49

Chester, MD Homes for Sale with Garage

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  • 162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    /41

    $869,000

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

    162 Kirwans Landing Ln, Chester, MD 21619

    Private Waterfront Living in Kirwans Landing!Nestled on 1.4 acres in the water-privileged community of Kirwans Landing, this property offers the perfect blend of privacy, comfort, and resort-style outdoor living. Step outside to your own outdoor oasis, complete with a saltwater pool, spacious deck, and beautifully hardscaped patio surrounded by mature landscaping. A private 90-foot pier,

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 632-6538

    162 Kirwans Landing Ln, Chester, MD 21619
  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $814,900

    • 3 Beds
    • 3 Baths
    • 2,399 Sq Ft

    135 Nauset Ln, Chester, MD 21619

    If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane.Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset 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

    $560,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & 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

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 390-0346

    4000 Herons Nest Way Unit 22, 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

    $494,990 New Construction

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

    Magothy Plan at K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

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

    $818,990 New Construction

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

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

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

    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

    $847,990 New Construction

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

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

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

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • 131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    /24

    $668,990 New Construction

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

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36466218, 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 K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

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

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

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

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

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

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36474700, 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

    $494,990 New Construction

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

    Chester Plan at K. Hovnanian’s® 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
  • 205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    /29

    $535,000

    • 6 Beds
    • 3 Baths
    • 3,500 Sq Ft

    205 Anchor Ln, Chester, MD 21619

    Price Improvement! Need more room? This expansive home is ready to welcome your whole family! With 6 bedrooms, 3 full bathrooms and an over-sized, 4-car garage, there's plenty of space for everyone to spread out and enjoy their own privacy. You'll be delighted by a mix of formal and casual living spaces, including a bright formal living room, a cozy lower-level family room, and a huge screened

    Darlene Winegardner RE/MAX Executive

    205 Anchor Ln, Chester, MD 21619
  • 0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    /12

    $499,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    0 Harbor Dr, Chester, MD 21619

    New home being built! Act now and pick all your colors! Finished models can be seen! Call agent for details.

    DJ Dauses Coldwell Banker Waterman Realty

    0 Harbor Dr, Chester, MD 21619
  • 176 Flagstaff Way Unit 2412, Chester, MD 21619
    176 Flagstaff Way Unit 2412, Chester, MD 21619
    176 Flagstaff Way Unit 2412, Chester, MD 21619
    /63

    $679,990 New Construction

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

    176 Flagstaff Way Unit 2412, Chester, MD 21619

    The Magothy at Lot 2412 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining,

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2412, Chester, MD 21619
  • 176 Flagstaff Way Unit 2433, Chester, MD 21619
    176 Flagstaff Way Unit 2433, Chester, MD 21619
    176 Flagstaff Way Unit 2433, Chester, MD 21619
    /52

    $849,990 New Construction

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

    176 Flagstaff Way Unit 2433, Chester, MD 21619

    The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers planning ahead. This home features 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Standout features include a dedicated home office with lighted French doors, a dry bar

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2433, Chester, MD 21619
  • 311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    /37

    $964,990 New Construction

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

    311 Kingfisher Ln, Chester, MD 21619

    Beautiful kitchen with white 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. Lovely screened patio for outdoor meals or activities. Attached 3-car tandem garage for vehicles & storage.

    K. Hovnanian Homes Builder
    311 Kingfisher Ln, Chester, MD 21619
  • 141 Redstart Dr, Chester, MD 21619
    141 Redstart Dr, Chester, MD 21619
    141 Redstart Dr, Chester, MD 21619
    /25

    $999,990 New Construction

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

    141 Redstart Dr, Chester, MD 21619

    First-floor Extra Suite offers flexible guest accommodations. Home office with sliding barn doors adds charm. Kitchen with white stacked cabinetry & glass-front uppers. Fireplace anchors the great room as a warm focal point. Screened patio off the great room for relaxed outdoor living. Primary suite with decorative feature wall & ceiling treatment. Primary bath with dual freestanding vanities.

