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Homes for Sale in 21619

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  • /55

    $1,050,000 Open Thu 5PM - 7PM

    • 4 Beds
    • 3.5 Baths
    • 3,949 Sq Ft

    330 Macum Creek Dr, Chester, MD 21619

    Welcome home to luxurious living Gibson's Grant! This stunning home offers a perfect blend of luxury and functionality, featuring extensive upgrades throughout. The backyard is an entertainer’s dream with a custom patio, covered outdoor kitchen, bonus grassy area for pets or play, and a fully fenced yard. A former screened porch has been converted into a bright and inviting four-season sunroom,

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 256-7961

    330 Macum Creek Dr, Chester, MD 21619
  • /62

    $530,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - $10,000 Closing Cost Assistance Available - Turn Key & 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

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 936-3917

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • /57

    $469,000

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

    34 Queen Anne Way, Chester, MD 21619

    Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water-privileged resort-style community of Queen's Landing, along the scenic Chester River and Macum Creek off the Chesapeake Bay. Step into the light-filled foyer and head up the stairs to the main level, you will find this lovely 2 bedroom, 2.5 bath condominium is move in ready. Just bring your patio chairs,

    Agent Photo

    Lona Todd

    Taylor Properties

    (667) 291-8898

    34 Queen Anne Way, Chester, MD 21619
  • /74

    $499,000

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

    170 Harrier Way Unit 11, Chester, MD 21619

    ***Redfin powered by Rocket Mortgage Preferred Pricing*** Enjoy with a 1% lower interest rate for your initial year or potential savings of up to $6,000 on your closing costs when you finance with Rocket Mortgage*** Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent

    Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
  • /43

    $465,000

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

    54A Queen Caroline Ct, Chester, MD 21619

    Darlene Winegardner RE/MAX Executive

    54A Queen Caroline Ct, Chester, MD 21619
  • /12

    $872,900 New Construction

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

    Mykonos, 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

    K Hovnanian's Four Seasons

    Mykonos, Chester, MD 21619
  • /26

    $807,900 New Construction

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

    Kerr, 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.

    K Hovnanian's Four Seasons

    Kerr, Chester, MD 21619
  • /24

    $659,900 New Construction

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

    Jenkins II, 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.

    K Hovnanian's Four Seasons

    Jenkins II, Chester, MD 21619
  • /10

    $740,900 New Construction

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

    Taylor, 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.

    K Hovnanian's Four Seasons

    Taylor, Chester, MD 21619
  • /12

    $474,990 New Construction

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

    Magothy, Chester, MD 21619

    Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owner’s suite with spa bath . Fantastic great room with large windows for your viewing pleasure. Large secondary bedroom with opt. door to access patio. Pricing is

    K Hovnanian's Four Seasons

    Magothy, Chester, MD 21619
  • /27

    $844,900 New Construction

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

    Franklin, 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.

    K Hovnanian's Four Seasons

    Franklin, Chester, MD 21619
  • /40

    $836,900 New Construction

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

    Tuscaloosa, 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.

    K Hovnanian's Four Seasons

    Tuscaloosa, Chester, MD 21619
  • /47

    $619,900

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

    224 Bayberry Dr, Chester, MD 21619

    Discover the charm of this meticulously maintained, one-owner Donegal model nestled in the highly desirable, water-privileged 55+ community of Four Seasons at Kent Island. This stunning single-family home features an expansive open-concept layout, enhanced with designer lighting and custom finishes that elevate the home's ambiance.Step into a spacious kitchen that serves as the heart of

    Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
  • /39

    $569,000

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

    25 Queen Elizabeth Ct, Chester, MD 21619

    Experience breathtaking sunrises over the Chester River and Chesapeake Bay from this beautifully updated, three-level townhouse-style condo. Located in a serene waterfront community, this home offers the perfect blend of modern amenities and natural beauty. The front entrance welcomes you with a porcelain-tile foyer and a river-rock inset, leading into an open living area with stunning water

