2,827

Homes in ZIP Code 21755

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  • /61

    $624,000

    $26K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,540 Sq Ft

    6113 Elaine Dr, Jefferson, MD 21755

    NEW PRICE! UNEXPECTEDLY SPACIOUS HOME IN THE MIDDLETOWN SCHOOL DISTRICT! Discover a true RETREAT where you can enjoy breathtaking, panoramic valley sunset views right from your backyard oasis. Completely renovated and expanded in 2019, this unique home delivers incredible scale, thoughtful design, and premium quality upgrades throughout. THE MAIN LEVEL & LIVING SPACES feature beautiful luxury

    Agent Photo

    Lynn Holland

    RE/MAX Realty Centre, Inc.

    6113 Elaine Dr, Jefferson, MD 21755
  • /20

    $4,600 Per Month

    • 4 Beds
    • 3.5 Baths
    • 4,745 Sq Ft
    • House for Rent

    6110 Holter Rd, Jefferson, MD 21755

    Property Id: 2758512 Start your mornings with coffee overlooking rolling fields, grazing horses, and mountain views from this exceptional four-bedroom, three-and-a-half-bath luxury home, located in Middletown school district. With approximately 5,000 square feet of finished living space, the property offers the privacy and peaceful surroundings of country living without sacrificing

    6110 Holter Rd, Jefferson, MD 21755
  • /28

    $1,150,000

    Sold Mar 03, 2026

    6208 Picnic Woods Rd, Jefferson, MD 21755

    • 1,960 Sq Ft
    • Built 1900

    Last Sold Summary

    • $587/SF
    • 61 Days On Market

    Current Estimated Value $1,115,656

    Last Listing Agent Deanna Rippeon Charis Realty Group

    6208 Picnic Woods Rd, Jefferson, MD 21755
    • /96

      Est $702,754

      Not Listed For Sale

      4514 Cherry Ln, Jefferson, MD 21755

      • 4 Beds
      • 3.5 Baths
      • 3,272 Sq Ft
      • Built 1977
      4514 Cherry Ln, Jefferson, MD 21755

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Troy Yates LPT Realty, LLC

  • /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
  • /51

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    4015B Jefferson Pike, Jefferson, MD 21755

    Completely remodeled 3-bedroom, 2-full-bath rental home in Jefferson! This beautifully updated property features a brand-new kitchen with modern cabinetry, new appliances, and elegant quartz countertops. Freshly renovated throughout, the home offers comfortable living spaces, a spacious yard, and a partially fenced backyard—perfect for outdoor enjoyment. Conveniently located in Jefferson with

    Rich Phillips Northrop Realty

    4015B Jefferson Pike, Jefferson, MD 21755
  • /2

    $690,000

    Sold Jun 01, 2026

    4702 Joe Foss Way, Jefferson, MD 21755

    • 4 Beds
    • 3 Baths
    • 3,267 Sq Ft
    • Built 2018

    Last Sold Summary

    • $211/SF
    • 2 Days On Market

    Current Estimated Value $687,001

    Last Listing Agent Bobbi Prescott RE/MAX Results

    4702 Joe Foss Way, Jefferson, MD 21755
    • /54

      Est $413,268

      Not Listed For Sale

      3804 Bedford Dr, Jefferson, MD 21755

      • 3 Beds
      • 2 Baths
      • 1,634 Sq Ft
      • Built 1972
      3804 Bedford Dr, Jefferson, MD 21755

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Kathy Custer Long & Foster Real Estate, Inc.

  • /44

    $600,000

    Pending
    • 8 Beds
    • 3 Baths
    • 4,044 Sq Ft

    2915 Fry Rd, Jefferson, MD 21755

    ***WOW PRICED BELOW MARKET VALUE FOR QUICK SALE*** Great opportunity for investor or owner occupant that does not mind doing some updates to get this home to it's full potential! Nestled on over 5 private acres in the scenic countryside of Jefferson, this spacious ranch-style home offers the perfect blend of privacy, flexibility, and peaceful Frederick County living. Surrounded by rolling

    Jay Day LPT REALTY, LLC

    2915 Fry Rd, Jefferson, MD 21755
  • /37

    $3,600 Per Month

    • 1 Bed
    • 2 Baths
    • 2,500 Sq Ft
    • House for Rent

    3880 Point of Rocks Rd, Jefferson, MD 21755

    Property Id: 2389827 The Guesthouse at Stone Leaf Farm is a fully furnished private nature retreat in Jefferson, MD, near Harpers Ferry, the Potomac River, vineyards, historic towns, and major commuter routes. Ideal for traveling professionals, remote workers, corporate relocations, medical professionals, guests between homes, or anyone seeking comfortable temporary housing for up to 28

