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

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
107
# of Listings
3
Avg # of Bedrooms
$330
Avg. $ / Sq.Ft.
$553,800
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

297 Properties Found. Page 1 of 20.

Location is everything, and this home delivers. Enjoy the freedom of NO HOA while being just steps away from a beautiful Middletown Park, perfect for morning strolls, picnics, or easy access to green space. This home is designed for living and entertaining! An open kitchen and living area with hardwood floors throughout the main level. The fenced rear yard, with deck, provides privacy and space for pets or play. Downstairs, the finished basement with a built-in bar is the ultimate entertaining zone. It's priced perfectly for you to come in and add your finishing touches, transforming it into the modern space you've always envisioned. Imagine the joy of welcoming the new year from your new home!
#MDFR2074056

MIDDLETOWN

204 ROD CIRCLE

4 Beds

3 Baths

3,978 Sq.Ft.

$747,900

MLS#: MDFR2074056

Location! Location! Location! Discover 7109 Emerald Court — move-in-ready gem on a cul-de-sac in charming Middletown, at the base of Braddock Mountain with beautiful views. This Colonial delivers instant charm with 4 spacious bedrooms, 1.5 renovated baths, and a flexible main level ready for your personal touch. The eat-in kitchen opens to a large deck, ideal for relaxing or entertaining. The partially finished walk-out basement extends your living space and features plumbing rough-in for a wet bar, plus it leads to a fully fenced yard with a new 6-ft privacy fence—perfect for pets, play, and outdoor living. You’ll even find an additional washers/dryer hookup in the garage. NO HOA! You’ll enjoy quick access to shops, cafés, award-winning schools, parks, trails, downtown Frederick, and major commuter routes. Comfort. Convenience. Charm. Home is being sold AS-IS, Update to your liking, Price adjusted accordingly:)
#MDFR2074098

MIDDLETOWN

7109 EMERALD COURT

4 Beds

1 Baths

1,706 Sq.Ft.

$424,999

MLS#: MDFR2074098

Includes 500 SF of dedicated office space, high end trophy space, open floor plan layout, and 10 foot ceilings. Lease rate does not include utilities, property expenses, or building services. 1-5 year rental term. Former printing press / Valley Register historic building in charming downtown Middletown. Final touches could be made to fit to your needs, zoned for office or retail. Contact us now for details.
#MDFR2069680

MIDDLETOWN

123 MAIN ST W

None Beds

None Baths

N/A

$1,350

MLS#: MDFR2069680

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

Welcome to Candyland: Where Dreams Gallop Free! There hasn’t been anything like this to hit the Middletown market in over 30 years. Nestled amidst paradise for both equestrian enthusiasts and opulence living. Picture this: a sprawling 120-, plus ,acre horse farm that captivates the senses and ignites the imagination. Welcome to Candyland, where every corner is a sweet surprise waiting to be enjoyed. Imagine waking up to the gentle nicker of horses in the morning mist, the sun casting a golden hue over lush pastures named after your favorite candies. Here, life is a symphony of hoofbeats and birdsong, a harmonious blend of nature's beauty and human creativity. Candyland's crown jewel: a state-of-the-art main residence that redefines elegance and comfort. Step inside to discover an open floor plan that seamlessly merges modern design with timeless sophistication. From the grand foyer adorned with tasteful artwork to the gourmet kitchen equipped with top-of-the-line appliances, every detail exudes elegance..But Candyland isn't just about one magnificent house; it's a tapestry of refined living spread across three parcels, with five houses, each boasting its own distinct charm, consisting of four additional houses. Candyland wouldn't be complete without its world-class equestrian facilities. Horse barns fit for royalty stand ready to pamper your prized steeds, while several run-in sheds provide shelter and comfort. State-of-the-art waterers ensure that your equine companions stay hydrated and happy, while training facilities offer ample space to hone their skills and unleash their full ability. Perhaps one enchanting aspect of Candyland is the ability to ride through the scenic farm, or host a lavish soirée under the stars, the spirit of togetherness infuses every moment.In the fast-paced world we live in, finding a sanctuary where time slows down and memories are made is truly priceless. So why settle for ordinary when you can indulge in the extraordinary? Come experience the magic Candyland, where opulence, leisure, and equestrian excellence converge in perfect harmony. Your dream farm awaits – and it's sweeter than you ever imagined. CandyLand, consists of three parcels with a total of five houses on the property. Last but not least, this gorgeous property features two pools. Public water hook-up is available to the property. ( We know you are so excited to view this amazing property, however an appointment is required, please do not drive down CandyLand Ln, without an appointment). Thank you for understanding. ( The square footage listed is for the main residence.)
#DENC2062306

MIDDLETOWN

1343 BOHEMIA MILL ROAD

4 Beds

4 Baths

4,650 Sq.Ft.

