4,788

Middletown, MD Homes

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  • /113

    $2,500,000

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

    9237 Frostown Rd, Middletown, MD 21769

    Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hundreds of flowering trees, this retreat-like residence is wrapped by protected conservation land on two sides, delivering incomparable privacy and a serene stage for entertaining, work, and retreat. From the views of Middletown

    Agent Photo

    Shelley Eyler

    Berkshire Hathaway HomeServices PenFed Realty

    (240) 255-4650

    9237 Frostown Rd, Middletown, MD 21769
  • /45

    $2,750 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,300 Sq Ft
    • Townhouse for Rent

    33 Chester Ct, Middletown, MD 21769

    Beautifully maintained, nearly new 3-level townhome condo located in the desirable Franklin Commons community in Middletown. Built in 2022, this modern home offers approximately 2,300 sq ft of thoughtfully designed living space with 3 spacious bedrooms, 3.5 baths, and an open-concept layout filled with natural light. The main level features a bright and airy kitchen complete with stainless steel

    Gayle Bailey Keller Williams Realty

    33 Chester Ct, Middletown, MD 21769
  • /44

    $310,000

    Sold Jun 18, 2026

    1936 Old National Pike, Middletown, MD 21769

    • 4 Beds
    • 2 Baths
    • 2,824 Sq Ft
    • Built 1900

    Last Sold Summary

    • 33% Below List Price
    • $110/SF
    • 151 Days On Market

    Current Estimated Value $452,495

    Last Listing Agent Ellen Keyser Mackintosh, Inc.

    1936 Old National Pike, Middletown, MD 21769
    • /55

      Est $831,612

      Not Listed For Sale

      3 Wagon Shed Ct, Middletown, MD 21769

      • 5 Beds
      • 4.5 Baths
      • 3,180 Sq Ft
      • Built 2010
      3 Wagon Shed Ct, Middletown, MD 21769

      Last Sold Summary

      • 4 Days On Market

  • /63

    $1,500,000

    Open Sun 1PM - 3PM
    • 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

    (240) 363-9379

    2802 Bidle Rd, Middletown, MD 21769
  • /47

    $2,200 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,520 Sq Ft
    • Middletown School District

    28 Boileau Ct, Middletown, MD 21769

    Spacious 3-Bedroom Townhome in Historic Middletown Jefferson Heights Discover this beautifully updated 3-bedroom, 2.5-bath townhome in the desirable Jefferson Heights section of Middletown. This home features: Main Level: Spacious living and dining areas with hardwood floors. The living room opens to a large deck with stairs leading to an expansive backyard. A new kitchen boasts granite

    28 Boileau Ct, Middletown, MD 21769
  • /80

    $901,000

    Sold Mar 31, 2026

    3293 N Hill Ct, Middletown, MD 21769

    • 3 Beds
    • 2.5 Baths
    • 3,084 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Above List Price
    • $292/SF
    • 3 Days On Market

    Current Estimated Value $895,567

    Last Listing Agent Bobbi Prescott RE/MAX Results

    3293 N Hill Ct, Middletown, MD 21769
    • /56

      Est $556,117

      Not Listed For Sale

      6513 Schneider Dr, Middletown, MD 21769

      • 3 Beds
      • 2 Baths
      • 3,064 Sq Ft
      • Built 1983
      6513 Schneider Dr, Middletown, MD 21769

      Last Sold Summary

      • 5 Days On Market

  • /147

    $1,400,000

    Pending
    • 4 Beds
    • 6 Baths
    • 6,808 Sq Ft

    4209 Maryland Ct, Middletown, MD 21769

    Welcome to 4209 Maryland Court, a stunning retreat nestled in the hills of the Middletown Valley, offering breathtaking views of Maryland National Golf Course and the Catoctin Mountains. Set on a beautifully landscaped 3.15-acre lot, this exceptional residence blends timeless elegance with thoughtful modern upgrades, creating a serene and private setting. Inside, architectural details shine in

