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Middletown, MD Homes for Sale

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  • /58

    $774,900

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,603 Sq Ft

    411 Glenbrook Dr, Middletown, MD 21769

    Welcome to 411 Glenbrook Drive in the desirable Glenbrook community of Middletown. This home offers over 4,600 finished square feet of living space with a great layout, beautiful golf course views, and several recent updates. The main level features a two-story foyer, formal living and dining rooms, and a spacious kitchen with upgraded cabinetry, a large center island, and a bright morning room

    Agent Photo

    Jim Bass

    Real Estate Teams, LLC

    411 Glenbrook Dr, Middletown, MD 21769
  • /50

    $2,500,000

    • 4 Beds
    • 4.5 Baths
    • 6,578 Sq Ft

    9237 Frostown Rd, Middletown, MD 21769

    Five private acres above the Middletown Valley, with South Mountain on the horizon and protected conservation land on two sides. This is a home built around how you want to spend your days: coffee in a kitchen with two 12-foot walnut islands and an 18-foot NanaWall that opens straight to the deck, afternoons at the heated saltwater pool, evenings by the Kentucky sandstone fireplace with the whole

    Agent Photo

    Shelley Eyler

    Berkshire Hathaway HomeServices PenFed Realty

    9237 Frostown Rd, Middletown, MD 21769
  • /63

    $1,425,000

    $75K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 5,511 Sq Ft

    2802 Bidle Rd, Middletown, MD 21769

    Looking for new construction, but don't want to wait? This gorgeous 2025 built Craftsman is the perfect option! Like new, only better thanks to an investment of all the things that are a hassle to add to a new home - rear yard fence, plantation shutters and luxury shades, water softener/treatment system, an Amish garden shed and more! Move in now and do nothing but pack your personal belongings!

    Agent Photo

    J. D'Ann Melnick

    EXP Realty, LLC

    2802 Bidle Rd, Middletown, MD 21769
  • /29

    $550,000

    • 3 Beds
    • 2.5 Baths
    • 2,496 Sq Ft

    7820 Myersville Rd, Middletown, MD 21769

    ***Room to Breathe, Space to Grow, and Mountain Views to Come Home To***Set on 3.72 acres just minutes from the heart of Middletown, this 3-bedroom, 2.5-bath ranch offers the kind of space and versatility that's increasingly hard to find. Here, you can enjoy a peaceful country setting and mountain views while keeping shopping, dining, schools, and everyday conveniences within easy

    Agent Photo

    Sam James

    Long & Foster Real Estate, Inc.

    7820 Myersville Rd, Middletown, MD 21769
  • /90

    $989,000

    • 3 Beds
    • 3 Baths
    • 3,236 Sq Ft

    8939 Hawbottom Rd, Middletown, MD 21769

    Escape the subdivision life for a residence defined by scale, privacy, and rugged utility. Set on 32.39+/- acres, this cabin-style estate is built for those who want their permanent home to feel like a fortress of solitude without sacrificing modern comforts. The interior features a recently updated kitchen equipped with new appliances and granite countertops. While there is a propane furnace,

    Taylor Nitterhouse Whitetail Properties Real Estate, LLC

    8939 Hawbottom Rd, Middletown, MD 21769
  • /13

    $924,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    0 Mountain Church Rd Unit MDFR2080886, Middletown, MD 21769

    HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by Grossnickle Construction offers the perfect blend of luxury and comfort. The home features 3 spacious bedrooms, including a private primary suite, 2 full bathrooms, and a convenient powder room. This plan also includes 400 sqft rec room in the basement and the option for an upstairs bonus room. Enjoy the

    Brittany Reaver Real Estate Teams, LLC

    0 Mountain Church Rd Unit MDFR2080886, Middletown, MD 21769
  • /93

    $1,719,900

    New Construction
    • 5 Beds
    • 8 Baths
    • 6,026 Sq Ft

    3150 Bidle Rd, Middletown, MD 21769

    To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is a premier 12 lot luxury estate home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking

    Adam Ellison Long & Foster Real Estate, Inc.

