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
106
# of Listings
3
Avg # of Bedrooms
$335
Avg. $ / Sq.Ft.
$553,986
Med. List Price

Browse MIDDLETOWN Real Estate Listings

106 Properties Found. Page 2 of 8.

Lot 1 East at Heritage Oak Estates | To-Be-Built Custom Home Opportunity.  Don’t miss this rare opportunity to build your dream home in Heritage Oak Estates, an exclusive twelve-lot community by Atlantic Homes, nestled in the heart of the scenic Middletown Valley.  Located less than a mile from charming Main Street in Middletown, MD this enclave offers panoramic views of pastoral landscapes and surrounding mountains—all with no HOA restrictions.  Lot 1 East spans a generous 4.6-acre homesite and has already been approved for a four-bedroom septic system, with a private well already in place—ready for your dream home.  Choose from a range of fully customizable floor plans or bring your own design.  Each home will feature elevated standard finishes throughout, including: Masonry board exterior siding with stone water table; 10’ to 12' ceilings on the main level.  Lot sizes in the community range from 2 to 7 acres, each offering its own unique views and privacy.  Protective covenants ensure architectural integrity and long-term value—vinyl siding is not permitted, and minimum build standards apply.  Lot 1 East offers the perfect blend of rural tranquility, upscale living, and accessibility—all in one of Frederick County’s most desirable areas.  Photos and renderings are representative and for illustrative purposes only. All builder plans can be customized to fit your preferences.  Contact listing agent for available plans, site details, and to explore available homesite options and start designing your future dream home today at Heritage Oak Estates!
#MDFR2069796

MIDDLETOWN

3130 BIDLE RD

4 Beds

3 Baths

2,500 Sq.Ft.

$1,186,202

MLS#: MDFR2069796

Lot 1 West at Heritage Oak Estates | To-Be-Built Custom Home Opportunity.  Don’t miss this rare opportunity to build your dream home in Heritage Oak Estates, an exclusive twelve-lot community by Atlantic Homes, nestled in the heart of the scenic Middletown Valley.  Located less than a mile from charming Main Street in Middletown, MD this enclave offers panoramic views of pastoral landscapes and surrounding mountains—all with no HOA restrictions.  Lot 1 West spans a generous 2-acre homesite and has already been approved for a four-bedroom septic system, with a private well already in place—ready for your dream home.  Choose from a range of fully customizable floor plans or bring your own design.  Each home will feature elevated standard finishes throughout, including: Masonry board exterior siding with stone water table; 10’ to 12' ceilings on the main level.  Lot sizes in the community range from 2 to 7 acres, each offering its own unique views and privacy.  Protective covenants ensure architectural integrity and long-term value—vinyl siding is not permitted, and minimum build standards apply.  Lot 1 West offers the perfect blend of rural tranquility, upscale living, and accessibility—all in one of Frederick County’s most desirable areas.  Photos and renderings are representative and for illustrative purposes only. All builder plans can be customized to fit your preferences.  Contact listing agent for available plans, site details, and to explore available homesite options and start designing your future dream home today at Heritage Oak Estates!
#MDFR2069522

MIDDLETOWN

7452 HERITAGE OAK TERRACE

4 Beds

3 Baths

2,618 Sq.Ft.

$1,180,000

MLS#: MDFR2069522

MOVE-IN READY! This newly built home offers a rare opportunity to enjoy modern living on a 3-acre homesite in the highly regarded Middletown School District. Thoughtfully designed with both comfort and style in mind, it makes a striking first impression with its wide covered front porch and scenic wooded surroundings. Inside, the main level features an inviting, open layout filled with natural light and clean, modern finishes. A private office provides a quiet workspace, while the bright living and dining areas offer flexible spaces for gathering and entertaining. At the heart of the home is the showstopping gourmet kitchen, designed for both everyday living and hosting. It features white shaker cabinetry with warm wood accents, soft-close drawers, quartz countertops, double wall oven,  Cafe stainless steel appliances, striking pendant lighting, and a spacious walk-in pantry. The expansive center island with seating creates a natural place to gather. Upstairs, you’ll find four spacious bedrooms, three well-appointed baths, and a convenient second-level laundry room. The primary suite offers a relaxing retreat with abundant natural light, a generous walk-in closet, and a spa-like bath with quartz countertops and an oversized shower wrapped in floor-to-ceiling porcelain tile. Situated on a beautiful 3-acre lot with mature trees, this home brings together modern design, quality craftsmanship, and the comfort of new construction—all in a desirable Middletown setting. NO HOA, No City Taxes. Builder Incentives Available!
#MDFR2073332

MIDDLETOWN

3105 SUMANTOWN ROAD

4 Beds

3 Baths

5,111 Sq.Ft.

