Vintage homes for sale & real estate in 21769, MD

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COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
Historic elegance meets expansive acreage in this one-of-a-kind property at 1936 Old National Pike, Middletown, MD. Spanning nearly 4 acres, this brick home exudes old-world charm while offering a blank canvas for personalization and modern living. Discover a rare find: a historic, brick-constructed home built around the turn of the last century, situated on nearly 4 acres along Old National Pike in Middletown, MD. This property offers generous interior space, a durable metal roof, and beautifully mature grounds that present tremendous opportunity for landscaping, expansion, or outdoor living. Positioned on a historic artery — Maryland’s original National Road — this home

$465,000

4 beds2 baths2,824 sq ft

1936 Old National Pike, Middletown, MD 21769

3.87 acre lot • Built 1900 • Listed 5 days

(301) 662-0155

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
CHARMING RANCHER IN MIDDLETOWN, MD! Welcome home to this delightful 3-bedroom, 1.5-bath rancher in an excellent location. This well-maintained home features a cozy living room with fireplace, a kitchen, and a full basement with fireplace providing ample space for storage, hobbies, or future expansion. Hardwood floors extend through nearly the entire home! Enjoy the convenience of a paved driveway and an attached 2-car garage, perfect for parking and additional workspace. The spacious backyard offers plenty of room for outdoor entertaining, gardening, or simply relaxing. Located close to local schools, parks, and commuter routes, this home combines small-town charm with everyday practicality

$349,000

3 beds1.5 baths2,104 sq ft

10 Linden Blvd, Middletown, MD 21769

0.32 acre lot • 2 garage spots • Built 1955

(717) 597-9100

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
COMING SOON! Large 5 bedroom farmhouse with new, top-of-the-line gourmet kitchen, original stone house circa 1803, working greenhouses, bank barn, dairy barn with working offices, kitchen and bathrooms, machine shed, fields, pastures and more, all on 37+ acres of prime Middletown real estate!

$1,500,000

5 beds2 baths3,112 sq ft

2730 Marker Rd, Middletown, MD 21769

37.2 acre lot • 2 parking spots • Built 1900

(301) 694-8000

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
Charming Cape Cod on 3.56 Acres with Bonus Guest Home – Endless Potential Near the Appalachian Trail! Nestled on a picturesque 3.56-acre lot, this single-family Cape Cod offers the perfect blend of seclusion and convenience. Just minutes from town yet surrounded by nature, this property borders the scenic Potomac Appalachian Trail and Bear Spring cabins—ideal for outdoor enthusiasts seeking tranquility and adventure right at home. The main home features classic Cape Cod charm and awaits your personal touch to bring it back to life. Also included in the sale is a second dwelling, 1248 Mountain Church Rd, offering 2 bedrooms, a living room, kitchen, and full bath—perfect for

$224,900

2 beds1 bath900 sq ft

1246 Mountain Church Rd, Middletown, MD 21769

Bonus guest home • 3.56 acres • Peaceful rural feel

(443) 627-2900

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
Beautifully renovated oversized farmhouse in the heart of Middletown Valley. Blending timeless character with modern updates, this 3-bedroom, 2-full bath home is move-in ready and full of charm. Step inside to find spacious living areas filled with natural light, a thoughtfully updated kitchen with quality finishes, and two full bathrooms that have been tastefully remodeled. Original farmhouse details are complemented by contemporary upgrades, creating the perfect balance of old and new. Enjoy the peaceful setting from the covered porch or entertain in the generous yard surrounded by scenic views as well as the 2 story mancave with workshop below and a living space above that can be updated

$459,000

3 beds2 baths1,752 sq ft

8109 Old Hagerstown Rd, Middletown, MD 21769

Renovated farmhouse • Covered porch • Generous yard

(410) 705-6296

Property at 417 W Main St, Middletown, MD 21769, 3 beds, 1 bath

$299,990

3 beds1 bath1,392 sq ft

417 W Main St, Middletown, MD 21769

(301) 591-3920

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ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
Welcome to 6234 Old National Pike — a well-maintained late-1800s farmhouse situated on 2 scenic acres with peaceful mountain views. This charming home offers a blend of original character and select modern updates, creating a comfortable and inviting living environment. Step inside to a bright and inviting layout featuring refinished hardwood floors, fresh paint, and generous natural light throughout. The spacious living and dining areas connect to an updated kitchen with ample cabinet storage and room for everyday dining. A convenient mudroom off the side entry includes a generator hookup next to the electrical panel, offering practical preparedness. The main level includes a full ba

