31

Chester, MD Homes for Sale under $600,000

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  • /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
  • /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
  • /44

    $559,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,536 Sq Ft

    126 Watermans Cove Ln, Chester, MD 21619

    Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience.An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    126 Watermans Cove Ln, Chester, MD 21619
  • /52

    $550,000

    Open Sun 1PM - 3PM
    • 2 Beds
    • 2.5 Baths
    • 1,616 Sq Ft

    47 Queen Anne Way, Chester, MD 21619

    Set directly along the Chester River in desirable Queen’s Landing, this waterfront home puts the water at the center of everyday living, with incredible views from the main level, sunroom, patio, and both upstairs bedrooms. The shoreline feels remarkably close, creating a peaceful backdrop that can be enjoyed from nearly every principal living space. Renovations and upgrades throughout complement

    Agent Photo

    Debra Noone

    Northrop Realty

    47 Queen Anne Way, Chester, MD 21619
  • /12

    $595,000

    Coming Soon Sep 22
    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    1010 Auckland Way, Chester, MD 21619

    Professional Photos Coming Soon - PANORAMIC CHESTER RIVER VIEWS! This fabulous END-UNIT townhome in Kent Island’s sought-after Bayside community offers a special WATERFRONT SETTING with sweeping views of the Chester River as it flows into the Chesapeake Bay. With approximately 2,100 square feet, an abundance of natural light, and water views from so many rooms, this home is all about enjoying the

    Agent Photo

    Lori Woods-Fortney

    Berkshire Hathaway HomeServices Homesale Realty

    1010 Auckland Way, Chester, MD 21619
  • /12

    $509,990

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

    Magothy Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Open airy floorplan on the first floor with private patio.Large gourmet kitchen and dining area, great for entertaining.Wonderful home office for your telecommuting needs.Sumptuous owner’s suite with spa bath .Fantastic great room with large windows for your viewing pleasure.Large secondary bedroom with opt. door to access patio.Pricing is inclusive of an average location

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • /34

    $599,900

    Open Sun 1PM - 3PM
    • 3 Beds
    • 3.5 Baths
    • 2,076 Sq Ft

    1012 Auckland Way, Chester, MD 21619

    Experience Kent Island waterfront living in this beautifully appointed townhome in sought-after Bayside of Chester. The open-concept interior offers abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen is designed for both everyday living and entertaining, featuring generous cabinetry, ample counter space, and a large center island with seating that

    Jerrise Spencer Redfin Corp

    1012 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
  • /33

    $509,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    Chester Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Open floorplan with plenty of room for your family.Wonderful gourmet kitchen and formal dining area.Private home office for your personal space.Large great room off balcony with large windows to capture the day.Luxurious owner’s suite with spa bath and access to balcony.Large secondary bedroom with access to balcony.Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493320, 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
  • /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
  • /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
  • /14

    $539,000

    $10K PRICE DROP Coming Soon Sep 25
    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    15 Queen Anne Way Unit E, Chester, MD 21619

    Located in the beautiful Queens Landing community, this Spanish-style waterfront townhouse offers a luxurious lifestyle with stunning river views. The interior boasts an open floor plan, featuring a combination dining and living area with recessed lighting and a corner gas fireplace. The kitchen is equipped with upgraded countertops and high-end appliances, including a built-in microwave and new

    Jason French Benson & Mangold, LLC

    15 Queen Anne Way Unit E, Chester, MD 21619
  • /23

    $524,999

    $25K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    230 Switchgrass Way Unit 12, Chester, MD 21619

    NEW INCENTIVE — THE OWNERS WILL COVER YOUR $8,000 COMMUNITY BUY-IN WITHACCEPTABLE OFFER!Move-in ready condo with zero wait! This meticulously maintained, first-floor Magothy shows likenew, offering over 2,000 square feet of single-level living in the highly sought-after FourSeasons at Kent Island 55+ active-adult community. Enjoy the rare convenience of directoutdoor patio

    David Moore Real Broker, LLC

    230 Switchgrass Way Unit 12, 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
  • /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
  • /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
  • /49

    $515,000

    $20K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft

    205 Anchor Ln, Chester, MD 21619

    SPACE, FLEXIBILITY & VALUE ON KENT ISLAND! Welcome to 205 Anchor Lane, where generous square footage, versatile two-level living and incredible outdoor space come together to create a home that can truly adapt to your needs. With 5 bedrooms, updated bathrooms and living spaces on both levels, the floor plan offers excellent flexibility for multi-generational living, guests, a home office or the

    Kathleen Higginbotham Samson Properties

    205 Anchor Ln, Chester, MD 21619
  • /83

    $550,000

    • 5 Beds
    • 3.5 Baths
    • 3,552 Sq Ft

    326 Castle Marina Rd, Chester, MD 21619

    Discover the charm of this beautiful home in the desirable Castle Marina community. With five spacious bedrooms (including one on the main level) and 3.5 bathrooms, this residence is designed for comfort and functionality. Enjoy cozy evenings by one of the two fireplaces. With new windows, the natural light floods the traditional floor plan, enhanced by recessed lighting and wood floors

    Ginny Dauses Coldwell Banker Waterman Realty

    326 Castle Marina Rd, 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
  • /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
  • /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
  • /50

    $595,000

    $5K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    1000 Herons Nest Way Unit 43, Chester, MD 21619

    Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment.Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center

    Dee Dee McCracken Coldwell Banker Realty

    1000 Herons Nest Way Unit 43, Chester, MD 21619
  • /63

    $599,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    315 Bentons Pleasure Rd, Chester, MD 21619

    REDUCED!!! This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

    Douglas Kayhoe Douglas Realty LLC

    315 Bentons Pleasure Rd, Chester, MD 21619
  • /13

    $599,990

    New Construction $64K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 12, Chester, MD 21619

    Open home office for flexible work or study.Gourmet kitchen with central island at the heart of the home.Dining area with dry bar for easy entertaining.Great room with electric fireplace for a cozy focal point.Patio off the great room with direct access to the owner's suite.Owner's suite with dual closets for added storage.Owner's bath with dual sinks & glass shower

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 12, 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
  • /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
  • /21

    $594,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    Severn Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36503530, 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
  • /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
  • /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

Home Price Trends

Median Sale Price
$689,900
Median Single Family Sale Price
$749,990
Median Townhouse Sale Price
$369,900
Median 2 Bedroom Sale Price
$634,990
Median 1 Bedroom Sale Price
$338,000
Average Price Per Sq Ft
$310
Number of Homes for Sale
31
Last 12 months Home Sales
213
Months of Supply
4.60
Median List Price
$714,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
15%
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