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Newest Homes for Sale in Chester, MD

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  • 1604 Midway Rd, Chester, MD 21619
    1604 Midway Rd, Chester, MD 21619
    1604 Midway Rd, Chester, MD 21619
    /12

    $795,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3 Baths
    • 2,972 Sq Ft

    1604 Midway Rd, Chester, MD 21619

    Discover the perfect blend of tranquility and recreation in Marling Farms, where this stunning 1.01-acre lot awaits your vision. Imagine a lspacious yard that invites outdoor gatherings and serene moments under the stars, complemented by a personal gunite pool, perfect for summer relaxation. Just shy of 3000 square feet of liviing space gives everyone plenty of room to spread out complete with

    Tricia Wilson Wilson Realty & Staging LLC

    1604 Midway Rd, Chester, MD 21619
  • 215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    /44

    $1,100,000 Open Sat 9AM - 12PM

    • 5 Beds
    • 4.5 Baths
    • 3,914 Sq Ft

    215 Kingfisher Ln, Stevensville, MD 21666

    Why wait to build? This less-than-one-year-old Tusculusa model on sought-after Kingfisher Lane checks every box. Located just across from the Chester River, you’ll catch peekaboo water views from the covered front porch—and you can even see the clubhouse from the house.Inside, the layout is open, bright, and easy to live in, with **5 bedrooms and 4.5 baths** and plenty of space for guests,

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, Stevensville, MD 21666
  • 132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    /55

    $799,900

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

    132 Wheelhouse Way Unit 11, Chester, MD 21619

    Experience refined coastal living at 132 Wheelhouse Way #11, where the highly desirable Magothy floor plan offers sweeping water views and an unparalleled setting just steps from the clubhouse and Eastern Shore-inspired amenities. Perfectly positioned in one of the community’s most sought-after buildings, this residence has been meticulously maintained and reflects true pride of ownership

    Veronica Lawson Real Broker, LLC

    132 Wheelhouse Way Unit 11, Chester, MD 21619
  • 111 Marshgrass Way Unit 43, Chester, MD 21619
    111 Marshgrass Way Unit 43, Chester, MD 21619
    111 Marshgrass Way Unit 43, Chester, MD 21619
    /61

    $765,000

    • 2 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 43, Chester, MD 21619

    Rare penthouse unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the living room, dining area, and kitchen areas, all enhanced

    John Freeman Coldwell Banker Realty

    111 Marshgrass Way Unit 43, Chester, MD 21619
  • 1000 Herons Nest Way Unit 22, Chester, MD 21619
    1000 Herons Nest Way Unit 22, Chester, MD 21619
    1000 Herons Nest Way Unit 22, Chester, MD 21619
    /56

    $488,000

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

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE.This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, Chester, MD 21619
  • 23F Queen Victoria Way, Chester, MD 21619
    23F Queen Victoria Way, Chester, MD 21619
    23F Queen Victoria Way, Chester, MD 21619
    /36

    $445,000 Open Sun 10AM - 12PM

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft

    23F Queen Victoria Way, Chester, MD 21619

    Offered for the first time in over 30 years, this lovingly maintained 2-bedroom, 2-bath residence is filled with warmth, history, and memories that have been cherished by the same family for decades. Perfectly positioned in sought-after Queen’s Landing, the home captures truly exceptional, direct views of the marina basin, marina fairway, and the Chester River—an ever-changing waterfront backdrop

    Jennifer Thomas RE/MAX Executive

    23F Queen Victoria Way, Chester, MD 21619
  • 1000 Herons Nest Way Unit 402, Chester, MD 21619
    1000 Herons Nest Way Unit 402, Chester, MD 21619
    1000 Herons Nest Way Unit 402, Chester, MD 21619
    /54

    $599,000

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

    1000 Herons Nest Way Unit 402, Chester, MD 21619

    Rarely on the market Penthouse level Chester model available immediately! Balcony views from the top floor leftside provide view of the Chester River, Macum Creek and the Community Kayak's. Located within the serene and vibrant community of Four Seasons at Kent Island, this exquisite 2-bedroom, 2.5 bath Built in 2020, this elegant unit combines modern design with high-end finishes, creating a