    3150 Bidle Rd, Middletown, MD 21769
  • /33

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 2,208 Sq Ft

    7 Derr Ln, Middletown, MD 21769

    BACK ON MARKET! BUYERS HOME SALE FELL THROUGH! Welcome to 7 Derr Lane in the sought-after Villages at Foxfield—Middletown’s premier 55+ community—where Original Owners have meticulously maintained and thoughtfully upgraded this beautiful home, showcasing true pride of ownership everywhere you look. Perfectly positioned within walking distance to Middletown Park and its many amenities, this home

    Joseph McDonnell Corner House Realty

    7 Derr Ln, Middletown, MD 21769
  • /88

    $1,249,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,052 Sq Ft

    3130 Bidle Rd, Middletown, MD 21769

    To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking

    Adam Ellison Long & Foster Real Estate, Inc.

    3130 Bidle Rd, Middletown, MD 21769
  • /129

    $1,349,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 4,413 Sq Ft

    7453 Heritage Oak Terrace, Middletown, MD 21769

    To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking

    Adam Ellison Long & Foster Real Estate, Inc.

    7453 Heritage Oak Terrace, Middletown, MD 21769
  • /4

    $499,900

    Coming Soon Oct 2
    • 4 Beds
    • 2 Baths
    • 1,956 Sq Ft

    7217 Picnic Woods Rd, Middletown, MD 21769

    Hubert Brown Real Estate Teams, LLC

    7217 Picnic Woods Rd, Middletown, MD 21769
  • /7

    $1,148,990

    New Construction $36K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,421 Sq Ft

    5901 Cloudberry Ct, Middletown, MD 21769

    HOME TO BE BUILT! - Don't miss the final opportunity to build your new custom home! Experience the breathtaking mountain views and modern luxury in your new construction home to be built by Grossnickle Construction, nestled in the heart of Middletown Valley. This thoughtfully designed 4-bedroom, 3.5 bath home offers the perfect blend of elegance, comfort and functionality. Step inside to discover

    Jennifer Beall Charis Realty Group

    5901 Cloudberry Ct, Middletown, MD 21769
  • /74

    $665,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 3.5 Baths
    • 3,822 Sq Ft

    301 Cone Branch Dr, Middletown, MD 21769

    Welcome to this former model home on a spacious corner lot offering comfort, flexibility and inviting indoor and outdoor living. The main level features refinished hardwood floors, a dedicated office, a bright kitchen with granite counters and large island, and a family room with a wood-burning fireplace framed by a dramatic floor-to-ceiling brick surround. Just off the kitchen, the skylit

    Gregory Stevens Samson Properties

    301 Cone Branch Dr, Middletown, MD 21769
  • /52

    $539,900

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    4492 Jade Ct, Middletown, MD 21769

    Welcome to 4492 Jade Court, where a complete interior and exterior renovation meets an exceptional private backyard retreat. Situated on a generous .55-acre lot, this truly move-in-ready home offers 4 bedrooms, 2.5 bathrooms, approximately 2,200 square feet of finished living space, and an extensive list of major improvements.The exterior has been completely refreshed with a new

    Adam Druck Coldwell Banker Realty

    4492 Jade Ct, Middletown, MD 21769
  • /74

    $425,000

    • 3 Beds
    • 2 Baths
    • 2,580 Sq Ft

    205 Franklin St, Middletown, MD 21769

    Built in 1958 and tucked into the heart of historic Middletown, this distinctive all-brick rancher has a story all its own. Offering approximately 2,580 finished square feet—1,440 above grade and 1,140 finished below grade—on a .73-acre corner lot, the home was custom built by its original owners and reflects craftsmanship, character, and thoughtful design throughout.Tall ceilings and

    Bobbi Prescott RE/MAX Results

    205 Franklin St, Middletown, MD 21769
  • /45

    $428,900

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    400 Stone Springs Ln, Middletown, MD 21769

    Welcome home to this beautifully updated end-unit townhome in the highly sought-after Glenbrook community, now offering even more recent improvements—including a brand-new roof and additional interior refreshes. Modern updates, generous living space, and an unbeatable Middletown location come together to create a home you’ll love from the moment you arrive.This spacious three-level home

