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Chester, MD Homes for Sale

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  • 204 Skipper Ln, Chester, MD 21619
    204 Skipper Ln, Chester, MD 21619
    204 Skipper Ln, Chester, MD 21619
    /106

    $650,000 Open Sat 10AM - 12PM

    • 6 Beds
    • 3 Baths
    • 3,760 Sq Ft

    204 Skipper Ln, Chester, MD 21619

    Welcome home to spacious comfort and thoughtful design in this inviting six-bedroom, three-bath residence nestled on a quiet lane in Chester. With over 3,700 square feet of interior living space, there’s room here for everyone—and maybe even that home office or gym you’ve been dreaming about.Step inside to find an updated kitchen ready for your culinary adventures, featuring modern

    Agent Photo

    Andy Schweigman

    Douglas Realty, LLC

    (410) 324-6571

    204 Skipper Ln, Chester, MD 21619
  • 330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    /55

    $989,000

    • 4 Beds
    • 3.5 Baths
    • 3,949 Sq Ft

    330 Macum Creek Dr, Chester, MD 21619

    Great price on this home with tons of upgrades! Sellers have found Home of Choice. Welcome home to luxurious living Gibson's Grant! This stunning home offers a perfect blend of luxury and functionality, featuring extensive upgrades throughout. The backyard is an entertainer’s dream with a custom patio, covered outdoor kitchen, bonus grassy area for pets or play, and a fully fenced yard. A former

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 256-7961

    330 Macum Creek 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,

    Agent Photo

    Lona Todd

    Taylor Properties

    (667) 291-8898

    34 Queen Anne Way, Chester, MD 21619
  • 54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    /43

    $450,000

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54A Queen Caroline Ct, Chester, MD 21619

    OPEN HOUSE, Saturday, August 2, from 11 am to 12 pm...Price Improvement...End Unit in Sought-After Queens Landing – A Waterfront Lifestyle Awaits!Don’t miss this spacious end unit in the highly desirable Queens Landing community! Featuring two primary bedroom suites with private baths, this home offers the perfect blend of comfort and functionality. The expansive kitchen is a chef’s

    Darlene Winegardner RE/MAX Executive

    54A Queen Caroline Ct, Chester, MD 21619
  • 170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    /74

    $499,000

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

    170 Harrier Way Unit 11, Chester, MD 21619

    ***Redfin powered by Rocket Mortgage Preferred Pricing*** Enjoy with a 1% lower interest rate for your initial year or potential savings of up to $6,000 on your closing costs when you finance with Rocket Mortgage*** Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent

    Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
  • 131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    /27

    $844,900 New Construction

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

    Franklin Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Formal dining room off foyer for entertaining guests. Stylish kitchen with plenty of cabinet space and large island. Open and airy great room with slider to covered patio. Luxurious primary suite with triple windows. Private primary bath with optional freestanding tub. Convenient 2-car garage with storage space.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • 131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    /25

    $659,900 New Construction

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

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private home office for working from home. Stylish kitchen with large center island and spacious pantry. Spacious great room with slider to covered patio. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with split vanities. Convenient HovHall off garage for keeping home tidy.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36466218, Chester, MD 21619
  • 131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    /27

    $807,900 New Construction

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

    Kerr Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage for additional storage space.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • 131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    /41

    $836,900 New Construction

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

    Tuscaloosa Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Extra Suite with full bath for overnight guests. Private home office off foyer for working from home. Spacious great room with adjacent dining area. Beautiful kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • 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

    $474,990 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

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    /10

    $740,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    Taylor Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Secluded bedroom 2 and bath off foyer for overnight guests.Stylish home office off foyer for working from home.Open & airy great room with adjacent dining area.Striking kitchen with island & tons of cabinet space.Luxurious primary suite with oversized walk-in closet.Palatial primary bath with roomy shower.Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36474700, Chester, MD 21619
  • 131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    /12

    $872,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    Mykonos Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36477689, Chester, MD 21619
  • 245 Peregrine Dr, Chester, MD 21619
    245 Peregrine Dr, Chester, MD 21619
    245 Peregrine Dr, Chester, MD 21619
    /34

