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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
105
# of Listings
3
Avg # of Bedrooms
$314
Avg. $ / Sq.Ft.
$572,106
Med. List Price

Browse MIDDLETOWN Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

105 Properties Found. Page 5 of 7.

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.

$337,000

MLS#: VAFV2037714

Welcome to this well-built brick Cape Cod, offering 1,500 square feet of thoughtfully designed living space on two deeded lots totaling 1.32 acres. This unique property combines classic craftsmanship with modern updates and a host of desirable amenities, making it a rare find. Step inside to discover a spacious remodeled kitchen, perfect for everyday cooking or entertaining. The warm hardwood floors flow through the home, adding timeless character. The first floor features a generously sized primary suite with an oversized bathroom, complete with a jetted soaking tub and separate walk-in shower. A second bedroom on the main level has been converted into a convenient laundry room, while two additional bedrooms upstairs provide plenty of flexible space for family, guests, or a home office. A highlight of this property is the attached breezeway and oversized garage, with both front and rear access—ideal for car enthusiasts, hobbyists, or anyone who values practicality and storage. Outdoors, the opportunities are endless. A 14’ x 32’ barn-style shed currently serves as a fully equipped woodshop with electric and heat but could easily transform into the ultimate man cave, hobby studio, or entertainment space. The expansive lot offers ample room for gardening, a fire pit, or simply enjoying the natural surroundings. The wrap-around driveway adds convenience, while the open acreage creates a haven for wildlife—you’ll often spot deer and turkeys roaming the grounds. Perfectly situated, this property provides the tranquility of country living with the convenience of easy access to major highways and the Middletown School Campus. Whether you’re seeking a place to relax, entertain, or create, this home delivers the space and versatility to match your lifestyle. Don’t miss your chance to own this one-of-a-kind property where charm, comfort, and possibility come together.
#PADA2048644

MIDDLETOWN

420 OBERLIN ROAD

3 Beds

1 Baths

1,500 Sq.Ft.

$334,900

MLS#: PADA2048644

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

Welcome to this delightful 3-bedroom, 1-bath single-family home nestled on Main St. in the heart of historic Middletown. Full of character and timeless appeal, this vintage gem is brimming with potential. Situated on a generous lot, the home boasts a spacious backyard—perfect for outdoor entertaining, gardening, or future expansion. Inside, you'll find original details that speak to the home's heritage, creating a warm and inviting atmosphere that’s ready to be reimagined. Whether you're looking to bring new life to a classic property or create your dream home in a sought-after location, this residence offers the perfect canvas. Attic is fully floored for extra storage, basement is unfinished & is another great storage space. With its unbeatable location in a charming community close to schools, shops, and parks, this is an opportunity you don’t want to miss.
#MDFR2069270

MIDDLETOWN

417 W MAIN STREET

3 Beds

1 Baths

2,088 Sq.Ft.

$299,990

MLS#: MDFR2069270

NEW IMPROVED PRICE!! If you're looking for a charming townhome nestled in the desirable Woodbridge community, this may be the one for you! This nicely, maintained end unit townhome features three bedrooms, two and a half baths, 1880 finished sq. ft., two car garage and more! Step into a welcoming entry and be met with an inviting layout of comfort, traditional style and convenience. The living room is located off the entry and is the perfect place to relax or entertain. The well appointed kitchen offers ample cabinetry, a large island with seating for four, modern stainless steel appliances, dining area and access to the back deck where you can enjoy your morning coffee and outdoors . Beautiful, luxury, vinyl plank flooring flows from the entry into the kitchen, dining and half bath areas. A convenient laundry room and half bath complete the main level. Upstairs you'll find a generously sized primary bedroom with walk in closet, en-suite bathroom complete with walk-in shower and double sink vanity. Two more bedrooms and a full hall bath with tub/shower combo offer extra retreat . The finished lower level, with access to the two car garage, adds more space and flexibility to your lifestyle needs. Whether you need an extra bedroom, office or game room, this space can accommodate. Enjoy the comfort, ease and time saved with low maintenance living with lawn and snow removal covered by HOA. Newer HVAC and hot water heater are added bonuses . Woodridge development is a prime location convenient to shopping, schools, dining , HIA and major commuter routes. Schedule your showing today and make this your new Home Sweet Home! *Professional photos to be uploaded on Oct. 23rd*
#PADA2050576

MIDDLETOWN

1236 OVERLOOK ROAD

3 Beds

2 Baths

1,880 Sq.Ft.