    Bobbi Prescott RE/MAX Results

    400 Stone Springs Ln, Middletown, MD 21769
  • /67

    $475,000

    $24K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,036 Sq Ft

    708 E Main St, Middletown, MD 21769

    Welcome to this charming 4-bedroom, 2-bathroom home ideally situated on Main Street in the heart of Middletown, offering the perfect blend of character, comfort, and convenience. Step inside to beautiful hardwood floors that flow throughout the main level, creating a warm and inviting atmosphere. The formal living room features a cozy wood-burning fireplace, making it the perfect place to gather

    Lori Rogers Keller Williams Realty Centre

    708 E Main St, Middletown, MD 21769
  • /40

    $375,000

    • 3 Beds
    • 4 Baths
    • 2,170 Sq Ft

    46 Boileau Ct, Middletown, MD 21769

    Welcome to 46 Boileau Ct, a beautifully renovated, move-in-ready home where thoughtful updates and timeless style come together. Fresh paint, new light fixtures, new appliances, and Google Nest technology add modern convenience throughout. Hardwood floors span the top two levels, complemented by spacious bedrooms and generous closets. The HVAC systems have been professionally serviced with

    Melissa Donnelly Redfin Corporation

    46 Boileau Ct, Middletown, MD 21769
  • /35

    $499,900

    • 4 Beds
    • 2 Baths
    • 1,862 Sq Ft

    718 E Main St, Middletown, MD 21769

    Welcome to this beautiful colonial in the heart of Middletown, MD, where small-town charm, community character, and a prime Main Street address come together on a generous half acre lot! There is SO MUCH potential to revitalize this home to your most creative imagination. Bathed in natural light throughout, this spacious 4-bedroom, 2-bath home features gleaming hardwood floors and a comfortable,

    Andrew Hopley Keller Williams Realty Centre

    718 E Main St, Middletown, MD 21769
  • /37

    $680,000

    • 5 Beds
    • 3 Baths
    • 2,820 Sq Ft

    21 E Main St, Middletown, MD 21769

    Step into a world of timeless elegance with this stunning Victorian home, a true masterpiece of craftsmanship and design. Built in 1900, this residence boasts and shows a life of owners who loved it and those who appreciated its unique architectural features. Beautiful hardwood floors throughout the entire home, including in the updated and modernized kitchen! Upgraded countertops and stainless

    Caleb Wilson Maryland Real Estate Group LLC

    21 E Main St, Middletown, MD 21769
  • /56

    $584,900

    $15K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,488 Sq Ft

    6838 Mountain Church Rd, Middletown, MD 21769

    Escape the ordinary with this one-of-a-kind mountain-inspired retreat set on more than 5 secluded acres of mature woodland. Designed to embrace its natural surroundings, this distinctive chalet welcomes the outdoors in with dramatic vaulted ceilings, walls of windows, and multiple skylights that fill the home with sunlight while showcasing peaceful forest views from nearly every room. The

    Chris Reeder Long & Foster Real Estate, Inc.

    6838 Mountain Church Rd, Middletown, MD 21769
  • /67

    $487,900

    • 3 Beds
    • 3.5 Baths
    • 2,583 Sq Ft

    4613 Granite Dr, Middletown, MD 21769

    Welcome to 4613 Granite Drive, a beautiful 3-bedroom, 3.5-bath Colonial in Crest Manor Estates with 2,583 finished square feet and the kind of space that makes it easy to feel at home.Step inside to hardwood floors and a main level with plenty of room for everyday living and entertaining. The kitchen is spacious and bright, with stainless steel appliances, plenty of room to gather, and a

    Joanna Brown Keller Williams Realty Centre

    4613 Granite Dr, Middletown, MD 21769
  • /33

    $350,000

    $49K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,824 Sq Ft

    319 S Church St, Middletown, MD 21769

    OPEN HOUSE SATURDAY 8/29 11AM-1PMWelcome to this charming 3-bedroom home right across the street from Memorial Park in the heart of Middletown. offering classic character, flexible living space, and convenient off-street parking . Step inside to find beautiful hardwood floors and timeless woodwork that add warmth and character throughout the home.The main level features a

