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
238
# of Listings
3
Avg # of Bedrooms
$269
Avg. $ / Sq.Ft.
$654,201
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

19 Properties Found. Page 1 of 2.

Introducing FOXLEA FARM, A Stately Plantation Style Estate, where Southern Charm Meets Mountain Majesty – 58+/- Acres of Endless Potential! Welcome to your dream property—58+/- acres of scenic, cross-fenced pastureland nestled among breathtaking mountain views. This Southern gem is tailor-made for equestrian lovers, hobby farmers, or anyone seeking wide-open spaces with the comforts of modern living. A few of the Key Features Include: Panoramic Mountain Views in every direction, Automatic Waterers in each pasture—low maintenance, year-round convenience, Horse-Ready Barn with two stalls, Signature Magnolia Tree adding timeless Southern elegance, Home with Dual-Level Balconies—ideal for sunrise coffee or sunset unwinding, Cross-Fenced and ready for livestock or rotational grazing, Just Minutes from the Interstate—secluded but accessible, Possible Subdivide Opportunity—invest or expand! Whether you're looking to build your legacy homestead or develop for future value, this property offers rare versatility and classic Southern beauty. A place where refined elegance meets rustic beauty. Nestled amid rolling pastures and panoramic mountain views, this property boasts a classic English boxwood garden—a tranquil, evergreen sanctuary that adds both prestige and peace to the landscape. Whether you're strolling through boxwood-lined paths, sipping sweet tea on the balcony, or watching your horses graze at sunset, this property captures the romance of the South with timeless sophistication.
#VAFV2035852

MIDDLETOWN

1115 CHAPEL ROAD

3 Beds

2 Baths

2,969 Sq.Ft.

$2,999,900

MLS#: VAFV2035852

Introducing FOXLEA FARM, A Stately Plantation Style Estate, where Southern Charm Meets Mountain Majesty – 58+/- Acres of Endless Potential! Welcome to your dream property—58+/- acres of scenic, cross-fenced pastureland nestled among breathtaking mountain views. This Southern gem is tailor-made for equestrian lovers, hobby farmers, or anyone seeking wide-open spaces with the comforts of modern living. A few of the Key Features Include: Panoramic Mountain Views in every direction, Automatic Waterers in each pasture—low maintenance, year-round convenience, Horse-Ready Barn with two stalls, Signature Magnolia Tree adding timeless Southern elegance, Home with Dual-Level Balconies—ideal for sunrise coffee or sunset unwinding, Cross-Fenced and ready for livestock or rotational grazing, Just Minutes from the Interstate—secluded but accessible, Possible Subdivide Opportunity—invest or expand! Whether you're looking to build your legacy homestead or develop for future value, this property offers rare versatility and classic Southern beauty. A place where refined elegance meets rustic beauty. Nestled amid rolling pastures and panoramic mountain views, this property boasts a classic English boxwood garden—a tranquil, evergreen sanctuary that adds both prestige and peace to the landscape. Whether you're strolling through boxwood-lined paths, sipping sweet tea on the balcony, or watching your horses graze at sunset, this property captures the romance of the South with timeless sophistication.
#VAFV2038158

MIDDLETOWN

1115 CHAPEL ROAD

3 Beds

2 Baths

2,969 Sq.Ft.

$2,999,900

MLS#: VAFV2038158

Unlock the potential of a timeless landmark with the Wayside Inn, a historic gem nestled in the heart of Middletown, Virginia. This unique property not only boasts a rich history dating back to the 18th century but also offers 22 suites all with bathrooms, 3 bars (tavern, bourbon & Speakeasy, The RED HAT), huge entertaining space for events. This is a prime commercial opportunity with an expansive land for expansion. Just under 4 acres zoned B1. With 4 acres of commercially-zoned land at your disposal, envision the expansion possibilities that could elevate this historic landmark into a thriving hub of activity. Take advantage of the ample space to create a vibrant commercial district that complements the historic character of the Wayside Inn, making it a destination for locals and tourists alike. Situated in the picturesque Shenandoah Valley, the Wayside Inn offers a scenic backdrop that enhances the allure of any commercial venture. The expansive grounds provide ample room for outdoor amenities, gardens, or additional structures to further enhance the property's appeal. Benefit from the strategic location of Middletown, with easy access to major transportation routes. The Wayside Inn's proximity to popular attractions, historic sites, and a supportive local community makes it an ideal location for a successful and sustainable business venture. Don't miss the chance to own a piece of history with a promising future. The Wayside Inn presents a rare investment opportunity where historic charm meets commercial potential. Whether you're an entrepreneur seeking a unique venture or a developer with a vision, this property is your canvas to create something extraordinary. Seize the moment and transform the future of the Wayside Inn. Embrace the legacy, write the next chapter, and make this historic landmark a cornerstone of Middletown's thriving community. Fully running and doing great, we have changed management and its now positive cash flow. its prime for an owner occupant. call for details and appointments. Open to lease option and owner financing available. Kitchen and tavern are leased. Have grants applied for in the millions to renovate it. Have insurance claim coming for a new roof as well.
#VAFV2019018

