27,773

Queen Annes County, MD Homes

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  • 141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    /61

    $684,950

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    141 Switchgrass Way Unit 34, Chester, MD 21619

    **** NICE VIEWS OF THE CHESTER RIVER**** ***** LOWEST PRICED SEVERN MODEL****K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resort-style and maintenance-free living at its finest! Shows Like a Model!!! The Severn design is a spacious and airy 3 bedroom, 2.5 bath end-unit boasting an

    Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
  • 957 Cloverfields Dr, Stevensville, MD 21666
    957 Cloverfields Dr, Stevensville, MD 21666
    957 Cloverfields Dr, Stevensville, MD 21666
    /31

    $285,000 Sold Dec 12, 2025

    957 Cloverfields Dr, Stevensville, MD 21666

    • 3 Beds
    • 1 Bath
    • 1,300 Sq Ft
    • Built 1975

    Last Sold Summary

    • $219/SF
    • 9 Days On Market

    Last Listing Agent Rebecca Gray Keller Williams Legacy

    957 Cloverfields Dr, Stevensville, MD 21666
    • 650 Chester River Beach Rd, Grasonville, MD 21638
      650 Chester River Beach Rd, Grasonville, MD 21638
      650 Chester River Beach Rd, Grasonville, MD 21638
      /57

      Est $979,491 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,950 Sq Ft

      650 Chester River Beach Rd, Grasonville, MD 21638

      650 Chester River Beach Rd, Grasonville, MD 21638
  • 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
  • 242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
    /36

    $705,000 Sold Sep 23, 2025

    242 Peregrine Dr, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft
    • Built 2024

    Last Sold Summary

    • $224/SF
    • 111 Days On Market

    Last Listing Agent Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Chester, MD 21619
    • 100 Gloucester Rd, Queenstown, MD 21658
      100 Gloucester Rd, Queenstown, MD 21658
      100 Gloucester Rd, Queenstown, MD 21658
      /47

      Est $600,288 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,046 Sq Ft

      100 Gloucester Rd, Queenstown, MD 21658

      100 Gloucester Rd, Queenstown, MD 21658
  • 203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    /68

    $1,099,900 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,036 Sq Ft

    203 Riverside Dr, Chester, MD 21619

    To-be-built 5BR, 3.5BA waterfront home by Laine Street Homes — now under construction and perfectly positioned to capture breathtaking sunrises over the waterfront of Crab Alley Creek. Thoughtfully designed for modern coastal living, this home will offer panoramic water views from the main level and the primary suite, filling the interior with natural light and scenic beauty. The bright layout

    Chrissy Schultz Long & Foster Real Estate, Inc.

    203 Riverside Dr, Chester, MD 21619
  • 2921 Cox Neck Rd E, Chester, MD 21619
    2921 Cox Neck Rd E, Chester, MD 21619
    2921 Cox Neck Rd E, Chester, MD 21619
    /66

    $1,700,000 Sold Jul 11, 2025

    2921 Cox Neck Rd E, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,824 Sq Ft
    • Built 1992

    Last Sold Summary

    • $602/SF
    • 2 Days On Market

    Current Estimated Value $1,654,001

    Last Listing Agent Lynn Tuozzo Berkshire Hathaway HomeServices PenFed Realty

    2921 Cox Neck Rd E, Chester, MD 21619
    • 42A Queen Catherine Ct, Chester, MD 21619
      42A Queen Catherine Ct, Chester, MD 21619
      42A Queen Catherine Ct, Chester, MD 21619
      /49

      Est $445,477 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,008 Sq Ft

      42A Queen Catherine Ct, Chester, MD 21619

      42A Queen Catherine Ct, Chester, MD 21619
  • 3 Ackerman Ct, Stevensville, MD 21666
    3 Ackerman Ct, Stevensville, MD 21666
    3 Ackerman Ct, Stevensville, MD 21666
    /61

    $585,900 Under Contract

    • 5 Beds
    • 3 Baths
    • 2,116 Sq Ft

    3 Ackerman Ct, Stevensville, MD 21666

    Enjoy Eastern Shore living at its best! This 2,116 sq ft, 5 Bedrooms, 3 full baths Coastal home is nestled in one of the Eastern Shore most desirable waterfront communities. Cloverfields is conveniently located to waterfront restaurants and shopping. This sprawling ranch style home has been beautifully renovated. Home offers 2 primary bedrooms, all new bathrooms with tiled showers, 2 laundry

    Penny Windsor Benson & Mangold, LLC

    3 Ackerman Ct, Stevensville, MD 21666
  • 300 Oak St, Centreville, MD 21617
    300 Oak St, Centreville, MD 21617
    /2

    $275,000 Sold Sep 16, 2025

    300 Oak St, Centreville, MD 21617

    • 2 Beds
    • 1 Bath
    • 1,064 Sq Ft
    • Built 1964

    Last Sold Summary

    • $258/SF
    • 0 Days On Market

    Current Estimated Value $281,798

    Last Listing Agent Chris Rosendale CR Realty

    300 Oak St, Centreville, MD 21617
    • 244 Bentons Pleasure Rd, Chester, MD 21619
      244 Bentons Pleasure Rd, Chester, MD 21619
      244 Bentons Pleasure Rd, Chester, MD 21619
      /61

      Est $730,861 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      244 Bentons Pleasure Rd, Chester, MD 21619

      244 Bentons Pleasure Rd, Chester, MD 21619
  • LOT 4 Finley Creek Dr, Centreville, MD 21617
    LOT 4 Finley Creek Dr, Centreville, MD 21617
    /2

    $1,053,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,575 Sq Ft

    LOT 4 Finley Creek Dr, Centreville, MD 21617

    Finley Creek Estates, an exclusive new community nestled in between Centreville and historic Chestertown situated on 1 plus acre lots. This luxurious estate like home is to be built by Red oak Properties, LLC, one of the Eastern Shore Premier builders. One lot remains with this builder. Call for additional details.

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    LOT 4 Finley Creek Dr, Centreville, MD 21617
  • 908 Monroe Manor Rd, Stevensville, MD 21666
    908 Monroe Manor Rd, Stevensville, MD 21666
    908 Monroe Manor Rd, Stevensville, MD 21666
    /43

    $1,010,000 Sold Mar 27, 2025

    908 Monroe Manor Rd, Stevensville, MD 21666

    • 4 Beds
    • 2 Baths
    • 2,372 Sq Ft
    • Built 1965

    Last Sold Summary

    • $426/SF
    • 37 Days On Market

    Current Estimated Value $1,020,521

    Last Listing Agent Lynn Collins Long & Foster Real Estate, Inc.

    908 Monroe Manor Rd, Stevensville, MD 21666
    • 915 Auckland Way, Chester, MD 21619
      915 Auckland Way, Chester, MD 21619
      915 Auckland Way, Chester, MD 21619
      /46

      Est $476,757 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,100 Sq Ft

      915 Auckland Way, Chester, MD 21619

      915 Auckland Way, Chester, MD 21619
  • 154 Harrier Way, Chester, MD 21619
    154 Harrier Way, Chester, MD 21619
    154 Harrier Way, Chester, MD 21619
    /45

    $639,450

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft

    154 Harrier Way, Chester, MD 21619

    *** WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND***Price Reduced! Lowest priced single family home in Four Seasons! Better than New! Custom Window Treatments! Oversized Garage w/Broadcast Floor!Why Wait Months-and Spend Thousands More-You Can Move into This Home in 30 Days. ****** Owner is also offering a Home Warranty with acceptable offer******The Donegal model is a

    Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
  • 349 Wicomico Rd, Stevensville, MD 21666
    349 Wicomico Rd, Stevensville, MD 21666
    349 Wicomico Rd, Stevensville, MD 21666
    /34

