5,224

Homes in ZIP Code 21619

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    • /27

      Est $343,688

      Not Listed For Sale

      15G Queen Anne Way, Chester, MD 21619

      • 2 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1983
      15G Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Mackenzie Hoffer CENTURY 21 New Millennium

  • /47

    $819,990

    New Construction $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 2933, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces.The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2933, Chester, MD 21619
  • /24

    $849,990

    Sold May 01, 2026

    110 Boatswain Way Unit 31, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 10% Below List Price
    • $327/SF
    • 44 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    110 Boatswain Way Unit 31, Chester, MD 21619
    • /45

      Est $693,128

      Not Listed For Sale

      106 Woods Rd, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,551 Sq Ft
      • Built 2000
      106 Woods Rd, Chester, MD 21619

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Jackie Ball Daley Northrop Realty

  • /41

    $835,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    201 Switchgrass Way Unit 34, Chester, MD 21619

    Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance

    Brad Kappel TTR Sotheby's International Realty

    201 Switchgrass Way Unit 34, Chester, MD 21619
  • /66

    $330,000

    Sold Sep 16, 2025

    208 Ringneck Ct, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,747 Sq Ft
    • Built 1995

    Last Sold Summary

    • $189/SF
    • 98 Days On Market

    Current Estimated Value $330,622

    Last Listing Agent Phyllis Endrich Long & Foster Real Estate, Inc.

    208 Ringneck Ct, Chester, MD 21619
    • /39

      Est $355,431

      Not Listed For Sale

      7003 Bridgepointe Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,302 Sq Ft
      • Built 1994
      7003 Bridgepointe Dr, Chester, MD 21619

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent April Heim Rosendale Realty

  • /21

    $969,990

    New Construction $34K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 34, Chester, MD 21619

    Stylish gourmet kitchen centered around a large island. Dining space with convenient dry bar for hosting. Open great room featuring an electric fireplace. Balcony extending from the main living area. Owner’s suite with two spacious walk-in closets. Private sitting area in owner’s suite with balcony connection. Owner’s bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 34, Chester, MD 21619
  • /2

    $542,500

    Sold Nov 13, 2025

    558 Cross Creek Ct, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,558 Sq Ft
    • Built 2002

    Last Sold Summary

    • $212/SF
    • 121 Days On Market

    Current Estimated Value $555,220

    Last Listing Agent Thomas Hennerty NetRealtyNow.com, LLC

    558 Cross Creek Ct, Chester, MD 21619
    • /22

      Est $387,327

      Not Listed For Sale

      500 Dominion Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2000
      500 Dominion Rd, Chester, MD 21619

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Kelly Alvarez Pugliese Metas Realty Group, LLC

  • /45

    $499,000

    $41K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,979 Sq Ft

    124 Riverside Dr, Chester, MD 21619

    NEW PRICE—An Unbelievable Value on Kent Island! Built in 2020, this gorgeous, like-new home offers approximately 1,974 square feet of beautifully maintained living space, a spacious yard backing to trees, and a desirable Kent Island location. An assumable VA loan at an attractive 2.75% interest rate may be available to qualified buyers, subject to lender and VA approval.Fresh interior

    Christine Schumaker Douglas Realty LLC

    124 Riverside Dr, Chester, MD 21619
  • /61

    $668,500

    Sold Mar 31, 2026

    141 Switchgrass Way Unit 34, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft
    • Built 2022

    Last Sold Summary

    • $257/SF
    • 108 Days On Market

    Current Estimated Value $664,236

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
    • /43

      Est $547,434

      Not Listed For Sale

      1303 Saint Marys Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,970 Sq Ft
      • Built 1964
      1303 Saint Marys Rd, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Deborah Shiley Long & Foster Real Estate, Inc.

