3,028

Homes in ZIP Code 21638

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  • /46

    $824,000

    $15K PRICE DROP Pending
    • 4 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    115 Masters Way, Grasonville, MD 21638

    Great price improvement! 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, and a spacious walk-up “sky

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 213-3524

    115 Masters Way, Grasonville, MD 21638
  • /24

    $1,800 Per Month

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

    107 Winchester Ave Unit 107, Grasonville, MD 21638

    This is a unique offering of a darling and rarely available 1 Bedroom/1 Full Bath Cottage featuring a full-sized Kitchen with all appliances and full-sized washer and dryer in unit. Features ceramic tile in foyer and bath and hardwood throughout. Sliding glass door in Living Room leads to small deck /balcony with view of side yard and large enough for a grill. This unit is electric baseboard

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 724-1674

    107 Winchester Ave Unit 107, 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 $1,629,184

    Last Listing Agent Karla Pinato Northrop Realty

    1017 Long Point Rd, Grasonville, MD 21638
    • /4

      Not Listed For Sale

      109 Watkins Rd, Grasonville, MD 21638

      109 Watkins Rd, Grasonville, MD 21638

      Last Sold Summary

      • 116 Days On Market
      • Last Sold Price $319,500
      • May 16, 2025

      Last Listing Agent Jason Dey Kevin Dey Realty

  • /78

    $1,325,000

    $50K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,000 Sq Ft

    522 Narrows Pointe Dr, Grasonville, MD 21638

    ****DRASTIC PRICE REDUCTION! **** 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

    Agent Photo

    Lori Woods-Fortney

    Berkshire Hathaway HomeServices Homesale Realty

    (443) 234-8115

    522 Narrows Pointe Dr, Grasonville, MD 21638
  • /22

    $3,400 Per Month

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

    206 Prospect Bay Dr W, Grasonville, MD 21638

    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 HVAC.Community offers 18 hole golf course restaurant, swimming

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 927-1628

    206 Prospect Bay Dr W, 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 $2,252,841

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    39 Prospect Bay Dr W, Grasonville, MD 21638
    • /100

      Est $3,048,422

      Not Listed For Sale

      111 Murphy Ln, Grasonville, MD 21638

      • 6 Beds
      • 6 Baths
      • 4,662 Sq Ft
      • Built 1977
      111 Murphy Ln, Grasonville, MD 21638

      Last Sold Summary

      • 9% Above List Price
      • $601/SF
      • 6 Days On Market
      • Last Sold Price $2,800,000
      • May 19, 2025

      Last Listing Agent Ryan Freeman Coldwell Banker Waterman Realty

  • /43

    $879,000

    Under Contract
    • 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
  • /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
  • /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 $785,179

    Last Listing Agent Kathleen Armiger Coldwell Banker Realty

    1000 Chester River Dr, Grasonville, MD 21638
    • /38

      Est $783,575

      Not Listed For Sale

      731 Oyster Cove Dr, Grasonville, MD 21638

      • 3 Beds
      • 2 Baths
      • Built 1987
      731 Oyster Cove Dr, Grasonville, MD 21638

      Last Sold Summary

      • 7% Above List Price
      • 6 Days On Market
      • Last Sold Price $730,000
      • May 16, 2025

      Last Listing Agent Nicole Giordano Coldwell Banker Waterman Realty

  • /98

    $1,375,000

    $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,600 Sq Ft

    105 Port Ct, Grasonville, MD 21638

    BEAUTIFUL 21 ACRE WATERFRONT ESTATE WITH OVER 400' OF WATER FRONTAGE AND SEPARATELY DEEDED DEEP WATER SLIP IS INCLUDED, SLIP #16 AT THE FAR LEFT END OF THE PIER RIGHT ACROSS THE STREET! APPROXIMATELY 6 CLEARED ACRES AND 15 WOODED ACRES. SPECTACULAR 3-STORY HOME WITH 4 LARGE BEDROOMS W/ENSUITE BATHROOMS. RECENT TOP QUALITY GOURMET KITCHEN RENOVATION W/GAS COOKTOP. IT'S AWESOME! ATTACHED 2-CAR