    Dan Judge RE/MAX United Real Estate

    1000 Herons Nest Way Unit 402, Chester, MD 21619
  • 34 Queen Anne Way Unit F, Chester, MD 21619
    34 Queen Anne Way Unit F, Chester, MD 21619
    34 Queen Anne Way Unit F, Chester, MD 21619
    /21

    $349,900

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    34 Queen Anne Way Unit F, Chester, MD 21619

    Rare Opportunity in Queen’s Landing with Stunning Chester River Views Welcome to one of the few oversized one-bedroom condos in the highly desirable Queen’s Landing community. Immaculately maintained and thoughtfully designed, this larger-than-average unit offers gorgeous views of the Chester River and the added benefit of expanded living space rarely found in one-bedroom layouts. The larger

    Joelle Dolch Cross Street Realtors LLC

    34 Queen Anne Way Unit F, 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
    /11

    $663,917 New Construction

    • 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 enclosure. Bedroom 2 with

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 11, Chester, MD 21619
  • 102 Boatswain Way Unit 21, Chester, MD 21619
    102 Boatswain Way Unit 21, Chester, MD 21619
    102 Boatswain Way Unit 21, Chester, MD 21619
    /19

    $901,540 New Construction

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

    102 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island & sleek finishes. Dining area with built-in dry bar for easy entertaining. Bright great room with electric fireplace & open layout. Private balcony just off the great room. Owner’s suite with dual walk-in closets for added storage. Sitting room in owner’s suite with direct balcony access. Spa-inspired owner’s bath with dual sinks & glass-enclosed

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 21, 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
    /11

    $663,917 New Construction

    • 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 enclosure. Bedroom 2

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 12, 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
    /19

    $1,003,673 New Construction

    • 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
  • 507 Teal Ct, Chester, MD 21619
    507 Teal Ct, Chester, MD 21619
    507 Teal Ct, Chester, MD 21619
    /5

    $5,000

    • 2 Beds
    • 2 Baths
    • 1,071 Sq Ft

    507 Teal Ct, Chester, MD 21619

    Foreclosure Auction Ends April 14, 2026 at 10:05 AM EST. Discover this inviting 2-bedroom, 2-bathroom single-family home, offering a great opportunity in a welcoming Chester community. The list price is the opening bid for the online auction. Sold As-is. Explore more details and submit your bid through Federa Home App.

    Jamie Boone Jamie L Boone LLC

    507 Teal Ct, Chester, MD 21619
  • 0 Lot #1 Harley Ln, Chester, MD 21619
    0 Lot #1 Harley Ln, Chester, MD 21619
    0 Lot #1 Harley Ln, Chester, MD 21619
    /6

    $159,900

    • Land
    • 0.29 Acre
    • $551,379 per Acre

    0 Lot #1 Harley Ln, Chester, MD 21619

    2 Great Building Lots - Sewer Approved on Kent Island , Sewer fee is paid for - Harley Lane Lot #1 Parcel 63 comes with working Well $159,900. An Adjacent Lot #2 Parcel 64 is available. Sewer is also approved with fee paid. $149,900. These approved Lots are registered with Queen Annes County. *****The Harley Lane 2 lot sub division was created by adding 2 lots on land owned on Good hand creek

    Thomas Hennerty NetRealtyNow.com, LLC

    0 Lot #1 Harley Ln, Chester, MD 21619
  • 102 Merganser Ct, Chester, MD 21619
    102 Merganser Ct, Chester, MD 21619
    102 Merganser Ct, Chester, MD 21619
    /15

    $300,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    102 Merganser Ct, Chester, MD 21619

    Come see this spacious, coastal inspired condo at Bayside on Kent Island. This 2 BR/2 Bath home offers all the benefits of first floor,one level living. A welcoming entrance whispers, " stay awhile" with a sunny patio area overlooking a lush lawn and water views. Inside you will notice plenty of windows, light, and an open-concept design that creates the perfect mood for that "laid back" Kent

