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Chester, MD Homes for Sale with AC

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  • 3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    /8

    $269,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    3 D Queen Victoria Ct, Chester, MD 21619

    Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet in the bedroom. Queens Landing is a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 888-0022

    3 D Queen Victoria Ct, Chester, MD 21619
  • 4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    /70

    $560,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 390-0346

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /42

    $749,500

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

    1868 Roberta Dr, Chester, MD 21619

    This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning room transitions seamlessly into a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 446-2477

    1868 Roberta Dr, Chester, MD 21619
  • 200 Newtown Rd, Chester, MD 21619
    200 Newtown Rd, Chester, MD 21619
    200 Newtown Rd, Chester, MD 21619
    /34

    $443,000

    • 3 Beds
    • 2.5 Baths
    • 1,296 Sq Ft

    200 Newtown Rd, Chester, MD 21619

    NO HOA! Beautifully maintained 2017-built home offering 3 bedrooms and 2.5 baths. Features a fenced yard for kids and pets, screened porch, large yard with concrete pad, and small storage shed. Temperature-controlled concrete crawl space, new sump pump, and septic contract for easy, worry-free living. Conveniently located near shopping and everything Kent Island has to offer.Make sure you see

    Agent Photo

    Linda Moran

    Berkshire Hathaway HomeServices PenFed Realty-WOC

    (410) 650-8215

    200 Newtown Rd, Chester, MD 21619
  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $814,900

    • 3 Beds
    • 3 Baths
    • 2,795 Sq Ft

    135 Nauset Ln, Chester, MD 21619

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

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset Ln, Chester, MD 21619
  • 1000 Herons Nest Way Unit 42, Chester, MD 21619
    1000 Herons Nest Way Unit 42, Chester, MD 21619
    1000 Herons Nest Way Unit 42, Chester, MD 21619
    /54

    $599,000

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

    1000 Herons Nest Way Unit 42, 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 42, 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 Open Sat 11AM - 1PM

    • 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
  • 501 Teal Ct, Chester, MD 21619
    501 Teal Ct, Chester, MD 21619
    501 Teal Ct, Chester, MD 21619
    /37

    $310,000

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

    501 Teal Ct, Chester, MD 21619

    Welcome to easy, waterfront-inspired living in the heart of Chester! This beautifully maintained first-floor condo at 501 Teal Ct offers the perfect blend of comfort, style, and convenience—plus peaceful views of the community pond right from your backyard. Step inside to find gorgeous hardwood floors flowing throughout the main living space, anchored by a cozy propane fireplace—perfect for those

    Kathleen Higginbotham Samson Properties

    501 Teal 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
  • 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 Open Sat 12:15PM - 1:30PM

    • 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

    $728,000

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

    266 Peregrine Dr, Stevensville, MD 21666

    Huge Price Reduction on this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features 4 bedrooms and 3 full baths is awaiting it's next owner 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
  • 2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    /83

    $750,000

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

    2000 Herons Nest Way Unit 401, Chester, MD 21619

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

    Veronica Lawson Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • 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
  • 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 Open Sat 10AM - 12PM

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

    230 Switchgrass Way Unit 21, Chester, MD 21619

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

    Lawrence Doyle Long & Foster Real Estate, Inc.

    230 Switchgrass Way Unit 21, Chester, MD 21619
  • 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
  • 2613 Cecil Dr, Chester, MD 21619
    2613 Cecil Dr, Chester, MD 21619
    2613 Cecil Dr, Chester, MD 21619
    /52

    $995,000 Open Sat 11AM - 1PM

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

    2613 Cecil Dr, Chester, MD 21619

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

    Peter Stark Benson & Mangold, LLC

    2613 Cecil Dr, Chester, MD 21619
  • 1000 Herons Nest Way Unit 23, Chester, MD 21619
    1000 Herons Nest Way Unit 23, Chester, MD 21619
    1000 Herons Nest Way Unit 23, Chester, MD 21619
    /32

    $494,900

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

    1000 Herons Nest Way Unit 23, Chester, MD 21619

    Welcome to 1000 Herons Nest Way, where you can live the good life at an great price. This immaculate two bedroom condo, with two and a half baths and additional flex space, provides turn key convenience and resort style amenities. This home is a MUST SEE! This FORMER MODEL is like new and includes features that other condos won’t - including decorator upgrades, custom designed closets, plantation

    Nola Meyers EXP Realty, LLC

    1000 Herons Nest Way Unit 23, Chester, MD 21619
  • 312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    /48

    $479,000

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

    312 Blenny Ln, Chester, MD 21619

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

    Judith Brown EXP Realty, LLC

    312 Blenny Ln, Chester, MD 21619
  • 6 G Queen Victoria Way, Chester, MD 21619
    6 G Queen Victoria Way, Chester, MD 21619
    6 G Queen Victoria Way, Chester, MD 21619
    /50

