16

Chester, MD Homes for Sale under $400,000

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  • 2645 Cox Neck Rd, Chester, MD 21619
    2645 Cox Neck Rd, Chester, MD 21619
    2645 Cox Neck Rd, Chester, MD 21619
    /61

    $399,500

    Open Sat 9AM - 11AM
    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft

    2645 Cox Neck Rd, Chester, MD 21619

    Open House, Saturday, 6/27, 9:00am - 11:00am. Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre lot, this well-maintained property combines comfort, convenience, and exceptional value at $399,500. Inside, you'll find a bright and inviting floor plan featuring a kitchen with a

    Agent Photo

    Gretchen Wichlinski

    Compass

    2645 Cox Neck Rd, Chester, MD 21619
  • 3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    /9

    $269,000

    $6K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    3 D Queen Victoria Ct, Chester, MD 21619

    Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet in the bedroom. Queens Landing is a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    3 D Queen Victoria Ct, Chester, MD 21619
  • 0 Parks Rd, Chester, MD 21619
    0 Parks Rd, Chester, MD 21619
    0 Parks Rd, Chester, MD 21619
    /15

    $275,000

    $25K PRICE DROP
    • Land
    • 29,620 Sq Ft
    • $404,412 per Acre

    0 Parks Rd, Chester, MD 21619

    Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life this is

    Linda Austin Long & Foster Real Estate, Inc.

    0 Parks Rd, Chester, MD 21619
  • 5011 Bridgepointe Dr, Chester, MD 21619
    5011 Bridgepointe Dr, Chester, MD 21619
    5011 Bridgepointe Dr, Chester, MD 21619
    /46

    $374,900

    • 3 Beds
    • 2.5 Baths
    • 1,302 Sq Ft

    5011 Bridgepointe Dr, Chester, MD 21619

    Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that

    Nick Waldner Keller Williams Realty Centre

    5011 Bridgepointe Dr, Chester, MD 21619
  • 2008 Bridgepointe Dr, Chester, MD 21619
    2008 Bridgepointe Dr, Chester, MD 21619
    2008 Bridgepointe Dr, Chester, MD 21619
    /39

    $380,000

    • 2 Beds
    • 2 Baths
    • 1,804 Sq Ft

    2008 Bridgepointe Dr, Chester, MD 21619

    Welcome to this gorgeous end unit townhouse offering low-maintenance living in a highly convenient Kent Island location. Thoughtfully designed with both comfort and flexibility in mind, this home features 2 spacious bedrooms and 2 full bathrooms, along with a versatile converted garage space that can easily function as a 3rd bedroom, home office, den or be returned to a traditional garage. The

    Crystal Smith RE/MAX Executive

    2008 Bridgepointe Dr, Chester, MD 21619
  • 114 Merganser Ct, Chester, MD 21619
    114 Merganser Ct, Chester, MD 21619
    114 Merganser Ct, Chester, MD 21619
    /26

    $295,000

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    114 Merganser Ct, Chester, MD 21619

    Nestled in the charming Bayside Marina community, this 2nd floor condo offers a perfect blend of comfort and modern living. Built in 1999, this contemporary gem features an open floor plan that seamlessly connects the living with vaulted ceilings, dining, and kitchen areas, creating an inviting space for relaxation and entertaining. The kitchen boasts ENERGY STAR appliances, including a

    Beverly Sloane Benson & Mangold, LLC

    114 Merganser Ct, Chester, MD 21619
  • 8F Queen Victoria Way, Chester, MD 21619
    8F Queen Victoria Way, Chester, MD 21619
    8F Queen Victoria Way, Chester, MD 21619
    /30

    $240,000

    $9K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    8F Queen Victoria Way, Chester, MD 21619

    Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertaining. Private patio off bedroom with secured storage. Laundry is stackable located in bedroom. You will enjoy the Queen's Landing community clubhouse, marina, tennis court and pool and well as the trails in the community.Call today for your private showing.

    Linda Austin Long & Foster Real Estate, Inc.

    8F Queen Victoria Way, Chester, MD 21619
  • 54F Queen Caroline Ct, Chester, MD 21619
    54F Queen Caroline Ct, Chester, MD 21619
    54F Queen Caroline Ct, Chester, MD 21619
    /46

    $359,900

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54F Queen Caroline Ct, Chester, MD 21619

    Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters, and backsplash, 3 new bathrooms, all new flooring throughout, new washer and dryer and freshly painted. Nestled in the serene enclave of Queens Landing, this exquisite remodeled in 2026 Colonial townhouse offers a harmonious blend of luxury and comfort. Spanning 1,440 square feet, the open floor plan

    Lawrence Doyle Long & Foster Real Estate, Inc.

