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Chester, MD Homes for Sale

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  • 126 Watermans Cove Ln, Chester, MD 21619
    126 Watermans Cove Ln, Chester, MD 21619
    126 Watermans Cove 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
  • 2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    /78

    $1,195,000

    $55K PRICE DROP
    • 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

    Agent Photo

    Tricia Wilson

    Wilson Realty & Staging LLC

    2855 Cox Neck Rd, 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
  • 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
  • 231 Evelyne St, Chester, MD 21619
    231 Evelyne St, Chester, MD 21619
    /2

    $815,000

    Coming Soon Sep 30
    • 4 Beds
    • 2.5 Baths
    • 2,870 Sq Ft

    231 Evelyne St, Chester, MD 21619

    This beautiful coastal Colonial home in Gibsons Grant offers a perfect blend of comfort and style. With 4 spacious bedrooms and 2.5 bathrooms, the open floor plan invites warmth and connection. Enjoy cooking up your favorite feast in the upgraded kitchen featuring an island, built-in appliances, and endless countertops. The family room, complete with a propane fireplace, is perfect for gatherings

    Agent Photo

    Tricia Wilson

    Wilson Realty & Staging LLC

    231 Evelyne St, Chester, MD 21619
  • 47 Queen Anne Way, Chester, MD 21619
    47 Queen Anne Way, Chester, MD 21619
    47 Queen Anne Way, 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
  • 1010 Auckland Way, Chester, MD 21619
    1010 Auckland Way, Chester, MD 21619
    1010 Auckland Way, Chester, MD 21619
    /4

    $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
  • 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

    $886,990

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

    Mykonos Plan at Four Seasons at Kent Island - Single Family, 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36477689, 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

    $699,990

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

    Taylor Plan at Four Seasons at Kent Island - Single Family, 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36474700, 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

    $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
  • 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

    $819,990

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

    Kerr Plan at Four Seasons at Kent Island - Single Family, 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.

    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
    /40

    $848,990

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

    Tuscaloosa Plan at Four Seasons at Kent Island - Single Family, 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • 134 Richard Ingle Way, Chester, MD 21619
    134 Richard Ingle Way, Chester, MD 21619
    134 Richard Ingle Way, Chester, MD 21619
    /63

    $749,000

    • 4 Beds
    • 3.5 Baths
    • 2,185 Sq Ft

    134 Richard Ingle Way, Chester, MD 21619

    Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the

    Barbara McCaffrey Redfin Corp

    134 Richard Ingle Way, 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

    $858,990

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

    Franklin Plan at Four Seasons at Kent Island - Single Family, 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • 1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, 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
  • 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
  • 736 Warbler Way Unit 33, Chester, MD 21619
    736 Warbler Way Unit 33, Chester, MD 21619
    736 Warbler Way Unit 33, Chester, MD 21619
    /48

    $719,990

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

    736 Warbler Way Unit 33, Chester, MD 21619

    Home office offers a dedicated space for work or study.Gourmet kitchen centers around a spacious island for prep & gathering.Dry bar adds extra serving space to the dining area.Electric fireplace & balcony make the great room an inviting place to relax or entertain.Walk-in closet keeps wardrobe storage close within the owner's suite.Dual vanities & frameless shower door bring

    K. Hovnanian Homes Builder
    736 Warbler Way Unit 33, Chester, MD 21619
  • 830 Warbler Way Unit 24, Chester, MD 21619
    830 Warbler Way Unit 24, Chester, MD 21619
    830 Warbler Way Unit 24, Chester, MD 21619
    /21

    $749,990

    New Construction $27K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 24, Chester, MD 21619

    Charming gourmet kitchen with designer cabinetry & sprawling island.Elegant dining area with dry bar perfect for hosting.Beautiful great room with electric fireplace for cozy evenings.Private owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish frameless shower.Serene balcony for relaxing outdoors.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 24, 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

    $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
  • 110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    /31

    $699,990

    New Construction $160K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 42, Chester, MD 21619

    Gourmet kitchen with designer cabinetry & vast center island.Inviting great room featuring a cozy electric fireplace.Dry bar creates a polished space for serving & entertaining.Peaceful owner's suite with stylish tray ceiling & private bath.Home office with double doors offers a quiet, flexible workspace.Balcony extends the living space outdoors for relaxing or unwinding.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 42, Chester, MD 21619
  • 113 Bentons Pleasure Rd, Chester, MD 21619
    113 Bentons Pleasure Rd, Chester, MD 21619
    113 Bentons Pleasure Rd, Chester, MD 21619
    /53

    $868,000

    Open Sun 11:30AM - 1:30PM
    • 4 Beds
    • 2.5 Baths
    • 3,168 Sq Ft

    113 Bentons Pleasure Rd, Chester, MD 21619

    OPEN SUNDAY SEPT 20, 11;30;AM-1:30 PM--A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and

