3,023

Homes in ZIP Code 21638

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  • /45

    $829,000

    • 4 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    115 Masters Way, Grasonville, MD 21638

    Great price improvement! Sellers have found home of choice. Welcome to The Enclave at Prospect Bay, where this former model home showcases the sought-after “Pebble Beach” floor plan with thoughtful upgrades and timeless details, backing directly to the 18-hole golf course. Designed for both everyday living and entertaining, the home features three first floor bedrooms, three and a half bathrooms,

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 213-3524

    115 Masters Way, Grasonville, MD 21638
  • /22

    $3,750 per month

    • 3 Beds
    • 2 Baths
    • 1,878 Sq Ft
    • House for Rent

    206 Prospect Bay Dr W, Grasonville, MD 21638

    In person showings will be available as of Monday 3/16. Enjoy everything that the Eastern Shore has to offer just minutes to the Bay Bridge. Great house for entertaining, open space and doors to the outside wrap-around deck. Stunning views of the sunsets and the sunrise. Close to the Marina with beautiful water views. Circular driveway and two car garage. Brand new carpet and paint and new

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 927-1628

    206 Prospect Bay Dr W, Grasonville, MD 21638
  • /99

    $1,650,000 Sold Feb 19, 2026

    1017 Long Point Rd, Grasonville, MD 21638

    • 6 Beds
    • 5 Baths
    • 3,512 Sq Ft
    • Built 1983

    Last Sold Summary

    • $470/SF
    • 3 Days On Market

    Current Estimated Value $1,643,399

    Last Listing Agent Karla Pinato Northrop Realty

    1017 Long Point Rd, Grasonville, MD 21638
    • /28

      Not Listed For Sale

      111 Beach Harbor Unit D-228, Grasonville, MD 21638

      • 2 Beds
      • 2 Baths
      • 1,021 Sq Ft
      • Built 1983
      111 Beach Harbor Unit D-228, Grasonville, MD 21638

      Last Sold Summary

      • $196/SF
      • 142 Days On Market

      Last Sold Price $200,000

      Last Listing Agent Carol Tinnin RE/MAX

  • /77

    $1,375,000

    • 3 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    522 Narrows Pointe Dr, Grasonville, MD 21638

    INCREDIBLE PANORAMIC WATER FRONT VIEWS of the Chester River and The Narrows Waterway from this beautiful 3000 sq ft End Unit Town Home on the Pointe! Imagine sitting on your huge open deck watching the boats go through the channel on their way to the Chesapeake Bay! It's a laid back lifestyle you can get very used to. This Town Home was built for water front living. The floor to ceiling windows

    Agent Photo

    Lori Woods-Fortney

    Berkshire Hathaway HomeServices Homesale Realty

    (443) 234-8115

    522 Narrows Pointe Dr, Grasonville, MD 21638
  • /11

    $1,800 per month

    • 3 Beds
    • 1 Bath
    • 840 Sq Ft
    • Property for Rent

    410 Melvin Ave, Grasonville, MD 21638

    Move right into this charming, completely renovated 3-bedroom, 1-bath home, where modern updates meet cozy living. Step into a bright, open-concept space featuring an eat-in kitchen and an inviting living room. Tucked away at the end of a quiet road, the property boasts a spacious yard that backs to trees for ultimate privacy. Location is everything: you’re just 10 minutes from the Bay Bridge and

    Karen Clark Clark & Co Realty, LLC

    410 Melvin Ave, Grasonville, MD 21638
  • /66

    $2,295,000 Sold Jul 30, 2025

    39 Prospect Bay Dr W, Grasonville, MD 21638

    • 5 Beds
    • 3.5 Baths
    • 4,420 Sq Ft
    • Built 1985

    Last Sold Summary

    • $519/SF
    • 2 Days On Market

    Current Estimated Value $2,222,701

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    39 Prospect Bay Dr W, Grasonville, MD 21638
    • /34

      Est $415,566 Not Listed For Sale

      414 Sawmill Ln, Grasonville, MD 21638

      • 3 Beds
      • 2 Baths
      • 1,168 Sq Ft
      • Built 2014
      414 Sawmill Ln, Grasonville, MD 21638

