• 778 days on site
  • 5 views

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. Kitchen and tavern are leased. Have grants applied for in the millions to renovate it. Have insurance claim coming for a new roof as well.

Source: BRIGHT MLS, MLS#: VAFV2019018

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  • Property Type
    Commercial Sale
  • Lot
    3.88 acres

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Tami Imrich

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  • Median Age
    46
  • Population Density
    120
  • College Educated
    31%
  • Estimated Median Income
    $68,500
  • Estimated Total Home Owners
    1,208
  • Estimated Total Renters
    428
  • Owner / Renter Divide
    74% / 26%
  • Estimated Average Household Size
    3
  • Total Population
    4,321
  • Community data courtesy of LiveBy, Inc.

Owning this Home

$
$ %
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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

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Life at 7783 MAIN STREET


Schools


School data courtesy of LiveBy, Inc.
Ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating. The schools displayed on this website are for informational purposes only and may not represent a complete or up-to-date list. School assignments are subject to change and should be verified directly with the local school district. Please contact the appropriate school district to confirm school zoning and enrollment eligibility for this property.

History

Date Event Value Agent
12/17/2025Source: BRIGHT MLS Price Reduction
$1,300,000 -6.5%
9/9/2025Source: BRIGHT MLS Price Reduction
$1,390,000 -0.4%
6/21/2025Source: BRIGHT MLS Price Increase
$1,395,000 0.7%
12/3/2024Source: BRIGHT MLS Price Reduction
$1,350,000 -3.6%
12/3/2024Source: BRIGHT MLS Price Reduction
$1,385,000 -0.4%
12/3/2024Source: BRIGHT MLS Price Increase
$1,390,000 3.0%
12/3/2024Source: BRIGHT MLS Added to Database
May 13, 2024
Listing provided courtesy of RE/MAX Allegiance- MLS# VAFV2019018MLS ProviderContact Information: 7038244800

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