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
103
# of Listings
3
Avg # of Bedrooms
$320
Avg. $ / Sq.Ft.
$564,040
Med. List Price

Browse MIDDLETOWN Real Estate Listings

103 Properties Found. Page 3 of 7.

QUICK SETTLEMENT! Upgrades throughout, new roof, bathroom, kitchen, with all new stainless steel appliances. The renovated main bathroom has a beautiful new tub with ceramic tile and a spacious new vanity. In 2023 the driveway was paved, in 2021, the heat pumps were replaced.  Some of the features are over the top, like multiple master bedrooms, one on the first floor, one on the second floor, both with private bathrooms. The upstairs master suite has a jacuzzi tub along with a built-in vanity and, separate shower.  There are a total of 6 bedrooms and 4.5 baths, 2 family rooms.   Total of 3 walk-in closets and a storage room. The new wheelchair ramp gives one access to the first floor.  The outdoor living space is phenomenal, which includes multiple decks, a gazebo, and more! The landscaping is over-the-top beautiful, yet minimal maintenance with lots of perennials in place. The local outdoor parks are ideal for sports families. Local Fountaindale community park, and the well-known Middletown Park! This home has been maintained, upgraded and loved! A rare find! This could be the perfect multi-generational home, with a quick settlement! Just in time for the upcoming Holidays! If you want a car port or garage, that may be a possibility as well, reach out to the local zoning office for more specifics to confirm.
#MDFR2066902

MIDDLETOWN

4311 ZIRCON ROAD

6 Beds

4 Baths

3,072 Sq.Ft.

$599,000

MLS#: MDFR2066902

Prime commercial site.  This 1.54-acre property boasts a coveted B-2 zoning, making it an ideal location for business ventures.  Conveniently positioned just off Interstate 81 and a short drive from Interstate 66, this site offers excellent visibility, ensuring maximum exposure for any enterprise.  Situated between two well-known establishments, McDonald's and Econo Lodge, it benefits from high traffic and customer flow.
With public utilities readily available, the infrastructure is in place to support a wide range of commercial activities.  Moreover, the surrounding area is experiencing substantial residential growth, indicating a thriving market and potential customer base.  This commercial site's strategic location, zoning, excellent visibility, proximity to major highways, and supportive infrastructure make it an enticing prospect  for entrepreneurs looking to establish or expand their businesses in a rapidly developing area.
#VAFV2013246

MIDDLETOWN

RELIANCE ROAD

None Beds

None Baths

1.38 acres

$595,000

MLS#: VAFV2013246

Charming Secluded Cabin Retreat 

This stunning 3 bedroom, 1.5 bath log cabin is the perfect getaway, nestled on a private lot with ample space and amenities. Featuring exposed wood throughout, the home boasts a cozy and rustic ambiance that will make you feel right at home. 

The main level offers an open-concept living area with a fully equipped kitchen, complete with granite countertops and new appliances. Step outside to the wraparound deck and enjoy the beautiful wooded views, or take a dip in the above-ground pool and relax in the hot tub.

Upstairs, the loft area provides additional living space, while the main floor bedrooms offer comfortable sleeping quarters. An attached one-car garage and a separate two-car detached garage provide ample storage and parking.

Ideal for short-term rentals, this cabin is currently a successful vacation property and can be sold fully furnished, making it a turnkey investment opportunity. Gather around the fire pit in the evenings, or explore the nearby hiking trails - this private oasis has it all.

Don't miss your chance to own this one-of-a-kind retreat! Schedule a showing today.
#PADA2040594

MIDDLETOWN

1250 HIGHSPIRE ROAD

3 Beds

1 Baths

2,691 Sq.Ft.

$583,700

MLS#: PADA2040594

Welcome to this beautifully maintained Dulaney model by ADMAR Custom Homes, located in the sought-after 55+ section of the Foxfield subdivision in picturesque Middletown. Pride of ownership is evident throughout this home, lovingly cared for by its original owner.

Step inside to a welcoming ceramic-tiled foyer, offering easy access to the attached two-car garage and a conveniently placed powder room. The kitchen features an abundance of cabinet space and overlooks the living room. Two large corner windows bathe the breakfast nook in natural light, making it a cozy space to start your day.

The main level boasts gorgeous hardwood flooring throughout the spacious living room and primary bedroom. A set of sliding glass doors in the living room leads to a private outdoor patio — perfect for relaxing or entertaining guests. You'll also appreciate the main-level washer and dryer, offering convenient single-level living.

Upstairs, you'll find two additional bedrooms and a full bath, ideal for guests, hobbies, or a home office.

The fully finished basement adds even more living space, featuring wall-to-wall wood flooring, recessed lighting, and a warm, open atmosphere perfect for entertaining, game nights, or even dancing. A large utility room with ceramic tile, utility sink, and dedicated deep freezer outlet adds function, while a roughed-in bathroom is nearly complete — just waiting for your final touch.

The walk-out basement stairs lead to a lush green yard. This backyard oasis offers both charm and seclusion — a perfect retreat.