    Keri Weis Northrop Realty

    4209 Maryland Ct, Middletown, MD 21769
  • /2

    $1,545 Per Month

    • 2 Beds
    • 1 Bath
    • 1,150 Sq Ft
    • Condo for Rent

    4A N Church St, Middletown, MD 21769

    Robert Dent Homestead Leasing & Management

    4A N Church St, Middletown, MD 21769
  • /74

    $825,000

    Sold Aug 01, 2025

    8339 Palmer Rd, Middletown, MD 21769

    • 5 Beds
    • 3 Baths
    • 3,127 Sq Ft
    • Built 2007

    Last Sold Summary

    • $264/SF
    • 3 Days On Market

    Current Estimated Value $819,790

    Last Listing Agent Tony La Scola Welcome Home Realty Group

    8339 Palmer Rd, Middletown, MD 21769
    • /53

      Est $419,692

      Not Listed For Sale

      11 Wash House Cir, Middletown, MD 21769

      • 3 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 2007
      11 Wash House Cir, Middletown, MD 21769

      Last Sold Summary

      • 4 Days On Market

  • /72

    $775,000

    Under Contract
    • 5 Beds
    • 6 Baths
    • 3,296 Sq Ft

    216 E Main St, Middletown, MD 21769

    ***Highest & Best offers due Saturday, May 16 8PM***Featured in WASHINGTONIAN, this iconic Victorian “Painted Lady” in the heart of Middletown’s historic district, offering timeless architecture paired with modern comfort. This one-of-a-kind residence showcases striking curb appeal with its signature twin turrets, intricate woodwork, and charming front porch that sets the tone for what awaits

    Denise Briggs Redfin Corp

    216 E Main St, Middletown, MD 21769
  • /61

    $2,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • Townhouse for Rent

    22 Chester Ct, Middletown, MD 21769

    Stunning like-new townhome located in the heart of Middletown! This spacious 3-level colonial offers approximately 2,300 finished sq ft with 3 bedrooms, 2.5 baths, and an attached front-entry garage. Features include an open-concept floor plan, modern finishes throughout, abundant natural light, and generously sized bedrooms with en-suite baths. Conveniently located near shopping, dining, parks,

    Gayle Bailey Keller Williams Realty

    22 Chester Ct, Middletown, MD 21769
  • /72

    $435,000

    Sold Nov 04, 2025

    106 Stone Springs Ln, Middletown, MD 21769

    • 4 Beds
    • 3.5 Baths
    • 2,727 Sq Ft
    • Built 2006

    Last Sold Summary

    • $160/SF
    • 2 Days On Market

    Current Estimated Value $438,913

    Last Listing Agent Chad Bikle Keller Williams Realty Centre

    106 Stone Springs Ln, Middletown, MD 21769
    • /59

      Est $585,706

      Not Listed For Sale

      2801 Grandview Dr, Middletown, MD 21769

      • 4 Beds
      • 2.5 Baths
      • 2,021 Sq Ft
      • Built 1983
      2801 Grandview Dr, Middletown, MD 21769

      Last Sold Summary

      • 74 Days On Market

  • /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
  • /67

    $845,000

    Sold Oct 24, 2025

    510 Glenbrook Dr, Middletown, MD 21769

    • 4 Beds
    • 4.5 Baths
    • 4,920 Sq Ft
    • Built 2004

    Last Sold Summary

    • $172/SF
    • 6 Days On Market

    Current Estimated Value $868,257

    Last Listing Agent Shelley Eyler Berkshire Hathaway HomeServices PenFed Realty

    510 Glenbrook Dr, Middletown, MD 21769
    • /50

      Est $267,408

      Not Listed For Sale

      7324 E Springbrook Ct, Middletown, MD 21769

      • 3 Beds
      • 1.5 Baths
      • 1,320 Sq Ft
      • Built 1971
      7324 E Springbrook Ct, Middletown, MD 21769

      Last Sold Summary

      • 5 Days On Market

  • /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
  • /12

    $2,096,257

    Sold Feb 26, 2026

    7461 Heritage Oak Terrace, Middletown, MD 21769

    • 4 Beds
    • 2.5 Baths
    • 3,524 Sq Ft

    Last Sold Summary

    • $595/SF
    • 69 Days On Market

    Last Listing Agent Amos Martin, CCIM VCRE.CO

    7461 Heritage Oak Terrace, Middletown, MD 21769
    • /79

      Est $1,031,508

      Not Listed For Sale

      109 Broad St, Middletown, MD 21769

      • 9 Beds
      • 3 Baths
      • 4,390 Sq Ft
      • Built 1910
      109 Broad St, Middletown, MD 21769

      Last Sold Summary

      • 16 Days On Market

  • /2

    $950,000

    Open Fri 5PM - 7PM Coming Soon
    • 4 Beds
    • 5 Baths
    • 5,661 Sq Ft

    7331 Holter Rd, Middletown, MD 21769

    Overlooking Remsberg Park and set on 0.95 acres, this lovingly maintained, extensively expanded and renovated Middletown home offers 5,661 finished square feet, two private primary suites, exceptional gathering spaces, and a lifestyle centered around comfort, flexibility, and outdoor living. The eat-in kitchen was renovated in 2016 and features hand-painted, all-wood custom cabinetry by Reaver’s

    Devon Beckner Real Broker, LLC

    7331 Holter Rd, Middletown, MD 21769
  • /72

    $585,000

    Sold Oct 30, 2025

    9 Caroline Dr, Middletown, MD 21769

    • 4 Beds
    • 2.5 Baths
    • 2,616 Sq Ft
    • Built 1984

    Last Sold Summary

    • $224/SF
    • 39 Days On Market

    Current Estimated Value $596,703

    Last Listing Agent Julie Fritsch Mackintosh, Inc.

    9 Caroline Dr, Middletown, MD 21769
    • /62

      Est $629,578

      Not Listed For Sale

      2 Ivy Hill Dr, Middletown, MD 21769

      • 4 Beds
      • 2.5 Baths
      • 2,828 Sq Ft
      • Built 1993
      2 Ivy Hill Dr, Middletown, MD 21769

      Last Sold Summary

      • 54 Days On Market

  • /49

    $499,999

    Pending
    • 3 Beds
    • 2 Baths
    • 2,079 Sq Ft

    2 Lombardy Dr, Middletown, MD 21769

    Welcome to 2 Lombardy Drive, right in the heart of Middletown’s Woodmere neighborhood—just steps from historic Main Street, where you’ll find charming restaurants, local shops, walking trails, and the community gathering spaces that make this town so special. Schools are just up the street, and everyday life here feels connected, walkable, and easy. Built by Morgan Keller, this beautifully

    Bobbi Prescott RE/MAX Results

    2 Lombardy Dr, Middletown, MD 21769
  • /54

    $550,000

    Sold Oct 20, 2025

    6 Stine Ct, Middletown, MD 21769

    • 2 Beds
    • 2.5 Baths
    • 1,895 Sq Ft
    • Built 2010

    Last Sold Summary

    • $290/SF
    • 79 Days On Market

    Current Estimated Value $562,821

    Last Listing Agent Lauren Kremers Century 21 Redwood Realty

    6 Stine Ct, Middletown, MD 21769
    • /85

      Est $742,291

      Not Listed For Sale

      2313 Bidle Rd, Middletown, MD 21769

      • 3 Beds
      • 2 Baths
      • 1,860 Sq Ft
      • Built 1977
      2313 Bidle Rd, Middletown, MD 21769

      Last Sold Summary

      • 70 Days On Market

  • /10

    $489,900

    Coming Soon
    • 2 Beds
    • 2 Baths
    • 1,359 Sq Ft

    4 Lamar Ln, Middletown, MD 21769

    Welcome home to 4 Lamar Lane, a beautifully updated Admar-built rancher tucked away at the peaceful back of the highly sought-after Foxfield 55+ community in Middletown. Thoughtfully designed for easy living and filled with warmth and charm, this move-in ready home offers the perfect blend of comfort, convenience, and low-maintenance living. A covered front porch welcomes you home, while the

    Bobbi Prescott RE/MAX Results

    4 Lamar Ln, Middletown, MD 21769
  • /59

    $349,900

    Sold Aug 29, 2025

    6724 Mountain Church Rd, Middletown, MD 21769

    • 3 Beds
    • 1 Bath
    • 1,512 Sq Ft
    • Built 1965

    Last Sold Summary

    • $231/SF
    • 1 Day On Market

    Current Estimated Value $371,772

    Last Listing Agent Elle Smith J&B Real Estate

    6724 Mountain Church Rd, Middletown, MD 21769
    • /81

      Est $779,598

      Not Listed For Sale

      8221 Hollow Rd, Middletown, MD 21769

      • 4 Beds
      • 3.5 Baths
      • 3,244 Sq Ft
      • Built 2024
      8221 Hollow Rd, Middletown, MD 21769

      Last Sold Summary

      • 37 Days On Market

  • /76

    $662,000

    Open Sun 1PM - 3PM $10K PRICE DROP
    • 6 Beds
    • 3.5 Baths
    • 3,696 Sq Ft

    24 Young Branch Dr, Middletown, MD 21769

    This home offers EVERYTHING you move to Middletown for; small-town feel, walkability to parks, restaurants, library and shopping, top-rated schools, easy access to commuter routes and THE VIEW! That’s right- one of the few homes in the neighborhood that backs to OPEN SPACE, owned by the town, with a view of South Mountain! With 3,696 sq ft of living space, you’ll find a welcoming open floor plan

    Michelle Hodos Long & Foster Real Estate, Inc.

    24 Young Branch Dr, Middletown, MD 21769
  • /52

    $240,000

    Sold May 19, 2026

    417 W Main St, Middletown, MD 21769

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft
    • Built 1890

    Last Sold Summary

    • 20% Below List Price
    • $172/SF
    • 242 Days On Market

    Current Estimated Value $255,900

    Last Listing Agent Vicki Reyes RE/MAX Realty Centre, Inc.

    417 W Main St, Middletown, MD 21769
    • /8

      Est $943,677

      Not Listed For Sale

      3115 Sumantown Rd, Middletown, MD 21769

      3115 Sumantown Rd, Middletown, MD 21769

      Last Sold Summary

      • 3 Days On Market

  • /5

    $1,171,120

    New Construction Pending
    • 4 Beds
    • 5.5 Baths
    • 4,542 Sq Ft

    Lot 1 Sumantown Rd, Middletown, MD 21769

    PDR Homes is offering house packages at Americus Manor, a private subdivision featuring three lots within the Middletown school district. The subdivision is adjacent to over 135 acres of parkland, ensuring serenity and seclusion. This listing is for The Lexington, a masterpiece of luxury living, boasting 4 bedrooms, 4.5 bathrooms, and over 4,300 square feet of exquisitely crafted space. This

    Christina Poss Verdant Realty Group LLC

    Lot 1 Sumantown Rd, Middletown, MD 21769
  • /18

    $35,000

    Sold May 26, 2026

    0 Burkittsville Rd, Middletown, MD 21769

    • Land
    • 1.36 Acres
    • $25,735 per Acre

    Last Sold Summary

    • 11 Days On Market

    Last Listing Agent Debbie Hugo Samson Properties

    0 Burkittsville Rd, Middletown, MD 21769
    • /64

      Est $854,098

      Not Listed For Sale

      303 Ingalls Dr, Middletown, MD 21769

      • 5 Beds
      • 4.5 Baths
      • 5,004 Sq Ft
      • Built 2018
      303 Ingalls Dr, Middletown, MD 21769

      Last Sold Summary

      • 0 Days On Market

  • /77

    $1,395,000

    $105K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 3,112 Sq Ft

    2730 Marker Rd, Middletown, MD 21769

    Love history? Love farming? Love Middletown Valley? This trifecta is for YOU! Once a bustling nursery, this 37 acre farm in the heart of the valley offers so many possibilities! Starting with the original 1809 stone house, with the cold cellar, original cooking hearth and spring-fed well... it’s a step back in time for any history enthusiast. Phase two for this 1800s farm family was the pre-Civil

    Michelle Hodos Long & Foster Real Estate, Inc.

    2730 Marker Rd, Middletown, MD 21769
  • /45

    $460,000

    Sold Dec 02, 2025

    7103 Unakite Ct, Middletown, MD 21769

    • 3 Beds
    • 3 Baths
    • 2,184 Sq Ft
    • Built 1977

    Last Sold Summary

    • $211/SF
    • 92 Days On Market

    Current Estimated Value $470,395

    Last Listing Agent Lily Vallario EXP Realty, LLC

    7103 Unakite Ct, Middletown, MD 21769
    • /68

      Est $672,191

      Not Listed For Sale

      212 Ingalls Dr, Middletown, MD 21769

      • 4 Beds
      • 4 Baths
      • 3,042 Sq Ft
      • Built 2019
      212 Ingalls Dr, Middletown, MD 21769

      Last Sold Summary

      • 19 Days On Market

Showing Results 1 - 40, Page 1 of 18

Home Prices in Middletown, MD

Home Price Trends

Median Sale Price
$610,000
Median Single Family Sale Price
$650,000
Median Townhouse Sale Price
$410,000
Median 2 Bedroom Sale Price
$489,900
Average Price Per Sq Ft
$195
Number of Homes for Sale
18
Last 12 months Home Sales
129
Months of Supply
1.70
Median List Price
$649,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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