    K. Hovnanian Homes Builder
    141 Redstart Dr, Chester, MD 21619
  • 111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    /37

    $1,456,462 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
  • 1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    /32

    $454,900

    • 2 Beds
    • 2 Baths
    • 1,444 Sq Ft

    1401 Calvert Rd, Chester, MD 21619

    MARLING FARMS -Waterviews of Crab Alley Bay - PRICE REDUCED -Brick Rancher- All on ONE LEVEL - Beautifully landscaped 3/4 acre lot that backs to trees - fenced patio area - 2 bedrooms with lots of windows and large closets - 2 full baths, one with a tub, one with a walkin shower - fabulous sunroom addition - quiet office area - updated kitchen with granite counters, newer cabinetry, beverage

    Suzanne Hitt Coldwell Banker Waterman Realty

    1401 Calvert Rd, Chester, MD 21619
  • 110 Warbler Way Unit 3032, Chester, MD 21619
    110 Warbler Way Unit 3032, Chester, MD 21619
    110 Warbler Way Unit 3032, Chester, MD 21619
    /52

    $790,990 New Construction

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

    110 Warbler Way Unit 3032, Chester, MD 21619

    The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 baths, and a 1-car garage. The main living area is anchored by an electric fireplace, while a dry bar adds both function and style for entertaining. A dedicated home office with lighted French doors provides a flexible space

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3032, Chester, MD 21619
  • 190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    /32

    $540,000

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

    190 Harrier Way Unit 11, Chester, MD 21619

    Luxury 55+ Living at Four Seasons on Kent Island – Move-In Ready & Priced to Sell!Welcome to the resort-style lifestyle of Four Seasons on Kent Island, an amenity-rich 55+ waterfront community where luxury, comfort, and convenience meet. Inside, you'll find open-concept layouts filled with natural light, gourmet kitchens with quartz countertops, GE Profile stainless steel

    Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
  • 170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    /79

    $499,000

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

    170 Harrier Way Unit 22, Chester, MD 21619

    Leaves are falling—and so is the price of this stunning condo in the fun, vibrant, and highly sought-after Four Seasons at Kent Island community. Act fast! This is the most breathtaking time of year to make this home yours. As the trees shift from summer green to the rich colors of fall, Mother Nature puts on her finest show. And once the leaves drop, the Chester River opens up before you—right

    Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, Chester, MD 21619
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /47

    $425,000

    • 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
  • 1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    /28

    $499,000

    • 2 Beds
    • 2 Baths
    • 1,900 Sq Ft

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Step into the good life in the sought-after Four Seasons on Kent Island, where low-maintenance living meets waterfront vibes. This 2-bedroom, 2-bath home offers spacious one-level living with an open, airy layout, freshly painted interiors, and a stylish kitchen featuring a modern glass subway tile backsplash—perfect for entertaining or unwinding after a day on the Shore. The 1-car garage plus

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • 203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    /68

    $1,099,900 New Construction

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

    203 Riverside Dr, Chester, MD 21619

    To-be-built 5BR, 3.5BA waterfront home by Laine Street Homes — now under construction and perfectly positioned to capture breathtaking sunrises over the waterfront of Crab Alley Creek. Thoughtfully designed for modern coastal living, this home will offer panoramic water views from the main level and the primary suite, filling the interior with natural light and scenic beauty. The bright layout

    Chrissy Schultz Long & Foster Real Estate, Inc.

    203 Riverside Dr, Chester, MD 21619
  • 204 Ringneck Ct, Chester, MD 21619
    204 Ringneck Ct, Chester, MD 21619
    204 Ringneck Ct, Chester, MD 21619
    /29

    $345,000

    • 3 Beds
    • 3.5 Baths
    • 1,747 Sq Ft

    204 Ringneck Ct, Chester, MD 21619

    Professional pictures to come soon. Just a few shots to give an idea of what is to come! Lovely 3 level townhome in the water oriented community of Bayside Marina offering 2/3 bedrooms and 3 full and one half baths. This multifunctional unit can be two bedrooms up and one down or use the downstairs room with a full bath as a tv or relaxing/entertaining area. Walk out to the patio and enjoy views

    Mary Wagner Cummings & Co. Realtors

    204 Ringneck Ct, Chester, MD 21619
  • 1704 Bayside Dr, Chester, MD 21619
    1704 Bayside Dr, Chester, MD 21619
    1704 Bayside Dr, Chester, MD 21619
    /37

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 1,830 Sq Ft

    1704 Bayside Dr, Chester, MD 21619

    Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautifully renovated 3-bedroom, 2.5 bath home offers an open-concept layout design to capture breathing taking water views that stretch endless across the horizon. Each evening brings magnificent, direct sunset views-- the kind that make you stop, breathe, and take it all in. New pier in 2020! Step inside to

