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Colonial Homes for Sale in Chester, MD

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  • 134 Mchenny Ct, Chester, MD 21619
    134 Mchenny Ct, Chester, MD 21619
    134 Mchenny Ct, Chester, MD 21619
    /31

    $615,000

    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft

    134 Mchenny Ct, Chester, MD 21619

    Welcome home to this beautifully maintained three-bedroom, two-and-a-half-bath home in the sought-after waterfront community of Gibson’s Grant, where lifestyle and a prime Kent Island location come together effortlessly. A welcoming front porch sets the tone, leading into an open-concept main level designed for both everyday living and entertaining. The spacious living room with propane fireplace

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 771-2810

    134 Mchenny Ct, Chester, MD 21619
  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /42

    $744,500 Open Sat 11AM - 1PM

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1868 Roberta Dr, Chester, MD 21619

    Price improvement! Motivated sellers. This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 446-2477

    1868 Roberta Dr, Chester, MD 21619
  • 1405 Little Creek Rd, Chester, MD 21619
    1405 Little Creek Rd, Chester, MD 21619
    /2

    $19,500

    • 2 Beds
    • 1 Bath
    • 764 Sq Ft

    1405 Little Creek Rd, Chester, MD 21619

    This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.Please note that

    Dustin Parker The Parker Group

    1405 Little Creek Rd, Chester, MD 21619
  • 200 Schooner Way, Chester, MD 21619
    200 Schooner Way, Chester, MD 21619
    200 Schooner Way, Chester, MD 21619
    /64

    $550,000

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

    200 Schooner Way, Chester, MD 21619

    Just minutes over the Chesapeake Bay Bridge, this beautifully maintained end-unit townhome in Bayside offers the perfect Eastern Shore escape. Spectacular water views overlooking Castle Harbor Marina, the home features multiple decks, updated finishes, and, if you choose Castle Harbor Marina, easy access to your boat slip, only steps away. With approximately 2,100 square feet on three finished

    Michele Cordle Long & Foster Real Estate, Inc.

    200 Schooner Way, Chester, MD 21619
  • 200 Newtown Rd, Chester, MD 21619
    200 Newtown Rd, Chester, MD 21619
    200 Newtown Rd, Chester, MD 21619
    /50

    $445,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,296 Sq Ft

    200 Newtown Rd, Chester, MD 21619

    Buyer's Financing Fell Through - No Fault of the home or seller! Welcome to 200 Newtown Road, a charming home perfectly suited for those looking to enjoy Eastern Shore living. The inviting front porch offers the perfect spot to relax and unwind, while the screened porch provides additional space to enjoy the outdoors in comfort. Inside, you’ll find a generously sized kitchen with room for a table

    Kathleen Higginbotham Samson Properties

    200 Newtown Rd, 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

    $375,000 Coming Soon

    • 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
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /47

    $425,000

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

    807 Auckland Way, Chester, MD 21619

    Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades.Welcome to Bayside living at its finest. This meticulously maintained

    David Moore Real Broker, LLC

    807 Auckland Way, Chester, MD 21619
  • 208 Blenny Ln Unit 100, Chester, MD 21619
    208 Blenny Ln Unit 100, Chester, MD 21619
    208 Blenny Ln Unit 100, Chester, MD 21619
    /32

    $434,900

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

    208 Blenny Ln Unit 100, Chester, MD 21619

    PRICE REDUCTION! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully refreshed from top to bottom! Step inside to find the main level that boasts new carpet and new LVP flooring, a new half bath, new paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home

    Pamela Ackermann-Doll RE/MAX Executive

    208 Blenny Ln Unit 100, Chester, MD 21619
  • 1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    /64

    $1,167,890 New Construction

    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    *****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
Maryland Queen Anne's County Chester

Real Estate & Homes for Sale in Chester, MD

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 253 days on the market compared to the national average of 57 days. The median sale price for homes in Chester, MD over the last 12 months is $643,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$643,000
Median Single Family Sale Price
$699,209
Median Townhouse Sale Price
$378,500
Median 2 Bedroom Sale Price
$553,450
Median 1 Bedroom Sale Price
$294,500
Average Price Per Sq Ft
$302
Number of Homes for Sale
76
Last 12 months Home Sales
213
Months of Supply
4.30
Median List Price
$668,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
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