$999,990

MLS#: MDFR2073332

Experience peace and tranquility of life in one of Middletown's most desirable & beautifully maintained communities, "Sheridan Estates"—an intimate enclave of just 8 custom homes, offering an upscale yet welcoming atmosphere, perfect for those who value comfort, style, and serenity with NO HOA! A brief 5 miles to I-81 to Rt 66 makes it an easy commuting distance to downtown Washington DC.  Only 1 hour to the metro & 9.3 miles to the hospital, charming, downtown Front Royal, Shenandoah River & nearby Shenandoah State Park/Skyline Drive which features hiking trails & scenic overlooks. 
Bring all your furry friends & enjoy peaceful walks through your own private trails that wind through 11+ acres. Entertain the family and friends with the large in-ground swimming pool w/new liner, stone firepit & shed. Truly a gardener's paradise where you can enjoy growing your own vegetables, flowers, herbs, etc... while listening to the birds singing from the trees that surround this private sanctuary.
Step through the front door into the light filled 2 story foyer with main level office to the left and separate living & dining rooms to the right with a large bright conservatory, filled w/14 windows that beam with natural light. The large gourmet kitchen is a chef’s dream featuring GE Monogram & Profile appliances, custom 42” oversized cabinetry with lots of cabinets & drawers for all of your storage needs, quartz counter tops, double bowl sink with disposer, large island with prep sink, wall-oven w/microwave & warming drawer, recessed lighting & ceiling fan. The gas cooktop includes a built-in grille. 
This gorgeous stone front home features an extra-large wraparound porch & 3 car side load garage. 
The main level of the home features a soaring 2-story foyer w/chandelier, 2 foyer coat closets, hardwood flooring, 9 foot ceilings w/extensive crown moulding, decorative columns, recessed lights, chair rail & shadow boxes.  A cozy step down family room features 11-foot ceilings, recessed lighting, gas fireplace & ceiling fan adjacent to the large breakfast nook w/bay window & walkout door to rear deck & walk-in pantry complete the main level. 
This spacious 5996 sq ft home with 5 bedrooms & 6 baths is designed so each bedroom upstairs has its own full bath. The upper-level features 4 bedrooms (all with private ensuite bathrooms) & ceramic tile flooring and convenient laundry chute. The primary bedroom with high ceilings features a step up to a separate walk in closet and separate "spa like" bathroom w/double sinks, jetted tub, separate shower and water closet w/commode, bidet & linen closet. 
The finished basement features 9 foot ceilings, oversized rec room, craft room with sink and countertop + a 5th bedroom, full bathroom, linen closet, media/theater room, and ground level walkout exit. A home gym is located in the large utility room with lots of additional storage space. The home is equipped with satellite wireless/wired cable tv, high speed wireless satelite internet and is wired throughout with Cat5 cabling. There is plenty of parking on the asphalt driveway for an RV and includes an RV power hookup & auto sensor to notify you of any vehicles entering driveway.
 Don't miss out on your opportunity to own this incredible slice of heaven!

***RECENT RENOVATIONS INCLUDE:
New 2 Carrier Infinity HVAC units inside and outside with smart thermostats-6/8/2021
Both septic tanks pumped & inspected - 2/9/24
Replacement Septic pump & tank plumbing pipes - 10/3/24
Driveway sealed -8/19/22
New garage floodlight -5/25/25
New Stainless Steel GE dishwasher -4/12/25
Well pressure tank & switch -10/9/24
New toilet flush valves (all toilets)- 3/15/25
New Whole home water softener- 2/10/25
New Pool salt/chlorine generator cell -6/25/24
New pool pump & pool filter multiport valve - 2020/21
New pool plumbing control gate valves 5/16/24
New pool liner - 3/18/2023
Radon remediation system installed
#VAFV2037388

MIDDLETOWN

190 NEWELL DRIVE

5 Beds

6 Baths

5,996 Sq.Ft.

