• Home
  • Buy
    1. All Listings
    2. Featured Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
    3. Recent Sold
  • Rent
    1. Rental Listings
  • Bayside Realty
  • Featured Areas
    1. Easton Overview
    2. Denton Overview
    3. Trappe Overview
    4. Chestertown Overview
    5. Saint Michaels Overview
    6. Ridgely Overview
    7. Berlin Overview
  • About
    1. My Team
    2. About Us
    3. Contact Us
    4. Reviews
  • Market Snapshot
    • Register
    • Sign In
    Price
    • Any
    • $ 100,000
    • $ 150,000
    • $ 200,000
    • $ 400,000
    • $ 800,000
    • Any
    • $ 200,000
    • $ 300,000
    • $ 400,000
    • $ 600,000
    • $ 1,000,000
      Beds Tap two numbers to select a range
      Any
      1
      2
      3
      4
      5+
      Baths Tap two numbers to select a range
      Any
      1
      2
      3
      4
      5+
    • List
    • Mixed
    • Map
    Neighborhood: Chester, Chester, MD
    Virtual Tour
    Map
    32 Properties Available In Chester

    32 Properties Available In Chester

    • Default
    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    MD >Chester >Chester >
    Market Insights
    121 MERLIN DR, Chester, MD 21619
    1/84
    Open 7/19 12PM-3PM

    $719,900

    2 Beds2 Baths2,118 SqFt

    121 MERLIN DR, Chester, MD 21619

    MLS# MDQA2017900

    Listed by Coldwell Banker Realty

    Bright MLS (BMLS)
    2645 COX NECK RD, Chester, MD 21619
    1/61
    Open Sun 11AM-1PM

    $399,500

    3 Beds2 Baths1,192 SqFt

    2645 COX NECK RD, Chester, MD 21619

    MLS# MDQA2017640

    Listed by Compass

    Bright MLS (BMLS)
    1757 HARBOR DR, Chester, MD 21619
    1/64
    Open 7/19 2:30PM-4PM

    $1,294,800

    4 Beds4 Baths0.55 Acres Lot

    1757 HARBOR DR, Chester, MD 21619

    MLS# MDQA2014542

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
    300 WOODS POINT RD, Chester, MD 21619
    1/69
    New

    $2,840,000

    3 Beds2 Baths1,704 SqFt

    300 WOODS POINT RD, Chester, MD 21619

    MLS# MDQA2017820

    Listed by Tidewater Properties

    Bright MLS (BMLS)
    29-D QUEEN MARY CT, Chester, MD 21619
    1/66
    New

    $359,000

    3 Beds3 Baths1,440 SqFt

    29-D QUEEN MARY CT, Chester, MD 21619

    MLS# MDQA2017974

    Listed by Rosendale Realty

    Bright MLS (BMLS)
    6010 BRIDGEPOINTE DR, Chester, MD 21619
    1/55
    Active

    $387,500

    3 Beds2 Baths1,885 SqFt

    6010 BRIDGEPOINTE DR, Chester, MD 21619

    MLS# MDQA2017824

    Listed by Rosendale Realty

    Bright MLS (BMLS)
    7013 BRIDGEPOINTE DR, Chester, MD 21619
    1/48
    Active

    $375,000

    3 Beds3 Baths1,635 SqFt

    7013 BRIDGEPOINTE DR, Chester, MD 21619

    MLS# MDQA2017430

    Listed by Coldwell Banker Realty

    Bright MLS (BMLS)
    205 RIVERSIDE DR, Chester, MD 21619
    1/38
    Active

    $749,000

    3 Beds2 Baths1,524 SqFt

    205 RIVERSIDE DR, Chester, MD 21619

    MLS# MDQA2017690

    Listed by Engel & Volkers Annapolis

    Bright MLS (BMLS)
    328 BENTONS PLEASURE RD, Chester, MD 21619
    1/84
    Pending

    $2,049,000

    5 Beds4 Baths3,250 SqFt

    328 BENTONS PLEASURE RD, Chester, MD 21619

    MLS# MDQA2017668

    Listed by HomeZu by Simple Choice

    Bright MLS (BMLS)
    1000 HERONS NEST WAY #43, Chester, MD 21619
    1/50
    Active

    $600,000

    2 Beds3 Baths1,832 SqFt

    1000 HERONS NEST WAY #43, Chester, MD 21619

    MLS# MDQA2017608

    Listed by Coldwell Banker Realty

    Bright MLS (BMLS)
    115 GIBSON CIR, Chester, MD 21619
    1/42
    Price Dropped by $5K

    $569,900

    2 Beds3 Baths2,048 SqFt

    115 GIBSON CIR, Chester, MD 21619

    MLS# MDQA2017526

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
    2000 HERONS NEST WAY #401, Chester, MD 21619
    1/36
    Price Dropped by $25K