    54F Queen Caroline Ct, Chester, MD 21619
  • 1025 Dundee Ct, Chester, MD 21619
    1025 Dundee Ct, Chester, MD 21619
    1025 Dundee Ct, Chester, MD 21619
    /53

    $324,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,400 Sq Ft

    1025 Dundee Ct, Chester, MD 21619

    Estate Sale! Motivated Seller offering $5,000.00 in closing costs help! OPEN House this Saturday June 20, 8-10am! Welcome to Kent Island living without the Kent Island price tag! This 3 bedroom, 2.5 bath townhome in Dundee Harbor offers 1,400 square feet of comfortable living space and one of the best values you’ll find on the Island. Opportunities with this kind of price per square foot are few

    Rick Parreco RE/MAX Executive

    1025 Dundee Ct, Chester, MD 21619
  • 45G Queen Neva Ct, Chester, MD 21619
    45G Queen Neva Ct, Chester, MD 21619
    45G Queen Neva Ct, Chester, MD 21619
    /40

    $349,500

    • 2 Beds
    • 2.5 Baths
    • 1,312 Sq Ft

    45G Queen Neva Ct, Chester, MD 21619

    Seller is offering closing cost assistance for qualified buyers! This charming townhouse in Queens Landing offers a perfect blend of comfort and community amenities. Step inside to discover a traditional floor plan featuring a cozy living room off the eat-in kitchen, with a separate family room ideal for gatherings. The home boasts two spacious bedrooms and 2.5 baths, including a primary bath for

    John Freeman Coldwell Banker Realty

    45G Queen Neva Ct, Chester, MD 21619
  • 6005 Bridgepointe Dr, Chester, MD 21619
    6005 Bridgepointe Dr, Chester, MD 21619
    6005 Bridgepointe Dr, Chester, MD 21619
    /38

    $357,900

    $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,302 Sq Ft

    6005 Bridgepointe Dr, Chester, MD 21619

    Low maintenance island living at its best! 6005 Bridgepointe Dr is freshly painted, deep cleaned, and ready for its new owners! All appliances new within the last two years, power washed & fresh paint on the deck with beautiful views of the pond. Easy access to RT50 - perfect for the commuter. Quiet neighborhood.

    Megan Rosendale Rosendale Realty

    6005 Bridgepointe Dr, Chester, MD 21619
  • 54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    /29

    $329,000

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54H Queen Caroline Ct, Chester, MD 21619

    DON"T MISS OUT on this super deal!! Owners have lowered the price by $10,000 and are willing to look at offers! Nothing to do but move in! Be in this spring to enjoy all that summer offers on the shore!! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout the living areas and new vinyl flooring in the kitchen. A

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, Chester, MD 21619
  • 108 Price Rd, Chester, MD 21619
    108 Price Rd, Chester, MD 21619
    108 Price Rd, Chester, MD 21619
    /10

    $240,000

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    108 Price Rd, Chester, MD 21619

    You wouldn't think it but the property offers 3 bedroom and 2 full baths. Patio right off kitchen for the summer cookouts! Easy yard maintenance here, not much grass to manage, leaves plenty of time for those cookouts. Close to Route 8 for easy east/west access. Property sold as is, no repairs will be made by seller. HUD CASE 244-032645, reach out for more information on this unique buying

    Dana Byrd Thurston Wyatt Real Estate, LLC

    108 Price Rd, Chester, MD 21619
  • 54 D Queen Caroline Ct, Chester, MD 21619
    54 D Queen Caroline Ct, Chester, MD 21619
    54 D Queen Caroline Ct, Chester, MD 21619
    /38

    $339,900

    Open Sat 10AM - 1PM $6K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54 D Queen Caroline Ct, Chester, MD 21619

    Move In Ready! Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring elegant quartz countertops—perfect

    Michelle DiDonato Island Realty, LLC

    54 D Queen Caroline Ct, Chester, MD 21619
  • 102 Merganser Ct, Chester, MD 21619
    102 Merganser Ct, Chester, MD 21619
    102 Merganser Ct, Chester, MD 21619
    /15

    $305,000

    $10K PRICE INCREASE Coming Soon
    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    102 Merganser Ct, Chester, MD 21619

    Come see this spacious, coastal inspired condo at Bayside on Kent Island. This 2 BR/2 Bath home offers all the benefits of first floor,one level living. A welcoming entrance whispers, " stay awhile" with a sunny patio area overlooking a lush lawn and water views. Inside you will notice plenty of windows, light, and an open-concept design that creates the perfect mood for that "laid back" Kent

    Carol Delayo Chaney Homes, LLC

    102 Merganser Ct, Chester, MD 21619
  • 0 Lot #1 Harley Ln, Chester, MD 21619
    0 Lot #1 Harley Ln, Chester, MD 21619
    0 Lot #1 Harley Ln, Chester, MD 21619
    /6

    $159,900

    • Land
    • 12,632 Sq Ft
    • $551,379 per Acre

    0 Lot #1 Harley Ln, Chester, MD 21619

    2 Great Building Lots - Sewer Approved on Kent Island , Sewer fee is paid for - Harley Lane Lot #1 Parcel 63 comes with working Well $159,900. An Adjacent Lot #2 Parcel 64 is available. Sewer is also approved with fee paid. $149,900. These approved Lots are registered with Queen Annes County. *****The Harley Lane 2 lot sub division was created by adding 2 lots on land owned on Good hand creek

    Thomas Hennerty NetRealtyNow.com, LLC

    0 Lot #1 Harley Ln, Chester, MD 21619
Maryland Queen Anne's County Chester

Real Estate & Homes in Chester, MD under $400,000

Home Prices in Chester, MD

The median home sale price in Chester, MD is $659,900, up 16% year-over-year. Homes in Chester sell in 291 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$659,900
Median Single Family Sale Price
$705,000
Median Townhouse Sale Price
$374,900
Median 2 Bedroom Sale Price
$599,990
Median 1 Bedroom Sale Price
$294,500
Average Price Per Sq Ft
$300
Number of Homes for Sale
82
Last 12 months Home Sales
223
Months of Supply
4.40
Median List Price
$679,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
16%
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