$299,000

MLS#: PADA2050576

Rural setting in cozy Sub Division. Situated five minutes from Elizabethtown and one and a half miles from Route 283. Thirty-five minutes from Penn Square in Lancaster City. Perfect for commuting to Harrisburg or Lancaster. Easy single floor living. Beautiful refinished hardwood floors. Fresh painted interior and trim. Mini Splits for heating and cooling. Full basement. New roof installed November of 2024. Move in ready. Current owner purchased expecting to change jobs. The situation changed so he renovated it to sell. Current owner has never occupied the home. Great home for first time homebuyers or for downsizing seniors. Sold "As Is." See Seller's Disclosure for Septic information.
#PADA2050694

MIDDLETOWN

158 GARDEN AVENUE

3 Beds

1 Baths

1,120 Sq.Ft.

$269,900

MLS#: PADA2050694

Welcome to 308 Aspen Street, Middletown!! Prepare to be impressed, this 4 bedroom cape style home offers coziness, convenience and efficiency!! Interior renovation makes this an attractive property for the buyer in search of value in the Middletown area!! Fenced back yard is ideal for pets and or children!! Location is ideal to interstates, turnpike and airport, all at an affordable price!! Make this your address today!! Hurry, priced to SELL, won't last LONG!!
#PADA2049428

MIDDLETOWN

308 ASPEN STREET

4 Beds

1 Baths

1,373 Sq.Ft.

$269,000

MLS#: PADA2049428

This is the one you’ve been waiting for. Fully renovated from top to bottom, this classic Middletown home blends modern updates with timeless charm. With a fresh exterior, updated systems, and stylish interior finishes, this home is move-in ready and offers incredible value in today’s market. Step inside to find a bright and spacious main living area with new flooring and recessed lighting, flowing directly into an open-concept kitchen featuring solid wood cabinets, ample counter space, and a convenient breakfast bar. The floor plan is flexible and functional, perfect for entertaining or everyday living. Upstairs, you’ll find comfortable bedrooms with generous closets, while the bathrooms have been fully updated with modern fixtures and finishes. The lower level includes a clean, usable basement ideal for storage, hobbies, or future finishing. Out back, enjoy a manageable yard with space to garden, grill, or relax. Whether you’re a first-time buyer looking for a turnkey property or someone relocating and wanting something refreshed and low-maintenance, this home checks all the boxes. This isn’t just a renovation. It’s a well-thought-out upgrade that’s ready for its next chapter. Schedule your private tour today!
#PADA2051144

MIDDLETOWN

16 JUNIATA STREET

3 Beds

1 Baths

1,512 Sq.Ft.

$250,000

MLS#: PADA2051144

Charming Cape Cod style home on a spacious corner lot with mature trees, a long driveway and plenty of yard space. offering potential for the right buyer. The main house features 3 bedrooms and 1.5 bathrooms, and a large upstairs den currently used as a bedroom. Enjoy a spacious living room, a separate dining area, and an eat-in kitchen. The finished basement includes a laundry area, a kitchenette with running water, an an additional room that can be used as a bedroom. The property also includes 2 unique detached structures: a large two-car garage with a loft and an additional rear storage/workshop area, and a detached ranch-style building with one bedroom and one bath, recently stripped and ready for renovation - perfect for additional family members or use as a rental property. Price includes new roof on 2 car garage and on ranch home (bid is including in listing documents). This property offers space, flexibility, and a great neighborhood setting. Home is value priced and in good condition.
#PADA2049388

MIDDLETOWN

105 OAK HILL DRIVE

4 Beds

None Baths

3,000 Sq.Ft.

$248,900

MLS#: PADA2049388

Charming Cape Cod style home on a spacious corner lot with mature trees, a long driveway and plenty of yard space. offering potential for the right buyer. The main house features 3 bedrooms and 1.5 bathrooms, and a large upstairs den currently used as a bedroom. Enjoy a spacious living room, a separate dining area, and an eat-in kitchen. The finished basement includes a laundry area, a kitchenette with running water, an an additional room that can be used as a bedroom. The property also includes 2 unique detached structures: a large two-car garage with a loft and an additional rear storage/workshop area, and a detached ranch-style building with one bedroom and one bath, recently stripped and ready for renovation - perfect for additional family members or use as a rental property. Price includes new roof on 2 car garage and on ranch home (bid is including in listing documents). This property offers space, flexibility, and a great neighborhood setting. Home is value priced and in good condition.
#PADA2049282

MIDDLETOWN

105 OAK HILL DRIVE

3 Beds

1 Baths

2,100 Sq.Ft.

