Middletown, MD Homes for Sale

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 inside. Boasting 5 bedrooms, 4 full baths, and 2 half

Denise Briggs Redfin Corp

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

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

Twilight Open House! Be the first to visit 5/14 from 5-7pm to see this hard to find property. Welcome to 2616 Quebec School Road—an exceptional opportunity in the highly desirable Middletown area offering space, flexibility, and modern updates situated on 2.74 acres. This expansive home features 5 bedrooms and 4.5 baths, including a fully connected in-law suite—perfect for multi-generational

Richard Phillips Northrop Realty

Tucked away on over 5 private acres, this chalet-style home is not your typical property – and that’s exactly the point. With soaring ceilings, expansive windows, and skylights throughout, the home has a great balance of natural light and surrounded by wooded views that give it a true treehouse-like feel. A cozy fireplace anchors the main living space, while hardwood floors and warm finishes add

Kathryn Royer Royer Select Realty

Price Improvement! This iconic 1937 Brick Tudor Revival residence and adjacent additional structure are being sold together, situated on two separately deeded parcels that share a well and septic system. The Tudor Revival home has been freshly painted and offers timeless character blended with thoughtful updates throughout. The kitchen features stainless steel appliances, a new cooktop, custom

Denise Perkins Kelley Real Estate Professionals

Welcome to this stunning residence, where over 5,500 square feet of thoughtfully designed living space meets the demands of everyday ease and luxury. Start your mornings on the charming front porch, the perfect place to take in the sunrise. As you step inside, you are greeted by the warmth of gleaming hardwood floors that flow seamlessly throughout the entire main level, unifying the open-concept

Emily Grimshaw Compass

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 also backs to serene woods, walking/jogging

Joseph McDonnell Corner House Realty

Now on market! This picturesque single-family home sits in the heart of beautiful historic Middletown. Meticulously cared for from top to bottom, this exceptional property is perfectly positioned on a premium lot with stunning views of Middletown’s historic steeples, the breathtaking South Mountain range, and the charm of a white-picket-fence community. Tucked within a small clustered

Tyler Charles Long & Foster Real Estate, Inc.

Welcome to this beautifully upgraded colonial nestled in the sought after Glenbrook golf community- backing to the 15th fairway. Relax, entertain and unwind in your resort style backyard with a stunning inground salt water pool, beautifully landscaped private back yard and new paver walkways. This light filled beauty is loaded with desirable features and upgrades offering nearly 5400 square feet

Christine Sherman Coldwell Banker Realty

Motivated seller with a new price!!! Property sold as-is, offering upside potential in a great location. Well suited for cash buyers. Welcome to 1936 Old National Pike, a historic, brick-constructed home built around the turn of the last century, situated on nearly 4 acres along Old National Pike in Middletown, MD. Investors, flippers, and restoration experts, attention! A rare opportunity in

Ellen Keyser Mackintosh, Inc.

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

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.

Enjoy main street living with BRAND NEW HIGH-END FINISHES INSIDE & OUT including structural updates on Main street in Middletown! THIS COMPLETELY RENOVATED and BEAUTIFULLY RESTORED HOME HAS BEEN UPDATED THROUGH-OUT WITH ALL BRAND NEW ITEMS INCLUDING FOLLOWING: Roof & underneath sheathing to ensure a solid foundation for new materials, Electrical updated to code, new Plumbing and components

Heather Ponce Maryland Elite Realtors

Don't miss out on this very well maintained all-brick rancher situated on a level, half acre lot! This charming home features many updates and newer features -- including roof, water treatment system, well pump and much more. The kitchen boasts of solid surface countertops, tile backsplash and stainless steel appliances. Entering the living room, you will find a brick hearth fireplace and bright

Dan Plombon Mackintosh, Inc.

Open House Saturday and Sunday 1-3pm. Beautifully updated townhome in sought after Glenbrook community backing to the Richland Golf club offering serene golf course views and an exceptional setting. Recent improvements include a brand-new architectural shingle roof, fresh paint, new carpet, and a stamped concrete patio. Gleaming solid oak hardwood floors and elegant accent molding highlight the

Richard Phillips Northrop Realty

Offer Deadline is Monday, May 11th, at 2pm. Enjoy country living right outside of downtown Middletown. This charming two bedroom, one bathroom home features fresh paint, stylish LVP flooring in the family room, beautiful granite countertops in the kitchen and a fenced in backyard. The hardwood staircase leads you to a small sitting area, full bathroom and two spacious bedrooms. Ample storage can

Ronald Wolfe Charis Realty Group

Welcome to this well cared for home in the heart of Middletown, located within the highly sought after Blue Ribbon school district. Lovingly maintained by the same family for the past 11 years, this home offers a comfortable layout and design for all. Walk in on the main level; which includes a spacious living room, dining room, family room, kitchen, and convenient half bath; perfect for both

Hilery Leatherman Charis Realty Group

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