5,185

Chester, MD Homes

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  • /44

    $949,990 Pending

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

    110 Warbler Way Unit 3034, Chester, MD 21619

    The Severn combines an open floorplan with thoughtful design elements, with a projected settlement date of November 2026. Designed for comfortable and modern living, this home features 3 bedrooms, 2.5 baths, and a 1-car garage. The owner’s suite includes a sitting room, large walk-in closets, and a spa-inspired bath with a shower featuring a seat and handheld shower wand, double sinks, and quartz

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3034, Chester, MD 21619
  • /56

    $714,900 Sold Apr 28, 2025

    212 Switchgrass Way Unit 1644, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2024

    Last Sold Summary

    • $275/SF
    • 74 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    212 Switchgrass Way Unit 1644, Chester, MD 21619
    • /64

      Est $632,402 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

      • 2% Above List Price
      • $200/SF
      • 37 Days On Market

      Last Sold Price $620,000

      Last Listing Agent Darlene Winegardner RE/MAX

  • /49

    $1,400,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    117 Flycatcher Way, Chester, MD 21619

    The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio

    Mary Anne Kowalewski KOVO Realty

    117 Flycatcher Way, Chester, MD 21619
  • /34

    $700,000 Sold Dec 04, 2025

    245 Peregrine Dr, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft
    • Built 2024

    Last Sold Summary

    • $222/SF
    • 95 Days On Market

    Last Listing Agent Brandi Bradshaw Keller Williams Select Realtors of Annapolis

    245 Peregrine Dr, Chester, MD 21619
    • /64

      Est $538,354 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

      • 8% Below List Price
      • $283/SF
      • 3 Days On Market

      Last Sold Price $587,500

      Last Listing Agent Brandon Golueke Monument Sotheby's International Realty

  • /50

    $295,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    6 G Queen Victoria Way, Chester, MD 21619

    Price Improvement!! Marina-front and perfectly sized for easy living or a weekend escape. This one-bedroom one-bath condo offers approximately 724 square feet with an open floor plan and a geourgous view. Walk into a bright living area that flows seemlessly into the adjacent kitchen, creating an inviting and functional space for everyday living or entertaining. The kitchen has been updated with

    Julia Stevens Realty Navigator

    6 G Queen Victoria Way, Chester, MD 21619
  • /43

    $595,000 Sold Jul 28, 2025

    1614 Postal Rd, Chester, MD 21619

    • 5 Beds
    • 2.5 Baths
    • 2,656 Sq Ft
    • Built 2003

    Last Sold Summary

    • $224/SF
    • 59 Days On Market

    Current Estimated Value $594,898

    Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

    1614 Postal Rd, Chester, MD 21619
    • /54

      Est $450,005 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

      • $213/SF
      • 53 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Crystal Smith RE/MAX

  • /68

    $699,000 Open Sat 10AM - 12PM

    • 2 Beds
    • 2 Baths
    • 2,025 Sq Ft

    249 Warbler Way, Chester, MD 21619

    No waiting on the Builder here! This almost brand new Jenkins II Model was built just last year and boasts soaring, coffered and vaulted ceilings in the 2,025 sf of spaciousness! The generously sized primary suite & spa like bath with a huge walk-in-closet, double vanities & walk-in-shower is sure to make you feel like Royalty! The 2nd bedroom & full bathroom are located across the home which

    Pamela Ackermann-Doll RE/MAX Executive

    249 Warbler Way, Chester, MD 21619
  • /22

    $714,900 Sold Nov 03, 2025

    621 Warbler Way, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $359/SF
    • 9 Days On Market

    K. Hovnanian Homes K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series

    621 Warbler Way, Chester, MD 21619
    • /23

      Est $284,468 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

      • 3% Above List Price
      • $262/SF
      • 0 Days On Market

      Last Sold Price $274,900

      Last Listing Agent Crystal Smith RE/MAX

  • /19

    $989,990 New Construction

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

    110 Boatswain Way Unit 44, Chester, MD 21619

    Open-concept kitchen, dining area, & great room designed for effortless flow. Gourmet kitchen with ample cabinetry for streamlined storage & prep. Dry bar creates a dedicated space for serving & display. Fireplace adds warmth & character to the great room. Owner’s suite with sitting room, walk-in closet & private bath. Frameless shower door delivers a sleek, spa-like touch in the owner’s bath.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 44, Chester, MD 21619
  • /56

    $837,000 Sold Sep 30, 2025

    223 Broadwater Dr, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,745 Sq Ft
    • Built 2022

    Last Sold Summary

    • $305/SF
    • 11 Days On Market

    Current Estimated Value $842,918

    Last Listing Agent Ralph Kennedy RE/MAX Executive

    223 Broadwater Dr, Chester, MD 21619
    • /46

      Est $645,678 Not Listed For Sale

      105 Barren Ridge Rd, Chester, MD 21619

      • 4 Beds
      • 4.5 Baths
      • 3,016 Sq Ft
      • Built 1995
      105 Barren Ridge Rd, Chester, MD 21619