    Lenny Grzeskiewicz Corner House Realty

    319 S Church St, Middletown, MD 21769
  • /56

    $675,000

    • 4 Beds
    • 3.5 Baths
    • 3,142 Sq Ft

    12 Dean Ln, Middletown, MD 21769

    WHERE HOME MEETS HOMETOWN! Beautifully built in 2019 and ideally located on a premium corner homesite, this exceptional Colonial offers the rare combination of a beautifully appointed, move-in-ready home and the welcoming lifestyle of Historic Middletown, one of Maryland's most desirable small towns. With 3 finished levels, new carpeting, a freshly painted interior, four bedrooms, 3 full and 1

    Cindy Durgin Monument Sotheby's International Realty

    12 Dean Ln, Middletown, MD 21769
  • /132

    $1,050,000

    • 4 Beds
    • 3.5 Baths
    • 3,130 Sq Ft

    19 E Main St, Middletown, MD 21769

    Carefully reimagined between 2018 and 2021 with over $1.5M in updates, this historic Main Street home now lives like a luxury boutique retreat hidden in the heart of Middletown — complete with a secret speakeasy concealed behind a swinging bookshelf, a breathtaking custom kitchen addition, and a covered courtyard entertaining area anchored by a stunning stone fireplace. Rich in history yet

    Bobbi Prescott RE/MAX Results

    19 E Main St, Middletown, MD 21769
  • /63

    $498,900

    Coming Soon Oct 2
    • 4 Beds
    • 3.5 Baths
    • 2,599 Sq Ft

    4316 Zircon Rd, Middletown, MD 21769

    Welcome to 4316 Zircon Drive, a well-cared-for Middletown home where thoughtful updates and pride of ownership show throughout. With 4 bedrooms, 3.5 baths, a flexible floor plan and a beautiful backyard, there is a lot here to appreciate.The kitchen features stainless steel appliances and a window overlooking the spacious fenced backyard. Just off the kitchen, the glass-enclosed porch is

    Joanna Brown Keller Williams Realty Centre

    4316 Zircon Rd, Middletown, MD 21769
  • /49

    $699,000

    • 5 Beds
    • 3 Baths
    • 3,206 Sq Ft

    200 Prospect St, Middletown, MD 21769

    This home is an absolute MUST SEE. This home has been immaculately maintained and features all of it's original charm. You will fall in love with the beautiful hardwood floors throughout this spacious 5 bedroom, 3 full bath colonial that features 3,200 square feet of living space along with a large 832 square foot basement, with outside entrance. This classic beauty is situated on a large,

    Brandon Ziska Coldwell Banker Realty

    200 Prospect St, Middletown, MD 21769
  • /116

    $1,235,000

    • 5 Beds
    • 5.5 Baths
    • 6,827 Sq Ft

    1 Wagon Shed Ln, Middletown, MD 21769

    Welcome to 1 Wagon Shed Lane, a stunning five-bedroom, five-full- and one-half-bath Colonial offering nearly 7,000 square feet of luxurious living space in the sought-after Glenbrook community of Middletown. Polished elegance, sophisticated details, and design-inspired finishes distinguish every level, including classic moldings, wainscoting, stately columns, gleaming hardwood floors, soaring

    Keri Weis Northrop Realty

    1 Wagon Shed Ln, Middletown, MD 21769
  • /17

    $415,000

    • 3 Beds
    • 1.5 Baths
    • 1,473 Sq Ft

    7101 Flint Ct, Middletown, MD 21769

    3 bed 1.5 bath split foyer with garage, walkout basement with den, office, and storage at the end of cul de sac. Replaced within the last 5 years: roof, hvac, sewer main, flooring, paint. Located in Fountaindale neighborhood. Middletown school district. 8 min drive to Golden Mile.

    Jonathan Minerick Homecoin.com

    7101 Flint Ct, Middletown, MD 21769
  • /2

    $150,000

    • Land
    • 10,454 Sq Ft
    • $625,000 per Acre

    Lot 1 E Green St, Middletown, MD 21769

    Charming 1/4 acre buildable on E. Green Street. The buyer of 19 E. Main Street will have the right of first refusal on the sale. Additional photos available on the 19 E. Main Street listing MDFR2082574.

