92

Chester, MD Homes for Sale

Section Image Section Image
  • 211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    /19

    $739,900

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

    211 Switchgrass Way Unit 31, Chester, MD 21619

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

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

    $619,990

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

    102 Boatswain Way Unit 2911, Chester, MD 21619

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

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2911, Chester, MD 21619
  • 326 Castle Marina Rd, Chester, MD 21619
    326 Castle Marina Rd, Chester, MD 21619
    326 Castle Marina Rd, Chester, MD 21619
    /83

    $550,000

    • 5 Beds
    • 3.5 Baths
    • 3,552 Sq Ft

    326 Castle Marina Rd, Chester, MD 21619

    Discover the charm of this beautiful home in the desirable Castle Marina community. With five spacious bedrooms (including one on the main level) and 3.5 bathrooms, this residence is designed for comfort and functionality. Enjoy cozy evenings by one of the two fireplaces. With new windows, the natural light floods the traditional floor plan, enhanced by recessed lighting and wood floors

    Ginny Dauses Coldwell Banker Waterman Realty

    326 Castle Marina Rd, Chester, MD 21619
  • 228 Bayberry Dr, Chester, MD 21619
    228 Bayberry Dr, Chester, MD 21619
    228 Bayberry Dr, Chester, MD 21619
    /57

    $665,000

    Open Sun 11AM - 1PM
    • 2 Beds
    • 2.5 Baths
    • 1,993 Sq Ft

    228 Bayberry Dr, Chester, MD 21619

    OPEN SATURDAY 9/19 2-4PM. PROFESSIONAL PHOTOS COMING! Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS complete w/private ENSUITE BATHROOMS plus an additional POWDER ROOM & HOME OFFICE. The stunning CHEF'S KITCHEN is the heart of this home & opens up to DINING AREA & GREAT ROOM. KITCHEN features upgraded "CAFE" by GE

    Amy Faust Long & Foster Real Estate, Inc.

    228 Bayberry Dr, 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
  • 54 D Queen Caroline Ct, Chester, MD 21619
    54 D Queen Caroline Ct, Chester, MD 21619
    54 D Queen Caroline Ct, Chester, MD 21619
    /38

    $299,900

    $46K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54 D Queen Caroline Ct, Chester, MD 21619

    Motivated Seller! This home is move in ready. Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring

    Michelle DiDonato Island Realty, LLC

    54 D Queen Caroline Ct, Chester, MD 21619
  • 131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    /13

    $701,990

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

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

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

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

    $1,200,000

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

    117 Flycatcher Way, Chester, MD 21619

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

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

    $924,000

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

    214 Bayberry Dr, Chester, MD 21619

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

    Jim Corson Benson & Mangold, LLC

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

    $374,900

    $84K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 1,899 Sq Ft

    208 Blenny Ln Unit 100, Chester, MD 21619

    NEW AMAZING PRICE!! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully renovated from top to bottom! Step inside to find the main level that boasts NEW carpet and new LVP flooring, a NEW half bath, NEW paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home

    Pamela Ackermann-Doll RE/MAX Executive

    208 Blenny Ln Unit 100, Chester, MD 21619
  • 641 Warbler Way, Chester, MD 21619
    641 Warbler Way, Chester, MD 21619
    641 Warbler Way, Chester, MD 21619
    /24

    $639,990

    New Construction $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    641 Warbler Way, Chester, MD 21619

    Elegant kitchen featuring white cabinetry, center island, & brushed nickel finishes.Expansive great room for spending time with family & friends.Charming dining area with access to covered patio.Peaceful primary suite with stylish ceiling treatment.Polished primary bath featuring dual sinks & barn door.Formal home office provides a quiet space to work remotely.Attached

    K. Hovnanian Homes Builder
    641 Warbler Way, Chester, MD 21619
  • 121 Merlin Dr, Chester, MD 21619
    121 Merlin Dr, Chester, MD 21619
    121 Merlin Dr, Chester, MD 21619
    /84