$5,100,000

MLS#: DENC2062306

Welcome to Candyland: Where Dreams Gallop Free! There hasn’t been anything like this to hit the Middletown market in over 30 years. Nestled amidst paradise for both equestrian enthusiasts and opulence living. Picture this: a sprawling 120-, plus ,acre horse farm that captivates the senses and ignites the imagination, consists of 3 parcels, with five houses and two in ground pools on the property..Welcome to Candyland, where every corner is a sweet surprise waiting to be enjoyed. Imagine waking up to the gentle nicker of horses in the morning mist, the sun casting a golden hue over lush pastures named after your favorite candies. Here, life is a symphony of hoofbeats and birdsong, a harmonious blend of nature's beauty and human creativity. Candyland's crown jewel: a state-of-the-art main residence that redefines elegance and comfort. Step inside to discover an open floor plan that seamlessly merges modern design with timeless sophistication. From the grand foyer adorned with tasteful artwork to the gourmet kitchen equipped with top-of-the-line appliances, every detail exudes elegance..But Candyland isn't just about one magnificent house; it's a tapestry of refined living spread across three parcels, with five houses, each boasting its own distinct charm, with the potential for more. Candyland wouldn't be complete without its world-class equestrian facilities. Horse barns fit for royalty stand ready to pamper your prized steeds, while several run-in sheds provide shelter and comfort. State-of-the-art waterers ensure that your equine companions stay hydrated and happy, while training facilities offer ample space to hone their skills and unleash their full ability. Perhaps one enchanting aspect of Candyland is the ability to ride through the scenic farm, or host a lavish soirée under the stars, the spirit of togetherness infuses every moment.In the fast-paced world we live in, finding a sanctuary where time slows down and memories are made is truly priceless. So why settle for ordinary when you can indulge in the extraordinary? Come experience the magic Candyland, where opulence, leisure, and equestrian excellence converge in perfect harmony. Your dream farm awaits – and it's sweeter than you ever imagined. CandyLand, consists of three parcels with a total of five houses on the property. Public water hook-up is available. (The square footage listed is for the main residence) ( We know you are so excited to view this amazing property, however an appointment is required, please do not drive down CandyLand Ln, without an appointment). Thank you for understanding.
#DENC2069512

MIDDLETOWN

1343 BOHEMIA MILL ROAD

4 Beds

4 Baths

4,650 Sq.Ft.

$5,100,000

MLS#: DENC2069512

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

Welcome home to 8842 Hawbottom Road! This breathtaking property features a stunning custom built three bedroom two full and two half bath main house, two car detached garage and workshop (approximately 1,400 square feet), plus a secondary three bedroom two full bath tenant house, situated on over 82 acres with 360° views, plus Frederick County approved subdivision rights - need we say more! Arriving to the property you'll instantly feel at home, quietly tucked away, while still conveniently located near everything that Middletown and Frederick County have to offer! First, let's welcome you to the main house, custom built in 2021, with thoughtful design choices combining luxury and comfort throughout, this home is simply perfect. Stepping in from your inviting covered front porch you'll find the main level featuring a two-story family room with wood burning fireplace, gourmet kitchen, dining area, guest half bath, executive office with a second wood burning fireplace and access to a side deck overlooking the property, plus your primary suite with a private full bath, dual walk-in closets and additional access to the side deck. The main level also offers a convenient pantry area with laundry, beverage fridge, and an additional half bath directly off the attached garage. The upper level of the home features a spacious loft, two additional bedrooms and full hall bath. The lower level of the home is unfinished, but offers endless opportunities with a walkout patio door and full windows for additional bedrooms if desired. Stepping into the backyard of the main house you'll find a covered patio, perfect for entertaining, as well as an additional uncovered patio. Second, we welcome you to the tenant house. Stepping in from your covered wrap around porch you'll find your main level which features a living room, dining room, kitchen, foyer and full bath. The upper level then features three bedrooms and additional full hall bath. The unfinished lower level offers your laundry area plus ample storage. Outside of the tenant house you'll find a large fenced yard plus a brand new roof. Additionally on the property you will find a stocked pond with a small dock. Beyond the existing features of the home, Frederick County has confirmed sub division rights, if desired. The property can be subdivided for up to three lots plus a remainder, or up to five lots plus a reminder if utilizing the Ag Cluster development option (additional documents available). Don't miss your chance to call this incredible property your very own!
#MDFR2058510

MIDDLETOWN

8842 HAWBOTTOM ROAD

3 Beds

2 Baths

3,477 Sq.Ft.

