75

Chester, MD Homes for Sale with Garage

Section Image Section Image Section Image
  • 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 deck, built

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    126 Watermans Cove Ln, 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

    Open Sun 12PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 1,899 Sq Ft

    108 Blenny Ln, Chester, MD 21619

    Open House Sunday, Aug 30 from 12-2PM - 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

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    108 Blenny Ln, 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
  • 1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, Chester, MD 21619
    /46

    $599,900

    Open Sun 10:30AM - 12:30PM
    • 3 Beds
    • 3.5 Baths
    • 2,076 Sq Ft

    1012 Auckland Way, Chester, MD 21619

    Experience the best of Kent Island waterfront living in this beautifully appointed home located in the sought-after Bayside community of Chester. Designed for both everyday comfort and effortless entertaining, this residence features an open-concept floor plan with abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen serves as the heart of the home,

    Jerrise Spencer Redfin Corp

    1012 Auckland 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
  • 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
  • 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
  • 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
  • 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

    Tricia Wilson Wilson Realty & Staging LLC

    2855 Cox Neck Rd, Chester, MD 21619
  • 113 Bentons Pleasure Rd, Chester, MD 21619
    113 Bentons Pleasure Rd, Chester, MD 21619
    /2

    $868,000

    • 4 Beds
    • 2.5 Baths
    • 3,168 Sq Ft

    113 Bentons Pleasure Rd, Chester, MD 21619

    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 eat in breakfast area. Formal Dining

    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
  • 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
  • 536 Warbler Way, Chester, MD 21619
    536 Warbler Way, Chester, MD 21619
    536 Warbler Way, Chester, MD 21619
    /12

    $789,990

    New Construction $27K 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
  • 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
  • 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
  • 111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    /37

    $1,200,000

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

    111 Flycatcher Way, Chester, MD 21619

    Beautiful kitchen with wood-stained cabinetry & pendant lighting. Open concept living spaces with vaulted ceiling & elegant fireplace. Private primary suite & bath with generous walk-in closet. Productive home office for working remotely. Secluded Extra Suite, ideal for overnight guests. Stunning screened patio for outdoor entertaining. Attached 3-car tandem garage for vehicles & storage.

    K. Hovnanian Homes Builder
    111 Flycatcher Way, 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

    $729,990

    New Construction $20K 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
  • 313 Thomas White Blvd, Chester, MD 21619
    313 Thomas White Blvd, Chester, MD 21619
    313 Thomas White Blvd, Chester, MD 21619
    /39

    $825,000

    • 4 Beds
    • 2.5 Baths
    • 3,291 Sq Ft

    313 Thomas White Blvd, Chester, MD 21619

    Welcome to 313 Thomas White Boulevard in the sought-after waterfront community of Gibson's Grant on Kent Island. This beautifully maintained Koch-built home offers more than 3,200 square feet of thoughtfully designed living space with four bedrooms, two-and-a-half baths, and a flexible floor plan tailored to today's lifestyle. The main level features hardwood flooring,crown molding and refined

    Carol Snyder Monument Sotheby's International Realty

    313 Thomas White Blvd, Chester, MD 21619
  • 330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    /50

    $5,400,000

    $500K PRICE DROP
    • 7 Beds
    • 9 Baths
    • 10,667 Sq Ft

    330 Serenity Ln, Chester, MD 21619

    Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit

    Brad Kappel TTR Sotheby's International Realty

    330 Serenity Ln, 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

    $525,000

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

    230 Switchgrass Way Unit 12, Chester, MD 21619

    Welcome to resort-style living at K. Hovnanian's Four Seasons at Kent Island — one of the Eastern Shore's premier 55+ waterfront communities on the Chesapeake Bay. This Magothy model condo offers approximately 2003 sq. ft. of thoughtfully designed single-level living, featuring 2 bedrooms — each with its own attached bathroom — plus a powder room for guests, a private home office with French

    David Moore Real Broker, LLC

    230 Switchgrass Way Unit 12, 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 - 2PM $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
    /48

    $525,000

    $10K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft

    205 Anchor Ln, Chester, MD 21619

    Welcome to 205 Anchor Lane, a spacious and versatile home in the desirable Castle Marina community of Chester! Situated on a generous half-acre lot with no HOA, this oversized split foyer offers the flexibility, space, and location that today's buyers are looking for.With 5 bedrooms and 3 full bathrooms, this home provides room for everyone. The lower level offers excellent potential for

    Kathleen Higginbotham Samson Properties

    205 Anchor Ln, Chester, MD 21619
  • 2702 Sherman Dr, Chester, MD 21619
    2702 Sherman Dr, Chester, MD 21619
    2702 Sherman Dr, Chester, MD 21619
    /65

    $989,000

    • 5 Beds
    • 4 Baths
    • 2,752 Sq Ft

    2702 Sherman Dr, Chester, MD 21619

    Discover the extraordinary waterfront oasis of 2702 Sherman Dr. in Chester. This remarkable residence, featuring 5 bedrooms, 2 full bathrooms, and 2 half bathrooms, has undergone a stunning renovation, creating a haven of luxury and serenity on a peaceful street. Every detail of this home has been impeccably updated, from the oversized windows to the modernized bathrooms. However, the true

    Justin Kennedy Samson Properties

    2702 Sherman Dr, Chester, MD 21619
  • 211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    /19

    $739,900

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

    211 Switchgrass Way Unit 31, Chester, MD 21619

    Striking gourmet kitchen with designer cabinets & chef-worthy island.Elegant dining area featuring fancy dry bar.Refined great room featuring stunning fireplace.Serene owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish shower.Wonderful balcony for relaxing outdoors.

