59

Chester, MD Homes for Sale with Garage

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  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /42

    $749,500 Open Sun 12PM - 2PM

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

    1868 Roberta Dr, Chester, MD 21619

    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 room transitions seamlessly into a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 446-2477

    1868 Roberta Dr, 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
  • 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
    • 2,795 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 amenities.

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset Ln, 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

    $752,990 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 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    /12

    $499,990 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

    $819,990 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

    $848,990 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

    $669,990 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
  • 1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    /23

    $485,000 Open Sat 11AM - 1PM

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

    1872 Harbor Dr, Chester, MD 21619

    Harbor View Community | Corner Lot | Renovated Rancher with Room to GrowWelcome to 1872 Harbor Drive —a move-in ready ranch-style home that offers the space and updates today’s buyers are searching for. Located in the Matapeake Elementary School district, this home sits on a rare double corner lot with nearly three-quarters of an acre, making it a standout opportunity on Maryland’s Eastern

    Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • 102 Warbler Way Unit 2912, Chester, MD 21619
    102 Warbler Way Unit 2912, Chester, MD 21619
    102 Warbler Way Unit 2912, Chester, MD 21619
    /63

    $649,990 New Construction

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

    102 Warbler Way Unit 2912, Chester, MD 21619

    Welcome to the Magothy, 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 Warbler Way Unit 2912, 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

    $499,990 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
  • 311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    /40

    $899,990 New Construction

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

    311 Kingfisher Ln, Chester, MD 21619

    The Tuscaloosa, located on Lot 588, is scheduled for an April 2026 settlement and offers generous space with 5 bedrooms, 4.5 baths, and a 3-car garage—ideal for growing households and effortless entertaining. Designed with both comfort and function in mind, this home includes a private home office, a screened patio for relaxed outdoor living, and a striking stone fireplace complemented by ceiling

    Mary Anne Kowalewski KOVO Realty

    311 Kingfisher Ln, Chester, MD 21619
  • 0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    /12

    $519,900 New Construction

    • 1,250 Sq Ft

    0 Harbor Dr, Chester, MD 21619

    House is now substantially constructed. Builder has finished the lower level and included a bathroom! Lots of extra space and upgrades at this new home! Settle in 30-60 days. LVP floors, granite countertops, stainless steel appliances, etc.

    DJ Dauses Coldwell Banker Waterman Realty

    0 Harbor Dr, Chester, MD 21619
  • 2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    /83

    $750,000

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

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    HERE IT IS! This Rare Luxurious Severn Penthouse, available immediately, offers a lifestyle that seamlessly blends comfort and elegance. Built in 2020, this beautifully maintained residence showcases an open floor plan with windows throughout that invite natural light to dance across its spacious interiors, creating a warm, inviting atmosphere. Step into the heart of the home, where a stunning

    Veronica Lawson Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • 121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    /41

    $1,099,990 New Construction

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

    121 Kinglet Ct, Chester, MD 21619

    Efficient kitchen featuring white cabinetry & quartz countertops. Open concept living area with vaulted ceiling & cozy fireplace. Pristine primary suite with stylish feature wall & ceiling treatment. Refreshing primary bath featuring a freestanding tub & brushed nickel finishes. Private Extra Suite & home office off foyer. Inviting screened patio for relaxing with friends. Attached 3-car tandem

    K. Hovnanian Homes Builder
    121 Kinglet Ct, Chester, MD 21619
  • 102 Warbler Way Unit 2934, Chester, MD 21619
    102 Warbler Way Unit 2934, Chester, MD 21619
    102 Warbler Way Unit 2934, Chester, MD 21619
    /44

    $989,990 New Construction

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

    102 Warbler Way Unit 2934, 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 2934, Chester, MD 21619
  • 110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    /40

    $899,990 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
  • 539 Warbler Way, Chester, MD 21619
    539 Warbler Way, Chester, MD 21619
    539 Warbler Way, Chester, MD 21619
    /27

    $789,990 New Construction

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

    539 Warbler Way, Chester, MD 21619

    Elegant kitchen featuring white cabinetry & pendant lighting. Vast center island, perfect for prepping family meals. Cozy fireplace adds character & warmth to spacious great room. Lavish primary suite & bath featuring generous walk-in closet. Secluded Extra Suite for overnight guests. Functional home office with barn doors for added privacy. Inviting covered patio for outdoor relaxation. Attached

    K. Hovnanian Homes Builder
    539 Warbler Way, Chester, MD 21619
  • 307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    /29

    $979,990 New Construction

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

    307 Kingfisher Ln, Chester, MD 21619

    Welcoming foyer leads to beautiful open concept floorplan. Inviting kitchen featuring white cabinetry, quartz countertops, & center island. Spacious great room with cozy fireplace, perfect for spending time with family. Tranquil primary suite featuring detailed ceiling treatment. Polished primary bath with brushed nickel finishes & generous walk-in closet. Convenient Extra Suite & home office off

    K. Hovnanian Homes Builder
    307 Kingfisher Ln, 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
  • 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

    $699,990 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
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /47

    $425,000 Open Sun 12PM - 2PM

    • 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
  • 110 Boatswain Way Unit 3041, Chester, MD 21619
    110 Boatswain Way Unit 3041, Chester, MD 21619
    110 Boatswain Way Unit 3041, Chester, MD 21619
    /44

