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Houses for Sale in 21619

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  • /10

    $744,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    Taylor Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Secluded bedroom 2 and bath off foyer for overnight guests. Stylish home office off foyer for working from home. Open & airy great room with adjacent dining area. Striking kitchen with island & tons of cabinet space. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with roomy shower. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36474700, Chester, MD 21619
  • /12

    $876,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    Mykonos Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36477689, Chester, MD 21619
  • /27

    $848,900 New Construction

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

    Franklin Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Formal dining room off foyer for entertaining guests. Stylish kitchen with plenty of cabinet space and large island. Open and airy great room with slider to covered patio. Luxurious primary suite with triple windows. Private primary bath with optional freestanding tub. Convenient 2-car garage with storage space.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • /24

    $663,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - River Series, Chester, MD 21619

    Private home office for working from home. Stylish kitchen with large center island and spacious pantry. Spacious great room with slider to covered patio. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with split vanities. Convenient HovHall off garage for keeping home tidy.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36466218, Chester, MD 21619
  • /26

    $811,900 New Construction

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

    Kerr Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage for additional storage space.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • /40

    $840,900 New Construction

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

    Tuscaloosa Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Extra Suite with full bath for overnight guests. Private home office off foyer for working from home. Spacious great room with adjacent dining area. Beautiful kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • /76

    $700,000

    • 4 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    157 John Gibson Dr, Chester, MD 21619

    Welcome to this stunning colonial, in the amenity-rich and highly sought-after community of Gibson’s Grant! This 4-bedroom, 2.5-bath colonial offers the perfect blend of comfort, style, and functionality—all just minutes from the Bay Bridge. The main level features an inviting open floor plan with tile flooring, hardwoods in the dining room, and a dedicated office with custom built-in shelving.

    Ryan Briggs Anne Arundel Properties, Inc.

    157 John Gibson Dr, Chester, MD 21619
  • /38

    $2,259,000

    • 4 Beds
    • 3.5 Baths
    • 5,122 Sq Ft

    2865 Cox Neck Rd, Chester, MD 21619

    An impressive open two-story foyer welcomes you to this custom 4 BR, 3.5BA waterfront residence on 1.9 acres boasting an enchanting open space floorplan. A first floor Ensuite BR has a walk-in closet plus a separate jacuzzi and shower in the updated full bath. The sumptuous approximately 39'X26' Primary Suite with a large sitting room area offers front and rear balconies specifically designed by

    Michele Sinclair Long & Foster Real Estate, Inc.

    2865 Cox Neck Rd, Chester, MD 21619
  • /50

    $925,000

    • 3 Beds
    • 5 Baths
    • 2,818 Sq Ft

    635 Dominion Rd, Chester, MD 21619

    Beautiful waterfront property in Chester that is so unique in every way offering five levels that starts off with the first level two car garage, spacious carport outside and huge laundry room , half bath and storage area inside* Second level has front door entrance to foyer as well as the connecting stairs from first level, beautiful family room with a gallery of windows offering expansive views

    Constance Golihew Coldwell Banker Realty

    635 Dominion Rd, Chester, MD 21619
  • /80

    $949,900

    • 3 Beds
    • 4 Baths
    • 3,494 Sq Ft

    130 Sunrise Ct, Chester, MD 21619

    Welcome to Four Seasons at Kent Island, where luxury and comfort meet coastal living. This stunning Santorini model at the end of a cul-de-sac with loft offers 3 bedrooms, 4 full baths, and thoughtfully curated designer upgrades throughout. From the moment you step inside, you’ll feel the ease of open-concept living — soaring 10’ ceilings, cozy gas fireplace, abundant natural light, neutral color

    Meg Richardson Engel & Völkers Annapolis

    130 Sunrise Ct, Chester, MD 21619
  • /45

    $1,049,000 Open Sat 11AM - 1PM

    • 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

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, Chester, MD 21619
  • /45

    $847,500

    • 3 Beds
    • 3 Baths
    • 2,583 Sq Ft

    124 Nauset Ln, Chester, MD 21619

    NEW UPDATED PHOTOS!! Take another look!Turnkey Luxury with Over $175K in Upgrades – Four Seasons at Kent IslandThis beautifully enhanced Killarney with Loft model in Phase I offers the ultimate in resort-style living, featuring over $100K in builder upgrades and $75K in custom renovations. To build this home new through the builder would be over 1 million dollars. For added peace

