One of the most popular communities provided by {{page_data.agentName}}

MIDDLETOWN

One of the most popular communities provided by Charis Realty

MIDDLETOWN

About MIDDLETOWN

Middletown, MD Real Estate: Your Ultimate Guide

Welcome to Middletown, Maryland! Nestled in the heart of Frederick County, Middletown offers a charming blend of small-town atmosphere and modern amenities. If you’re searching for a place where community, convenience, and natural beauty meet, Middletown, MD real estate is the perfect choice.

Why Choose Middletown, MD?

Located just minutes west of Frederick, Middletown boasts picturesque landscapes, historic landmarks, and a warm, welcoming community. Here’s why so many homebuyers are looking for houses for sale in Middletown, MD:

  • Stunning Mountain Views: Surrounded by the scenic Catoctin Mountains and rolling farmland, this area provides breathtaking vistas year-round.
  • Top-Rated Schools: Middletown is renowned for its excellent public schools, including Middletown High School.
  • Charming Downtown: Explore locally-owned shops, cafes, and eateries along Main Street for a classic small-town experience.
  • Nearby Recreation: Enjoy outdoor activities at Middletown Park, South Mountain State Park, and local golf courses.
  • Easy Access: Quick commutes to Frederick, Hagerstown, and even Washington, DC make Middletown ideal for professionals and families alike.

Middletown, MD Housing Market Overview

The Middletown, MD real estate market features a wide variety of properties, from historic Victorian homes to modern new constructions. Whether you’re a first-time buyer, looking to upgrade, or seeking a peaceful place to retire, Middletown offers:

  • Single-family homes
  • Townhouses
  • New builds and developments
  • Spacious lots and acreage

Interested in recent listings? Check current homes for sale in Middletown, MD for up-to-date market trends and pricing.

Live in the Heart of Frederick County

Relocating to Middletown, MD means you’ll experience:

  • A strong sense of community and friendly neighbors
  • Highly walkable streets with beautiful historic architecture
  • Year-round events, including the popular Middletown Heritage Festival
  • An unbeatable blend of rural charm and convenient suburban living

Ready to Find Your Dream Home in Middletown?

From stately colonials to custom-built estates, Middletown, Maryland real estate delivers exceptional value and quality of life. If you’re considering a move, now is the perfect time to contact a trusted Middletown, MD real estate agent to start your search.

Start living the life you’ve always dreamed of in Middletown, Maryland—where homes are more than houses; they’re part of a vibrant, enduring community.

One of the most popular communities provided by Charis Realty
107
# of Listings
3
Avg # of Bedrooms
$336
Avg. $ / Sq.Ft.
$550,388
Med. List Price

Browse MIDDLETOWN Real Estate Listings

35 Properties Found. Page 2 of 3.

New on site 1 day ago
Welcome to 8317 Hollow Road, a charming 5-bedroom home set on 1.15 acres in beautiful Middletown!  With sweeping views from the large front porch and a peaceful setting, this property offers the perfect blend of comfort, space, and rural tranquility, all just minutes from all the conveniences of Frederick!
Inside, the main level features a bright and spacious living room, a dedicated dining room, and an open kitchen with direct access to the backyard, making it ideal for everyday living and entertaining. A rare main-level bedroom and newly renovated full bath provide flexibility for guests, multi-generational living, or a home office. The kitchen also includes a large walk-in pantry that offers outstanding storage.Upstairs, you’ll find four additional bedrooms and a second full bathroom, giving everyone room to spread out. The lower level provides abundant storage space, as well as the laundry room.
Outside, enjoy 1.15 acres of open space; perfect for gardening, play, pets, or anything else you might need (there is no HOA!). Whether you’re relaxing on the front porch at sunset or hosting gatherings in the backyard, this home offers the perfect space! Spacious, inviting, and ideally located—8317 Hollow Road is ready to welcome you home.
#MDFR2074328

MIDDLETOWN

8317 HOLLOW ROAD

5 Beds

2 Baths

2,520 Sq.Ft.