    Alex Hodges Cottage Street Realty LLC

    1704 Bayside Dr, Chester, MD 21619
  • 110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    /38

    $964,990 New Construction

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

    110 Kinglet Ct, Chester, MD 21619

    First-floor Extra Suite with private bath for guest comfort. Home office with sliding barn doors adds character. Kitchen, dining area & great room share a vaulted ceiling with beams. Kitchen with central island highlighted by matte black pendant lighting. Shiplap fireplace with hearth anchors the great room. Screened patio off the great room for relaxed outdoor living. Primary suite with ceiling

    K. Hovnanian Homes Builder
    110 Kinglet 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

    $700,990 New Construction

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

    Simone Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, 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

    $1,100,000 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
  • 200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    /44

    $674,900

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

    200 Harrier Way Unit 21, Chester, MD 21619

    Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway tile

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, Chester, MD 21619
  • 402 Blenny Ln, Chester, MD 21619
    402 Blenny Ln, Chester, MD 21619
    402 Blenny Ln, Chester, MD 21619
    /51

    $399,000

    • 3 Beds
    • 3.5 Baths
    • 1,747 Sq Ft

    402 Blenny Ln, Chester, MD 21619

    End-unit three-level townhome overlooking the pond in Bayside community. Freshly painted, new LVP on lower level. Engineered wood floors on main level. Living room has propane fireplace and built-in bookcases/shelves. Most windows have plantation shutters. Sliding door overlooks rear deck, lower level sliding door overlooks rear patio; both with pond views! Amenity-rich Bayside Community offers

    Thomas Welch Long & Foster Real Estate, Inc.

    402 Blenny Ln, Chester, MD 21619
  • 176 Flagstaff Way Unit 2411, Chester, MD 21619
    176 Flagstaff Way Unit 2411, Chester, MD 21619
    176 Flagstaff Way Unit 2411, Chester, MD 21619
    /63

    $649,990 New Construction

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

    176 Flagstaff Way Unit 2411, Chester, MD 21619

    The Magothy at Lot 2411 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining,

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2411, Chester, MD 21619
  • 110 Warbler Way Unit 3031, Chester, MD 21619
    110 Warbler Way Unit 3031, Chester, MD 21619
    110 Warbler Way Unit 3031, Chester, MD 21619
    /44

    $929,990 New Construction

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

    110 Warbler Way Unit 3031, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3031, Chester, MD 21619
  • 1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    /64

    $1,167,890 New Construction

    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    *****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! 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 lifestyle in this home built for

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
  • 131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    /11

    $773,990 New Construction

    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

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

    Private home office for working from home. Spacious great room with slider to covered patio. Beautiful kitchen with large island and roomy pantry. Luxurious primary suite with triple windows. Relaxing primary bath with spacious shower and walk-in closet. Convenient covered patio with screen patio option.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
  • 176 Flagstaff Way Unit 2443, Chester, MD 21619
    176 Flagstaff Way Unit 2443, Chester, MD 21619
    176 Flagstaff Way Unit 2443, Chester, MD 21619
    /52

    $999,900 New Construction

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

    176 Flagstaff Way Unit 2443, Chester, MD 21619

    The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2443, Chester, MD 21619
  • 259 Redstart Dr, Chester, MD 21619
    259 Redstart Dr, Chester, MD 21619
    259 Redstart Dr, Chester, MD 21619
    /11

    $824,990 New Construction

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

    259 Redstart Dr, Chester, MD 21619

    Kitchen with stacked white cabinetry & glass-front uppers. Great room with fireplace creates a warm focal point. Covered patio off the great room for outdoor living. Primary suite with ceiling treatment adds refined detail. Primary bath with dual freestanding vanities. Home office tucked away for quiet work time. Second-floor loft open to the great room below.

    K. Hovnanian Homes Builder
    259 Redstart Dr, Chester, MD 21619
  • 110 Warbler Way Unit 3021, Chester, MD 21619
    110 Warbler Way Unit 3021, Chester, MD 21619
    110 Warbler Way Unit 3021, Chester, MD 21619
    /44

    $829,990 New Construction

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

    110 Warbler Way Unit 3021, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3021, Chester, MD 21619
  • 131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    /12

    $599,990 New Construction

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

    Bernstein II Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36492116, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Annes County Chester

Homes for Sale with Garage in Chester, MD

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 100 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, MD over the last 12 months is $629,950, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$629,950
Median Single Family Sale Price
$675,438
Median Townhouse Sale Price
$367,450
Median 2 Bedroom Sale Price
$549,900
Median 1 Bedroom Sale Price
$297,500
Average Price Per Sq Ft
$297
Number of Homes for Sale
64
Last 12 months Home Sales
198
Months of Supply
3.90
Median List Price
$649,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 49 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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