5,197

Chester, MD Homes

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  • /38

    $875,000 Sold May 20, 2025

    200 Harrier Way Unit 44, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • Built 2023

    Last Sold Summary

    • 23 Days On Market

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    200 Harrier Way Unit 44, Chester, MD 21619
    • /38

      Est $722,039 Not Listed For Sale

      1518 Saint Marys Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1968
      1518 Saint Marys Rd, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $350/SF
      • 189 Days On Market

      Last Sold Price $700,000

      Last Listing Agent Darlene Winegardner RE/MAX

  • /40

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    1916 Stevens Dr, Chester, MD 21619

    Come see this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a scenic 0.35-acre corner lot in the highly desirable Harbor View community, just two miles east of the Chesapeake Bay Bridge. Inside, enjoy a bright, modern kitchen with new countertops and backsplash, hardwood floors on the main and upstairs evels, and cathedral ceiling with skylights. Relax in the spacious

    Kimberly O'Connor Coldwell Banker Realty

    1916 Stevens Dr, 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 $552,506

    Last Listing Agent Thomas Hennerty NetRealtyNow.com, LLC

    558 Cross Creek Ct, Chester, MD 21619
    • /39

      Est $406,873 Not Listed For Sale

      10A Queen Elizabeth Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,380 Sq Ft
      • Built 1983
      10A Queen Elizabeth Ct, Chester, MD 21619

      Last Sold Summary

      • 7% Above List Price
      • $276/SF
      • 7 Days On Market

      Last Sold Price $381,000

      Last Listing Agent Jennifer Holden Compass

  • /48

    $644,990 Pending

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

    630 Warbler Way Unit 2233, Chester, MD 21619

    The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2233, 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 $683,760

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
    • /73

      Est $2,089,721 Not Listed For Sale

      2801 Cox Neck Rd, Chester, MD 21619

      • 3 Beds
      • 3 Baths
      • 4,297 Sq Ft
      • Built 1999
      2801 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 7% Below List Price
      • $524/SF
      • 36 Days On Market

      Last Sold Price $2,250,000

      Last Listing Agent Jimmy White Long & Foster

  • /44

    $989,990 New Construction

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

    110 Boatswain Way Unit 3044, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in November 2026, this home combines modern style with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. The owner’s suite includes a sitting room and large walk-in closets, providing a

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3044, 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 K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos

    630 Warbler Way Unit 24, Chester, MD 21619
    • /23

      Est $310,965 Not Listed For Sale

      1823 Chester Dr, Chester, MD 21619

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft
      • Built 1976
      1823 Chester Dr, Chester, MD 21619

      Last Sold Summary

      • 7% Above List Price
      • $269/SF
      • 10 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Mary Wagner Cummings & Co. Realtors

  • /21

    $1,003,673 New Construction

    • 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
  • /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 $630,424

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
    • /52

      Est $357,722 Not Listed For Sale

      37G Queen Anne Way, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,280 Sq Ft
      • Built 1994
      37G Queen Anne Way, Chester, MD 21619

      Last Sold Summary

      • 2% Above List Price
      • $275/SF
      • 42 Days On Market

      Last Sold Price $352,000

      Last Listing Agent Violeta Aguirre Long & Foster

  • /11

    $774,990 New Construction

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

    Kelly Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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
    • /38

      Est $533,583 Not Listed For Sale

      518 Cross Creek Ct, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,356 Sq Ft
      • Built 2002
      518 Cross Creek Ct, Chester, MD 21619

      Last Sold Summary

      • 1% Above List Price
      • $224/SF
      • 87 Days On Market

      Last Sold Price $527,500

      Last Listing Agent Darlene Winegardner RE/MAX

  • /52

    $979,900 Pending

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

    176 Flagstaff Way Unit 2443, Chester, MD 21619

    The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2443, Chester, MD 21619
  • /43

    $495,000 Sold Jul 31, 2025

    2614 Ellicott Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2023

    Last Sold Summary

    • $354/SF
    • 2 Days On Market

    Current Estimated Value $488,657

    Last Listing Agent Wendy Oliver Coldwell Banker Realty

    2614 Ellicott Dr, Chester, MD 21619
    • /44

      Est $548,986 Not Listed For Sale

      545 Cross Creek Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,486 Sq Ft
      • Built 2002
      545 Cross Creek Ct, Chester, MD 21619

      Last Sold Summary

      • 4% Below List Price
      • $231/SF
      • 0 Days On Market

      Last Sold Price $574,000

      Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

  • /44

    $749,990 New Construction

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

    110 Warbler Way Unit 3021, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3021, Chester, MD 21619
  • /34

    $226,000 Sold Aug 25, 2025

    602 Dominion Rd, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1900

    Last Sold Summary

    • $126/SF
    • 49 Days On Market

    Current Estimated Value $280,546

    Last Listing Agent Janice O'Donnell Chaney Homes, LLC

    602 Dominion Rd, Chester, MD 21619
    • /69

      Est $911,783 Not Listed For Sale

      2702 Sherman Dr, Chester, MD 21619

      • 5 Beds
      • 4 Baths
      • 2,752 Sq Ft
      • Built 1986
      2702 Sherman Dr, Chester, MD 21619

      Last Sold Summary

      • 9% Above List Price
      • $303/SF
      • 35 Days On Market

      Last Sold Price $835,000

      Last Listing Agent Justin Kennedy Samson Properties

  • /12

    $636,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    Bernstein II Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, Chester, MD 21619

