82

Homes for Sale in 21619

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  • /32

    $540,000

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

    190 Harrier Way Unit 11, Chester, MD 21619

    Luxury 55+ Living at Four Seasons on Kent Island – Move-In Ready & Priced to Sell!Welcome to the resort-style lifestyle of Four Seasons on Kent Island, an amenity-rich 55+ waterfront community where luxury, comfort, and convenience meet. Inside, you'll find open-concept layouts filled with natural light, gourmet kitchens with quartz countertops, GE Profile stainless steel

    Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
  • /30

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft

    413 Dominion Rd, Chester, MD 21619

    KENT ISLAND *Single Family Home * 3 bedrooms, 2 full bathrooms * Main level has a spacious eat in kitchen with french doors leading to the backyard deck, family room with lots of natural light and brand new full bathroom with newer LG front loading washer and dryer * There are 3 bedrooms and a full bathroom with tub/shower upstairs *Heat pump system with central AC* Many upgrades through out the

    Suzanne Hitt Coldwell Banker Waterman Realty

    413 Dominion Rd, Chester, MD 21619
  • /22

    $393,000

    • 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 single-story rancher offers the perfect blend of comfort, charm, and convenience. Set on a spacious, fully fenced lot, this home provides a serene retreat with plenty of outdoor space to relax or entertain.Step inside to find a bright and inviting interior with tasteful neutral tones, modern finishes, and a

    Kara Shaffer Engel & Völkers Annapolis

    1838 Sherman Dr, Chester, MD 21619
  • /47

    $566,000 Open Sat 12:30PM - 1:30PM

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

    205 Anchor Ln, Chester, MD 21619

    OPEN HOUSE, Saturday, 12:30 - 1:30 pm...Price Improvement! Need more room? This expansive home is ready to welcome your whole family! With 5 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

    Darlene Winegardner RE/MAX Executive

    205 Anchor Ln, Chester, MD 21619
  • /68

    $539,000 Open Sat 11:30AM - 1PM

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

    15 Queen Anne Way Unit E, Chester, MD 21619

    Price Improvement and a full year of Condo Fees paid!! Wake up to shimmering Chester River views and let every day feel like a getaway!This beautifully maintained 2.5-level townhome offers 1,680 square feet of stylish and functional living space in the sought-after waterfront community of Queens Landing. The main level features a cozy living area with a gas fireplace, luxury vinyl plank

    Julia Stevens Realty Navigator

    15 Queen Anne Way Unit E, Chester, MD 21619
  • /40

    $539,500

    • 3 Beds
    • 3.5 Baths
    • 2,131 Sq Ft

    112 Harbour Sound Dr, Chester, MD 21619

    Resort Living at it's best!! Available furnished or unfurnished. Enjoy stunning, unobstructed water views in the highly sought after community of Bayside! Many recent upgrades and improvements to this home include renovated bathrooms (2024) , New garage door, with fresh sealing floor paint (2023) New Kitchen cabinets (2022), New Double Oven (2022) , New Quartz Countertops (2022) New flooring

    Carlos Larraz Annapolis Properties LLC

    112 Harbour Sound Dr, Chester, MD 21619
  • /34

    $365,000

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

    28E Queen Mary Ct, Chester, MD 21619

    Just painted. One more thing allowing you to move right in and enjoy life overlooking the lake!Welcome to 28E Queen Mary Court — one of the largest condos in the sought-after Queens Landing community, offering 1,660 square feet of thoughtfully designed living space. This spacious 3-bedroom, 2.5-bath home is ideally positioned to take in the best of the neighborhood, with serene lake

    Justin Disborough Samson Properties

    28E Queen Mary Ct, Chester, MD 21619
  • /8

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    326 Hanna Ct, Chester, MD 21619

    Don't miss this incredible opportunity to own a spacious 4-bedroom home in sought-after Clayborne Woods at an exceptional price! Picture yourself relaxing by the gas fireplace, enjoying outdoor fun in the fenced backyard, or working/playing in the flexible space featuring stylish French doors. This is a rare find and won't last long – schedule your private tour today before it's gone!

