2,055

Homes in ZIP Code 21658

Section Image Section Image
  • /43

    $725,000

    • 5 Beds
    • 3.5 Baths
    • 1,992 Sq Ft

    132 Rd, Wye Mills, MD 21679

    Nestled on a private peninsula jutting into the tranquil waters of the Wye Mills lake, 132 Denny Lake Road in Wye Mills, MD, is a breathtaking Dutch Colonial gem. Boasting over 3000 square feet of living space, with a fully finished walk-out basement adding a fourth bedroom and two and a half baths in total, this home offers spectacular lake views from every level. Outside, the bulk headed

    Agent Photo

    BJ Kilby

    Eastern Shore Real Estate, LLC

    132 Rd, Wye Mills, MD 21679
  • /3

    $3,500 Per Month

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    109 Yewell Rd, Queenstown, MD 21658

    Welcome to this charming property located in the delightful Queenstown district of Maryland. Featuring spacious living arrangements, this home is perfect for anyone looking to enjoy a comfortable lifestyle in a vibrant community. This property boasts modern amenities, including central heating and cooling, air conditioning, and ceiling fans to ensure your comfort year-round. With plenty of

    109 Yewell Rd, Queenstown, MD 21658
  • /54

    $835,000

    Sold Nov 14, 2025

    301 Nottingham Ln, Queenstown, MD 21658

    • 4 Beds
    • 3.5 Baths
    • 3,795 Sq Ft
    • Built 2010

    Last Sold Summary

    • $220/SF
    • 108 Days On Market

    Current Estimated Value $861,042

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    301 Nottingham Ln, Queenstown, MD 21658
    • /11

      Not Listed For Sale

      3001 Bennett Point Rd, Queenstown, MD 21658

      3001 Bennett Point Rd, Queenstown, MD 21658

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Shane Hall Compass

  • /61

    $649,900

    $25K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,271 Sq Ft

    144 Wye Knot Rd, Queenstown, MD 21658

    Welcome to 144 Wye Knot Road, where peaceful country living meets everyday convenience. Nestled on 3 private, level acres, this spacious cape cod offers the perfect blend of comfort, functionality, and open space, all within easy reach of Easton, Annapolis, the Bay Bridge, and major commuter routes.A tree-lined paved driveway welcomes you home, while the classic exterior, complete with a

    Agent Photo

    Rachel Best

    RE/MAX Leading Edge

    144 Wye Knot Rd, Queenstown, MD 21658
  • /54

    $2,800 Per Month

    • 1 Bed
    • 1 Bath
    • 864 Sq Ft
    • House for Rent

    1140 Cheston Ln, Queenstown, MD 21658

    Nestled within the serene enclave of Cheston on Wye, this exquisite residential lease offers a unique blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle. Set on a sprawling 10.63-acre lot, this contemporary cedar home is a true sanctuary, boasting breathtaking views of the Wye River and scenic vistas that will captivate your senses. The exterior features two private

    David Kaufmann Eastern Shore Real Estate, LLC

    1140 Cheston Ln, Queenstown, MD 21658
  • /45

    $604,000

    Sold Feb 20, 2026

    119 Wye Knot Rd, Queenstown, MD 21658

    • 3 Beds
    • 2.5 Baths
    • 2,028 Sq Ft
    • Built 1999

    Last Sold Summary

    • $298/SF
    • 62 Days On Market

    Current Estimated Value $589,781

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    119 Wye Knot Rd, Queenstown, MD 21658
    • /35

      Est $893,630

      Not Listed For Sale

      336 Nottingham Ln, Queenstown, MD 21658

      • 3 Beds
      • 2.5 Baths
      • 3,651 Sq Ft
      • Built 2021
      336 Nottingham Ln, Queenstown, MD 21658

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /68

    $1,995,000

    $400K PRICE DROP
    • 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

    377 Hemsley Dr, Queenstown, MD 21658
  • /35

    $2,400 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,332 Sq Ft
    • Townhouse for Rent

    310 Del Rhodes Ave, Queenstown, MD 21658

    Available Now! Move right into this spacious, clean, and beautifully refreshed rental in the heart of Queenstown! Conveniently located within walking distance to local shops, restaurants, and everyday amenities, this home offers the perfect blend of comfort and convenience.Over 2300 SF, featuring 3 bedrooms, 2.5 baths, generous living spaces, and abundant natural light throughout, there's

    Jennifer Chaney Chaney Homes, LLC

    310 Del Rhodes Ave, Queenstown, MD 21658
  • /108

    $4,900,000

    Sold Feb 04, 2026

    2452 Bennett Point Rd, Queenstown, MD 21658

    • 4 Beds
    • 4.5 Baths
    • 6,542 Sq Ft
    • Built 2024

    Last Sold Summary

    • $749/SF
    • 94 Days On Market

    Current Estimated Value $4,677,230

    Last Listing Agent Moe Farley Coldwell Banker Realty

    2452 Bennett Point Rd, Queenstown, MD 21658
    • /44

      Est $1,459,820

      Not Listed For Sale

      136 Governors Way S, Queenstown, MD 21658

      • 3 Beds
      • 2.5 Baths
      • 2,445 Sq Ft
      • Built 2013
      136 Governors Way S, Queenstown, MD 21658

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /75

    $590,000

    $40K PRICE DROP Pending
    • 4 Beds
    • 4 Baths
    • 2,528 Sq Ft

    7121 Main St, Queenstown, MD 21658

    THE ASSUMABLE 3 1/8% MORTGAGE ON THIS HOUSE WOULD SAVE A BUYER SEVERAL HUNDRED DOLLARS ON EACH MONTHLY MORTGAGE PAYMENT. A historic home made new again! Recent improvements include a brand new HVAC system installed in 2023, a water heater replaced in 2022, a new roof and gutters completed in April 2026, refinished butcher block countertops, freshly painted kitchen cabinets, updated stainless

    Micheal Vakas EXP Realty, LLC

    7121 Main St, Queenstown, MD 21658
  • /26

    $399,000

    Sold Nov 06, 2025

    216 Olde Point Ln, Queenstown, MD 21658

    • 3 Beds
    • 2 Baths
    • 1,284 Sq Ft
    • Built 1998

    Last Sold Summary

    • $311/SF
    • 4 Days On Market

    Current Estimated Value $401,202

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    216 Olde Point Ln, Queenstown, MD 21658
    • /50

      Est $4,009,411

      Not Listed For Sale

      380 Wye Narrows Dr, Queenstown, MD 21658

      • 7 Beds
      • 6 Baths
      • 7,040 Sq Ft
      • Built 2019
      380 Wye Narrows Dr, Queenstown, MD 21658

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Brad Kappel TTR Sotheby's International Realty

  • /60

    $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

    Darlene Winegardner RE/MAX Executive

    2006 Bennett Point Rd, Queenstown, MD 21658
  • /7

    $184,000

    Sold Oct 30, 2025

    321 Greenspring Rd, Queenstown, MD 21658

    • Land
    • 1.34 Acres
    • $137,313 per Acre

    Last Sold Summary

    • 603 Days On Market

    Current Estimated Value $189,333

    Last Listing Agent Michael Webster ARE PROS.

    321 Greenspring Rd, Queenstown, MD 21658
    • /3

      Not Listed For Sale

      0 Arrington Rd, Queenstown, MD 21658

      0 Arrington Rd, Queenstown, MD 21658

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Brenda Fornos Taylor Properties

  • /62

    $4,995,000

    $405K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 6,156 Sq Ft

    2800 Bennett Point Rd, Queenstown, MD 21658

    Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and

    Courtney Chipouras TTR Sotheby's International Realty

    2800 Bennett Point Rd, Queenstown, MD 21658
  • /49

    $1,890,000

    Sold Jun 12, 2026

    416 Cove Rd, Queenstown, MD 21658

    • 3 Beds
    • 3.5 Baths
    • 3,396 Sq Ft
    • Built 1957

    Last Sold Summary

    • 2% Above List Price
    • $557/SF
    • 2 Days On Market

    Current Estimated Value $1,832,761

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    416 Cove Rd, Queenstown, MD 21658
    • /35

      Est $467,878

      Not Listed For Sale

      7108 2nd Ave, Queenstown, MD 21658

      • 4 Beds
      • 2 Baths
      • 2,173 Sq Ft
      • Built 1947
      7108 2nd Ave, Queenstown, MD 21658

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Norma Coursey Benson & Mangold, LLC

  • /107

    $2,990,000

    $210K PRICE DROP
    • 4 Beds
    • 7 Baths
    • 4,903 Sq Ft

    121 Kilby Point, Queenstown, MD 21658

    This is more than a waterfront estate - it is an invitation to experience one of Maryland's Eastern Shore's most treasured lifestyles.Step from your private dock onto your boat, and within minutes, you will be cruising the scenic waters of the Wye River and Eastern Bay. Renowned for exceptional crabbing and fishing, the Wye River offers endless opportunities to pull crab pots, teach the

    Dee Dee McCracken Coldwell Banker Realty

    121 Kilby Point, Queenstown, MD 21658
  • /59

    $605,000

    Sold Feb 06, 2026

    235 Wye Knot Ct, Queenstown, MD 21658

    • 4 Beds
    • 2.5 Baths
    • 2,632 Sq Ft
    • Built 2001

    Last Sold Summary

    • $230/SF
    • 21 Days On Market

    Current Estimated Value $608,443

    Last Listing Agent Jarnell Foster Samson Properties

    235 Wye Knot Ct, Queenstown, MD 21658
    • /36

      Est $702,206

      Not Listed For Sale

      117 Nottingham Ln, Queenstown, MD 21658

      • 5 Beds
      • 2.5 Baths
      • 2,570 Sq Ft
      • Built 2010
      117 Nottingham Ln, Queenstown, MD 21658

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /58

    $599,000

    $40K 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
  • /69

    $3,200,000

    Sold May 06, 2026

    3207 Bennett Point Rd, Queenstown, MD 21658

    • 5 Beds
    • 6.5 Baths
    • 7,065 Sq Ft
    • Built 1982

    Last Sold Summary

    • $453/SF
    • 196 Days On Market

    Current Estimated Value $3,233,967

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    3207 Bennett Point Rd, Queenstown, MD 21658
    • /59

      Est $3,616,245

      Not Listed For Sale

      212 Wye Rd, Queenstown, MD 21658

      • 4 Beds
      • 5.5 Baths
      • 7,738 Sq Ft
      • Built 2012
      212 Wye Rd, Queenstown, MD 21658

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /8

    $222,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,172 Sq Ft

    518 Arrington Rd, Queenstown, MD 21658

    Property is located on an acre in a rural setting yet within a 1/2 mile to Route 50. Detached 2 car garage with electric in rear of property. Built-ins remain for extra storage throughout home. Some updates have been made to bath but still elements of the past give it a vintage vibe. Property strictly sold as is. HUD CASE 244-033541. Please see website hudhomestore for details

    Dana Byrd Thurston Wyatt Real Estate, LLC

    518 Arrington Rd, Queenstown, MD 21658
  • /32

    $469,000

    Sold Sep 16, 2025

    100 Rutledge Rd, Queenstown, MD 21658

    • 3 Beds
    • 2 Baths
    • 1,784 Sq Ft
    • Built 1977

    Last Sold Summary

    • $263/SF
    • 1 Day On Market

    Current Estimated Value $498,017

    Last Listing Agent Tina Merrill RE/MAX Executive

    100 Rutledge Rd, Queenstown, MD 21658
    • /23

      Est $571,299

      Not Listed For Sale

      202 Wye Knot Ct, Queenstown, MD 21658

      • 4 Beds
      • 4 Baths
      • 2,682 Sq Ft
      • Built 1999
      202 Wye Knot Ct, Queenstown, MD 21658

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Biana Arentz Coldwell Banker Realty

