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Newest Homes for Sale in Chester, MD

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  • 311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    /40

    $969,990 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
  • 176 Flagstaff Way Unit 2424, Chester, MD 21619
    176 Flagstaff Way Unit 2424, Chester, MD 21619
    176 Flagstaff Way Unit 2424, Chester, MD 21619
    /59

    $935,990 New Construction

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

    176 Flagstaff Way Unit 2424, Chester, MD 21619

    The Severn, located on Lot 2424, is scheduled for a August 2026 settlement and offers a well-designed layout with 3 bedrooms, 2.5 baths, and a 1-car garage—perfect for low-maintenance living without sacrificing style. This home features a welcoming electric fireplace, a convenient dry bar for entertaining, and a dedicated storage room to keep everything organized. The kitchen is thoughtfully

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2424, Chester, MD 21619
  • 141 Redstart Dr, Chester, MD 21619
    141 Redstart Dr, Chester, MD 21619
    141 Redstart Dr, Chester, MD 21619
    /25

    $1,049,900 New Construction

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

    141 Redstart Dr, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    141 Redstart Dr, Chester, MD 21619
  • 176 Flagstaff Way Unit 12, Chester, MD 21619
    176 Flagstaff Way Unit 12, Chester, MD 21619
    176 Flagstaff Way Unit 12, Chester, MD 21619
    /9

    $699,990 New Construction

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

    176 Flagstaff Way Unit 12, Chester, MD 21619

    Welcoming foyer leads to open concept living spaces. Efficient gourmet kitchen featuring designer cabinetry & wall oven. Vast center island overlooking dining area with dry bar. Electric fireplace adds warmth & character to great room. Private owner's suite for rest & relaxation. Pristine owner's spa bath featuring framless shower door. Organized home office with lited double doors. Versatile

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 12, Chester, MD 21619
  • 110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    /38

    $989,900 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
  • 176 Flagstaff Way Unit 11, Chester, MD 21619
    176 Flagstaff Way Unit 11, Chester, MD 21619
    176 Flagstaff Way Unit 11, Chester, MD 21619
    /9

    $699,990 New Construction

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

    176 Flagstaff Way Unit 11, Chester, MD 21619

    Gourmet kitchen featuring designer cabinetry & center island. Spacious great room with electric fireplace. Inviting dining area featuring lovely dry bar. Pristine owner's suite & spa bath with walk-in closet. Versatile outdoor patio, perfect for spending time with friends. Productive home office with lited double doors. Functional laundry room for added convenience.

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 11, 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 Open Sun 11AM - 1PM

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    **OPEN HOUSE Sunday, 1/11/26 from 11 - 1PM ** 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

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 390-0346

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    /3

    $499,900

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1906 Harbor Dr, Chester, MD 21619

    Beautifully renovated/remodeled 3 bedroom, 2 full bath home in Chester, MD. Expected date to go active on the market is January 1st, 2026.

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, Chester, MD 21619
  • 206 Blenny Ln, Chester, MD 21619
    206 Blenny Ln, Chester, MD 21619
    206 Blenny Ln, Chester, MD 21619
    /30

    $339,900

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

    206 Blenny Ln, Chester, MD 21619

    Positioned in the heart of Chester’s marina district and just a few blocks from Castle Marina, this 3-bedroom, 2 full/2 half bath townhome brings you close to both nature and convenience. With a 1-car garage, this home is smartly designed across 3 levels with functionality and flow in mind. The main floor opens up to a large living space anchored by a fireplace and bathed in natural light. A

    Chris Craddock EXP Realty, LLC

    206 Blenny Ln, Chester, MD 21619
  • 15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    /18

    $480,000

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    15 Queen Anne Way Unit E, Chester, MD 21619

