17

Chester, MD Homes for Sale under $500,000

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  • 170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    /71

    $499,000

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

    170 Harrier Way Unit 11, Chester, MD 21619

    Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent Island! Completely move-in ready, this home boasts a gourmet kitchen, a formal dining area, and a cozy family room, all enhanced by luxurious finishes throughout.The spacious primary bedroom features a full ensuite bath,

    Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
  • 54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    /43

    $415,000

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54A Queen Caroline Ct, Chester, MD 21619

    Price Improvement...End Unit in Sought-After Queens Landing – A Waterfront Lifestyle Awaits!Don’t miss this spacious end unit in the highly desirable Queens Landing community! Featuring two primary bedroom suites with private baths, this home offers the perfect blend of comfort and functionality. The expansive kitchen is a chef’s dream, boasting granite countertops, stainless steel

    Darlene Winegardner RE/MAX Executive

    54A Queen Caroline Ct, Chester, MD 21619
  • 1839 Harbor Dr, Chester, MD 21619
    1839 Harbor Dr, Chester, MD 21619
    1839 Harbor Dr, Chester, MD 21619
    /23

    $405,000

    • 4 Beds
    • 2 Baths
    • 2,035 Sq Ft

    1839 Harbor Dr, Chester, MD 21619

    Opportunity Knocks!Welcome to Harbor View on Kent Island - Just 7 minutes from the Bay BridgeThis oversized ranch style home boasts 4 Bedrooms and 2 Full baths and is located just one block from Cox Creek. The open concept floor plan features a formal living room, large main level bedroom, hardwood flooring throughout, a modern kitchen with ample cabinetry, center island, extra counter

    Greg Koch Taylor Properties

    1839 Harbor Dr, Chester, MD 21619
  • 1903 Churchhill Ln, Chester, MD 21619
    1903 Churchhill Ln, Chester, MD 21619
    1903 Churchhill Ln, Chester, MD 21619
    /41

    $434,900

    • 4 Beds
    • 3 Baths
    • 1,682 Sq Ft

    1903 Churchhill Ln, Chester, MD 21619

    Welcome Home to 1903 Churchhill Lane! This Beautifully updated Rancher offers the space you need to create a life you desire. Boasting an array of sleek finishes throughout this 4 Bedroom, 3 Bathroom home has so much to offer!! When you walk inside you'll find an open concept layout featuring spacious living room, kitchen, family room, 4 entry level bedrooms, 3 full bathrooms, laundry room and

    Lois Alberti Alberti Realty, LLC

    1903 Churchhill Ln, Chester, MD 21619
  • 1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    /33

    $469,000

    • 2 Beds
    • 2 Baths
    • 1,444 Sq Ft

    1401 Calvert Rd, Chester, MD 21619

    Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - PRICE REDUCED - All on one level - Beautifully landscaped 3/4 acre lot that backs to trees - fenced patio area - 2 bedrooms with lots of windows and large closets - 2 full beths, one with a tub, one with a walkin shower - fabulous sunroom addition - quiet office area - updated kitchen with granite counters, newer

    Suzanne Hitt Coldwell Banker Waterman Realty

    1401 Calvert Rd, Chester, MD 21619
  • 108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    /49

    $499,900

    • 3 Beds
    • 2.5 Baths
    • 1,791 Sq Ft

    108 Bodys Neck Rd, Chester, MD 21619

    Resort-Style Island Living with Unmatched Water Views!Discover the perfect blend of coastal charm and modern luxury in this rarely available, oversized end-unit townhome Perfectly positioned to capture water views and marina, this meticulously updated 3-bedroom, 2.5-bath home offers a true resort-style experience in one of the Eastern Shore’s most desirable locations.Step inside

    Bill Longest Realty Navigator

    108 Bodys Neck Rd, Chester, MD 21619
  • 9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    /48

    $425,000

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

    9B Queen Victoria Way, Chester, MD 21619

    This 1680 sq ft , 2 1/2 story townhome & this community have it all! It features many updates within the last year, and it shows beautifully! It is "move-in ready",!.. The updates include a new main-level half bath & a new full bathroom on the top level, both have new flooring, ADA-compliant toilets, new vanity/sink & faucets, and paint. Interior doors are 6 panel colonial replaced in

    Melanie Mcknight RE/MAX Professionals

    9B Queen Victoria Way, Chester, MD 21619
  • 1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    /24

    $455,000

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft

    1872 Harbor Dr, Chester, MD 21619

    1872 Harbor Drive, Chester, MDHarbor View Community | Corner Lot | Renovated Rancher with Room to GrowWelcome to 1872 Harbor Drive in the Harbor View neighborhood of Chester, Maryland—a move-in ready ranch-style home that offers the space and updates today’s buyers are searching for. Located in the Matapeake Elementary School district, this home sits on a rare double corner lot with

    Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • 312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    /39

    $479,000

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    312 Blenny Ln, Chester, MD 21619