    Evguenia Mathur Samson Properties

    25 Queen Elizabeth Ct, Chester, MD 21619
  • /39

    $479,000

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

    312 Blenny Ln, Chester, MD 21619

    You do not want to miss this opportunity to enjoy island living in this maintenance free, WATER 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

    Judith Brown Samson Properties

    312 Blenny Ln, Chester, MD 21619
  • /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
  • /79

    $529,500

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    49 Queen Guinivere Way, Chester, MD 21619

    Welcome to Queens Landing, where resort-style living meets the comfort of home. This beautifully updated townhome offers 1,440 square feet of thoughtfully designed living space plus an open sunroom, adding approximately 160 additional square feet, creating a seamless and spacious floor plan ideal for everyday living and entertaining.Enjoy panoramic water views from every room - lake and fountain

    Julia Stevens Realty Navigator

    49 Queen Guinivere Way, Chester, MD 21619
  • /68

    $539,000

    • 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
  • /36

    $715,000

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    242 Peregrine Dr, Chester, MD 21619

    Introducing the Simone – Where Modern Comfort Meets Farmhouse Charm. This 6 month old Simone offers the perfect blend of open-concept living and timeless Farmhouse style with 4 spacious bedrooms, 3 full baths, and a 2-car garage, this home is designed with both functionality and flair. Step inside to find stylish laminate flooring flowing through the foyer, hallways, home office, great room,

    Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Chester, MD 21619
  • /45

    $649,400

    • 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

    $750,000

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

    132 Claiborne St, Chester, MD 21619

    Sitting pretty on one of the largest, level lots in the prestigious Gibson's Grant Community, w/ beautiful landscaping, flowers now blooming, and a lawn irrigation system. The lot is enhanced with landscape lighting and a wood fence. This front porch Chatham model is inviting w/sidewalk extension and has a good view of the peaceful pond and natural surroundings. The foyer and main level have

    Melanie Mcknight RE/MAX Professionals

    132 Claiborne St, Chester, MD 21619
  • /49

    $788,000

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

    1868 Roberta Dr, Chester, MD 21619

    Price improvement.Welcome to this exceptional custom-built home by Lacrosse Builders, nestled in a desirable water-oriented community with partial water views. Designed for comfort, function, and style, this home offers high-end finishes, generous spaces, and thoughtful upgrades throughout.Step inside to find 9’ ceilings on the main level, expansive 6’ windows that fill the home with

    David Kaufmann Eastern Shore Real Estate, LLC

    1868 Roberta Dr, Chester, MD 21619
  • /51

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,564 Sq Ft

    1771 Harbor Dr, Chester, MD 21619

    This beautifully crafted waterfront home boasts five spacious bedrooms and 2.5 baths, offering ample space for comfortable living. The expansive layout includes multiple living areas, ideal for both relaxation and entertainment. The sunroom, with its wall-to-wall sliding doors, provides stunning views of the water, while the family room features a cozy fireplace. A separate formal living room and

    Dee Dee McCracken Coldwell Banker Realty

    1771 Harbor Dr, Chester, MD 21619
  • /10

    $541,900 New Construction

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

    121 Wheelhouse Way, Chester, MD 21619

    Efficient gourmet kitchen featuring vast center island & designer cabinets.Cozy electric fireplace adds character & warmth to great room.Refined dining area featuring convenient dry bar.Lavish owner's suite & spa bath with walk-in closet.Productive home office with double doors.Inviting covered patio for relaxing outdoors.

    K Hovnanian's Four Seasons

    Magothy, Chester, MD 21619
  • /21

    $559,990 New Construction

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

    Severn, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K Hovnanian's Four Seasons

    Severn, Chester, MD 21619
  • /12

    $869,900 New Construction

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

    Munich ESP, 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.

    K Hovnanian's Four Seasons

    Munich ESP, Chester, MD 21619
  • /11

    $762,900 New Construction

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

    Kelly, 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.

    K Hovnanian's Four Seasons

    Kelly, Chester, MD 21619
  • /13

    $691,900 New Construction

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

    Simone, 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

    K Hovnanian's Four Seasons

    Simone, Chester, MD 21619
  • /12

    $626,900 New Construction

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

    Bernstein II, 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.