      Last Sold Summary

      • 2% Above List Price
      • $349/SF
      • 0 Days On Market

      Last Sold Price $408,000

      Last Listing Agent Jeannine Wayson Coldwell Banker (NRT-Southeast-MidAtlantic)

  • /43

    $879,000

    • 4 Beds
    • 3.5 Baths
    • 3,024 Sq Ft

    167 Masters Way, Grasonville, MD 21638

    Welcome to this beautifully upgraded home at the Enclave in Prospect Bay, the Eastern Shore’s premier golf course community, offering main-level living, thoughtful design, and premium finishes throughout. Perfectly situated on a premium lot, this home blends comfort, style, and functionality both inside and out.Located on a private lot next to the golf cart path with access to Prospect Bay’s

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (443) 598-8133

    167 Masters Way, Grasonville, MD 21638
  • /45

    $6,000 per month

    • 5 Beds
    • 5 Baths
    • 3,260 Sq Ft
    • House for Rent

    102 Sea Eagle Dr, Grasonville, MD 21638

    Your waterfront oasis awaits just in time to experience all the Eastern Shore has to offer! Five bedrooms, Five Full bathrooms on three levels. The first floor features an attached garage or foyer entry, a spare bedroom or office or workout room with a full bathroom, living room, dining room and gorgeous kitchen with breakfast nook all overlooking the beautiful water view. You will love

    Jason Dey Kevin Dey Realty

    102 Sea Eagle Dr, Grasonville, MD 21638
  • /49

    $760,000 Sold Sep 12, 2025

    1000 Chester River Dr, Grasonville, MD 21638

    • 2 Beds
    • 1 Bath
    • 1,268 Sq Ft
    • Built 1964

    Last Sold Summary

    • $599/SF
    • 30 Days On Market

    Current Estimated Value $790,092

    Last Listing Agent Kathleen Armiger Coldwell Banker Realty

    1000 Chester River Dr, Grasonville, MD 21638
    • /28

      Est $438,883 Not Listed For Sale

      109 Whitehouse Dr, Grasonville, MD 21638

      • 3 Beds
      • 2.5 Baths
      • 1,304 Sq Ft
      • Built 2018
      109 Whitehouse Dr, Grasonville, MD 21638

      Last Sold Summary

      • 22% Above List Price
      • $276/SF
      • 5 Days On Market

      Last Sold Price $360,000

      Last Listing Agent Shandell Green Real Broker, LLC - Annapolis

  • /48

    $1,475,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,426 Sq Ft

    40 Greenwood Shoals, Grasonville, MD 21638

    Welcome home to this waterfront property in the Eastern Shore’s premier golf course community of Prospect Bay. Set on just over an acre overlooking Little Greenwood Creek, this home offers peaceful views, spacious living areas, and direct water access. From the moment you enter, the welcoming foyer with coat closet opens to a bright living room with large windows plus a stone fireplace, and a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (443) 380-4318

    40 Greenwood Shoals, Grasonville, MD 21638
  • /34

    $450,000 Sold Jun 26, 2025

    337 Whitehouse Dr, Grasonville, MD 21638

    • 5 Beds
    • 3 Baths
    • 2,160 Sq Ft
    • Built 2018

    Last Sold Summary

    • $208/SF
    • 16 Days On Market

    Current Estimated Value $467,646

    Last Listing Agent Jason French Benson & Mangold, LLC

    337 Whitehouse Dr, Grasonville, MD 21638
    • /45

      Est $895,372 Not Listed For Sale

      207 Grandfathers Way, Grasonville, MD 21638

      • 3 Beds
      • 2 Baths
      • 2,172 Sq Ft
      • Built 2010
      207 Grandfathers Way, Grasonville, MD 21638

      Last Sold Summary

      • 1% Above List Price
      • $410/SF
      • 0 Days On Market

      Last Sold Price $890,000

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /31

    $619,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,657 Sq Ft

    113 Aslan Ct, Grasonville, MD 21638

    Move-in ready with extensive recent updates, this 4-bedroom, 2.5-bath home in the sought-after Greenwood Subdivision offers modern comfort, peace of mind, and timeless charm. New improvements include a roof installed in summer 2024, new front and back exterior doors with new window shutters, new carpet in all upstairs bedrooms, and refinished hardwood floors throughout the home. The crawl space

