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Chester, MD Homes for Sale with Garage

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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 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

    $530,000

    $30K 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 - Price Improvement + Seller to Credit $4000 towards Capital Contribution Fee * 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

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /42

    $724,500

    $45K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1868 Roberta Dr, Chester, MD 21619

    Price improvement! Motivated sellers. This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    1868 Roberta Dr, 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

    $504,990

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

    Magothy Plan at Four Seasons at Kent Island Condos, Chester, MD 21619

    Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owner’s suite with spa bath . Fantastic great room with large windows for your viewing pleasure. Large secondary bedroom with opt. door to access patio. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 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
  • 1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, Chester, MD 21619
    1012 Auckland Way, Chester, MD 21619
    /46

    $599,900

    Open Sat 12PM - 2PM
    • 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
  • 323 Kingfisher Ln, Chester, MD 21619
    323 Kingfisher Ln, Chester, MD 21619
    323 Kingfisher Ln, Chester, MD 21619
    /38

    $974,990

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

    323 Kingfisher Ln, Chester, MD 21619

    Efficient kitchen with gray cabinetry, quartz countertops, & matte black finishes.Open concept living areas featuring a vaulted ceiling, stained beams, & cozy fireplace.Lavish primary suite & plus bath with generous walk-in closet.Private Extra Suite perfect for overnight guests.Formal home office provides a quiet area for studying or reading.Versatile screened patio for

    K. Hovnanian Homes Builder
    323 Kingfisher Ln, 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

    Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades.Welcome to Bayside living at its finest. This meticulously maintained

    David Moore Real Broker, LLC

    807 Auckland Way, Chester, MD 21619
  • 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

    $504,990

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

    Chester Plan at Four Seasons at Kent Island 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
  • 118 Kinglet Ct, Chester, MD 21619
    118 Kinglet Ct, Chester, MD 21619
    118 Kinglet Ct, Chester, MD 21619
    /8

    $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
  • 115 Gibson Cir, Chester, MD 21619
    115 Gibson Cir, Chester, MD 21619
    115 Gibson Cir, Chester, MD 21619
    /42

    $569,900

    $15K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,048 Sq Ft

    115 Gibson Cir, Chester, MD 21619

    Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxurious lifestyle with a perfect blend of comfort and elegance. Built in 2009, this Colonial-style residence spans 2,048 square feet and features two spacious bedrooms , with a another room that could be used for a 3rd bedroom and two and a half bathrooms, making it an ideal retreat for those seeking both

    Lawrence Doyle Long & Foster Real Estate, Inc.

    115 Gibson Cir, Chester, MD 21619
  • 215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    /44

    $1,049,500

    $51K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    215 Kingfisher Ln, Stevensville, MD 21666

    Price Reduced $50K – Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why 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

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, Stevensville, MD 21666
  • 1000 Herons Nest Way Unit 23, Chester, MD 21619
    1000 Herons Nest Way Unit 23, Chester, MD 21619
    1000 Herons Nest Way Unit 23, Chester, MD 21619
    /39

    $490,000

    • 2 Beds
    • 2.5 Baths

    1000 Herons Nest Way Unit 23, Chester, MD 21619

    Welcome to 1000 Herons Nest Way #23, an exceptional former model home located in the first phase of condominiums within the highly desirable Four Seasons at Kent Island. This beautiful 2-bedroom, 2.5-bath residence combines designer finishes, thoughtful upgrades, and a peaceful natural setting to create the perfect low-maintenance retreat. From the moment you enter, you'll appreciate the bright,

    Tara Trout Samson Properties

    1000 Herons Nest Way Unit 23, Chester, MD 21619
  • 7013 Bridgepointe Dr, Chester, MD 21619
    7013 Bridgepointe Dr, Chester, MD 21619
    7013 Bridgepointe Dr, Chester, MD 21619
    /48