$405,000

MLS#: MDFR2074328

Investor Alert! High Cash Flow + Strong ROI - Welcome to 219 South Union Street in Middletown - a fully improved mixed-use, multi-unit property offering impressive income and strong long-term upside! Featuring 1 commercial unit and 3 residential apartments, all separately metered and recently updated, this is a turn-key investment opportunity in a desirable downtown location. Income Breakdown:
Commercial Unit: $1,195/mo, 1BR/1BA Apartment: $1,070/mo (currently leased month to month - higher market rent potential), (2) 2BR/1BA Apartments: $1,495/mo each. - Total Monthly Gross Rent: $5,255
Annual Gross Income: $63,060 WOW!! CAP Rate of 11.56%, and Cash on Cash Return of 19.91%, 5-Year Investment Rate of Return (5% Appreciation) - 31.72%!! MASSIVE Depreciation Benefit!!
This property combines commercial stability with residential demand and future appreciation off the charts. Tenants pay their own electric, minimizing owner expenses. The building features high ceilings, exposed brick, ornate details, and private rear balconies for each apartment. Don’t miss this rare, high-yield investment opportunity in thriving downtown Middletown!
#PADA2049614

MIDDLETOWN

219 S UNION STREET

None Beds

None Baths

3,186 Sq.Ft.

$399,000

MLS#: PADA2049614

Investor Alert! High Cash Flow + Strong ROI - Welcome to 219 South Union Street in Middletown - a fully improved mixed-use, multi-unit property offering impressive income and strong long-term upside! Featuring 1 commercial unit and 3 residential apartments, all separately metered and recently updated, this is a turn-key investment opportunity in a desirable downtown location. Income Breakdown:
Commercial Unit: $1,195/mo, 1BR/1BA Apartment: $1,070/mo (currently leased month to month - higher market rent potential), (2) 2BR/1BA Apartments: $1,495/mo each. - Total Monthly Gross Rent: $5,255
Annual Gross Income: $63,060 WOW!! CAP Rate of 11.56%, and Cash on Cash Return of 19.91%, 5-Year Investment Rate of Return (5% Appreciation) - 31.72%!! MASSIVE Depreciation Benefit!!
This property combines commercial stability with residential demand and future appreciation off the charts. Tenants pay their own electric, minimizing owner expenses. The building features high ceilings, exposed brick, ornate details, and private rear balconies for each apartment. Don’t miss this rare, high-yield investment opportunity in thriving downtown Middletown!
#PADA2048820

MIDDLETOWN

219 S UNION STREET

5 Beds

None Baths

4,086 Sq.Ft.

$399,000

MLS#: PADA2048820

Attention developers... this 8 acres is currently being subdivided into 3 buildable lots. All 3 lots currently have passing perc tests. 1.19 acres, which you can see in the first photo of the cornfield. The other 2 lots are tucked in the woods with a private setting and are 3.29 acres, and 3.63 acres. All dry utilities are available out in the street. Another option for someone looking to build their dream home is to keep the last 2 larger lots (almost 7 acres combined) to build on, then sell the 1.19 acre separately. The remaining acreage kept to build on is right off the private road coming from Oberlin Rd., (see 2nd photo). Beautiful country setting, but close to shopping and restaurants.
#PADA2046770

MIDDLETOWN

675 OBERLIN ROAD

None Beds

None Baths

8.0 acres

$395,000

MLS#: PADA2046770

Calling all savvy investors! Check out this fabulous Duplex in Middletown’s hot spot: two side-by-side Townhomes packed with potential, 2 exceptional Traditional Townhomes offering a rare blend of size, location, and income potential. Each unit features 4 bedrooms, 1 bath, and a generous 2,468 sq ft of living space, and additional lower level 840 sq ft space.  Located in a highly desirable area, unit 121 is currently being rented for $1,500/month plus utilities, while unit 123 is rented at $1,600/month plus utilities. Recent updates include new carpet, upgraded water feed pipes, and a new water heater.  The property offers electric baseboard heating, rear utility closets, 2 side porches, front porch, and a fenced backyard. With a 2025 appraisal of $439,000 and sold As-Is, this is a top-tier income-producing investment property for any portfolio. Don’t miss this opportunity in a prime location!
#PADA2045062

MIDDLETOWN

121-123 KEYSTONE AVENUE

None Beds

None Baths

2,968 Sq.Ft.

