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Colonial Homes for Sale in Chester, MD

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  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /42

    $725,000

    $45K PRICE DROP
    • 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
  • 134 Mchenny Ct, Chester, MD 21619
    134 Mchenny Ct, Chester, MD 21619
    134 Mchenny Ct, Chester, MD 21619
    /31

    $579,000

    $36K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft

    134 Mchenny Ct, Chester, MD 21619

    Just Reduced! Best value in Gibsons Grant. 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

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 771-2810

    134 Mchenny Ct, Chester, MD 21619
  • 1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, Chester, MD 21619
    /46

    $599,900

    Open Sat 2PM - 4PM
    • 3 Beds
    • 3.5 Baths
    • 2,076 Sq Ft

    1012 Auckland Way, Chester, MD 21619

    Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyday comfort and effortless entertaining, this residence features an open-concept floor plan with abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen serves as the heart of the home,

    Jerrise Spencer Redfin Corp

    1012 Auckland Way, Chester, MD 21619
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /48

    $425,500

    • 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
  • 154 Bluebell Ct, Chester, MD 21619
    154 Bluebell Ct, Chester, MD 21619
    154 Bluebell Ct, Chester, MD 21619
    /20

    $995,000

    Coming Soon
    • 3 Beds
    • 3 Baths
    • 3,434 Sq Ft

    154 Bluebell Ct, Chester, MD 21619

    Welcome to luxury, comfort, and effortless living in the highly sought-after first section of Four Seasons at Kent Island. Offering a floor plan no longer available in the community's newer sections, this exceptional home combines thoughtful design with upscale finishes throughout. A spacious foyer welcomes you into an open and inviting layout that is perfect for both everyday living and

    Tricia Wilson Wilson Realty & Staging LLC

    154 Bluebell Ct, Chester, MD 21619
  • 115 Gibson Cir, Chester, MD 21619
    115 Gibson Cir, Chester, MD 21619
    115 Gibson Cir, Chester, MD 21619
    /42

    $585,000

    • 2 Beds
    • 2.5 Baths
    • 2,048 Sq Ft

    115 Gibson Cir, Chester, MD 21619

    Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxurious lifestyle with a perfect blend of comfort and elegance. Built in 2009, this Colonial-style residence spans 2,048 square feet and features two spacious bedrooms , with a another room that could be used for a 3rd bedroom and two and a half bathrooms, making it an ideal retreat for those seeking both

    Lawrence Doyle Long & Foster Real Estate, Inc.

    115 Gibson Cir, Chester, MD 21619
  • 200 Newtown Rd, Chester, MD 21619
    200 Newtown Rd, Chester, MD 21619
    200 Newtown Rd, Chester, MD 21619
    /50

    $420,000

    Open Sat 1:30PM - 3:30PM $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,296 Sq Ft

    200 Newtown Rd, Chester, MD 21619

    $25k Price Improvement + Views of Crab Alley! 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 for six, ideal for

    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

    • 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
  • 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

    $24K PRICE DROP
    • 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

    $1,283,780

    New Construction Open Sun 1PM - 3PM
    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    *****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!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

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
  • 124 Riverside Dr, Chester, MD 21619
    124 Riverside Dr, Chester, MD 21619
    124 Riverside Dr, Chester, MD 21619
    /45

    $545,000

    $5K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 1,979 Sq Ft

    124 Riverside Dr, Chester, MD 21619

    Gorgeous, like-new home on Kent Island! Fresh interior paint and new carpet throughout make this home truly move-in ready. The spacious living and dining areas offer plenty of room for relaxing and entertaining, while the inviting fireplace adds warmth and charm. The kitchen features a breakfast bar, pantry, abundant cabinetry, and plenty of storage. The spacious owner’s suite includes two

    Christine Schumaker Douglas Realty LLC

    124 Riverside Dr, Chester, MD 21619
  • 232 Evelyne St, Chester, MD 21619
    232 Evelyne St, Chester, MD 21619
    232 Evelyne St, Chester, MD 21619
    /35

    $865,000

    • 4 Beds
    • 3.5 Baths
    • 3,312 Sq Ft

    232 Evelyne St, Chester, MD 21619

    Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs,

    Courtney Chipouras TTR Sotheby's International Realty

    232 Evelyne St, Chester, MD 21619
Maryland Queen Anne's County Chester

Real Estate & Homes for Sale in Chester, MD

Home Prices in Chester, MD

The median home sale price in Chester, MD is $657,400, up 15% year-over-year. Homes in Chester sell in 294 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$657,400
Median Single Family Sale Price
$703,495
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
$301
Number of Homes for Sale
81
Last 12 months Home Sales
226
Months of Supply
4.30
Median List Price
$679,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
15%
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