$999,900

MLS#: VAFV2037388

PDR Homes is offering house packages at Americus Manor, a private subdivision featuring three lots within the Middletown school district. The subdivision is adjacent to over 135 acres of parkland, ensuring serenity and seclusion. The pricing shown is for the Lexington model, elevation 4 on  Lot 2, a 2.37-acre partially wooded lot with an approved septic and existing well. PDR Homes is the exclusive builder at Americus Manor.  The photos showcase some of the house designs offered, which can be customized to fit your preferences.
#MDFR2071116

MIDDLETOWN

Lot 2 SUMANTOWN ROAD

3 Beds

2 Baths

3,200 Sq.Ft.

$940,865

MLS#: MDFR2071116

Options galore! Purchase or ground lease with potential seller financing for a qualified purchaser. I-81 Exit #302 is the Gateway entrance into the Historic Town of Middletown, Virginia. This is the last remaining lot at the corner of Reliance Road and Valley Ave (Rt #11). We have 3.84 acres zoned B2 highway commercial. You are surrounded by The Village at Middletown by Ryan Homes. Richmond American Homes are building 90 additional single family homes on the south end of town. Middletown is home to Historic Wayside Inn, circa 1797, Laurel Ridge Community College with 3,500 students and staff. Immediate neighbors include; Comfort Inn, McDonalds, Dollar General, 7-11, Liberty C-store with fuel depot, Sheetz C-store with fuel depot has recently opened on the east side of the interstate. Locate your successful business venture where the growth is happening.
#VAFV2024656

MIDDLETOWN

0 RELIANCE

None Beds

None Baths

3.84 acres

$799,000

MLS#: VAFV2024656

Step into modern comfort in this beautifully renovated Colonial-style home in sought-after Valley Overlook in Frederick.  Offering 4 bedrooms, 3 full baths, and 1 half bath, this spacious residence blends classic charm with fresh, contemporary updates throughout.

The main level welcomes you with a bright, open layout featuring a fresh kitchen, inviting living and dining spaces, and a convenient half bath.  Upstairs, you’ll find a serene primary suite with en-suite bath.  Three more generous bedrooms and a hall bath complete the upper level. 

The fully finished lower level adds even more versatility with a large recreation space, full bath, and walk-up access to the backyard—perfect for guests, hobbies, or movie nights.

Located in a well-established community close to parks, shopping, dining, and commuter routes, this home offers the best of Frederick living with nothing left to do but move in and enjoy!
#MDFR2072474

MIDDLETOWN

2431 QUEBEC SCHOOL ROAD

4 Beds

3 Baths

3,013 Sq.Ft.

$725,000

MLS#: MDFR2072474

Motivated Seller!! Welcome to the sought-after Jackson’s Meadow subdivision with no HOA! This spacious Quaker-built home was completely remodeled down to the studs in 2021, with everything new inside and out. Offering over 4,100 finished square feet across three levels and backing to the Sly Fox Golf Course, this property has room for everyone. On the upper level, you’ll find 4 bedrooms, including the oversized primary suite with a jetted tub, porcelain shower with glass roller door, and a large walk-in closet with built-ins. Convenient upstairs laundry includes washer and dryer. The main level is warm and inviting with hardwood floors, 9’ ceilings, crown and chair rail molding, and recessed lighting. The gourmet kitchen features granite countertops, a 7’ island with flat-top stove and hood, stainless steel appliances, and opens to a cozy family room with propane fireplace. A main level study with French glass doors makes a perfect office, while an additional bedroom and full bath provide main-level living flexibility. The finished walk-out basement adds even more possibilities. It includes a large recreation/living room, kitchenette, full bathroom, and a 6th bedroom. Plus, there’s an additional room that could serve as a potential 7th bedroom, office, playroom, or gym! Since purchase, the owners have added thoughtful upgrades, including a large deck, perfect for entertaining or relaxing while enjoying the established 1-acre lot. Other highlights include ample storage and an attached two-car garage. Just minutes to Front Royal and commuter routes, this home blends comfort, space, and modern convenience.
#VAWR2012424

MIDDLETOWN

43 LITTLE SORREL DRIVE

6 Beds

4 Baths

4,164 Sq.Ft.