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 914-1649

    113 Aslan Ct, Grasonville, MD 21638
  • /51

    $889,000 Sold Feb 24, 2026

    19 Greenwood Shoals, Grasonville, MD 21638

    • 4 Beds
    • 3 Baths
    • 2,474 Sq Ft
    • Built 1990

    Last Sold Summary

    • $359/SF
    • 1 Day On Market

    Current Estimated Value $898,663

    Last Listing Agent Debbie McQuaid TTR Sotheby's International Realty

    19 Greenwood Shoals, Grasonville, MD 21638
    • /10

      Est $658,891 Not Listed For Sale

      107 Fawn Ln, Grasonville, MD 21638

      • 5 Beds
      • 2.5 Baths
      • 3,291 Sq Ft
      • Built 2024
      107 Fawn Ln, Grasonville, MD 21638

      Last Sold Summary

      • 6% Above List Price
      • $188/SF
      • 34 Days On Market

      Last Sold Price $619,900

      Last Listing Agent Michelle DiDonato Island Realty, LLC

  • /56

    $1,310,000

    • 3 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    346 Narrows Pointe Dr, Grasonville, MD 21638

    Experience Exceptional Waterfront Living on the Chester River! A stunning 3000 sq ft townhome featuring 3 bedrooms, 3.5 bathrooms, a dedicated office and a large bonus room - offering the perfect combination of comfort and flexibility. This was also one of the few "stretch" units- built wider to accommodate setbacks. Inside you'll find an open floor plan that's perfect for entertaining! It has

    Agent Photo

    Lori Woods-Fortney

    Berkshire Hathaway HomeServices Homesale Realty

    (443) 665-8250

    346 Narrows Pointe Dr, Grasonville, MD 21638
  • /3

    $465,000 Sold Jun 26, 2025

    503 Chester River Beach Rd, Grasonville, MD 21638

    • 3 Beds
    • 2 Baths
    • 1,602 Sq Ft
    • Built 1963

    Last Sold Summary

    • $290/SF
    • 3 Days On Market

    Current Estimated Value $500,472

    Last Listing Agent Sharon Tryon Long & Foster Real Estate, Inc.

    503 Chester River Beach Rd, Grasonville, MD 21638
    • /28

      Not Listed For Sale

      231 Evans Ave, Grasonville, MD 21638

      • 3 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1982
      231 Evans Ave, Grasonville, MD 21638

      Last Sold Summary

      • $182/SF
      • 121 Days On Market

      Last Sold Price $199,900

      Last Listing Agent John Cary Rosendale Realty

  • /72

    $1,250,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 2,834 Sq Ft

    1009 Oyster Cove Dr, Grasonville, MD 21638

    Finally, one of the highly sought-after “Big Six” Waterfront Townhomes is available—complete with an attached garage and deeded boat slip (M1-PB-11) in the protected North Marina. This exceptional property truly represents the best of Waterfront Living. Fully renovated just four years ago with top-of-the-line finishes and beautiful coastal design throughout. Features include 3⁄4" luxury vinyl

    Agent Photo

    Lori Woods-Fortney

    Berkshire Hathaway HomeServices Homesale Realty

    (410) 881-8561

    1009 Oyster Cove Dr, Grasonville, MD 21638
  • /44

    $2,149,000 Sold Oct 24, 2025

    7 Parsons Island View, Grasonville, MD 21638

    • 4 Beds
    • 3.5 Baths
    • 3,281 Sq Ft
    • Built 1982

    Last Sold Summary

    • $655/SF
    • 2 Days On Market

    Current Estimated Value $2,126,424

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    7 Parsons Island View, Grasonville, MD 21638
    • /56

      Est $510,268 Not Listed For Sale

      167 Caspian Dr, Grasonville, MD 21638

      • 3 Beds
      • 2 Baths
      • 1,765 Sq Ft
      • Built 2012
      167 Caspian Dr, Grasonville, MD 21638

      Last Sold Summary

      • 11% Above List Price
      • $261/SF
      • 30 Days On Market

      Last Sold Price $460,000

      Last Listing Agent Gina White Coldwell Banker (NRT-Southeast-MidAtlantic)