$285,000

3 beds2 baths1,222 sq ft

6234 Old National Pike, Boonsboro, MD 21713

2 acre lot • Built 1889 • Listed 3 days

(443) 901-2200

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
Inside pics coming soon! Exceptional Investment Opportunity in the Heart of Boonsboro – Two Homes on One Property! Discover this rare and versatile investment opportunity offering two separate homes on a spacious lot in charming downtown Boonsboro. Perfect for owner-occupants, multi-generational living, or rental income, this property combines historic character with thoughtful updates and unbeatable convenience. Main Home – Charming Stone Cape Cod The primary residence is a beautifully crafted stone Cape Cod showcasing timeless character and original hardwood floors throughout. Step into the welcoming foyer and to your left find a spacious family room featuring a wood-burning f

$350,000

3 beds1.5 baths2,339 sq ft

136 Lakin Ave, Boonsboro, MD 21713

Breakfast nook • Attached garage • 0.23 acre lot

(301) 882-7567

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
Enjoy scenic views, historic charm, and major recent upgrades at this beautifully maintained home in the desirable Middletown School District—with No city taxes and No HOA. Set on a raised lot with a welcoming wraparound porch. Inside, the home features original hardwood floors, classic trim, and spacious rooms filled with natural light. Laundry is on the upstairs bedroom level in the hall bathroom. Several key improvements provide peace of mind, including a new HVAC system (2025), new roof with 50-year transferable warranty (2024), new water heater (2023), and updated plumbing (2024). Right on top of Braddock mountain in Braddock Heights! Convenient to commuter routes, Historic Downt

$550,000

5 beds3 baths2,500 sq ft

6933-A Potomac Ave, Braddock Heights, MD 21703

0.25 acre lot • 2 garage spots • Built 1900

(301) 644-1086

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
Tastefully renovated farmhouse with a fabulous location! This 3 bed/2 full bath home offers a first floor laundry space, LVP flooring, renovated baths with high end finishes, and a spacious kitchen with quartz countertops/gas cooking/SS appliances/white shaker cabinets/tiled backsplash. Off the kitchen you'll find a nicely sized family room with vaulted ceilings and as a bonus the attic is finished for an additional bonus space! Outside there is off street parking, a long lasting metal roof and a large backyard for relaxing in. The home also features a new furnace & AC and a full basement for storage! * * Note home is larger then tax records * *

$435,000

3 beds2 baths1,470 sq ft

4810 Old Swimming Pool Rd, Frederick, MD 21703

Metal roof • Finished attic • Off street parking

(410) 705-6296

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
Welcome to Fielderia Manor, a stately 19th-century residence gracefully set on five pastoral acres along South Clifton Road in Frederick. Once part of the original Fielder Gaunt land patent of the 1770s, this remarkable home blends historic character with modern comfort. A tree-lined lane shaded by walnut trees opens to sweeping gardens filled with perennials—tulips, lilies, daffodils, hydrangeas, and more—that frame the stone-and-siding façade. Inside, over 4,500 sq. ft. of living space offers 10-foot ceilings, original wood floors, and a grand three-story staircase. Formal parlors, each with a fireplace, showcase intricate woodwork and tall windows, while the library&rs

$925,000

6 beds4.5 baths4,644 sq ft

6739-D S Clifton Rd, Frederick, MD 21703

5 acre lot • 2 garage spots • Built 1860

(301) 698-5005

ABOUT THIS HOME
Vintage Home for sale in 21769, MD:
Step into a beautifully renovated gem that seamlessly blends historic charm with modern convenience. This stunning home, built in 1875 and set to shine with major renovations in 2025, boasts 4 spacious bedrooms and 2 full bathrooms, perfect for both relaxation and entertaining. The inviting interior features plush carpeting and elegant laminate flooring. Enjoy cozy evenings on the patio, or utilize the additional shed for extra storage. The main floor laundry adds to the convenience of daily living. With a manageable lot size of 0.11 acres and driveway parking, this home offers both charm and practicality. Don’t miss the opportunity to own a piece of history, enhanced for modern livin