    $495,000 Sold Sep 26, 2025

    349 Wicomico Rd, Stevensville, MD 21666

    • 4 Beds
    • 2 Baths
    • 1,652 Sq Ft
    • Built 1985

    Last Sold Summary

    • $300/SF
    • 26 Days On Market

    Last Listing Agent Nick Waldner Keller Williams Realty Centre

    349 Wicomico Rd, Stevensville, MD 21666
    • 116 Jean Rd, Stevensville, MD 21666
      116 Jean Rd, Stevensville, MD 21666
      116 Jean Rd, Stevensville, MD 21666
      /54

      Est $812,802 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,010 Sq Ft

      116 Jean Rd, Stevensville, MD 21666

      116 Jean Rd, Stevensville, MD 21666
  • 108 Wall St, Queenstown, MD 21658
    108 Wall St, Queenstown, MD 21658
    108 Wall St, Queenstown, MD 21658
    /29

    $349,900 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,033 Sq Ft

    108 Wall St, Queenstown, MD 21658

    Discover the charm of this beautiful LIKE NEW cottage, set to impress with its thoughtful design, modern upgrades and convenient location. This home has undergone a complete renovation, including a redesigned floor plan. Everything in the property is brand new, with no expense spared. The updates include -New roof, windows, siding, gutters, insulation, electric, plumbing, HVAC and the list goes

    Karen Clark Clark & Co Realty, LLC

    108 Wall St, Queenstown, MD 21658
  • 222 Beck Farm Rd, Centreville, MD 21617
    222 Beck Farm Rd, Centreville, MD 21617
    222 Beck Farm Rd, Centreville, MD 21617
    /54

    $695,000 Sold Jan 13, 2025

    222 Beck Farm Rd, Centreville, MD 21617

    • 4 Beds
    • 4 Baths
    • 4,320 Sq Ft
    • Built 2002

    Last Sold Summary

    • $161/SF
    • 75 Days On Market

    Current Estimated Value $717,283

    Last Listing Agent Denise Giacobba Samson Properties

    222 Beck Farm Rd, Centreville, MD 21617
    • 306 Drake Tail Place, Chester, MD 21619
      306 Drake Tail Place, Chester, MD 21619
      306 Drake Tail Place, Chester, MD 21619
      /27

      Est $343,085 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,440 Sq Ft

      306 Drake Tail Place, Chester, MD 21619

      306 Drake Tail Place, Chester, MD 21619
  • 113 Collier Rd, Grasonville, MD 21638
    113 Collier Rd, Grasonville, MD 21638
    /2

    $385,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,287 Sq Ft

    113 Collier Rd, Grasonville, MD 21638

    Welcome to 117 Collier Road in Grasonville, Maryland—an action-packed rancher situated on an oversized corner lot. This well-maintained home features a fully fenced backyard and clearly reflects pride of ownership inside and out. Offering 3 bedrooms, 2 full baths, and an open floor plan designed for comfortable family living. Enjoy the freedom of NO HOA, with convenient access to shopping,

    Mary Julie Long & Foster Real Estate, Inc.

    113 Collier Rd, Grasonville, MD 21638
  • 209 River Rd, Chestertown, MD 21620
    209 River Rd, Chestertown, MD 21620
    209 River Rd, Chestertown, MD 21620
    /3

    $124,000 Sold Aug 25, 2025

    209 River Rd, Chestertown, MD 21620

    • Land
    • 1.01 Acres
    • $122,772 per Acre

    Last Sold Summary

    • 8 Days On Market

    Current Estimated Value $125,843

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    209 River Rd, Chestertown, MD 21620
    • 112 Maryland Rd, Stevensville, MD 21666
      112 Maryland Rd, Stevensville, MD 21666
      112 Maryland Rd, Stevensville, MD 21666
      /26

      Est $448,254 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,692 Sq Ft

      112 Maryland Rd, Stevensville, MD 21666

      112 Maryland Rd, Stevensville, MD 21666
  • 233 N Field Way, Centreville, MD 21617
    233 N Field Way, Centreville, MD 21617
    233 N Field Way, Centreville, MD 21617
    /50

