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Back 18561 Winding Oaks Boulevard
Off Market

18561 Winding Oaks Boulevard

Shady Hills FL 34667

3
3
3
4216 sq. ft.
22865 sq. ft.
Single-Family
Last sold for $550,000
Colleen NolanColleen Nolan, last sold this property on 29 September 2026 after 98 days on market.

Overview

Virtually Staged. PRICED TO SELL | OVER ½ ACRE | SCREENED POOL | MOVE-IN READY Seller Financing Available and priced to sell, this beautifully remodeled executive pool home on over half an acre offers a rare opportunity in Autumn Oaks. Welcome to 18561 Winding Oaks Boulevard, an exceptional executive pool home nestled on over a half-acre in the highly sought-after Autumn Oaks community. Offering nearly 3,000 square feet of living space, this beautifully remodeled residence combines luxury, comfort, and modern updates throughout. Featuring 3 bedrooms, 3 bathrooms, and a spacious 3-car garage, this home is designed for both everyday living and entertaining. The open floor plan showcases luxury vinyl plank flooring throughout, updated finishes, and abundant natural light. Step outside to your private screened pool oasis overlooking the expansive fenced yard—perfect for relaxing or hosting family and friends. Enjoy peace of mind with a newer roof and countless upgrades that make this home truly move-in ready. All new pool equipment and heater. Located in one of Hudson's most desirable neighborhoods, Autumn Oaks is known for its oversized homesites, mature landscaping, and estate-style living while remaining convenient to shopping, dining, medical facilities, and the Suncoast Parkway. This rare opportunity offers the perfect blend of elegance, space, and modern updates in a premier location.

Features

3 bedrooms
3 bathrooms
3 carspaces
3 garage spaces
4216 sq. ft. floor area
22865 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Shady Hills over the last 12 months, the estimated median property value of 18561 Winding Oaks Boulevard is $313k.

Median value
$313k
Estimated value range
$90k - $910k
Median days on market
50
Estimated value trend
-1%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Shady Hills. 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 18561 Winding Oaks Boulevard

2026
Sold
$550,000
29 Sep 2026 by Colleen Nolan, of OFFERPAD BROKERAGE FL, LLC
2025
Sold
$500,000
28 Oct 2025 by Whitney Lohr, of BHHS FLORIDA PROPERTIES GROUP

Happy sellers in Shady Hills

91%
91% of sellers in Shady Hills reported that their sale price either exceeded or met their price expectations.

Shady Hills stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 29 reviews in Shady Hills over the last 12 months.

Local market activity for 3 bedroom single-family properties in Shady Hills

In the last 12 months, 338 three-bedroom single-family properties similar to 18561 Winding Oaks Boulevard, have been sold.

This represents a 14% 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 Shady Hills

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Gregory Klesius

Sellers who recommend Gregory Klesius have praised them for being local expert, responsive, clear communication, honest, reliable, supportive, and well-prepared

  •   5   (315 reviews)
  •  13 Reviews in Shady Hills
  •  12 Sales in Shady Hills
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Catherine "Cookie" Miller, PA, ABR, C2EX, CRS, DSC, GRI, MRP, SRES

Sellers who recommend Catherine "Cookie" Miller, PA, ABR, C2EX, CRS, DSC, GRI, MRP, SRES have praised them for being local expert, clear communication, responsive, supportive, dedicated, reliable, and attentive

  •   5   (86 reviews)
  •  5 Reviews in Shady Hills
  •  5 Sales in Shady Hills
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Cory Byrd

Cory Byrd is an award winning recommended agent for Shady Hills.  They have 19 local sales and collected 4 local reviews across the last 12 months.

  •   5   (27 reviews)
  •  4 Reviews in Shady Hills
  •  19 Sales in Shady Hills
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Kelly Reilly

Kelly Reilly is a recommended agent for Shady Hills.  They have 3 local sales and collected 4 local reviews across the last 12 months.

  •   5   (79 reviews)
  •  4 Reviews in Shady Hills
  •  3 Sales in Shady Hills
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