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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

6 Properties Found. Page 1 of 1.

Great opportunity to acquire a profitable retail business with nearly 12,000SF of space.  Inventory can be included. Business assets also include two box trucks, forklift, shelving, stand-up coolers, two metal storage containers, and one wooden storage unit. The Stephens City Outlet Center has been a fixture on Main Street Stephens City for decades, selling clothing, homegoods, groceries, and seasonal items.  Traffic count of approximately 7,400 ADT, per VDOT. Prospective buyers must be financially qualified and sign our NDA before showings and sharing of financials.
#VAFV2036424

STEPHENS CITY

5307 MAIN STREET

None Beds

None Baths

11,848 Sq.Ft.

$875,000

MLS#: VAFV2036424

Historic 1800s farmhouse on 5 unrestricted acres just outside Winchester, Virginia, in desirable Frederick County. This 3-bedroom, 3-bath farmhouse blends historic charm with modern comfort and is equestrian-ready. Features include hardwood floors throughout, a farmhouse kitchen with wrap-around covered porch access, a dining room with a fireplace, a living room with a fireplace, and a den/office with built-in bookcases. The primary suite has a sitting area and a full bath.  Unfinished basement for storage.
Enjoy outdoor living with an inground pool, hot tub, and covered patio, perfect for entertaining. 
Horse amenities include a 40x30 barn with 2–4 stalls, an automatic waterer, and 8-strand high-tensile fencing (a small portion of fencing needed to fully enclose the back field).  Unrestricted acreage is ideal for horses, livestock, or hobby farming.  Conveniently located minutes from Old Town Winchester, shopping, restaurants, and farmers' markets.   A rare opportunity for historic farmhouse living, equestrian property, and peaceful country lifestyle near town.  All sizes are approximate. See documents for a list of home improvements - home has been well-maintained and updated.
#VAFV2040070

WINCHESTER

171 LAUREL GROVE ROAD

3 Beds

3 Baths

3,052 Sq.Ft.

$725,000

MLS#: VAFV2040070

Historic 1800s farmhouse on 5 unrestricted acres just outside Winchester, Virginia, in desirable Frederick County. This 3-bedroom, 3-bath farmhouse blends historic charm with modern comfort and is equestrian-ready. Features include hardwood floors throughout, a farmhouse kitchen with wrap-around covered porch access, a dining room with a fireplace, a living room with a fireplace, and a den/office with built-in bookcases. The primary suite has a sitting area and a full bath.  Unfinished basement for storage.
Enjoy outdoor living with an inground pool, hot tub, and covered patio, perfect for entertaining. 
Horse amenities include a 40x30 barn with 2–4 stalls, an automatic waterer, and 8-strand high-tensile fencing (a small portion of fencing needed to fully enclose the back field).  Unrestricted acreage is ideal for horses, livestock, or hobby farming.  Conveniently located minutes from Old Town Winchester, shopping, restaurants, and farmers' markets.   A rare opportunity for historic farmhouse living, equestrian property, and peaceful country lifestyle near town.  All sizes are approximate. See documents for a list of home improvements - home has been well-maintained and updated.
#VAFV2040656

WINCHESTER

171 LAUREL GROVE ROAD

3 Beds

3 Baths

3,052 Sq.Ft.

$725,000

MLS#: VAFV2040656

Have you been looking for the perfect sophisticated and elegant historic home?  Do you want everything; a gracious home, amazing space, acreage, a place for chickens, but also walkable and close to town?  It sounds impossible, but you've found it!  Welcome to historic Maplewood, circa 1872, know colloquially as The Tower.  With no HOA and business B-1 zoning, this property presents endless possibilities, allowing dozens of potential uses!  With stunning Italianate architecture and over an acre of land, this property is one in a million.   This landmark home located in the heart of lovely downtown Middletown is a piece of history with all the modern conveniences.  Rich with history, this amazing property was once the home and studio of John Chumley, a famous local artist.  (The current owners have tons of photos and information about the history of the home that they'd love to share with you!)  Too many amazing features to list; gorgeous high ceilings, original hardwood floors, wrap around built ins, huge windows, original millwork throughout, a generous kitchen and huge walk in pantry, fabulous mudroom, several outbuildings for storage and work space, an amazing chicken coop; the list goes on and on!  Featuring four large bedrooms and two and half bathrooms, this home is spacious, beautiful, and elegant.  The panoramic mountain views will take your breath away, especially from the tower studio room.  And the home sits on a fantastic level lot behind public memorial land!  All of this, located right in the center of town, so shopping and restaurants are just steps away.  Middletown is an ideal location for commuters, with Rt 37, I-66 and I-81 within just a few minutes drive, not to mention all the natural beauty, activities, and amenities of the Shenandoah Valley.  This is the one!!!
#VAFV2038812

MIDDLETOWN

2239 SIXTH STREET

4 Beds

2 Baths

2,944 Sq.Ft.

$649,900

MLS#: VAFV2038812

Unique opportunity to own a piece of history! This former schoolhouse has been converted into a multifamily property featuring two spacious 2-bedroom, 1-bath apartments. Each unit offers plenty of potential for updates and customization. Property is being sold as-is — no appliances or air conditioning, baseboard heat throughout. Situated on a generous 5.7-acre subdividable lot with room to expand - the possibilities are endless.  Enjoy the rural setting where horses and chickens are welcome. Bring your vision and transform this one-of-a-kind property into your next investment or country retreat!
#VAFV2037948

STEPHENSON

751 - 761 OLD CHARLES TOWN ROAD

4 Beds

2 Baths

1,668 Sq.Ft.

$515,000

MLS#: VAFV2037948

Unique opportunity to own a piece of history! This former schoolhouse has been converted into a multifamily property featuring two spacious 2-bedroom, 1-bath apartments. Each unit offers plenty of potential for updates and customization. Property is being sold as-is — no appliances or air conditioning, baseboard heat throughout. Situated on a generous 5.7-acre subdividable lot with room to expand - the possibilities are endless.  Enjoy the rural setting where horses and chickens are welcome. Bring your vision and transform this one-of-a-kind property into your next investment or country retreat!
#VAFV2039574

STEPHENSON

751 - 761 OLD CHARLES TOWN ROAD

4 Beds

None Baths

1,668 Sq.Ft.

$515,000

MLS#: VAFV2039574

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