40

Chester, MD Homes for Sale under $1,000,000

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  • 320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    /15

    $859,900

    • 3 Beds
    • 2 Baths
    • 2,331 Sq Ft

    320 Bayberry Dr, Chester, MD 21619

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    320 Bayberry Dr, Chester, MD 21619
  • 231 Evelyne St, Chester, MD 21619
    231 Evelyne St, Chester, MD 21619
    /2

    $815,000

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

    231 Evelyne St, Chester, MD 21619

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

    Agent Photo

    Tricia Wilson

    Wilson Realty & Staging LLC

    231 Evelyne St, Chester, MD 21619
  • 134 Richard Ingle Way, Chester, MD 21619
    134 Richard Ingle Way, Chester, MD 21619
    134 Richard Ingle Way, Chester, MD 21619
    /63

    $749,000

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

    134 Richard Ingle Way, Chester, MD 21619

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

    Barbara McCaffrey Redfin Corp

    134 Richard Ingle Way, Chester, MD 21619
  • 131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    /27

    $858,990

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

    Franklin Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

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

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

    $719,990

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

    736 Warbler Way Unit 33, Chester, MD 21619

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

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

    $749,990

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

    830 Warbler Way Unit 24, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 24, Chester, MD 21619
  • 113 Bentons Pleasure Rd, Chester, MD 21619
    113 Bentons Pleasure Rd, Chester, MD 21619
    113 Bentons Pleasure Rd, Chester, MD 21619
    /53

    $868,000

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

    113 Bentons Pleasure Rd, Chester, MD 21619

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

    Temple Peirce Cummings & Co. Realtors

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

    $929,990

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

    540 Warbler Way, Chester, MD 21619

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

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    540 Warbler Way, Chester, MD 21619
  • 118 Kinglet Ct, Chester, MD 21619
    118 Kinglet Ct, Chester, MD 21619
    118 Kinglet Ct, Chester, MD 21619
    /12

    $969,990

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

    118 Kinglet Ct, Chester, MD 21619

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

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

    $749,990

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

    536 Warbler Way, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    536 Warbler Way, Chester, MD 21619
  • 215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    /44

    $995,000

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

    215 Kingfisher Ln, Stevensville, MD 21666

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

    Jennifer Thomas RE/MAX Executive

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

    $919,990

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

    102 Boatswain Way Unit 2943, Chester, MD 21619

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

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2943, Chester, MD 21619
  • 211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    /19

    $739,900

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

    211 Switchgrass Way Unit 31, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    211 Switchgrass Way Unit 31, Chester, MD 21619
  • 111 Marshgrass Way Unit 41, Chester, MD 21619
    111 Marshgrass Way Unit 41, Chester, MD 21619
    111 Marshgrass Way Unit 41, Chester, MD 21619
    /56

    $998,000

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

    111 Marshgrass Way Unit 41, Chester, MD 21619

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

    Meg Moran Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 41, Chester, MD 21619
  • 275 Warbler Way, Chester, MD 21619
    275 Warbler Way, Chester, MD 21619
    275 Warbler Way, Chester, MD 21619
    /58

    $930,000

    $15K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,761 Sq Ft

    275 Warbler Way, Chester, MD 21619

    Welcome to 275 Warbler Way, a beautifully upgraded Kerr model by K. Hovnanian in the sought-after 55+ Four Seasons at Kent Island community. Less than two years old and already through its one-year builder punch list, this home offers the ease of newer construction without the wait—plus thoughtful upgrades and finishes already in place.Situated on a premium corner lot, this impressive home

    Justin Kennedy Samson Properties

    275 Warbler Way, Chester, MD 21619
  • 247 Redstart Dr, Chester, MD 21619
    247 Redstart Dr, Chester, MD 21619
    247 Redstart Dr, Chester, MD 21619
    /29

    $899,990

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

    247 Redstart Dr, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    247 Redstart Dr, Chester, MD 21619
  • 131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    /13

    $701,990

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

    Simone Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private bedroom 2 located off foyer for overnight guests.Striking kitchen with large island and plenty of counter space.Open and airy great room with slider to covered patio.Convenient covered patio with screened patio option.Luxurious primary suite with oversized walk-in closet.Relaxing primary bath with split vanities.Versatile loft on second floor with 2 secondary

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • 214 Bayberry Dr, Chester, MD 21619
    214 Bayberry Dr, Chester, MD 21619
    214 Bayberry Dr, Chester, MD 21619
    /68

    $924,000

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

    214 Bayberry Dr, Chester, MD 21619

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

    Jim Corson Benson & Mangold, LLC

    214 Bayberry Dr, Chester, MD 21619
  • 114 Kinglet Ct, Chester, MD 21619
    114 Kinglet Ct, Chester, MD 21619
    114 Kinglet Ct, Chester, MD 21619
    /29

