Middletown Real Estate

$649,000

Rare commercial opportunity in the heart of Middletown, ideally located directly across the street from the famous Wayside Theater and just minutes from I-81 with excellent accessibility and visibility. Zoned B-1 Commercial, this versatile property offers endless possibilities for business owners, investors, or developers seeking a unique space with flexible use options. Take advantage of the opportunity to live in or rent the attached apartment while running your business from the main portion of the home. See the attached document that outlines potential uses. The property features a beautifully maintained 1920s building full of character, including an inviting front porch, welcoming foyer, grand staircase, hardwood floors, exposed brick, and multiple decorative fireplaces that create a distinctive setting for a variety of commercial uses. The updated kitchen, numerous private rooms, and multiple bathrooms provide a functional layout well suited for professional offices, boutique retail, medical or wellness practices, hospitality, event space, or other approved commercial ventures. A significant advantage is the attached second unit, complete with its own kitchen, living area, two bedrooms, and two-and-a-half baths, offering exceptional flexibility for additional office space, employee accommodations where permitted, rental income, or complementary business operations. The configuration also allows the spaces to function independently or be integrated into one larger commercial operation. Situated on an expansive lot, the property includes a detached two-car garage with additional storage, a storage shed, abundant off-street parking, and ample outdoor space to accommodate a variety of business needs. Combining historic charm, modern updates, and valuable commercial zoning, this is a rare opportunity to establish or expand your business in a prime Middletown location with outstanding long-term investment potential.

7760 Main St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$649,000

Exceptional investment opportunity in the heart of Middletown, directly across from the famous Wayside Theater, and conveniently located just minutes from I-81. This unique property features two attached living units, offering outstanding income potential, multigenerational living, or the flexibility to occupy one unit while generating rental income from the other. The main residence showcases the timeless charm of a 1920s home with an inviting front porch, welcoming foyer, beautiful staircase, wood floors, exposed brick, and multiple decorative fireplaces. The updated kitchen features modern cabinetry and a center island. The main unit includes two main-level bedrooms with private en-suite baths, while the upper level offers a spacious primary suite with a walk-in closet and attached bath, plus two additional bedrooms that share a hall bath. The attached second unit is fully equipped with its own kitchen, living room, two bedrooms, and two-and-a-half baths, making it ideal for long-term tenants, short-term rental opportunities (subject to local regulations), or extended family. The property's layout also provides the option to combine both units into one expansive residence if desired. Situated on a generous lot, the property includes a detached two-car garage with additional storage, a storage shed, ample off-street parking, and plenty of outdoor space. Whether you're an investor seeking strong rental potential or a buyer looking for a property with flexible living and income opportunities, this one-of-a-kind multifamily property offers exceptional value in a prime location.

7760 Main St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$1,349,900

4 Beds ⋅ 4 Baths

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 3.78 beautiful acres, 7452 Heritage Oak Terr (Lot 4W) is a gorgeous build-ready homesite with perc approval and well installed. Advertised is the ACL4 plan which features over 4,400 finished sqft, 4 bedrooms and 3.5 baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, formal dining room, morning room, private office, a stately Owner's suite w/260 sqft walk-in closet, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

7453 Heritage Oak Ter, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010

$649,000

7 Beds ⋅ 7 Baths

Single family or multi-family with an approved, attached apartment - directly across from the famous Wayside Theater! This is a rare opportunity to own prime real estate in Middletown on a beautiful, large lot. Nestled in the heart of Middletown and just minutes from I-81, this exceptional 1920s home blends timeless character with modern updates. From the inviting front porch to the welcoming foyer with its stunning staircase, you'll immediately appreciate the home's classic charm. Beautiful wood floors, exposed brick, and multiple decorative fireplaces add warmth and character throughout. The updated kitchen features modern cabinetry, a center island, and ample space for gathering. Two main-level bedrooms each offer private en-suite baths, providing flexible living arrangements. Upstairs, the spacious primary suite includes a walk-in closet and attached bath, along with two additional bedrooms that share a hall bath. A unique highlight of this property is the attached second living unit located at the rear of the home. Complete with two bedrooms, two-and-a-half baths, a full kitchen, and living room, this space offers endless possibilities. It can serve as an in-law suite, guest quarters, or be seamlessly incorporated into the main residence to significantly expand the home's living space. The property also includes a detached two-car garage with additional storage, a storage shed, abundant parking, and plenty of outdoor space to enjoy. This one-of-a-kind property offers historic charm, flexible living options, and an unbeatable location.