    Jennifer Thomas RE/MAX Executive

    124 Nauset Ln, Chester, MD 21619
  • /38

    $795,000 Open Sun 11AM - 1PM

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

    104 Woods Rd, Chester, MD 21619

    OPEN SUNDAY 9/21/25 11;00AM -1:00PM PERFECT MULTI GENERATIONAL HOME!!!! LIST PRICE ADJUSTED !!FANTASTIC HOME! THE COMPLETE PACKAGE AND THEN MORE! INGROUND POOL! 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

    Temple Peirce Cummings & Co. Realtors

    104 Woods Rd, Chester, MD 21619
  • /37

    $1,195,000 Open Sat 1:30PM - 3:30PM

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft

    162 Kirwans Landing Ln, Chester, MD 21619

    Welcome to 162 Kirwans Landing Lane—a beautifully updated residence located in the sought-after, water-privileged community of Kirwans Landing. Set on 1.4 private acres, this 4-bedroom, 2.5-bath home offers a seamless blend of refined comfort and exceptional outdoor living.Inside, you’ll find hardwood floors throughout both levels, a renovated kitchen with granite countertops, custom

    Brad Kappel TTR Sotheby's International Realty

    162 Kirwans Landing Ln, Chester, MD 21619
  • /45

    $639,500

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

    154 Harrier Way, Chester, MD 21619

    *** WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND***The Donegal model is a spacious and airy 2 bedroom, 2 bath home boasting an expansive open floor plan with nearly 2000 square feet of luxurious living space on one level. This home features a lavish gourmet kitchen and dining area, a spacious and airy great room with gas fireplace, plus office or den. You decide! The

    Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
  • /77

    $725,000

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    132 Claiborne St, Chester, MD 21619

    Set on a rare, level, oversized lot in sought-after Gibson’s Grant, this inviting front-porch Chatham model pairs polished interiors with flexible living spaces and standout outdoor amenities. Manicured landscaping (with irrigation), landscape lighting, and a fully fenced yard frame serene views of the community pond and natural surroundings. Inside, a neutral palette and hardwoods flow through

    Melanie Mcknight RE/MAX Professionals

    132 Claiborne St, 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
  • /20

    $919,900 New Construction

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

    519 Warbler Way, Chester, MD 21619

    Convenient Extra Suite for guests to stay overnight. Functional home office off foyer for working from home. Breathtaking kitchen with Winstead Maple Flagstone cabinetry. Beautiful Calacatta Abezzo quartz countertops & island. Refined great room & equisite fireplace. Intimate dining area for hosting dinner parties. Private primary suite & spa-like bath with dual vanities. Stunning screened patio

    Builder Photo

    K. Hovnanian Homes

    Builder

    519 Warbler Way, Chester, MD 21619
  • /31

    $1,125,000 New Construction

    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    To be built. WATERFRONT DEEP WATERThe Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for entertaining and an enhanced lifestyle!

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
  • /13

    $695,900 New Construction

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

    Simone Plan at K. Hovnanian’s® Four Seasons at Kent Island - River Series, Chester, MD 21619

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

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • /12

    $630,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    Bernstein II Plan at K. Hovnanian’s® Four Seasons at Kent Island - River Series, Chester, MD 21619

    Elegant foyer welcoming guests to your home. Convenient single-story living. Kitchen with spacious pantry and oversized island. Open-concept great room and dining area adjacent to kitchen. Private primary suite with large walk-in closet and spa bath. Laundry room and HovHall with plenty of space to store and organize.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36492116, Chester, MD 21619
  • /11

    $766,900 New Construction

    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    Kelly Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Private home office for working from home. Spacious great room with slider to covered patio. Beautiful kitchen with large island and roomy pantry. Luxurious primary suite with triple windows. Relaxing primary bath with spacious shower and walk-in closet. Convenient covered patio with screen patio option.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36471203, Chester, MD 21619
  • /12

    $873,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,601 Sq Ft

    Munich ESP Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Extra Suite Plus for multi-generational living. Striking kitchen with large center island and corner pantry. Spacious great room with tons of windows for natural sun light. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities and optional freestanding tub. Private home office off foyer for working from home. Large covered patio for enjoying the

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36455262, Chester, MD 21619
  • /34

    $722,369 New Construction

    • 4 Beds
    • 2.5 Baths

    1501 Norman Rd, Chester, MD 21619

    Home for the holidays. Under construction in Marling Farms.One of our most popular homes, the newly designed Doral offers formal dining or( 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. Upstairs, plans accommodate light filled primary with super bath and HUGE Closet plus 3

