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
256
# of Listings
3
Avg # of Bedrooms
$274
Avg. $ / Sq.Ft.
$638,003
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

27 Properties Found. Page 1 of 2.

Charming and move-in ready, this beautifully renovated 3-bedroom, 1-bath rancher at 47 E High Street in Middletown offers the perfect blend of comfort, convenience, and affordability. Whether you’re a first-time homebuyer or simply looking for easy, single-floor living, this home checks all the boxes. The property has been fully updated inside and out, giving buyers peace of mind with major improvements already completed. Enjoy the benefits of a brand-new roof, new siding, and all new windows, adding both curb appeal and energy efficiency. A stone driveway and detached one-car garage provide practical parking and storage, while the spacious layout inside offers room to grow. Step inside and you’ll find a bright and inviting living space with plenty of room for everyday living, entertaining, or relaxing after a long day. The three well-sized bedrooms provide flexibility for a home office, guest room, or growing family. With ample storage throughout the home, you’ll have space for everything you need without feeling cramped. Located in the heart of Middletown, this home puts you close to everything. Grocery stores, an elementary school, and daily conveniences are just minutes away. You’ll also be within easy reach of local favorites like Hops & Barleys and J&J Pizzaria and Grille, making dinner plans or weekend outings simple and enjoyable. Affordable homes that are this updated and this well-located don’t come around often. If you’re looking for a comfortable, low-maintenance home with modern upgrades and room to grow, 47 E High Street is a must-see.
#PADA2057498

MIDDLETOWN

47 E HIGH STREET

3 Beds

1 Baths

1,036 Sq.Ft.

$245,000

MLS#: PADA2057498

4 -bedroom, 1.5-bath single-story home with 1,439 sq ft on a 0.14-acre lot. Features living room, second living space, dining area, kitchen, and two storage shops. Roof functional; siding and gutters may need updates. Appliances included: fridge, freezer, stove. Window AC units and wood stove. Public water & sewer, electricity by REC. Conveniently located near Frederick County schools.
#VAFV2038900

MIDDLETOWN

2339 THIRD STREET

4 Beds

1 Baths

1,439 Sq.Ft.

$219,900

MLS#: VAFV2038900

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 home to this well-maintained 2-bedroom, 1-bath semi-detached ranch offering comfort, simplicity, and easy one-floor living in the desirable Rosedale community of Lower Swatara Township. With 1,176 square feet of living space, this home features an inviting open floor plan designed for comfortable everyday living. Inside, you’ll find a welcoming living room that flows into the eat-in kitchen complete with a breakfast bar, providing a great space for casual dining and gathering. A versatile bonus room adds extra flexibility and is perfect for an in-home office, den, exercise space, hobby room, or playroom. Situated on a spacious .22-acre corner lot, the property offers plenty of outdoor space to enjoy. Step outside to the large deck, ideal for relaxing or entertaining during the warmer months. Garden enthusiasts will love the prepared garden beds ready for spring planting, creating the perfect opportunity to grow flowers, herbs, or vegetables right at home. Additional highlights include a 1-car garage, thoughtful upkeep throughout including fresh paint and carpet, and the added benefit of no HOA. Conveniently located near major routes, shopping, and everyday amenities, this home combines low-maintenance living with outdoor enjoyment in a peaceful neighborhood setting.
#PADA2057452

MIDDLETOWN

1801 MOUNTAIN VIEW ROAD

2 Beds

1 Baths

1,176 Sq.Ft.

$199,900

MLS#: PADA2057452

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: Price just reduced. Tenants have been moved out. Home has been cleaned out. This home will need good amount of repairs and updates. We are looking for a cash or conventional offer. Discover an investment opportunity in the heart of Middletown Bor ough! 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

3 Beds

2 Baths

2,576 Sq.Ft.

$149,000

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. Located close to Harrisburg International Airport, with easy access to Harrisburg, Hershey, and Lancaster. Pine Manor is located just outside of Middletown - an all ages, pet friendly community. Call today for an appointment!
#PADA2052222

MIDDLETOWN

32 ROSE AVENUE

3 Beds

2 Baths

1,200 Sq.Ft.

$139,900

MLS#: PADA2052222

If you are in search of the perfect building lot that provides seclusion, yet has easy access to state maintained roads nearby. You've found it! Tremendous views of the Signal Knob Mountain from various lots! Perfect Dream Home Lot for the commuter looking to escape from the hustle of the city! Whether you want a House-on-the-Hillside Lot surrounded by seclusion, or a lot located close to the Private Common Use area for Lake Access, we have exactly what you're looking for. Only 3 lots remain out of 41!
#1000074677

MIDDLETOWN

COMFORTER LANE LOT 31

None Beds

None Baths

2.0 acres

$110,000

MLS#: 1000074677

Build your future in the heart of the Shenandoah Valley! Lot 6 Sixth Street in Middletown, VA offers a prime opportunity to secure .42 acres in a growing area with new construction happening all around. Whether you're ready to build now or prefer to hold as the area continues to develop, this property gives you flexibility and potential — with NO HOA. Perfectly positioned just minutes from I-81, this lot provides easy access to surrounding areas: only 9 minutes to Stephens City, 20 minutes to Winchester, and approximately 1 hour to Fairfax. Enjoy the convenience of commuting while still taking advantage of a quieter, small-town setting. Bring your vision and design the home you've been dreaming about. With growth happening nearby and a location that keeps you connected, this is a rare chance to secure land in an area poised for continued progress.
#VAFV2039744

MIDDLETOWN

LOT 6 SIXTH ST

None Beds

None Baths

0.42 acres

$100,000

MLS#: VAFV2039744

Don’t miss the opportunity to own this beautifully maintained manufactured home! Featuring 3 spacious bedrooms and 2 full bathrooms, this home offers both comfort and functionality. The primary suite includes a private full bath, creating the perfect personal retreat. Property includes a wheelchair ramp for convenient accessibility. Lot rent is 495 monthly Enjoy new vinyl flooring throughout the home, adding a modern touch and easy maintenance (kitchen excluded). Located in a desirable neighborhood close to shops, restaurants, and parks, this property offers convenience at its best. Plus, it includes parking space for one vehicle.
#PADA2056788

MIDDLETOWN

524 N PINE STREET

3 Beds

2 Baths

1,232 Sq.Ft.

$87,000

MLS#: PADA2056788

Recently placed Skyline DBLWDE 24x42 with 3 beds, 2 baths. Completely renovated in 2025. So if you like NEW, this will appeal to your taste for new. Affordable luxury 1 floor living. Kitchen appliances included. Not yet tax assessed or assigned. Located in Neighbors of Lisa Lake MHP. $645 monthly lot rent includes trash. Sewer $67. Water metered. Pet friendly (no dangerous breeds) all age community. Optional 1 yr home warranty available for purchase. Financing available for all credit scores. Quick occupancy! Walk to Lisa Lake, public transportation, restaurants. see 31 pics!
#PADA2050308

MIDDLETOWN

4 NELSON MANOR LANE

3 Beds

2 Baths

1,008 Sq.Ft.

$81,500

MLS#: PADA2050308

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