    $700,000

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    245 Peregrine Dr, Chester, MD 21619

    Professional photos coming soon-This spacious 4-bedroom, 3-bathroom home offers the perfect balance of comfort, style, and functionality. Nestled in a tranquil and highly sought-after neighborhood, this home boasts an open-concept layout, ideal for entertaining guests with the screen in back porch. The inviting living room flows seamlessly into the luxury kitchen, featuring modern appliances,

    Brandi Bradshaw Keller Williams Select Realtors of Annapolis

    245 Peregrine Dr, Chester, MD 21619
  • 124 Nauset Ln, Chester, MD 21619
    124 Nauset Ln, Chester, MD 21619
    124 Nauset Ln, Chester, MD 21619
    /35

    $847,500 Open House 8/17

    • 3 Beds
    • 3 Baths
    • 2,583 Sq Ft

    124 Nauset Ln, Chester, MD 21619

    Turnkey Luxury with Over $175K in Upgrades – Four Seasons at Kent IslandThis beautifully enhanced Killarney with Loft model in Phase I offers the ultimate in resort-style living, featuring over $100K in builder upgrades and $75K in custom renovations.The gourmet kitchen impresses with a 10’ white quartz island, dry bar, SMART stainless appliances, InstaHot water dispenser, and

    Jennifer Thomas RE/MAX Executive

    124 Nauset Ln, Chester, MD 21619
  • 104 Woods Rd, Chester, MD 21619
    104 Woods Rd, Chester, MD 21619
    104 Woods Rd, Chester, MD 21619
    /38

    $805,000 Open Sun 11AM - 1PM

    • 5 Beds
    • 3.5 Baths
    • 3,065 Sq Ft

    104 Woods Rd, Chester, MD 21619

    FANTASTIC HOME! THE COMPLETE PACKAGE AND THEN MORE! TWO PRIMARY BEDROOM/BATH SUITES! BOTH WITH GIANT WALK IN CLOSETS! EACH PRIMARY BATH HAS A STEP IN SHOWER, DOUBLE STONE VANITY PLUS SOAKING TUB! THIS HOME HAS A TOTAL OF 5 BEDROOMS PLUS 3 AND ONE HALF BATHS! PLENTY OF SPACE FOR THE HOME OFFICE! THE OPEN KITCHEN IS FULLY UPDATED WITH ISLAND, STAINLESS STEEL DOUBLE OVENS, COOKTOP, DRAWER

    Temple Peirce Cummings & Co. Realtors

    104 Woods Rd, Chester, MD 21619
  • 223 Broadwater Dr, Chester, MD 21619
    223 Broadwater Dr, Chester, MD 21619
    223 Broadwater Dr, Chester, MD 21619
    /56

    $849,500 Open Sat 11AM - 2PM

    • 3 Beds
    • 3 Baths
    • 2,745 Sq Ft

    223 Broadwater Dr, Chester, MD 21619

    ****************Welcome to Your Dream Home at Four Seasons on Kent Island*******************Step into refined elegance and low-maintenance luxury living with this stunning Killarney w/Loft model, the most sought-after floor plan in the exclusive Four Seasons at Kent Island community. This single family home blends style, comfort, and functionality, in one of the Eastern Shore's premier 55+

    Ralph Kennedy RE/MAX Executive

    223 Broadwater Dr, Chester, MD 21619
  • 314 Thomas White Blvd, Chester, MD 21619
    314 Thomas White Blvd, Chester, MD 21619
    314 Thomas White Blvd, Chester, MD 21619
    /57

    $789,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    314 Thomas White Blvd, Chester, MD 21619

    Welcome to 314 Thomas White Blvd. Nestled in the sought-after waterfront community of Gibson’s Grant, this 4-bedroom, 3.5-bath home offers the perfect blend of refined living and relaxed coastal comfort. You will fall in love with the inviting front porch to the detached garage with the 4th bedroom and 3rd full bath over top. The oversized lot offers space for you to create your private oasis

