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HISTORIC HOMES (CENTRAL MD)

One of the most popular communities provided by Charis Realty Group

HISTORIC HOMES (CENTRAL MD)

About HISTORIC HOMES (CENTRAL MD)

Historic Homes for Sale in Central Maryland

(Pre-1940)

Whether you’re drawn to a circa-1800s farmhouse, a storybook Craftsman bungalow, or a stately Victorian with original details, Central Maryland offers a rare collection of homes that simply cannot be replicated today.

This curated search focuses exclusively on homes built prior to 1940 across Frederick, Carroll, Howard, Montgomery, and Washington Counties—properties rich in craftsmanship, character, and enduring architectural beauty. From wide-plank floors and hand-hewn beams to welcoming front porches and timeless proportions, these homes tell a story the moment you step inside.

Explore Historic Communities & Counties

Frederick County: A treasure trove of historic districts, including New Market, Frederick City, and Middletown—known for preserved streetscapes and beautifully restored homes.

Carroll County: Rolling farmland, charming small towns, and classic farmhouses with generous acreage and pastoral views.

Howard County: A unique blend of history and convenience, where older homes are tucked into established landscapes near modern amenities.

Montgomery County: From historic villages like Brookeville to early 20th-century homes in walkable communities, this area offers character close to DC.

Washington County: Rich in Civil War history, with stone homes, farmsteads, and properties that reflect deep Maryland heritage.

Why Choose a Historic Home?

Owning a historic home is about more than square footage—it’s about connection, craftsmanship, and legacy.

These homes often feature architectural details you won’t find in new construction, established settings with mature trees, solid materials and timeless design, and a sense of place, story, and permanence.

The Maryland Old House Collective Difference

The Maryland Old House Collective was created for those who see homes differently.

This is not a general home search—it’s a carefully curated experience designed for buyers and sellers who value vintage and historic architecture, thoughtful restoration and preservation, and unique, one-of-a-kind properties.

With over three decades of experience and a deep appreciation for older homes, this platform is built to help you discover, understand, and ultimately own a piece of Maryland’s history.

Real Estate Trends for Historic Homes

Historic homes continue to attract strong interest from buyers seeking character and individuality. While each property is unique, well-maintained and thoughtfully updated older homes often hold their value exceptionally well. Inventory tends to be limited, making these properties highly sought after when they come to market.

Start Your Search

Browse homes built prior to 1940 across Central Maryland and discover properties that offer more than a place to live—homes with character, history, and a story to carry forward.

One of the most popular communities provided by Charis Realty Group
742
# of Listings
3
Avg # of Bedrooms
$383
Avg. $ / Sq.Ft.
$721,711
Med. List Price

Browse HISTORIC HOMES (CENTRAL MD) Real Estate Listings

2 Properties Found. Page 1 of 1.

Location Location Location!  2.45 Acres comprised of 4 Lots with 3 income producing dwellings.  Site falls withing the Frederick County Comprehensive Plan for Commercial Uses.  Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC.  All Dwellings and Outbuildings are strictly as-is.
#VAFV2040748

WINCHESTER

821,829,839, and 851 FOX DRIVE

None Beds

None Baths

N/A

$1,499,000

MLS#: VAFV2040748

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.
#VAFV2019018

MIDDLETOWN

7783 MAIN STREET

None Beds

None Baths

20,820 Sq.Ft.

$1,300,000

MLS#: VAFV2019018

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