    Kevin Waterman Coldwell Banker Waterman Realty

    326 Hanna Ct, Chester, MD 21619
  • /31

    $525,000 Open Sat 9AM - 11AM

    • 3 Beds
    • 2 Baths
    • 1,795 Sq Ft

    307 Skipper Ln, Chester, MD 21619

    Welcome to Your Refreshing New Home with First-Floor Living! This beautifully updated residence offers the perfect blend of comfort and convenience with three spacious bedrooms and two full baths, all on the main level. The expansive primary suite features a private, fully updated bath for your relaxation. The gorgeous kitchen is a true standout, boasting quartz countertops, brand new stainless

    Dee Dee McCracken Coldwell Banker Realty

    307 Skipper Ln, Chester, MD 21619
  • /57

    $349,900

    • 2 Beds
    • 2.5 Baths
    • 1,747 Sq Ft

    208 Ringneck Ct, Chester, MD 21619

    208 Ringneck Court is a great home for the smart buyer! The 2 bedroom, 2 1/2 bathroom GARAGE town-home, located in the Bayside community on the Chester River, underwent a MAJOR RENOVATION within the past 3 years. As you enter the south-facing home, you'll notice that the floor plan is a bit different than others...the kitchen has been reconfigured to create an open concept design which

    Phyllis Endrich Long & Foster Real Estate, Inc.

    208 Ringneck Ct, Chester, MD 21619
  • /29

    $559,850

    • 4 Beds
    • 2.5 Baths
    • 2,558 Sq Ft

    558 Cross Creek Ct, Chester, MD 21619

    Nestled in a highly desirable community, this stunning home offers over 2,500 sqft of spacious living on a large, wooded lot, ensuring privacy and tranquility. Move right into this freshly painted haven, featuring four generous bedrooms, including a luxurious primary suite with a massive walk-in closet and a spa-like ensuite bathroom—complete with a Jacuzzi tub and separate shower.Main

    Thomas Hennerty NetRealtyNow.com, LLC

    558 Cross Creek Ct, Chester, MD 21619
  • /72

    $364,900

    • 2 Beds
    • 2.5 Baths
    • 1,956 Sq Ft

    202 Ringneck Ct, Chester, MD 21619

    Seller New Home is Complete! Packing has started....Dont miss out, still time to enjoy summer near the water!Beautifully Updated End-Unit Townhouse in Sought-After Bayside Community!This spacious 2-bedroom, 2.5-bath end-unit townhome with a 1-car garage offers the perfect blend of comfort, style, and convenience. Step inside to discover a beautifully remodeled kitchen and updated

    Sheila Washburn Benson & Mangold, LLC

    202 Ringneck Ct, Chester, MD 21619
  • /23

    $359,900

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

    206 Blenny Ln, Chester, MD 21619

    Come see this town home with 1 car garage and offering 1900' of living space with interesting options on the first floor. Family room w/fp is connected to bright kitchen and sliders lead to 2nd floor deck. There are 3 Bedrooms and the Primary has a private bath with skylight. This light filled home is ready for your touches. New flooring on main level. Newer carpet on 3rd level. HVAC is

    Jimmy White Long & Foster Real Estate, Inc.

    206 Blenny Ln, Chester, MD 21619
  • /73

    $510,000

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

    170 Harrier Way Unit 22, Chester, MD 21619

    For a limited time, $4000 credit towards Capital Contribution Fee for full price offer.When I asked the seller what is the best part of living here, she said......"the best things about my place is the balcony and view !! Unobstructed. No buildings directly between my unit and the river". Easy place to live !! Lock the door and leave everything to someone else !!

    Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, Chester, MD 21619
  • /81

    $795,000

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

    170 Harrier Way Unit 34, Chester, MD 21619

    New improved price of $795,000 and immediate occupancy! No need to wait five months for a new condo to be built. Welcome to luxury condo living at Four Seasons at Kent Island, an active 55+ community packed with amenities. No need to wait for a new condo to be built – you can move in now to 170 Harrier Way #34. This third floor Severn model (3 BR / 2 1⁄2 Bath / 2,602 sqft) offers beautiful views

    Barry Davis Long & Foster Real Estate, Inc.