$699,900

MLS#: VAWR2012424

New on site 2 days ago
Beautiful Stone Front Colonial in Sought-After Pineland Park

3,887 total finished square feet offering 6 bedrooms and 3.5 baths on a 1-acre lot. Located in the desirable Pineland Park neighborhood of Warren County, ideal for commuting via I-66 and I-81. Minutes to golf, wineries, hiking, shopping, and downtown Front Royal.

The Jefferson III model by H & H Builders features a stone front exterior, wide trim, interior columns, and 9-ft ceilings. Main level includes newly refinished hardwood floors throughout, a formal living room, and a formal dining room with chair rail and box ceiling detail. Spacious family room with corner gas fireplace opens to the kitchen with abundant cabinetry, countertop space, and breakfast area. Covered wrap-around front porch and rear covered porch provide great outdoor living spaces.

Upper level offers hardwood hallway floors and new carpet in bedrooms. Newly remodeled primary suite includes vinyl plank flooring, tiled bath with soaking tub, separate shower, and walk-in closet. Three additional bedrooms and upper-level laundry for added convenience.

Fully finished walk-out basement features tile flooring, kitchenette/wet bar, family room, two bedrooms, full bath, and ample storage—perfect in-law or guest suite.

New AC units; furnace less than 5 years old. 2-car front-load garage with concrete driveway and plenty of off-street parking. Over 1 acre of open yard to enjoy.
#VAWR2012638

MIDDLETOWN

76 KATIE LANE

6 Beds

3 Baths

3,888 Sq.Ft.

$685,000

MLS#: VAWR2012638

Tucked away on over 5 private acres, this chalet-style retreat feels like living in your own treehouse. Soaring ceilings, expansive windows, and skylights bathe the open interior in natural light, highlighting the warmth of hardwood floors and a striking fireplace centerpiece. The wraparound deck is perfect for morning coffee or evening sunsets, surrounded by nature. The oversized, detached two-car garage offers endless possibilities for storage, projects, or tinkering. Inside, you’ll find eclectic charm blended with modern updates: a beautifully refreshed kitchen featuring stainless steel appliances and granite countertops. Whether you’re seeking a private escape or a home with character, this property delivers both. Enjoy rustic serenity without sacrificing convenience—just 15 minutes to Middletown’s shops and dining, and within the desirable Middletown school district. A rare opportunity to own a one-of-a-kind home that truly captures the best of mountain-style living.  Roof - 2020, Skylights - 2020, Stove/Microwave - 2021,  Fridge 2023+, Water Softener/Neutralizer - 2022.
#MDFR2070626

MIDDLETOWN

6838 MOUNTAIN CHURCH ROAD

4 Beds

3 Baths

2,586 Sq.Ft.

$649,900

MLS#: MDFR2070626

Imagine relaxing on an refinished deck, listening to the birds, and watching wildlife as you take in the serene rolling hills and distant mountains of the Middletown Valley. Despite the peaceful surroundings, you’re only minutes from Main Street Middletown’s restaurants, schools, shops, and all the charm of small-town USA!

This beautiful ranch home sits on 3.59 acres and offers 3 bedrooms (with the potential for a 4th bedroom on the main level or additional bedrooms to be finished in the basement), 3 full baths, and 1,820 sq ft of finished living space on the main level—plus another 1,820 sq ft of unfinished space ready for you to build out and customize to your liking.

The outdoor space truly shines with a large 1,320 sq ft pavilion—perfect for family BBQs, reunions, and events—or for cracking crabs on a summer evening! Enjoy the above-ground private pool to cool off on sunny days, or relax on the shaded deck overlooking your private oasis as you sip your morning coffee or evening drink of choice to unwind. The property backs to woods, offering privacy, seclusion and room to explore your 3.59 acre retreat.

Car and workshop enthusiasts will love the detached 3-car, 1,124 sq ft garage with 10-foot bays and 12-foot ceilings, as well as the 2-car, 751 sq ft attached carport. All buildings, including the house, carport, garage, pavilion & shed, have new lifetime architectural roofs with transferrable warranty to new Owner!

This is country-style living at its best with all the modern amenities you expect—and even a few you don’t. Make it your own before someone else does!
#MDFR2072484

MIDDLETOWN

3226 BIDLE ROAD

3 Beds

3 Baths

3,640 Sq.Ft.