    $375,000

    Open Wed 6PM - 8PM
    • 3 Beds
    • 2.5 Baths
    • 1,635 Sq Ft

    7013 Bridgepointe Dr, Chester, MD 21619

    Adorable is the perfect word to describe this beautifully maintained townhome! Freshly painted and featuring a new roof and skylights (2025), this inviting home offers over 1,600 square feet of comfortable living space with three bedrooms, two full baths, and one-half bath.The main level showcases vaulted ceilings with skylights that fill the home with natural light, creating a bright and

    Dee Dee McCracken Coldwell Banker Realty

    7013 Bridgepointe Dr, 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
    /27

    $749,990

    New Construction Open Sat 11AM - 4PM
    • 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 private

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    110 Boatswain Way Unit 3042, Chester, MD 21619
  • 330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    /50

    $5,900,000

    • 7 Beds
    • 9 Baths
    • 9,974 Sq Ft

    330 Serenity Ln, Chester, MD 21619

    Designed to rival a private resort, the outdoor spaces were made for celebrating with family and friends. Sweeping water views set the stage for unforgettable gatherings. The waterfront pool features a cascading natural rock waterfall with a bench tucked underneath and a generous shallow sun shelf. A beautifully appointed pool house offers a covered summer kitchen, bar, seating area and full bath

    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
    /18

    $550,000

    Coming Soon
    • 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 Chester model condo offers approximately 1,900 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
  • 265 Evelyne St, Chester, MD 21619
    265 Evelyne St, Chester, MD 21619
    265 Evelyne St, Chester, MD 21619
    /62

    $620,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,119 Sq Ft

    265 Evelyne St, Chester, MD 21619

    Welcome to 265 Evelyne Street in the sought-after waterfront community of Gibsons Grant! Offering nearly 2,200 square feet of living space, this beautifully maintained home combines coastal charm with modern comfort. Inside, you’ll find engineered hardwood floors, a spacious open-concept layout, and a beautifully appointed kitchen featuring a large island, gas stove, double oven, and plenty of

    Kathleen Higginbotham Samson Properties

    265 Evelyne St, 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 Sat 12PM - 4PM $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
  • 129 Wheelhouse Way Unit 11, Chester, MD 21619
    129 Wheelhouse Way Unit 11, Chester, MD 21619
    129 Wheelhouse Way Unit 11, Chester, MD 21619
    /43

    $585,000

    • 2 Beds
    • 2.5 Baths

    129 Wheelhouse Way Unit 11, Chester, MD 21619

    Buyers got cold feet- Back on Market but won't last long! Priced well below market value! Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury, convenience, and resort-style living come together in a way that few homes in the community can offer. This beautifully upgraded first-floor Magothy model is not only one of the closest residences to the Chester

    Jennifer Thomas RE/MAX Executive

    129 Wheelhouse Way Unit 11, Chester, MD 21619
  • 205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    /48

    $535,000

    • 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
  • 102 Warbler Way Unit 2921, Chester, MD 21619
    102 Warbler Way Unit 2921, Chester, MD 21619
    102 Warbler Way Unit 2921, Chester, MD 21619
    /44

    $869,990

    New Construction $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Warbler Way Unit 2921, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, 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

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2921, 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 bedrooms and full bath.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • 127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    /49

    $900,000

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

    127 Flycatcher Way, Chester, MD 21619

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

    Mary Anne Kowalewski KOVO Realty

    127 Flycatcher Way, Chester, MD 21619
  • 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
  • 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

    $414,900

    $44K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    208 Blenny Ln Unit 100, Chester, MD 21619

    HUGE $20,000 PRICE REDUCTION!! 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

    Pamela Ackermann-Doll RE/MAX Executive

    208 Blenny Ln Unit 100, Chester, MD 21619
  • 121 Merlin Dr, Chester, MD 21619
    121 Merlin Dr, Chester, MD 21619
    121 Merlin Dr, Chester, MD 21619
    /71

    $719,900

    Open Sun 12PM - 3PM
    • 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
  • 1000 Herons Nest Way Unit 43, Chester, MD 21619
    1000 Herons Nest Way Unit 43, Chester, MD 21619
    1000 Herons Nest Way Unit 43, Chester, MD 21619
    /50