MIDDLETOWN

7783 MAIN STREET

None Beds

None Baths

20,820 Sq.Ft.

$1,300,000

MLS#: VAFV2019018

Build your dream home on 20 acres in the scenic River Ridge community of Middletown, VA. This to-be-built Creveling model by Hepler Homes offers a well-designed layout with 4 bedrooms, 3.5 baths, and high-quality finishes throughout. The main level includes a gourmet kitchen with a tile backsplash, walk-in pantry, and open living areas leading to a 565 sq. ft. wraparound porch designed to maximize the property’s natural setting. A 575 sq. ft. attached two-car garage provides additional storage and convenience. Interior features include LVP flooring throughout, upgraded trim (1x6 base and 1x4 casing), Hardie plank siding, brushed nickel fixtures, a tankless water heater, 12 recessed lights, water treatment system, laundry sink in the home and garage, and a freestanding tub with a tiled shower in the primary suite. Additional baths include fiberglass tub/shower units and elongated toilets. A basement may be added for an additional fee. This 20-acre parcel offers gently rolling terrain with multiple potential building sites and approximately 400 feet of frontage on the North Fork of the Shenandoah River. The location provides a blend of privacy and accessibility, with proximity to Front Royal, Winchester, I-66, and I-81. The home shown is to-be-built; the lot is sold separately. This listing is offered in cooperation with the lot owner and Hepler Homes. Other floorplans and models are available; additional charges may apply. Don’t miss this opportunity to create a full-time residence, retreat, or long-term investment in the Shenandoah Valley.
#VAWR2012826

MIDDLETOWN

0 RIVER RIDGE DRIVE

None Beds

None Baths

N/A

$1,263,000

MLS#: VAWR2012826

New on site 4 days ago
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.
#VAFV2039508

MIDDLETOWN

0 RELIANCE

None Beds

None Baths

3.84 acres

$799,000

MLS#: VAFV2039508

Have you been looking for the perfect sophisticated and elegant historic home? Do you want everything; a gracious home, amazing space, acreage, a place for chickens, but also walkable and close to town? It sounds impossible, but you've found it! Welcome to historic Maplewood, circa 1872, know colloquially as The Tower. With no HOA and business B-1 zoning, this property presents endless possibilities, allowing dozens of potential uses! With stunning Italianate architecture and over an acre of land, this property is one in a million. This landmark home located in the heart of lovely downtown Middletown is a piece of history with all the modern conveniences. Rich with history, this amazing property was once the home and studio of John Chumley, a famous local artist. (The current owners have tons of photos and information about the history of the home that they'd love to share with you!) Too many amazing features to list; gorgeous high ceilings, original hardwood floors, wrap around built ins, huge windows, original millwork throughout, a generous kitchen and huge walk in pantry, fabulous mudroom, several outbuildings for storage and work space, an amazing chicken coop; the list goes on and on! Featuring four large bedrooms and two and half bathrooms, this home is spacious, beautiful, and elegant. The panoramic mountain views will take your breath away, especially from the tower studio room. And the home sits on a fantastic level lot behind public memorial land! All of this, located right in the center of town, so shopping and restaurants are just steps away. Middletown is an ideal location for commuters, with Rt 37, I-66 and I-81 within just a few minutes drive, not to mention all the natural beauty, activities, and amenities of the Shenandoah Valley. This is the one!!!
#VAFV2038812

MIDDLETOWN

2239 SIXTH STREET

4 Beds

2 Baths

2,944 Sq.Ft.