    Escape to the water — without the waterfront price. This Chester River–front townhome in Queens Landing is the perfect second home or low-maintenance retreat, all for under $500K. Enjoy sunrise water views from your private patio and balcony, and lock-and-leave peace of mind when you head back home. Inside, the layout is easy and functional with luxury vinyl plank flooring, a gas fireplace, and a

    Jennifer Thomas RE/MAX Executive

    15 Queen Anne Way Unit E, Chester, MD 21619
  • 176 Flagstaff Way Unit 2412, Chester, MD 21619
    176 Flagstaff Way Unit 2412, Chester, MD 21619
    176 Flagstaff Way Unit 2412, Chester, MD 21619
    /63

    $699,990 New Construction

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

    176 Flagstaff Way Unit 2412, Chester, MD 21619

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

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2412, Chester, MD 21619
  • 176 Flagstaff Way Unit 2411, Chester, MD 21619
    176 Flagstaff Way Unit 2411, Chester, MD 21619
    176 Flagstaff Way Unit 2411, Chester, MD 21619
    /63

    $699,990 New Construction

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

    176 Flagstaff Way Unit 2411, Chester, MD 21619

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

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2411, Chester, MD 21619
  • 170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    /81

    $699,900 Open Sun 12PM - 2PM

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

    170 Harrier Way Unit 34, Chester, MD 21619

    New year, new price!! This is one of only two 3-bedroom condos on the market in Four Seasons with the immediate availability. Welcome to luxury condo living at Four Seasons at Kent Island, an active 55+ community packed with amenities. This is one of only two 3-bedroom condos on the market in Four Seasons with the immediate availability. No need to wait for a new condo to be built – you can move

    Barry Davis Long & Foster Real Estate, Inc.

    170 Harrier Way Unit 34, Chester, MD 21619
  • 54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    /40

    $349,000

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft

    54H Queen Caroline Ct, Chester, MD 21619

    Nothing to do but move in! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout the living areas and new vinyl flooring in the kitchen. A propane fireplace highlights the great room for cozy chilly nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit it offers lots of

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, Chester, MD 21619
  • 0 Newtown Rd, Chester, MD 21619
    0 Newtown Rd, Chester, MD 21619
    0 Newtown Rd, Chester, MD 21619
    /7

    $230,000

    • Land
    • 1.68 Acres
    • $136,905 per Acre

    0 Newtown Rd, Chester, MD 21619

    Looking for peace and serenity, look no further! You won't find a better opportunity on the eastern shore, total of 1.68 acres (per the tax record)! This acreage is a total of 2 tax ID numbers being sold as a package. Buyer to verify perc, well, engineering, specific lot lines and land survey. Seller will not.

    Rob Carter Douglas Realty, LLC

    0 Newtown Rd, Chester, MD 21619
  • 10 B Queen Elizabeth Ct, Chester, MD 21619
    10 B Queen Elizabeth Ct, Chester, MD 21619
    10 B Queen Elizabeth Ct, Chester, MD 21619
    /19

    $330,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    10 B Queen Elizabeth Ct, Chester, MD 21619

    WATERFRONT !!! Spectacular sunrise views on display over the Chester River from this cozy 1 bedroom, 1 bath condo in the popular community of Queens Landing. Known for its amenities, you are sure to enjoy living here whether as a full-time resident or just to have as a week-end getaway! Minutes from the Bay Bridge, you can be here without ever getting on route 50!Amenities are as follows:

    Mary Stevens Long & Foster Real Estate, Inc.

