17

Homes for Sale in 21658

Section Image Section Image
  • 500 Nesbit Rd, Queenstown, MD 21658
    500 Nesbit Rd, Queenstown, MD 21658
    500 Nesbit Rd, Queenstown, MD 21658
    /53

    $1,249,000

    Open Sat 1PM - 3PM Coming Soon
    • 5 Beds
    • 5 Baths
    • 3,666 Sq Ft

    500 Nesbit Rd, Queenstown, MD 21658

    This is the quintessential Eastern Shore Waterfront Estate to turn into your legacy property. Sitting on over 12 acres just minutes from the Bay Bridge, this substantial craftsman built in 1914 once served as the primary residence for one of the lead engineers for the Pentagon, Jefferson Memorial, and other DC marvels due to its balance of proximity to the city and quality of life. Lifestyle

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    500 Nesbit Rd, Queenstown, MD 21658
  • 377 Hemsley Dr, Queenstown, MD 21658
    377 Hemsley Dr, Queenstown, MD 21658
    377 Hemsley Dr, Queenstown, MD 21658
    /68

    $2,395,000

    • 4 Beds
    • 3.5 Baths
    • 4,504 Sq Ft

    377 Hemsley Dr, Queenstown, MD 21658

    Waterfront living in Queenstown with sought-after southeastern exposure and 7 ft MLW, offering ideal conditions for boating and enjoying life on the water. Set on a beautifully landscaped, high-elevation lot, the property provides both privacy and peace of mind, with mature plantings, manicured grounds, and a paved driveway that creates a welcoming approach. This 4-bedroom, 3.5-bath home spans

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 453-1086

    377 Hemsley Dr, Queenstown, MD 21658
  • 7121 Main St, Queenstown, MD 21658
    7121 Main St, Queenstown, MD 21658
    7121 Main St, Queenstown, MD 21658
    /75

    $629,900

    Open Sun 1PM - 3PM
    • 4 Beds
    • 4 Baths
    • 2,528 Sq Ft

    7121 Main St, Queenstown, MD 21658

    Steeped in history and full of soul, the historic Queenstown School House, known as Double School House Number 6 and built in 1834, feels less like a house and more like a story carefully carried through generations. Expanded, renovated, and thoughtfully updated over the years, it still holds onto the details that make historic homes unforgettable. Original wavy glass window panes catch the

    Micheal Vakas EXP Realty, LLC

    7121 Main St, Queenstown, MD 21658
  • 306 Overlook Dr, Queenstown, MD 21658
    306 Overlook Dr, Queenstown, MD 21658
    306 Overlook Dr, Queenstown, MD 21658
    /24

    $599,000

    $10K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,702 Sq Ft

    306 Overlook Dr, Queenstown, MD 21658

    Back on the market at No Fault of the Sellers. Nestled in a peaceful country setting, this spacious 5-bedroom, 2.5-bath Colonial offers the perfect blend of privacy, comfort, and room to grow. Designed with everyday living in mind, the home features generous living spaces ideal for both relaxing and entertaining.The large kitchen offers plenty of space for cooking and gathering, with an

    Jennifer Angel-Fuhlman Coldwell Banker Realty

    306 Overlook Dr, Queenstown, MD 21658
  • 108 Gloucester Rd, Queenstown, MD 21658
    108 Gloucester Rd, Queenstown, MD 21658
    108 Gloucester Rd, Queenstown, MD 21658
    /60

    $599,999

    $70K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    108 Gloucester Rd, Queenstown, MD 21658

    Reintroduced with a compelling new price ! Take a look you’ll be glad you did.Welcome to this beautifully maintained, custom-built, one-owner home in the highly sought-after Bennett Point area. Thoughtfully updated and meticulously cared for over the years, this property offers a true move-in ready experience with quality improvements throughout. Inside, you’ll find a freshly painted interior

    Mary Jameson Long & Foster Real Estate, Inc.