    Kathleen Higginbotham Keller Williams Flagship

    314 Thomas White Blvd, Chester, MD 21619
  • 9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    /48

    $425,000

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

    9B Queen Victoria Way, Chester, MD 21619

    This 1680 sq ft , 2 1/2 story townhome & this community have it all! It features many updates within the last year. It is "move-in ready",!.. The updates include a new main-level half bath & a new full bathroom on the top level, both have new flooring, ADA-compliant toilets, new vanity/sink & faucets, and paint. Interior doors are 6 panel colonial replaced in 2024! The main level features new

    Melanie Mcknight RE/MAX Professionals

    9B Queen Victoria Way, Chester, MD 21619
  • 255 Sailcloth Way, Chester, MD 21619
    255 Sailcloth Way, Chester, MD 21619
    255 Sailcloth Way, Chester, MD 21619
    /56

    $950,000

    • 4 Beds
    • 4 Baths
    • 3,450 Sq Ft

    255 Sailcloth Way, Chester, MD 21619

    Welcome to 255 Sailcloth Way in Chester’s premier 55+ community—K. Hovnanian’s Four Seasons at Kent Island. This upgraded Santorini model is perfectly situated on a cul-de-sac premium lot and features 4 bedrooms, 4 full baths, and double primary suites—ideal for multigenerational living or hosting guests in comfort. Enjoy high-end finishes throughout, including LVP flooring, a chef’s kitchen with

    Kathleen Higginbotham Keller Williams Flagship

    255 Sailcloth Way, Chester, MD 21619
  • 162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    /37

    $1,195,000

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft

    162 Kirwans Landing Ln, Chester, MD 21619

    Welcome to 162 Kirwans Landing Lane—a beautifully updated residence located in the sought-after, water-privileged community of Kirwans Landing. Set on 1.4 private acres, this 4-bedroom, 2.5-bath home offers a seamless blend of refined comfort and exceptional outdoor living.Inside, you’ll find hardwood floors throughout both levels, a renovated kitchen with granite countertops, custom

    Brad Kappel TTR Sotheby's International Realty

    162 Kirwans Landing Ln, Chester, MD 21619
  • 224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    /47

    $619,900

    • 2 Beds
    • 2 Baths
    • 1,913 Sq Ft

    224 Bayberry Dr, Chester, MD 21619

    Discover the charm of this meticulously maintained, one-owner Donegal model nestled in the highly desirable, water-privileged 55+ community of Four Seasons at Kent Island. This stunning single-family home features an expansive open-concept layout, enhanced with designer lighting and custom finishes that elevate the home's ambiance.Step into a spacious kitchen that serves as the heart of

    Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
  • 312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    /39

    $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

    Judith Brown Samson Properties

    312 Blenny Ln, Chester, MD 21619
  • 49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    /79

    $529,250

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    49 Queen Guinivere Way, Chester, MD 21619

    Welcome to Queens Landing, where resort-style living meets the comfort of home. This beautifully updated townhome offers 1,440 square feet of thoughtfully designed living space plus an open sunroom, adding approximately 160 additional square feet, creating a seamless and spacious floor plan ideal for everyday living and entertaining.Enjoy panoramic water views from every room - lake and

    Julia Stevens Realty Navigator

    49 Queen Guinivere 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
    /68

    $499,000

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

    15 Queen Anne Way Unit E, Chester, MD 21619

    The BIGGEST price drop yet!! Wake up to shimmering Chester River views and let every day feel like a getaway!This beautifully maintained 2.5-level townhome offers 1,680 square feet of stylish and functional living space in the sought-after waterfront community of Queens Landing. The main level features a cozy living area with a gas fireplace, luxury vinyl plank flooring, and access to a

    Julia Stevens Realty Navigator

    15 Queen Anne Way Unit E, Chester, MD 21619
  • 242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
    /36

    $705,000

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    242 Peregrine Dr, Chester, MD 21619