$248,900

MLS#: PADA2049282

Welcome to 908 Vine Street in Middletown; the perfect place to call your first home! This charming property features beautiful, real, hardwood floors, a bright and inviting living space, and a layout designed for both comfort and functionality. The kitchen offers plenty of room to cook and gather, while the bedrooms provide cozy retreats. The third bedroom is ideal for a nursery, home office, or guest room, giving you the flexibility to make the space your own. Outside, you’ll find a lovely, flat backyard, perfect for relaxing, entertaining, or adding your personal touch. Nestled in a convenient Middletown location close to parks, shops, and schools, this home offers a wonderful opportunity for first-time buyers to build equity and create lasting memories. Don’t miss your chance to make 908 Vine Street your very own — schedule your showing today!
#PADA2050710

MIDDLETOWN

908 VINE STREET

3 Beds

1 Baths

1,944 Sq.Ft.

$235,000

MLS#: PADA2050710

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 guests, extended family, or potential rental income. Both homes need work, but the opportunity to create your dream property makes them well worth the investment. With over an acre of level, cleared land and additional wooded acreage for privacy, this is the perfect setting for future building or expansion. Whether you’re searching for a renovation project, multi-home living, or a serene weekend retreat, this property offers incredible potential in a truly special location. Highlights: 3.56 scenic acres bordering the Potomac Appalachian Trail Main Cape Cod home plus secondary 2-bedroom dwelling Over 1 acre of cleared, level land—ideal for building or recreation Peaceful, rural feel just minutes from town Excellent investment or fixer-upper opportunity Bring your vision and make this unique mountain property your own!
#MDFR2072636

MIDDLETOWN

1246 MOUNTAIN CHURCH ROAD

2 Beds

1 Baths

900 Sq.Ft.

$224,900

MLS#: MDFR2072636

Stylish, move-in ready, and full of fresh updates, this 3-bedroom, 1.5-bath Middletown townhome checks every box. Step inside to find bright, open spaces with new LVP flooring, plush carpet, and fresh paint throughout. Both bathrooms have been tastefully updated, and the basement adds extra room for work or play. Outside, enjoy a refreshed deck and storage shed for all your extras. New roof installed June 2025! Perfectly located near schools, shopping, and commuter routes, this home blends comfort and convenience, while having no HOA. Don’t wait, schedule your showing today!
#PADA2050868

MIDDLETOWN

1204 GEORGETOWN ROAD

3 Beds

1 Baths

1,631 Sq.Ft.

$210,000

MLS#: PADA2050868

New on site 1 day ago
Discover this well-maintained 3-bedroom home in the heart of Middletown Borough, Pennsylvania located on Oak Hill Drive, a peaceful and quiet location. Step inside to a open first floor where restored hardwood floors flow from the living room—complete with a cozy fireplace and windows that bring in natural light—into the formal dining room and updated kitchen. The kitchen features granite countertops, stainless steel appliances, and easy access to the sunroom/laundry area and enclosed back patio, perfect as a mudroom with rear entry. All major updates were completed in 2019, including a new roof, central air conditioning, furnace, windows, and a dry basement system. The two-car detached garage has electric service and offers ample storage, complemented by the full basement. Outside, enjoy a flat, fenced yard ideal for outdoor gatherings or play, with plenty of room for gardening or relaxation. Conveniently located near restaurants, shopping, and major routes, this move-in-ready home combines comforts with a quiet and sweet neighborhood.
#PADA2051190

MIDDLETOWN

348 OAK HILL DRIVE

3 Beds

1 Baths

1,260 Sq.Ft.

$209,900

MLS#: PADA2051190

Welcome to this charming 3-bedroom, 1-bath home in the heart of Middletown, ideally situated near the state capital and just minutes from the airport. Renovated within the last three years, this property combines modern updates and everyday comfort, offering peace of mind for years to come. The spacious layout provides plenty of room to relax and entertain, while the updated finishes make it truly move-in ready. Whether you're searching for your next home or a strong investment opportunity, this property checks all the boxes. With its convenient location and recent renovations it's an ideal choice for a primary residence or a rental with long-term potential. Don't miss the chance to own a well-maintained home in a prime location!
#PADA2049782

MIDDLETOWN

54 NISSLEY STREET

3 Beds

1 Baths

1,246 Sq.Ft.

$189,900

MLS#: PADA2049782

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