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 Group

MIDDLETOWN

About MIDDLETOWN

Discover Middletown, MD Real Estate 

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 Charis Realty Group 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 Group
255
# of Listings
3
Avg # of Bedrooms
$267
Avg. $ / Sq.Ft.
$654,193
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

42 Properties Found. Page 2 of 3.

UNDER CONSTRUCTION. *$15,000 builder incentive; thru 2/28/26* 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. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. You will love all the storage available in the walk-in pantry. The entire first floor has luxury vinyl plank flooring. 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 walk-out lower level, 10×12 composite deck, and a 2 car garage. - Interior photos are of a similar model. - All taxes are estimated since this is new construction and has not yet been assessed.
#PADA2051548

MIDDLETOWN

128 MAGNOLIA DRIVE

3 Beds

2 Baths

1,539 Sq.Ft.

$339,375

MLS#: PADA2051548

*$15,000 builder incentive; thru 2/28/26* 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. A self-cleaning electric range, granite counters and soft-close cabinet doors/drawers are featured in this kitchen. You will love all the storage available in the walk-in pantry. The entire first floor has luxury vinyl plank flooring. 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 walk-out lower level, 10×12 composite deck, and a 2 car garage. - Interior photos are of a similar model. - All taxes are estimated since this is new construction and has not yet been assessed.
#PADA2051576

MIDDLETOWN

130 MAGNOLIA DRIVE

3 Beds

2 Baths

1,539 Sq.Ft.

$339,375

MLS#: PADA2051576

This beautifully kept 3-bedroom, 2.5-bath townhome in Woodland Hills is move-in ready and waiting for you! Inside, you'll find an open layout filled with natural light on the main floor, complete with stainless steel appliances (high end refrigerator stays) and a convenient second-floor laundry area. Washer and Dryer already installed. Other great features include: walk-out basement with plenty of potential to finish for extra living space, deck overlooking private woods, attached 2 car garage with another 2 car driveway, no homes or neighbors directly behind you. Location is super convenient—close to Route 283, shopping, dining, Hershey, Harrisburg, and Penn State Harrisburg. You're also just a short 3 minute walk to the Middletown Swim Club. The current owner has barely lived here, so the home feels almost new. Economical gas heat to help keep utility bills low. Don't miss out—schedule your showing today!
#PADA2056216

MIDDLETOWN

158 SAGE BOULEVARD

3 Beds

2 Baths

1,524 Sq.Ft.

$327,700

MLS#: PADA2056216

OPEN HOUSE SUNDAY MARCH 1 1-3 pm Host Sue Kleinfelter Middletown Area Schools 4 bedroom 2 -1/2 bath Single Detached 1 Family Home. Come see this 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 Spring! Royalton Boro you own the land not land lease seller says sell bring offers.
#PADA2056298

MIDDLETOWN

416 PENN STREET

4 Beds

2 Baths

1,968 Sq.Ft.

$295,000

MLS#: PADA2056298

New on site today
Welcome to this well maintained two bedroom, one and a half bathroom townhome in Middletown offering comfortable living with thoughtful updates throughout. The eat-in kitchen features newer appliances, a gas range with hood, and a charming farmhouse sink, and flows into the attached dining area with direct access to the backyard, making indoor and outdoor entertaining a breeze. Step outside to enjoy the multilevel deck, fenced-in yard, and convenient storage shed. The half bath, which includes the laundry area, is conveniently located on the main level. Upstairs, you’ll find well maintained carpet and a full bathroom with abundant storage, a linen closet, and direct access to the primary bedroom. The primary bedroom offers generous closet space, while the second bedroom is filled with wonderful natural light and includes a ceiling fan and its own closet. The lower level adds even more flexibility with an office or den, two additional storage closets, and access to the one car attached garage. This well cared for home is truly move-in ready and a must see!
#PADA2056888

MIDDLETOWN

1606 GEORGETOWN ROAD

2 Beds

1 Baths

1,296 Sq.Ft.

$290,000

MLS#: PADA2056888

Step into this surprisingly spacious home that offers an ideal blend of comfort and convenience in a highly desirable location. The interior features well-proportioned rooms, centered around a generous living room that provides ample space for relaxation and gatherings. Culinary enthusiasts will appreciate the updated kitchen, which boasts abundant cabinetry and counter space. The formal dining room is brightened by a large bay window, making it perfect for hosting dinner parties or casual meals. Many updates significantly enhance the home's efficiency and appeal. These include thermal windows, which contribute to lower energy bills and improved comfort. A significant upgrade is the newer Bosch high-efficiency gas tankless water heater, which provides continuous hot water on demand and whole-home warmth, further reducing energy costs. For outdoor enjoyment, there is a charming, screened porch, ideal for entertaining guests or enjoying quiet evenings. The exterior also offers practical amenities such as a detached garage, a fenced yard providing privacy and safety, and plenty of green space for gardening, recreation, or pets. Furthermore, this home is ideally located within walking distance of the local library, various shopping options, and Penn State Harrisburg (PSU Middletown).
#PADA2051708

MIDDLETOWN

328 N SPRING STREET

4 Beds

1 Baths

2,764 Sq.Ft.

