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98 Summers Dr, Middletown
$399,999
3 Beds ⋅ 3 Baths
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 paint, LVP flooring and stainless appliances make the upper level shine bright-like a diamond. A newly built breezeway that connects the oversized single car garage is charming and will keep you dry! A cute little backyard to get creative with. Bring the chickens or a play set. It's open space, waiting for you. The lower level is finished and screams movie room and let's hang out! Flex space and plenty of storage. Did I mention Middletown schools? This district is known for its school spirit and community. GO Knights! Views, Updates, space, NO HOA and BRAND NEW HVAC!!! THIS one checks all the boxes. YOU ARE HOME!!

98 Summers Dr, Middletown

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: Real Estate Teams, LLC.

7201 Dogwood Ln, Middletown
$371,000
3 Beds ⋅ 2 Baths
Discover this charming 3-bedroom, 2-bath ranch home on a spacious 0.63-acre lot in the desirable Middletown Valley (Fountaindale North neighborhood). This 1,651 sq ft single-family residence, built in 1957, features beautiful hardwood floors throughout the first floor and offers incredible potential for your personal touches to bring it to life. Enjoy breathtaking mountain sunsets right from your front porch! The peaceful setting provides stunning views while offering the perfect blend of privacy and convenience. Located in the heart of Middletown, you’ll love the benefits of: • Top-rated Middletown schools • Nearby shopping and dining • Easy commuting in every direction — east, west, north, or south Whether you’re looking for a starter home, investment opportunity, or peaceful retreat, this home delivers. Key Features: • 3 bedrooms • 2 full bathrooms • Hardwood floors throughout the first floor • 1-car garage • Generous 0.63-acre lot • Single-level living • Wood-burning fireplaces (2) Don’t miss your chance to own a piece of Middletown Valley! Schedule your showing today and imagine the possibilities.

7201 Dogwood Ln, Middletown

Listing courtesy of Samson Properties. Contact:

Selling Office: Long & Foster Real Estate, Inc..

323 S Jefferson St S, Middletown
$369,000
3 Beds ⋅ 2 Baths
This 3/4 Bedroom home has 2 Full Baths and sits in a country setting. It has been completely remodeled inside and out. New siding, new roof, new windows and landscaping on the outside. The inside has been freshly painted, all new flooring, kitchen has new stainless steel appliances and new cabinets. The eat-in kitchen also has new counter tops, beautiful backsplash and top of the line kitchen sink. The basement family room has built in book shelves and a full bath off of it. The office/ 4th bedroom has built in book shelves as well. There is plenty of storage and the laundry room in the basement too. Large rear yard! Convenient to shopping, schools, travel and historic sites.

323 S Jefferson St S, Middletown

Listing courtesy of Mackintosh , Inc.. Contact:

Selling Office: Kelley Real Estate Professionals.

33 E Main St, Middletown
$360,000
6 Beds ⋅ 4 Baths
Rare Opportunity: Own 2 Units for the Price of 1 in Historic Middletown! Discover this exceptional multi-unit property in the heart of charming, historic Middletown—perfectly positioned for a lifestyle of convenience, character, and potential. Stroll to your favorite restaurants, boutique shopping on vibrant Main Street, and scenic local parks featuring jogging trails, streams, and lush green spaces. Immerse yourself in the rich history and timeless beauty this community has to offer! The main residence is a classic Historic Victorian boasting 3 bedrooms and 1.5 baths, rich with the architectural elegance and original details you’d expect: ornate moldings, grand proportions, and old-world charm. This diamond in the rough offers incredible potential for the visionary buyer or investor—Investor Alert! The primary residence requires renovation and will not qualify for standard financing options (such as FHA 203(b), Conventional, VA, or USDA) due to the lack of operational heat and other needed repairs. Bring your creativity and contractor to restore this beauty to its former glory. Complementing the main home is a spacious detached 3-bedroom, 1-bath apartment with its own entrance, located at the rear of the property. This unit is in excellent, move-in ready condition and includes a 3-car garage—an incredible bonus for parking, storage, or hobbies. Versatile Living Options: Occupy the apartment while renovating the main Victorian at your own pace or possible rental /Airbnb for strong income potential. Ideal for extended family, guests, or generating passive revenue in a highly desirable historic district. This rare package combines historic appeal, modern practicality, and strong investment upside in one of Middletown’s most walkable locations. Don’t miss your chance to own a piece of history with immediate income or living flexibility! Schedule your private showing today—properties like this don’t last long.

33 E Main St, Middletown

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: Keller Williams Realty Centre.