    Carol Delayo Chaney Homes, LLC

    102 Merganser Ct, Chester, MD 21619
  • 169 Harrier Way, Chester, MD 21619
    169 Harrier Way, Chester, MD 21619
    169 Harrier Way, Chester, MD 21619
    /85

    $779,900

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

    169 Harrier Way, Chester, MD 21619

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

    Dorothea Slaughter Century 21 Redwood Realty

    169 Harrier Way, Chester, MD 21619
  • 249 Warbler Way, Chester, MD 21619
    249 Warbler Way, Chester, MD 21619
    249 Warbler Way, Chester, MD 21619
    /68

    $699,000

    • 2 Beds
    • 2 Baths
    • 2,025 Sq Ft

    249 Warbler Way, Chester, MD 21619

    **OPEN HOUSE SATURDAY 3/28/26! 10am to 12pm** No waiting on the Builder here! This almost brand new Jenkins II Model was built just last year and boasts soaring, coffered and vaulted ceilings in the 2,025 sf of spaciousness! The generously sized primary suite & spa like bath with a huge walk-in-closet, double vanities & walk-in-shower is sure to make you feel like Royalty! The 2nd bedroom & full

    Pamela Ackermann-Doll RE/MAX Executive

    249 Warbler Way, Chester, MD 21619
  • 102 Warbler Way Unit 2912, Chester, MD 21619
    102 Warbler Way Unit 2912, Chester, MD 21619
    102 Warbler Way Unit 2912, Chester, MD 21619
    /63

    $649,990 New Construction

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

    102 Warbler Way Unit 2912, Chester, MD 21619

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

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2912, Chester, MD 21619
  • 102 Warbler Way Unit 2934, Chester, MD 21619
    102 Warbler Way Unit 2934, Chester, MD 21619
    102 Warbler Way Unit 2934, Chester, MD 21619
    /44

    $989,990 New Construction

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

    102 Warbler Way Unit 2934, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2934, Chester, MD 21619
  • 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 Warbler Way Unit 2921, Chester, MD 21619
    102 Warbler Way Unit 2921, Chester, MD 21619
    102 Warbler Way Unit 2921, Chester, MD 21619
    /44

    $889,990 New Construction

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

    102 Warbler Way Unit 2921, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2921, Chester, MD 21619
  • 102 Warbler Way Unit 2911, Chester, MD 21619
    102 Warbler Way Unit 2911, Chester, MD 21619
    102 Warbler Way Unit 2911, Chester, MD 21619
    /63

    $649,990 New Construction

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

    102 Warbler Way Unit 2911, Chester, MD 21619

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

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2911, Chester, MD 21619
  • 1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    /23

    $485,000

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

    1872 Harbor Dr, Chester, MD 21619

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

    Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • 34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    /52

    $549,000

    • 2 Beds
    • 2.5 Baths
    • 1,586 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    Open House Saturday April 4th 12:15- 1:30. Fully Remodeled Chester River Waterfront Condo! This gem won't last long! Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl plank

    Lona Todd Taylor Properties

    34 Queen Anne Way, Chester, MD 21619
  • 266 Peregrine Dr, Stevensville, MD 21666
    266 Peregrine Dr, Stevensville, MD 21666
    266 Peregrine Dr, Stevensville, MD 21666
    /73

    $720,000

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

    266 Peregrine Dr, Stevensville, MD 21666

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

    Edward Beres RE/MAX Executive

    266 Peregrine Dr, Stevensville, MD 21666
  • 1838 Sherman Dr, Chester, MD 21619
    1838 Sherman Dr, Chester, MD 21619
    1838 Sherman Dr, Chester, MD 21619
    /29

    $387,500

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    1838 Sherman Dr, Chester, MD 21619

