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
97
# of Listings
3
Avg # of Bedrooms
$329
Avg. $ / Sq.Ft.
$502,882
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

26 Properties Found. Page 1 of 2.

41.5 acres of prime interstate land perfect for a commercial or industrial development. Zoned acres B2 and remaining RA.
#VAFV2024154

MIDDLETOWN

226 RELIANCE

None Beds

None Baths

41.57 acres

$5,750,000

MLS#: VAFV2024154

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

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

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

4 Beds

3 Baths

N/A

$1,263,000

MLS#: VAWR2012826

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

5,335 Sq.Ft.

$999,900

MLS#: VAFV2037388

PRIVATE AND SECLUDED WITH A BEAUTIFUL MOUNTAIN VIEW. SPACIOUS CUSTOM-BUILT HOME ON 13 ACRES. GREAT VALUE - PRICED BELOW CURRENT TAX ASSESSMENT! GREAT COMMUTER LOCATION! Tucked away yet only a short drive to I-81, I-66, Rt. 522 and Rt. 340. Near historic Middletown and the Shenandoah River. Convenient to Winchester, Front Royal, Stephens City and Strasburg. Four bedrooms, including two main-level suites - one with a high ceiling, tall Palladian window, skylights, walk-in closets, and a luxury tiled bathroom with two vanities, elegant 4x6 walk-in shower and large soaking tub. Four full baths in all, each with tile. The great room features a dramatic vaulted ceiling, skylights and corner fireplace. Kitchen with double sinks plus a smaller sink, two lazy Susans, breakfast bar, and a practical covered side entrance from the garage with a pantry, closet, window seat, and shoe and coat racks, that's perfect for bringing in groceries no matter the weather. Separate formal dining room with built-ins, chair rail and crown molding. Enjoy the wrap-around, gazebo-style front porch, rear grilling deck and back yard patio. The oversized one-car garage is 19x26 with a work bench and loft. Circular driveway. The walkout basement offers two bedrooms. a full bath, and two more living areas with tile floors - a rec room large enough for a pool table and a cozy family room with a wood stove, brick hearth, and rustic wood doors. Also, a laundry room, large mechanical room and under steps storage. Fenced area for a gardening or pets. Zoned heating and cooling. Conveys with stainless steel kitchen appliances, washer and dryer, water softener, and propane generator. Per health department records, 3-bedroom septic/6-person occupancy.
#VAWR2012858

MIDDLETOWN

515 RIVER RIDGE DRIVE

4 Beds

4 Baths

4,144 Sq.Ft.

$799,000

MLS#: VAWR2012858

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

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

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

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

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.

$464,999

MLS#: VAFV2034546

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