  • /54

    $619,990

    New Construction $10K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    110 Boatswain Way Unit 3012, Chester, MD 21619

    Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern comfort with functional living spaces.The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    110 Boatswain Way Unit 3012, Chester, MD 21619
  • /20

    $1,069,990

    Sold Jun 25, 2026

    102 Boatswain Way Unit 44, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $411/SF
    • 35 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    102 Boatswain Way Unit 44, Chester, MD 21619
    • /43

      Est $415,906

      Not Listed For Sale

      510 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,899 Sq Ft
      • Built 2001
      510 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /32

    $374,900

    $8K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    2004 Bridgepointe Dr, Chester, MD 21619

    ALL NEW Carpet & flooring, fresh custom paint, Granite countertops and Newer Appliances! Welcome to one of the most desirable homes in the Bridgepointe community! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of the community's most sought after amenities...

    Sheryl Carmody RE/MAX Executive

    2004 Bridgepointe Dr, Chester, MD 21619
  • /19

    $714,990

    Sold Dec 24, 2025

    630 Warbler Way Unit 24, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $275/SF
    • 28 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    630 Warbler Way Unit 24, Chester, MD 21619
    • /33

      Est $492,818

      Not Listed For Sale

      1852 Harbor Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,238 Sq Ft
      • Built 1953
      1852 Harbor Dr, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Suzanne Hitt Coldwell Banker Waterman Realty

  • /35

    $819,990

    New Construction $45K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 32, Chester, MD 21619

    Elegant gourmet kitchen with designer cabinetry & center island.Spacious great room featuring electric fireplace.Charming dining area with dry bar for efficient serving.Serene owner's suite & spa bath with frameless shower door.Convenient home office for working remotely.Peaceful balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 32, Chester, MD 21619
  • /45

    $625,000

    Sold Feb 23, 2026

    154 Harrier Way, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 2023

    Last Sold Summary

    • $329/SF
    • 317 Days On Market

    Current Estimated Value $635,064

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
    • /12

      Est $376,128

      Not Listed For Sale

      1303 Calvert Rd, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1955
      1303 Calvert Rd, Chester, MD 21619

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent susan taylor Chaney Homes, LLC

  • /11

    $709,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    Kelly Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private home office for working from home.Spacious great room with slider to covered patio.Beautiful kitchen with large island and roomy pantry.Luxurious primary suite with triple windows.Relaxing primary bath with spacious shower and walk-in closet.Convenient covered patio with screen patio option.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
  • /58

    $769,900

    Sold Nov 25, 2025

    201 Switchgrass Way Unit 1443, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Last Sold Summary

    • $405/SF
    • 53 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1443, Chester, MD 21619
    • /48

      Est $324,341

      Not Listed For Sale

      1905 Cecil Ct, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 1,108 Sq Ft
      • Built 1983
      1905 Cecil Ct, Chester, MD 21619

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Chris Craddock EXP Realty, LLC

  • /77

    $1,250,000

    Open Thu 5PM - 7PM
    • 3 Beds
    • 2.5 Baths
    • 2,742 Sq Ft

    1717 Harbor Dr, Chester, MD 21619

    Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality.Inside, you'll

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    1717 Harbor Dr, Chester, MD 21619
  • /12

    $1,510,604

    Sold Aug 06, 2026

    216 Kingfisher Ln, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $752/SF
    • 9,714 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    216 Kingfisher Ln, Chester, MD 21619
    • /53

      Est $449,588

      Not Listed For Sale

      205 Newtown Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1992
      205 Newtown Rd, Chester, MD 21619

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Teresa Klopfer RE/MAX Realty Group

  • /32

    $949,990

    New Construction $25K PRICE DROP Pending
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    323 Kingfisher Ln, Chester, MD 21619

    Welcome to the Tuscaloosa, a beautifully designed home that blends an open-concept floorplan with warm Farmhouse-inspired style, creating the perfect balance of comfort and functionality. Projected for November 2026 settlement, this spacious home features 5 bedrooms, 4.5 bathrooms, and a 3-car garage, offering plenty of room for everyday living, entertaining, and hosting overnight