      Last Sold Summary

      • 1% Below List Price
      • $215/SF
      • 35 Days On Market

      Last Sold Price $649,000

      Last Listing Agent Suzanne Hitt Coldwell Banker Waterman Realty

  • /24

    $1,389,667 New Construction

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    123 Flycatcher Way, Chester, MD 21619

    Well-equipped kitchen with stacked dark stained cabinetry & glass uppers. Cozy fireplace adds warmth & character to spacious great room. Tranquil primary suite with generous walk-in closet. Productive home office for studying or reading. Private Extra Suite, great for overnight guests. Inviting screened patio for outdoor entertaining. Second floor loft provide addtionial living space.

    K. Hovnanian Homes Builder
    123 Flycatcher Way, Chester, MD 21619
  • /37

    $382,000 Sold Mar 20, 2026

    2644 Cecil Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,108 Sq Ft
    • Built 1983

    Last Sold Summary

    • 1% Above List Price
    • $345/SF
    • 19 Days On Market

    Current Estimated Value $362,615

    Last Listing Agent Julia Stevens Realty Navigator

    2644 Cecil Dr, Chester, MD 21619
    • /60

      Est $541,316 Not Listed For Sale

      1006 Auckland Way, Chester, MD 21619

      • 4 Beds
      • 4 Baths
      • 2,076 Sq Ft
      • Built 2001
      1006 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 8% Below List Price
      • $284/SF

      Last Sold Price $590,000

      Last Listing Agent Deborah Savoie Long & Foster

  • /52

    $699,990 New Construction

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

    110 Warbler Way Unit 3033, Chester, MD 21619

    The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 baths, and a 1-car garage. The main living area is anchored by an electric fireplace, while a dry bar adds both function and style for entertaining. A dedicated home office with lighted French doors provides a flexible space

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3033, Chester, MD 21619
  • /58

    $768,900 Sold Nov 24, 2025

    201 Switchgrass Way Unit 1442, 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 1442, Chester, MD 21619
    • /39

      Est $526,696 Not Listed For Sale

      1905 Roberta Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,100 Sq Ft
      • Built 1976
      1905 Roberta Dr, Chester, MD 21619

      Last Sold Summary

      • 11% Below List Price
      • $283/SF
      • 23 Days On Market

      Last Sold Price $594,000

      Last Listing Agent Tammi Clark Clark & Co Realty, LLC

  • /40

    $899,990 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    110 Kinglet Ct, Chester, MD 21619

    The Tuscaloosa home offers a thoughtfully designed layout with elevated finishes throughout, with a projected settlement of April 2026. Featuring 2 bedrooms, 2.5 baths, and a 3-car garage, this home blends everyday functionality with timeless style. Standout features include a dedicated home office, a screened patio perfect for outdoor relaxation, and a shiplap-accented fireplace paired with

    Mary Anne Kowalewski KOVO Realty

    110 Kinglet Ct, Chester, MD 21619
  • /60

    $355,000 Sold Aug 28, 2025

    35 F Queen Anne Way, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Built 1994

    Last Sold Summary

    • $247/SF
    • 52 Days On Market

    Last Listing Agent Lawrence Doyle Long & Foster Real Estate, Inc.

    35 F Queen Anne Way, Chester, MD 21619
    • /3

      Est $514,137 Not Listed For Sale

      106 Logan Ct, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,242 Sq Ft
      • Built 2001
      106 Logan Ct, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $223/SF
      • 0 Days On Market

      Last Sold Price $499,900

      Last Listing Agent Kay Gatling Long & Foster

  • /26

    $674,900 Pending

    • 4 Beds
    • 2.5 Baths

    Lot 6 Norman Ct, Chester, MD 21619

    The Windermere combines all of the home design elements our purchasers love the most. On the main level is an open plan design with a huge kitchen, breakfast/sunroom and family room! Formal living and dining rooms, and two-story foyer complete the space. Upstairs you will find 4 spacious bedrooms to include an owner's suite with spacious walk-in closet or choose the optional super bath and get

    George Bailey Keller Williams Flagship

    Lot 6 Norman Ct, Chester, MD 21619
  • /38

    $795,000 Sold Dec 10, 2025

    104 Woods Rd, Chester, MD 21619

    • 5 Beds
    • 3.5 Baths
    • 3,065 Sq Ft
    • Built 2002

    Last Sold Summary

    • $259/SF
    • 95 Days On Market

    Current Estimated Value $789,684

    Last Listing Agent Temple Peirce Cummings & Co. Realtors

    104 Woods Rd, Chester, MD 21619
    • /46

      Est $347,273 Not Listed For Sale

      604 Dominion Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1897
      604 Dominion Rd, Chester, MD 21619

      Last Sold Summary

      • 7% Above List Price
      • $226/SF
      • 37 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Barry Hess Keller Williams Flagship