$649,000

MLS#: MDFR2072484

This ranch home located in a quiet Middletown neighborhood is a gem hidden in plain sight and full of surprises. First, it has 4,000 resplendent finished square feet, and second, it offers two levels of independent living. The floorplan flows seamlessly, providing the kind of breathing room you’ll appreciate, enhanced with an elegant color palette, natural light, and stunning hardwood floors that pull it all together. The living room easily provides the space for various seating configurations and offers a fireplace along the main wall to center around. It opens to the renovated kitchen, inviting with its pristine white cabinetry, backsplash, and eat-in island—and where you’ll find ample workspace and storage plus high-end stainless appliances and fixtures. The dining room sits adjacent with space for extras such as china cupboards or buffets. A bonus room affords decent space for an office, playroom, crafts or hobbies, etc. Conveniently
located next to the kitchen, a mudroom combines with the laundry area with storage cabinets and a utility sink. This level boasts four bedrooms and three full baths. The primary suite shines with the addition of a sliding barn door to separate the appealing attached bath plus a walk-in closet. The other bedrooms and baths are all lovely, matching the theme. The downstairs is a complete floor designed as an in-law suite or
rental. It boasts a full kitchen, comfortable living/dining area, bedroom, bath, and dedicated laundry room. The aesthetic matches the upstairs to a backdrop of LVP plank-style flooring. It contains a private separate entrance, and even its own parking. The home rests on .31 acres with a view of the mountains, along with plenty of trees and landscaped shrubs to enjoy. A screened-in porch adds another tranquil respite, as
does a covered porch stretching along the front of the home. A two-car attached garage provides space for vehicles or storage. This home has been updated, renovated, and carefully maintained—and presents a unique opportunity. But also, this residence is the ticket to enjoy Middletown’s quaint, historic downtown, well-rated schools, and peaceful atmosphere plus proximity to Winchester, Shenandoah Valley, and all the area has to offer.
#VAFV2037492

MIDDLETOWN

2140 SIXTH STREET

5 Beds

4 Baths

4,006 Sq.Ft.

$599,900

MLS#: VAFV2037492

Step inside-You'll love it! This is a home designed to impress and it can be your new home before the Holidays! Spacious and beautifully updated 6-bedroom is perfect for multigenerational living. A rare find- two master suites, dual family rooms and high-end upgrades throughout.  The home offers flexible space ideal for large families, guests, or home offices. Recent updates include a new roof, gleaming hardwood floors and one new ceramic bath. The updated kitchen shines with granite countertops, stainless steel appliances.  Having multiple gathering areas this home has a perfect layout for entertaining. The inviting layout makes this home ideal for family events, relaxation or hosing guest.    You won't be disappointed by the stunning landscape, multiple decks and it even has a handicap access ramp!   Additionally, the Home is conventionally located near the well-known Middletown Park. Don't miss your chance to make it yours-schedule your private showing today!
#MDFR2066902

MIDDLETOWN

4311 ZIRCON ROAD

6 Beds

4 Baths

3,072 Sq.Ft.

$599,000

MLS#: MDFR2066902

* BUILDER'S END-OF-YEAR CLOSEOUT! LIMITED TIME OFFER…. CALL TODAY for details! *
The home you have been admiring is now available! There are so many beautiful features in this Woodland Hills model home and they can be yours without the wait time of a new home build. The Osprey model has 2,898 sq ft with 4 bedrooms and two and a half bathrooms. With ample storage and counter space, the kitchen will be where the family and guests will want to gather. The beautiful granite counters, oversized island and under-cabinet lighting are a few of the custom features that you will enjoy. Soak up the sun all year round in the 12x14 sunroom that is situated just off the great room area. A gas fireplace and built-in bookshelves are the natural focal point of the living room area. Also on the 1st floor is the flex room, study, laundry room, powder room and a mudroom area with a bench seat, coat hooks and lockers. The second floor has 4 larger bedrooms and 2 bathrooms. The master bath, with it's ceramic tile floor, tiled shower and soaking tub, will be your place to retreat and pamper yourself at the end of the day. The hall bath has a tub/shower. The unfinished basement features 9' poured concrete walls. You also have the convenience of a central vac system. This home is situated on a corner homesite and has easy access to Vine Street and I-283. Although loaded with custom features, this home is priced well below replacement cost.
#PADA2048296

MIDDLETOWN

195 MAGNOLIA DRIVE

4 Beds

2 Baths

2,898 Sq.Ft.

$599,000

MLS#: PADA2048296

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

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