    K. Hovnanian Homes Builder
    211 Switchgrass Way Unit 31, Chester, MD 21619
  • 102 Boatswain Way Unit 2911, Chester, MD 21619
    102 Boatswain Way Unit 2911, Chester, MD 21619
    102 Boatswain Way Unit 2911, Chester, MD 21619
    /56

    $619,990

    New Construction $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 2911, Chester, MD 21619

    Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces.The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets,

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2911, Chester, MD 21619
  • 111 Marshgrass Way Unit 41, Chester, MD 21619
    111 Marshgrass Way Unit 41, Chester, MD 21619
    111 Marshgrass Way Unit 41, Chester, MD 21619
    /56

    $998,000

    • 3 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 41, Chester, MD 21619

    Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional

    Meg Moran Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 41, Chester, MD 21619
  • 247 Redstart Dr, Chester, MD 21619
    247 Redstart Dr, Chester, MD 21619
    247 Redstart Dr, Chester, MD 21619
    /25

    $899,990

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

    247 Redstart Dr, Chester, MD 21619

    Efficient kitchen featuring white cabinetry, corner pantry, & vast island.Cozy fireplace adds warmth & character to expansive great room.Serene primary suite with feature wall & stylish ceiling treatment.Refreshing primary bath featuring matte black finishes & walk-in closet.Formal home office provides a quiet space to work remotely.Versatile screened patio for relaxing with

    K. Hovnanian Homes Builder
    247 Redstart Dr, Chester, MD 21619
  • 233 Cross Creek Ct, Chester, MD 21619
    233 Cross Creek Ct, Chester, MD 21619
    233 Cross Creek Ct, Chester, MD 21619
    /46

    $569,900

    • 4 Beds
    • 2.5 Baths
    • 2,332 Sq Ft

    233 Cross Creek Ct, Chester, MD 21619

    OPEN SATURDAY 12-3PM. Kent Island Living at Its Best! Welcome to this stunning colonial-style home nestled in the desirable Clayborne Woods community in Chester. Offering 2,332 square feet of thoughtfully designed living space, this beautifully maintained residence blends elegance with modern updates and everyday comfort. From the inviting covered front porch with newly replaced fiberglass

    Christopher Nagel Rory S. Coakley Realty, Inc.

    233 Cross Creek Ct, 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
    /13

    $701,990

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

    Simone Plan at 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

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • 117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    /24

    $1,200,000

    New Construction $200K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    117 Flycatcher Way, Chester, MD 21619

    Formal dining room off the foyer for hosting celebrations. Breathtaking kitchen with stacked grey cabinetry & glass uppers. Sprawling quartz island perfect for prep & dining. Vaulted ceiling with ceiling beams connects dining area and great room. Elegant fireplace and sliding door to screened patio in great room. Private home office for working remotely. Primary suite & bath with dual vanities

    K. Hovnanian Homes Builder
    117 Flycatcher Way, Chester, MD 21619
  • 214 Bayberry Dr, Chester, MD 21619
    214 Bayberry Dr, Chester, MD 21619
    214 Bayberry Dr, Chester, MD 21619
    /68

    $924,000

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

    214 Bayberry Dr, Chester, MD 21619

    Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary

    Jim Corson Benson & Mangold, LLC

    214 Bayberry Dr, Chester, MD 21619
  • 208 Blenny Ln Unit 100, Chester, MD 21619
    208 Blenny Ln Unit 100, Chester, MD 21619
    208 Blenny Ln Unit 100, Chester, MD 21619
    /32

    $374,900

    Open Sun 12PM - 2PM $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
  • 203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    /63

    $989,800

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 3,036 Sq Ft

    203 Riverside Dr, Chester, MD 21619

    Construction Complete, QUICK MOVE IN! Coastal luxury living by Laine Street Homes, this exceptional waterfront home offers over 3,000 square feet on 3 levels with 5 bedrooms, 3.5 bathrooms, and stunning water views. Perfectly positioned and thoughtfully designed to capture beautiful sunrises over the water, the home is filled with natural light and showcases panoramic water views from the main

    Chrissy Schultz Long & Foster Real Estate, Inc.

    203 Riverside Dr, Chester, MD 21619
  • 121 Merlin Dr, Chester, MD 21619
    121 Merlin Dr, Chester, MD 21619
    121 Merlin Dr, Chester, MD 21619
    /84

    $697,900

    $22K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,118 Sq Ft

    121 Merlin Dr, Chester, MD 21619

    Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay.Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a cozy gas fireplace, upgraded trim and designer feature walls. Thoughtful

    Yael Beckman Coldwell Banker Realty

    121 Merlin Dr, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Anne's County

Homes for Sale with Garage in Chester, MD

Home Prices in Chester, MD

The median home sale price in Chester, MD is $672,400, up 13% year-over-year. Homes in Chester sell in 369 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$672,400
Median Single Family Sale Price
$772,495
Median Townhouse Sale Price
$365,000
Median 2 Bedroom Sale Price
$625,000
Median 1 Bedroom Sale Price
$240,000
Average Price Per Sq Ft
$303
Number of Homes for Sale
90
Last 12 months Home Sales
222
Months of Supply
4.90
Median List Price
$714,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
13%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 75 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Chester, MD and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group