20

Chester, MD Homes for Sale under $500,000

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  • 108 Blenny Ln, Chester, MD 21619
    108 Blenny Ln, Chester, MD 21619
    108 Blenny Ln, Chester, MD 21619
    /26

    $389,900

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

    108 Blenny Ln, Chester, MD 21619

    Bayside In Kent Island Located in the Popular Community of Bayside just minutes from the Bay Bridge and all Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    108 Blenny Ln, Chester, MD 21619
  • 4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    /70

    $499,000

    $61K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - Reduced! * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    4000 Herons Nest Way Unit 22, 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
  • 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

    Seller is offering up to $9,000 toward the buyer's interest rate buydown or closing costs. That's real money applied at settlement, and on a home already carrying over $50,000 in owner improvements, it's the kind of combination that doesn't sit long.This is a renovated end-unit townhome with three bedrooms and three and a half baths in Bayside, an established waterfront community along

    David Moore Real Broker, LLC

    807 Auckland Way, Chester, MD 21619
  • 6005 Bridgepointe Dr, Chester, MD 21619
    6005 Bridgepointe Dr, Chester, MD 21619
    6005 Bridgepointe Dr, Chester, MD 21619
    /54

    $349,000

    Open Sun 10AM - 12PM
    • 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 has a NEW ROOF, NEW A/C UNIT, freshly painted 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
  • 114 Merganser Ct, Chester, MD 21619
    114 Merganser Ct, Chester, MD 21619
    114 Merganser Ct, Chester, MD 21619
    /27

    $287,500

    $12K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    114 Merganser Ct, Chester, MD 21619

    "Why rent when you can own?" or are you looking for a weekend home? This condo is has so many options at an affordable price. Experience the ease of resort-style, maintenance-free living in this beautifully updated upper-level condominium featuring open views, abundant natural light, and the privacy of having no neighbors above. Also, owning the upper level gives you the security if you are a

    Beverly Sloane Benson & Mangold, LLC

    114 Merganser Ct, Chester, MD 21619
  • 12 Queen Anne Way Unit J, Chester, MD 21619
    12 Queen Anne Way Unit J, Chester, MD 21619
    /2

    $379,900

    Coming Soon Sep 23
    • 1 Bed
    • 1.5 Baths
    • 1,260 Sq Ft

    12 Queen Anne Way Unit J, Chester, MD 21619

    Enjoy waterfront living in the sought-after Queens Landing community! This Mediterranean style 1-bedroom, 1.5-bath end unit condo offers a unique layout with beautiful water views and multiple outdoor spaces designed to make the most of the setting. The first-level primary bedroom and full bath allow for convenient main-level living. The upper-level loft adds valuable flex space with a

    Marti McGinty Chesapeake Real Estate Associates, LLC

    12 Queen Anne Way Unit J, Chester, MD 21619
  • 43A Queen Neva Ct, Chester, MD 21619
    43A Queen Neva Ct, Chester, MD 21619
    43A Queen Neva Ct, Chester, MD 21619
    /72

    $459,000

    • 3 Beds
    • 2.5 Baths
    • 2,008 Sq Ft

    43A Queen Neva Ct, Chester, MD 21619

    Welcome to 43-A Queen Neva Court, a pristine 3-bedroom, 2.5-bath contemporary condo in the sought-after Queens Landing community. Offering more than 2,000 square feet of living space, this spacious end unit features an open, sunlit floor plan that is perfect for everyday living and entertaining. The oversized kitchen provides abundant workspace and storage, while the inviting living area is

    Ryan Briggs Anne Arundel Properties, Inc.

    43A Queen Neva Ct, 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

    $349,900

    $25K 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
  • 45G Queen Neva Ct, Chester, MD 21619
    45G Queen Neva Ct, Chester, MD 21619
    45G Queen Neva Ct, Chester, MD 21619
    /40

    $318,500

    $31K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,312 Sq Ft

    45G Queen Neva Ct, Chester, MD 21619

    Price Improvement! 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

    John Freeman Coldwell Banker Realty

    45G Queen Neva Ct, 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
    /56

    $485,000

    Open Sun 11AM - 3PM $3K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE.This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 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

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, 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

    $299,900

    $46K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54 D Queen Caroline Ct, Chester, MD 21619

    Motivated Seller! This home is 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

    Michelle DiDonato Island Realty, LLC

    54 D Queen Caroline 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

    $374,900

    $84K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 1,899 Sq Ft

    208 Blenny Ln Unit 100, Chester, MD 21619

    NEW AMAZING PRICE!! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully renovated 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
  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /48

    $400,000

    Open Sat 12PM - 1PM
    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1868 Roberta Dr, Chester, MD 21619

    List price is Opening Bid at the Online auction to be conducted on Auctioneers website.- Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and versatility of 1868 Roberta Drive in Chester, Maryland, a custom-built home offering 5 bedrooms, 3.5 bathrooms, multiple living areas, abundant storage, and no HOA. Conveniently located just minutes from Route 50 and the

    Carley Cooper Alex Cooper Auctioneers, Inc.

