13

Homes for Sale in 21658

Section Image Section Image
  • 3207 Bennett Point Rd, Queenstown, MD 21658
    3207 Bennett Point Rd, Queenstown, MD 21658
    3207 Bennett Point Rd, Queenstown, MD 21658
    /69

    $3,495,000

    • 5 Beds
    • 6.5 Baths
    • 7,065 Sq Ft

    3207 Bennett Point Rd, Queenstown, MD 21658

    Welcome to 3207 Bennett Point, a breathtaking Norman Jaffe–designed waterfront estate set on over 5 private acres along the widest stretch of the Wye River. Designed to maximize its setting, the home offers floor-to-ceiling glass, seamless indoor-outdoor living, and panoramic water views from nearly every room.The main residence showcases timeless craftsmanship with Tennessee Quarry

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 936-5560

    3207 Bennett Point Rd, Queenstown, MD 21658
  • 2006 Bennett Point Rd, Queenstown, MD 21658
    2006 Bennett Point Rd, Queenstown, MD 21658
    2006 Bennett Point Rd, Queenstown, MD 21658
    /58

    $1,500,000

    • 4 Beds
    • 3 Baths
    • 2,721 Sq Ft

    2006 Bennett Point Rd, Queenstown, MD 21658

    Spectacular Waterfront Retreat on almost 7 Acres in Exclusive Bennett Point! Welcome to your private paradise on the shores of serene Greenwood Creek! This extraordinary waterfront estate offers almost 7 acres of pure tranquility and luxury, surrounded by water on two sides for a true feeling of seclusion and peace. Your deep-water private pier is a boater’s dream — complete with 3 boat lifts and

    Darlene Winegardner RE/MAX Executive

    2006 Bennett Point 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

    $399,900

    • Land
    • 2 Acres
    • $199,950 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

    $450,000

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

    100 Wall St, Queenstown, MD 21658

    OPEN HOUSE, Saturday, Nov. 15, 2-3pm...Step back in time—without sacrificing a single modern comfort—in this stunning 1856 Victorian 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 opportunity. Zoned Town Center, this

    Darlene Winegardner RE/MAX Executive

    100 Wall St, Queenstown, MD 21658
  • 112 Scottown Rd, Queenstown, MD 21658
    112 Scottown Rd, Queenstown, MD 21658
    112 Scottown Rd, Queenstown, MD 21658
    /25

    $220,000

    • 4 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    112 Scottown Rd, Queenstown, MD 21658

    Opportunity knocks at 112 Scottown Road, offered at $220,000. Ideal for buyers looking to personalize a home or explore investment possibilities. Situated on a level 1⁄2‐acre lot, this property provides room to enjoy the outdoors and features a rear deck ideal for relaxing or entertaining. Single family ranch style property includes an addition suitable for use as an in‐law suite, providing

    Brenda Sarver Maryland Realty Connection

    112 Scottown Rd, Queenstown, MD 21658
  • 0 U S 301, Queenstown, MD
    0 U S 301, Queenstown, MD
    0 U S 301, Queenstown, MD
    /5

    $199,900

    • 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
  • 124 Overlook Dr, Queenstown, MD 21658
    124 Overlook Dr, Queenstown, MD 21658
    124 Overlook Dr, Queenstown, MD 21658
    /54

    $590,000

    • 3 Beds
    • 2.5 Baths
    • 2,654 Sq Ft

    124 Overlook Dr, Queenstown, MD 21658

    PRICE IMPROVEMENT-Welcome to 124 Overlook Drive nestled in the Overlook at Carmichael Community on a quiet non-thru street. This well-maintained Colonial-style spanning over 2,454 square feet is designed to cater to both relaxation and entertainment. Featuring an open floor plan with 3 Spacious Bedrooms and 2 and a Half Bathrooms. Step Inside to a Formal Living Room and Dining Room with newer

    Lauren Smith Keller Williams Flagship

    124 Overlook Dr, Queenstown, MD 21658
  • 325 Greenspring Rd, Queenstown, MD 21658
    325 Greenspring Rd, Queenstown, MD 21658
    325 Greenspring Rd, Queenstown, MD 21658
    /35