    170 Harrier Way Unit 34, Chester, MD 21619
  • /26

    $499,000

    • 2 Beds
    • 2 Baths

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Priced to Sell! Seller is ready for their next adventure! Move in, in May! Enjoy low-maintenance living in the amenity-rich, 55+ community of Four Seasons on Kent Island. This 2-bedroom, 2-bath home offers comfortable one-level living with an open layout, perfect for entertaining or relaxing. The property includes a 1-car garage with additional storage units—ideal for keeping your home organized

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • /59

    $498,000

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

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. With 1900 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 and kitchen, provide an open area for gatherings. The gourmet

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, Chester, MD 21619
  • /40

    $354,900

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

    8 Queen Victoria Way, Chester, MD 21619

    Upgraded two level townhouse, like new kitchen with granite counter tops, stainless steel appliances and ceramic floor on main level for easy cleaning. Wood burning fireplace and sliding doors to private patio that backs to common areas. Second level provides two bedrooms with vaulted ceilings and skylights, each with a private balcony. Two upgraded bathrooms, washer/dryer. Upgraded heating and

    Miguel Ruiz RE/MAX Realty Services

    8 Queen Victoria Way, Chester, MD 21619
  • /32

    $49,000

    • 960 Sq Ft

    5H Piney Narrows Rd, Chester, MD 21619

    Don't miss this opportunity to own this boat slip at Piney Narrows Yacht Haven! One of the most desirable locations at this marina. Slip H-5 is a covered 60' with a 16' beam. It has a finger pier access and 2-50 amps service. The Narrows is just minutes to Eastern Bay south or north to the Chesapeake Bay. Fishing these waters is like no other. Numerous species of fish, crabs and marine life

    Lisa Lynch Keller Williams Realty

    5H Piney Narrows Rd, Chester, MD 21619
  • /34

    $497,000

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

    807 Auckland Way, Chester, MD 21619

    PRICE REDUCED! Waterside Living on Kent Island! Discover the perfect blend of comfort and convenience in this spacious 3-bedroom, 3.5-bathroom condo located on Kent Island, in the Bayside Condominiums waterside community. This 3-level condo offers a wonderful combination of space, style, and serene coastal living.The open-concept main floor features a freshly painted, inviting living

    Andrew Spagnolo Samson Properties

    807 Auckland Way, Chester, MD 21619
  • /35

    $334,900

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

    308 Dominion Rd, Chester, MD 21619

    Charming Rancher in Chester, MD - Welcome to 308 Dominion Rd, a beautifully updated 3-bedroom, 2-bathroom rancher offering 1,280 sq. ft. of comfortable living space. Situated on a spacious 0.31-acre lot, this home features brand-new luxury vinyl plank flooring throughout the main areas, plush carpeting in the bedrooms, and a newly installed HVAC system for year-round comfort. The generously sized

    Tyler Burch Burch Real Estate Group, LLC

    308 Dominion Rd, Chester, MD 21619
  • /28

    $575,000

    • 3 Beds
    • 2.5 Baths
    • 2,342 Sq Ft

    114 Addison Ct, Chester, MD 21619

    **REDUCED** "Shiny and new" might be the best way to describe the feel of this lovely 3 bedroom, 2-1/2 bath home in the terrific Claybourne Woods community. The "new" includes a brand new roof, kitchen cabinets, granite kitchen counters, kitchen sink and faucet, wood floors downstairs and main level carpeting. The rest of the home is move-in ready and was just professionally cleaned. The

    Scott Saunders Coldwell Banker Waterman Realty

    114 Addison Ct, Chester, MD 21619
  • /41

    $499,950

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

    170 Harrier Way Unit 33, Chester, MD 21619

    This Chester model has scenic views of the river, beautiful sunrises, and an incredible display of wildlife in all seasons. Upgraded lighting package, dry bar, and fireplace are just a few of the features of this award winning condominium. With nearly 2000 square feet of open living space on one floor, this home has a great layout for entertaining friends and family. Spacious Great Room,

    Ralph Kennedy RE/MAX Executive

    170 Harrier Way Unit 33, Chester, MD 21619
  • /27

    $469,900

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

    1340 Queen Anne Dr, Chester, MD 21619

    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 accented with stylish

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • /17

    $300,000

    • Land
    • 0.68 Acre
    • $441,176 per Acre

    0 Parks Rd, Chester, MD 21619

    Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life

    Linda Austin Long & Foster Real Estate, Inc.