    1868 Roberta Dr, 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

    $439,900

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

    1340 Queen Anne Dr, Chester, MD 21619

    PRICE Improvement...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

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • 2004 Bridgepointe Dr, Chester, MD 21619
    2004 Bridgepointe Dr, Chester, MD 21619
    2004 Bridgepointe Dr, Chester, MD 21619
    /32

    $369,900

    Open Sun 10AM - 12PM $13K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    2004 Bridgepointe Dr, Chester, MD 21619

    REDUCED!! Welcome to one of the most desirable Homes in the Bridgepointe Community! ALL NEW Carpet & flooring, fresh custom paint, Granite countertops and Newer Appliances! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of the community's most sought after

    Sheryl Carmody RE/MAX Executive

    2004 Bridgepointe Dr, Chester, MD 21619
  • 200 Church St, Chester, MD 21619
    200 Church St, Chester, MD 21619
    200 Church St, Chester, MD 21619
    /28

    $350,000

    Open Sun 12PM - 2PM
    • 2 Beds
    • 2 Baths
    • 1,274 Sq Ft

    200 Church St, Chester, MD 21619

    Your Island Getaway Is Waiting!Dreaming of a cozy home where life feels a little more relaxed and every season brings something to look forward to? This charming 2/3-bedroom Island home may be just what you’ve been waiting for!Start your mornings—or wind down your evenings—on the inviting front porch, where you can swing with the little ones, rock to your favorite playlist, and enjoy the

    Darlene Winegardner RE/MAX Executive

    200 Church St, Chester, MD 21619
  • 53 Queen Caroline Ct, Chester, MD 21619
    53 Queen Caroline Ct, Chester, MD 21619
    53 Queen Caroline Ct, Chester, MD 21619
    /38

    $329,000

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    53 Queen Caroline Ct, Chester, MD 21619

    Nestled in the community of Queens Landing, this townhome offers a blend of coastal charm and contemporary elegance with carefree living. Boat slips with provisioned boats when available through marina along with Kayaking and storage. With 1,440 square feet of thoughtfully designed living space, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan

    Tammy Studebaker EXP Realty, LLC

    53 Queen Caroline Ct, Chester, MD 21619
  • 106 Bodys Neck Rd, Chester, MD 21619
    106 Bodys Neck Rd, Chester, MD 21619
    106 Bodys Neck Rd, Chester, MD 21619
    /48

    $429,900

    $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,595 Sq Ft

    106 Bodys Neck Rd, Chester, MD 21619

    Marina views, waterfront surroundings, and the Bayside lifestyle—all at a new price of $429,900!Welcome to 106 Bodys Neck Road in Chester, where everyday living comes with a view. This 3-bedroom, 2.5-bath home offers upper and lower decks overlooking the marina, creating inviting spaces to enjoy your morning coffee, unwind at the end of the day, or simply watch the activity along the

    Bill Longest Realty Navigator

    106 Bodys Neck Rd, Chester, MD 21619
  • 3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    /66

    $498,500

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

    3000 Herons Nest Way Unit 11, Chester, MD 21619

    Love where you live! This highly sought-after first-floor condo offers the opportunity to own a fully upgraded 2,003 square foot Four Seasons Condo without waiting for new construction. Just steps from the waterfront and features an open, light-filled floor plan enhanced by crown molding, recessed lighting, and beautiful views of lush greenspace with seasonal water glimpses. The gourmet kitchen

    John Freeman Coldwell Banker Realty

    3000 Herons Nest Way Unit 11, Chester, MD 21619
Maryland Queen Anne's County

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

Home Prices in Chester, MD

The median home sale price in Chester, MD is $684,500, up 14% year-over-year. Homes in Chester sell in 429 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$684,500
Median Single Family Sale Price
$749,990
Median Townhouse Sale Price
$374,900
Median 2 Bedroom Sale Price
$629,990
Median 1 Bedroom Sale Price
$338,000
Average Price Per Sq Ft
$309
Number of Homes for Sale
20
Last 12 months Home Sales
216
Months of Supply
4.70
Median List Price
$708,445
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
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