    Agent Photo

    Bruce Fink

    Douglas Realty, LLC

    (443) 339-9114

    105 Port Ct, Grasonville, MD 21638
  • /2

    $8,900

    Total Monthly Price

    • 5 Beds
    • 4 Baths
    • 4,471 Sq Ft
    • Townhouse for Rent

    406 Channel Marker Way, Grasonville, MD 21638

    406 Channel Marker Way, 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 $468,774

    Last Listing Agent Jason French Benson & Mangold, LLC

    337 Whitehouse Dr, Grasonville, MD 21638
    • /34

      Est $414,953

      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
      • May 29, 2023

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

  • /48

    $1,475,000

    • 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
  • /29

    $2,500 Per Month

    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • House for Rent

    421 Sawmill Ln, Grasonville, MD 21638

    Spacious 4-bedroom, 2-bath rental in Grasonville featuring a large yard, greenhouse, shed, and welcoming out door entertaining area. Hardwood floors throughout the living room, hallway and 3 of 4 bedrooms and tile flooring in the kitchen. The oversized primary suite offers laminate flooring, an en-suite bath and walk-in closet, while three additional bedrooms feature wide closets for ample

    Emily Denny Engel & Völkers Annapolis

    421 Sawmill Ln, 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 $885,916

    Last Listing Agent Debbie McQuaid TTR Sotheby's International Realty

    19 Greenwood Shoals, Grasonville, MD 21638
    • /45

      Est $884,516

      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% Below List Price
      • $410/SF
      • 0 Days On Market
      • Last Sold Price $890,000
      • Oct 31, 2024

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /58

    $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
  • /12

    $2,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • House for Rent

    3809 Main St, Grasonville, MD 21638

    # 3809 Main St, Grasonville, MD 21638 — For Rent Welcome to this stunning, never-lived-in home newly constructed from the ground up in the heart of Grasonville! This charming 2-bedroom, 2-bathroom residence blends modern craftsmanship with thoughtful design, offering a fresh and inviting living experience from day one. Step inside to discover a beautifully appointed kitchen featuring all-new

    Vikas Goel Fairfax Realty of Tysons

    3809 Main St, 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 $502,969

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

    503 Chester River Beach Rd, Grasonville, MD 21638
    • /10

      Est $629,749

      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

      • 2% Above List Price
      • $188/SF
      • 34 Days On Market
      • Last Sold Price $619,900
      • Sep 06, 2024

      Last Listing Agent Michelle DiDonato Island Realty, LLC

  • /31

    $619,900

    $10K PRICE DROP 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
  • /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 $2,162,424

    Last Listing Agent Biana Arentz Coldwell Banker Realty

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

      Est $514,002

      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

      • 12% Above List Price
      • $261/SF
      • 30 Days On Market
      • Last Sold Price $460,000
      • Aug 01, 2023

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

  • /64

    $814,999

    $34K PRICE DROP
    • 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. With

    Tricia Wilson Wilson Realty & Staging LLC

    1 Bunker Ct, 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 $516,505

    Last Listing Agent Alex Hodges Cottage Street Realty LLC

    116 Hershey Ct, Grasonville, MD 21638
    • /19

      Not Listed For Sale

      601 Pathfinder Cir Unit LEHIGH, Grasonville, MD 21638

      • 4 Beds
      • 2.5 Baths
      • 3,010 Sq Ft
      • Built 2025
      601 Pathfinder Cir Unit LEHIGH, Grasonville, MD 21638

      Last Sold Summary

      • $210/SF
      • 0 Days On Market
      • Last Sold Price $630,995
      • Apr 04, 2025

      Last Listing Agent Tineshia Johnson NVR, INC.