    AVAILABLE IMMEDIATELY! Introducing the Simone – Where Modern Comfort Meets Farmhouse Charm. This 6 month old Simone offers the perfect blend of open-concept living and timeless Farmhouse style with 4 spacious bedrooms, 3 full baths, and a 2-car garage, this home is designed with both functionality and flair. Step inside to find stylish laminate flooring flowing through the foyer, hallways,

    Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Chester, MD 21619
  • 132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    /77

    $750,000

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    132 Claiborne St, Chester, MD 21619

    Sitting pretty on one of the largest, level lots in the prestigious Gibson's Grant Community, w/ beautiful landscaping, flowers now blooming, and a lawn irrigation system. The lot is enhanced with landscape lighting and a wood fence. This front porch Chatham model is inviting w/sidewalk extension and has a good view of the peaceful pond and natural surroundings. The foyer and main level have

    Melanie Mcknight RE/MAX Professionals

    132 Claiborne St, Chester, MD 21619
  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /49

    $788,000

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1868 Roberta Dr, Chester, MD 21619

    Price improvement.Welcome to this exceptional custom-built home by Lacrosse Builders, nestled in a desirable water-oriented community with partial water views. Designed for comfort, function, and style, this home offers high-end finishes, generous spaces, and thoughtful upgrades throughout.Step inside to find 9’ ceilings on the main level, expansive 6’ windows that fill the home with

    David Kaufmann Eastern Shore Real Estate, LLC

    1868 Roberta Dr, Chester, MD 21619
  • 629 Warbler Way, Chester, MD 21619
    629 Warbler Way, Chester, MD 21619
    629 Warbler Way, Chester, MD 21619
    /11

    $709,900 New Construction

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

    629 Warbler Way, Chester, MD 21619

    Open kitchen, dining area, and great room.Kitchen with Statuary Classique quartz central island.Great room with fireplace for cozy gatherings.Screened patio off great room extends living space.Primary suite with elegant ceiling treatment.Primary bath with dual freestanding vanities.Private home office tucked away from main living areas.

    Builder Photo

    K. Hovnanian Homes

    Builder

    629 Warbler Way, Chester, MD 21619
  • 509 Warbler Way, Chester, MD 21666
    509 Warbler Way, Chester, MD 21666
    509 Warbler Way, Chester, MD 21666
    /22

    $709,900 New Construction

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

    509 Warbler Way, Chester, MD 21666

    Polished kitchen featuring Brellin White cabinets & Statuary Classique quartz countertops.Spacious great room with high vaulted ceiling & cozy fireplace.Organized home office for studying or reading.Lavish primary suite & bath featuring dual vanities & walk-in closet.Versatile screened patio for relaxing with friends.Functional 2-car garage for vehicles & tools.

    Builder Photo

    K. Hovnanian Homes

    Builder

    509 Warbler Way, Chester, MD 21666
  • 164 Redstart Dr, Chester, MD 21619
    164 Redstart Dr, Chester, MD 21619
    164 Redstart Dr, Chester, MD 21619
    /25

    $874,900 New Construction

    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    164 Redstart Dr, Chester, MD 21619

    Polished kitchen featuring Brellin White stacked cabinets & quartz countertops.Cozy fireplace adds warmth & character to spacious great room.Tranquil primary suite with generous walk-in closet.Productive home office for studying or reading.Private Extra Suite, great for overnight guests.Inviting screened patio for spending time with friends.Convenient 3-car tandem garage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    164 Redstart Dr, Chester, MD 21619
  • 131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    /14

    $691,900 New Construction

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

    Simone Plan at K. Hovnanian’s® Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private bedroom 2 located off foyer for overnight guests. Striking kitchen with large island and plenty of counter space. Open and airy great room with slider to covered patio. Convenient covered patio with screened patio option. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities. Versatile loft on second floor with 2 secondary

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • 131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    /12

