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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

30 Properties Found. Page 1 of 2.

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

Motivated SELLER! Price Improvement! Schedule your showing today! 

LOCATION, LOCATION, LOCATION! Schedule Your Showing today!!!

Welcome home to this charming 4-bedroom colonial, situated on a cul-de-sac in a highly desirable Middletown neighborhood, known for its Blue Ribbon schools and friendly, welcoming community!

Step inside and feel immediately at home. This beautiful property features recent updates, spacious bedrooms, and bright, sun-filled rooms that create a warm and inviting atmosphere. Wake up to stunning mountain sunrises, enjoy family meals in the cozy eat-in kitchen, and unwind or host guests on the spacious corner lot, which has been fully fenced with a 6-foot vinyl privacy fence — ideal for backyard BBQs, pets, gardening, and playtime!

Downstairs, you’ll find a large recreation area with walk-out access to the backyard. Currently used as a fifth bedroom, this flexible space is ready for your home office, gym, game room, or media lounge.

With a new water heater, updated bathrooms, and plenty of potential to personalize, this home is move-in ready and full of possibilities.
#MDFR2070438

MIDDLETOWN

7109 EMERALD COURT

4 Beds

1 Baths

2,128 Sq.Ft.

$429,900

MLS#: MDFR2070438

Enjoy single level living in this ranch plan Three bedrooms and 2 full baths. The Master Suite has a large walk-in closet and a private bath. Laundry is situation near the master suite offering ultimate convenience. Large kitchen island, fireplace, deck off the great room and an unfinished basement with a 3-piece plumbing rough-in for future bathroom. This beautiful home is a must see! Call today to schedule your tour of our Onyx ranch style plan.
#VAFV2034546

MIDDLETOWN

104 MIDSUMMER LANE

3 Beds

2 Baths

1,610 Sq.Ft.

$424,999

MLS#: VAFV2034546

Gorgeous wooded 14 acre lot with a charming creek in the back.  The elevation allows a walk out lower level. Very close to the Middletown business district but far enough away for a country feel.  Your neighbors here will be million dollar homes with mountain views.  Rare & beautiful lot!
#MDFR2071406

MIDDLETOWN

8541 PETE WILES ROAD

None Beds

None Baths

14.27 acres

$399,999

MLS#: MDFR2071406

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

CHARMING RANCHER IN MIDDLETOWN, MD! Welcome home to this delightful 3-bedroom, 1.5-bath rancher in an excellent location. This well-maintained home features a cozy living room with fireplace, a kitchen, and a full basement with fireplace providing ample space for storage, hobbies, or future expansion. Hardwood floors extend through nearly the entire home! Enjoy the convenience of a paved driveway and an attached 2-car garage, perfect for parking and additional workspace. The spacious backyard offers plenty of room for outdoor entertaining, gardening, or simply relaxing. Located close to local schools, parks, and commuter routes, this home combines small-town charm with everyday practicality. Don’t miss your opportunity to make this charming rancher your new home! This property will be offered at auction on Friday, November 14, 2025, at 3:00 PM. The List price in no way represents a minimum, starting, or acceptable bid.
#MDFR2072534

MIDDLETOWN

10 LINDEN BOULEVARD

3 Beds

1 Baths

2,408 Sq.Ft.

$394,000

MLS#: MDFR2072534

Calling all savvy investors! Check out this fabulous Duplex in Middletown’s hot spot: two side-by-side Townhomes packed with potential, 2 exceptional Traditional Townhomes offering a rare blend of size, location, and income potential. Each unit features 4 bedrooms, 1 bath, and a generous 2,468 sq ft of living space, and additional lower level 840 sq ft space.  Located in a highly desirable area, unit 121 is currently being rented for $1,500/month plus utilities, while unit 123 is rented at $1,600/month plus utilities. Recent updates include new carpet, upgraded water feed pipes, and a new water heater.  The property offers electric baseboard heating, rear utility closets, 2 side porches, front porch, and a fenced backyard. With a 2025 appraisal of $439,000 and sold As-Is, this is a top-tier income-producing investment property for any portfolio. Don’t miss this opportunity in a prime location!
#PADA2045062

MIDDLETOWN

121-123 KEYSTONE AVENUE

None Beds

None Baths

2,968 Sq.Ft.

$379,900

MLS#: PADA2045062

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