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Chester, MD Houses for Sale

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  • 330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    /55

    $1,050,000 Coming Soon

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

    330 Macum Creek Dr, Chester, MD 21619

    COMING SOON IN GIBSON'S GRANT! Move in ready with custom upgrades throughout, 330 Macum Creek Drive offers luxury living in one of Kent Island’s most sought after communities. A few highlights of the property include a main level primary with custom closets, finished room over the garage with a full bathroom, open concept kitchen and living space, custom butler's pantry, bonus living space with

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 256-7961

    330 Macum Creek Dr, Chester, MD 21619
  • Mykonos, Chester, MD 21619
    Mykonos, Chester, MD 21619
    Mykonos, 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
  • Kerr, Chester, MD 21619
    Kerr, Chester, MD 21619
    Kerr, Chester, MD 21619
    /27

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

    $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
  • Taylor, Chester, MD 21619
    Taylor, Chester, MD 21619
    Taylor, 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
  • Franklin, Chester, MD 21619
    Franklin, Chester, MD 21619
    Franklin, 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
  • Tuscaloosa, Chester, MD 21619
    Tuscaloosa, Chester, MD 21619
    Tuscaloosa, Chester, MD 21619
    /42

    $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
  • 224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    /48

    $619,900 Open Sat 11AM - 1PM

    • 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
  • 129 Kirwans Landing Ln, Chester, MD 21619
    129 Kirwans Landing Ln, Chester, MD 21619
    129 Kirwans Landing Ln, Chester, MD 21619
    /61

    $997,000

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

    $1,299,900

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

    1622 Bayside Dr, Chester, MD 21619

    Just what you’ve been searching for in this perfect home that meets all your desires! Perfect unobstructed sunsets, master suite on the main to enjoy the perfect unobstructed sunsets, and the second highest lot in Marling Farms (12 feet above sea level) so no flood insurance needed! Heavenly!!!!Experience the pinnacle of waterfront living in this beautifully crafted Eastern Shore residence. Every

    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

    $649,400

    • 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
  • 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
    • 2,602 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
  • 132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    132 Claiborne St, 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
  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, 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 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

    • 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
  • 164 Redstart Dr, Chester, MD 21619
    164 Redstart Dr, Chester, MD 21619
    164 Redstart Dr, Chester, MD 21619
    /57

    $889,900 New Construction

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

    164 Redstart Dr, Chester, MD 21619

    Discover the charm and versatility of the Kerr, a thoughtfully designed 3-bedroom, 3-bath home offering an open layout, high-end finishes, and spaces tailored for comfort. With a 3-car garage and flexible rooms throughout, this home adapts beautifully to everyday living or entertaining.The main level features durable Luxury Vinyl Plank flooring, a warm fireplace, and a screened patio for

    Mary Anne Kowalewski KOVO Realty

    164 Redstart Dr, Chester, MD 21619
  • 327 Kingfisher Ln, Chester, MD 21619
    327 Kingfisher Ln, Chester, MD 21619
    327 Kingfisher Ln, Chester, MD 21619
    /45

    $999,900 New Construction

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

    327 Kingfisher Ln, Chester, MD 21619

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

    Mary Anne Kowalewski KOVO Realty

    327 Kingfisher Ln, Chester, MD 21619
  • 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
  • 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
  • Munich ESP, Chester, MD 21619
    Munich ESP, Chester, MD 21619
    Munich ESP, 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
  • Kelly, Chester, MD 21619
    Kelly, Chester, MD 21619
    Kelly, 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
  • Simone, Chester, MD 21619
    Simone, Chester, MD 21619
    Simone, Chester, MD 21619
    /14

    $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
  • Bernstein II, Chester, MD 21619
    Bernstein II, Chester, MD 21619
    Bernstein II, 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
  • 1501 Norman Rd, Chester, MD 21619
    1501 Norman Rd, Chester, MD 21619
    1501 Norman Rd, 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
  • 137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    137 Warbler Way, Stevensville, MD 21666
    /81