    Elegant foyer welcoming guests to your home. Convenient single-story living. Kitchen with spacious pantry and oversized island. Open-concept great room and dining area adjacent to kitchen. Private primary suite with large walk-in closet and spa bath. Laundry room and HovHall with plenty of space to store and organize.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
  • /45

    $650,000 Sold Jun 26, 2025

    106 Woods Rd, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,551 Sq Ft
    • Built 2000

    Last Sold Summary

    • $255/SF
    • 21 Days On Market

    Current Estimated Value $664,416

    Last Listing Agent Jackie Ball Daley Northrop Realty

    106 Woods Rd, Chester, MD 21619
    • /34

      Est $384,255 Not Listed For Sale

      117 Wright Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,337 Sq Ft
      • Built 2003
      117 Wright Rd, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $278/SF
      • 47 Days On Market

      Last Sold Price $371,750

      Last Listing Agent Barry Hess Keller Williams Flagship

  • /54

    $764,900 Pending

    • 3 Beds
    • 2 Baths
    • 2,303 Sq Ft

    129 Sailcloth Way, Chester, MD 21619

    Welcome to 129 Sailcloth Way in the resort-style community of Four Seasons at Kent Island! This beautifully upgraded Kilarney model offers over 2300 square feet of single-level living, an open layout, and designer finishes throughout. Move-in ready and available now - no need to wait months for new construction.Inside, you'll find a spacious gourmet kitchen with GE Profile appliances, gas

    Catherine Watson - Bye RE/MAX Executive

    129 Sailcloth Way, Chester, MD 21619
  • /47

    $435,000 Sold Aug 04, 2025

    2707 Cox Neck Rd, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • Built 1995

    Last Sold Summary

    • $277/SF
    • 34 Days On Market

    Current Estimated Value $435,263

    Last Listing Agent Samantha Hernandez Douglas Realty, LLC

    2707 Cox Neck Rd, Chester, MD 21619
    • /64

      Est $637,589 Not Listed For Sale

      1326 Queen Anne Dr, Chester, MD 21619

      • 5 Beds
      • 3 Baths
      • 3,103 Sq Ft
      • Built 1990
      1326 Queen Anne Dr, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $200/SF
      • 37 Days On Market

      Last Sold Price $620,000

      Last Listing Agent Darlene Winegardner RE/MAX

  • /73

    $549,900 Pending

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

    630 Warbler Way Unit 2211, Chester, MD 21619

    Magothy || Available April 2026 This thoughtfully designed 2 bed, 2.5 bath home with a 1-car garage combines functionality with style. A welcoming home office with lited French doors offers the perfect space to work or study, while the electric fireplace creates a cozy focal point. Entertain with ease thanks to a convenient dry bar just steps from the kitchen. The kitchen is appointed with a gas

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2211, Chester, MD 21619
  • /44

    $295,000 Sold Jul 21, 2025

    513 Teal Ct, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Built 1996

    Last Sold Summary

    • $275/SF
    • 22 Days On Market

    Current Estimated Value $289,547

    Last Listing Agent April Heim Rosendale Realty

    513 Teal Ct, Chester, MD 21619
    • /64

      Est $530,722 Not Listed For Sale

      1014 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,076 Sq Ft
      • Built 2002
      1014 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 10% Below List Price
      • $283/SF
      • 3 Days On Market

      Last Sold Price $587,500

      Last Listing Agent Brandon Golueke Monument Sotheby's International Realty

  • /52

    $799,990 New Construction

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

    110 Boatswain Way Unit 3042, 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 October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3042, 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 $720,658

    Last Listing Agent Mary Lynch Cummings & Co. Realtors

    113 Kirwans Landing Ln, Chester, MD 21619
    • /54

      Est $444,638 Not Listed For Sale

      603 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,112 Sq Ft
      • Built 2000
      603 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 1% Below List Price
      • $213/SF
      • 53 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Crystal Smith RE/MAX

  • /37

    $310,000

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    501 Teal Ct, Chester, MD 21619

    Welcome to easy, waterfront-inspired living in the heart of Chester! This beautifully maintained first-floor condo at 501 Teal Ct offers the perfect blend of comfort, style, and convenience—plus peaceful views of the community pond right from your backyard. Step inside to find gorgeous hardwood floors flowing throughout the main living space, anchored by a cozy propane fireplace—perfect for those

    Kathleen Higginbotham Samson Properties

    501 Teal Ct, Chester, MD 21619
  • /32

    $779,900 Sold Sep 11, 2025

    121 Wheelhouse Way Unit 42, Chester, MD 21619

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

    Move in Ready Sold Summary

    • $410/SF
    • 16 Days On Market

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

    121 Wheelhouse Way Unit 42, Chester, MD 21619
    • /23

      Est $274,603 Not Listed For Sale

      216 Teal Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,050 Sq Ft
      • Built 1993
      216 Teal Ct, Chester, MD 21619

      Last Sold Summary

      • $262/SF
      • 0 Days On Market

      Last Sold Price $274,900

      Last Listing Agent Crystal Smith RE/MAX

  • /30

    $765,000 Coming Soon

    • 2 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 43, Chester, MD 21619

    Rare penthouse unit with year-round water views from multiple rooms inside and the private covered patio. Perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for ever builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the

    John Freeman Coldwell Banker Realty

    111 Marshgrass Way Unit 43, Chester, MD 21619
  • /10

    $659,990 Sold Mar 11, 2026

    176 Flagstaff Way Unit 12, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 6% Below List Price
    • $330/SF
    • 5 Days On Market

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

    176 Flagstaff Way Unit 12, Chester, MD 21619

Showing Results 281 - 320, Page 8 of 18

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