    $697,900

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

    121 Merlin Dr, Chester, MD 21619

    Assumable VA Loan available w/interest rate in 5's to qualified buyers! Experience the ease of elegant one-level living in this exceptional home, located in one of Maryland's premier 55+ active adult communities on the Chesapeake Bay.Designed for both comfort and style, this beautifully appointed residence features a three-car tandem garage with an EV charger, a spacious screened porch, a

    Yael Beckman Coldwell Banker Realty

    121 Merlin Dr, Chester, MD 21619
  • 102 Boatswain Way Unit 11, Chester, MD 21619
    102 Boatswain Way Unit 11, Chester, MD 21619
    102 Boatswain Way Unit 11, Chester, MD 21619
    /14

    $619,990

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

    102 Boatswain Way Unit 11, Chester, MD 21619

    Open home office just off the main living space.Gourmet kitchen with central island for everyday cooking & gathering.Dining area with dry bar for easy entertaining.Electric fireplace adds warmth to the great room.Patio connects seamlessly to the great room & owner’s suite.Owner’s suite with dual closets for added storage.Owner’s bath with dual sinks & glass shower

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 11, Chester, MD 21619
  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /48

    $400,000

    Open Sat 12PM - 1PM
    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1868 Roberta Dr, Chester, MD 21619

    List price is Opening Bid at the Online auction to be conducted on Auctioneers website.- Auction ends Tuesday, September 29, 2026 at 11:00 AM. Discover the space and versatility of 1868 Roberta Drive in Chester, Maryland, a custom-built home offering 5 bedrooms, 3.5 bathrooms, multiple living areas, abundant storage, and no HOA. Conveniently located just minutes from Route 50 and the

    Carley Cooper Alex Cooper Auctioneers, Inc.

    1868 Roberta Dr, Chester, MD 21619
  • 1340 Queen Anne Dr, Chester, MD 21619
    1340 Queen Anne Dr, Chester, MD 21619
    1340 Queen Anne Dr, Chester, MD 21619
    /27

    $439,900

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1340 Queen Anne Dr, Chester, MD 21619

    PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • 1000 Herons Nest Way Unit 43, Chester, MD 21619
    1000 Herons Nest Way Unit 43, Chester, MD 21619
    1000 Herons Nest Way Unit 43, Chester, MD 21619
    /50

    $595,000

    $5K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    1000 Herons Nest Way Unit 43, Chester, MD 21619

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

    Dee Dee McCracken Coldwell Banker Realty

    1000 Herons Nest Way Unit 43, Chester, MD 21619
  • 114 Kinglet Ct, Chester, MD 21619
    114 Kinglet Ct, Chester, MD 21619
    114 Kinglet Ct, Chester, MD 21619
    /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
  • 315 Bentons Pleasure Rd, Chester, MD 21619
    315 Bentons Pleasure Rd, Chester, MD 21619
    315 Bentons Pleasure Rd, Chester, MD 21619
    /63

    $599,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft

    315 Bentons Pleasure Rd, Chester, MD 21619

    REDUCED!!! This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy and plenty of room to expand. Not many large lots left in this community, check with county for very possible sub dividing for 2 additional lots. Home is in need of updating with lots of potential to add your own touch and design. More pictures coming soon. Currently on septic but sewer is available.

    Douglas Kayhoe Douglas Realty LLC

    315 Bentons Pleasure Rd, Chester, MD 21619
  • 102 Boatswain Way Unit 12, Chester, MD 21619
    102 Boatswain Way Unit 12, Chester, MD 21619
    102 Boatswain Way Unit 12, Chester, MD 21619
    /13

    $599,990

    New Construction $64K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 12, Chester, MD 21619

    Open home office for flexible work or study.Gourmet kitchen with central island at the heart of the home.Dining area with dry bar for easy entertaining.Great room with electric fireplace for a cozy focal point.Patio off the great room with direct access to the owner's suite.Owner's suite with dual closets for added storage.Owner's bath with dual sinks & glass shower