208 Main St, Middletown
$360,000
4 Beds ⋅ 3 Baths
208 W Main Street in Middletown offers the rare combination of historic Main Street charm and major modern updates — including a brand-new structural roof and sheathing for long-term peace of mind. Fully renovated and move-in ready, this thoughtfully updated home blends character, comfort, and convenience in one of Frederick County’s most walkable small-town settings. Step inside to bright, refreshed living spaces featuring updated finishes, modern systems, and a flexible layout designed for everyday living. The desirable main-level primary suite adds convenience and accessibility, while the renovated interior preserves the warmth and personality buyers love in historic homes. A surprise Bonus room is above the kitchen and all new systems include manufacturer's warranty. Outside, enjoy a private backyard ideal for relaxing, entertaining, gardening, or quiet evenings at home. Located just moments from Middletown’s shops, dining, parks, and local events, this property offers a true walkable lifestyle with nearby EV charging access and the freedom of no HOA restrictions. Whether you’re searching for your first home, downsizing into something full of character, or looking for a turnkey historic property without the renovation headaches, this Main Street home delivers a unique opportunity to enjoy small-town living with modern confidence.

208 Main St, Middletown

Listing courtesy of Maryland Elite Realtors. Contact:

Selling Office: Marsh Realty.

25 Boileau Ct, Middletown
$354,000
3 Beds ⋅ 4 Baths
Welcome to 25 Boileau Court in Middletown. This three-level townhome is located in a small neighborhood with no HOA and is conveniently situated near downtown Middletown. The main level features a living room, dining room, kitchen, and half bathroom. The spacious primary suite is located on the upper level and includes an en suite bathroom. Two additional bedrooms and a full hallway bathroom complete the second level. The lower level provides additional living space with a family room that has walkout access to the backyard, along with a half bathroom for added convenience. Recent updates include a roof that is just 2 years old, fresh paint throughout, and new carpet in the lower level. This home has been well maintained, thoughtfully updated, and is truly move-in ready. Plenty of parking available. This property offers easy access to the local shops, dining, parks, and everyday amenities of downtown Middletown. It is so close you may not even need to take your car. Don't miss your chance to see this home. Schedule your tour today!

25 Boileau Ct, Middletown

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: RE/MAX Results.

1629 Dahlgren Rd, Middletown
$322,000
3 Beds ⋅ 1 Baths
Charming brick rancher set on 4.64 acres with stunning views and exceptional potential. This 3-bedroom, 1-bath home offers classic construction and “good bones,” making it a fantastic opportunity for buyers looking to add their own updates or build sweat equity. The home features a functional layout with an unfinished basement that provides additional space for storage, hobbies, or future finishing. This property consists of 2 tax parcels, offering added privacy, flexibility, and potential uses. The property also features a small stall barn, making it especially appealing for hobby farming, animals, or additional storage. Surrounded by trees and scenic countryside, the setting provides peaceful views and a sense of privacy while still being conveniently located near local commuter routes. Outdoor enthusiasts will appreciate the close proximity to Civil War historical sites, nearby battlefields, and the Appalachian Trail. Whether you’re looking for a primary residence, investment opportunity, or a property with room to grow, this home offers a rare combination of location, land, and opportunity.

1629 Dahlgren Rd, Middletown

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Samson Properties.

1936 Old National Pike, Middletown
$310,000
4 Beds ⋅ 2 Baths
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 Middletown, this turn-of-the-century brick home sits on almost four acres along Maryland’s historic Old National Pike. The property offers substantial upside for buyers prepared to take on a full-scale renovation, with large interior spaces, classic brick construction, a metal roof, and mature surrounding acreage. The home, built circa the turn of the last century, is listed strictly "as-is" and is currently not move-in ready. It offers a durable metal roof and generous interior space, but it needs a comprehensive overhaul. The Land & Outbuilding is nearly four acres, feature mature acreage and include a spacious outbuilding/barn structure with existing electric service. This asset can be used as a workshop, studio, storage, or for conversion. Historic Significance: This is a true piece of local history, positioned directly on Maryland’s original National Pike Road. This home is for the buyer dedicated to preservation; it provides the opportunity to bring a landmark property back to its former glory. Conservation Easement: The Maryland Environmental Trust (MET) Conservation Easement covers the property. This is an optimal acquisition for an experienced house flipper or investor looking for a major value-add project with significant potential ROI after full restoration. Ideal for buyers who value privacy, history, and the potential to make this property their own.

1936 Old National Pike, Middletown

Listing courtesy of Mackintosh, Inc.. Contact:

Selling Office: Kelley Real Estate Professionals.

