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 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 Group
244
# of Listings
3
Avg # of Bedrooms
$266
Avg. $ / Sq.Ft.
$642,030
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

28 Properties Found. Page 2 of 2.

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

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

UNDER CONSTRUCTION. *$15,000 builder incentive; thru 2/28/26* 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 photos are of a similar home. - All taxes are estimated as this is new construction and has not been assessed.
#PADA2051536

MIDDLETOWN

134 MAGNOLIA DRIVE

3 Beds

2 Baths

1,895 Sq.Ft.

$392,581

MLS#: PADA2051536

UNDER CONSTRUCTION. *$15,000 builder incentive; thru 2/28/26* This Swallow model is a 3 BD, 2.5 BA, 1,798 sq. feet, center-unit townhome. With its nine foot ceilings and lots of natural light, this home feels comfortably spacious. Included in this kitchen is an island, granite counters, 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 ample space and lots of natural light which also features a private bath and walk-in closet. Also on the second floor are bedrooms two and three, a family bath and the laundry room, which is just steps from all bedrooms and bathrooms. This home has a full, unfinished, walkout lower level and a 2 car garage. A composite deck, as well as the patio below, affords additional outdoor living space. Interior selections may still be available. All taxes are estimated since this is new construction and has not yet been assessed. Interior photos are of a similar home. - All taxes are estimated since this is new construction and has not yet been assessed.
#PADA2051538

MIDDLETOWN

126 MAGNOLIA DRIVE

3 Beds

2 Baths

1,798 Sq.Ft.

$360,581

MLS#: PADA2051538

UNDER CONSTRUCTION. *$15,000 builder incentive; thru 2/28/26* This Swallow model is a 3 BD, 2.5 BA, 1,798 sq. feet, center-unit townhome. With its nine foot ceilings and lots of natural light, this home feels comfortably spacious. Included in this kitchen is an island, granite counters, 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 ample space and lots of natural light which also features a private bath and walk-in closet. Also on the second floor are bedrooms two and three, a family bath and the laundry room, which is just steps from all bedrooms and bathrooms. This home has a full, unfinished, walkout lower level and a 2 car garage. A composite deck, as well as the patio below, affords additional outdoor living space. Interior selections may still be available. All taxes are estimated since this is new construction and has not yet been assessed. Interior photos are of a similar home.
#PADA2051546

MIDDLETOWN

132 MAGNOLIA DRIVE

3 Beds

2 Baths

1,798 Sq.Ft.

$360,581

MLS#: PADA2051546

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

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

$325,000

MLS#: MDFR2061288

New on site 3 days ago
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 2 days ago
Welcome to 27 Nissley Drive in Middletown, PA, a beautifully maintained home that blends comfort, functionality, and timeless style—perfectly positioned on a desirable corner lot with a fully fenced yard for added privacy and outdoor enjoyment. Step inside to discover warm hardwood floors that flow throughout the main living spaces, creating an inviting and cohesive feel. The thoughtfully designed floor plan offers three well-sized bedrooms and two full bathrooms, providing flexibility for daily living, guests, or a home office setup. Natural light fills the home, enhancing its bright and welcoming atmosphere. The kitchen is a standout feature, equipped with stainless steel appliances, granite countertops, and ample cabinetry, making it as practical as it is stylish. Whether you’re preparing weeknight meals or hosting gatherings, this space offers the perfect balance of efficiency and elegance. The adjoining dining and living areas allow for easy entertaining while maintaining a cozy, comfortable flow. Downstairs, the finished basement adds valuable additional living space and endless possibilities. Use it as a family room, media room, home gym, playroom, or work-from-home area—the options are only limited by your imagination. This versatile space significantly expands the home’s usable square footage and enhances its overall appeal. Outside, the fenced-in yard offers a private retreat ideal for relaxing, entertaining, gardening, or accommodating pets. The corner lot location not only provides extra outdoor space but also adds curb appeal and a sense of openness rarely found. Whether enjoying morning coffee outdoors or hosting summer barbecues, this yard is designed to be enjoyed year-round. Located in an established neighborhood with convenient access to local amenities, schools, and major routes, 27 Nissley Drive offers both comfort and convenience. With its desirable features, thoughtful updates, and versatile living spaces, this home is truly move-in ready and waiting for its next owner to make it their own. Don’t miss the opportunity to tour this Middletown gem—schedule your showing today!
#PADA2056406

MIDDLETOWN

27 NISSLEY DRIVE

3 Beds

2 Baths

1,200 Sq.Ft.

$284,900

MLS#: PADA2056406

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

1,392 Sq.Ft.

$279,990

MLS#: MDFR2069270

New on site 1 day ago
Well-maintained 3 bedroom ranch home with finished basement and large back yard. One bedroom is currently being used as a dining room, but could be a flex area for an office or an additional family room. Enjoy peace of mind with a newer roof and the added efficiency of solar panels. A convenient carport adds everyday practicality, while the lovely backyard offers a perfect setting for relaxing, gardening, or entertaining. A warm and inviting home with thoughtful updates and great outdoor space.
#PADA2056322

MIDDLETOWN

16 BERKLEY DRIVE

3 Beds

1 Baths

1,200 Sq.Ft.

$255,950

MLS#: PADA2056322

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