    $626,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    Bernstein II Plan at K. Hovnanian’s® Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Elegant foyer welcoming guests to your home. Convenient single-story living. Kitchen with spacious pantry and oversized island. Open-concept great room and dining area adjacent to kitchen. Private primary suite with large walk-in closet and spa bath. Laundry room and HovHall with plenty of space to store and organize.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36492116, Chester, MD 21619
  • 1033 Dundee Ct Unit 5, Chester, MD 21619
    1033 Dundee Ct Unit 5, Chester, MD 21619
    1033 Dundee Ct Unit 5, Chester, MD 21619
    /63

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,360 Sq Ft

    1033 Dundee Ct Unit 5, Chester, MD 21619

    Welcome to easy Eastern Shore living in this beautifully renovated 3 Bedroom, 2.5 Bath Townhouse Condo with water privileges, just minutes from the Bay Bridge! Updated top to bottom in 2023, this home is truly move-in ready! Enjoy peaceful mornings on the spacious screened-in porch, complete with bonus storage space, and spend afternoons at the community pier on scenic Piney Creek—perfect

    Erin Anderson Chesapeake Real Estate Associates, LLC

    1033 Dundee Ct Unit 5, Chester, MD 21619
  • 203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    /53

    $499,999 Open Sun 12PM - 2PM

    • 3 Beds
    • 1.5 Baths
    • 2,072 Sq Ft

    203 Barren Ridge Rd, Chester, MD 21619

    Price Improvement- very motivated sellers!!! Nestled in the tranquil community of Chester, Maryland, 203 Barren Ridge Road offers a unique blend of coastal charm and suburban comfort. This inviting Colonial-style home, situated on a 0.31-acre lot, features three bedrooms and one and a half bathrooms, providing ample space for living and entertaining both in and outdoors. With a spacious living

    Beth Bearinger Keller Williams Gateway LLC

    203 Barren Ridge Rd, Chester, MD 21619
  • 315 Cross Creek Ct, Chester, MD 21619
    315 Cross Creek Ct, Chester, MD 21619
    315 Cross Creek Ct, Chester, MD 21619
    /43

    $585,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,374 Sq Ft

    315 Cross Creek Ct, Chester, MD 21619

    You are going to love this bright and spacious home providing almost 2400 feet of living space. Fabulous floor plan with architectural accents that are sure to please. Hardwood floors greet and carry you through the main level, seamlessly connecting the living areas.The bright kitchen overlooks the family room and boasts gorgeous Quartz counter tops, a stylish subway back splash,

    Jimmy White Long & Foster Real Estate, Inc.

    315 Cross Creek Ct, Chester, MD 21619
  • 1405 Little Creek Rd, Chester, MD 21619
    1405 Little Creek Rd, Chester, MD 21619
    /2

    $19,500

    • 2 Beds
    • 1 Bath
    • 764 Sq Ft

    1405 Little Creek Rd, Chester, MD 21619

    This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.Please note that

    Dustin Parker The Parker Group

    1405 Little Creek Rd, Chester, MD 21619
  • 2723 Cox Neck Rd, Chester, MD 21619
    2723 Cox Neck Rd, Chester, MD 21619
    2723 Cox Neck Rd, Chester, MD 21619
    /41

    $473,900

    • 4 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    2723 Cox Neck Rd, Chester, MD 21619

    Harbor View - 100% Financing is Available!!!This newly constructed home features 4 bedrooms and 2.5 baths. Offering a first-floor bedroom or this would be a great office as well. Inside, enjoy the warmth of upgraded LYP floors that flow seamlessly throughout the first floor living spaces and bathrooms, and upgraded carpet throughout the second-floor bedrooms. The kitchen features granite

    Linda Austin Long & Foster Real Estate, Inc.

