# 7783 MAIN Street, Middletown, VA 22645 > **TL;DR:** other, $1,300,000. > A/C. Est. $6,953/mo. Listed 857 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,300,000 | | Lot Size | 169,013 sqft (3.88 acres) | | Property Type | Other (Other) | | Status | Active | | Days on Market | 857 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $6,574 | | Estimated Insurance | $379 | | **Total** | **$6,953** | ## Key Amenities - A/C ## Property Highlights - Built in 1797 - 3.88 acre lot - 150 parking spaces ## Description ### Agent 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. Have grants applied for in the millions to renovate it. Have insurance claim coming for a new roof as well. ## Location - **Address:** 7783 MAIN Street, Middletown, VA 22645 - **County:** FREDERICK - **Coordinates:** 39.0304, -78.27706 - **Google Maps:** https://www.google.com/maps?q=39.0304,-78.27706 ## Listing Agent - **Name:** Robert W Hotaling · **License:** 0255046378 - **Brokerage:** Allegiance Realty Partners, LLC - **Phone:** (703) 824-4800 - **Broker Phone:** (703) 824-4800 ## Photos ![7783 MAIN Street - Photo 1](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f169651362r.jpg) ![7783 MAIN Street - Photo 2](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f3512621504r.jpg) ![7783 MAIN Street - Photo 3](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f3612789033r.jpg) ![7783 MAIN Street - Photo 4](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1547708338r.jpg) ![7783 MAIN Street - Photo 5](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2230695260r.jpg) ![7783 MAIN Street - Photo 6](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f974528437r.jpg) ![7783 MAIN Street - Photo 7](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1736394992r.jpg) ![7783 MAIN Street - Photo 8](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1321591058r.jpg) ![7783 MAIN Street - Photo 9](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f917723042r.jpg) ![7783 MAIN Street - Photo 10](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1062790167r.jpg) ![7783 MAIN Street - Photo 11](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f129498274r.jpg) ![7783 MAIN Street - Photo 12](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f932973320r.jpg) ![7783 MAIN Street - Photo 13](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f7132560r.jpg) ![7783 MAIN Street - Photo 14](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f3237447092r.jpg) ![7783 MAIN Street - Photo 15](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2995962387r.jpg) ![7783 MAIN Street - Photo 16](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f4211874637r.jpg) ![7783 MAIN Street - Photo 17](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f3712456622r.jpg) ![7783 MAIN Street - Photo 18](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1906629120r.jpg) ![7783 MAIN Street - Photo 19](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2212102780r.jpg) ![7783 MAIN Street - Photo 20](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f3885553098r.jpg) ![7783 MAIN Street - Photo 21](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f3885553098r.jpg) ![7783 MAIN Street - Photo 22](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2218039176r.jpg) ![7783 MAIN Street - Photo 23](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f4144139265r.jpg) ![7783 MAIN Street - Photo 24](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f4222391203r.jpg) ![7783 MAIN Street - Photo 25](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f548221229r.jpg) ![7783 MAIN Street - Photo 26](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2210060495r.jpg) ![7783 MAIN Street - Photo 27](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2210060495r.jpg) ![7783 MAIN Street - Photo 28](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2659621534r.jpg) ![7783 MAIN Street - Photo 29](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2012769727r.jpg) ![7783 MAIN Street - Photo 30](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1264449848r.jpg) ![7783 MAIN Street - Photo 31](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f3125603377r.jpg) ![7783 MAIN Street - Photo 32](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2213890076r.jpg) ![7783 MAIN Street - Photo 33](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f3348694834r.jpg) ![7783 MAIN Street - Photo 34](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f806246280r.jpg) ![7783 MAIN Street - Photo 35](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1712878401r.jpg) ![7783 MAIN Street - Photo 36](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f3212116506r.jpg) ![7783 MAIN Street - Photo 37](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2732588039r.jpg) ![7783 MAIN Street - Photo 38](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f403583564r.jpg) ![7783 MAIN Street - Photo 39](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f2270935498r.jpg) ![7783 MAIN Street - Photo 40](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f4273439422r.jpg) ![7783 MAIN Street - Photo 41](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1587467901r.jpg) ![7783 MAIN Street - Photo 42](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f878053184r.jpg) ![7783 MAIN Street - Photo 43](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f60205382r.jpg) ![7783 MAIN Street - Photo 44](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1444479767r.jpg) ![7783 MAIN Street - Photo 45](http://lh.rdcpix.com/9c37c05d3772b14fc032c0900ffc608cl-f1216086095r.jpg) --- **MLS#:** VAFV2019018 | **Updated:** 2026-07-03 **Source:** listhub *Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/7783-main-street-middletown-va-22645-v2019018) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/7783-main-street-middletown-va-22645-v2019018#listing", "url": "https://www.propertysimple.ai/listing/7783-main-street-middletown-va-22645-v2019018", "name": "7783 MAIN Street, Middletown, VA 22645", "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. Have grants applied for in the millions to renovate it. 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