7760 Main St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$585,000

Exceptional commercially zoned property in the heart of Middletown, offering outstanding visibility and accessibility on a quiet one-way street just off Main Street and only minutes from I-81. Situated on a beautiful 1-acre lot, this unique property presents endless possibilities for a variety of professional, retail, office, or mixed-use applications. The flexible floor plan provides ample space to customize for your business needs, with multiple large rooms that can easily accommodate private offices, conference areas, client meeting spaces, or collaborative work environments. A convenient half bath on the main level serves customers and staff, while the upper level features additional rooms and two full bathrooms, making the property well-suited for expanded office space, live/work potential or other commercial uses. Inside, the property showcases timeless architectural details that create a distinctive and welcoming atmosphere. Beautiful hardwood floors, impressive thick moldings, custom built-ins, decorative fireplaces, and a grand entrance foyer with a stunning spiral staircase combine historic charm with professional appeal, helping your business make a lasting impression. With abundant space, flexible configuration, exceptional character, and a highly desirable location close to major transportation routes, this is a rare opportunity to establish or expand your business in one of Middletown's most convenient and recognizable locations.

2239 6th St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$585,000

4 Beds ⋅ 3 Baths

Welcome to this stunning Circa 1872 farmhouse nestled in the heart of Middletown with a stunning view! Situated on a gorgeous 1-acre lot on a quiet one-way street just off Main Street, this spacious property offers the perfect blend of peaceful living and everyday convenience, with easy access to I-81. Zoned B1, it offers many possibilities for either residential or commercial use, including a Bed and Breakfast! (see attached document). Step inside to discover timeless character and charm, featuring gorgeous period details including thick moldings, custom built-ins, decorative fireplaces, and beautiful hardwood floors. The impressive entrance foyer, featuring a grand spiral staircase, welcomes you and creates a memorable first impression. This home is absolutely perfect for entertaining, also featuring a grand dining room and details throughout that only a home of this era can offer. The thoughtfully designed second level offers four spacious bedrooms and two full bathrooms, providing privacy for family and guests. A convenient half bath on the main level is ideal for entertaining. Complete your journey to the third story overlook and enjoy the most beautiful sunsets you can imagine in the Shenandoah Valley - read, paint, meditate, or just relax and enjoy this very unique space. This exceptional home is ready to welcome its next owner.

2239 Sixth St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$399,900

3 Beds ⋅ 2 Baths

If you're looking for an updated home with just under 1 acre of land with plenty of privacy.... look no further! Come see the updated ranch home, one floor living, new kitchen, new bathrooms new flooring and so much more. Home has 3 bedrooms, 2 full bathrooms, oversized two car garage and almost 1 acre of land. Still plenty of time to enjoy your summer nights on the deck. Home is located in quiet, wooded area but still has great access to rt 283 and pa turnpike. Come see for yourself!!!

1384 Roundtop Rd, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: (717) 735-8400

$379,000

An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for generations and is ready for its next chapter. Just a short walk to local shops, restaurants, cafes, and community gathering spaces, this property offers the charm and convenience of small town living. Situated on a generous in town parcel with desirable B1 zoning, the property provides exceptional flexibility for residential living, professional office, business use, or a mixed use concept subject to local approvals. The additional side land offers potential subdivision opportunities subject to application and approval. Rear alley access further enhances the versatility of this unique property while the prominent Main Street location provides outstanding visibility for a variety of future uses. Inside, the home features four bedrooms, two full baths, and the character expected of a historic residence. The property is ready for restoration and thoughtful updating, presenting an exceptional opportunity to preserve its historic charm while incorporating modern improvements. Whether your vision is a distinctive residence, professional office, investment property, or live and work opportunity, the possibilities are substantial. Historic Main Street properties offering this combination of character, location, flexible B1 zoning, additional land, rear alley access, and future potential rarely become available. Property is being sold as is.