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    323 Kingfisher Ln, Chester, MD 21619
  • /29

    $326,000

    Sold May 05, 2026

    204 Ringneck Ct, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 1,747 Sq Ft
    • Built 1995

    Last Sold Summary

    • 6% Below List Price
    • $187/SF
    • 68 Days On Market

    Current Estimated Value $329,656

    Last Listing Agent Mary Wagner Cummings & Co. Realtors

    204 Ringneck Ct, Chester, MD 21619
    • /65

      Est $315,036

      Not Listed For Sale

      53B Queen Caroline Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,280 Sq Ft
      • Built 1998
      53B Queen Caroline Ct, Chester, MD 21619

      Last Sold Summary

      • 118 Days On Market

      Last Listing Agent Julia Stevens Realty Navigator

  • /63

    $724,999

    Open Sat 10AM - 1PM $25K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    233 Peregrine Dr, Chester, MD 21619

    Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel

    Michelle Abplanalp Rosendale Realty

    233 Peregrine Dr, Chester, MD 21619
  • /2

    $643,000

    Sold Apr 08, 2026

    219 Broadwater Dr, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,913 Sq Ft
    • Built 2023

    Last Sold Summary

    • 1% Below List Price
    • $336/SF
    • 3 Days On Market

    Current Estimated Value $648,808

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    219 Broadwater Dr, Chester, MD 21619
    • /35

      Est $544,244

      Not Listed For Sale

      511 Skipper Ct, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,754 Sq Ft
      • Built 1972
      511 Skipper Ct, Chester, MD 21619

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Julie Hall Sellers Choice Real Estate, LLC.

  • /2

    $789,000

    Coming Soon Sep 17
    • 3 Beds
    • 2.5 Baths
    • 2,787 Sq Ft

    402 Macum Creek Dr, Chester, MD 21619

    Professional Photos Coming Soon!Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting

    Tara Trout Samson Properties

    402 Macum Creek Dr, Chester, MD 21619
  • /2

    $750,000

    Sold Mar 06, 2026

    113 Kirwans Landing Ln, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • $350/SF

    Current Estimated Value $761,873

    Last Listing Agent Mary Lynch Cummings & Co. Realtors

    113 Kirwans Landing Ln, Chester, MD 21619
    • /53

      Est $375,478

      Not Listed For Sale

      102 Ringneck Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,747 Sq Ft
      • Built 1995
      102 Ringneck Ct, Chester, MD 21619

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • /61

    $1,290,000

    $60K PRICE DROP Under Contract
    • 5 Beds
    • 2 Baths
    • 2,700 Sq Ft

    2513 Cecil Dr, Chester, MD 21619

    Waterfront homes are common on Kent Island. Waterfront acreage is not. The difference is the land -- and at 1.65 acres with 205 feet of protected shoreline, this property belongs in a conversation with the finest waterfront offerings on Kent Island, not the most common. Waterfront properties with this combination of acreage, waterfront footage, and finishes are rare at this price

    David Moore Real Broker, LLC

    2513 Cecil Dr, Chester, MD 21619
  • /54

    $570,000

    Sold Jun 19, 2026

    1000 Herons Nest Way Unit 402, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2020

    Last Sold Summary

    • 5% Below List Price
    • $300/SF
    • 42 Days On Market

    Last Listing Agent Dan Judge RE/MAX United Real Estate

    1000 Herons Nest Way Unit 402, Chester, MD 21619
    • /27

      Est $339,064

      Not Listed For Sale

      1304 Little Creek Rd, Chester, MD 21619

      • 2 Beds
      • 1 Bath
      • 912 Sq Ft
      • Built 1979
      1304 Little Creek Rd, Chester, MD 21619

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Mark Andrews Keller Williams Select Realtors of Annapolis

Showing Results 281 - 320, Page 8 of 18

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