    3880 Point of Rocks Rd, Jefferson, MD 21755
  • /64

    $805,000

    Sold Jul 16, 2026

    3938 Cherry Ln, Jefferson, MD 21755

    • 3 Beds
    • 3.5 Baths
    • 4,332 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Above List Price
    • $186/SF
    • 1 Day On Market

    Current Estimated Value $746,791

    Last Listing Agent Bobbi Prescott RE/MAX Results

    3938 Cherry Ln, Jefferson, MD 21755
    • /3

      Est $559,216

      Not Listed For Sale

      3646 Jefferson Pike, Jefferson, MD 21755

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft
      • Built 2017
      3646 Jefferson Pike, Jefferson, MD 21755

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Michele Young Compass

  • /13

    $680,000

    Coming Soon Sep 17
    • 4 Beds
    • 3.5 Baths
    • 3,466 Sq Ft

    3355 Westport Dr, Jefferson, MD 21755

    Jill Coleman RE/MAX Realty Centre, Inc.

    3355 Westport Dr, Jefferson, MD 21755
  • /7

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft
    • House for Rent

    3845 Jefferson Pike, Jefferson, MD 21755

    Welcome home! This beautiful single-family home offers the perfect blend of modern, high-end updates and peaceful country living on a spacious 1/4-acre lot. Boasting fantastic curb appeal with brand-new siding, this home has been thoughtfully remodeled from top to bottom and is ready for you to move right in.Key Features & Modern UpdatesGourmet Remodeled Kitchen: Fully updated with

    Katelyn Repoli Real Broker, LLC - Annapolis

    3845 Jefferson Pike, Jefferson, MD 21755
  • /55

    $694,900

    Sold Jun 22, 2026

    3810 Roundtree Rd, Jefferson, MD 21755

    • 4 Beds
    • 3.5 Baths
    • 3,738 Sq Ft
    • Built 1999

    Last Sold Summary

    • 1% Below List Price
    • $186/SF
    • 3 Days On Market

    Current Estimated Value $698,552

    Last Listing Agent Chris Reeder Long & Foster Real Estate, Inc.

    3810 Roundtree Rd, Jefferson, MD 21755
    • /27

      Est $424,590

      Not Listed For Sale

      3707 Jefferson Pike, Jefferson, MD 21755

      • 4 Beds
      • 2 Baths
      • 2,068 Sq Ft
      • Built 1891
      3707 Jefferson Pike, Jefferson, MD 21755

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Benjie Cone Samson Properties

  • /45

    $499,900

    Pending
    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    4415 Saint Marks Rd, Jefferson, MD 21755

    Welcome Home to this lovingly maintained All-Brick Rancher in Jefferson on a beautiful 1 acre corner lot with pastoral views of rolling Frederick County farmland abound - Coming Soon - Saturday, 9.12! 4 bedrooms, 2 full baths of main floor living. From the moment you walk through the front door entryway enjoy gleaming hardwoods greeting you with natural light-filled traditional floor plan. Eat-in

    JT Smith Compass

    4415 Saint Marks Rd, Jefferson, MD 21755
  • /44

    $3,900 Per Month

    • 3 Beds
    • 3 Baths
    • 1,536 Sq Ft
    • House for Rent

    3887 Shadywood Dr, Jefferson, MD 21755

    Welcome to 3887 Shadywood Drive — a beautifully updated home offering peaceful country living with modern style and thoughtful design. Situated on a private, fully fenced lot in Jefferson, this home stands out with quality finishes and a layout designed for both comfort and functionality. The main level features an open and inviting feel with updated flooring, a stylish kitchen, and seamless flow

    Chloe Rogers Samson Properties

    3887 Shadywood Dr, Jefferson, MD 21755
  • /53

    $665,000

    Sold Nov 21, 2025

    4738 Old Middletown Rd, Jefferson, MD 21755

    • 3 Beds
    • 2 Baths
    • 2,020 Sq Ft
    • Built 2021

    Last Sold Summary

    • $329/SF
    • 8 Days On Market

    Current Estimated Value $678,905

    Last Listing Agent Allie Ballew Samson Properties

    4738 Old Middletown Rd, Jefferson, MD 21755
    • /53

      Est $571,509

      Not Listed For Sale

      4695 Basilone Ln, Jefferson, MD 21755

      • 4 Beds
      • 2.5 Baths
      • 1,912 Sq Ft
      • Built 2019
      4695 Basilone Ln, Jefferson, MD 21755

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Allie Ballew Samson Properties