  • /40

    $825,000

    $25K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,054 Sq Ft

    4 Bunker Ct, Grasonville, MD 21638

    Enjoy a waterfront country club lifestyle with the privacy of wooded views at 4 Bunkers Court! This beautifully updated and private creek front home is tucked away on a wooded 1.53 acre cul-de-sac lot at the top of Little Greenwood Creek in the sought after waterfront golf course community of Prospect Bay. From soaring vaulted ceilings and over $100k of recent thoughtful upgrades throughout, this

    Jennifer Gregorski Washington Fine Properties

    4 Bunker Ct, 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
    • /32

      Not Listed For Sale

      117 Tambor Dr Unit COLUMBIA, Grasonville, MD 21638

      • 4 Beds
      • 2.5 Baths
      • 2,423 Sq Ft
      • Built 2025
      117 Tambor Dr Unit COLUMBIA, Grasonville, MD 21638

      Last Sold Summary

      • $242/SF
      • 0 Days On Market
      • Last Sold Price $586,090
      • Apr 11, 2025

      Last Listing Agent Tineshia Johnson NVR, INC.

  • /67

    $850,000

    • 4 Beds
    • 3 Baths
    • 2,522 Sq Ft

    5 Prospect Bay Dr W, Grasonville, MD 21638

    This charming ranch-style home in the desirable Prospect Bay community offers a perfect blend of comfort and elegance. With 4 spacious bedrooms and 3 full baths, the traditional floor plan features a cozy family room off the gourmet kitchen, ideal for gatherings. Enjoy upgraded countertops and a pantry, complemented by modern stainless steel appliances and huge center island. The large 3 Season

    Tricia Wilson Wilson Realty & Staging LLC

    5 Prospect Bay Dr W, 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 $503,893

    Last Listing Agent Trent Gladstone The KW Collective

    121 Timber Ln, Grasonville, MD 21638
    • /28

      Not Listed For Sale

      211 Pathfinder Cir Unit MOVE IN READY, Grasonville, MD 21638

      • 3 Beds
      • 2 Baths
      • 1,893 Sq Ft
      • Built 2025
      211 Pathfinder Cir Unit MOVE IN READY, Grasonville, MD 21638

      Last Sold Summary

      • $260/SF
      • 132 Days On Market
      • Last Sold Price $492,990
      • Apr 29, 2025

      Last Listing Agent Tineshia Johnson NVR, INC.

  • /53

    $950,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,096 Sq Ft

    335 Prospect Bay Dr W, Grasonville, MD 21638

    Welcome to your private oasis in the coveted community of Prospect Bay! This exceptional 3000 sq ft home offers direct access to Little Greenwood Creek via your private dock. Launch your kayaks right from your backyard and paddle down Little Greenwood Creek out to the bay! But first set your crab pots in the creek. Relax and entertain effortlessly with an incredible covered patio featuring an

    Jerilynn Montgomery Long & Foster Real Estate, Inc.

    335 Prospect Bay Dr W, 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 $462,638

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    208 Grasonville Cemetery Rd, Grasonville, MD 21638
    • /19

      Not Listed For Sale

      413 Pathfinder Cir Unit LEHIGH, Grasonville, MD 21638

      • 4 Beds
      • 2.5 Baths
      • 3,010 Sq Ft
      • Built 2025
      413 Pathfinder Cir Unit LEHIGH, Grasonville, MD 21638

      Last Sold Summary

      • $191/SF
      • 1 Day On Market
      • Last Sold Price $574,135
      • May 09, 2025

      Last Listing Agent Tineshia Johnson NVR, INC.

  • /39

    $615,000

    • 3 Beds
    • 3 Baths
    • 2,381 Sq Ft

    115 Pathfinder Cir, Grasonville, MD 21638

    Welcome to Perry’s Retreat, an exquisite coastal-inspired community in the heart of Grasonville, where luxury living meets the charm of the Chesapeake Bay lifestyle. Built by Ryan Homes, this stunning Craftsman-style residence showcases exceptional curb appeal with a covered front entry, handsome stone accents, classic siding details, and a spacious two-car garage, creating a warm and timeless

    Henry Olaya Northrop Realty

    115 Pathfinder Cir, Grasonville, MD 21638

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