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Chester, MD Homes for Sale

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  • 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
    /62

    $557,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - 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 with quartz counters, propane gas cooktop

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 936-3917

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    /10

    $499,900

    • 3 Beds
    • 2.5 Baths
    • 1,791 Sq Ft

    108 Bodys Neck Rd, Chester, MD 21619

    Coming Soon in Bayside on Kent Island – Resort-Style Island Living with Unmatched Water Views!Discover the perfect blend of coastal charm and modern luxury in this rarely available, oversized end-unit townhome Perfectly positioned to capture unobstructed, sweeping water views, this meticulously updated 3-bedroom, 2.5-bath home offers a true resort-style experience in one of the Eastern Shore’s

    Bill Longest Realty Navigator

    108 Bodys Neck Rd, Chester, MD 21619
  • 49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    /71

    $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
  • 205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    205 Anchor Ln, Chester, MD 21619
    /47

    $575,000

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

    205 Anchor Ln, Chester, MD 21619

    Need more room? This expansive home is ready to welcome your whole family! With 5 bedrooms, 3 full bathrooms and a 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 porch that’s perfect for relaxing

    Darlene Winegardner RE/MAX Executive

    205 Anchor Ln, Chester, MD 21619
  • 112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, 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
  • 129 Kirwans Landing Ln, Chester, MD 21619
    129 Kirwans Landing Ln, Chester, MD 21619
    129 Kirwans Landing Ln, Chester, MD 21619
    /61

    $1,165,000

    • 4 Beds
    • 2.5 Baths
    • 2,630 Sq Ft

    129 Kirwans Landing Ln, Chester, MD 21619

    Peaceful Coastal Living in One of Kent Island’s Most Sought-After Communities!Tucked away on 1.01 beautifully landscaped acres, this four bedroom, two full and one half bath porch front home, is a retreat unto itself and is located in one of Kent Island’s most exclusive and rarely available neighborhoods—complete with its own private marina just down the street. Inside, this stylish home offers a

    Noah Mumaw Monument Sotheby's International Realty

    129 Kirwans Landing Ln, Chester, MD 21619
  • 558 Cross Creek Ct, Chester, MD 21619
    558 Cross Creek Ct, Chester, MD 21619
    558 Cross Creek Ct, Chester, MD 21619
    /22

    $579,000

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

    558 Cross Creek Ct, Chester, MD 21619

    Welcome to your future home located in the highly sought after Clayborne Woods neighborhood, on a large corner wooded lot. Property boasts over 2500 usable square footage. Enter into a 2 story foyer with all new LVT on the entire level. Huge dining, separate eat in kitchen, 1/2 bath, family room with fireplace. Plus an added wing for your imagination that over looks a private wooded lot.?

    Thomas Hennerty NetRealtyNow.com, LLC

    558 Cross Creek Ct, Chester, MD 21619
  • 242 Peregrine Dr, Chester, MD 21619
    242 Peregrine Dr, Chester, MD 21619
    242 Peregrine 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
  • 1614 Postal Rd, Chester, MD 21619
    1614 Postal Rd, Chester, MD 21619
    1614 Postal Rd, Chester, MD 21619
    /43

    $624,900

    • 5 Beds
    • 2.5 Baths
    • 2,656 Sq Ft

    1614 Postal Rd, Chester, MD 21619

    OPEN HOUSE Saturday 5/31 from 10:30-12:30pm! Welcome to this Lovingly and Well-Maintained Colonial Style Home zoned Residential and Commercial! Looking for a Home based business? This one is it, as it offers a rare opportunity with incredible versatility with Town Center Zoning, making it perfect for a private residence, bed & breakfast, Airbnb, or the opportunity to live where you work.