    $739,950 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
  • 2723 Cox Neck Rd, Chester, MD 21619
    2723 Cox Neck Rd, Chester, MD 21619
    2723 Cox Neck Rd, 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
  • 1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, 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
  • 1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    1906 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
  • 412 Hanna Ct, Chester, MD 21619
    412 Hanna Ct, Chester, MD 21619
    412 Hanna Ct, Chester, MD 21619
    /51

    $485,000

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

    412 Hanna Ct, Chester, MD 21619

    Welcome to 412 Hanna Court, Chester, MD – DID YOU KNOW THIS HOME HAS AN 2.75% ASSUMABLE VA MORTGAGE of $294K!!! Nestled at the end of a quiet cul-de-sac in the highly sought-after Claybourne Woods community, this beautifully maintained 4-bedroom, 2.5-bath home blends modern upgrades with everyday comfort in an ideal Eastern Shore location. Enjoy a quick 30-minute commute to Downtown

    Sarah Miller Hubble Bisbee Christie's International Real Estate

    412 Hanna Ct, 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

    $434,900

    • 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
  • 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
    /22

    $393,000

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    1838 Sherman Dr, Chester, MD 21619

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

    Kara Shaffer Engel & Völkers Annapolis

    1838 Sherman Dr, Chester, MD 21619
  • 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

    OPEN HOUSE, Saturday, June 21, 11 am - 1 pm...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 lower-level family

    Darlene Winegardner RE/MAX Executive

    205 Anchor Ln, 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

    • 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
  • 558 Cross Creek Ct, Chester, MD 21619
    558 Cross Creek Ct, Chester, MD 21619
    558 Cross Creek Ct, Chester, MD 21619
    /29

    $559,850

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

    558 Cross Creek Ct, Chester, MD 21619

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

    Thomas Hennerty NetRealtyNow.com, LLC

    558 Cross Creek Ct, Chester, MD 21619
  • 1019 Dominion Rd, Chester, MD 21619
    1019 Dominion Rd, Chester, MD 21619
    1019 Dominion Rd, Chester, MD 21619
    /45

    $369,000

    • 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

    $389,000

    • 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

    BJ Kilby EXIT On The Bay

    2653 Cox Neck Rd, 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

Chester features a diverse housing market with single-family homes, condos, and townhouses. The neighborhood includes ranch-style homes, colonials, and New Traditional builds. Properties south of Highway 50 date back to the mid-to-late 20th century, while newer communities in the northern sector have been developed over the past decade. Chester's parks and recreational activities are abundant, with Terrapin Nature Park offering walking paths and Chesapeake Bay views, and the Cross Island Trail providing a paved walkway for hikers and cyclists. Castle Marina is a hub for boating activities, and Club One Fitness and Aerobics offers gym facilities and an aquatic center. Shopping and dining are concentrated in plazas off Highway 50, with big-box stores like Safeway, Walgreens, and Target, and a variety of restaurants ranging from fast food to local favorites. Notable dining spots include The Jetty, Bridges, and Fisherman’s Inn in nearby Kent Narrows. Annual events such as the Kent Island Day parade and the Annapolis Baygrass Music Festival bring the community together. Highway 50 is the main thoroughfare, connecting Chester to Annapolis, 17 miles away, and the Chesapeake Bay Bridge provides access to Baltimore and Washington, D.C. Public transportation is available via Queen Anne’s County buses, and BWI International Airport is about 30 miles away. Schools in Chester are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving strong ratings.
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 50 days. The median sale price for homes in Chester, MD over the last 12 months is $575,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$575,000
Median Single Family Sale Price
$630,900
Median Townhouse Sale Price
$390,500
Median 2 Bedroom Sale Price
$499,000
Median 1 Bedroom Sale Price
$293,000
Average Price Per Sq Ft
$294
Number of Homes for Sale
77
Last 12 months Home Sales
173
Months of Supply
5.30
Median List Price
$569,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 46 houses for sale, offering an array of options for potential buyers. With houses priced between $49,000 to $1,950,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Chester is $569,000, while the average sale price is $590,679, 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.

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