15

Chester, MD Homes for Sale under $500,000

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  • 131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    /12

    $489,990 New Construction

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

    Magothy Plan at K. Hovnanian’s® 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 premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    /2

    $479,000

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

    312 Blenny Ln, Chester, MD 21619

    You do not want to miss this opportunity to enjoy island living in this maintenance free, WATER VIEW-End UNIT! Come enjoy island living in the Bayside Community. Offering POND views from every window in this sought after end unit home complete with beautiful landscaping. Relax on your spacious deck overlooking the pond complete with 2 fountains or invite family and friends to enjoy a cookout on

    Judith Brown Samson Properties

    312 Blenny Ln, Chester, MD 21619
  • 131 Flycatcher Way Unit 36493320, Chester, MD 21619
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
    /33

    $489,990 New Construction

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

    Chester Plan at K. Hovnanian’s® 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
  • 0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    /12

    $499,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    0 Harbor Dr, Chester, MD 21619

    New home being built! Act now and pick all your colors! Finished models can be seen! Call agent for details.

    DJ Dauses Coldwell Banker Waterman Realty

    0 Harbor Dr, Chester, MD 21619
  • 630 Warbler Way Unit 12, Chester, MD 21619
    630 Warbler Way Unit 12, Chester, MD 21619
    630 Warbler Way Unit 12, Chester, MD 21619
    /8

    $499,990 New Construction

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

    630 Warbler Way Unit 12, Chester, MD 21619

    Charming gourmet kitchen featuring center island & ample counter space. Electric fireplace adds warmth to spacious great room. Refined dining area with dry bar. Functional home office for studying or reading. Private owner's suite & spa bath with walk-in closet. Versatile covered patio for outdoor relaxation.

    K. Hovnanian Homes Builder
    630 Warbler Way Unit 12, Chester, MD 21619
  • 1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    /33

    $454,900

    • 2 Beds
    • 2 Baths
    • 1,444 Sq Ft

    1401 Calvert Rd, Chester, MD 21619

    Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - PRICE REDUCED - All on one level - Beautifully landscaped 3/4 acre lot that backs to trees - fenced patio area - 2 bedrooms with lots of windows and large closets - 2 full baths, one with a tub, one with a walkin shower - fabulous sunroom addition - quiet office area - updated kitchen with granite counters, newer

    Suzanne Hitt Coldwell Banker Waterman Realty

    1401 Calvert Rd, Chester, MD 21619
  • 170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    /79

    $499,000

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

    170 Harrier Way Unit 22, Chester, MD 21619

    Leaves are falling—and so is the price of this stunning condo in the fun, vibrant, and highly sought-after Four Seasons at Kent Island community. Act fast! This is the most breathtaking time of year to make this home yours. As the trees shift from summer green to the rich colors of fall, Mother Nature puts on her finest show. And once the leaves drop, the Chester River opens up before you—right

    Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, 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
  • 1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    /28

    $499,000

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Move in this May and enjoy low-maintenance living in the sought-after 55+ community of Four Seasons on Kent Island. This 2-bedroom, 2-bath home offers spacious one-level living with an open layout, freshly painted interiors, and a stylish kitchen featuring a modern glass subway tile backsplash—perfect for entertaining or relaxing. A 1-car garage with additional storage units keeps everything

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • 906 Auckland Way, Chester, MD 21619
    906 Auckland Way, Chester, MD 21619
    906 Auckland Way, Chester, MD 21619
    /36

    $499,900

    • 3 Beds
    • 3.5 Baths
    • 2,076 Sq Ft

    906 Auckland Way, Chester, MD 21619

    This beautifully maintained 3-bedroom, 3.5-bath marina-front townhouse with a 1-car garage offers the perfect blend of comfort, convenience, and Chesapeake lifestyle. Ideally located in the heart of Kent Island, you’ll enjoy stunning marina and Chester River views from multiple levels. The main floor features new luxury vinyl plank flooring, an open-concept kitchen, dining, and family room, and a

    Courtney Chipouras TTR Sotheby's International Realty

    906 Auckland Way, 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

    $459,900

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

    1340 Queen Anne Dr, Chester, MD 21619

    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 accented with stylish

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • 1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    /3

    $499,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1906 Harbor Dr, Chester, MD 21619

    Beautifully renovated/remodeled 3 bedroom, 2 full bath home in Chester, MD. Expected date to go active on the market is January 1st, 2026.

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, Chester, MD 21619
  • 1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    /40

    $495,000 Open House 1/10

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    1916 Stevens Dr, Chester, MD 21619

    Discover this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a scenic 0.35-acre corner lot in the highly desirable Harbor View community, just two miles east of the Chesapeake Bay Bridge. Inside, enjoy a bright, modern kitchen with new countertops and backsplash, hardwood floors on the main and upstairs evels, and cathedral ceiling with skylights. Relax in the spacious

    Kimberly O'Connor Coldwell Banker Realty

    1916 Stevens Dr, Chester, MD 21619
  • 34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    /57

    $469,000

    • 2 Beds
    • 2.5 Baths
    • 1,104 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water-privileged resort-style community of Queen's Landing, along the scenic Chester River and Macum Creek off the Chesapeake Bay. Step into the light-filled foyer and head up the stairs to the main level, you will find this lovely 2 bedroom, 2.5 bath condominium is move in ready. Just bring your patio chairs,

    Lona Todd Taylor Properties

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

    $480,000 Open House 1/03

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    15 Queen Anne Way Unit E, Chester, MD 21619

    Escape to the water — without the waterfront price. This Chester River–front townhome in Queens Landing is the perfect second home or low-maintenance retreat, all for under $500K. Enjoy sunrise water views from your private patio and balcony, and lock-and-leave peace of mind when you head back home. Inside, the layout is easy and functional with luxury vinyl plank flooring, a gas fireplace, and a

    Jennifer Thomas RE/MAX Executive

    15 Queen Anne Way Unit E, Chester, MD 21619
Maryland Queen Annes County Chester

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

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 102 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, MD over the last 12 months is $629,900, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$629,900
Median Single Family Sale Price
$649,450
Median Townhouse Sale Price
$395,000
Median 2 Bedroom Sale Price
$540,656
Median 1 Bedroom Sale Price
$320,000
Average Price Per Sq Ft
$292
Number of Homes for Sale
62
Last 12 months Home Sales
189
Months of Supply
3.90
Median List Price
$639,675
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 15 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Chester, MD and find the perfect fit for your homeownership goals.

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