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listing
1 of 45
CommercialFor Sale
$1,390,000
7783 Main Street
Middletown, VA 22645
Listed by: Re/max Allegiance, 7036238666
MLS: Bright MLS
20,820Sq Ft
Est. Mortgage
$7,275/mo

Unlock the potential of a timeless landmark with the Wayside Inn, a historic gem nestled in the heart of Middletown, Virginia. This unique property not only boasts a rich history dating back to the 18th century but also offers 22 suites all with bathrooms, 3 bars (tavern, bourbon & Speakeasy, The RED HAT), huge entertaining space for events. This is a prime commercial opportunity with an expansive land for expansion. Just under 4 acres zoned B1. With 4 acres of commercially-zoned land at your disposal, envision the expansion possibilities that could elevate this historic landmark into a thriving hub of activity. Take advantage of the ample space to create a vibrant commercial district that complements the historic character of the Wayside Inn, making it a destination for locals and tourists alike. Situated in the picturesque Shenandoah Valley, the Wayside Inn offers a scenic backdrop that enhances the allure of any commercial venture. The expansive grounds provide ample room for outdoor amenities, gardens, or additional structures to further enhance the property's appeal. Benefit from the strategic location of Middletown, with easy access to major transportation routes. The Wayside Inn's proximity to popular attractions, historic sites, and a supportive local community makes it an ideal location for a successful and sustainable business venture. Don't miss the chance to own a piece of history with a promising future. The Wayside Inn presents a rare investment opportunity where historic charm meets commercial potential. Whether you're an entrepreneur seeking a unique venture or a developer with a vision, this property is your canvas to create something extraordinary.Seize the moment and transform the future of the Wayside Inn. Embrace the legacy, write the next chapter, and make this historic landmark a cornerstone of Middletown's thriving community. Fully running and doing great, we have changed management and its now positive cash flow. its prime for an owner occupant. call for details and appointments. Open to lease option and owner financing available.

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This data is up-to-date as of 12/01/2025 08:57 PM. Listing provided by Robert W Hotaling of Re/max Allegiance.
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