Don’t miss your chance to own this exceptional home — homes like this don’t stay on the market for long!
#MDFR2071176

MIDDLETOWN

1 KELLER LANE

3 Beds

2 Baths

3,229 Sq.Ft.

$574,900

MLS#: MDFR2071176

Prime Development Opportunity in Middletown, VA – 2 +/- Acres behind the Wayside Inn, Backing to Parkland.  Access can be from 1st street, or with the right deal from Main street

Unlock the potential of this 2-acre parcel of raw land, a developer’s dream located in the charming town of Middletown, VA.   This property offers a rare combination of versatility and scenic tranquility, as it backs directly to 20 acres of pristine parkland, providing natural beauty and privacy.
Key Features:   B1 Zoning: Allows for a wide range of uses, including single-family homes (up to 7), mixed-use buildings, nursing home, bakeries, auto shop or any other small commercial ventures.
    Prime Location: Situated in a growing community with convenient access to local amenities, schools, and major commuter routes, including I-81 and Route 11.
    Scenic Setting: Nestled against protected parkland, ensuring future owners enjoy serene views and outdoor recreation just steps away.
    Development Ready: Level and open terrain, making it easier to plan and execute your vision.

This parcel offers a fantastic opportunity for residential developers, entrepreneurs, or investors seeking a versatile property in a desirable area. Imagine a boutique housing community, a small business center, or a mixed-use project—whatever your vision, this land is ready to bring it to life.

Don’t miss out on this one-of-a-kind property in Middletown. Schedule a visit today and explore the possibilities!  The entire Wayside is also for sale,  just ask.
#VAFV2022930

MIDDLETOWN

7783 MAIN STREET

None Beds

None Baths

2.0 acres

$525,000

MLS#: VAFV2022930

Welcome to the beautifully crafted Lexington model—brand new and READY NOW in the desirable Greenwood Hills community!   This energy-efficient home offers nearly 2,000 sq. ft. of thoughtfully designed living space, with 4 spacious bedrooms and 3 full bathrooms, including a main-level bedroom and full bath w/ walk-in shower, perfect for guests, multi-generational living, or a home office. 
The kitchen features 36” painted cabinets w/ crown molding, elegant quartz countertops, floating shelves, stainless steel appliances with gas cooking, and a walk-in pantry with solid shelving. The kitchen flows seamlessly into the dining area and open family room, creating a welcoming space for both everyday living and entertaining. Upstairs, the primary suite provides a peaceful retreat, complete with a walk-in closet and private en-suite bath with tile shower. Two additional bedrooms and a hall bath complete the upper level. Additional highlights include a two-car garage, walk-out lower level ready to finish, and a 10 year home warranty for added peace of mind. Enjoy life in Greenwood Hills—a thoughtfully planned neighborhood with sidewalks, community benches, a modern park, and a scenic pond with an observation deck. Conveniently located with easy access to Route 283 and the PA Turnpike.
#PADA2045388

MIDDLETOWN

160 HARTFORD DRIVE

4 Beds

3 Baths

3,114 Sq.Ft.

$509,900

MLS#: PADA2045388

Enjoy single-floor living in this inspired ranch home! At the front of the home, you'll find two bedrooms flanking a full bath. Toward the back, there's a well-appointed kitchen nestled between an elegant dining room and generous great room. The laundry is located near the primary bedroom, which has a large walk-in closet and a private bath. You'll love the professionally curated finishes! Situated on a corner lot and backing to open common area.
#VAFV2035268

MIDDLETOWN

100 MIDSUMMER LANE

3 Beds

2 Baths

1,610 Sq.Ft.

$484,999

MLS#: VAFV2035268

20 Acres with River Frontage & Mountain Views 
0 River Ridge Road, Middletown, VA
Come build your dream home on this stunning 20-acre parcel tucked within a private community. Ideally located just minutes from Front Royal, Winchester, I-66, and I-81, this property offers the perfect balance of peaceful seclusion and easy access to nearby towns and amenities.
Enjoy  mountain views and direct frontage on the beautiful Shenandoah River — ideal for fishing, kayaking, and embracing nature’s serenity. With gently rolling terrain and potential building sites, the possibilities are endless for creating your full-time residence, weekend escape, or legacy property. Approximately 400 feet of frontage on the North Fork of the Shenandoah River.
Don’t miss this rare opportunity to own a private piece of the Shenandoah Valley.
#VAWR2011208

MIDDLETOWN

0 RIVER RIDGE DRIVE

None Beds

None Baths

20.0 acres

$480,000

MLS#: VAWR2011208

The main floor of this Coral home offers a large, uninterrupted space for relaxing and entertaining. The kitchen features a spacious center island and opens to the dining and great rooms. Upstairs, you'll find a convenient laundry, a full bath tucked between two generous bedrooms, and an inviting primary suite with a walk-in closet and private bath. This home is built a loft. To round out this home a basement is included and this beautiful home backs to common area.
#VAFV2035270

MIDDLETOWN

102 MIDSUMMER LANE

3 Beds

2 Baths

1,840 Sq.Ft.