  • /53

    $725,000

    • 4 Beds
    • 3.5 Baths
    • 3,668 Sq Ft

    621 Caspian Dr, Grasonville, MD 21638

    Stunning Colonial in the Heart of Greenwood – this exquisitely maintained, show-stopping colonial boasts over 3,600 square feet of pure luxury. The stately brick front makes this property an absolute standout! The open-concept main level includes a grand two-story foyer, with formal living and dining rooms flanked on either side. Behind the living room, there's a den/office with double

    Agent Photo

    Tracey McCallum

    Chaney Homes, LLC

    (410) 873-7135

    621 Caspian Dr, Grasonville, MD 21638
  • /34

    $480,000 Sold Jun 06, 2025

    116 Hershey Ct, Grasonville, MD 21638

    • 4 Beds
    • 2.5 Baths
    • 2,042 Sq Ft
    • Built 2008

    Last Sold Summary

    • $235/SF
    • 12 Days On Market

    Current Estimated Value $513,190

    Last Listing Agent Alex Hodges Cottage Street Realty LLC

    116 Hershey Ct, Grasonville, MD 21638
    • /25

      Not Listed For Sale

      118 Greybull Ln Unit BALLENGER, Grasonville, MD 21638

      • 4 Beds
      • 2.5 Baths
      • 2,114 Sq Ft
      • Built 2025
      118 Greybull Ln Unit BALLENGER, Grasonville, MD 21638

      Last Sold Summary

      • $242/SF
      • 10 Days On Market

      Last Sold Price $511,855

      Last Listing Agent Tineshia Johnson NVR, INC.

  • /36

    $499,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,141 Sq Ft

    3636 Dexter Ct Unit HARPER-142, Grasonville, MD 21638

    STILL TIME TO PICK YOUR FINISHES- AND MOVE IN BEFORE THE END OF THE YEAR! Luxury Villa with a 1st floor Owner's suite. The layout is welcoming and very functional. Featuring a huge family room, dining area and stunning kitchen. The Owner's suite is located conveniently on the first floor and includes a large walk-in closet and private bath which boasts ceramic tile, a double bowl sink, private

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 449-7960

    3636 Dexter Ct Unit HARPER-142, Grasonville, MD 21638
  • /54

    $660,000 Sold Jan 15, 2026

    601 Pathfinder Cir, Grasonville, MD 21638

    • 5 Beds
    • 3 Baths
    • 3,010 Sq Ft
    • Built 2024

    Last Sold Summary

    • $219/SF
    • 45 Days On Market

    Last Listing Agent Andrew Undem Berkshire Hathaway HomeServices Homesale Realty

    601 Pathfinder Cir, Grasonville, MD 21638
    • /48

      Est $343,789 Not Listed For Sale

      114 Station Ln, Grasonville, MD 21638

      • 3 Beds
      • 2 Baths
      • 1,783 Sq Ft
      • Built 1956
      114 Station Ln, Grasonville, MD 21638

      Last Sold Summary

      • 7% Above List Price
      • $179/SF
      • 205 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Lona Todd Taylor Properties

  • /23

    $149,000

    • Land
    • 0.5 Acre
    • $298,000 per Acre

    141 Sawmill Ln, Grasonville, MD 21638

    Major Price Improvement! 0.5 +/- acres of building lot ready to go! Sewer is installed! Recorded lots and site improvements are complete, making it ready for your house plans to submit to the County. This lot is part of a three-lot minor subdivision for sale in Grasonville, MD. You can also purchase the entire set. No builder tie-in, use yours or one of ours.