    108 Gloucester Rd, Queenstown, MD 21658
  • 200 Wye Rd, Queenstown, MD 21658
    200 Wye Rd, Queenstown, MD 21658
    200 Wye Rd, Queenstown, MD 21658
    /68

    $4,700,000

    • 6 Beds
    • 5.5 Baths
    • 8,180 Sq Ft

    200 Wye Rd, Queenstown, MD 21658

    Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable

    Brad Kappel TTR Sotheby's International Realty

    200 Wye Rd, Queenstown, MD 21658
  • 319 Wye Rd, Queenstown, MD 21658
    319 Wye Rd, Queenstown, MD 21658
    319 Wye Rd, Queenstown, MD 21658
    /29

    $655,000

    Open Sun 2PM - 4PM
    • 3 Beds
    • 2.5 Baths
    • 2,064 Sq Ft

    319 Wye Rd, Queenstown, MD 21658

    Set on more than 5 tranquil acres with woods, open space, and a partially fenced yard, this inviting one-level home offers a peaceful setting along the Wye River with glimpses of the water. Enjoy morning coffee or evening cocktails from the welcoming front porch while taking in the serene surroundings. Inside, the thoughtfully designed floor plan features an open kitchen with granite countertops,

    Dee Dee McCracken Coldwell Banker Realty

    319 Wye Rd, Queenstown, MD 21658
  • 121 Kilby Point, Queenstown, MD 21658
    121 Kilby Point, Queenstown, MD 21658
    121 Kilby Point, Queenstown, MD 21658
    /106

    $3,040,000

    $160K PRICE DROP
    • 4 Beds
    • 7 Baths
    • 4,903 Sq Ft

    121 Kilby Point, Queenstown, MD 21658

    This is a true coastal retreat, from its stunning exterior to its thoughtfully designed living spaces. A one-of-a-kind waterfront estate, the property offers more than 2,000 feet of shoreline and sits on 5.4 private acres at the end of Kilby Point. Surrounded by water on both the Wye River and Eastern Bay, this exceptional home captures endless panoramic views in every direction. And yes—how many

    Dee Dee McCracken Coldwell Banker Realty

    121 Kilby Point, Queenstown, MD 21658
  • 351 Wye Rd, Queenstown, MD 21658
    351 Wye Rd, Queenstown, MD 21658
    351 Wye Rd, Queenstown, MD 21658
    /92

    $2,250,000

    Open Sun 11AM - 1PM $250K PRICE DROP
    • 6 Beds
    • 5 Baths
    • 6,340 Sq Ft

    351 Wye Rd, Queenstown, MD 21658

    If you love the water, this extraordinary Wye River property is a dream setting. Situated on the point with more than 1,400 feet of waterfront, this property is fully equipped for waterfront living with two piers, a private beach, and a boat launch.The custom 6,400-square-foot home offers exceptional space and comfort, featuring a brick front, four-car garage, double porches, and walkout

    Dee Dee McCracken Coldwell Banker Realty

    351 Wye Rd, Queenstown, MD 21658
  • 252 Harbor Ln, Queenstown, MD 21658
    252 Harbor Ln, Queenstown, MD 21658
    252 Harbor Ln, Queenstown, MD 21658
    /108

    $795,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,651 Sq Ft

    252 Harbor Ln, Queenstown, MD 21658

    Welcome to a VERY well-maintained 4 bedroom, 2.5 bathroom home located in the coveted Queenstown Harbor waterfront community. This beautiful waterfront home features a main-level primary suite with hardwood floors and a private en-suite bath, plus 3 additional bedrooms on the upper level. The Gourmet chef's kitchen is equipped with stainless steel appliances, marble countertops, and opens to

    Donna Dickinson Coldwell Banker Realty

    252 Harbor Ln, Queenstown, MD 21658
  • 107 Chestnut Ln, Queenstown, MD 21658
    107 Chestnut Ln, Queenstown, MD 21658
    107 Chestnut Ln, Queenstown, MD 21658
    /50

    $625,000

    $14K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,785 Sq Ft

    107 Chestnut Ln, Queenstown, MD 21658

    Queenstown - This 4 bedrooms, 2.5 bath home is located between Route 50 and Route 301, so great access to either. Nice country setting with no HOA. Bright and open kitchen/family room with also formal living room and dining room. Spacious bedrooms and a bonus room over the garage. You will enjoy the wrap around porch and country living, but still close to everything.

    Linda Austin Long & Foster Real Estate, Inc.