$219,000

MLS#: PADA2051708

New on site 1 day ago
Welcome to 258 E Water St in Middletown, a move in ready detached home located on the outskirts of town offering both convenience and comfort with easy access to major highways, local stores, and surrounding towns making commuting and daily errands simple while still enjoying a quieter setting. Inside you will find a truly unique kitchen featuring beautiful Italian tile backsplash that adds character and charm you will not see every day. The seller installed a propane fireplace that efficiently heats the home helping keep electric bills to a minimum while creating a warm and inviting atmosphere. Enjoy outdoor living on the welcoming front porch, entertain on the patio, or unwind on the private balcony off the main bedroom, the perfect spot for morning coffee or relaxing evenings. This well maintained detached home offers comfort, convenience, and character ready for its next owner to move right in and enjoy.
#PADA2056712

MIDDLETOWN

258 E WATER STREET

3 Beds

1 Baths

1,580 Sq.Ft.

$209,900

MLS#: PADA2056712

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.

$179,900

MLS#: PADA2049782

Build your dream home on this 2.04 acre lot! Located in the desirable Lower Dauphin School District. Penway Construction, Inc is the exclusive Builder. This prime location is approximately 6 miles from Hershey Medical Center. The lot offers loads of possibilities. Permitted zoning uses are attached. The taxes and assessed value are estimated. Schedule your showing today!
#PADA2052080

MIDDLETOWN

Lot 1 SCHOOLHOUSE RD

None Beds

None Baths

2.04 acres

$170,000

MLS#: PADA2052080

Build your dream home on this 1.9 acre lot! Located in desirable Lower Dauphin School District. Penway Construction, Inc is the exclusive Builder. This prime location is approximately 6 miles from Hershey Medical Center. The lot offers loads of possibilities. Permitted zoning uses are attached. The taxes and assessed value are estimated. Schedule your showing today!
#PADA2052084

MIDDLETOWN

Lot 3 SCHOOLHOUSE RD

None Beds

None Baths

1.9 acres

$165,000

MLS#: PADA2052084

Build your dream home on this 1.78 acre lot! Located in the desirable Lower Dauphin School District. Penway Construction, Inc is the exclusive Builder. This prime location is approximately 6 miles from Hershey Medical Center. The lot offers loads of possibilities. Permitted zoning uses are attached. The taxes and assessed value are estimated. Schedule your showing today!
#PADA2052082

MIDDLETOWN

Lot 2 SCHOOLHOUSE RD

None Beds

None Baths

1.79 acres

$160,000

MLS#: PADA2052082

CALLING INVESTORS / LANDLORDS _ONCE UPON A TIME... and the story for this property ownership begins 1980 when during purchase as double duples (239 and 241 Wilson Street), house fire occurred. Purchase continued and property was totally rehabbed: gutted, wiring replace 200 amp service, insulation added - - permits were obtained and property inspected as Borough Codes. 2003-2004 with subdivision map uploaded document. - lot dimension 15.47' X 75'. Semi-Detached 3-bedroom plus office -this is 3-story with 1 1/2 baths. Location downtown with easy access buses, trains and planes. As tenant occupied, need showings be scheduled ahead. Tenant pays $840 rent plus utilities - except $10/yr Frey Estate Trust. Tenant owns appliances (Washer-Dryer, Electri Range, Refrigerator). Great Opportunity to add to investment portfolio. Successful long term rental history -Property Manager & co-owner Walt Eby, licensed real estate broker and/or his wife.
#PADA2052106

MIDDLETOWN

239 WILSON STREET

3 Beds

1 Baths

1,582 Sq.Ft.

$159,000

MLS#: PADA2052106

UPDATE: Tenants have been moved out. Home is being cleaned out and showings can start Wednesday, February 18th as a vacant home. Will likely set an offer deadline as offers are received. This home will need repairs. We are looking for a cash or conventional offer. Discover a charming investment opportunity in the heart of Middletown Borough! This traditional detached home boasts 2,576 sq. ft. of potential, featuring 3 spacious bedrooms and 2 full bathrooms. Set on a manageable 0.11-acre lot, this property includes off-street paved parking, ensuring convenience for tenants or guests. The classic architectural style and solid frame construction provide a timeless appeal. With a strong rental market in the area, this home presents an excellent opportunity for investors seeking steady returns. Whether you're looking to renovate and increase value or maintain as a reliable rental, this property is a canvas ready for your vision. Don't miss out on this chance to invest in a warm and inviting community!
#PADA2050382

MIDDLETOWN

166 ANN STREET

None Beds

None Baths

2,576 Sq.Ft.

$155,000

MLS#: PADA2050382

This brand new 3 bed, 2 bath home is a buyer’s delight. The many upgrades include: floor to ceiling cabinetry, stainless steel appliances, double stainless steel sink, tile backsplash and recessed lighting. The open floor plans offers 8′ flat ceilings and a spacious living room. The main suite has a large walk-in closet, double 36″ vanity and an oversized corner shower. The home sits on large flat lot that backs up to a tree lined berm for additional privacy. Call today for an appointment!
#PADA2052222

MIDDLETOWN

32 ROSE AVENUE

3 Beds

2 Baths

1,200 Sq.Ft.

$139,900

MLS#: PADA2052222

Single family home in a quiet neighborhood. Situated on a corner lot in Royalton Boro. Home offers 2 bedrooms, full bath, kitchen, living and family rooms. Full unfinished basement. Back patio and shed for outdoor storage. Conveniently located to shopping, restaurants, airport and major highways.
#PADA2049974

MIDDLETOWN

240 R WATER STREET

2 Beds

1 Baths

821 Sq.Ft.

$105,300

MLS#: PADA2049974

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