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$459,900
4 Beds ⋅ 4 Baths
This well-maintained duplex in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units currently 100% leased, this property provides immediate, reliable income, making it a smart addition to any investment portfolio.

104 Madison Ave, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$359,900
2 Beds ⋅ 3 Baths
Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached one-car garage provides additional parking and storage. Upstairs, both bedrooms feature en-suite baths, including a rear bedroom with a private balcony overlooking the backyard and The Links at Perry Cabin Golf Course. Brand-new carpeting has just been installed throughout the upper level, and the home also features a brand-new water heater. Conveniently located near shopping, dining, waterfront parks, and the many attractions of downtown St. Michaels, this property offers an excellent opportunity to enjoy Eastern Shore living.

9531 Quail Hollow Dr Unit #405, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$795,000
4 Beds ⋅ 4 Baths
This two-story Charleston-style Colonial is located in the desirable Cooke’s Hope Village community and sits on an oversized lot with a fenced side and rear yard. The property includes a spacious entry-level side porch, second-level balcony, lush seasonal gardens, and a private fenced brick courtyard with built-in speakers for music and a retractable awning—perfect for outdoor entertaining. Hardwood flooring runs throughout the home. The main level offers a flexible layout with a bedroom just off the entry and a nearby full bath. The kitchen features double wall ovens and a gas cooktop in the island and opens to comfortable living spaces. The living room includes a gas fireplace, while the family room offers custom built-ins, a Vermont wood stove, and direct access to the courtyard and backyard. Upstairs, the primary suite includes a large bath with soaking tub, stall shower, and double vanity. A second en-suite bedroom currently serves as an office with extensive custom built-in cabinetry and could easily convert back to bedroom use. A mudroom off the attached two-car garage provides access to the side yard and leads to a staircase accessing a finished bonus room above the garage. This flexible space features independent heating and hot water and offers excellent options for guests, workspace, or additional living area. Custom built-ins are also found in the garage, family room, bedroom, and office. Additional improvements include a roof replacement in 2025, upgraded heating system in 2020, and a Rinnai hot water system. The property also features an irrigation system to maintain the beautifully landscaped grounds. Cooke’s Hope residents enjoy walking trails, tennis courts, fitness center, dog park, and well-maintained community green spaces.

28713 Emanuel St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$100,800
Buildable 1/2 +/- acre lot ready for your vision and a builder ready to help you make it a reality! Over 500 ft of shoreline on the Tred Avon River. Close to the public park/playground and just a short boat ride or ferry ride to Oxford. Centrally located between Easton and St Michaels. Just minutes to Talbot County's favorite waterfront towns by car, bike, or boat.

25831 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$499,000
4 Beds ⋅ 4 Baths
Desirable Rio Vista Duplex – Live in One Unit and Rent the Other! Rare opportunity to own a duplex in the sought-after Rio Vista community. Move into one unit and generate rental income from the other to help offset your mortgage payments. Properties like this seldom come on the market. Located in a water-access community, residents may enjoy dock access upon approval of the owner's application and payment of applicable fees. The property features two mirror-image units, each offering: Kitchen with a cozy breakfast area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath This duplex presents an excellent investment opportunity with a strong rental history. Both units are currently tenant-occupied and rent well. Additional opportunity: The neighboring duplex at 1215 is also available for purchase (MLS #MDTA2012950).UST REDUCED - DONT WAIT TO LOOK AT THIS DESIREABLE RIO VISTA LIVING -MOVE

1211 Washington, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283
$455,000
3 Beds ⋅ 3 Baths
Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a bright and open living area with gas fireplace, custom built-ins, and seamless access to a private rear patio overlooking peaceful common space. The stunning kitchen has been completely transformed with quartz countertops, soft-close cabinetry, and newer stainless steel appliances. A main-level bedroom with its own ensuite bath provides flexible living options for guests or primary use. Upstairs, the spacious owner’s suite features a private balcony, a spa-like bath, and generous closet space, along with a second guest suite offering its own private bath. Additional improvements include fresh interior and exterior paint, a newer HVAC system (within the last five years), updated carpeting, refinished hardwood floors, and recently installed 6” gutters. The property includes a one-car garage with attic storage,plus paved parking. Backing to open common area for added privacy and tranquility, and located near The Links at Perry Cabin with no town taxes, this home delivers comfort, convenience, and exceptional value.

9518 Quail Hollow Unit #702, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$774,000
3 Beds ⋅ 3 Baths
Designed to optimize water views of the Tred Avon and access to the community kayak launch and beach area is this to be built home. Centrally located between Easton and St Michaels and just a stone's throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County's premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Additional floor plans, options, and upgrades available. Some photos and renderings are for illustrative purposes only and may include additional upgrades.

25831 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665