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Back 4077 Rolling Oaks Drive
Off Market

4077 Rolling Oaks Drive

Winter Haven FL 33880

2
2
1
1496 sq. ft.
3485 sq. ft.
Other
Last sold for $105,000
Patricia de GraaffPatricia de Graaff, last sold this property on 08 January 2026 after 288 days on market.

Overview

Back on market, property passed inspections! Welcome to Oakwood Estates, one of Winter Haven’s most sought-after 55+ co-op communities! This well-maintained home offers an inviting open floor plan with cathedral ceilings that make the living area feel bright, airy, and spacious. You’ll love the luxury vinyl plank flooring throughout the living area, hallway, and primary bedroom, easy to maintain and beautifully updated. The primary bedroom is oversized and features a fantastic walk-in closet with room for everything. Both the kitchen and primary bath have updated countertops, and the hall bath has a newer vanity for a fresh look. Off to the side, you’ll find an enclosed porch that adds great extra living space, complete with a separate workshop at the back, perfect for projects or storage, and neatly tucked away behind a closed door when guests stop by.Step out back and you’ll discover one of this home’s best features, a large deck overlooking open greenspace owned by the county, meaning you’ll have no rear neighbors building behind you. The roof-over adds extra insulation and the AC was replaced in 2019 for peace of mind. Some of the other updates include windows, skirting, siding and kitchen cabinets. This home will be sold mostly unfurnished, but the beds, living room TV stand, and generator will stay. Oakwood Estates is an active 55+ co-op community offering a long list of amenities including swimming, shuffleboard, tennis, horseshoes, and plenty of daily activities to enjoy. Don’t wait, call today for your private showing of this wonderful home and start enjoying the Florida lifestyle you’ve been waiting for!

Features

2 bedrooms
2 bathrooms
1 carspace
1 carport space
1496 sq. ft. floor area
3485 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 4077 Rolling Oaks Drive is $105.5k.

Median value
$105.5k
Estimated value range
$40k - $190k
Median days on market
88
Estimated value trend
-16%
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 4077 Rolling Oaks Drive

2026
Sold
$105,000
08 Jan 2026 by Patricia de Graaff, of RE/MAX HERITAGE PROFESSIONALS
2014
Sold
$38,900
02 Sep 2014 by RETA STEAD, of SOUTHERN BELLE REALTY

Happy sellers in Winter Haven

78%
78% 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 14 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, 39 two-bedroom other properties similar to 4077 Rolling Oaks Drive, have been sold.

This represents a 35% decrease in two-bedroom other properties sales when compared to the previous 12 months.

Nearby agents

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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

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Cyleste Goodson

Sellers who recommend Cyleste Goodson have praised them for being local expert, responsive, clear communication, honest, supportive, friendly, and patient

  •   5   (111 reviews)
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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
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