4239 Rolling Oaks Dr, Winter Haven, FL 33880
OFF MARKET

4239 Rolling Oaks Dr
Winter Haven, FL 33880

  • 1,332 sqft
1,332 sqft

Local Information

Map showing home location
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Description

" Lake View " *Lot Only* Very rare opportunity to purchase this lake view lot and have up to a year to place your dream home on it. After doing research I found a new 3/2 bath for 53,900. The approx. size home that will fit on this lot is a 28x55. Board of directors must approve any potential home prior to purchasing.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 4239 Rolling Oaks Dr

Property Information

Year Built
Year Built: 2018Year Updated: 1976
Property Type / Style
Property Type: Lot LandArchitecture: manufactured

Interior Features

Appliances & Utilities
Cable Ready

Exterior Features

Parking & Garage
Parking: Carport

Community

Units in Building: 1

Lot Information

Lot Area: 4560 sqft

Building

Fitness & Sports
Tennis Court

Price History for 4239 Rolling Oaks Dr

DatePriceEventSource
11/15/2016$26,000ListingRemovedAgent Provided
11/07/2016$26,000PendingAgent Provided
08/06/2015$26,000Listed For SaleAgent Provided
07/21/2015$23,000Sold
N/A
06/29/2015$23,000Listed For SaleAgent Provided

Market trends in Winter Haven

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$256K
$2.83KMoM
Sale-to-List Price
98.1%
0.4%MoM
Price per sq ft
$159
$1MoM
Available listings
767
7MoM
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Property Tax and Assessment

Year2025
Tax$376
Assessment$158,711
Home facts updated by county records

Homeowner tools

Estimated monthly rent$1,567/mo
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Homes for rent near 4239 Rolling Oaks Dr

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Comparable Sales for 4239 Rolling Oaks Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3130 Spirit Lake Rd, Winter Haven, FL
0.06
Lot/Land
$369,900
10/28/25
-
1,620
Lot 3130 Two Spirit Lake Rd, Winter Haven, FL
0.06
Lot/Land
$123,300
10/24/25
-
-
Lot 3130 Three Spirit Lake Rd, Winter Haven, FL
0.06
Lot/Land
$123,300
10/24/25
-
-
3130 Spirit Lake Rd #1, Winter Haven, FL
0.06
Lot/Land
$123,300
10/24/25
-
-
3130 Spirit Lake Rd #3, Winter Haven, FL
0.06
Lot/Land
$369,900
10/24/25
-
-
745 N 3rd St, Eagle Lake, FL
2.17
Lot/Land
$36,000
05/12/26
3
2
1,592
437 Archaic Dr #39, Winter Haven, FL
0.32
Lot/Land
$157,500
07/09/25
-
-
437 Archaic Dr, Winter Haven, FL
0.32
Lot/Land
$157,500
07/10/25
-
-
129 5th St, Winter Haven, FL
1.65
Lot/Land
$31,000
04/13/26
-
-
125 5th St, Winter Haven, FL
1.65
Lot/Land
$31,000
04/13/26
-
-

Nearby homes

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Assigned Schools

These are the assigned schools for 4239 Rolling Oaks Dr.
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

At least 798 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 streets are well-lit

  • 47 % Say they plan to stay for at least 5 years

  • 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.
  • 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 "
    1
    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
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  • 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
  • Mobreezwayz
    " schools are close by food near parks and recs are nice in the area. Fishing with in walking distance "
    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

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Off Market Homes Near 4239 Rolling Oaks Dr

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4239 Rolling Oaks Dr, Winter Haven, FL 33880 is a 1,332 sqft lot/land built in 2018. This property is not currently available for sale. 4239 Rolling Oaks Dr was last sold on Jul 21, 2015 for $23,000.