  • /66

    $539,000

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

    3000 Herons Nest Way Unit 11, Chester, MD 21619

    A price improvement has been made with an additional seller paid $5,000.00 closing assistance to a qualified buyer's settlement fees. This unit has approximately $55,000.00 in upgrades and shows like a model home. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of

    John Freeman Coldwell Banker Realty

    3000 Herons Nest Way Unit 11, Chester, MD 21619
  • /68

    $1,200,000 Sold Sep 30, 2025

    1622 Bayside Dr, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • Built 2009

    Last Sold Summary

    • $400/SF
    • 112 Days On Market

    Current Estimated Value $1,195,392

    Last Listing Agent Cynthia Sullivan Sullivan Select, LLC.

    1622 Bayside Dr, Chester, MD 21619
    • /21

      Est $405,746 Not Listed For Sale

      1926 Sherman Dr, Chester, MD 21619

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1991
      1926 Sherman Dr, Chester, MD 21619

      Last Sold Summary

      • 2% Below List Price
      • $266/SF
      • 97 Days On Market

      Last Sold Price $415,000

      Last Listing Agent Michael Rosendale Rosendale Realty

  • /18

    $465,000 Under Contract

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    15 Queen Anne Way Unit E, Chester, MD 21619

    PRICE DROP! Motivated Seller! Escape to the water — without the waterfront price. This Chester River–front townhome in Queens Landing is the perfect second home or low-maintenance retreat, all for under $500K. Enjoy sunrise water views from your private patio and balcony, and lock-and-leave peace of mind when you head back home. Inside, the layout is easy and functional with luxury vinyl plank

    Jennifer Thomas RE/MAX Executive

    15 Queen Anne Way Unit E, Chester, MD 21619
  • /27

    $340,000 Sold Jul 31, 2025

    15G Queen Anne Way, Chester, MD 21619

    • 2 Beds
    • 1.5 Baths
    • 1,104 Sq Ft
    • Built 1983

    Last Sold Summary

    • $308/SF
    • 34 Days On Market

    Current Estimated Value $346,746

    Last Listing Agent Mackenzie Hoffer CENTURY 21 New Millennium

    15G Queen Anne Way, Chester, MD 21619
    • /67

      Est $529,707 Not Listed For Sale

      910 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,100 Sq Ft
      • Built 2001
      910 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 5% Below List Price
      • $267/SF
      • 2 Days On Market

      Last Sold Price $560,000

      Last Listing Agent Ryan Lancaster Long & Foster

  • /16

    $883,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,601 Sq Ft

    Munich ESP Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Extra Suite Plus for multi-generational living. Striking kitchen with large center island and corner pantry. Spacious great room with tons of windows for natural sun light. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities and optional freestanding tub. Private home office off foyer for working from home. Large covered patio for enjoying the outdoors.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
  • /36

    $490,000 Sold Feb 19, 2026

    906 Auckland Way, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 2,076 Sq Ft
    • Built 2001

    Last Sold Summary

    • $236/SF
    • 74 Days On Market

    Current Estimated Value $503,341

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    906 Auckland Way, Chester, MD 21619
    • /45

      Est $498,027 Not Listed For Sale

      204 Schooner Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,076 Sq Ft
      • Built 1996
      204 Schooner Way, Chester, MD 21619

      Last Sold Summary

      • 8% Above List Price
      • $222/SF
      • 81 Days On Market

      Last Sold Price $460,000

      Last Listing Agent Branden Schroeder GybeSet Homes

  • /45

    $825,000 Sold Dec 09, 2025

    124 Nauset Ln, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,583 Sq Ft
    • Built 2021

    Last Sold Summary

    • $319/SF
    • 87 Days On Market

    Current Estimated Value $817,840

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    124 Nauset Ln, Chester, MD 21619
    • /23

      Est $407,807 Not Listed For Sale

      2608 Harrington Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1967
      2608 Harrington Rd, Chester, MD 21619

      Last Sold Summary

      • 16% Above List Price
      • $224/SF
      • 71 Days On Market

      Last Sold Price $351,000

      Last Listing Agent Brenda Sarver Maryland Realty Connection

  • /51

    $884,900 Sold May 23, 2025

    148 Nighthawk Dr, Stevensville, MD 21666

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft
    • Built 2024

    Last Sold Summary

    • $319/SF
    • 5 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    148 Nighthawk Dr, Stevensville, MD 21666
    • /30

      Est $557,757 Not Listed For Sale

      230 Cross Creek Ct, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,332 Sq Ft
      • Built 1999
      230 Cross Creek Ct, Chester, MD 21619

      Last Sold Summary

      • 3% Below List Price
      • $247/SF
      • 19 Days On Market

      Last Sold Price $575,000

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

Showing Results 321 - 360, Page 9 of 18

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