$379,900

MLS#: PADA2045062

** $5,000 Builder Incentive offered on this home! Call for details. **
READY NOW ! This Pheasant model is a 3 BD, 2.5 BA, 1,895 sq. foot, end unit townhome. With its nine foot ceilings and open foyer, well-lit, spacious and open first floor, this home exudes elegance. Included in this kitchen is an island, granite countertops, stainless steel appliances, recessed lighting, an adjacent pantry and many more features. You will feel right at home in the owner’s suite with its large spaces and lots of natural light. The owner’s bath and walk-in closet are exceptionally spacious. Also on the second floor are a loft, bedrooms two and three, a family bath and the laundry room, which is just steps from all bedrooms and bathrooms. This home features a full lower level, a 10'x12' concrete patio, and a 2 car garage. A side porch affords additional outdoor living space. Interior selectins may still be available.
- All taxes are estimated as this is new construction and has not been assessed.
#PADA2046564

MIDDLETOWN

115 MOGNOLIA DRIVE

3 Beds

2 Baths

1,895 Sq.Ft.

$375,814

MLS#: PADA2046564

Middletown Ice & Coal building located in Middletown borough across from police station next to M&H Rail yard with 8,400 square feet of garage, storage and office space that is zoned M-1 Manufacturing. Two parcels with a total of .484 acres, accessible from both Race Street and Daisy Avenue. One story masonry building with mezzanine that consists of 862 sq. ft. office, 3,839 sq. ft.  storage area and 3,702 sq.ft. garage with 16' ceilings. Loading dock, weighing station, yard with bins for coal, sand or stone and an equipment shed for parking equipment. Located close to I-283, I-83 and the PA Turnpike. Off street parking for approximately 10 vehicles and more depending on how the yard is utilized.  Supper affordable!
#PADA2050910

MIDDLETOWN

15 S RACE STREET

None Beds

None Baths

N/A

$375,000

MLS#: PADA2050910

This recently updated three-bedroom, two-bath home is available in the charming town of Middletown, VA. Conveniently located near Main Street, you will quickly appreciate the vibrant community, which features locally owned restaurants, shops, and various community events. The home boasts modern finishes and is filled with an abundance of natural light. The semi-open concept kitchen and living area provide ample space for cooking, dining, and entertaining. Outside, you'll find a garage for additional storage and a spacious backyard perfect for outdoor gatherings.
#VAFV2036210

MIDDLETOWN

2432 LAUREL LANE

3 Beds

2 Baths

1,104 Sq.Ft.

$370,000

MLS#: VAFV2036210

Welcome home to Third St!!! The sellers are motivated and the home is simply waiting for you!!! This lovely and well maintained split foyer is on one acre of unrestricted property and also boasts quite a number of upgrades!  There is lots of space for entertaining, particularly outside with a fairly level landscape, and in the home there are ample rooms to work with.  This home has lots of opportunity for a number of uses; office spaces, guest rooms, hobby rooms... the possibliities are endless!  With so many upgrades there's little to do with finishing touches, making the home truly yours, as the seller have installed a new countertop and backsplash (2025), new floors in the kitchen, living room, lower level bedrooms (2025, and 2023 respectively), new wall paint throughout the home (2025), newly painted stairs (2025), new front porch and railings (2025), new dishwasher (2025), new fridge (2023), new stover (2021), new condenser unit (2024) and more! Make your appointment today!
#VAFV2037320

MIDDLETOWN

2425 THIRD STREET

4 Beds

2 Baths

1,688 Sq.Ft.

$365,000

MLS#: VAFV2037320

Dream Homesite, Discover your perfect escape on this wooded, well installed and septic approved and engineered and ready to build, Nestled high above Middletown Valley the lot has a cleared homesite. views privacy and tranquility  and minutes from town.
#MDFR2061288

MIDDLETOWN

8511 ROSEBUD COURT

None Beds

None Baths

8.2 acres

$339,000

MLS#: MDFR2061288

Beautiful three-level townhome in the Enfield Knolls community of charming Middletown, VA. The open floor plan is filled with natural light and features a modern kitchen with stainless steel appliances and a moveable island that conveys. Enjoy durable luxury vinyl plank flooring, a composite deck for outdoor relaxation, and the convenience of bedroom-level laundry. With 3 bedrooms, 2.5 baths, and a walk-out basement offering great storage space and access to the backyard, this home has it all. Ideally located near commuter routes to both I-66 and I-81, and with trash collection handled by the Town of Middletown, this is easy living in a great location.
#VAFV2037714

MIDDLETOWN

119 KENSINGTON CIRCLE

3 Beds

2 Baths

1,887 Sq.Ft.

