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Ranch Style Homes for Sale in Chester, MD

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  • 2645 Cox Neck Rd, Chester, MD 21619
    2645 Cox Neck Rd, Chester, MD 21619
    2645 Cox Neck Rd, Chester, MD 21619
    /61

    $399,500

    Open Sat 9AM - 11AM
    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft

    2645 Cox Neck Rd, Chester, MD 21619

    Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre lot, this well-maintained property combines comfort, convenience, and exceptional value at $399,500. Inside, you'll find a bright and inviting floor plan featuring a kitchen with a stylish tile backsplash, ample cabinetry, and

    Agent Photo

    Gretchen Wichlinski

    Compass

    (410) 696-5042

    2645 Cox Neck Rd, Chester, MD 21619
  • 2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    /78

    $1,250,000

    Open Sat 11:30AM - 1:30PM
    • 4 Beds
    • 4.5 Baths
    • 4,413 Sq Ft

    2855 Cox Neck Rd, Chester, MD 21619

    Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring

    Tricia Wilson Wilson Realty & Staging LLC

    2855 Cox Neck Rd, Chester, MD 21619
  • 111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    /48

    $1,200,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    111 Flycatcher Way, Chester, MD 21619

    The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end finishes and thoughtful upgrades throughout. Available for immediate settlement with a rent-back opportunity, this expansive home features 5 bedrooms, 4.5 baths, and a 3-car garage, delivering both space and sophistication. Standout features include a dedicated home office, an inviting fireplace, and a

    Mary Anne Kowalewski KOVO Realty

    111 Flycatcher Way, Chester, MD 21619
  • 723 Warbler Way, Chester, MD 21619
    723 Warbler Way, Chester, MD 21619
    723 Warbler Way, Chester, MD 21619
    /38

    $799,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    723 Warbler Way, Chester, MD 21619

    Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the

    Mary Anne Kowalewski KOVO Realty

    723 Warbler Way, Chester, MD 21619
  • 108 Price Rd, Chester, MD 21619
    108 Price Rd, Chester, MD 21619
    108 Price Rd, Chester, MD 21619
    /10

    $240,000

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    108 Price Rd, Chester, MD 21619

    You wouldn't think it but the property offers 3 bedroom and 2 full baths. Patio right off kitchen for the summer cookouts! Easy yard maintenance here, not much grass to manage, leaves plenty of time for those cookouts. Close to Route 8 for easy east/west access. Property sold as is, no repairs will be made by seller. HUD CASE 244-032645, reach out for more information on this unique buying

    Dana Byrd Thurston Wyatt Real Estate, LLC

    108 Price Rd, Chester, MD 21619
  • 127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    /49

    $900,000

    New Construction
    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft

    127 Flycatcher Way, Chester, MD 21619

    The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a

    Mary Anne Kowalewski KOVO Realty

    127 Flycatcher 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

    $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
  • 1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    /41

    $449,900

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1906 Harbor Dr, Chester, MD 21619

    *PRICE IMPROVEMENT!* Welcome to this beautifully renovated ranch-style home offering 4 bedrooms, 2 full bathrooms, and a spacious open floor plan designed for modern living. Completely remodeled from top to bottom, this move-in ready property combines style, comfort, and functionality in every detail. The stunning kitchen features sleek quartz countertops, stainless steel appliances, and a large

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, Chester, MD 21619
  • 715 Warbler Way, Chester, MD 21619
    715 Warbler Way, Chester, MD 21619
    715 Warbler Way, Chester, MD 21619
    /38

    $849,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    715 Warbler Way, Chester, MD 21619

    Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the

    Mary Anne Kowalewski KOVO Realty

    715 Warbler Way, Chester, MD 21619
  • 206 Anchor Ln, Chester, MD 21619
    206 Anchor Ln, Chester, MD 21619
    206 Anchor Ln, Chester, MD 21619
    /40

    $569,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    206 Anchor Ln, Chester, MD 21619

    KENT ISLAND ** CUSTOM RANCHER ** Welcome to the sought-after neighborhood of Castle Marina. There are No HOA or Association fees in this established community. You can walk to your boat in the marina, stroll to the local pub for dinner or hit the Cross Island Trail to get in your steps for the day. So close to all of the amenities Kent Island has to offer, yet tucked away behind Four Seasons,

    Suzanne Hitt Coldwell Banker Waterman Realty

    206 Anchor Ln, Chester, MD 21619
  • 123 Flycatcher Way, Chester, MD 21619
    123 Flycatcher Way, Chester, MD 21619
    123 Flycatcher Way, Chester, MD 21619
    /47

    $1,200,000

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    123 Flycatcher Way, Chester, MD 21619

    The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer finishes throughout—available now for immediate settlement with a rent-back opportunity. Thoughtfully designed with 3 bedrooms, 3 baths, and a 3-car garage, this home blends spacious living, refined styling, and everyday functionality. Standout features include a dedicated home office, an inviting fireplace,

    Mary Anne Kowalewski KOVO Realty

    123 Flycatcher Way, Chester, MD 21619
  • 117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    /49

    $1,200,000

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    117 Flycatcher Way, Chester, MD 21619

    The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio

    Mary Anne Kowalewski KOVO Realty

    117 Flycatcher Way, 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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