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Chester, MD Houses for Sale

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  • 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
  • 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
  • 1622 Bayside Dr, Chester, MD 21619
    1622 Bayside Dr, Chester, MD 21619
    1622 Bayside Dr, Chester, MD 21619
    /68

    $1,374,900

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    1622 Bayside Dr, Chester, MD 21619

    Eastern Shore Luxury with Sweeping Bay ViewsEvery room tells a story in this impeccably crafted waterfront residence, where panoramic bay views take center stage and luxury lives in the details. Thoughtfully designed with a custom floorplan and built to the highest standards, this home feels like new — a true showcase of elegance, comfort, and craftsmanship.Step into a bright and airy

    Cynthia Sullivan Sullivan Select, LLC.

    1622 Bayside Dr, Chester, MD 21619
  • 154 Harrier Way, Chester, MD 21619
    154 Harrier Way, Chester, MD 21619
    154 Harrier Way, Chester, MD 21619
    /45

    $649,500 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
  • 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
  • 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
  • Taylor, Chester, MD 21619
    Taylor, Chester, MD 21619
    Taylor, Chester, MD 21619
    /10

    $730,900 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
  • Simone, Chester, MD 21619
    Simone, Chester, MD 21619
    Simone, Chester, MD 21619
    /14

    $681,900 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
  • Bernstein II, Chester, MD 21619
    Bernstein II, Chester, MD 21619
    Bernstein II, Chester, MD 21619
    /12

    $616,900 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
  • Franklin, Chester, MD 21619
    Franklin, Chester, MD 21619
    Franklin, Chester, MD 21619
    /27

    $834,900 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
  • Tuscaloosa, Chester, MD 21619
    Tuscaloosa, Chester, MD 21619
    Tuscaloosa, Chester, MD 21619
    /42

    $826,900 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
  • 137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    /81

    $779,000 New Construction

    • 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
  • 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
  • 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
  • 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
  • 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

    The one you've been waiting for! 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

    Greg Koch Taylor Properties

    1809 Stevens Dr, Chester, MD 21619
  • 326 Hanna Ct, Chester, MD 21619
    326 Hanna Ct, Chester, MD 21619
    326 Hanna 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
  • 307 Skipper Ln, Chester, MD 21619
    307 Skipper Ln, Chester, MD 21619
    307 Skipper Ln, Chester, MD 21619
    /31

    $525,000 Open Sat 12PM - 2PM

    • 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
  • 203 Anchor Ln, Chester, MD 21619
    203 Anchor Ln, Chester, MD 21619
    203 Anchor Ln, Chester, MD 21619
    /26

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft

    203 Anchor Ln, Chester, MD 21619

    Think you've seen this one before? WE INVITE YOU TO TAKE A 2nd LOOK!! Staged and re-freshed you'll wonder why you didn't scoop this one up earlier! This adorable rancher has the traditional 3 bedrooms and 2 baths and so much more including a large dining area, kitchen with breakfast bar that flows into a large living room anchored by a beautiful brick fireplace. PLUS a large addition offers a

    Tricia Wilson Wilson Realty & Staging LLC

    203 Anchor Ln, Chester, MD 21619
  • 1903 Churchhill Ln, Chester, MD 21619
    1903 Churchhill Ln, Chester, MD 21619
    1903 Churchhill Ln, Chester, MD 21619
    /12

    $334,900

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

    1903 Churchhill Ln, Chester, MD 21619

    Welcome to 1903 Churchill Lane, Chester, MD 21619!This spacious 4-bedroom, 3-bath home is full of potential and located in one of Kent Island’s most sought-after neighborhoods. Offering a generous floor plan, this property is ideal for buyers looking to customize and renovate to their personal taste.The home features owned solar panels with a remaining balance—an energy-efficient investment that

    DANIEL DEMERS Sell Your Home Services

    1903 Churchhill Ln, Chester, MD 21619
  • 2008 Palm Dr, Chester, MD 21619
    2008 Palm Dr, Chester, MD 21619
    2008 Palm Dr, Chester, MD 21619
    /51

    $500,000

    • 3 Beds
    • 2.5 Baths
    • 2,283 Sq Ft

    2008 Palm Dr, Chester, MD 21619

    New Price Improvement! Cape Cod with spacious wrap around porch! Upon entering, you will be greeted with hardwood floors throughout most of the main level. The focal point once inside is the beautiful open family room with a wood burning fireplace with stacked stone soaring to the vaulted ceiling and two ceiling fans when cooling off in the warmer months! The gourmet kitchen opens up into the

    Marilyn Hendley EXP Realty, LLC

    2008 Palm Dr, Chester, MD 21619
  • 1019 Dominion Rd, Chester, MD 21619
    1019 Dominion Rd, Chester, MD 21619
    1019 Dominion Rd, Chester, MD 21619
    /45

    $429,000

    • 1 Bed
    • 1 Bath
    • 1,008 Sq Ft

    1019 Dominion Rd, Chester, MD 21619

    Waterfront Opportunity Awaits on Kirwans Creek! Imagine the possibilities! This charming cape cod home offers an incredible chance to create your own waterfront retreat on the Kirwans Creek. Situated on a desirable lot with direct water access, this property boasts a comfortable main level and an expansive, unfinished second floor brimming with potential. The main level welcomes you with a

    Lisa Lynch Keller Williams Realty

    1019 Dominion Rd, Chester, MD 21619
  • 2653 Cox Neck Rd, Chester, MD 21619
    2653 Cox Neck Rd, Chester, MD 21619
    2653 Cox Neck Rd, Chester, MD 21619
    /24

    $419,000

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    2653 Cox Neck Rd, Chester, MD 21619

    Welcome to 2653 Cox Neck Rd—a beautifully renovated rancher nestled in the heart of Kent Island. This charming 3-bedroom, 2-bathroom home offers the ease of single-level living with modern updates throughout. Sitting on a spacious 0.36-acre lot, the property combines comfort, style, and a touch of coastal serenity.Step inside to discover a layout with contemporary finishes, updated flooring,

    BJ Kilby EXIT On The Bay

    2653 Cox Neck Rd, Chester, MD 21619
  • 312 Hanna Ct, Chester, MD 21619
    312 Hanna Ct, Chester, MD 21619
    312 Hanna Ct, Chester, MD 21619
    /45

    $485,000

    • 4 Beds
    • 2.5 Baths
    • 2,228 Sq Ft

    312 Hanna Ct, Chester, MD 21619

    ** This home is connected to public water and sewer.Welcome to 312 Hanna Ct, a beautifully updated 4-bedroom, 2.5-bath single-family home in Chester, MD! This home boasts numerous upgrades, including a newer roof with 50-year architectural shingles and a transferable warranty, a new furnace, and new LVP flooring on the first level, with new carpet upstairs.The kitchen was updated in 2021 with

    Bob Chew Berkshire Hathaway HomeServices PenFed Realty

    312 Hanna Ct, Chester, MD 21619
  • 5H Piney Narrows Rd, Chester, MD 21619
    5H Piney Narrows Rd, Chester, MD 21619
    5H Piney Narrows Rd, 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

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Maryland Chester

Houses 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

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 49 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 $590,000, up 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$590,000
Median Single Family Sale Price
$618,450
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
72
Last 12 months Home Sales
170
Months of Supply
5.10
Median List Price
$569,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
12%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 44 houses for sale, offering an array of options for potential buyers. With houses priced between $33,000 to $1,950,000, there's a range to accomodate every budget. As of June, 2025 the median home price in Chester is $569,900, while the average sale price is $611,636, offering insights into the local housing market. On average, houses spend 49 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Chester, MD and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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