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 $500,000
Whitney LohrWhitney Lohr, last sold this property on 28 October 2025 after 128 days on market.

Overview

BUYER FINANCING FELL THROUGH! NEW ROOF being installed this week and home inspection done! Welcome to 18561 Winding Oaks Boulevard, a beautifully maintained 3-bedroom, 3-bathroom pool home with bonus spaces on a sprawling half-acre fenced lot in the highly desirable Autumn Oaks community of Hudson, Florida. This spacious single-family home offers over 2,900 square feet of bright, open-concept living space designed for everyday comfort and entertaining. From the moment you walk in, you’ll notice the thoughtful layout and natural light pouring in through large windows. The heart of the home features a generously sized living and dining area perfect for hosting gatherings or enjoying quiet nights in. The well-appointed kitchen overlooks the main living space and provides plenty of cabinetry and counter space, ideal for any home chef. The split floor plan offers privacy for all, with the primary suite tucked away and featuring its own bonus retreat—perfect for a home office, nursery, workout zone, or cozy sitting area. The en-suite bathroom includes dual vanities, a soaking tub, and a separate shower. Two additional guest bedrooms are oversized and share a convenient guest bath, while the third full bathroom offers easy access to the pool area. The bonus room is a standout feature with endless possibilities—use it as a home gym, playroom, craft room, media center, or even convert it into an additional bedroom. Whether you're working from home, entertaining guests, or just enjoying your own space, this layout adapts to your lifestyle. Step outside to your private outdoor oasis where you'll find a screened-in pool and covered lanai perfect for relaxing weekends, summer cookouts, or evening swims. The backyard is fully fenced and pet-friendly, with ample room for gardening, play equipment, or simply enjoying nature. The property sits on a quiet street within Autumn Oaks, a deed-restricted community known for its mature landscaping, large lots, and welcoming feel. As a resident, you'll enjoy access to fantastic amenities including tennis courts, pickleball, a basketball court, a shaded playground, and picnic areas—all just a short stroll away. This location offers the best of both convenience and Gulf Coast charm, with Hudson Beach, waterfront dining, boat ramps, and SunWest Park just minutes away. Commuting is easy with quick access to the Suncoast Parkway and U.S. 19, making trips to Trinity, Tampa, Clearwater, or Spring Hill a breeze. You'll also appreciate the close proximity to top-rated schools, medical facilities, grocery stores, and shopping centers. Whether you're searching for a pool home in Hudson with space to grow, a peaceful retreat with no backyard neighbors, or a flexible floor plan that works for multigenerational living, 18561 Winding Oaks Blvd checks every box. Don’t miss the opportunity to own a well-cared-for home in one of Pasco County’s most popular communities. Schedule your private showing today and come see why so many buyers are choosing Autumn Oaks for its lifestyle, lot size, and unbeatable 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
48
Estimated value trend
-4%
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

2025
Sold
$500,000
28 Oct 2025 by Whitney Lohr, of BHHS FLORIDA PROPERTIES GROUP

Happy sellers in Shady Hills

90%
90% 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 35 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, 335 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.

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