    Nestled in the heart of Chester, Maryland on the beautiful Eastern Shore, this charming rancher offers comfort and convenience. Inside, a bright and inviting interior features neutral tones, modern finishes, and a functional layout ideal for everyday living. The light-filled dining area overlooks the backyard and flows into the galley kitchen, complete with stainless steel appliances, ample

    Bret Merson Keller Williams Realty Centre

    1838 Sherman Dr, Chester, MD 21619
  • 719 Warbler Way, Chester, MD 21619
    719 Warbler Way, Chester, MD 21619
    719 Warbler Way, Chester, MD 21619
    /15

    $889,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,807 Sq Ft

    719 Warbler Way, Chester, MD 21619

    Polished kitchen with white cabinets & glass-front uppers. Vast island & quartz countertops for prep & dining. Welcoming great room featuring elegant fireplace. Screened patio with direct access to the great room. Charming dining area for mealtime enjoyment. Lavish primary suite & bath with dual vanities & feature wall. Private home office for leisure activities.

    K. Hovnanian Homes Builder
    719 Warbler Way, Chester, MD 21619
  • 110 Boatswain Way Unit 41, Chester, MD 21619
    110 Boatswain Way Unit 41, Chester, MD 21619
    110 Boatswain Way Unit 41, Chester, MD 21619
    /18

    $949,990 New Construction

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

    110 Boatswain Way Unit 41, Chester, MD 21619

    Welcoming foyer leads into open-concept living spaces. Gourmet kitchen featuring ample cabinetry & seamless connection to the dining area. Dry bar adds a stylish touch, ideal for hosting guests. Spacious great room highlighted by a cozy fireplace. Owner’s suite features a private sitting room & walk-in closet. Owner’s bath showcases a frameless shower door for a modern, elevated feel. Balcony

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 41, Chester, MD 21619
  • 110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    /28

    $799,990 New Construction

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

    110 Boatswain Way Unit 42, Chester, MD 21619

    Gourmet kitchen with designer cabinetry & vast center island. Inviting great room featuring a cozy electric fireplace. Dry bar creates a polished space for serving & entertaining. Peaceful owner's suite with stylish tray ceiling & private bath. Home office with double doors offers a quiet, flexible workspace. Balcony extends the living space outdoors for relaxing or unwinding.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 42, Chester, MD 21619
  • 110 Boatswain Way Unit 32, Chester, MD 21619
    110 Boatswain Way Unit 32, Chester, MD 21619
    110 Boatswain Way Unit 32, Chester, MD 21619
    /29

    $699,990 New Construction

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

    110 Boatswain Way Unit 32, Chester, MD 21619

    Gourmet kitchen with central island for prep & dining. Home office with double doors adds privacy & style. Dining area enhanced by a convenient dry bar. Great room centered around an electric fireplace. Balcony extends living space off the great room. Owner’s suite with private balcony access for relaxation. Spa-like owner’s bath with dual sinks & sleek finishes.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 32, Chester, MD 21619
  • 110 Boatswain Way Unit 31, Chester, MD 21619
    110 Boatswain Way Unit 31, Chester, MD 21619
    110 Boatswain Way Unit 31, Chester, MD 21619
    /21

    $849,990 New Construction

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

    110 Boatswain Way Unit 31, Chester, MD 21619

    Home office with double doors for privacy. Great room with an electric fireplace for warmth & charm. Large central island anchors the gourmet kitchen. Dry bar in dining area creates a perfect hosting space. Owner’s suite with a serene sitting room & balcony access. Dual walk-in closets for organized living. Owner’s bath with sleek dual sinks & spacious layout.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 31, Chester, MD 21619
  • 110 Boatswain Way Unit 44, Chester, MD 21619
    110 Boatswain Way Unit 44, Chester, MD 21619
    110 Boatswain Way Unit 44, Chester, MD 21619
    /20