    $600,000

    Open Thu 2PM - 4PM
    • 2 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    1000 Herons Nest Way Unit 43, Chester, MD 21619

    Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment.Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center

    Dee Dee McCracken Coldwell Banker Realty

    1000 Herons Nest Way Unit 43, Chester, MD 21619
  • 114 Kinglet Ct, Chester, MD 21619
    114 Kinglet Ct, Chester, MD 21619
    114 Kinglet Ct, Chester, MD 21619
    /25

    $1,009,990

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

    114 Kinglet Ct, Chester, MD 21619

    First-floor Extra Suite adds flexibility for guests or extended living.Home office with sliding doors for added privacy.Crown molding adds a refined touch to the great room & kitchen.Screened patio extends directly from the great room.Stacked cabinetry with glass-front uppers brings layered detail to the kitchen.Decorative feature walls add custom character to the foyer &

    K. Hovnanian Homes Builder
    114 Kinglet Ct, Chester, MD 21619
  • 102 Boatswain Way Unit 2933, Chester, MD 21619
    102 Boatswain Way Unit 2933, Chester, MD 21619
    102 Boatswain Way Unit 2933, Chester, MD 21619
    /52

    $829,990

    New Construction $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 2933, 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 office

    Mary Anne Kowalewski KOVO Realty

    102 Boatswain Way Unit 2933, Chester, MD 21619
  • 315 Bentons Pleasure Rd, Chester, MD 21619
    315 Bentons Pleasure Rd, Chester, MD 21619
    /2

    $629,900

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    315 Bentons Pleasure Rd, Chester, MD 21619

    9999

    Douglas Kayhoe Douglas Realty LLC

    315 Bentons Pleasure Rd, Chester, MD 21619
  • 1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    /64

    $1,281,880

    New Construction
    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    *****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
  • 715 Warbler Way, Chester, MD 21619
    715 Warbler Way, Chester, MD 21619
    715 Warbler Way, Chester, MD 21619
    /15

    $849,990

    New Construction $28K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    715 Warbler Way, Chester, MD 21619

    Stacked cabinetry with glass front uppers brings layered detail to the kitchen.Soaring two-story ceiling adds volume to the great room with a fireplace.Screened patio off the great room extends the living space outdoors.Primary suite features a ceiling treatment with a sliding barn door to the private bath.Primary bath with dual freestanding vanities & plus shower.Home office

    K. Hovnanian Homes Builder
    715 Warbler Way, Chester, MD 21619
  • 124 Riverside Dr, Chester, MD 21619
    124 Riverside Dr, Chester, MD 21619
    124 Riverside Dr, Chester, MD 21619
    /45

    $535,000

    Open Sat 11AM - 1PM $5K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,979 Sq Ft

    124 Riverside Dr, Chester, MD 21619

    OPEN HOUSE SATURDAY 7/18 11-1 REDUCED and unbelievable value at $535,000.Gorgeous, like-new home on Kent Island! VA ASSUMABLE at 2.75% Interest!! Price reduced to $535,000. Clearly under market value. for this close to 2000 square foot , like new home with a large yard backing to trees. Home is 1974 Square foot and looks like new!! Clearly under market value. for this close to 2000 square foot ,

    Christine Schumaker Douglas Realty LLC

    124 Riverside Dr, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Anne's County Chester

Homes for Sale with Garage in Chester, MD

Home Prices in Chester, MD

The median home sale price in Chester, MD is $665,000, up 18% year-over-year. Homes in Chester sell in 304 days on average, compared to the national average of 57 days.

Home Price Trends

Median Sale Price
$665,000
Median Single Family Sale Price
$707,450
Median Townhouse Sale Price
$365,000
Median 2 Bedroom Sale Price
$600,000
Median 1 Bedroom Sale Price
$284,500
Average Price Per Sq Ft
$304
Number of Homes for Sale
91
Last 12 months Home Sales
225
Months of Supply
4.90
Median List Price
$680,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
18%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 58 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.

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