    George Bailey Keller Williams Flagship

    1501 Norman Rd, Chester, MD 21619
  • /2

    $775,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,791 Sq Ft

    123 Bentons Pleasure Rd, Chester, MD 21619

    Discover the charm of this stunning Colonial home nestled in the desirable Bentons Pleasure neighborhood. With 2,791 sq. ft. of thoughtfully designed living space, this residence boasts four spacious bedrooms and 2.5 baths, perfect for both relaxation and entertaining. The well equipped kitchen invites culinary creativity, while the semi open floor plan seamlessly connects the dining and living

    Tricia Wilson Wilson Realty & Staging LLC

    123 Bentons Pleasure Rd, Chester, MD 21619
  • /23

    $415,000

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

    1839 Harbor Dr, Chester, MD 21619

    Opportunity Knocks!Welcome 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, extra counter

    Greg Koch Taylor Properties

    1839 Harbor Dr, Chester, MD 21619
  • /41

    $439,900

    • 4 Beds
    • 3 Baths
    • 1,682 Sq Ft

    1903 Churchhill Ln, Chester, MD 21619

    Welcome Home to 1903 Churchhill Lane! This Beautifully updated Rancher offers the space you need to create a life you desire. Boasting an array of sleek finishes throughout this 4 Bedroom, 3 Bathroom home has so much to offer!!

    Lois Alberti Alberti Realty, LLC

    1903 Churchhill Ln, Chester, MD 21619
  • /33

    $469,000

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

    1401 Calvert Rd, Chester, MD 21619

    Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - PRICE REDUCED - 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 beths, one with a tub, one with a walkin shower - fabulous sunroom addition - quiet office area - updated kitchen with granite counters, newer

    Suzanne Hitt Coldwell Banker Waterman Realty

    1401 Calvert Rd, Chester, MD 21619
  • /51

    $610,000

    • 2 Beds
    • 2 Baths
    • 1,913 Sq Ft

    224 Bayberry Dr, Chester, MD 21619

    Welcome to Easy Living on the Eastern Shore! ***Discover the perfect blend of comfort, style, and resort-style living in this impeccably maintained, one-owner home — tucked into the highly sought-after, water-privileged 55+ community of Four Seasons at Kent Island.From the moment you walk in, you’ll notice the difference. The open-concept floor plan is thoughtfully designed and

    Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
  • /42

    $569,900 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,374 Sq Ft

    315 Cross Creek Ct, Chester, MD 21619

    You are going to love this bright and spacious home providing almost 2400 feet of living space. Fabulous floor plan with architectural accents that are sure to please. Hardwood floors greet and carry you through the main level, seamlessly connecting the living areas.The bright kitchen overlooks the family room and boasts gorgeous Quartz counter tops, a stylish subway back splash,

    Jimmy White Long & Foster Real Estate, Inc.

    315 Cross Creek Ct, Chester, MD 21619
  • /2

    $19,500

    • 2 Beds
    • 1 Bath
    • 764 Sq Ft

    1405 Little Creek Rd, Chester, MD 21619

    This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.Please note that

    Dustin Parker The Parker Group

    1405 Little Creek Rd, Chester, MD 21619
  • /24

    $455,000 Open Sat 11AM - 1PM

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

    1872 Harbor Dr, Chester, MD 21619

    1872 Harbor Drive, Chester, MDHarbor View Community | Corner Lot | Renovated Rancher with Room to GrowWelcome to 1872 Harbor Drive in the Harbor View neighborhood of Chester, Maryland—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

    Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • /19

    $299,000

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

    1906 Harbor Dr, Chester, MD 21619

    Great opportunity for a savvy investor to buy way below market value. This 3 brm 2 ba rancher, can easily be converted to a 4 brm. Needs work! Sold Strictly AS IS. Seller never occupied the property, therefore cannot guarantee accuracy in this listing, especially regarding utilities, well and sewer. Buyer must do their own due diligence before submitting an offer.

    Alex Fox Allfirst Realty, Inc.

    1906 Harbor Dr, Chester, MD 21619
  • /44

    $550,000

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

    205 Anchor Ln, Chester, MD 21619

    OPEN HOUSE, Sunday, 9/14, 3-4pm...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
  • /32

    $500,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 2,180 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
  • /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
  • /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
  • /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
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