7927 Main St, Middletown

Listing courtesy of Coldwell Banker Premier. Contact:

$379,000

4 Beds ⋅ 2 Baths

An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for generations and is ready for its next chapter. Just a short walk to local shops, restaurants, cafes, and community gathering spaces, this property offers the charm and convenience of small town living. Situated on a generous in town parcel with desirable B1 zoning, the property provides exceptional flexibility for residential living, professional office, business use, or a mixed use concept subject to local approvals. The additional side land offers potential subdivision opportunities subject to application and approval. Rear alley access further enhances the versatility of this unique property while the prominent Main Street location provides outstanding visibility for a variety of future uses. Inside, the home features four bedrooms, two full baths, and the character expected of a historic residence. The property is ready for restoration and thoughtful updating, presenting an exceptional opportunity to preserve its historic charm while incorporating modern improvements. Whether your vision is a distinctive residence, professional office, investment property, or live and work opportunity, the possibilities are substantial. Historic Main Street properties offering this combination of character, location, flexible B1 zoning, additional land, rear alley access, and future potential rarely become available. Property is being sold as is.

7927 Main St, Middletown

Listing courtesy of Coldwell Banker Premier. Contact:

$621,619

2 Beds ⋅ 2 Baths

2817 Bernstein Cir, Middletown

Listing courtesy of Blenheim Marketing LLC. Contact: 3022540100

$429,500

Rarely does a property offer this much versatility, whether you're a multigenerational family, an investor, or simply someone who wants room to spread out, 105 Oak Hill Drive delivers two fully functional homes on one spacious corner lot. The main residence is a classic Cape Cod brimming with character and move-in ready condition. Featuring 3 bedrooms, 1.5 baths, it includes a large upstairs den that works beautifully as a bedroom or home office, the layout is both flexible and functional. Enjoy a welcoming living room, a separate dining area, and an eat-in kitchen. The crown jewel of this property is the fully renovated detached ranch-style home, now featuring a brand-new mini-split HVAC system, updated throughout, and completely move-in ready. With its own bedroom and bathroom, this second dwelling is perfect as an in-law suite, a private residence, or a rental unit generating immediate income. It also offers a spacious bathroom with a walk-in shower. Additional highlights include new appliances, a large two-car detached garage with a loft, and a rear storage/workshop — all set on a generous corner lot with mature trees and lush yard space. The possibilities here are truly unique: live in the main house and rent the ranch for passive income, house multiple generations under one address while maintaining privacy, or use the entire property as a compound. All of this in an established Middletown neighborhood close to schools, shopping, and major commuter routes. This is not just a home, it's an investment in flexibility, family, and lifestyle.

105 Oak Hill Dr, Middletown

Listing courtesy of Straub & Associates Real Estate. Contact: (717) 612-9901

$429,500

4 Beds ⋅ 3 Baths

Rarely does a property offer this much versatility, whether you're a multigenerational family, an investor, or simply someone who wants room to spread out, 105 Oak Hill Drive delivers two fully functional homes on one spacious corner lot. The main residence is a classic Cape Cod brimming with character and move-in ready condition. Featuring 3 bedrooms, 1.5 baths, it includes a large upstairs den that works beautifully as a bedroom or home office, the layout is both flexible and functional. Enjoy a welcoming living room, a separate dining area, and an eat-in kitchen. The crown jewel of this property is the fully renovated detached ranch-style home, now featuring a brand-new mini-split HVAC system, updated throughout, and completely move-in ready. With its own bedroom and bathroom, this second dwelling is perfect as an in-law suite, a private residence, or a rental unit generating immediate income. It also offers a spacious bathroom with a walk-in shower. Additional highlights include new appliances, a large two-car detached garage with a loft, and a rear storage/workshop — all set on a generous corner lot with mature trees and lush yard space. The possibilities here are truly unique: live in the main house and rent the ranch for passive income, house multiple generations under one address while maintaining privacy, or use the entire property as a compound. All of this in an established Middletown neighborhood close to schools, shopping, and major commuter routes. This is not just a home, it's an investment in flexibility, family, and lifestyle.

105 Oak Hill Dr, Middletown

Listing courtesy of Straub & Associates Real Estate. Contact: (717) 612-9901

Middletown Real Estate

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