    2723 Cox Neck Rd, Chester, MD 21619
  • 25 Queen Elizabeth Ct, Chester, MD 21619
    25 Queen Elizabeth Ct, Chester, MD 21619
    25 Queen Elizabeth Ct, Chester, MD 21619
    /39

    $569,000

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

    25 Queen Elizabeth Ct, Chester, MD 21619

    Experience breathtaking sunrises over the Chester River and Chesapeake Bay from this beautifully updated, three-level townhouse-style condo. Located in a serene waterfront community, this home offers the perfect blend of modern amenities and natural beauty. The front entrance welcomes you with a porcelain-tile foyer and a river-rock inset, leading into an open living area with stunning water

    Evguenia Mathur Samson Properties

    25 Queen Elizabeth Ct, Chester, MD 21619
  • 1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    /26

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft

    1872 Harbor Dr, Chester, MD 21619

    This renovated brick rancher, in the sought after Harbor View Community, is ready for its next owner. Perfectly positioned on a double corner lot on nearly 3/4 of an acre. Summer is beginning to wind down but don't worry there’s still time to settle into this move in ready home before the new school year begins. Located in the sought-after Matapeake Elementary School district the double lot

    Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • 1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    /19

    $299,000

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

    1906 Harbor Dr, Chester, MD 21619

    Great opportunity for a savvy investor to buy way below market value. This 3 brm 2 ba rancher, can easily be converted to a 4 brm. Needs work! Sold Strictly AS IS. Seller never occupied the property, therefore cannot guarantee accuracy in this listing, especially regarding utilities, well and sewer. Buyer must do their own due diligence before submitting an offer.

    Alex Fox Allfirst Realty, Inc.

    1906 Harbor Dr, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Annes County Chester

Real Estate & Homes for Sale in Chester, MD

Why Live in Chester

Chester, MD, located on Kent Island between the Chester River and Chesapeake Bay, offers a blend of coastal charm and modern convenience. The area is known for its maritime atmosphere, with numerous marinas and waterfront views. Chester is 17 miles from Annapolis, home to the United States Naval Academy. Outdoor enthusiasts can enjoy Terrapin Nature Park's walking paths and tidal marshes, or the Cross Island Trail for hiking and cycling. Castle Marina provides opportunities for boating and fishing. Indoor fitness options include Club One Fitness and Aerobics. Housing in Chester ranges from ranch-style homes and colonials to New Traditional builds, with properties south of Highway 50 dating back to the mid-20th century and newer developments in the north. The area features a mix of single-family homes, condos, and townhouses, with some waterfront estates requiring additional flood insurance. Annual events like the Kent Island Crab Feast and the Annapolis Baygrass Music Festival foster community spirit. Shopping and dining are centered around Highway 50, with big-box stores like Safeway and Target, and bayside dining options in nearby Kent Narrows, including The Jetty and Bridges. Chester's schools are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving commendable scores. Highway 50 is the main transportation route, connecting Chester to Annapolis, Baltimore, and Washington, D.C., while BWI International Airport is about 30 miles away.

Learn more about living in Chester

Frequently Asked Questions

What is the average home price in Chester, MD?
Homes for sale in Chester, MD have an average home price of $607,136.
Are home prices dropping in Chester?
Yes, home prices in Chester are down 13% in the last 12 months.
How many homes have sold over the last 12 months in Chester, MD?
111 homes have sold in Chester, MD over the last 12 months.
What are the most popular zip codes in Chester, MD?
The most popular zip codes in Chester, MD include 21619, 21666, 21638, 21658 and 21409.
What are the most popular neighborhoods in Chester, MD?
The most popular neighborhood in Chester, MD with the most homes for sale is Kent Narrows.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $637,900. If you put a 20% down payment of $127,600 and had a 30-year fixed mortgage with an interest rate of 6.63%, your estimated principal and interest payment would be $3,270 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $140K a year to afford the median home price in Chester.
How are the schools in Chester, MD?
Chester, MD has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Bayside Elementary School, Matapeake Middle School and Stevensville Middle School. The neighborhood in Chester with the highest rated schools is Kent Narrows. Browse all the schools in Chester, MD to learn more.

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 41 days on the market compared to the national average of 70 days. The median sale price for homes in Chester, MD over the last 12 months is $645,000, down 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$645,000
Median Single Family Sale Price
$700,000
Median Townhouse Sale Price
$469,000
Median 2 Bedroom Sale Price
$539,950
Average Price Per Sq Ft
$346
Number of Homes for Sale
13
Last 12 months Home Sales
111
Months of Supply
1.40
Median List Price
$637,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-12%
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