    $989,990 New Construction

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

    110 Boatswain Way Unit 44, Chester, MD 21619

    Open-concept kitchen, dining area, & great room designed for effortless flow. Gourmet kitchen with ample cabinetry for streamlined storage & prep. Dry bar creates a dedicated space for serving & display. Fireplace adds warmth & character to the great room. Owner’s suite with sitting room, walk-in closet & private bath. Frameless shower door delivers a sleek, spa-like touch in the owner’s bath.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 44, 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
    /82

    $750,000 Open Sat 11AM - 1PM

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

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    This rare, luxurious Severn penthouse in Four Seasons at Kent Island is available immediately and offers a lifestyle that blends comfort, elegance, and natural beauty. Built in 2020 and beautifully maintained, the residence features an open floor plan with abundant windows that fill the home with natural light, creating a warm, inviting atmosphere. At the heart of the home is a stunning kitchen

    Veronica Lawson Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • 132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    /45

    $995,000

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

    132 Kestrel Ln, Chester, MD 21619

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

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, Chester, MD 21619
  • 121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    /42

    $1,099,990 New Construction

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

    121 Kinglet Ct, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    121 Kinglet Ct, Chester, MD 21619
  • 307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    /35

    $979,990 New Construction

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

    307 Kingfisher Ln, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    307 Kingfisher Ln, Chester, MD 21619
  • 8F Queen Victoria Way, Chester, MD 21619
    8F Queen Victoria Way, Chester, MD 21619
    8F Queen Victoria Way, Chester, MD 21619
    /30

    $249,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    8F Queen Victoria Way, Chester, MD 21619

    Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertaining. Private patio off bedroom with secured storage. Laundry is stackable located in bedroom. You will enjoy the Queen's Landing community clubhouse, marina, tennis court and pool and well as the trails in the community.Call today for your private showing.

    Linda Austin Long & Foster Real Estate, Inc.

    8F Queen Victoria Way, Chester, MD 21619
  • 230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    /67

    $694,500

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

    230 Switchgrass Way Unit 21, Chester, MD 21619

    --------------------------------------EXCEPTIONAL PANORAMIC VIEWS ------------------------------------- This unit is Immediate Move In Ready. Builders new units will not be ready until late 2026. Nature, water and sunshine abound in this beautifully situated, stunning 3BR corner unit at Four Seasons. Flexible closing available. South, west and north exposures through 17 windows and two sets of

    Lawrence Doyle Long & Foster Real Estate, Inc.

    230 Switchgrass Way Unit 21, Chester, MD 21619
  • 111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, Chester, MD 21619
    /102

    $539,000

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

    111 Marshgrass Way Unit 22, Chester, MD 21619

    Rare resale condo, turnkey! Your dream retreat awaits in this stunning luxury condo, where modern elegance meets breathtaking natural beauty. This exquisite residence features two spacious bedrooms, each with its own en-suite bath, and an additional half bath for guests. The thoughtfully designed office boasts custom built-in cabinets, providing both functionality and style.--Step into the heart

    Dee Dee Miller Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 22, Chester, MD 21619
  • 110 Boatswain Way Unit 3041, Chester, MD 21619
    110 Boatswain Way Unit 3041, Chester, MD 21619
    110 Boatswain Way Unit 3041, Chester, MD 21619
    /44

    $949,990 New Construction

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

    110 Boatswain Way Unit 3041, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in November 2026, this home combines modern style with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. The owner’s suite includes a sitting room and large walk-in closets, providing a

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3041, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 3

Maryland Queen Anne's 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 $672,800.
How many homes have sold over the last 12 months in Chester, MD?
212 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 $679,000. If you put a 20% down payment of $135,800 and had a 30-year fixed mortgage with an interest rate of 6.37%, your estimated principal and interest payment would be $3,390 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $145K 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 200 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, MD over the last 12 months is $644,990, up 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$644,990
Median Single Family Sale Price
$685,356
Median Townhouse Sale Price
$364,000
Median 2 Bedroom Sale Price
$558,500
Median 1 Bedroom Sale Price
$294,500
Average Price Per Sq Ft
$299
Number of Homes for Sale
69
Last 12 months Home Sales
212
Months of Supply
3.90
Median List Price
$679,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
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