    $949,990 New Construction

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

    110 Boatswain Way Unit 3041, 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 November 2026, this home combines modern style with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. The owner’s suite includes a sitting room and large walk-in closets, providing a

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3041, Chester, MD 21619
  • 230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    /67

    $694,500

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

    230 Switchgrass Way Unit 21, Chester, MD 21619

    --------------------------------------EXCEPTIONAL PANORAMIC VIEWS -------------------------------------Immediate Move In Ready. Nature, water and sunshine abound in this beautifully situated, stunning 3BR corner unit at Four Seasons. Flexible closing available. South, west and north exposures through 17 windows and two sets of sliding doors assure that this condo is drenched in sunshine, water

    Lawrence Doyle Long & Foster Real Estate, Inc.

    230 Switchgrass Way Unit 21, Chester, MD 21619
  • 204 Ringneck Ct, Chester, MD 21619
    204 Ringneck Ct, Chester, MD 21619
    204 Ringneck Ct, Chester, MD 21619
    /29

    $324,900

    • 1,747 Sq Ft

    204 Ringneck Ct, Chester, MD 21619

    Price improvement just in time for the spring market!Come see all of amazing amenities this water privileged community has! Enjoy the boating, pool, restaurants and Cross Island trail all within walking distance of this great home! 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

    Mary Wagner Cummings & Co. Realtors

    204 Ringneck Ct, Chester, MD 21619
  • 312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    /48

    $479,000

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    312 Blenny Ln, Chester, MD 21619

    You don't want to miss the opportunity to enjoy Island Living in this maintenance free Pond View End Unit! Come enjoy Island Living in the Bayside Community. Offering Pond Views from every window in this sought after end unit home complete with beautiful landscaping. Relax on your spacious deck overlooking the pond complete with 2 fountains or invite family and friends to enjoy a cookout on your

    Judith Brown EXP Realty, LLC

    312 Blenny Ln, 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
  • 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

    $889,990 New Construction

    • 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
  • 2613 Cecil Dr, Chester, MD 21619
    2613 Cecil Dr, Chester, MD 21619
    2613 Cecil Dr, Chester, MD 21619
    /52

    $995,000 Open Sat 11:30AM - 1:30PM

    • 5 Beds
    • 3.5 Baths
    • 2,496 Sq Ft

    2613 Cecil Dr, Chester, MD 21619

    Welcome to easy waterfront living on Kent Island. Western exposure to beautiful sunsets. Tucked away on a quiet street, this 5-bedroom, 3.5-bath home offers an open floor plan with new flooring throughout the main living area and upstairs, creating a bright and comfortable space that flows effortlessly for both everyday living and entertaining. Out back, enjoy the beautiful pier, perfect for

    Peter Stark Benson & Mangold, LLC

    2613 Cecil Dr, Chester, MD 21619
  • 131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    /13

    $701,990 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
  • 117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    /24

    $1,400,000 New Construction

    • 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
  • 132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    /45

    $995,000

    • 4 Beds
    • 3.5 Baths
    • 3,634 Sq Ft

    132 Kestrel Ln, Chester, MD 21619

    Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay. From the moment you arrive, the covered front

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, Chester, MD 21619
  • 169 Harrier Way, Chester, MD 21619
    169 Harrier Way, Chester, MD 21619
    169 Harrier Way, Chester, MD 21619
    /89

    $779,900

    • 3 Beds
    • 2 Baths
    • 2,394 Sq Ft

    169 Harrier Way, Chester, MD 21619

    Look no further—welcome to the prestigious 55+ resort-style community of Four Seasons at Kent Island, where refined living meets effortless elegance. This exquisitely upgraded Killarney model offers over 2,300 square feet of thoughtfully designed single-level living, featuring an open-concept layout and high-end finishes throughout.At the heart of the home is a stunning gourmet kitchen,

    Dorothea Slaughter Century 21 Redwood Realty

    169 Harrier 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

    $664,900 Open Sun 12PM - 3PM

    • 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
  • 266 Peregrine Dr, Stevensville, MD 21666
    266 Peregrine Dr, Stevensville, MD 21666
    266 Peregrine Dr, Stevensville, MD 21666
    /73

    $728,000

    • 4 Beds
    • 3 Baths
    • 2,870 Sq Ft

    266 Peregrine Dr, Stevensville, MD 21666

    Huge Price Reduction on this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features 4 bedrooms and 3 full baths is awaiting it's next owner. With recent improvements including paint and Plantation Shutters, this home is move in ready so that you can enjoy this community and the upcoming Spring and Summer on

    Edward Beres RE/MAX Executive

    266 Peregrine Dr, Stevensville, MD 21666

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Anne's County Chester

Homes for Sale with Garage in Chester, MD

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 151 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, MD over the last 12 months is $649,900, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$649,900
Median Single Family Sale Price
$685,356
Median Townhouse Sale Price
$375,000
Median 2 Bedroom Sale Price
$549,900
Median 1 Bedroom Sale Price
$297,500
Average Price Per Sq Ft
$299
Number of Homes for Sale
73
Last 12 months Home Sales
207
Months of Supply
4.20
Median List Price
$679,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 59 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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