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 3,374 Sq Ft

    233 N Field Way, Centreville, MD 21617

    Welcome to 233 Northfield Way - A True North Brook Beauty! This stunning Colonial in the highly sought-after North Brook community offers over 3,300 sq. ft. of true living space, beautifully maintained and filled with natural light. As you arrive, you’ll notice the mature landscaping that perfectly complements this home’s curb appeal. Step inside to an inviting open floor plan, to the right, a

    Crystal Smith RE/MAX Executive

    233 N Field Way, Centreville, MD 21617
  • 205 Pinder Hill Rd, Church Hill, MD 21623
    205 Pinder Hill Rd, Church Hill, MD 21623
    205 Pinder Hill Rd, Church Hill, MD 21623
    /23

    $375,000 Sold May 28, 2025

    205 Pinder Hill Rd, Church Hill, MD 21623

    • 5 Beds
    • 3 Baths
    • 2,052 Sq Ft
    • Built 2003

    Last Sold Summary

    • $183/SF
    • 0 Days On Market

    Last Listing Agent Linda Austin Long & Foster Real Estate, Inc.

    205 Pinder Hill Rd, Church Hill, MD 21623
    • 605 Bayside Dr, Stevensville, MD 21666
      605 Bayside Dr, Stevensville, MD 21666
      605 Bayside Dr, Stevensville, MD 21666
      /96

      Est $625,569 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,104 Sq Ft

      605 Bayside Dr, Stevensville, MD 21666

      605 Bayside Dr, Stevensville, MD 21666
  • 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
  • 701 Harmony Way, Centreville, MD 21617
    701 Harmony Way, Centreville, MD 21617
    701 Harmony Way, Centreville, MD 21617
    /74

    $499,000 Sold May 08, 2025

    701 Harmony Way, Centreville, MD 21617

    • 3 Beds
    • 2 Baths
    • 2,284 Sq Ft
    • Built 2010

    Last Sold Summary

    • $218/SF
    • 2 Days On Market

    Current Estimated Value $512,579

    Last Listing Agent Edward Beres RE/MAX Executive

    701 Harmony Way, Centreville, MD 21617
    • 720 Old Love Point Rd, Stevensville, MD 21666
      720 Old Love Point Rd, Stevensville, MD 21666
      720 Old Love Point Rd, Stevensville, MD 21666
      /33

      Est $455,992 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft

      720 Old Love Point Rd, Stevensville, MD 21666

      720 Old Love Point Rd, Stevensville, MD 21666
  • 0 Hatchett Rd, Centreville, MD 21617
    0 Hatchett Rd, Centreville, MD 21617
    0 Hatchett Rd, Centreville, MD 21617
    /7

    $169,000

    • Land
    • 2.55 Acres
    • $66,275 per Acre

    0 Hatchett Rd, Centreville, MD 21617

    Escape to the country in this hard to find 2.5 acre lot zoned agriculture in a beautiful country setting before its gone. No HOA, Covenants or Restrictions (rare) so bring the critters or home based business. Perc approved. Bring your house plans and builder or invest for later. See what all the rave is about and move to the Eastern Shore with historic towns nearby, public boat ramps, boat

    Lona Todd Taylor Properties

    0 Hatchett Rd, Centreville, MD 21617
  • 112 Port Ct, Grasonville, MD 21638
    112 Port Ct, Grasonville, MD 21638
    112 Port Ct, Grasonville, MD 21638
    /71

    $1,136,462 Sold May 30, 2025

    112 Port Ct, Grasonville, MD 21638

    • 4 Beds
    • 3.5 Baths
    • 3,889 Sq Ft
    • Built 2004

    Last Sold Summary

    • $292/SF
    • 50 Days On Market

    Current Estimated Value $1,257,586

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    112 Port Ct, Grasonville, MD 21638
    • 504 Perrys Corner Rd, Grasonville, MD 21638
      504 Perrys Corner Rd, Grasonville, MD 21638
      504 Perrys Corner Rd, Grasonville, MD 21638
      /22