    $999,990

    New Construction $10K PRICE DROP
    • 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
  • 830 Warbler Way Unit 43, Chester, MD 21619
    830 Warbler Way Unit 43, Chester, MD 21619
    830 Warbler Way Unit 43, Chester, MD 21619
    /24

    $789,990

    New Construction $30K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 43, Chester, MD 21619

    Private home office with French doors, perfect for leisure activities.Gorgeous gourment kitchen with designer cabinets & vast island.Elegant dining area featuring lovely dry bar.Beautiful great room with sleek electric fireplace.Serene owner's suite featuring access to balcony & large walk-in closet.Lavish owner's spa bath featuring dual sinks.Fabulous balcony for

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 43, 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
    /47

    $819,990

    New Construction $10K 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

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2933, Chester, MD 21619
  • 201 Switchgrass Way Unit 34, Chester, MD 21619
    201 Switchgrass Way Unit 34, Chester, MD 21619
    201 Switchgrass Way Unit 34, Chester, MD 21619
    /41

    $835,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    201 Switchgrass Way Unit 34, Chester, MD 21619

    Welcome to Four Seasons at Kent Island, where luxury waterfront living meets the ease of a premier 55+ lifestyle on the shores of the Chester River. Offering breathtaking, unobstructed water views and exceptional community amenities, this beautifully appointed three-bedroom, two-and-a-half-bath condominium is designed for those who appreciate comfort, elegance, and low-maintenance

    Brad Kappel TTR Sotheby's International Realty

    201 Switchgrass Way Unit 34, Chester, MD 21619
  • 102 Boatswain Way Unit 34, Chester, MD 21619
    102 Boatswain Way Unit 34, Chester, MD 21619
    102 Boatswain Way Unit 34, Chester, MD 21619
    /21

    $969,990

    New Construction $34K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 34, Chester, MD 21619

    Stylish gourmet kitchen centered around a large island. Dining space with convenient dry bar for hosting. Open great room featuring an electric fireplace. Balcony extending from the main living area. Owner’s suite with two spacious walk-in closets. Private sitting area in owner’s suite with balcony connection. Owner’s bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 34, Chester, MD 21619
  • 102 Boatswain Way Unit 32, Chester, MD 21619
    102 Boatswain Way Unit 32, Chester, MD 21619
    102 Boatswain Way Unit 32, Chester, MD 21619
    /35

    $819,990

    New Construction $45K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 32, Chester, MD 21619

    Elegant gourmet kitchen with designer cabinetry & center island.Spacious great room featuring electric fireplace.Charming dining area with dry bar for efficient serving.Serene owner's suite & spa bath with frameless shower door.Convenient home office for working remotely.Peaceful balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 32, 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

    $709,990

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

    Kelly Plan at Four Seasons at Kent Island - Single Family, 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
  • 233 Peregrine Dr, Chester, MD 21619
    233 Peregrine Dr, Chester, MD 21619
    233 Peregrine Dr, Chester, MD 21619
    /63

    $724,999

    $25K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    233 Peregrine Dr, Chester, MD 21619

    Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel

    Michelle Abplanalp Rosendale Realty

    233 Peregrine Dr, Chester, MD 21619
  • 402 Macum Creek Dr, Chester, MD 21619
    402 Macum Creek Dr, Chester, MD 21619
    402 Macum Creek Dr, Chester, MD 21619
    /91

    $789,000

    • 3 Beds
    • 2.5 Baths
    • 2,787 Sq Ft

    402 Macum Creek Dr, Chester, MD 21619

    Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living

    Tara Trout Samson Properties

    402 Macum Creek Dr, Chester, MD 21619
  • 102 Boatswain Way Unit 2932, Chester, MD 21619
    102 Boatswain Way Unit 2932, Chester, MD 21619
    102 Boatswain Way Unit 2932, Chester, MD 21619
    /47

    $819,990

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

    102 Boatswain Way Unit 2932, Chester, MD 21619

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

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2932, Chester, MD 21619
  • 532 Warbler Way, Chester, MD 21619
    532 Warbler Way, Chester, MD 21619
    532 Warbler Way, Chester, MD 21619
    /29

    $899,990

    New Construction $30K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    532 Warbler Way, Chester, MD 21619

    First-floor Extra Suite adds flexibility for guests.Ceiling detail & crown molding carry through the kitchen and great room.Stacked cabinetry with glass-front uppers brings added depth to the kitchen.Fireplace creates a warm focal point in the great room.Screened patio off the great room extends the living space outdoors.Decorative feature walls in the foyer & primary suite

    K. Hovnanian Homes Builder
    532 Warbler Way, 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
    /36

    $700,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River.The gourmet kitchen is the heart of the home,

    Matthew Arnold Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • 209 Harrier Way, Stevensville, MD 21666
    209 Harrier Way, Stevensville, MD 21666
    209 Harrier Way, Stevensville, MD 21666
    /123

    $737,900

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft

    209 Harrier Way, Stevensville, MD 21666

    LESS MONEY OUT OF YOUR POCKET!!! With an accepted contract by 9/30/26 - the sellers are offering up to $7500 toward your closing costs or to use toward a rate buydown if you're financing your purchase! If you're looking for the ease of primarily one-level living with flexible space for guests and hobbies, 209 Harrier Way offers the best of both worlds.*** Barely lived in and offering over $75,000

    Violeta Aguirre Long & Foster Real Estate, Inc.