    You do not want to miss this opportunity to enjoy island living in this maintenance free, WATER VIEW-End UNIT! Come enjoy island living in the Bayside Community. Offering POND views from every window in this sought after end unit home complete with beautiful landscaping. Relax on your spacious deck overlooking the pond complete with 2 fountains or invite family and friends to enjoy a cookout

    Judith Brown Samson Properties

    312 Blenny Ln, Chester, MD 21619
  • 34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    /57

    $469,000

    • 2 Beds
    • 2.5 Baths
    • 1,104 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water-privileged resort-style community of Queen's Landing, along the scenic Chester River and Macum Creek off the Chesapeake Bay. Step into the light-filled foyer and head up the stairs to the main level, you will find this lovely 2 bedroom, 2.5 bath condominium is move in ready. Just bring your patio chairs,

    Lona Todd Taylor Properties

    34 Queen Anne Way, Chester, MD 21619
  • 15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    /68

    $499,000

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

    15 Queen Anne Way Unit E, Chester, MD 21619

    The BIGGEST price drop yet!! Wake up to shimmering Chester River views and let every day feel like a getaway!This beautifully maintained 2.5-level townhome offers 1,680 square feet of stylish and functional living space in the sought-after waterfront community of Queens Landing. The main level features a cozy living area with a gas fireplace, luxury vinyl plank flooring, and access to a

    Julia Stevens Realty Navigator

    15 Queen Anne Way Unit E, Chester, MD 21619
  • 1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    /26

    $499,000

    • 2 Beds
    • 2 Baths

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Priced to Sell! Seller is ready for their next adventure! Move in, in May! Enjoy low-maintenance living in the amenity-rich, 55+ community of Four Seasons on Kent Island. This 2-bedroom, 2-bath home offers comfortable one-level living with an open layout, perfect for entertaining or relaxing. The property includes a 1-car garage with additional storage units—ideal for keeping your home organized

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • 1000 Herons Nest Way Unit 22, Chester, MD 21619
    1000 Herons Nest Way Unit 22, Chester, MD 21619
    1000 Herons Nest Way Unit 22, Chester, MD 21619
    /59

    $488,000

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

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. With 1900 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, Chester, MD 21619
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /34

    $455,000

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    807 Auckland Way, Chester, MD 21619

    PRICE REDUCED! Waterside Living on Kent Island! Discover the perfect blend of comfort and convenience in this spacious 3-bedroom, 3.5-bathroom condo located on Kent Island, in the Bayside Condominiums waterside community. This 3-level condo offers a wonderful combination of space, style, and serene coastal living.The open-concept main floor features a freshly painted, inviting living

    Andrew Spagnolo Samson Properties

    807 Auckland Way, Chester, MD 21619
  • 1340 Queen Anne Dr, Chester, MD 21619
    1340 Queen Anne Dr, Chester, MD 21619
    1340 Queen Anne Dr, Chester, MD 21619
    /27

    $464,900

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1340 Queen Anne Dr, Chester, MD 21619

    Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • 306 Hanna Ct, Chester, MD 21619
    306 Hanna Ct, Chester, MD 21619
    306 Hanna Ct, Chester, MD 21619
    /3

    $469,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 1,828 Sq Ft

    306 Hanna Ct, Chester, MD 21619

    Nestled in a quiet and serene community surrounded by mature trees, this 4 bedroom, 2.5 bath home is the definition of move in ready. With updates spanning from top to bottom, There is nothing left to do but settle in and enjoy your gorgeous new screened-in porch while soaking up the peaceful surroundings. Inside, you will love the stylishly remodeled kitchen, new air conditioner, and luxury

    Terri Murray RE/MAX Executive

    306 Hanna Ct, Chester, MD 21619
  • 129 Kirwans Landing Ln, Chester, MD 21619
    129 Kirwans Landing Ln, Chester, MD 21619
    129 Kirwans Landing Ln, Chester, MD 21619
    /124

    $450,000 Open Fri 4PM - 6PM

    • 4 Beds
    • 2.5 Baths
    • 2,630 Sq Ft

    129 Kirwans Landing Ln, Chester, MD 21619

    **List price is opening bid only** In cooperation with Alex Cooper Auctioneers, this property shall be auctioned at 11 am on 10/16/25; on line bidding to begin on 10/11/25* See auctioneer's website for full details!Peaceful Coastal Living in One of Kent Island’s Most Sought-After Communities!Tucked away on 1.01 beautifully landscaped acres, this four bedroom, two full and one half bath

    Noah Mumaw Monument Sotheby's International Realty

    129 Kirwans Landing Ln, Chester, MD 21619
Maryland Queen Annes County Chester

Real Estate & Homes in Chester, MD under $500,000

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 44 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, MD over the last 12 months is $602,400, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$602,400
Median Single Family Sale Price
$649,000
Median Townhouse Sale Price
$420,000
Median 2 Bedroom Sale Price
$537,400
Median 1 Bedroom Sale Price
$306,500
Average Price Per Sq Ft
$291
Number of Homes for Sale
70
Last 12 months Home Sales
188
Months of Supply
4.50
Median List Price
$595,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 17 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Chester, MD and find the perfect fit for your homeownership goals.

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