    Pamela Ackermann-Doll RE/MAX Executive

    1614 Postal Rd, Chester, MD 21619
  • 194 Sailcloth Way, Chester, MD 21619
    194 Sailcloth Way, Chester, MD 21619
    194 Sailcloth Way, Chester, MD 21619
    /61

    $825,000

    • 3 Beds
    • 3 Baths
    • 2,453 Sq Ft

    194 Sailcloth Way, Chester, MD 21619

    Welcome to your dream home situated on a coveted premium lot that backs to the woods giving you endless views of wildlife. The first-floor living is ideal for all homeowners and offers you a large primary bedroom, an office/2nd bedroom and a completely open concept on the main level. The kitchen boasts custom cabinets, stainless steel appliances, double oven, gas range with exhaust hood and

    Ross Hunsberger Coldwell Banker Realty

    194 Sailcloth Way, Chester, MD 21619
  • 203 Schooner Way, Chester, MD 21619
    203 Schooner Way, Chester, MD 21619
    203 Schooner Way, Chester, MD 21619
    /18

    $405,000

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

    203 Schooner Way, Chester, MD 21619

    PRICE IMPROVEMENT!! Spring is here! Looking for place to call home? Come see this charming 3-bedroom, 2.5-bath townhouse offers the perfect blend of comfort and convenience. Located in a sought-after community on Kent Island.. With new flooring throughout and freshly painted walls, the home feels modern and inviting. The spacious kitchen boasts sleek stainless steel appliances, while two cozy

    Shandell Green Douglas Realty, LLC

    203 Schooner Way, Chester, MD 21619
  • 154 Harrier Way, Chester, MD 21619
    154 Harrier Way, Chester, MD 21619
    154 Harrier Way, Chester, MD 21619
    /45

    $649,400 Open Sat 11AM - 5PM

    • 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 centerpiece

    Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
  • 103 John Gibson Dr, Chester, MD 21619
    103 John Gibson Dr, Chester, MD 21619
    103 John Gibson Dr, Chester, MD 21619
    /62

    $789,000

    • 4 Beds
    • 3 Baths
    • 3,543 Sq Ft

    103 John Gibson Dr, Chester, MD 21619

    PRICE REDUCED!!!! Freshly painted and ready to go! Take a tour of this beautiful home in the sought after community of Gibsons Grant on Kent Island. This home rests just minutes from the Chesapeake Bay Bridge, Annapolis, Baltimore or DC. Everything in this home has been meticulously cared for. You will find ceramic tile flooring as you enter transitioning to beautiful plank flooring

    Edward Beres RE/MAX Executive

    103 John Gibson Dr, Chester, MD 21619
  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /38

    $789,000 Open Sun 11AM - 2PM

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

    1868 Roberta Dr, Chester, MD 21619

    Custom-built home with premium upgrades and stunning water views! This exceptional property features 9’ ceilings and expansive 6’ windows on the first floor, allowing for abundant natural light. Beautiful custom hardwood and tile flooring flow throughout the home. The spacious eat-in kitchen boasts granite countertops, a large center island, a pantry, and an adjoining sunroom for added charm. A

    David Kaufmann EXIT On The Bay

    1868 Roberta Dr, Chester, MD 21619
  • 1771 Harbor Dr, Chester, MD 21619
    1771 Harbor Dr, Chester, MD 21619
    1771 Harbor Dr, Chester, MD 21619
    /51

    $750,000 Open Sat 12PM - 2PM

    • 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
  • 114 Addison Ct, Chester, MD 21619
    114 Addison Ct, Chester, MD 21619
    114 Addison Ct, Chester, MD 21619
    /26

    $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
  • 516 Warbler Way, Chester, MD 21619
    516 Warbler Way, Chester, MD 21619
    516 Warbler Way, Chester, MD 21619
    /51

    $684,900 New Construction

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

    516 Warbler Way, Chester, MD 21619

    Charming Comfort & Elevated Style – Jenkins, Lot 602 | Move-In September 2025Welcome to the Jenkins, a thoughtfully designed 2-bedroom, 2-bath home with a 2-car garage and open layout ideal for modern living. This layout includes a versatile home office, a peaceful screened patio, and a stunning 2-story stone fireplace—the perfect focal point for the great room.The kitchen is equipped with