10 Linden Blvd, Middletown
$310,000
3 Beds ⋅ 2 Baths
CHARMING RANCHER IN MIDDLETOWN, MD! Welcome home to this delightful 3-bedroom, 1.5-bath rancher in an excellent location. This well-maintained home features a cozy living room with fireplace, a kitchen, and a full basement with fireplace providing ample space for storage, hobbies, or future expansion. Hardwood floors extend through nearly the entire home! Enjoy the convenience of a paved driveway and an attached 2-car garage, perfect for parking and additional workspace. The spacious backyard offers plenty of room for outdoor entertaining, gardening, or simply relaxing. Located close to local schools, parks, and commuter routes, this home combines small-town charm with everyday practicality. Don’t miss your opportunity to make this charming rancher your new home!

10 Linden Blvd, Middletown

Listing courtesy of Hurley Real Estate & Auctions. Contact:

Selling Office: Kelley Real Estate Professionals.

6419 Zittlestown Rd, Middletown
$240,000
2 Beds ⋅ 1 Baths
NO HOA and NO CITY TAXES! Charming cottage-style home nestled on a scenic .38-acre lot, located on South Mountain near the Washington/Frederick county line, offering peaceful surroundings and timeless appeal. This 2-bedroom, 1-bath home features a welcoming full-length front porch—perfect for relaxing and enjoying the natural setting. Recent updates include durable vinyl siding, added blown-in insulation, and a newer well on the property, improving efficiency and providing peace of mind. The home offers a simple, functional layout with a cozy feel, ideal for a full-time residence, weekend retreat, or investment opportunity. Set on a gently sloping lot with mature trees and open green space, the property provides a private, rural feel while still being conveniently located near Middletown, Boonsboro, and major commuter routes. A great opportunity to own an affordable single-family home with character, updates already completed, and room to make it your own. Schedule your showing today!

6419 Zittlestown Rd, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Charis Realty Group.

417 W Main St, Middletown
$240,000
3 Beds ⋅ 1 Baths
Price Improved and ready for you to make this your new home in 2026 !! Welcome to this delightful 3-bedroom, 1-bath single-family home nestled on Main St. in the heart of historic Middletown. Full of character and timeless appeal, this vintage gem is brimming with potential. Situated on a generous lot, the home boasts a spacious backyard—perfect for outdoor entertaining, gardening, or future expansion. Inside, you'll find original details that speak to the home's heritage, creating a warm and inviting atmosphere that’s ready to be reimagined. Whether you're looking to bring new life to a classic property or create your dream home in a sought-after location, this residence offers the perfect canvas. Attic is fully floored for extra storage, basement is unfinished & is another great storage space. With its unbeatable location in a charming community close to schools, shops, and parks, this is an opportunity you don’t want to miss.

417 W Main St, Middletown

Listing courtesy of RE/MAX Realty Centre, Inc.. Contact:

Selling Office: RE/MAX Realty Group.

9440 Hollow Rd, Middletown
$190,000
3 Beds ⋅ 2 Baths
Attention investors – Flip Opportunity in Middletown! Handyman special with strong value-add potential. This property sits on a generous 0.4-acre lot and includes a barn, a shed and a detached garage that was converted into a studio apartment offering multiple avenues for increased resale value. The home requires a full renovation, making it ideal for experienced investors looking to maximize returns and build equity from the ground up. With the right vision and rehab plan, this property has the potential to be transformed into a highly desirable resale. Located in a flood zone—priced accordingly and reflected in the opportunity. Property is being sold strictly as-is. Bring your contractor and your vision!

9440 Hollow Rd, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Deausen Realty.

Burkittsville Road, Middletown
$35,000
Wow! How often do you see a reasonably priced parcel with close access and water privileges? Ever wish you had a place to recreate close to home? Have you ever wanted to escape from your home and still have a place to go? This could be it!! No HOA, you don't even have to mow it! Just show up and enjoy. The sound of the water going over the weir is so peaceful and relaxing. It diminishes the sound of the road traffic on Hwy 17. There is easy access from the road which provides plenty of parking. There are stairs down to the water which could use a handrail repair. But I'm sure you'll have plenty of time for that this summer while you're there enjoying the stream. Please call the agent, Debbie Hugo, for a personal tour. It doesn't have an address but it's between and across the street from addresses 7102A and 7020 Burkittsville Road.

Burkittsville Road, Middletown

Listing courtesy of Samson Properties. Contact:

Selling Office: Charis Realty Group.

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