    Vincent Payne Realty Navigator

    141 Sawmill Ln, Grasonville, MD 21638
  • /45

    $449,900 Sold Jun 13, 2025

    121 Timber Ln, Grasonville, MD 21638

    • 4 Beds
    • 2.5 Baths
    • 2,230 Sq Ft
    • Built 2001

    Last Sold Summary

    • $202/SF
    • 44 Days On Market

    Current Estimated Value $490,443

    Last Listing Agent Trent Gladstone The KW Collective

    121 Timber Ln, Grasonville, MD 21638
    • /35

      Est $469,640 Not Listed For Sale

      116 Whitehouse Dr, Grasonville, MD 21638

      • 3 Beds
      • 2 Baths
      • 1,426 Sq Ft
      • Built 2012
      116 Whitehouse Dr, Grasonville, MD 21638

      Last Sold Summary

      • 8% Above List Price
      • $305/SF
      • 34 Days On Market

      Last Sold Price $435,000

      Last Listing Agent Pasquale Carannante RE/MAX

  • /64

    $849,000 Open Thu 4PM - 6PM

    • 4 Beds
    • 3 Baths
    • 2,604 Sq Ft

    1 Bunker Ct, Grasonville, MD 21638

    Discover the charm of this beautifully renovated split-level home in the desirable Prospect Bay community. With 4 spacious bedrooms and 3 full baths, this residence boasts an inviting interior featuring upgraded countertops, LVP floors, and cozy exposed beams. The heart of the home is the combination kitchen/dining area, perfect for gatherings that can flow outside to the new expanded deck. Enjoy

    Tricia Wilson Wilson Realty & Staging LLC

    1 Bunker Ct, Grasonville, MD 21638
  • /35

    $450,000 Sold Feb 24, 2026

    208 Grasonville Cemetery Rd, Grasonville, MD 21638

    • 3 Beds
    • 2 Baths
    • 2,044 Sq Ft
    • Built 1967

    Last Sold Summary

    • 3% Below List Price
    • $220/SF
    • 14 Days On Market

    Current Estimated Value $465,743

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    208 Grasonville Cemetery Rd, Grasonville, MD 21638
    • /59

      Est $1,320,449 Not Listed For Sale

      56 Prospect Bay Dr W, Grasonville, MD 21638

      • 3 Beds
      • 3.5 Baths
      • 2,940 Sq Ft
      • Built 1987
      56 Prospect Bay Dr W, Grasonville, MD 21638

      Last Sold Summary

      • 193% Above List Price
      • $153/SF
      • 5 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Judy Moore Benson & Mangold, LLC

  • /37

    $689,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,882 Sq Ft

    344 Prospect Bay Dr W, Grasonville, MD 21638

    Nestled in the serene Prospect Bay community, this charming ranch-style home offers a perfect blend of comfort and convenience. Roof is only 3-4 years old. HVAC 2024-2025 . Hardie Plank Siding and Soffits were installed only a couple of years ago, with Aztec PVC Trim and new gutters and gutter guards, make this pretty much a maintenance free home. With three bedrooms and two full bathrooms, this

    Dina Baxter Rosendale Realty

    344 Prospect Bay Dr W, Grasonville, MD 21638
  • /51

    $606,000 Sold Mar 16, 2026

    108 Perrys Retreat Blvd, Grasonville, MD 21638

    • 4 Beds
    • 2.5 Baths
    • 2,450 Sq Ft
    • Built 2022

    Last Sold Summary

    • $247/SF
    • 116 Days On Market

    Last Listing Agent Dan Foster Long & Foster Real Estate, Inc.

    108 Perrys Retreat Blvd, Grasonville, MD 21638
    • /49

      Est $1,125,960 Not Listed For Sale

      1 Keel Haul Dr, Grasonville, MD 21638

      • 4 Beds
      • 4 Baths
      • 3,072 Sq Ft
      • Built 1986
      1 Keel Haul Dr, Grasonville, MD 21638

      Last Sold Summary

      • 22% Above List Price
      • $299/SF
      • 3 Days On Market

      Last Sold Price $920,000

      Last Listing Agent Jimmy White Long & Foster

  • /81

    $849,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,367 Sq Ft

    322 Prospect Bay Dr W, Grasonville, MD 21638

    Welcome to this fabulous residence in the coveted Prospect Bay community of Grasonville, where timeless Cape Cod charm meets comfort, space, and an exceptional lifestyle. Thoughtfully designed and beautifully maintained, this picturesque home offers the perfect blend of elegance and functionality. The home features four generously sized bedrooms, including a highly desirable private guest or au

    Colleen Smith EXP Realty, LLC

    322 Prospect Bay Dr W, Grasonville, MD 21638

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