    $294,900

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    6 G Queen Victoria Way, Chester, MD 21619

    Price Improvement!! Marina-front and perfectly sized for easy living or a weekend escape. This one-bedroom one-bath condo offers approximately 724 square feet with an open floor plan and a geourgous view. Walk into a bright living area that flows seemlessly into the adjacent kitchen, creating an inviting and functional space for everyday living or entertaining. The kitchen has been updated with

    Julia Stevens Realty Navigator

    6 G Queen Victoria Way, Chester, MD 21619
  • 402 Blenny Ln, Chester, MD 21619
    402 Blenny Ln, Chester, MD 21619
    402 Blenny Ln, Chester, MD 21619
    /51

    $399,000

    • 3 Beds
    • 3.5 Baths
    • 1,747 Sq Ft

    402 Blenny Ln, Chester, MD 21619

    End-unit three-level townhome overlooking the pond in Bayside community. Freshly painted, new LVP on lower level. Engineered wood floors on main level. Living room has propane fireplace and built-in bookcases/shelves. Most windows have plantation shutters. Sliding door overlooks rear deck, lower level sliding door overlooks rear patio; both with pond views! Amenity-rich Bayside Community offers

    Thomas Welch Long & Foster Real Estate, Inc.

    402 Blenny Ln, Chester, MD 21619
  • 1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    /44

    $479,900

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

    1906 Harbor Dr, Chester, MD 21619

    Experience the epitome of luxury living in this stunning ranch-style home located in the prestigious Harbor View subdivision. This meticulously renovated residence boasts an impressive 1,750 square feet of thoughtfully designed space, perfect for those who appreciate both elegance and functionality. Step inside to discover a harmonious blend of modern sophistication and timeless charm. The

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, 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
    • 2.5 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 turning chilly nights into cozy nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline 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 Open Sat 2PM - 4PM

    • 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
  • 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
  • 1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    /40

    $489,000

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

    1916 Stevens Dr, Chester, MD 21619

    Come see 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
  • 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

    $659,900

    • 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
  • 205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    /29

    $515,000

    • 6 Beds
    • 3 Baths
    • 3,500 Sq Ft

    205 Anchor Ln, Chester, MD 21619

    Price Improvement! Need more room? This expansive home is ready to welcome your whole family! With 6 bedrooms, 3 full bathrooms and an over-sized, 4-car garage, there's plenty of space for everyone to spread out and enjoy their own privacy. You'll be delighted by a mix of formal and casual living spaces, including a bright formal living room, a cozy lower-level family room, and a huge screened

    Darlene Winegardner RE/MAX Executive

    205 Anchor Ln, Chester, MD 21619
  • 1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    /28

    $499,000

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

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Step into the good life in the sought-after Four Seasons on Kent Island, where low-maintenance living meets waterfront vibes. This 2-bedroom, 2-bath home offers spacious one-level living with an open, airy layout, freshly painted interiors, and a stylish kitchen featuring a modern glass subway tile backsplash—perfect for entertaining or unwinding after a day on the Shore. The 1-car garage plus

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • 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
  • 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
  • 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
  • 121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    /40

    $1,099,990 New Construction

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

    121 Kinglet Ct, Chester, MD 21619

    Welcome to the Tuscaloosa, a spacious and thoughtfully designed home offering 5 bedrooms, 4.5 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home delivers the perfect combination of comfort, functionality, and modern design. The main living area features a cozy fireplace with mantel and hearth, creating a warm focal point for gathering. A dedicated home office provides a

    Mary Anne Kowalewski KOVO Realty

    121 Kinglet Ct, Chester, MD 21619
  • 307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    /59

    $979,990 New Construction

    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    307 Kingfisher Ln, Chester, MD 21619

    Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private

    Mary Anne Kowalewski KOVO Realty

    307 Kingfisher Ln, 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 2

Maryland Queen Anne's County Chester

Homes for Sale with AC in Chester, MD

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 202 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, MD over the last 12 months is $649,900, up 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$649,900
Median Single Family Sale Price
$684,900
Median Townhouse Sale Price
$380,000
Median 2 Bedroom Sale Price
$549,900
Median 1 Bedroom Sale Price
$294,500
Average Price Per Sq Ft
$298
Number of Homes for Sale
77
Last 12 months Home Sales
213
Months of Supply
4.30
Median List Price
$672,445
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
12%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 60 homes for sale with air conditioning, providing cool relief during warm summer months. These properties are equipped with modern amenities like central air conditioning systems or individual units, ensuring residents stay comfortable even in hot weather. Whether it's a single-family home or a townhouse, homes for sale with air conditioning offer a pleasant atmosphere year-round. Explore the selection of homes for sale with AC in Chester, MD and enjoy the comfort they provide.

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