    $700,000

    3 Beds3 Baths2,602 SqFt

    2000 HERONS NEST WAY #401, Chester, MD 21619

    MLS# MDQA2017542

    Listed by Real Broker, LLC

    Bright MLS (BMLS)
    1012 AUCKLAND WAY, Chester, MD 21619
    1/46
    Active
    3D

    $599,900

    3 Beds4 Baths2,076 SqFt

    1012 AUCKLAND WAY, Chester, MD 21619

    MLS# MDQA2017452

    Listed by Redfin Corp

    Bright MLS (BMLS)
    108 CARRIAGE HEATH, Chester, MD 21619
    1/81
    Under Contract
    3D

    $1,199,000

    5 Beds4 Baths4,334 SqFt

    108 CARRIAGE HEATH, Chester, MD 21619

    MLS# MDQA2017422

    Listed by Coldwell Banker Realty

    Bright MLS (BMLS)
    232 EVELYNE ST, Chester, MD 21619
    1/35
    Price Dropped by $25K

    $840,000

    4 Beds4 Baths3,312 SqFt

    232 EVELYNE ST, Chester, MD 21619

    MLS# MDQA2017378

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    190 HARRIER WAY #21, Chester, MD 21619
    1/73
    Under Contract

    $649,900

    3 Beds3 Baths2,639 SqFt

    190 HARRIER WAY #21, Chester, MD 21619

    MLS# MDQA2017202

    Listed by The KW Collective

    Bright MLS (BMLS)
    54F QUEEN CAROLINE CT, Chester, MD 21619
    1/46
    Price Dropped by $15K

    $359,900

    3 Beds3 Baths1,440 SqFt

    54F QUEEN CAROLINE CT, Chester, MD 21619

    MLS# MDQA2017082

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
    126 WATERMANS COVE LN, Chester, MD 21619
    1/44
    Price Dropped by $20K
    3D

    $559,000

    3 Beds3 Baths1,536 SqFt

    126 WATERMANS COVE LN, Chester, MD 21619

    MLS# MDQA2016908

    Listed by Coldwell Banker Realty

    Bright MLS (BMLS)
    233 KINGFISHER LN, Chester, MD 21619
    1/84
    Price Dropped by $46K

    $999,000

    5 Beds5 Baths3,225 SqFt

    233 KINGFISHER LN, Chester, MD 21619

    MLS# MDQA2016936

    Listed by Samson Properties

    Bright MLS (BMLS)
    111 MARSHGRASS WAY #21, Chester, MD 21619
    1/57
    Active

    $680,000

    3 Beds3 Baths2,602 SqFt

    111 MARSHGRASS WAY #21, Chester, MD 21619

    MLS# MDQA2016714

    Listed by Samson Properties

    Bright MLS (BMLS)
    215 KINGFISHER LN, Chester, MD 21619
    1/44
    Price Dropped by $50K

    $1,049,500

    5 Beds5 Baths3,225 SqFt

    215 KINGFISHER LN, Chester, MD 21619

    MLS# MDQA2016702

    Listed by RE/MAX Executive

    Bright MLS (BMLS)
    2008 BRIDGEPOINTE DR, Chester, MD 21619
    1/38
    Price Dropped by $6K

    $369,000

    2 Beds2 Baths1,804 SqFt

    2008 BRIDGEPOINTE DR, Chester, MD 21619

    MLS# MDQA2016728

    Listed by RE/MAX Executive

    Bright MLS (BMLS)
    1000 HERONS NEST WAY #22, Chester, MD 21619
    1/56
    Price Dropped by $3K

    $485,000

    2 Beds3 Baths1,900 SqFt

    1000 HERONS NEST WAY #22, Chester, MD 21619

    MLS# MDQA2016820

    Listed by RE/MAX Executive

    Bright MLS (BMLS)
    34-E QUEEN ANNE WAY, Chester, MD 21619
    1/52
    Price Dropped by $14K

    $515,000

    2 Beds3 Baths1,586 SqFt

    34-E QUEEN ANNE WAY, Chester, MD 21619

    MLS# MDQA2016464

    Listed by Taylor Properties

    Bright MLS (BMLS)
    • 1
    • 2

    explore listings near Chester

    • Open House
    • Price Reduced
    • Virtual Tour
    • 3D Tour
    Bayside Logo . PNG

    Get My App

    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD, 21663, USA
        Home
        Buy
        1. All Listings
        2. Featured Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Rent
        1. Rental Listings
        Featured Areas
        1. Easton Overview
        2. Denton Overview
        3. Trappe Overview
        4. Chestertown Overview
        5. Saint Michaels Overview
        6. Ridgely Overview
        7. Berlin Overview
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
        Market Snapshot
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    Bayside Logo . PNG

    Get My App

    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD, 21663, USA
        Home
        Buy
        1. All Listings
        2. Featured Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Rent
        1. Rental Listings
        Featured Areas
        1. Easton Overview
        2. Denton Overview
        3. Trappe Overview
        4. Chestertown Overview
        5. Saint Michaels Overview
        6. Ridgely Overview
        7. Berlin Overview
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
        Market Snapshot
    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility