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sales rep | Brivity IDX

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7783 Main St , Middletown, VA 22645
$1,300,000
Est. Payment: $6,810.53/mo
20820 Sqft
3.88 Acres
Status: active | Days on site: 914
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RMAX127 - 47337,84381
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House Description

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 and doing great.

Highlights

Listed by Robert W Hotaling , 7036238666 and John M Hotaling , 7038674900 RE/MAX Allegiance , 7038244800. Bright MLS

Property Type

Commercial Sale

Lot/Acreage
3.88

Year Built

1797

County

Frederick

School District

Frederick County Public Schools

Listing ID

VAFV2019018

Questions about this listing?

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Interior Features

Appliances:Negotiable
Air Cond:Central A/C,Ceiling Fan(s)
Fireplaces:
Floor:Hardwood
Water:Public

Exterior Features

Lot:Adjoins - Public Land,Backs to Trees,Premium,Not New Construction,Horse Property: No,In City Limits
Garage Capacity:150
Zoning:B1
Roof:Metal,Flat
Others:
  • ▪ Additional:Excellent
Sewer:Public Sewer
Parking Features:Paved Parking,Lighted Parking,Parking Lot,4+ Spaces,3+ Spaces,2+ Spaces,1+ Spaces
Principal Interest
$6,811
Taxes
$103

Home Price

$1,300,000

Loan Details

30 yrs
6.844%

Down Payment

20%
$260,000
All calculations are estimates and provided by Blueroof360. Today’s Rates provided by Blueroof360. Information and interactive calculators are made available to you only as self-help tools for your independent use and are not intended to provide investment or tax advice. We cannot and do not guarantee their applicability or accuracy in regards to your individual circumstances. All examples are hypothetical and are for illustrative purposes. We encourage you to seek personalized advice from qualified professionals regarding all personal finance issues.
Monthly Price:
$6,810.53

Principal

Taxes

Principal Taxes HOA Total
Monthly $6,810.53 $102.83 $0.00 $6,913.36
Yearly $81,726.37 $1,234.00 $0.00 $82,960.37
Total $2,451,791.22 $37,020.00 $0.00 $2,488,811.22
Lender profile image
Chico Gordy
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Market insight data is pulled from the same city as the listing being viewed (Middletown, VA).

The schools listed are within a 2-mile radius of the property; however, attendance is not guaranteed. Please contact the local school district to confirm zoning and enrollment options.

Information provided by Bright MLS, and is deemed reliable but not guaranteed accurate.

IDX service by Blueroof 360

Data last updated: 2026-11-13T17:14:43.000Z

© 2026 Bright MLS