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$375,000
Welcome to this charming Victorian duplex on South Street, offering character and investment potential. Opportunities like this are rare! Whether you're looking to owner-occupy while generating rental income or expand your investment portfolio, this property offers exceptional flexibility. Each unit features 3 bedrooms, 1 full bath, each has their own private entrance, providing privacy and convenience for both occupants. The upper unit includes a spacious walk-up attic, offering additional storage or future potential. Outside, you'll find a large fenced backyard, a welcoming wraparound front porch, and a detached garage that can be used for storage, a workshop, or additional income opportunities. Major updates have already been completed, including both heaters/water heater replaced in 2019 and a new roof installed in 2023. The first-floor unit is currently leased through March 2027, with rent paid in full, providing immediate, reliable income. Live in the upper unit while collecting rental income from the lower unit, or continue renting both units as a strong investment property. With its prime location, historic charm, and excellent income potential, this is an opportunity you won't want to miss.

133 W South St, Smyrna

Listing courtesy of Crown Homes Real Estate. Contact: (302) 504-6147

$199,000
4 Beds 2 Baths
Welcome to a wonderful opportunity to own a home in the heart of Dover! This property offers spacious living with a functional floor plan, spacious living areas, and plenty of natural light throughout. The home features generously sized bedrooms, a kitchen with ample cabinet and counter space, and comfortable living and dining areas perfect for everyday living or entertaining. Step outside to enjoy the backyard, offering space for outdoor gatherings, gardening, or simply relaxing. Conveniently located near downtown Dover, Delaware State University, Bayhealth Hospital, Dover Air Force Base, and major commuter routes including Route 1, this home provides easy access to everything the area has to offer. Whether you're a first-time homebuyer, looking to downsize, or searching for an investment opportunity, this property is full of potential. Schedule your private showing today and see all that 219 N Governors Ave has to offer!

219 N Governors Ave, Dover

Listing courtesy of RE/MAX Associates-Wilmington. Contact: 3024773900

$525,000
4 Beds 3 Baths
Nestled in the prestigious Wild Quail Golf & Country Club community, this charming Victorian home offers a perfect blend of comfort and elegance. This property provides a Tranquil Retreat while still being conveniently located to all Dover offers. This home showcases a delightful mix of Victorian and Colonial architectural styles, enhanced by accents like a two-story Turret. Step inside this custom built home to discover a spacious foyer with staircase and wood floors. Across the foyer, the dining room shines with natural light from numerous windows, The heart of the home is the inviting kitchen, featuring gourmet amenities such as a cooktop, wall oven, and a generously sized island, perfect for culinary enthusiasts. The kitchen flows seamlessly into the formal living room, with abundant natural light and a fireplace mantle with attractive built ins, creating an ideal space for gatherings and everyday living. Ascend the stairs, to discover the Expansive Primary Suite, where the Turret design continues, creating a luminous ambiance. This brightly lit suite features a generous walk-in closet and an en suite bathroom. Three more bedrooms, two of which have French doors, and a laundry round out the space nicely. The partially finished lowest level offers plenty of flexible space. The private backyard is ideal for enjoying nature with farm and wooded views. Experience the perfect blend of comfort, style, and nature in this exceptional property. Home offered As-Is. Perfectly situated on a traffic free cul de sac. See Where this Residence takes you!!

4 Drake Ct, Camden Wyoming

Listing courtesy of Walt Simpson Realty. Contact: 3022425146

$1,200,000
Turnkey 9-unit multifamily investment in Dover, surrounded by historic character and ongoing area revitalization. Stabilized asset producing approximately $11,700 per month (4-1-26) in rental income, plus additional income from on-site central washer and dryer facilities. Tenants pay their own gas heat and electric. Owner pays water, sewer, trash, and central hot water. Property has seen numerous recent improvements including updated windows, interior upgrades, select new kitchens, and recently installed flooring in most units. Hallways have been refreshed with new flooring and paint. Capital improvements include a new fire escape and some newer heating systems. Strong in-place income with additional ancillary revenue and continued upside through future unit improvements and long-term rental demand in the Dover market. Ideal for investors seeking a stabilized asset with proven cash flow.

26 S State St, Dover

Listing courtesy of RE/MAX Horizons. Contact: (302) 678-4300

$419,999
4 Beds 3 Baths
Step into a beautifully restored Victorian where timeless charm meets thoughtful modern living, set in the heart of the quaint town of Clayton. Completely renovated from the studs out, this 4-bedroom, 3-full-bath home honors its historic character while offering the comfort and ease of a brand-new home, with all-new electrical, plumbing, and drywall throughout. Sunlight drifts through gracious rooms filled with classic architectural details, creating a sense of warmth and calm at every turn. The kitchen blends elegance and function with new cabinetry, granite countertops, and stainless-steel appliances—an inviting space for both quiet mornings and lively gatherings. Three full bathrooms provide a spa-like retreat, two featuring beautiful walk-in showers. The first-floor primary bedroom offers peaceful, easy living, while the second floor reveals a second primary suite alongside two welcoming guest rooms. Above it all, the third-floor loft and finished bonus space feel like a private escape—perfect for a home office, creative studio, or cozy reading nook. Outside, life slows on the classic covered front porch, where mornings begin with coffee and evenings end in conversation. In the rear, a poured concrete patio creates a tranquil space to relax, entertain, and enjoy the simple beauty of home. (Photos have AI furniture in some rooms to show the potential)

410 West St, Clayton

Listing courtesy of RE/MAX Eagle Realty. Contact: 3026591320

$1,245,500
5 Beds 5 Baths
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.

105 High St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact: