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$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
$465,999
4 Beds ⋅ 3 Baths
​Welcome to this move-in ready Cedar model in the Villages at Middletown—where modern design meets everyday convenience. Offering 4 bedrooms, 2.5 bathrooms, and approximately 1,900 square feet, this home delivers stylish living with an open-concept layout ideal for today’s lifestyle. The main level impresses with a sleek kitchen featuring upgraded mocha cabinetry, stainless steel appliances, and a seamless flow into the living and dining areas—perfect for both relaxing and entertaining. A versatile flex space provides options for a home office, study, or creative use. Upstairs, the spacious primary suite serves as a private retreat, complete with an oversized walk-in closet and a well-appointed ensuite bath with double vanity and a large shower. Three additional bedrooms, including two with walk-in closets, offer flexibility for a variety of needs. The conveniently located upper-level laundry room adds everyday ease. Enjoy the outdoor setting with a backyard that backs to scenic green space, providing a peaceful backdrop. The walk-out basement offers endless potential for customization—ideal for expanding your living space. A perfect blend of style, space, and opportunity—schedule your tour today.

145 Dursley Cir, Middletown

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

$269,900
3 Beds ⋅ 2 Baths
"Investers Alert" - This property has been damaged by fire and needs entire Interior renovation including HVAC, Electrical, Drywall, Fixtures, Etc. Priced Accordingly. Buyer has approved plan for extension details can be provided upon request.This home is ready for whole renovation ,buyer can design and upgrade according to their desire.Property contains a direct access garage, enjoy outdoor gatherings on the beautifully landscaped lot with a private backyard—perfect for summer barbecues or peaceful evenings. Located minutes from Route 1, shopping centers, restaurants, and parks, this home combines suburban tranquility with convenient access to everything Middletown has to offer. Seller will accept higher and best offer (if acceptable to seller) as this conditions CASH offers only, no inspections or contigency. Don’t miss this chance to invest in one of Delaware’s most desirable markets!

945 Lansdowne Rd, Middletown

Listing courtesy of Real Broker, LLC. Contact: 3025567215