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Back 4420 Bailey Road
Off Market

4420 Bailey Road

Willow Oak FL 33860

3
2
1
1723 sq. ft.
40001 sq. ft.
Single-Family
Last sold for $320,000
Kristin BrittKristin Britt, last sold this property on 23 June 2026 after 45 days on market.

Overview

Welcome home to peaceful country living with modern updates! This beautifully remodeled 3 bedroom, 2 bathroom home sits on nearly a full acre surrounded by majestic oak trees draped in classic Florida charm. From the moment you arrive, you’ll fall in love with the inviting curb appeal, mature landscaping, blooming gardenias, and tranquil setting. Inside, the open-concept layout creates the perfect space for entertaining and everyday living. The updated kitchen flows seamlessly into the spacious living area and features modern finishes, updated cabinetry, and plenty of room to gather. Updated flooring throughout the home adds a fresh, cohesive feel, while the thoughtfully renovated interior offers both comfort and style. Step outside and enjoy your own private slice of paradise with plenty of room to roam, garden, entertain, or simply relax under the shade of the gorgeous oak canopy. A charming chicken coop is already in place, making this property perfect for those dreaming of a little homestead lifestyle without sacrificing convenience. With no shortage of outdoor space, beautiful natural surroundings, and tasteful upgrades throughout, this property offers the ideal blend of country charm and modern living. Don’t miss your opportunity to own this unique and move-in ready retreat!

Features

3 bedrooms
2 bathrooms
1 carspace
1 carport space
1723 sq. ft. floor area
40001 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Willow Oak over the last 12 months, the estimated median property value of 4420 Bailey Road is $299.75k.

Median value
$299.75k
Estimated value range
$39.9k - $620k
Median days on market
35
Estimated value trend
-2%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Willow Oak. 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 4420 Bailey Road

2026
Sold
$320,000
23 Jun 2026 by Kristin Britt, of FONSECA WOOLFOLK REALTY LLC
2021
Sold
$249,900
16 Apr 2021 by Christina Moore, of KELLER WILLIAMS REALTY SMART

Happy sellers in Willow Oak

93%
93% of sellers in Willow Oak reported that their sale price either exceeded or met their price expectations.

Willow Oak stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 11 reviews in Willow Oak over the last 12 months.

Local market activity for 3 bedroom single-family properties in Willow Oak

In the last 12 months, 141 three-bedroom single-family properties similar to 4420 Bailey Road, have been sold.

This represents a 9% increase in three-bedroom single-family 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 Willow Oak

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Madison Zorn

Sellers who recommend Madison Zorn have praised them for being local expert, clear communication, responsive, patient, honest, dedicated, and supportive

  •   5   (65 reviews)
  •  2 Reviews in Willow Oak
  •  8 Sales in Willow Oak
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Christine Hubbert

Sellers who recommend Christine Hubbert have praised them for being responsive, local expert, clear communication, well-prepared, reliable, supportive, and stress-free process

  •   5   (114 reviews)
  •  2 Reviews in Willow Oak
  •  4 Sales in Willow Oak
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John Hubbert, Jr

Sellers who recommend John Hubbert, Jr have praised them for being local expert, responsive, clear communication, supportive, reliable, friendly, and dedicated

  •   5   (173 reviews)
  •  2 Reviews in Willow Oak
  •  3 Sales in Willow Oak
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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   (126 reviews)
  •  2 Reviews in Willow Oak
  •  3 Sales in Willow Oak
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