$469,999

MLS#: VAFV2035270

Welcome to this beautifully renovated oversized farmhouse in the heart of Middletown Valley. Blending timeless character with modern updates, this 3-bedroom, 2-full bath home is move-in ready and full of charm. Step inside to find spacious living areas filled with natural light, a thoughtfully updated kitchen with quality finishes, and two full bathrooms that have been tastefully remodeled. Original farmhouse details are complemented by contemporary upgrades, creating the perfect balance of old and new. Enjoy the peaceful setting from the covered porch or entertain in the generous yard surrounded by scenic views as well as the 2 story mancave with workshop below and a living space above that can be updated to make a private office or den. With its ideal location close to Middletown’s shops, restaurants, and commuter routes this home offers both convenience and countryside tranquility.
#MDFR2070724

MIDDLETOWN

8109 OLD HAGERSTOWN ROAD

3 Beds

2 Baths

2,628 Sq.Ft.

$465,000

MLS#: MDFR2070724

Welcome to 25 Chester Court in Middletown, MD, a stunning end unit townhome. This spacious home offers 2472 square feet of modern living across three floors, featuring 3 bedrooms and 3.5 bathrooms. The main level boasts a contemporary kitchen with white quartz countertops, stainless steel appliances, and a large deck perfect for entertaining. The expansive open walkout basement includes a full bathroom, providing ample space for recreation or an additional living area. The home also features luxury vinyl plank (LVP) flooring on all three floors, and an upstairs laundry room for convenience. The oversized primary bedroom is a true retreat, complete with two walk-in closets and an en-suite bathroom with dual vanities and a large shower. Two additional guest rooms and a full hall bathroom complete the upper level. The property includes a one-car garage and plenty of parking in a quiet community. Enjoy the tranquility of this neighborhood while being close to local attractions, shopping, dining, and outdoor activities. This beautiful home is perfect for those seeking modern amenities and a peaceful living environment. Don't miss the opportunity to make 25 Chester Court your new home.
#MDFR2071442

MIDDLETOWN

25 CHESTER COURT

3 Beds

3 Baths

N/A

$454,900

MLS#: MDFR2071442

Investor Alert! High Cash Flow + Strong ROI + $10,000 Seller Assist! 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: $1,295/mo, 1BR/1BA Apartment: $1,070/mo (currently leased month to month - higher market rent potential), (2) 2BR/1BA Apartments: $1,595/mo each. - Total Monthly Gross Rent: $5,555
Annual Gross Income: $66,660 WOW!! CAP Rate of 14.1%, and Cash on Cash Return of 30%, 5-Year Projected Equity Growth (4% Appreciation) - $97,000!! 100% 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. Seller now offering $10,000 toward Buyer’s closing costs! Don’t miss this rare, high-yield investment opportunity in thriving downtown Middletown!
#PADA2048820

MIDDLETOWN

219 S UNION STREET

5 Beds

None Baths

4,086 Sq.Ft.

$450,000

MLS#: PADA2048820

Investor Alert! High Cash Flow + Strong ROI + $10,000 Seller Assist! 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: $1,295/mo, 1BR/1BA Apartment: $1,070/mo (currently leased month to month - higher market rent potential), (2) 2BR/1BA Apartments: $1,595/mo each. - Total Monthly Gross Rent: $5,555
Annual Gross Income: $66,660 WOW!! CAP Rate of 14.1%, and Cash on Cash Return of 30%, 5-Year Projected Equity Growth (4% Appreciation) - $97,000!! 100% 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. Seller now offering $10,000 toward Buyer’s closing costs! 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.

$450,000

MLS#: PADA2049614

This 2021-built home is situated on a corner lot with views of I-81. The property features a 20 ft by 10 ft rear deck for outdoor enjoyment. Interior upgrades include luxury vinyl plank flooring in the kitchen, dining area, and all bathrooms, plus white premium kitchen cabinetry. Six ceiling fans with lights are installed throughout (all bedrooms and living room). The home features an open-concept design connecting the family room, kitchen, and dining area. It includes 4 spacious bedrooms, each with walk-in closets, and a versatile bonus room suitable for various uses including a bedroom or office. The home has 2.5 bathrooms, a full unfinished basement, and an attached two-car garage. Located near downtown shopping and restaurants, the property is positioned at the junction of I-66 and I-81, approximately one hour from Washington, D.C. via I-66. The home is in excellent condition and offers convenient access to local amenities while providing a peaceful residential setting.
#VAFV2037012

MIDDLETOWN

163 EMMET STREET

4 Beds

2 Baths

2,726 Sq.Ft.

$440,000

MLS#: VAFV2037012

Middletown-3 Bedroom, 2 Bath all Brick Rancher with oversized 2 Car Garage.  Newer HVAC Unit, Windows and Roof.  1/2 acre level lot backs to open fields with mountain views.  Large Shed has electric and new roof.  Close to commuter RTS and Shopping.  Blue Ribbon Middletown Schools!
#MDFR2070800

MIDDLETOWN

4509 VALLEY VIEW ROAD

3 Beds

2 Baths

2,352 Sq.Ft.

$439,900

MLS#: MDFR2070800

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