  • /75

    $3,850,000

    • 5 Beds
    • 4 Baths
    • 3,864 Sq Ft

    491 Wye Island Rd, Queenstown, MD 21658

    From the moment you turn onto winding Carmichael Road and cross the bridge onto Wye Island, the pace begins to slow. Of the island’s approximately 2,800 acres, only about 350 are privately owned. The State of Maryland through the Maryland Park Service owns and manages the rest. ‘The Point’ is among the island’s handful of private properties, distinguished by almost six acres and more than 1,200

    Gerry Gretschel TTR Sotheby's International Realty

    491 Wye Island Rd, Queenstown, MD 21658
  • /80

    $1,340,000

    Sold May 04, 2026

    212 Dutcher Rd, Queenstown, MD 21658

    • 4 Beds
    • 4 Baths
    • 2,996 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Above List Price
    • $447/SF
    • 10 Days On Market

    Current Estimated Value $1,338,631

    Last Listing Agent Kathleen Higginbotham Samson Properties

    212 Dutcher Rd, Queenstown, MD 21658
    • /62

      Est $1,212,164

      Not Listed For Sale

      369 Hemsley Dr, Queenstown, MD 21658

      • 4 Beds
      • 2 Baths
      • 2,728 Sq Ft
      • Built 1976
      369 Hemsley Dr, Queenstown, MD 21658

      Last Sold Summary

      • 359 Days On Market

      Last Listing Agent Darlene Winegardner RE/MAX Executive

  • /45

    $749,000

    • 3 Beds
    • 2 Baths
    • 1,825 Sq Ft

    1520 John Brown Rd, Queenstown, MD 21658

    Welcome to your own private Eastern Shore retreat! Nestled on approximately 17.6 picturesque acres, this charming property offers the perfect blend of peaceful country living and everyday convenience. The home features comfortable one-level living with spacious gathering areas, a cozy wood stove, and beautiful views of the surrounding countryside. Whether you’re looking for room to garden, hunt,

    Andrew Undem Berkshire Hathaway HomeServices Homesale Realty

    1520 John Brown Rd, Queenstown, MD 21658
  • /2

    $725,000

    Sold Feb 27, 2026

    1410 Bennett Point Rd, Queenstown, MD 21658

    • 5 Beds
    • 3 Baths
    • 2,464 Sq Ft
    • Built 1981

    Last Sold Summary

    • $294/SF
    • 3 Days On Market

    Current Estimated Value $720,442

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    1410 Bennett Point Rd, Queenstown, MD 21658
    • /47

      Est $625,295

      Not Listed For Sale

      100 Gloucester Rd, Queenstown, MD 21658

      • 3 Beds
      • 2.5 Baths
      • 2,046 Sq Ft
      • Built 1986
      100 Gloucester Rd, Queenstown, MD 21658

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Jon Ridgeway Berkshire Hathaway HomeServices PenFed Realty

  • /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
  • /73

    $970,000

    Sold Jan 08, 2026

    315 Nottingham Ln, Queenstown, MD 21658

    • 5 Beds
    • 5 Baths
    • 5,152 Sq Ft
    • Built 2019

    Last Sold Summary

    • $188/SF
    • 35 Days On Market

    Current Estimated Value $958,184

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    315 Nottingham Ln, Queenstown, MD 21658
    • /29

      Est $519,467

      Not Listed For Sale

      238 Wye Knot Ct, Queenstown, MD 21658

      • 4 Beds
      • 2.5 Baths
      • 1,859 Sq Ft
      • Built 2000
      238 Wye Knot Ct, Queenstown, MD 21658

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Dana Byrd Thurston Wyatt Real Estate, LLC

  • /42

    $512,000

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    224 Wye Knot Ct, Queenstown, MD 21658

    Welcome to 224 Wye Knot Court, a charming 3-bedroom, 2-bath home situated on a spacious lot in the peaceful Wye Knot Farms community. Step inside to a bright and inviting layout filled with natural light and comfortable, functional living spaces.This well-maintained home offers the perfect opportunity to enjoy the relaxed lifestyle of Maryland’s Eastern Shore. Wye Knot Farms is known for

    Jerilynn Montgomery Long & Foster Real Estate, Inc.

    224 Wye Knot Ct, Queenstown, MD 21658

Showing Results 1 - 40, Page 1 of 18

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