    K Hovnanian's Four Seasons

    Bernstein II, 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
  • /45

    $484,900

    • 4 Beds
    • 2.5 Baths
    • 1,988 Sq Ft

    312 Hanna Ct, Chester, MD 21619

    Welcome home to 312 Hanna Ct, situated in the sought-after Community of Clayborne Woods, a picturesque property that offers a tranquil lifestyle, embodying the serene charm of the Eastern Shore.Upon entering, you’ll discover beautiful luxury vinyl plank flooring throughout the main living area. The family room features elegant vaulted ceilings and an exquisite wood-burning fireplace,

    Justin Kennedy Samson Properties

    312 Hanna Ct, Chester, MD 21619
  • /34

    $285,000

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

    211 Golden Eye Ct, Chester, MD 21619

    Discover this impeccably cared-for 2-bedroom, 2-bathroom condo, offering the ultimate in low-maintenance living within one of Kent Island’s most desirable neighborhoods. This second floor unit boasts an open-concept living and dining area that creates a warm, inviting space perfect for both relaxing and entertaining. Enjoy peace and tranquility on your personal balcony. The Bayside community

    Brendan Noone Coldwell Banker Realty

    211 Golden Eye Ct, Chester, MD 21619
  • /46

    $334,900

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

    31C Queen Anne Way, Chester, MD 21619

    Welcome to 31-C Queen Anne Way, a beautifully updated two-bedroom, 1.5-bath located in Condo located in the desirable waterfront community of Queens Landing. This well-maintained unit offers 1,104 square feet of thoughtfully designed living space spread across the second and third levels. Enjoy unobstructed views of Lake Amletto and the community water tower, along with partial but striking

    Julia Stevens Realty Navigator

    31C Queen Anne Way, Chester, MD 21619
  • /41

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    2723 Cox Neck Rd, Chester, MD 21619

    Harbor View - New Construction ready for you to move into! This home features 4 Bedrooms 2 1/2 baths. Offering a first-floor bedroom or this would be a great office as well. Upgraded LVP flooring on the first floor and all bathrooms. The kitchen features granite countertops, stainless steel appliance and 42" American Woodmark Cabinets. The home is quality built with 2x6 construction,

    Linda Austin Long & Foster Real Estate, Inc.

    2723 Cox Neck Rd, Chester, MD 21619
  • /26

    $510,000

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

    1872 Harbor Dr, Chester, MD 21619

    Just Listed in the Sought-After Harbor View Community! Premium Corner Lot | Nearly Acre | Fully Renovated Brick Rancher -Tucked away on a rare, oversized corner lot in the desirable Harbor View neighborhood, this beautifully updated home offers comfort, style, and function on almost three-quarters of an acre (2 lots). The kitchen showcases sleek countertops, refreshed cabinetry, and a full suite

    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
  • /25

    $295,000

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

    204 Teal Ct Unit B, Chester, MD 21619

    Lakefront Condo in Premier Community! Don’t miss your chance to own this stunning ground-floor condo with serene lake views from every room—including the soothing sights and sounds of a peaceful fountain just outside your window. Located in an amenity-rich, highly desirable community offering:• Clubhouse• Fitness Center• Sparkling Pool• Tennis Courts• Restaurants &

    Thomas Hennerty NetRealtyNow.com, LLC

    204 Teal Ct Unit B, Chester, MD 21619
  • /60

    $354,900

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    35 F Queen Anne Way, Chester, MD 21619

    Welcome to 35F Queen Anne Way in Queens Landing! This lakefront updated home offers 2 bedrooms and 2 full bathrooms. Updates include a spacious kitchen and both bathrooms. Wake up to lakefront views from the spacious primary bedroom and enjoy a cup of coffee or a glass of wine on the back patio or three season room while gazing over the lake. A stones throw away is the scenic Chester River

    Lawrence Doyle Long & Foster Real Estate, Inc.

    35 F Queen Anne Way, 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

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