    Mary Anne Kowalewski KOVO Realty

    516 Warbler Way, Chester, MD 21619
  • 416 Warbler Way, Chester, MD 21619
    416 Warbler Way, Chester, MD 21619
    416 Warbler Way, Chester, MD 21619
    /51

    $669,900 New Construction

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

    416 Warbler Way, Chester, MD 21619

    Easy Living with Stylish Touches – Jenkins, Lot 597 | Move-In August 2025Step into comfort and convenience with the Jenkins—a 2-bedroom, 2-bath home with a 2-car garage, offering a smart layout and refined finishes. Designed for relaxed living, this home features a dedicated home office and a screened patio—perfect for quiet mornings or entertaining guests.The open-concept kitchen shines with

    Mary Anne Kowalewski KOVO Realty

    416 Warbler Way, Chester, MD 21619
  • 524 Warbler Way, Chester, MD 21619
    524 Warbler Way, Chester, MD 21619
    524 Warbler Way, Chester, MD 21619
    /39

    $639,900 New Construction

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

    524 Warbler Way, Chester, MD 21619

    Easy Living Meets Timeless Style – Bernstein II, Lot 604Available for settlement in Summer 2025, the Bernstein II is a beautifully designed 2-bedroom, 2-bath home offering low-maintenance, single-level living with thoughtful upgrades throughout.Step inside to find Luxury Vinyl Plank flooring flowing throughout the main living areas, creating a warm, cohesive space that’s both stylish and durable.

    Mary Anne Kowalewski KOVO Realty

    524 Warbler Way, Chester, MD 21619
  • 211 Switchgrass Way Unit 1532, Chester, MD 21619
    211 Switchgrass Way Unit 1532, Chester, MD 21619
    211 Switchgrass Way Unit 1532, Chester, MD 21619
    /48

    $639,900 New Construction

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

    211 Switchgrass Way Unit 1532, Chester, MD 21619

    The Chester is an elegant home that effortlessly blends a spacious open floorplan with timeless Legacy design elements. With a projected settlement date in September 2025, it promises modern living with stylish finishes.This thoughtfully designed home includes two bedrooms and two and a half baths, offering ample space and comfort. The one-car garage adds convenience and practicality to

    Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1532, Chester, MD 21619
  • Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    /24

    $684,900 New Construction

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

    201 Switchgrass Way, Chester, MD 21619

    Gourmet kitchen with wall oven & spacious central island.Dry bar in the dining area adds a stylish touch.Great room features an electric fireplace for cozy evenings.Sliding doors open to a private balcony off the great room.Owner’s suite with direct balcony access for fresh air.Dual vanities in the spa-inspired owner’s bath.Thoughtfully designed layout with

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    Chester, Chester, MD 21619
    /26

    $679,900 New Construction

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

    211 Switchgrass Way, Chester, MD 21619

    Private home office for working or reading.Chef-worthy gourmet kitchen & spacious island perfect for meal prepping.Elegant dining area with convenient dry bar, perfect for entertaining.Open, airy great room with electric fireplace & tray ceiling.Serene owner's suite with crown moulding and balcony access.Glamorous owner's spa bath featuring split vanities.Relaxing

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • Mykonos, Chester, MD 21619
    Mykonos, Chester, MD 21619
    Mykonos, Chester, MD 21619
    /12

    $862,900 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
  • Kerr, Chester, MD 21619
    Kerr, Chester, MD 21619
    Kerr, Chester, MD 21619
    /27

    $797,900 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
  • Jenkins II, Chester, MD 21619
    Jenkins II, Chester, MD 21619
    Jenkins II, Chester, MD 21619
    /25

    $649,900 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
  • Severn, Chester, MD 21619
    Severn, Chester, MD 21619
    Severn, 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
  • Munich ESP, Chester, MD 21619
    Munich ESP, Chester, MD 21619
    Munich ESP, Chester, MD 21619
    /12

    $859,900 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
  • Kelly, Chester, MD 21619
    Kelly, Chester, MD 21619
    Kelly, Chester, MD 21619
    /11

    $752,900 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
  • 137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    /81