    Temple Peirce Cummings & Co. Realtors

    113 Bentons Pleasure Rd, Chester, MD 21619
  • 540 Warbler Way, Chester, MD 21619
    540 Warbler Way, Chester, MD 21619
    540 Warbler Way, Chester, MD 21619
    /27

    $929,990

    New Construction $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    540 Warbler Way, Chester, MD 21619

    Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality.The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    540 Warbler Way, Chester, MD 21619
  • 300 Woods Point Rd, Chester, MD 21619
    300 Woods Point Rd, Chester, MD 21619
    300 Woods Point Rd, Chester, MD 21619
    /78

    $2,840,000

    • 5 Beds
    • 3.5 Baths
    • 1,704 Sq Ft

    300 Woods Point Rd, Chester, MD 21619

    Privacy without isolation - Rare Find - 2 comfy houses on one waterfront property! Each with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod ( 3-bedrooms, 2-bathrooms) recently updated in spring 2026. The former detached garage converted into the guest cottage (2BR, 1.5 BA) has a fabulous screened porch

    Elinor Warring Tidewater Properties

    300 Woods Point Rd, 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
  • 118 Kinglet Ct, Chester, MD 21619
    118 Kinglet Ct, Chester, MD 21619
    118 Kinglet Ct, Chester, MD 21619
    /12

    $969,990

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

    118 Kinglet Ct, Chester, MD 21619

    Home office with sliding doors for added privacy.Vaulted ceiling with stunning beams spans the great room, dining area & kitchen.Fireplace adds a warm focal point to the great room.Screened patio extends directly from the great room.Spacious central island anchors the kitchen.Walk-in closet provides generous storage in the primary suite.Dual freestanding vanities & Plus

    K. Hovnanian Homes Builder
    118 Kinglet 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
  • 536 Warbler Way, Chester, MD 21619
    536 Warbler Way, Chester, MD 21619
    536 Warbler Way, Chester, MD 21619
    /11

    $749,990

    New Construction $67K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    536 Warbler Way, Chester, MD 21619

    Polished kitchen featuring white cabinetry, quartz countertops, & center island.Open concept living areas with a vaulted ceiling & cozy fireplace.Private primary suite featuring a stylish ceiling treatment & walk-in closet.Refreshing primary bath with dual vanities & matte black finishes.Formal home office offers a quiet space for working.Versatile screened patio for relaxing

    K. Hovnanian Homes Builder
    536 Warbler Way, 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
  • 215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    /44

    $995,000

    $105K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    215 Kingfisher Ln, Stevensville, MD 21666

    Check out the Virtual Tour!Exceptional Value in Four Seasons at Kent IslandWhy wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front porch and

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, Stevensville, MD 21666
  • 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
    /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
  • 102 Boatswain Way Unit 2943, Chester, MD 21619
    102 Boatswain Way Unit 2943, Chester, MD 21619
    102 Boatswain Way Unit 2943, Chester, MD 21619
    /47

    $919,990

    New Construction $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 2943, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces.The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2943, Chester, MD 21619
  • 110 Boatswain Way Unit 3042, Chester, MD 21619
    110 Boatswain Way Unit 3042, Chester, MD 21619
    110 Boatswain Way Unit 3042, Chester, MD 21619
    /47

    $699,990

    New Construction $50K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 3042, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces.The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    110 Boatswain Way Unit 3042, Chester, MD 21619
  • 230 Switchgrass Way Unit 12, Chester, MD 21619
    230 Switchgrass Way Unit 12, Chester, MD 21619
    230 Switchgrass Way Unit 12, 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
  • 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
  • 205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, 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

Showing Results 1 - 40, Page 1 of 3

Maryland Queen Anne's County

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

Chester, MD Home Prices vs. Nearby Neighborhoods

Chester, MD Kent Narrows
Median Home Price
$708,445
$762,500
Median Sale Price
$684,500
+14% YoY
$779,000
+19% YoY
Avg. Price per Square Foot
$309
$360
Median Single Family Price
$749,990
$1,300,000
Median Townhouse Price
$374,900
$765,000
Median Condo Price
$669,900
$599,000
Total Active Listings
92 listings
10 listings
Market Conditions
5 Months of Supply
Balanced Market
6 Months of Supply
Balanced Market

Frequently Asked Questions

What is the average home price in Chester, MD?
Homes for sale in Chester, MD have an average home price of $715,284.
How many homes have sold over the last 12 months in Chester, MD?
216 homes have sold in Chester, MD over the last 12 months.
What is the average household income in Chester, MD?
The average household income in Chester, MD is $118K.
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 $708,445. If you put a 20% down payment of $141,700 and had a 30-year fixed mortgage with an interest rate of 6.95%, your estimated principal and interest payment would be $3,750 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $161K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chester is $118K.
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 Kent Island Elementary School. The neighborhood in Chester with the highest rated schools is Kent Narrows. Browse all the schools in Chester, MD to learn more.
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