CHARIS REALTY GROUP
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
106
# of Listings
3
Avg # of Bedrooms
$335
Avg. $ / Sq.Ft.
$553,977
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

106 Properties Found. Page 5 of 8.

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

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.

$287,000

MLS#: PADA2050576

Great location to schools, shopping and major highways. With a little TLC, you could bring this home back to its glory days. This home boast a 2 car garage, an awesome large, flat back yard. Plenty of room to spread out in the beautiful family room with stone fireplace in the lower level. Don't wait, this home wont last. Welcome home!
#PADA2051824

MIDDLETOWN

1770 OBERLIN ROAD

4 Beds

2 Baths

1,100 Sq.Ft.

$285,000

MLS#: PADA2051824

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

New on site 1 day ago
Located on a large, fenced .47 acre lot in a quiet neighborhood this cute 2 or 3 bedroom rancher is the home you've been waiting for. On the main level the home features a large living room, a modern kitchen, two bedrooms plus a dining room or 3rd bedroom. The recently remodeled lower level offers a big family room, an office, a craft/hobby room. a powder room and a utility room. The home has oil hot air heat with central air conditioning , public sewer, well water and a radon mitigation system. Outside the home has off street parking for at least 4 vehicles. The big rear yard is perfect for your pets, is fenced with PVC fencing, and has a large shed and even a chicken coop. Some of the rooms have been virtually staged to enhance the viewing and show possible furniture placement. The seller is offering a one year home warranty with an acceptable offer.
#PADA2052090

MIDDLETOWN

2588 SPRING GARDEN DRIVE

2 Beds

1 Baths

1,107 Sq.Ft.

$250,000

MLS#: PADA2052090

376 Plane Street is just what you have been looking for. Completely remodeled as of this year, it is modern and move-in ready. As soon as you walk in the door you are greeted with an open living and dining area. The kitchen has been completely gutted, redone, and features granite counters, lots of cabinets and stainless steel appliances. The bathroom is conveniently located on the first floor, along with one of the bedrooms. During the remodel, the staircase was moved completely out of the way and is now located in the back of the home and leading upstairs to the other two bedrooms. All bedrooms have new carpet and have plenty of room. During the renovations, the items replaced and redone were the water heater, AC system, kitchen, kitchen appliances, relocation of the staircase, wiring, and flooring throughout. The 12x12 sunroom leading outside to the backyard has windows the whole way around - merging the indoor and outdoor space. At a competitive price - this one will go fast!
#PADA2050024

MIDDLETOWN

376 PLANE STREET

3 Beds

1 Baths

1,206 Sq.Ft.

$249,900

MLS#: PADA2050024

Welcome to this Wonderful Woodridge Townhome. The open floor plan creates a seamless flow between the living, dining, and kitchen areas. The kitchen is equipped with Granite Countertops and Stainless appliances and has an inviting Breakfast Bar that overlooks the Dining Area. The living room offers a comfortable setting for relaxation and entertaining. The primary bedroom offers ample space and includes a private en-suite bathroom. Both bathrooms are tastefully appointed with modern fixtures and finishes. Luxury Vinyl Plank throughout. The property's location provides convenient access to essential amenities and services in the surrounding area including major highways and Harrisburg International Airport.
#PADA2051414

MIDDLETOWN

912 WOODRIDGE DRIVE

2 Beds

2 Baths

1,310 Sq.Ft.

$244,900

MLS#: PADA2051414

An exceptional opportunity awaits with this versatile property perfectly suited for a wide range of R2 zoning uses. Currently the impeccably renovated headquarters of 717 Mortgage Group, this space reflects top-tier craftsmanship and attention to detail at every turn. Whether you envision a prime location for your business, a smart and appealing investment, or a seamless conversion to a single-family residence, this property offers unmatched flexibility. The thoughtfully designed layout easily supports multiple uses, and the finished media room in the basement adds a rare and valuable bonus. With ample off-street parking and a convenient in-town location, this property truly checks all the boxes.
#PADA2051902

MIDDLETOWN

120 W WATER STREET

None Beds

None Baths

N/A

$239,717

MLS#: PADA2051902

New on site 3 days ago
An exceptional opportunity awaits with this versatile property perfectly suited for a wide range of R2 zoning uses. Currently the impeccably renovated headquarters of 717 Mortgage Group, this space reflects top-tier craftsmanship and attention to detail at every turn. Whether you envision a prime location for your business, a smart and appealing investment, or a seamless conversion to a SINGLE FAMILY RESIDENCE, this property offers unmatched flexibility. The thoughtfully designed layout easily supports multiple uses, and the finished media room in the basement adds a rare and valuable bonus. With ample off-street parking and a convenient in-town location, this property truly checks all the boxes.
#PADA2052114

MIDDLETOWN

120 W WATER STREET

3 Beds

1 Baths

N/A

$239,717

MLS#: PADA2052114

Welcome to 16 Nissley Drive in Middletown. This home offers a new roof (2025), newer HVAC, and newer water heater, and is ready for a buyer to bring their personal touches. Enjoy a private backyard with a sunroom and covered back porch, perfect for relaxing or entertaining. A cozy front porch adds charm and a welcoming touch. An excellent opportunity to make this space truly your own.
#PADA2051982

MIDDLETOWN

16 NISSLEY DRIVE

2 Beds

2 Baths

1,300 Sq.Ft.

$225,000

MLS#: PADA2051982

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

This is an auction property! The auction will take place live at the property on Saturday, December 13th, @ 2:00pm. The price listed is not in any way the sale price and being an auction the property may sell for less or may sell for more on auction day. Home is located in the sought after Shope Gardens subdivision in Lower Swatara Township. Built in 1961, this house has a carport, 16X10 shed, gas forced air heat, central air, 100 amp electric service, public water, public sewer and domestic gas hot water heater. Lower level has 4 rooms, laundry and the utility room. Anyone interested in this opportunity is strongly encouraged to come to one of the open house times and make your plans. Open house dates are: Sunday, November 30th from 1:00-3:00pm, Sunday, December 7th from 1:00-3:00pm. Buyer pays 2% state transfer tax at settlement.
#PADA2051644

MIDDLETOWN

16 THEODORE AVENUE

3 Beds

1 Baths

1,786 Sq.Ft.

$188,900

MLS#: PADA2051644

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