4091 Rolling Oaks Dr, Winter Haven, FL 33880
Property image
Property image
OFF MARKET

4091 Rolling Oaks Dr
Winter Haven, FL 33880

  • 2 Beds
  • 2 Baths
  • 1,464 sqft

$120,000

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $838/mo*
Refinance Your Home

$120,000

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $838/mo*
Refinance Your Home
2 Beds
2 Baths
1,464 sqft

Local Information

  • Map ViewExplore the area around 4091 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
1987
Living Area
1,464 sqft
Price/Sqft
$82

About this House

WELL CARED FOR HOME,HOME HAS PARTIAL DRYWALL TEXTURED WALLS, UP DATED WINDOWS, NEWER FLOORING. HOME IS A VERY OPEN FLOOR PLAN.YOU WILL FALL IN LOVE WITH THIS HOME FROM THE MOMENT YOU WALK THROUGH THE DOOR. LOCATED IN A FIVE STAR PARK,55 PLUS GATED COMMUNITY,TWO CLUB HOUSES,TWO HEATED POOLS,MINIATURE GOLF,SHUFFLE BOARD,HORSE SHOES,BOCCE BALL,FISHING PIER,PICKLE BALL, PLUS PLANNED DAILY ACTIVITIES.MOST OF FURNITURE IN HOME SELLER WILL BE TAKING,THERE WILL BE SOME FURNITURE LEFT.
4091 Rolling Oaks Dr, Winter Haven, FL 33880 is a 2 bedroom, 2 bathroom, 1,464 sqft mobile/manufactured built in 1987. It last sold for $69,900 on Jun 26, 2014. It is currently off market. The Trulia Estimate is $120,000, with a rent estimate of $1,597/month.

Home Details for 4091 Rolling Oaks Dr

Exterior Features

Exterior Home Features
Roof: OtherPatio
Parking & Garage
Parking Space: 1Parking: Carport

Property Information

Year Built
Year Built: 1987Year Updated: 1987
Property Type / Style
Property Type: Mobile ManufacturedArchitecture: Other

Interior Features

Interior Details
Number of Rooms: 3
Appliances & Utilities
DishwasherRefrigerator
Heating & Cooling
Air ConditioningCooling System: Central
Levels, Entrance, & Accessibility
Floors: Carpet, Linoleum Vinyl

Community

Units in Building: 1

Lot Information

Lot Area: 3680 sqft

Price History for 4091 Rolling Oaks Dr

DatePriceEventSource
03/28/2019$74,900ListingRemovedAgent Provided
03/20/2019$74,900Listed For SaleAgent Provided
06/26/2014$69,900Sold
N/A
05/06/2014$74,900Listed For SaleAgent Provided

Market trends in Winter Haven

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$257K
Sale-to-List Price
98.2%
Price per sq ft
$158
$2MoM
Available listings
767
3MoM
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Property Tax and Assessment

Year2025
Tax$437
Assessment$109,573
Home facts updated by county records

Comparable Sales for 4091 Rolling Oaks Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4090 ROLLING OAKS DRIVE, Winter Haven, FL
0.02
Mobile / Manufactured
$115,000
12/03/25
2
2
1,344
4319 CHERRYWOOD STREET, Winter Haven, FL
0.18
Mobile / Manufactured
$60,000
04/24/26
2
2
1,488
4250 CEDARWOOD STREET, Winter Haven, FL
0.09
Mobile / Manufactured
$92,500
04/06/26
2
2
1,200
4115 ROLLING OAKS DRIVE, Winter Haven, FL
0.10
Mobile / Manufactured
$108,500
02/18/26
2
2
1,416
4113 ROLLING OAKS DRIVE, Winter Haven, FL
0.09
Mobile / Manufactured
$115,000
10/02/25
2
2
1,392
4077 ROLLING OAKS DRIVE, Winter Haven, FL
0.05
Mobile / Manufactured
$105,000
01/08/26
2
2
1,176
4109 SPRUCEWOOD STREET, Winter Haven, FL
0.18
Mobile / Manufactured
$65,000
06/09/26
2
2
1,176
4067 ROLLING OAKS DRIVE, Winter Haven, FL
0.10
Mobile / Manufactured
$85,000
12/23/25
2
1.5
992
4424 LIMEWOOD STREET, Winter Haven, FL
0.20
Mobile / Manufactured
$90,000
05/15/26
2
2
1,440
4142 SPRUCEWOOD STREET, Winter Haven, FL
0.07
Mobile / Manufactured
$106,000
12/02/25
2
2
1,104

Nearby homes

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Assigned Schools

These are the assigned schools for 4091 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 799 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.
  • 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
  • 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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Homes for sale near 4091 Rolling Oaks Dr

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Off Market Homes Near 4091 Rolling Oaks Dr

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