    10 B Queen Elizabeth Ct, Chester, MD 21619
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /47

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    807 Auckland Way, Chester, MD 21619

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

    David Moore Real Broker, LLC

    807 Auckland Way, Chester, MD 21619
  • 109 John Gibson Dr, Chester, MD 21619
    109 John Gibson Dr, Chester, MD 21619
    109 John Gibson Dr, Chester, MD 21619
    /78

    $915,000

    • 6 Beds
    • 4.5 Baths
    • 4,165 Sq Ft

    109 John Gibson Dr, Chester, MD 21619

    Start the New Year as a resident of Gibson’s Grant!Discover over 4,100 sq. ft. of high-end, custom elegance in this exceptional Eastern Shore home—perfectly located in one of Chester’s most sought-after waterfront communities. With 6 bedrooms, 4.5 baths, and designer touches at every turn, this residence offers the space, craftsmanship, and lifestyle today’s buyers crave.Step inside the

    Lisa Barton Coldwell Banker Realty

    109 John Gibson Dr, 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
  • 630 Warbler Way Unit 33, Chester, MD 21619
    630 Warbler Way Unit 33, Chester, MD 21619
    630 Warbler Way Unit 33, Chester, MD 21619
    /30

    $644,990 New Construction

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

    630 Warbler Way Unit 33, Chester, MD 21619

    Charming gourmet kitchen featuring designer cabinetry & wall oven. Open concept living spaces with electric fireplace & dry bar. Private owner's suite for rest & relaxation. Refreshing primary bath featuring split vanities. Functional home office featuring double doors for added privacy. Lovely balcony for spending time with friends.

    K. Hovnanian Homes Builder
    630 Warbler Way Unit 33, Chester, MD 21619
  • 630 Warbler Way Unit 32, Chester, MD 21619
    630 Warbler Way Unit 32, Chester, MD 21619
    630 Warbler Way Unit 32, Chester, MD 21619
    /30

    $644,990 New Construction

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

    630 Warbler Way Unit 32, Chester, MD 21619

    Efficient gourmet kitchen featuring designer cabinetry & center island. Spacious great room with electric fireplace. Charming dining area featuring dry bar. Lavish owner's suite & spa bath with walk-in closet. Productive home office featuring double doors. Versatile balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    630 Warbler Way Unit 32, 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
    /49

    $1,400,000 New Construction

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

    117 Flycatcher Way, Chester, MD 21619

    The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio

    Mary Anne Kowalewski KOVO Realty

    117 Flycatcher Way, Chester, MD 21619
  • 1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    /40

    $495,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft

    1916 Stevens Dr, Chester, MD 21619

    Discover this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a scenic 0.35-acre corner lot in the highly desirable Harbor View community, just two miles east of the Chesapeake Bay Bridge. Inside, enjoy a bright, modern kitchen with new countertops and backsplash, hardwood floors on the main and upstairs evels, and cathedral ceiling with skylights. Relax in the spacious

    Kimberly O'Connor Coldwell Banker Realty

    1916 Stevens Dr, Chester, MD 21619
  • 2907 Cox Neck Rd E, Chester, MD 21619
    2907 Cox Neck Rd E, Chester, MD 21619
    2907 Cox Neck Rd E, Chester, MD 21619
    /43

    $1,899,000

    • 4 Beds
    • 6 Baths
    • 3,460 Sq Ft

    2907 Cox Neck Rd E, Chester, MD 21619

    Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside

    Brad Kappel TTR Sotheby's International Realty

    2907 Cox Neck Rd E, Chester, MD 21619
  • 112 Chessie Ct, Chester, MD 21619
    112 Chessie Ct, Chester, MD 21619
    112 Chessie Ct, Chester, MD 21619
    /37

    $519,900

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    112 Chessie Ct, Chester, MD 21619

    Step inside and see this meticulously cared for home!This home features a first floor primary bedroom with an ensuite full bath.Just 5 minutes from the Chesapeake Bay Bridge and all the beaches, parks, boat ramps, and waterfront venues you love to visit...all within a few minutes drive.This single detached home has been thoughtfully improved throughout, with luxury vinyl plank floors,

    Carol Delayo Chaney Homes, LLC

    112 Chessie Ct, Chester, MD 21619
  • 306 Teal Ct, Chester, MD 21619
    306 Teal Ct, Chester, MD 21619
    306 Teal Ct, Chester, MD 21619
    /24

    $295,000

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    306 Teal Ct, Chester, MD 21619

