Middletown, MD Homes for Sale

***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

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

Open House Saturday and Sunday 1-3 pm. Welcome to 2616 Quebec School Road, an exceptional opportunity in the highly sought-after Middletown area offering space, versatility, and modern updates on 2.74 picturesque acres. This expansive residence features five bedrooms and four-and-a-half baths, including a fully connected in-law suite designed for multi-generational living, extended guests, or

Richard Phillips Northrop 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

NEW PRICE! OPEN HOUSE SUNDAY 5/17 - 10:00-12:00! 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

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

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.

HOME TO BE BUILT - Don't miss the final opportunity to build your custom home! Experience the breathtaking mountain views and modern luxury in this stunning 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

Jennifer Beall Charis Realty Group

Scenic views, top-rated schools, and no HOA—this beautifully updated Quad-level home in sought-after Middletown offers the perfect blend of comfort, efficiency, and lifestyle. Situated on a quiet street and backing to open farmland adjacent Summers Farm, this 4–5 bedroom, 2.5 bath home provides 2,200 square feet of versatile living space. Inside, you’ll find hardwood floors throughout, fresh

kimberly obendorfer RE/MAX Realty Group

THIS COMPLETELY RENOVATED & BEAUTIFULLY RESTORED HOME HAS BEEN UPDATED THROUGH-OUT WITH ALL BRAND NEW ITEMS INCLUDING THE FOLLOWING: Roof & underneath sheathing to ensure a solid foundation for new materials, Electrical updated to code, new Plumbing and components including faucets, toilets, new shower with White Tile, Frigidaire Stainless Steel Appliances including Electric Range/Oven,

Heather Ponce Maryland Elite Realtors

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

Welcome to 213 W Main Street in the heart of historic Middletown! This charming home blends historic character with everyday functionality. Inside, you’ll find original Southern yellow heart pine flooring, 9-foot ceilings on the main level, and beautiful architectural details throughout. The main level features a spacious living room, dining room, kitchen, full bath with shower, and convenient

Steven Petruzzello Century 21 Redwood Realty

Welcome to Foxfields at Middletown, one of the area’s most sought-after 55+ communities. This beautifully maintained Admar-built Radford II offers the ease of main-level living paired with exceptional space for guests, entertaining, and everyday comfort. With 3 bedrooms, 4 full bathrooms, and the potential for a 4th bedroom in the finished lower level, this home is thoughtfully designed for both

Lauren Olson RE/MAX Results

Welcome to this inviting rancher tucked into the heart of Middletown where you can enjoy scenic views and walk for ice cream all in a few steps. This one screams for ice cream. Just kidding. It screams LOCATION, LOCATION, LOCATION! No HOA and under $400K. That should be a headline!Inside, you'll find three bedrooms, three baths and an easy, open layout designed for everyday living. Neutral

Marylou Fisher Century 21 Redwood Realty

Your Private Oasis in Middletown ValleyThe Wait is Over! Welcome to the perfect blend of classic Maryland charm and modern peace of mind. Nestled on a quiet cul-de-sac, this stunning all-brick rancher offers the lifestyle you’ve been searching for in beautiful Middletown.Step through the front door and feel instantly at home. The hardwood floors gleam under the natural light pouring

Isis Tepper Berkshire Hathaway HomeServices PenFed Realty

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.

Charming Victorian Home offers the perfect blend of historic character and modern upgrades in the heart of Middletown. Vehicle access from both Beautiful Main Street and Convenient Broad Street, this home provides excellent accessibility and curb appeal. Beautiful Hard Wood Floors, Wainscoting, Crown Molding throughout. Main Level Features Separate Living Room, Dining Room w/Pocket Doors, Family

John Callan Real Estate Teams, LLC

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

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

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.