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Back 4135 Rolling Oaks Drive
Off Market

4135 Rolling Oaks Drive

Winter Haven FL 33880

2
2
1
1248 sq. ft.
3680 sq. ft.
Other
Last sold for $117,000
Jody PaganJody Pagan, last sold this property on 05 May 2026 after 103 days on market.

Overview

Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable Oakwood Estates, a gated 55+ community in Winter Haven. This home features a spacious open floor plan with a comfortable living and dining area, perfect for everyday living and entertaining. The kitchen offers ample cabinetry and counter space with a functional layout. The primary suite includes dual walk-in closets and an ensuite bath with dual sinks and a separate shower area. A generously sized guest bedroom and second full bath provide comfort for visitors. Enjoy relaxing on the covered porch, plus the convenience of a carport with covered parking and an attached storage shed. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates offers an active lifestyle with community amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant 55+ community.

Features

2 bedrooms
2 bathrooms
1 carspace
1 carport space
1248 sq. ft. floor area
3680 sq. ft. lot size
Other

Estimated Value

Based on this property and similar 2 bedroom other properties sold in Winter Haven over the last 12 months, the estimated median property value of 4135 Rolling Oaks Drive is $108k.

Median value
$108k
Estimated value range
$40k - $220k
Median days on market
84
Estimated value trend
-8%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Winter Haven. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 4135 Rolling Oaks Drive

2026
Sold
$117,000
05 May 2026 by Jody Pagan, of LA ROSA REALTY PRESTIGE
2014
Sold
$48,500
09 Apr 2014 by Kathy Newell, of Exit Realty of Lakeland

Happy sellers in Winter Haven

79%
79% of sellers in Winter Haven reported that their sale price either exceeded or met their price expectations.

Winter Haven stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 15 reviews in Winter Haven over the last 12 months.

Local market activity for 2 bedroom other properties in Winter Haven

In the last 12 months, 40 two-bedroom other properties similar to 4135 Rolling Oaks Drive, have been sold.

This represents a 41% decrease in two-bedroom other properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winter Haven

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Cheryl Brewer

Sellers who recommend Cheryl Brewer have praised them for being local expert, clear communication, responsive, dedicated, reliable, detail-oriented, and patient

  •   5   (129 reviews)
  •  2 Reviews in Winter Haven
  •  4 Sales in Winter Haven
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Cyleste Goodson

Cyleste Goodson is an award winning recommended agent for Winter Haven.  They have 2 local sales and collected 2 local reviews across the last 12 months.

  •   5   (114 reviews)
  •  2 Reviews in Winter Haven
  •  2 Sales in Winter Haven
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Kimberly Saddler

Kimberly Saddler is a recommended agent for Winter Haven.  They have 1 local sale and collected 2 local reviews across the last 12 months.

  •   5   (7 reviews)
  •  2 Reviews in Winter Haven
  •  1 Sale in Winter Haven
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Kathy Devor

Kathy Devor is a recommended agent for Winter Haven.  They have 24 local sales and collected 1 local review across the last 12 months.

  •   4.9   (12 reviews)
  •  1 Review in Winter Haven
  •  24 Sales in Winter Haven
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