$334,000

MLS#: VAFV2037714

UNDER CONSTRUCTION. This Bluebird model is a 3 BD, 2.5 BA, center unit townhome. You'll soon discover the value of the many included features that are packed into this home. The open first floor plan will make entertaining family and friends a pleasure. Nine foot first floor walls make this home feel even more spacious. You will love all the storage available in the walk-in pantry. Check out the size of these bedrooms! The owner's suite is sure to please with large spaces and lots of natural light. Bedrooms 2 and 3 have their own full bath. The laundry room is just steps from all bedrooms and bathrooms. This home also boasts a full, unfinished, lower level, 10x12 patio and a 2 car garage. Interior selections may still be available.
-This is new construction and has not yet been assessed so all taxes are estimated.
-Interior photos are from a similar home.
#PADA2046562

MIDDLETOWN

121 MAGNOLIA DRIVE

3 Beds

2 Baths

1,539 Sq.Ft.

$323,575

MLS#: PADA2046562

Move in before the holidays! This beautifully maintained, move-in ready 3-bedroom, 2.5-bath townhome in Woodland Hills offers a bright, modern layout with an open main level, stainless steel appliances, and second-floor laundry. Enjoy a walk-out basement with finishing potential, a private balcony, and an attached garage. 

Conveniently located near Rt. 283, shopping, dining, and Penn State Harrisburg. 

Schedule your showing today!
#PADA2048552

MIDDLETOWN

158 SAGE BOULEVARD

3 Beds

2 Baths

2,090 Sq.Ft.

$319,900

MLS#: PADA2048552

4 bedroom 2 1/2 bath entertainers delight in Middletown off Street Parking level yard for picnics brand new interior move in ready over 1900 ft.². Open floor plan with tile, shower and backsplash granite countertops, new cabinetry time to throw a party! just in time for the holidays! Royalton Boro you own the land not land lease seller says sell bring offers.
#PADA2050404

MIDDLETOWN

416 PENN STREET

4 Beds

2 Baths

1,968 Sq.Ft.

$304,900

MLS#: PADA2050404

This charming historical residence, originally built in the late 1800’s showcases a unique blend of traditional architectural style and modern craftsmanship. Located near the square in the heart of Middletown Borough, this home exudes warmth and character, inviting you to experience its spacious 3,860 square feet of living space with potential for multigenerational living. The exterior, crafted from classic brick, offers a timeless appeal, while the interior features the original hardwood flooring that flows seamlessly throughout the first level. The thoughtful renovations have preserved the home's original charm while enhancing its functionality, making it a perfect canvas for your personal touch. With a generous lot size of 0.23 acres, the property provides ample outdoor space for relaxation, recreation or gardening. The unfinished basement, with interior access, presents an opportunity for customization. On-street parking is available with the potential for off-street options, accommodating your lifestyle needs. This unique home boasts 2 kitchens (one on each side), 8 bedrooms (4 on each side) and 4 full bathrooms (2 on each side) on one parcel.  The kitchens were updated in the 1990’s and 2008.  The 2nd floor bathroom (West side) was renovated in 2022.  The 3rd floor bathroom (East side) was renovated in 2024. The home's design emphasizes comfort and livability, making it an ideal setting for gatherings or quiet evenings at home. This residence is not just a house; it's a place where memories are made, and a sense of belonging is fostered. Experience the perfect blend of historic charm and modern convenience in this delightful Middletown Borough gem.  While zoned residential, the house is in the C-2 Commercial District, which can allow the uses listed in Article X (Associated Documents). Two families with children purchased this home together in the 1980's.  In 2004, when the children had grown, one of the families sold their half to the remaining sellers.  This home is being sold ‘as is’.
#PADA2051514

MIDDLETOWN

33 E MAIN STREET

8 Beds

4 Baths

4,988 Sq.Ft.

$300,000

MLS#: PADA2051514

1 2 3

properties found. properties found. Page of .

 - property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here