Sign up to have new listings emailed daily    Sign Up   Log In

7783 Main Street, Middletown, VA 22645

$1,300,000
  • 7783 Main Street, Middletown, VA 22645 Main Photo

45 Total Photos [Click to View All]

ACTIVE
MLS#VAFV2019018
STATUSACTIVE PROPERTY TYPECommercial - SCHOOLFREDERICK COUNTY PUBLIC SCHOOLS

Property 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.

7783 Main Street | MLS# VAFV2019018

This commercial property located at 7783 Main Street, Middletown, VA 22645 is currently listed for sale with an asking price of $1,300,000. Main Street is located within the FREDERICK COUNTY PUBLIC SCHOOLS school district. Search Middletown real estate on ynobles.montaguemiller.com today.

Property Features

Property Type: Commercial -
Cooling: Central A/C, Ceiling Fan(s)
Fuel Type: Natural Gas
Heating: Forced Air
Lot Size: 3.88 Acres
Roof Type: Metal, Flat
Taxes: $1,234
Year Built: 1797

Feature Descriptions

Accessibility: 36"+ wide Halls, Ramp - Main Level
Days on Site: 707
Electric: 3 Phases, 220 Volts
Exterior: Brick
Flooring: Hardwood
Lot: Adjoins - Public Land, Backs to Trees, Premium
Lot Dimensions: 3.88 Acre(S)
Parking Notes: Paved Parking, Lighted Parking
Sewer: Public Sewer
Special View Info: Mountain, Trees/Woods
Total Garage/Parking Spaces: 150
Water: Public

Local Schools

School District: FREDERICK COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: RE/MAX Allegiance
Agency Phone: 7038244800

Shown By

Agent Name: Yates Nobles
Agent Phone: (434) 996-0888
Agency Title: Montague Miller & Co. Realtors

IDX logo

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/20/2026. The listing information on this page last changed on 04/20/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 04/20/2026 12:00:29 AM EST) or CAAR MLS (last updated Sun 04/19/2026 11:10:07 PM EST) or Staunton MLS (last updated Sun 04/19/2026 11:40:13 PM EST) or HRAR MLS (last updated Sun 04/19/2026 11:29:00 PM EST) or Lynchburg MLS (last updated Sun 04/19/2026 9:32:43 PM EST) or Rockbridge, Lexington, Buena Vista MLS (last updated Sun 04/19/2026 4:00:05 PM EST) or Bright MLS (last updated Sun 04/19/2026 8:00:51 AM EST). Real estate listings held by brokerage firms other than Montague Miller & Co. Realtors may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
Privacy Policy / DMCA Notice / ADA Accessibility

Agency License Information: Montague, Miller & Co. is licensed in the state of Virginia.



Agent License Information: Licensed Associate Broker in the State of Virginia