$649,900

MLS#: VAFV2038812

NEW PRICE! Owner has interior professionally painted! 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. Newly remodeled upper-level bath. 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.

$625,000

MLS#: VAWR2012638

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

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

Rare opportunity to own a beautiful parcel on River Ridge Drive offering privacy, potential, and long-term value. This undeveloped lot provides the perfect canvas for a custom home, recreational retreat, or investment hold in an area experiencing steady land demand. Surrounded by natural beauty and located within close proximity to local amenities, this property offers both tranquility and convenience. Strategically priced based on current land market trends and buyer activity, this property is being marketed to attract qualified end users and investors alike. Ideal for out-of-state buyers, builders, or those seeking to secure land for future use. Don’t miss the chance to own land with flexibility, upside potential, and location appeal. 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

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.

$464,999

MLS#: VAFV2035268

Experience modern efficiency and refined comfort in this meticulously maintained 4-bedroom, 2.5-bathroom home, built in 2021. Perfectly positioned for commuters, this property offers a prime central location just minutes from Winchester and Front Royal, with immediate access to major routes I-81 and I-66. Middletown is a small town rich in history. Emmet Steet only has 27 homes on it and ends in a cul-de-sac! Key Property Highlights: Energy Independence: Includes FULLY PAID-FOR solar panels installed in 2023. (A $20K investment!) Designer Interiors: The main level features hard surface flooring upgrades and an open-concept layout. The gourmet kitchen is anchored by premium granite countertops, perfect for both daily living and upscale entertaining. Upstairs laundry and a private owner's wing. Superior Outdoor Living: Step out onto an expansive TimberTech deck, a high-end composite addition that offers the beauty of wood without the maintenance of staining or sealing. This durable space is engineered to resist fading and mold for decades. Room to Grow: In addition to four spacious bedrooms, this home features a large unfinished basement, providing a blank canvas for a future recreation room, home gym, or extra living suite. Modern Convenience: Includes an attached 2-car garage and a 2021 build date, ensuring all systems, from HVAC to roofing, are in prime condition for a move-in ready experience. The BIRCH model offers a higher bedroom count without breaking the bank! The owner invested over $25K in upgrades in this home when it was built. LEVOLOR brand, top down/bottom up blackout blinds convey (over $2000 value)! This home provides an exceptional lifestyle opportunity, combining the peace of mind of a newer build with smart, sustainable upgrades that deliver immediate and lasting value. Don't miss out on this rare chance to own an energy-efficient gem in a highly desirable area on a cul-de-sac! It looks so new you will question if anyone has even lived in it! Make your appointment to see in person this home that shows like a model!! The information contained herein is for informational purposes only. RE/MAX Roots makes no representation as to the accuracy or reliability of the information. The buyer is to verify information provided and related to the property that is material to a buyer’s decision to purchase the property. All documents and other information attached to this listing are provided as a courtesy and should be researched and verified by the buyer agent.
#VAFV2038830

MIDDLETOWN

152 EMMET ST

4 Beds

2 Baths

1,742 Sq.Ft.

$459,900

MLS#: VAFV2038830

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.

$444,999

MLS#: VAFV2034546

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.

$439,999

MLS#: VAFV2035270

One-level living in the sought-after Village at Middletown! This move-in-ready home welcomes new owners with an open floor plan designed for comfortable living and easy entertaining. The living room flows seamlessly into the kitchen, creating a bright and inviting main living space. The spacious kitchen features a breakfast bar, ample table space, and access to a large, low-maintenance Trex deck—perfect for cookouts or relaxing outdoors. Main-level laundry adds everyday convenience. The primary suite offers a walk-in closet with generous storage and a private bath with shower. Two additional well-sized bedrooms and a full hall bath complete the main level. The full unfinished basement includes egress for a future bedroom, a rough-in for a full bath, and the potential to nearly double your living space. A two-car garage with additional storage and a concrete driveway provide plenty of off-street parking. Ideally located for commuters, just minutes to I-81 and I-66, with easy access to local shops, schools, and amenities.
#VAFV2039012

MIDDLETOWN

151 COUGILL

3 Beds

2 Baths

1,378 Sq.Ft.

$425,000

MLS#: VAFV2039012

1 2

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service