    107 Chestnut Ln, Queenstown, MD 21658
  • 248 Harbor Ln, Queenstown, MD 21658
    248 Harbor Ln, Queenstown, MD 21658
    248 Harbor Ln, Queenstown, MD 21658
    /19

    $290,000

    • Land
    • 12,632 Sq Ft
    • $1,000,000 per Acre

    248 Harbor Ln, Queenstown, MD 21658

    Queenstown Harbor - The last building lot available is now on the market. This property offers public water and sewer. The property is .29 acre with waterviews. The community offers private pier and landing. This is the property you have been looking for, on the inlet of Queenstown Creek, but not taxed as waterfront. The community holds the buffer on the waterfront.

    Linda Austin Long & Foster Real Estate, Inc.

    248 Harbor Ln, Queenstown, MD 21658
  • 325 Greenspring Rd, Queenstown, MD 21658
    325 Greenspring Rd, Queenstown, MD 21658
    325 Greenspring Rd, Queenstown, MD 21658
    /32

    $549,990

    New Construction $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    325 Greenspring Rd, Queenstown, MD 21658

    PRICE REDUCED- BRING ALL BUYERS A fantastic opportunity for buyers looking for exceptional value in a move-in ready home. The seller is very motivated! Property is just 10 minutes from the Bay Bridge IN QUEENSTOWN AND NO HOA!!! , This brand new custom rancher offers the perfect blend of country living and convenience. Surrounded by a peaceful rural setting ideal for deer and fowl hunters, this

    Charles Cockrill Berkshire Hathaway HomeServices PenFed Realty

    325 Greenspring Rd, Queenstown, MD 21658
  • 915 Sportsman Neck Rd, Queenstown, MD 21658
    915 Sportsman Neck Rd, Queenstown, MD 21658
    915 Sportsman Neck Rd, Queenstown, MD 21658
    /33

    $375,000

    $25K PRICE DROP
    • Land
    • 2 Acres
    • $187,500 per Acre

    915 Sportsman Neck Rd, Queenstown, MD 21658

    Two peaceful acres nestled in Hickory Ridge Community at the very end of Sportsman Neck Rd. Perc approved. Backs to woods/ravine. Water views of the Wye River! Level and clear with mature trees. Very rare opportunity to own a property in a well established quiet community close to the water. Close to Rt 50 for easy access to the Bay Bridge or Easton. Don't miss out! Appointment required.

    Jason Dey Kevin Dey Realty

    915 Sportsman Neck Rd, Queenstown, MD 21658
  • 100 Wall St, Queenstown, MD 21658
    100 Wall St, Queenstown, MD 21658
    100 Wall St, Queenstown, MD 21658
    /46

    $444,900

    • 6 Beds
    • 2 Baths
    • 2,486 Sq Ft

    100 Wall St, Queenstown, MD 21658

    Seller has found a property out of state, so all reasonable offers will be considered...Step back in time—without sacrificing a single modern comfort—in this colonial masterpiece, where historic elegance and thoughtful renovations come together in perfect harmony. Nestled in the picturesque and walkable heart of Queenstown, this 6-bedroom, 2-bath showstopper is more than just a home—it's an

    Darlene Winegardner RE/MAX Executive

    100 Wall St, Queenstown, MD 21658
  • 6107 Ocean Gateway, Queenstown, MD 21658
    6107 Ocean Gateway, Queenstown, MD 21658
    6107 Ocean Gateway, Queenstown, MD 21658
    /6

    $52,500

    $45K PRICE DROP
    • Land
    • 39,204 Sq Ft
    • $58,333 per Acre

    6107 Ocean Gateway, Queenstown, MD 21658

    Great exposure to Rt 50. Working with county on potential uses.

    Jimmy Higgins Benson & Mangold, LLC

    6107 Ocean Gateway, Queenstown, MD 21658
  • 0 U S 301, Queenstown, MD
    0 U S 301, Queenstown, MD
    0 U S 301, Queenstown, MD
    /5

    $199,900

    $50K PRICE DROP
    • Land
    • 1.11 Acres
    • $180,090 per Acre

    0 U S 301, Queenstown, MD

    1 acre parcel located within the Queenstown town limits. Zoned highway commercial. 4 water/sewer allocations included. Call office for list of permitted uses. 662 feet of highway frontage (Rt 301). Near Royal Farms. Access from Melvin Ave. Sign on property.

    Jason Dey Kevin Dey Realty

    0 U S 301, Queenstown, MD
Maryland Queen Anne's County Queenstown 21658

Real Estate & Homes for Sale in 21658

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group