  • /27

    $349,988

    Pending
    • 3 Beds
    • 1 Bath
    • 1,157 Sq Ft

    4015 Jefferson Pike, Jefferson, MD 21755

    Welcome to this turn-key 3 bedroom 1 bath home in the heart of Jefferson, MD!! Offering an unbeatable Main Street location this charmer has a brand new Kitchen and Bath, brand new central air conditioning and heating, refinished original hardwood floors, new windows, newly painted and ready to go! Fenced flat rear yard with storage areas, carport and breezeway entrance! All Brick Exterior! Just a

    David Lipsman Douglas Realty

    4015 Jefferson Pike, Jefferson, MD 21755
  • /46

    $524,900

    Sold Jun 26, 2026

    3638 Jefferson Pike, Jefferson, MD 21755

    • 3 Beds
    • 2.5 Baths
    • 1,904 Sq Ft
    • Built 2016

    Last Sold Summary

    • $276/SF
    • 6 Days On Market

    Current Estimated Value $524,722

    Last Listing Agent David Wagner RLAH @properties

    3638 Jefferson Pike, Jefferson, MD 21755
    • /90

      Est $560,667

      Not Listed For Sale

      5426 Burkittsville Rd, Burkittsville, MD 21718

      • 4 Beds
      • 4 Baths
      • 2,944 Sq Ft
      • Built 1890
      5426 Burkittsville Rd, Burkittsville, MD 21718

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Joan McLernon Real Estate Innovations

  • /50

    $680,000

    $95K PRICE DROP Under Contract
    • 4 Beds
    • 4.5 Baths
    • 2,896 Sq Ft

    3823 Roundtree Rd, Jefferson, MD 21755

    Step into timeless elegance with this beautifully restored 1886 home, where historic charm meets modern luxury. Nestled on a nearly 4-acre estate, this exceptional property offers space, privacy, and breathtaking grounds filled with mature landscaping, gardens, and multiple outdoor living areas including decks, porches, a balcony, and outbuildings perfect for the avid gardener. Inside, the home

    Wendy Friend RE/MAX Results

    3823 Roundtree Rd, Jefferson, MD 21755
  • /59

    $409,000

    Sold Oct 22, 2025

    3901 Shadywood Ct, Jefferson, MD 21755

    • 4 Beds
    • 2 Baths
    • 1,562 Sq Ft
    • Built 1971

    Last Sold Summary

    • $262/SF
    • 49 Days On Market

    Current Estimated Value $431,848

    Last Listing Agent Brenda Myers RE/MAX Results

    3901 Shadywood Ct, Jefferson, MD 21755
    • /36

      Est $646,555

      Not Listed For Sale

      3434 Pecan Ct, Jefferson, MD 21755

      • 3 Beds
      • 2 Baths
      • 1,908 Sq Ft
      • Built 2017
      3434 Pecan Ct, Jefferson, MD 21755

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Valerie Vinson Century 21 Redwood Realty

  • /104

    $950,000

    $345K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,362 Sq Ft

    3419 Jefferson Pike, Jefferson, MD 21755

    Income Producing Investment Opportunity with Proven Short-Term Rental Revenue & Redevelopment Potential. Whether you're looking to continue a profitable short-term rental operation, hold for long-term appreciation, or unlock the site's full development potential, this property delivers on all fronts. Redevelopment Upside: Currently Zoned Ag with Public Water & Sewer, allowing for unique

    Tony 'C' Checchia VCRE.CO

    3419 Jefferson Pike, Jefferson, MD 21755
  • /43

    $581,000

    Sold Jun 17, 2026

    3721 Boyington Dr, Jefferson, MD 21755

    • 3 Beds
    • 3.5 Baths
    • 2,402 Sq Ft
    • Built 2019

    Last Sold Summary

    • 6% Above List Price
    • $242/SF
    • 4 Days On Market

    Current Estimated Value $573,576

    Last Listing Agent Ike Price Keller Williams Capital Properties

    3721 Boyington Dr, Jefferson, MD 21755
    • /55

      Est $707,146

      Not Listed For Sale

      3592 Lobaugh Place, Jefferson, MD 21755

      • 4 Beds
      • 2.5 Baths
      • 3,088 Sq Ft
      • Built 2024
      3592 Lobaugh Place, Jefferson, MD 21755

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Bobbi Farquhar Engel & Völkers Annapolis

  • /23

    $1,195,000

    New Construction Pending
    • 4 Beds
    • 3 Baths
    • 4,588 Sq Ft

    4422 Teen Barnes Rd, Jefferson, MD 21755

    HOME TO BE BUILT. Rare opportunity to build a new PDR Home on a spectacular 2.94-acre homesite overlooking the scenic Middletown Valley in the highly sought-after Middletown School District. This offering is a lot and home package with PDR Homes, known for quality craftsmanship, timeless architecture, and well-designed living spaces. This listing features the Lexington model, highlighted by an

    Christina Poss Verdant Realty Group LLC

    4422 Teen Barnes Rd, Jefferson, MD 21755
  • /53

    $541,500

    Sold Mar 25, 2026

    4812 Bennington Place E, Jefferson, MD 21755

    • 4 Beds
    • 3.5 Baths
    • 2,836 Sq Ft
    • Built 1998

    Last Sold Summary

    • 8% Above List Price
    • $191/SF
    • 4 Days On Market

    Current Estimated Value $540,272

    Last Listing Agent Steffan May Synergy Realty

    4812 Bennington Place E, Jefferson, MD 21755
    • /130

      Not Listed For Sale

      4737 Old Middletown Rd, Jefferson, MD 21755

      • 4 Beds
      • 2.5 Baths
      • 2,338 Sq Ft
      4737 Old Middletown Rd, Jefferson, MD 21755

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Jeff Cosgrove RE/MAX Realty Plus

  • /61

    $589,999

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    4108 Spring View Dr, Jefferson, MD 21755

    Welcome to 4108 Spring View Drive, where a scenic countryside creates the perfect Frederick County retreat. Situated on a 1-acre lot, this beautifully maintained 4-bedroom, 2.5-bath home offers the ideal balance of privacy, space, and convenience.Inside, you'll find over 2,100 square feet (plus over 1,000 square feet in the basement) of comfortable living space featuring classic hardwood

    Hamid Mohebbi Hyatt & Company Real Estate, LLC

    4108 Spring View Dr, Jefferson, MD 21755
  • /41

    $650,000

    Sold Jun 08, 2026

    4024 Manheim Ct, Jefferson, MD 21755

    • 5 Beds
    • 3.5 Baths
    • 3,708 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $175/SF
    • 24 Days On Market

    Current Estimated Value $650,258

    Last Listing Agent Andrew Hopley Keller Williams Realty Centre

    4024 Manheim Ct, Jefferson, MD 21755
    • /27

      Est $242,019

      Not Listed For Sale

      3860 Shadywood Dr Unit 3B, Jefferson, MD 21755

      • 2 Beds
      • 2 Baths
      • 896 Sq Ft
      • Built 1992
      3860 Shadywood Dr Unit 3B, Jefferson, MD 21755

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Troyce Gatewood Real Broker, LLC - Frederick

  • /13

    $1,900,000

    $1M PRICE DROP
    • 2,244 Sq Ft

    4144A Lander Rd, Jefferson, MD 21755

    Located less than one hour from Washington, D.C., Baltimore, and Gettysburg, the city of Jefferson is surrounded by hills, rolling pastures and views for miles . This 1900 two story 2244 sf residence (4144) is a rented tenant house with 3 bedrooms and one bath and the 1970 single family ranch 1400 sf residence (4144A) is a 3 bedroom one bath - both are occupied. The 89.13 acre farm is in the

    Kim Drapeau EXIT Realty Center

    4144A Lander Rd, Jefferson, MD 21755
  • /23

    $390,000

    Sold Jul 07, 2026

    5054 Broad Run Rd, Jefferson, MD 21755

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $244/SF
    • 23 Days On Market

    Current Estimated Value $394,214

    Last Listing Agent Luke Tate LPT Realty, LLC

    5054 Broad Run Rd, Jefferson, MD 21755
    • /5

      Est $246,163

      Not Listed For Sale

      3860 Shadywood Dr Unit 2B, Jefferson, MD 21755

      • 2 Beds
      • 2 Baths
      • 896 Sq Ft
      • Built 1992
      3860 Shadywood Dr Unit 2B, Jefferson, MD 21755

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Leigh Ann Fangmeyer RE/MAX Results

  • /83

    $520,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,094 Sq Ft

    4245 Horine Rd, Jefferson, MD 21755

    ** OFFER DEADLINE MONDAY 8/24 AT 5PM **Nestled on a scenic 2.14-acre lot with expansive front and rear yards, this 4-bedroom, 2-bath ranch home offers the perfect blend of space, comfort, and country living. The property is ideal for anyone dreaming of a homesteading lifestyle - the current sellers enjoy raising chickens and maintaining a produce and flower garden, showcasing just some of the

    Lisa Kittleman The KW Collective

    4245 Horine Rd, Jefferson, MD 21755
  • /53

    $428,850

    Sold Mar 31, 2026

    3648 Lander Rd, Jefferson, MD 21755

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1967

    Last Sold Summary

    • 7% Above List Price
    • $214/SF
    • 2 Days On Market

    Current Estimated Value $421,164

    Last Listing Agent Craig Marsh Marsh Realty

    3648 Lander Rd, Jefferson, MD 21755

Showing Results 1 - 40, Page 1 of 18

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