    $629,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    325 Greenspring Rd, Queenstown, MD 21658

    Just 10 minutes from the Bay Bridge, 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 location also puts you close to prime outlet shopping, popular seafood restaurants, and a true boater’s paradise. Step inside to an open and modern floor plan featuring 3 bedrooms, 2 full

    Charles Cockrill Berkshire Hathaway HomeServices PenFed Realty

    325 Greenspring Rd, Queenstown, MD 21658
  • 161 Greenwood Creek Rd, Queenstown, MD 21658
    161 Greenwood Creek Rd, Queenstown, MD 21658
    161 Greenwood Creek Rd, Queenstown, MD 21658
    /41

    $649,000

    • 4 Beds
    • 2.5 Baths
    • 2,262 Sq Ft

    161 Greenwood Creek Rd, Queenstown, MD 21658

    WATERVIEWS in QUEENSTOWN! Welcome to this Classic two-story Brick Colonial set on two expansive lots totaling approximately 2.26 Acres, offering Privacy, Space and a sought-after Eastern Shore Lifestyle! This 4BR, 2.5BA well-proportioned home has 2262 square feet of comfortable living space, complemented by Water Views and serene surroundings. Inside, you’ll find timeless charm with Hardwood

    Pamela Ackermann-Doll RE/MAX Executive

    161 Greenwood Creek Rd, Queenstown, MD 21658
  • 137 Rustic Acres Ln, Queenstown, MD 21658
    137 Rustic Acres Ln, Queenstown, MD 21658
    137 Rustic Acres Ln, Queenstown, MD 21658
    /10

    $135,000

    • Land
    • 0.54 Acre
    • $250,000 per Acre

    137 Rustic Acres Ln, Queenstown, MD 21658

    Approved for new home construction!! Buildable .54 acre lot with septic approval. Great location. Easy access to Rt 50 and 213. Buyer is responsible for completing due diligence during the study period.

    Martin Farmer Cummings & Co. Realtors

    137 Rustic Acres Ln, Queenstown, MD 21658
  • 1150 Cheston Ln, Queenstown, MD 21658
    1150 Cheston Ln, Queenstown, MD 21658
    1150 Cheston Ln, Queenstown, MD 21658
    /98

    $2,700,000

    • 4 Beds
    • 2.5 Baths
    • 5,023 Sq Ft

    1150 Cheston Ln, Queenstown, MD 21658

    This amazing property is like no other. Private w/ deep water. The winding private driveway leads to tennis court & 2-story tennis house w/ it's own driveway or stay on the main driveway to the main house. The main part of the main house was built w/ materials from a 1730 barn. Incredible beams, floor, doorways & more! 3 story great room w/ full stone chimney w/ gas fireplace. This dwelling

    Barbara Best RE/MAX One

    1150 Cheston Ln, Queenstown, MD 21658
  • 248 Harbor Ln, Queenstown, MD 21658
    248 Harbor Ln, Queenstown, MD 21658
    248 Harbor Ln, Queenstown, MD 21658
    /18

    $290,000

    • Land
    • 0.29 Acre
    • $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
  • 2107 Bennett Point Rd, Queenstown, MD 21658
    2107 Bennett Point Rd, Queenstown, MD 21658
    2107 Bennett Point Rd, Queenstown, MD 21658
    /38

    $689,000

    • 4 Beds
    • 2.5 Baths
    • 3,264 Sq Ft

    2107 Bennett Point Rd, Queenstown, MD 21658

    OFFER DEADLINE OF SUNDAY 3/1 5pm. Nestled in the prestigious Bennett Point community, “Deerwood” is a stunning Colonial offering over 3,200 sq. ft. of thoughtfully designed living space on a picturesque 5-acre lot. Blending elegance with everyday comfort, this home is ideal for relaxed living and entertaining alike.The interior features a gourmet kitchen with abundant storage, two ovens, and

    Kerry Foley EXP Realty, LLC

    2107 Bennett Point Rd, Queenstown, MD 21658
Maryland Queen Annes 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