    $779,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 2 Baths
    • 2,147 Sq Ft

    137 Warbler Way, Stevensville, MD 21666

    No waiting on the builder here! Treat yourself to this STUNNING move-in-ready Four Seasons beauty- Boasting soaring ceilings, flooded with natural light, spacious, open-floor plan nearly 2200 SF, with generously-sized primary suite & spa-like bath with walk-in-closet, double sinks & walk-in-shower. 2nd bedroom & bath across home offers privacy for guests. Custom barn doors open to bonus space-

    Jennifer Chaney Chaney Homes, LLC

    137 Warbler Way, Stevensville, MD 21666
  • 190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    /32

    $560,000

    • 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 appliances, custom

    Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
  • 2707 Cox Neck Rd, Chester, MD 21619
    2707 Cox Neck Rd, Chester, MD 21619
    2707 Cox Neck Rd, Chester, MD 21619
    /47

    $449,900 Open Sun 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft

    2707 Cox Neck Rd, Chester, MD 21619

    Welcome to Harborview, a long established community on Maryland's eastern shore, home of some of the best seafood on the eastern seaboard! Come see everything that living on "The Shore" has to offer. Fantastic dining on the Kent Narrows, shopping at the outlets, the new pickleball courts in nearby Stevensville and Grasonville, the dog park and of course the new skate park! The Cross Island trail

    Samantha Hernandez Douglas Realty, LLC

    2707 Cox Neck Rd, Chester, MD 21619
  • 35 F Queen Anne Way, Chester, MD 21619
    35 F Queen Anne Way, Chester, MD 21619
    35 F Queen Anne Way, Chester, MD 21619
    /60

    $354,900 Open Sat 12PM - 2PM

    • 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
  • 5C Piney Narrows Rd, Chester, MD 21619
    5C Piney Narrows Rd, Chester, MD 21619
    5C Piney Narrows Rd, Chester, MD 21619
    /22

    $33,000

    • 432 Sq Ft

    5C Piney Narrows Rd, Chester, MD 21619

    Welcome to Piney Narrows Yacht Haven marina condominium in the Kent Narrows, perfect for active boaters who want a comfortable, convenient community-oriented home port, now available is COVERED SLIP C-5!! (36' X 14' with 2 -30 amp power and water hook up) Entertain family and friends in the luxury of your own covered slip. Yacht Haven amenities include access to community swimming pool, picnic

    Kaitlyn Collins Benson & Mangold, LLC

    5C Piney Narrows Rd, Chester, MD 21619
  • 24 D Queen Elizabeth Ct, Chester, MD 21619
    24 D Queen Elizabeth Ct, Chester, MD 21619
    24 D Queen Elizabeth Ct, Chester, MD 21619
    /74

    $549,000

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

    24 D Queen Elizabeth Ct, Chester, MD 21619

    Welcome to 24D Queen Elizabeth Ct, a beautifully updated 2-bedroom waterfront condo with a spacious loft that easily serves as a third bedroom, office, or bonus space. Nestled in the highly desirable Queens Landing community, this home offers spectacular front and back water views — enjoy both peaceful sunrises and vibrant sunsets every day.Inside, the open-concept layout is flooded with natural

    The Williams Home Team JPAR Maryland Living

    24 D Queen Elizabeth Ct, Chester, MD 21619
  • 413 Dominion Rd, Chester, MD 21619
    413 Dominion Rd, Chester, MD 21619
    413 Dominion Rd, Chester, MD 21619
    /30

    $399,000

    • 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
  • 1838 Sherman Dr, Chester, MD 21619
    1838 Sherman Dr, Chester, MD 21619
    1838 Sherman Dr, Chester, MD 21619
    /23

    $396,000

    • 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
  • 15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    /68

    $549,000

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

    15 Queen Anne Way Unit E, Chester, MD 21619

    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 flooring, and access to a private patio where peaceful morning

    Julia Stevens Realty Navigator

    15 Queen Anne Way Unit E, Chester, MD 21619
  • 28E Queen Mary Ct, Chester, MD 21619
    28E Queen Mary Ct, Chester, MD 21619
    28E Queen Mary Ct, Chester, MD 21619
    /26

