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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
723
# of Listings
3
Avg # of Bedrooms
$385
Avg. $ / Sq.Ft.
$723,083
Med. List Price

Browse HISTORIC HOMES (CENTRAL MD) Real Estate Listings

13 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

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

NEW SEPTIC JUST INSTALLED. This is a unique opportunity to purchase a piece of history.  The Glass Mill (Glass/Rinker/Cooper Mill) is available.  The Mill was constructed during the years 1812-1815.  At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends.  The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in place.  The next two levels are wide open with wood floors and open beams.  There are also stairs to attic space on the very upper level. The attached "miller's house" was added several decades later.  Still quite livable with original wood floors, formal living and dining rooms, and bedroom(s), bath, upstairs.  The interesting features remain.  The Mill office is off the living room, where the original wood burning fireplace remains. The house has a covered front porch, and rear upper and lower covered porches.  The grounds are quite nice with an array of plantings and a path/walking bridge over Opequon Creek.   This property is at the corner of Cedar Creek Grade and Miller Road.  There is no For Sale sign posted. Inquire about information relating to Deed of Gift Easement with Historical.  The Seller is in the process of having the Septic System replaced.
#VAFV2033452

WINCHESTER

2431 CEDAR CREEK GRADE

3 Beds

1 Baths

1,036 Sq.Ft.

$370,000

MLS#: VAFV2033452

Motivated seller!  PRICE IMPROVEMENT and closing cost assistance of up to $5000!!! Seller is moving out of state.  Welcome home to timeless charm with this beautiful 3-bedroom, 2–full-bath home, featuring stunning original woodwork that has been exceptionally well preserved. From the moment you enter, you’ll appreciate the character and craftsmanship that make this home truly special.  While leaving the character of the home, it has been well cared for.  New roof within five years, windows were replaced and updated 10 years ago and new electrical last year.  

The spacious layout offers large closets throughout and comfortable living spaces filled with natural light. Situated on over half an acre, the property provides plenty of room to enjoy outdoor living—without the restrictions of an HOA.

Conveniently located in the heart of Winchester, this home offers a central location close to shopping, dining, schools, and other everyday amenities, with easy access to anywhere you need to go.

Two large sheds provide excellent storage or workspace options, making this property as practical as it is charming. A rare opportunity to own a classic home in fantastic condition with space, freedom, and an unbeatable location.
#VAFV2038700

WINCHESTER

139 BRYARLY ROAD

3 Beds

2 Baths

1,585 Sq.Ft.

$365,000

MLS#: VAFV2038700

4 -bedroom, 1.5-bath single-story home with 1,439 sq ft on a 0.14-acre lot. Features living room, second 
living space, dining area, kitchen, and two storage shops. Roof functional; siding and gutters may need 
updates. Appliances included: fridge, freezer, stove. Window AC units and wood stove. Public water & 
sewer, electricity by REC. Conveniently located near Frederick County schools.
#VAFV2038900

MIDDLETOWN

2339 THIRD STREET

4 Beds

1 Baths

1,439 Sq.Ft.

$219,900

MLS#: VAFV2038900

2‑story, 2‑bed farmhouse on 4  acres. Property includes detached 2‑car garage, existing well and interior shower (no full bathroom). No septic system on site. Excellent opportunity for renovation or redevelopment in a peaceful rural setting. Sold AS‑IS; buyer responsible for verification of utilities, permits and septic needs.
#VAFV2040368

WINCHESTER

557 FROG HOLLOW ROAD

2 Beds

None Baths

784 Sq.Ft.

$149,999

MLS#: VAFV2040368

$7,000 / Month – Flexible Lease Terms

Winchester, VA

Take advantage of a turn-key auto dealership location positioned directly off Interstate 81 with exceptional traffic exposure. This property is ideal for a car dealership, auto sales & service operation. 

🔑 Property Highlights
 • Total Land: Approx. 0.92 acres
 • Interior Space: 3,500 sq ft
 • B2 Zoning: Auto-Friendly / Dealership Ready!

🚘 Vehicle Capacity
 • Main Lot: Fits approx. 30 vehicles
 • Additional Lot (Included) fits approx. 50 vehicles
 • Total Capacity:  80 vehicles

🔧 Service & Repair Capabilities
 • 3 Auto Repair Garage Bays
 • 1 Bay Equipped with Vehicle Lift
 • Perfect for in-house reconditioning, inspections, and service revenue.

📍 Prime Location Advantage
 • Directly off I-81 – excellent visibility
 • Across from Sheetz gas station – constant traffic flow
 • High daily vehicle count = maximum exposure
 • Established automotive corridor

💼 Ideal For
 • Car Dealership
 • Buy-Here Pay-Here operation
 • Auto sales + service combo
 • Fleet sales & maintenance
 • Expansion location for existing dealers

💰 Lease Terms
 • Rent: $7,000 per month
 • Lease: Flexible terms available
 • Additional Lot Included in Rent

📞 Serious inquiries only.
This is a rare opportunity to secure a fully functional dealership property in a high-traffic location.

Business Transfer: A goodwill payment will be required for the transfer of the existing dealership operations. Details and amount to be discussed.
#VAFV2038672

STEPHENS CITY

790 FAIRFAX STREET

None Beds

None Baths

3,500 Sq.Ft.

$6,000

MLS#: VAFV2038672

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