$389,900

4 beds2 baths1,638 sq ft

3830 Jefferson Pike, Jefferson, MD 21755

4,748 sq ft lot • Built 1875 • Listed 15 days

(877) 366-2213

Property at 202 E Main St, Burkittsville, MD 21718, 3 beds, 1 bath

$324,900

3 beds1 bath1,875 sq ft

202 E Main St, Burkittsville, MD 21718

(301) 745-4400

Property at 26 Young Ave, Boonsboro, MD 21713, 3 beds, 1 bath

$350,000

3 beds1 bath1,018 sq ft

26 Young Ave, Boonsboro, MD 21713

(301) 882-8710

Property at 106 E Main St, Burkittsville, MD 21718, 3 beds, 2 baths

$420,000

3 beds2 baths1,597 sq ft

106 E Main St, Burkittsville, MD 21718

(443) 542-2251

Property at 14 Saint Paul St, Boonsboro, MD 21713, 4 beds, 1 bath

$299,999

4 beds1 bath1,668 sq ft

14 Saint Paul St, Boonsboro, MD 21713

(240) 913-9339

Property at 3412 Jefferson Pike, Jefferson, MD 21755, 3 beds, 1 bath

$390,000

3 beds1 bath1,282 sq ft

3412 Jefferson Pike, Jefferson, MD 21755

(443) 353-5281

Property at 3419 Jefferson Pike, Jefferson, MD 21755, 4 beds, 3 baths

$1,295,000

4 beds3 baths3,362 sq ft

3419 Jefferson Pike, Jefferson, MD 21755

(240) 367-9600

Property at 40 N Main St, Boonsboro, MD 21713, 3 beds, 2 baths

$299,000

3 beds2 baths1,968 sq ft

40 N Main St, Boonsboro, MD 21713

(301) 745-4450

Property at 28 Potomac St, Boonsboro, MD 21713, 3 beds, 1.5 baths

$250,000

3 beds1.5 baths1,242 sq ft

28 Potomac St, Boonsboro, MD 21713

Property at 126 Lakin Ave, Boonsboro, MD 21713, 2 beds, 1 bath

$369,900

2 beds1 bath1,200 sq ft

126 Lakin Ave, Boonsboro, MD 21713

(301) 662-0155

Property at 1 W Main St, Burkittsville, MD 21718, 5 beds, 2 baths

$719,000

5 beds2 baths4,432 sq ft

1 W Main St, Burkittsville, MD 21718

(301) 644-1086

Property at 421 Main St, Myersville, MD 21773, 4 beds, 3 baths

$499,000

4 beds3 baths2,208 sq ft

421 Main St, Myersville, MD 21773

(301) 271-3487

Property at 123 Potomac St, Boonsboro, MD 21713, 3 beds, 3 baths

$395,000

3 beds3 baths2,192 sq ft

123 Potomac St, Boonsboro, MD 21713

(301) 695-3020

Property at 7 Main St W, Burkittsville, MD 21718, 3 beds, 2.5 baths

$635,000

3 beds2.5 baths2,519 sq ft

7 Main St W, Burkittsville, MD 21718

(301) 662-9222

Property at Lot 2 Wolfsville Rd, Myersville, MD 21773

$252,000

— beds— baths— sq ft

Lot 2 Wolfsville Rd, Myersville, MD 21773

(301) 371-4415

Vintage Homes for Sale in 21769

There are currently 6 vintage homes for sale in 21769 at a median listing price of $640K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21769 stay on the market for 40 days and receive 1 offers. This map is refreshed with the newest listings in 21769 every 15 minutes.

In the past month, 14 homes have been sold in 21769. In addition to houses in 21769, there were also 0 condos, 3 townhouses, and 0 multi-family units for sale in 21769 last month. Find your dream home in 21769 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 21769 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21769. If you're looking to sell your home in the 21769 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21769 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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