    0 Parks Rd, Chester, MD 21619
  • /35

    $2,050,000

    • 6 Beds
    • 5.5 Baths
    • 5,174 Sq Ft

    2817 Cox Neck Rd, Chester, MD 21619

    This stunning waterfront, custom built home sits ideally on a little over an acre fronting Crab Alley Bay in the prestigious Southwind community. Home boast almost 10,000 square feet, between finished living space and additional expansion space. An already large home offers so much more room to grow the perfect, waterfront retreat. This gem features 6 large bedrooms and of those 4 have private

    Michael Bozek Michael J. Bozek

    2817 Cox Neck Rd, Chester, MD 21619
  • /2

    $359,000

    • 3 Beds
    • 2.5 Baths
    • 1,635 Sq Ft

    7014 Bridgepointe Dr, Chester, MD 21619

    Welcome Home! This beautifully designed townhome features a bright and sunny kitchen that invites natural light to fill the space, perfect for cooking and entertaining. The high ceilings create an airy atmosphere, enhancing the open feel of the main level. The primary bedroom suite is conveniently located on the main level, offering privacy and ease of access. A stylish powder room is also

    Dee Dee Miller Long & Foster Real Estate, Inc.

    7014 Bridgepointe Dr, Chester, MD 21619
  • /10

    $539,900 New Construction

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

    121 Wheelhouse Way, Chester, MD 21619

    Home office with double doors near entry.Gourmet kitchen with central island for prep & dining.Dining area includes built-in dry bar.Great room features a sleek electric fireplace.Multi-slide glass doors open to rear patio.Owner’s suite with walk-in closet for storage.Spa-inspired owner’s bath with dual sinks.

    K Hovnanian's Four Seasons

    Magothy, Chester, MD 21619
  • /61

    $719,900 New Construction

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

    121 Wheelhouse Way Unit 2124, Chester, MD 21619

    This thoughtfully designed Severn condo offers 3 bedrooms and 2.5 bathrooms—blending comfort, style, and function. The owner’s suite features a private sitting room and spacious walk-in closets, creating a true retreat. A built-in dry bar and electric fireplace add warmth and charm to the living space.The kitchen is equipped with quartz countertops, gas cooktop, range hood, tile

    Mary Anne Kowalewski KOVO Realty

    121 Wheelhouse Way Unit 2124, Chester, MD 21619
  • /73

    $539,900 New Construction

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

    121 Wheelhouse Way Unit 2111, Chester, MD 21619

    This Magothy condo offers low-maintenance luxury with a smart layout and designer features. With 2 bedrooms, 2.5 bathrooms, a 1-car garage, and a dedicated home office with French doors, it’s the perfect mix of comfort and versatility. Enjoy cozy evenings by the electric fireplace or entertaining at the built-in dry bar.The kitchen includes quartz countertops, a gas cooktop, range hood,

    Mary Anne Kowalewski KOVO Realty

    121 Wheelhouse Way Unit 2111, Chester, MD 21619
  • /32

    $779,900 New Construction

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

    121 Wheelhouse Way, Chester, MD 21619

    Charming gourmet kitchen featuring designer cabinets & center island.Connected dining area & great room for seamless flow.Convenient dry bar & electric firepelace in main living spaces.Peaceful owner's suite & bath with walk-in closet.Organized home office for leisure activities.Versatile balcony for outdoor enjoyment.

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • /18

    $719,900 New Construction

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

    121 Wheelhouse Way, Chester, MD 21619

    Beautiful gourmet kitchen overlooks open concept living spaces.Spacious great room with warm fireplace.Sun-lit dining area with drybar, perfect for hosting dinner parties.Lavish owner's suite & bath featuring dual walk-in closets & sitting room.Convenient laundry room located near secondary bedrooms.Lovely balcony for outdoor relaxation.

