haven, FL 33881
knockout_01152026
knockout_01152026
OFF MARKET

4258 Roberta Dr
Winter Haven, FL 33881

  • 4 Beds
  • 2 Baths
  • 1,748 sqft

$281,100

Trulia Estimate
as of Aug 20, 2026

$281,100

Trulia Estimate
as of Aug 20, 2026
  • 4 Beds
  • 2 Baths
  • 1,748 sqft

Home Highlights

Property Type
Single-Family Home
Year Built
2021
Living Area
1,748 sqft
Price/Sqft
$161
Parking
Garage

Local Information

  • Map ViewExplore the area around 4258 Roberta Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Winter Haven, FL - House - $1,950.00 Available January 2026
APPLY TODAY FOR FREE!! Welcome to 4258 Roberta Dr in Winter Haven, FL, a spacious and inviting rental home offering comfort, functionality, and a great location. This well designed property features 4 bedrooms, 2 bathrooms, and a 2 car garage, providing plenty of space for families or anyone needing extra room. Inside, you will find bright living areas, a well equipped kitchen, and comfortable bedrooms ideal for everyday living. Enjoy outdoor space perfect for relaxing or entertaining, all within a quiet neighborhood close to shopping, dining, schools, and major roadways. This is a wonderful opportunity to rent a beautiful home in the heart of Central Florida. Washer and dryer included!
4258 Roberta Dr, Winter Haven, FL 33881 is a 4 bedroom, 2 bathroom, 1,748 sqft single-family home built in 2021. It last sold for $290,000 on Dec 21, 2021 (14,772% above the $1,950 asking price). More recently, it was listed as a rental in January 2026 with an asking price of $1,950 per month. That rental listing was removed on March 14, 2026. It is currently off market. The Trulia Estimate is $281,100, with a rent estimate of $2,021/month.

Home Details for 4258 Roberta Dr

Property Information

Year Built
Year Built: 2021
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Interior Features

Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Air Conditioner, Ceiling Fan

Exterior Features

Parking & Garage
GarageParking: Garage, On Site

Additional Information

Smoke Free

Comparable Sales for 4258 Roberta Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2213 ROSE BOULEVARD, Winter Haven, FL
0.09
Single-Family Home
$285,000
07/06/26
4
2
1,851 sqft
4250 ROBERTA DRIVE, Winter Haven, FL
0.02
Single-Family Home
$262,500
10/31/25
3
2
1,690 sqft
153 REBECCA DRIVE NE, Winter Haven, FL
0.17
Single-Family Home
$289,999
10/10/25
3
2
1,432 sqft
153 Rebecca Dr, Winter Haven, FL
0.17
Single-Family Home
$290,000
10/08/25
3
2
1,432 sqft
1471 EAGLE CREST BOULEVARD, Winter Haven, FL
0.30
Single-Family Home
$315,000
06/18/26
4
2
1,755 sqft
2447 TWIN LAKE VIEW ROAD, Winter Haven, FL
0.34
Single-Family Home
$289,900
04/03/26
4
2
1,756 sqft
2412 TWIN LAKE VIEW ROAD, Winter Haven, FL
0.33
Single-Family Home
$305,000
03/06/26
4
2
1,756 sqft
1400 EAGLE CREST BLVD, Winter Haven, FL
0.28
Single-Family Home
$335,000
03/30/26
4
2
2,169 sqft
2363 TWIN LAKE VIEW ROAD, Winter Haven, FL
0.40
Single-Family Home
$290,000
11/10/25
4
2
1,822 sqft
3034 SABAL BEND DRIVE NE, Winter Haven, FL
0.24
Single-Family Home
$240,500
04/09/26
3
2
1,514 sqft

Nearby homes

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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

Price and Tax history

DateEventPrice
Mar 14, 2026
Source: Zillow Rentals
ListingRemoved
$1,950
Jan 17, 2026
Source: Zillow Rentals
Listed For Rent
$1,950
Dec 16, 2024
Source: Stellar MLS #O5986523
ListingRemoved
$299,900
Oct 20, 2024
Source: Zillow Rentals
ListingRemoved
$1,950
Oct 19, 2024
Source: Zillow Rentals
Listed For Rent
$1,950

Frequently asked questions about 4258 Roberta Dr

  • What is 4258 Roberta Dr estimated to be worth?
    Trulia's estimated value for 4258 Roberta Dr in Winter Haven, FL is $281,100.
  • What is the price history for 4258 Roberta Dr?
    4258 Roberta Dr in Winter Haven, FL last sold for $290,000 in December 2021.
  • 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 4258 Roberta Dr have air conditioning?
    Yes, 4258 Roberta Dr in Winter Haven, FL has air conditioning.
  • Does 4258 Roberta Dr have laundry facilities?
    Yes, 4258 Roberta Dr in Winter Haven, FL has in-unit laundry.

Homes for rent near 4258 Roberta Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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