    209 Harrier Way, Stevensville, MD 21666
  • 102 Boatswain Way Unit 43, Chester, MD 21619
    102 Boatswain Way Unit 43, Chester, MD 21619
    102 Boatswain Way Unit 43, Chester, MD 21619
    /32

    $919,990

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

    102 Boatswain Way Unit 43, Chester, MD 21619

    Beautiful gourmet kitchen featuring designer cabinetry & an efficient layout for everyday living.Bright great room with an electric fireplace adding warmth & character.Dining area complemented by a convenient dry bar for easy entertaining.Private owner’s suite with walk-in closet & direct access to the spa bath.Home office with double doors ideal for work or quiet

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 43, Chester, MD 21619
  • 207 Thomas White Blvd, Chester, MD 21619
    207 Thomas White Blvd, Chester, MD 21619
    207 Thomas White Blvd, Chester, MD 21619
    /96

    $819,900

    • 3 Beds
    • 2.5 Baths
    • 2,479 Sq Ft

    207 Thomas White Blvd, Chester, MD 21619

    Located in the sought-after waterfront community of Gibson’s Grant, this beautiful Koch Homes property features the popular Ashford model, with a first-floor Primary Bedroom enhanced by a three-foot extension. A first-floor study offers flexible space for a home office, den, or possible fourth bedroom. Thoughtfully designed and exceptionally well-maintained, the home offers numerous updates and

    Tim Karns RE/MAX Components

    207 Thomas White Blvd, Chester, MD 21619
  • 736 Warbler Way Unit 2733, Chester, MD 21619
    736 Warbler Way Unit 2733, Chester, MD 21619
    736 Warbler Way Unit 2733, Chester, MD 21619
    /47

    $719,990

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

    736 Warbler Way Unit 2733, Chester, MD 21619

    Welcome to Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in May 2027, this home combines comfort, functionality, and stylish finishes for modern living.The main living area features an electric fireplace, creating a warm and inviting focal point, while a dry bar adds the perfect touch for entertaining. A dedicated home

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    736 Warbler Way Unit 2733, Chester, MD 21619
  • 232 Evelyne St, Chester, MD 21619
    232 Evelyne St, Chester, MD 21619
    232 Evelyne St, Chester, MD 21619
    /35

    $825,000

    $40K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,312 Sq Ft

    232 Evelyne St, Chester, MD 21619

    Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs,

    Courtney Chipouras TTR Sotheby's International Realty

    232 Evelyne St, Chester, MD 21619
  • 102 Boatswain Way Unit 33, Chester, MD 21619
    102 Boatswain Way Unit 33, Chester, MD 21619
    102 Boatswain Way Unit 33, Chester, MD 21619
    /31

    $819,990

    New Construction $43K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 33, Chester, MD 21619

    Private home office with elegant French doors.Chef-worthy gourmet kitchen with sprawling island.Formal dining area with dry bar, perfect for entertaining.Gorgeous great room with cozy electric fireplace.Sophisticated owner's suite with triple windows.Stunning owner's spa bath featuring split vanities.Beautiful balcony has access through primary suite & great room.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 33, Chester, MD 21619
  • 131 Flycatcher Way Unit 36455262, Chester, MD 21619
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
    /16

    $883,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,601 Sq Ft

    Munich ESP Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Extra Suite Plus for multi-generational living.Striking kitchen with large center island and corner pantry.Spacious great room with tons of windows for natural sun light.Luxurious primary suite with oversized walk-in closet.Relaxing primary bath with split vanities and optional freestanding tub.Private home office off foyer for working from home.Large covered patio for

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
Maryland Queen Anne's County

Real Estate & Homes in Chester, MD under $1,000,000

Home Prices in Chester, MD

The median home sale price in Chester, MD is $689,900, up 15% year-over-year. Homes in Chester sell in 429 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$689,900
Median Single Family Sale Price
$749,990
Median Townhouse Sale Price
$369,900
Median 2 Bedroom Sale Price
$634,990
Median 1 Bedroom Sale Price
$338,000
Average Price Per Sq Ft
$310
Number of Homes for Sale
40
Last 12 months Home Sales
213
Months of Supply
4.60
Median List Price
$714,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
15%
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