    K Hovnanian's Four Seasons

    Severn, Chester, MD 21619
  • /58

    $784,900 New Construction

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

    201 Switchgrass Way Unit 1443, Chester, MD 21619

    Welcome home to the Chester, a beautifully crafted 2-bedroom, 2.5-bath residence with a 1-car garage, offering low-maintenance luxury and stylish finishes throughout. Ideal for full-time living or a lock-and-leave lifestyle, this home delivers comfort, flexibility, and charm in every room.Inside, you’ll find a dedicated home office with lighted French doors, perfect for remote work or a

    Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1443, Chester, MD 21619
  • /58

    $784,900 New Construction

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

    201 Switchgrass Way Unit 1442, Chester, MD 21619

    Experience the perfect balance of function and finesse in the Chester, a 2-bedroom, 2.5-bath home with a 1-car garage, designed for effortless living and elevated comfort.Thoughtfully laid out, this home includes a stylish home office with lighted French doors, a dry bar for entertaining, and a welcoming electric fireplace to anchor the living space. Elegant tray ceilings in both the great room

    Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1442, Chester, MD 21619
  • /45

    $999,900 New Construction

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

    327 Kingfisher Ln, Chester, MD 21619

    Welcome to the Tuscaloosa, a stunning 5-bedroom, 4.5-bath home designed for flexible living and modern style. With a 3-car garage, open-concept layout, and high-end finishes, this home is the perfect blend of comfort and sophistication.Enjoy thoughtful details throughout, including a cozy fireplace, versatile home office, bright loft, and a relaxing screened patio. The kitchen features a full

    Mary Anne Kowalewski KOVO Realty

    327 Kingfisher Ln, Chester, MD 21619
  • /25

    $784,900 New Construction

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

    201 Switchgrass Way, Chester, MD 21619

    Private home office with double doors for a quiet workspace.Central island anchors the gourmet kitchen with wall oven.Great room with a warm electric fireplace & balcony access.Dining area includes a dry bar, perfect for hosting.Owner’s suite offers a retreat with private balcony entry.Spa-like owner’s bath with dual vanities & modern

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • /25

    $784,900 New Construction

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

    201 Switchgrass Way, Chester, MD 21619

    Home office with elegant double-door entry.Gourmet kitchen with wall oven & oversized island.Dining area includes a built-in dry bar for entertaining.Great room with an electric fireplace & natural light.Access to the balcony from both the great room & owner’s suite.Dual vanities in the owner’s spa bath for a luxe feel.Smartly designed floorplan

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • /34

    $671,400 New Construction

    • 4 Beds
    • 2.5 Baths

    1501 Norman Rd, Chester, MD 21619

    One of our most popular designs, the Doral offers formal ( office space) and informal living areas with lots of room for the whole family to spread out. Your main level features a spacious family room and table space kitchen. Add a light-filled morning room off the rear or expand your space with plan extension. Upstairs, plans accommodate 4 nicely sized bedrooms, 2 full baths and large laundry

    George Bailey Keller Williams Flagship

    1501 Norman Rd, Chester, MD 21619
  • /56

    $849,500 Open Fri 11AM - 3PM

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

    223 Broadwater Dr, Chester, MD 21619

    ****************Welcome to Your Dream Home at Four Seasons on Kent Island*******************Step into refined elegance and low-maintenance luxury living with this stunning Killarney w/Loft model, the most sought-after floor plan in the exclusive Four Seasons at Kent Island community. This single family home blends style, comfort, and functionality, in one of the Eastern Shore's premier 55+

    Ralph Kennedy RE/MAX Executive

    223 Broadwater Dr, Chester, MD 21619
  • /38

    $805,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,065 Sq Ft

    104 Woods Rd, Chester, MD 21619

    FANTASTIC HOME! THE COMPLETE PACKAGE AND THEN MORE! TWO PRIMARY BEDROOM/BATH SUITES! BOTH WITH GIANT WALK IN CLOSETS! EACH PRIMARY BATH HAS A STEP IN SHOWER, DOUBLE STONE VANITY PLUS SOAKING TUB! THIS HOME HAS A TOTAL OF 5 BEDROOMS PLUS 3 AND ONE HALF BATHS! PLENTY OF SPACE FOR THE HOME OFFICE! THE OPEN KITCHEN IS FULLY UPDATED WITH ISLAND, STAINLESS STEEL DOUBLE OVENS, COOKTOP, DRAWER

    Temple Peirce Cummings & Co. Realtors

    104 Woods Rd, Chester, MD 21619

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