      Est $373,011 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,348 Sq Ft

      504 Perrys Corner Rd, Grasonville, MD 21638

      504 Perrys Corner Rd, Grasonville, MD 21638
  • 54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    /3

    $349,000

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft

    54H Queen Caroline Ct, Chester, MD 21619

    Professional pictures coming! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout, as will be getting new flooring in the kitchen. A propane fireplace highlights the great room for cozy chilly nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit it offers lots of

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, Chester, MD 21619
  • 230 Johnny Ln, Stevensville, MD 21666
    230 Johnny Ln, Stevensville, MD 21666
    230 Johnny Ln, Stevensville, MD 21666
    /65

    $419,000 Sold May 21, 2025

    230 Johnny Ln, Stevensville, MD 21666

    • 3 Beds
    • 2.5 Baths
    • 1,864 Sq Ft
    • Built 1981

    Last Sold Summary

    • $225/SF
    • 4 Days On Market

    Current Estimated Value $426,169

    Last Listing Agent Jonathan Olsavsky Coldwell Banker Waterman Realty

    230 Johnny Ln, Stevensville, MD 21666
    • 219 Ashland Dr, Centreville, MD 21617
      219 Ashland Dr, Centreville, MD 21617
      219 Ashland Dr, Centreville, MD 21617
      /27

      Est $736,126 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,730 Sq Ft

      219 Ashland Dr, Centreville, MD 21617

      219 Ashland Dr, Centreville, MD 21617
  • 121 Wheelhouse Way Unit 2111, Chester, MD 21619
    121 Wheelhouse Way Unit 2111, Chester, MD 21619
    121 Wheelhouse Way Unit 2111, Chester, MD 21619
    /73

    $539,900 Pending

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    121 Wheelhouse Way Unit 2111, Chester, MD 21619

    This Magothy condo offers low-maintenance luxury with a smart layout and designer features. With 2 bedrooms, 2.5 bathrooms, a 1-car garage, and a dedicated home office with French doors, it’s the perfect mix of comfort and versatility. Enjoy cozy evenings by the electric fireplace or entertaining at the built-in dry bar.The kitchen includes quartz countertops, a gas cooktop, range hood,

    Mary Anne Kowalewski KOVO Realty

    121 Wheelhouse Way Unit 2111, Chester, MD 21619
  • 408 Five Farms Dr, Stevensville, MD 21666
    408 Five Farms Dr, Stevensville, MD 21666
    /2

    $865,300 Sold Jun 13, 2025

    408 Five Farms Dr, Stevensville, MD 21666

    • 3 Beds
    • 2 Baths
    • Built 2025

    Last Sold Summary

    • 3 Days On Market

    Current Estimated Value $833,531

    Last Listing Agent DJ Dauses Coldwell Banker Waterman Realty

    408 Five Farms Dr, Stevensville, MD 21666
    • 227 N Commerce St, Centreville, MD 21617
      227 N Commerce St, Centreville, MD 21617
      227 N Commerce St, Centreville, MD 21617
      /63

      Est $518,280 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,317 Sq Ft

      227 N Commerce St, Centreville, MD 21617

      227 N Commerce St, Centreville, MD 21617
  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /8

    $88,900

    • Land
    • 0.48 Acre
    • $185,208 per Acre

    0 East St, Chestertown, MD 21620

    This corner lot offers a rare opportunity to build just minutes from Downtown Chestertown. Located on a quiet street and close to the Chester River, this property combines a peaceful setting with everyday convenience.The lot is perc approved and has site plans—see documents for details. With close proximity to Chestertown’s shops, galleries, and restaurants, it’s the perfect setting for those

    William Norris Select Land & Homes, LLC

    0 East St, Chestertown, MD 21620

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