    Beautifully maintained first-floor condominium offering serene lake views and an open, inviting floor plan.This residence features two spacious bedrooms and two full bathrooms. The light-filled living and dining areas provide direct access to a private patio overlooking the lake, perfect for enjoying peaceful mornings.Located in a highly desirable community of Bayside, offering

    Cindy Jacobs Maryland Residential Management Co

    306 Teal Ct, Chester, MD 21619
  • 203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    /68

    $1,099,900 New Construction

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

    203 Riverside Dr, Chester, MD 21619

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

    Chrissy Schultz Long & Foster Real Estate, Inc.

    203 Riverside Dr, Chester, MD 21619
  • 202 Mchenny Ct, Chester, MD 21619
    202 Mchenny Ct, Chester, MD 21619
    202 Mchenny Ct, Chester, MD 21619
    /63

    $825,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    202 Mchenny Ct, Chester, MD 21619

    Beautiful Home in Gibson’s Grant with Elevator, Open Floor Plan & Two-Car GarageWelcome to this beautifully appointed home in the sought-after waterfront community of Gibson’s Grant on Kent Island. This residence offers a perfect blend of comfort, style, and convenience — featuring a spacious open floor plan and an attached two-car garage.No need to worry about stairs — a full elevator

    Dee Dee McCracken Coldwell Banker Realty

    202 Mchenny Ct, Chester, MD 21619
  • 0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    /12

    $499,900 New Construction

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

    0 Harbor Dr, Chester, MD 21619

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

    DJ Dauses Coldwell Banker Waterman Realty

    0 Harbor Dr, Chester, MD 21619
  • 630 Warbler Way Unit 2232, Chester, MD 21619
    630 Warbler Way Unit 2232, Chester, MD 21619
    630 Warbler Way Unit 2232, Chester, MD 21619
    /48

    $644,990 New Construction

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

    630 Warbler Way Unit 2232, Chester, MD 21619

    The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2232, Chester, MD 21619
  • 3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    /66

    $555,900

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

    3000 Herons Nest Way Unit 11, Chester, MD 21619

    Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. This highly sought-after first-floor condo is move-in ready and has been meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced by crown

    John Freeman Coldwell Banker Realty

    3000 Herons Nest Way Unit 11, Chester, MD 21619
  • 1870 Harbor Dr, Chester, MD 21619
    1870 Harbor Dr, Chester, MD 21619
    1870 Harbor Dr, Chester, MD 21619
    /34

    $320,000

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    1870 Harbor Dr, Chester, MD 21619

    Discover this charming 2-bedroom, 1-bath home in Harbor View featuring beautiful wood floors, a brand-new roof, updated windows, and a spacious rear deck overlooking a large fenced backyard—perfect for relaxing or entertaining while enjoying the Island lifestyle. Ideally located near restaurants, shopping, and easy access to Route 50 for commuting. Come See!

    Rick Parreco RE/MAX Executive

    1870 Harbor Dr, Chester, MD 21619
  • 132 Wheelhouse Way, Chester, MD 21619
    132 Wheelhouse Way, Chester, MD 21619
    132 Wheelhouse Way, Chester, MD 21619
    /68

    $1,299,990 New Construction

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

    132 Wheelhouse Way, Chester, MD 21619

    This beautifully designed Chester Model Home offers sophisticated comfort and modern convenience, ready for immediate move-in with a flexible month-to-month leaseback opportunity. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home blends style and function seamlessly. Thoughtful touches include a fully furnished interior, a dry bar perfect for entertaining, and an electric fireplace

    Mary Anne Kowalewski KOVO Realty

    132 Wheelhouse Way, Chester, MD 21619
  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $814,900

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

    135 Nauset Ln, Chester, MD 21619

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

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset Ln, Chester, MD 21619
  • 201 Golden Eye Ct, Chester, MD 21619
    201 Golden Eye Ct, Chester, MD 21619
    201 Golden Eye Ct, Chester, MD 21619
    /50