    $365,000

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

    28E Queen Mary Ct, Chester, MD 21619

    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 views from one side and the vibrant energy of the tennis and pickleball courts on the other.Tucked away on

    Justin Disborough Samson Properties

    28E Queen Mary Ct, Chester, MD 21619
  • 513 Teal Ct, Chester, MD 21619
    513 Teal Ct, Chester, MD 21619
    513 Teal Ct, Chester, MD 21619
    /44

    $295,000

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

    513 Teal Ct, Chester, MD 21619

    *Experience a getaway lifestyle at this stunning 2nd-floor condominium nestled within the prestigious Bayside Condominium Community. Enjoy peaceful views of the pond and fountain from the private balcony. You will delight in the pond views from the living room, dining and kitchen. The spacious living room features built-ins and seamlessly transitions into the dining area, complete with a sliding

    April Heim Rosendale Realty

    513 Teal Ct, Chester, MD 21619
  • 1809 Stevens Dr, Chester, MD 21619
    1809 Stevens Dr, Chester, MD 21619
    1809 Stevens Dr, Chester, MD 21619
    /33

    $439,000

    • 4 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    1809 Stevens Dr, Chester, MD 21619

    Best deal on Kent Island! Beautiful 4 Bedroom 2 1/2 bath Cape on over 1/2 acre in peaceful Harbor View. Airy and spacious, this terrific home boasts 2 Bedrooms plus Full bath on the Main level with all new hardwood flooring and separate light -filled and cozy living and dining spaces. The gorgeous just updated kitchen features fabulous quartz countertops, all modern stainless steel appliances,

    Greg Koch Taylor Properties

    1809 Stevens Dr, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 3

Maryland Chester

Real Estate & Homes for Sale in Chester, MD

Why Live in Chester

Sandwiched between the Chester River and Chesapeake Bay in the heart of Kent Island, the Chester area comprises residential suburbs with close proximity to Highway 50. “It is known for its maritime feel—endless views of water, marinas and local establishments, lining the shoreline,” says Jennifer Heilman, the marketing manager for K. Hovnanian Homes. The area also sits 17 miles from Annapolis, Maryland’s capital city and the home of the United States Naval Academy. With access to both nature and modern conveniences, Chester caters to the laid-b ...

Learn more about living in Chester

Frequently Asked Questions

What is the average home price in Chester, MD?
Homes for sale in Chester, MD have an average home price of $590,424.
How many homes have sold over the last 12 months in Chester, MD?
166 homes have sold in Chester, MD over the last 12 months.
Is Chester, MD a safe city?
In general, the safest neighborhood in Chester, MD with lower crime scores is Kent Narrows.
What are the most popular zip codes in Chester, MD?
The most popular zip codes in Chester, MD include 21122, 21403, 21060, 21401 and 21601.
What are the most popular neighborhoods in Chester, MD?
The most popular neighborhood in Chester, MD with the most homes for sale is Kent Narrows.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $565,000. If you put a 20% down payment of $113,000 and had a 30-year fixed mortgage with an interest rate of 6.85%, your estimated principal and interest payment would be $2,960 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $127K a year to afford the median home price in Chester.
How are the schools in Chester, MD?
Chester, MD has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Bayside Elementary School, Matapeake Middle School and Stevensville Middle School. The neighborhood in Chester with the highest rated schools is Kent Narrows. Browse all the schools in Chester, MD to learn more.

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 48 days on the market compared to the national average of 49 days. The median sale price for homes in Chester, MD over the last 12 months is $588,750, up 16% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$588,750
Median Single Family Sale Price
$616,900
Median Townhouse Sale Price
$381,000
Median 2 Bedroom Sale Price
$525,000
Median 1 Bedroom Sale Price
$296,500
Average Price Per Sq Ft
$296
Number of Homes for Sale
71
Last 12 months Home Sales
166
Months of Supply
5.10
Median List Price
$565,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
16%
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