    Bobbi Prescott RE/MAX Results

    Lot 1 E Green St, Middletown, MD 21769
  • /57

    $839,999

    $9K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,497 Sq Ft

    5 Dean Ln, Middletown, MD 21769

    Welcome to 5 Dean Lane, a stunning 4-bedroom, 4.5-bath home in the sought-after Middletown Glen community. Ideally located within walking distance of schools, parks, and the library, this home also enjoys a beautiful view of the neighborhood’s open common area directly across the street, creating a spacious and inviting setting . Also this exceptional home is also just minutes from the nature

    Erin Joyce Real Estate Innovations

    5 Dean Ln, Middletown, MD 21769
  • /42

    $499,900

    • 4 Beds
    • 3 Baths
    • 1,432 Sq Ft

    9001 Hollow Rd, Middletown, MD 21769

    *One or more photos in this listing have been virtually staged using AI*Completely Renovated & Move-In Ready! Welcome to this beautifully updated ranch-style home situated on a picturesque 2-acre lot in the heart of Middletown Valley. Every detail has been thoughtfully renovated, offering a bright, modern interior with quality finishes throughout. The open and inviting floor plan is perfect

    Catalina Sandoval RE/MAX Realty Centre, Inc.

    9001 Hollow Rd, Middletown, MD 21769
  • /38

    $335,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    7008 Mountain Church Rd, Middletown, MD 21769

    Welcome to 7008 Mountain Church Road, a beautifully renovated and move-in-ready home offering the best of country living with stunning mountain views.This charming two-story home has been thoughtfully updated with a brand new roof on the back and side porch, HVAC system, well pump, flooring and carpet, appliances, water heater, fixtures, fresh paint, and cathedral ceilings. The home also

    Jay Day LPT Realty, LLC

    7008 Mountain Church Rd, Middletown, MD 21769

Why Live in Middletown

Located 45 miles from Washington D.C., Middletown, Maryland is a small town that attracts those seeking a quieter lifestyle while still being within commuting distance of the capital. The town features a variety of home styles, including townhouses, ranch-style homes, large Victorian builds, and brick colonials, with prices ranging from $320,000 to $800,000. The community is known for its strong sense of togetherness, with frequent events that bring residents downtown. Middletown's public schools are highly rated, with Middletown Elementary, Middletown Middle School, and Middletown High all receiving commendable ratings. Outdoor enthusiasts will find plenty of things to do, such as hiking and kayaking at Catoctin Creek Park, sports activities at Remsberg Park, and various amenities at Middletown Park, including a disc golf course and dog park. Dining options are diverse, with local favorites like The Main Cup, Dempsey’s Grille, and Tapia’s on Main offering a range of cuisines. For fresh produce and local goods, the Middletown Farmer’s Market is a popular spot from May to October. Grocery shopping is convenient with a Safeway and Aldi nearby, and retail needs can be met at Target and Westview Promenade. Middletown offers a blend of community spirit, outdoor activities, and practical amenities, making it a desirable place for many.

Middletown, MD Home Prices

Middletown, MD
Median Home Price
$585,000
Median Sale Price
$574,200
-4% YoY
Avg. Price per Square Foot
$196
Median Single Family Price
$610,000
Median Townhouse Price
$423,000
Total Active Listings
33 listings
Market Conditions
3 Months of Supply
Seller's Market

Frequently Asked Questions

What is the average home price in Middletown, MD?
Homes for sale in Middletown, MD have an average home price of $694,274.
How many homes have sold over the last 12 months in Middletown, MD?
138 homes have sold in Middletown, MD over the last 12 months.
What is the average household income in Middletown, MD?
The average household income in Middletown, MD is $164K.
What are the most popular zip codes in Middletown, MD?
The most popular zip codes in Middletown, MD include 21769, 21702, 21703, 21773 and 21755.
How much do you need to make to afford a house in Middletown?
The median home price in Middletown is $585,000. If you put a 20% down payment of $117,000 and had a 30-year fixed mortgage with an interest rate of 7.03%, your estimated principal and interest payment would be $3,120 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $134K a year to afford the median home price in Middletown. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Middletown is $164K.
How are the schools in Middletown, MD?
Middletown, MD has highly rated public and private schools. Some of the best schools in Middletown based on Niche Grades are Lucy School, Myersville Elementary School and Middletown High School. Browse all the schools in Middletown, MD to learn more.
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