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    201 Golden Eye Ct, Chester, MD 21619

    Welcome to this bright and inviting 2-bedroom, 2-bathroom lower-level end unit condo, ideally located in a desirable water-oriented community on Kent Island! The open living and dining area flows seamlessly into a galley-style kitchen with a breakfast bar, now updated with new granite countertops and a new stainless steel stove. The Primary suite is your private retreat, complete with a walk-in

    Melissa Tippett TTR Sotheby's International Realty

    201 Golden Eye Ct, Chester, MD 21619
  • 1839 Harbor Dr, Chester, MD 21619
    1839 Harbor Dr, Chester, MD 21619
    1839 Harbor Dr, Chester, MD 21619
    /23

    $350,999

    • 4 Beds
    • 2 Baths
    • 2,035 Sq Ft

    1839 Harbor Dr, Chester, MD 21619

    MAJOR REDUCTION! Opportunity KnocksWelcome to Harbor View on Kent Island - Just 7 minutes from the Bay BridgeThis oversized ranch style home boasts 4 Bedrooms and 2 Full baths and is located just one block from Cox Creek. The open concept floor plan features a formal living room, large main level bedroom, hardwood flooring throughout, a modern kitchen with ample cabinetry, center island,

    Greg Koch Taylor Properties

    1839 Harbor Dr, Chester, MD 21619
  • 312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    /40

    $305,000

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    312 Teal Ct Unit F, Chester, MD 21619

    This is a highly sought-after location on Kent Island, known for its limited availability.Sellers have updated shiplap in the living room, paint throughout the house. This second-floor condo offers breathtaking views of the pond. You will enjoy an updated backsplash in the kitchen, featuring granite countertops and stainless steel appliances. Hardwood flooring is throughout the house. The

    Mary Rice Engel & Völkers Ocean City

    312 Teal Ct Unit F, Chester, MD 21619
  • 200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    /44

    $674,900

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

    200 Harrier Way Unit 21, Chester, MD 21619

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

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, Chester, MD 21619
  • 1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    /32

    $454,900 Open Sat 10AM - 12PM

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

    1401 Calvert Rd, Chester, MD 21619

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

    Suzanne Hitt Coldwell Banker Waterman Realty

    1401 Calvert Rd, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Annes County Chester

Newest Listings for Sale in Chester, MD

Frequently Asked Questions

What is the average home price in Chester, MD?
Homes for sale in Chester, MD have an average home price of $628,336.
How many homes have sold over the last 12 months in Chester, MD?
191 homes have sold in Chester, MD over the last 12 months.
Is Chester, MD a safe city?
In general, the safest neighborhood in Chester, MD with lower crime scores is Kent Narrows.
What are the most popular zip codes in Chester, MD?
The most popular zip codes in Chester, MD include 21619, 21666, 21638, 21658 and 21409.
What are the most popular neighborhoods in Chester, MD?
The most popular neighborhood in Chester, MD with the most homes for sale is Kent Narrows.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $639,900. If you put a 20% down payment of $128,000 and had a 30-year fixed mortgage with an interest rate of 6.15%, your estimated principal and interest payment would be $3,120 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $134K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, MD?
Chester, MD has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Bayside Elementary School, Matapeake Middle School and Kent Island Elementary School. The neighborhood in Chester with the highest rated schools is Kent Narrows. Browse all the schools in Chester, MD to learn more.

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 100 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, MD over the last 12 months is $624,900, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$624,900
Median Single Family Sale Price
$644,900
Median Townhouse Sale Price
$365,000
Median 2 Bedroom Sale Price
$543,450
Median 1 Bedroom Sale Price
$320,000
Average Price Per Sq Ft
$292
Number of Homes for Sale
57
Last 12 months Home Sales
191
Months of Supply
3.60
Median List Price
$639,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
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