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 12, Chester, MD 21619
  • 1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    /64

    $1,294,800

    New Construction Open Sun 11AM - 1PM
    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

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

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, 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
  • 2004 Bridgepointe Dr, Chester, MD 21619
    2004 Bridgepointe Dr, Chester, MD 21619
    2004 Bridgepointe Dr, Chester, MD 21619
    /32

    $369,900

    Open Sun 10AM - 12PM $13K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    2004 Bridgepointe Dr, Chester, MD 21619

    REDUCED!! Welcome to one of the most desirable Homes in the Bridgepointe Community! ALL NEW Carpet & flooring, fresh custom paint, Granite countertops and Newer Appliances! This beautifully maintained END UNIT home offers added privacy, abundant natural light and a thoughtfully designed floor plan that perfectly blends comfort and convenience. Featuring one of the community's most sought after

    Sheryl Carmody RE/MAX Executive

    2004 Bridgepointe Dr, 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
  • 1717 Harbor Dr, Chester, MD 21619
    1717 Harbor Dr, Chester, MD 21619
    1717 Harbor Dr, Chester, MD 21619
    /77

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,742 Sq Ft

    1717 Harbor Dr, Chester, MD 21619

    Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated approximately four years ago, this move-in-ready home combines modern updates with the timeless appeal of Maryland's Eastern Shore. Offering 3 bedrooms, 2.5 baths, and a highly desirable main-level primary suite, the thoughtfully designed layout provides both comfort and functionality.Inside, you'll

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    1717 Harbor Dr, 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
  • 200 Church St, Chester, MD 21619
    200 Church St, Chester, MD 21619
    200 Church St, Chester, MD 21619
    /28

    $350,000

    Open Sun 12PM - 2PM
    • 2 Beds
    • 2 Baths
    • 1,274 Sq Ft

    200 Church St, Chester, MD 21619

    Your Island Getaway Is Waiting!Dreaming of a cozy home where life feels a little more relaxed and every season brings something to look forward to? This charming 2/3-bedroom Island home may be just what you’ve been waiting for!Start your mornings—or wind down your evenings—on the inviting front porch, where you can swing with the little ones, rock to your favorite playlist, and enjoy the

    Darlene Winegardner RE/MAX Executive

    200 Church St, 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
  • 132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    /29

    $699,000

    $81K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    132 Wheelhouse Way Unit 11, Chester, MD 21619

    Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its replacement value.Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four

    Matthew Arnold Real Broker, LLC

    132 Wheelhouse Way Unit 11, 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
  • 205 Riverside Dr, Chester, MD 21619
    205 Riverside Dr, Chester, MD 21619
    205 Riverside Dr, Chester, MD 21619
    /39

    $699,000

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    205 Riverside Dr, Chester, MD 21619

    Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This

    Melissa Chick Engel & Völkers Annapolis

    205 Riverside Dr, Chester, MD 21619
  • 830 Warbler Way Unit 33, Chester, MD 21619
    830 Warbler Way Unit 33, Chester, MD 21619
    830 Warbler Way Unit 33, Chester, MD 21619
    /27

    $689,990

    New Construction $28K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 33, Chester, MD 21619

    Private home office with elegant French double doors.Gourmet kitchen features a center island & built-in wall oven.Dining area includes a dry bar for added convenience.Great room with an electric fireplace opens to the balcony.Owner's suite offers balcony access for a relaxing retreat.Spa bath provides comfort with dual vanities & modern design.Laundry room includes

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 33, Chester, MD 21619
  • 131 Flycatcher Way Unit 36503530, Chester, MD 21619
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
    /21

    $594,990

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

    Severn Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36503530, Chester, MD 21619

Showing Results 41 - 80, Page 2 of 3

Maryland Queen Anne's County

Real Estate & Homes for Sale in Chester, MD

How to Buy a Home How to Finance a Home How to Sell a Home

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

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group