4237 Roberta Dr, Winter Haven, FL 33881
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Property image
OFF MARKET

$285,500

Trulia Estimate
as of Sep 30, 2026
  • 3 Beds
  • 2 Baths
  • 1,711 sqft

4237 Roberta Dr, Winter Haven, FL 33881

Home Highlights

Single-Family Home
Built in 2018
1,711 sqft
$167/sqft
Garage

Local Information

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

About this House

Please note that the advertised price may exclude additional fees. These include a mandatory $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; fees for amenities like smart home or internet service; and optional conditional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99), pet fees/rent, or pool maintenance, if applicable. HOA application and amenity fees, where applicable, are paid directly to the HOA. Get rewarded for rental payments and more through FirstKey Homes Rewards - a rewarding and fun loyalty program. Get the home you want and the value you deserve with FirstKey Homes. Use our website to Apply Online, Schedule a Self-Tour, Review Resident Qualifications or Search More Homes; or contact our leasing department for help today. Pets are welcome. Apply soon, homes can go fast!

3 bedroom, 2 bathroom rental home in Winter Haven, FL, may be just the home for you.

 FirstKey Homes, LLC is an Equal Housing Lessor under the FHA. Applicable local, state and federal laws may apply. Lease terms and conditions apply. This is not an offer to rent—you must submit additional information for review and approval. Listed features may not be accurate; confirm details with a leasing representative. Certain cities and municipalities – including St. Louis and Chicago – require a home inspection prior to a new resident taking possession of the home. If you are leasing a home in one of these areas, please note that your move-in date could be adjusted to accommodate inspection requirements. Please ask your leasing agent for more details. BEWARE OF RENTAL SCAMS: FirstKey Homes exclusively manages our homes (no third-party management). We do not lease homes through Craigslist, SocialServe, LetGo, Facebook Marketplace or other classified advertising services. We will never ask for wire transfers, cash apps like Venmo, Zelle, CashApp PayPal, or any other transferring method to collect funds. See FirstKey Homes website for full details and conditions. Listing photos are provided to help you select a home; all photos shown are for representative and illustrative purposes only but may not be exact. Colors and photo size may vary based on different resolutions, hue, brightness, contrast, or other photo variations. Photos on websites may be modified, changed, or amended at any time. For new construction homes, actual homes may vary, photos may be of similar home/floorplan, home may be under construction and photos may not be of actual home, individual homes, amenities, features, and views may differ. If you have any concerns, please schedule a tour prior to applying or leasing the listed home.
4237 Roberta Dr, Winter Haven, FL 33881 is a 3 bedroom, 2 bathroom, 1,711 sqft single-family home built in 2018. It last sold for $330,000 on Jun 20, 2022 (20,919% above the $1,570 asking price). More recently, it was listed as a rental in September 2025 with an asking price of $1,570 per month. That rental listing was removed on September 17, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $285,500, with a rent estimate of $1,842/month.
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Home Details for 4237 Roberta Dr

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For DetailsAvailable: now

Interior Features

Appliances & Utilities
Disposal
Heating & Cooling
Air ConditioningCooling System: Central Air

Exterior Features

Parking & Garage
GarageParking: Garage

Comparable Sales for 4237 Roberta Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4250 ROBERTA DRIVE, Winter Haven, FL
0.04
Single-Family Home
$262,500
10/31/25
3
2
1,690 sqft
1199 SOPHIA BOULEVARD, Winter Haven, FL
0.11
Single-Family Home
$269,900
08/20/26
3
2
1,690 sqft
2213 ROSE BOULEVARD, Winter Haven, FL
0.04
Single-Family Home
$285,000
07/06/26
4
2
1,851 sqft
153 REBECCA DRIVE NE, Winter Haven, FL
0.15
Single-Family Home
$289,999
10/10/25
3
2
1,432 sqft
153 Rebecca Dr, Winter Haven, FL
0.15
Single-Family Home
$290,000
10/08/25
3
2
1,432 sqft
3034 SABAL BEND DRIVE NE, Winter Haven, FL
0.19
Single-Family Home
$240,500
04/09/26
3
2
1,514 sqft
1471 EAGLE CREST BOULEVARD, Winter Haven, FL
0.34
Single-Family Home
$315,000
06/18/26
4
2
1,755 sqft
2412 TWIN LAKE VIEW ROAD, Winter Haven, FL
0.38
Single-Family Home
$305,000
03/06/26
4
2
1,756 sqft
1400 EAGLE CREST BLVD, Winter Haven, FL
0.34
Single-Family Home
$335,000
03/30/26
4
2
2,169 sqft
2352 TWIN LAKE VIEW ROAD, Winter Haven, FL
0.45
Single-Family Home
$300,000
06/22/26
3
2
1,994 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Winter Haven

Last updated Sep 2026
Trulia Rent Estimate$1,842/mo
Average rent
$1.8K
$23MoM
Available listings
491
View rental market trends in Winter Haven, FL

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
Sep 17, 2025
Source: Zillow Rentals
ListingRemoved
$1,570
Sep 11, 2025
Source: Zillow Rentals
Listed For Rent
$1,570
Aug 26, 2025
Source: Zillow Rentals
ListingRemoved
$1,570
Aug 21, 2025
Source: Zillow Rentals
PriceChange
$1,570
Price decreased by 3%
Aug 14, 2025
Source: Zillow Rentals
PriceChange
$1,625
Price decreased by 4%

Frequently asked questions about 4237 Roberta Dr

  • What is 4237 Roberta Dr estimated to be worth?
    Trulia's estimated value for 4237 Roberta Dr in Winter Haven, FL is $285,500.
  • What is the price history for 4237 Roberta Dr?
    4237 Roberta Dr in Winter Haven, FL last sold for $330,000 in June 2022.
  • 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.
  • Does 4237 Roberta Dr have air conditioning?
    Yes, 4237 Roberta Dr in Winter Haven, FL has air conditioning.
  • Does 4237 Roberta Dr have a garage?
    Yes, 4237 Roberta Dr in Winter Haven, FL has a garage.

Homes for rent near 4237 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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