$2,200,000

MLS#: MDFR2058510

Welcome home to 8842 Hawbottom Road! This breathtaking property features a stunning custom built three bedroom two full and two half bath main house, two car detached garage and workshop (approximately 1,400 square feet), plus a secondary three bedroom two full bath tenant house, situated on over 82 acres with 360° views, plus Frederick County approved subdivision rights - need we say more! Arriving to the property you'll instantly feel at home, quietly tucked away, while still conveniently located near everything that Middletown and Frederick County have to offer! First, let's welcome you to the main house, custom built in 2021, with thoughtful design choices combining luxury and comfort throughout, this home is simply perfect. Stepping in from your inviting covered front porch you'll find the main level featuring a two-story family room with wood burning fireplace, gourmet kitchen, dining area, guest half bath, executive office with a second wood burning fireplace and access to a side deck overlooking the property, plus your primary suite with a private full bath, dual walk-in closets and additional access to the side deck. The main level also offers a convenient pantry area with laundry, beverage fridge, and an additional half bath directly off the attached garage. The upper level of the home features a spacious loft, two additional bedrooms and full hall bath. The lower level of the home is unfinished, but offers endless opportunities with a walkout patio door and full windows for additional bedrooms if desired. Stepping into the backyard of the main house you'll find a covered patio, perfect for entertaining, as well as an additional uncovered patio. Second, we welcome you to the tenant house. Stepping in from your covered wrap around porch you'll find your main level which features a living room, dining room, kitchen, foyer and full bath. The upper level then features three bedrooms and additional full hall bath. The unfinished lower level offers your laundry area plus ample storage. Outside of the tenant house you'll find a large fenced yard plus a brand new roof. Additionally on the property you will find a stocked pond with a small dock. Beyond the existing features of the home, Frederick County has confirmed sub division rights, if desired. The property can be subdivided for up to three lots plus a remainder, or up to five lots plus a reminder if utilizing the Ag Cluster development option (additional documents available). Don't miss your chance to call this incredible property your very own!
#MDFR2058798

MIDDLETOWN

8842 HAWBOTTOM ROAD

3 Beds

2 Baths

3,477 Sq.Ft.

$2,200,000

MLS#: MDFR2058798

Lot 3 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 3 East spans a generous 7-acre homesite and has already been approved for a five-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 3 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!
#MDFR2069640

MIDDLETOWN

3150 BIDLE RD

5 Beds

4 Baths

5,153 Sq.Ft.

$1,990,900

MLS#: MDFR2069640

Lot 2 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 2 West spans a generous 6.1-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 2 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!
#MDFR2069604

MIDDLETOWN

7460 HERITAGE OAK TERRACE

4 Beds

3 Baths

3,782 Sq.Ft.

$1,664,378

MLS#: MDFR2069604

Lot 2 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 2 East spans a generous 4.3-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 2 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!
#MDFR2069764

MIDDLETOWN

3120 BIDLE RD

4 Beds

3 Baths

3,871 Sq.Ft.

$1,578,000

MLS#: MDFR2069764

Lot 203 is the last remaining lot in the Estates of Old Middletown, Section 2—an exclusive five-lot subdivision located on Sumantown Road within the Middletown School District. This 1.348-acre homesite is ideally situated at the end of a private common driveway and offers sweeping views of the Appalachian Mountains. Home packages are available through Grossnickle Construction, or you may bring your own plans to build the custom home of your dreams. The lot is approved for a 4-bedroom home, perc-tested, and permit-ready. Opportunities like this are rare—don’t miss your chance to own the final lot in this premier Middletown community.
#MDFR2072962

MIDDLETOWN

5916 CLOUDBERRY COURT

4 Beds

3 Baths

3,956 Sq.Ft.

$1,328,015

MLS#: MDFR2072962

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!
#MDFR2069580

MIDDLETOWN

7452 HERITAGE OAK TERRACE

4 Beds

3 Baths

3,252 Sq.Ft.

$1,326,574

MLS#: MDFR2069580

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