7

Chester, MD Homes for Sale under $400,000

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  • 1803 Chester Dr, Chester, MD 21619
    1803 Chester Dr, Chester, MD 21619
    1803 Chester Dr, Chester, MD 21619
    /29

    $400,000

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    1803 Chester Dr, Chester, MD 21619

    Adorable rancher on Kent Island in the community of Harbor View! Featuring 3 beds, 2 baths, and private driveway. Enjoy the large fenced yard with deck, shed, and firepit. The living room has a cozy fireplace with wood stove insert. The primary bedroom has a private bath with tile and stand up shower. Updates include both bathrooms, updated windows, roof 2020. Close to Route 50 for easy access to

    Jennifer Kramer-Dela Cruz Keller Williams Legacy

    1803 Chester Dr, Chester, MD 21619
  • 34 Queen Anne Way Unit F, Chester, MD 21619
    34 Queen Anne Way Unit F, Chester, MD 21619
    34 Queen Anne Way Unit F, Chester, MD 21619
    /21

    $349,900

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    34 Queen Anne Way Unit F, Chester, MD 21619

    Rare Opportunity in Queen’s Landing with Stunning Chester River Views Welcome to one of the few oversized one-bedroom condos in the highly desirable Queen’s Landing community. Immaculately maintained and thoughtfully designed, this larger-than-average unit offers gorgeous views of the Chester River and the added benefit of expanded living space rarely found in one-bedroom layouts. The larger

    Joelle Dolch Cross Street Realtors LLC

    34 Queen Anne Way Unit F, Chester, MD 21619
  • 501 Teal Ct, Chester, MD 21619
    501 Teal Ct, Chester, MD 21619
    501 Teal Ct, Chester, MD 21619
    /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
  • 1838 Sherman Dr, Chester, MD 21619
    1838 Sherman Dr, Chester, MD 21619
    1838 Sherman Dr, Chester, MD 21619
    /29

    $387,500

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    1838 Sherman Dr, Chester, MD 21619

    Nestled in the heart of Chester, Maryland on the beautiful Eastern Shore, this charming rancher offers comfort and convenience. Inside, a bright and inviting interior features neutral tones, modern finishes, and a functional layout ideal for everyday living. The light-filled dining area overlooks the backyard and flows into the galley kitchen, complete with stainless steel appliances, ample

    Bret Merson Keller Williams Realty Centre

    1838 Sherman 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
    /40

    $349,000

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

    54H Queen Caroline Ct, Chester, MD 21619

    Nothing to do but move in! 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 propane fireplace highlights the great room turning chilly nights into cozy nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, Chester, MD 21619
  • 2008 Bridgepointe Dr, Chester, MD 21619
    2008 Bridgepointe Dr, Chester, MD 21619
    2008 Bridgepointe Dr, Chester, MD 21619
    /6

    $380,000 Open Sat 12PM - 2PM

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

    2008 Bridgepointe Dr, Chester, MD 21619

    Coming Soon - Gorgeous End Unit Townhouse. 2 Bedrooms and 2 Full Bathrooms with a converted garage that has the potential for a 3rd Bedroom option, den or change back into a garage space! Long Kitchen that leads to an Open Floor Plan Living Area PLUS Bonus Sunroom and Large Rear Deck add additional backyard privacy. Kick back, relax and enjoy the pond and fountain views. More details and photos

    Crystal Smith RE/MAX Executive

    2008 Bridgepointe Dr, Chester, MD 21619
  • 102 Merganser Ct, Chester, MD 21619
    102 Merganser Ct, Chester, MD 21619
    102 Merganser Ct, Chester, MD 21619
    /12

    $300,000 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
Maryland Queen Anne's County Chester

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

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 201 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, MD over the last 12 months is $649,900, up 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$649,900
Median Single Family Sale Price
$684,900
Median Townhouse Sale Price
$372,500
Median 2 Bedroom Sale Price
$549,900
Median 1 Bedroom Sale Price
$294,500
Average Price Per Sq Ft
$298
Number of Homes for Sale
77
Last 12 months Home Sales
213
Months of Supply
4.30
Median List Price
$676,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
12%
How to Buy a Home How to Finance a Home How to Sell a Home

Explore the array of homes and houses for sale under $400,000 in Chester, where you'll find 7 options tailored for those seeking affordable real estate opportunities. Whether you're interested in spacious family homes, modern townhouses, or cozy bungalows, Chester offers a diverse range of choices to match your needs and financial considerations. Take advantage of these affordably-priced properties to make your move into the real estate market in Chester, MD.

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