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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

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

    330 Macum Creek Dr, Chester, MD 21619

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

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 256-7961

    330 Macum Creek Dr, Chester, MD 21619
  • 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
    /26

    $807,900 New Construction

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

    Kerr, Chester, MD 21619

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

    K Hovnanian's Four Seasons

    Kerr, Chester, MD 21619
  • Jenkins II, Chester, MD 21619
    Jenkins II, Chester, MD 21619
    Jenkins II, Chester, MD 21619
    /24

    $659,900 New Construction

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

    Jenkins II, Chester, MD 21619

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

    K Hovnanian's Four Seasons

    Jenkins II, Chester, MD 21619
  • 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
    /40

    $836,900 New Construction

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

    Tuscaloosa, Chester, MD 21619

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

    K Hovnanian's Four Seasons

    Tuscaloosa, Chester, MD 21619
  • 121 John Gibson Dr, Chester, MD 21619
    121 John Gibson Dr, Chester, MD 21619
    121 John Gibson Dr, Chester, MD 21619
    /49

    $825,000

    • 4 Beds
    • 2.5 Baths
    • 2,760 Sq Ft

    121 John Gibson Dr, Chester, MD 21619

    Welcome home to 121 John Gibson Drive in the waterfront community of Gibson's Grant on Kent Island. This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of charm, functionality, and comfort. Step inside to discover a bright and open floor plan featuring a cozy gas fireplace, ideal for relaxing evenings or entertaining guests. The heart of the home is the gorgeous offering

    Tara Trout Keller Williams Flagship

    121 John Gibson Dr, Chester, MD 21619
  • 255 Sailcloth Way, Chester, MD 21619
    255 Sailcloth Way, Chester, MD 21619
    255 Sailcloth Way, Chester, MD 21619
    /56

    $950,000

    • 4 Beds
    • 4 Baths
    • 3,450 Sq Ft

    255 Sailcloth Way, Chester, MD 21619

    Welcome to 255 Sailcloth Way in Chester’s premier 55+ community—K. Hovnanian’s Four Seasons at Kent Island. This upgraded Santorini model is perfectly situated on a cul-de-sac premium lot and features 4 bedrooms, 4 full baths, and double primary suites—ideal for multigenerational living or hosting guests in comfort. Enjoy high-end finishes throughout, including LVP flooring, a chef’s kitchen with

    Kathleen Higginbotham Keller Williams Flagship

    255 Sailcloth Way, Chester, MD 21619
  • 162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    /37

    $1,195,000

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

    162 Kirwans Landing Ln, Chester, MD 21619

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

    Brad Kappel TTR Sotheby's International Realty

    162 Kirwans Landing Ln, Chester, MD 21619
  • 204 Skipper Ln, Chester, MD 21619
    204 Skipper Ln, Chester, MD 21619
    204 Skipper Ln, Chester, MD 21619
    /106

    $650,000

    • 6 Beds
    • 3 Baths
    • 3,760 Sq Ft

    204 Skipper Ln, Chester, MD 21619

    Welcome home to spacious comfort and thoughtful design in this inviting six-bedroom, three-bath residence nestled on a quiet lane in Chester. With over 3,700 square feet of interior living space, there’s room here for everyone—and maybe even that home office or gym you’ve been dreaming about.Step inside to find an updated kitchen ready for your culinary adventures, featuring modern

    Andy Schweigman Douglas Realty, LLC

    204 Skipper Ln, Chester, MD 21619
  • 224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    /47

    $619,900

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

    224 Bayberry Dr, Chester, MD 21619

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

    Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
  • 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

    $639,500

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

    154 Harrier Way, Chester, MD 21619

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

    Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
  • 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 Eastern Shore Real Estate, LLC

    1868 Roberta Dr, Chester, MD 21619
  • 2817 Cox Neck Rd, Chester, MD 21619
    2817 Cox Neck Rd, Chester, MD 21619
    2817 Cox Neck Rd, Chester, MD 21619
    /35

    $2,050,000

    • 6 Beds
    • 5.5 Baths
    • 5,174 Sq Ft

    2817 Cox Neck Rd, Chester, MD 21619

    This stunning waterfront, custom built home sits ideally on a little over an acre fronting Crab Alley Bay in the prestigious Southwind community. Home boast almost 10,000 square feet, between finished living space and additional expansion space. An already large home offers so much more room to grow the perfect, waterfront retreat. This gem features 6 large bedrooms and of those 4 have private

    Michael Bozek Michael J. Bozek

    2817 Cox Neck Rd, Chester, MD 21619
  • 509 Warbler Way, Chester, MD 21666
    509 Warbler Way, Chester, MD 21666
    509 Warbler Way, Chester, MD 21666
    /50

    $714,900 New Construction

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

    509 Warbler Way, Chester, MD 21666

    Settle into style with the Jenkins, a 2-bedroom, 2-bath home that balances cozy charm with functional upgrades. A 2-car garage, dedicated home office, and a screened patio offer flexibility and space for everyday living and entertaining.The heart of the home includes a stone fireplace and a thoughtfully designed kitchen featuring a single oven, gas cooktop, range hood, French door

    Mary Anne Kowalewski KOVO Realty

    509 Warbler Way, Chester, MD 21666
  • 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
  • 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
    /13

    $691,900 New Construction

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

    Simone, Chester, MD 21619

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

    K Hovnanian's Four Seasons

    Simone, Chester, MD 21619
  • 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
  • 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
  • 203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    /53

    $515,000

    • 3 Beds
    • 1.5 Baths
    • 2,072 Sq Ft

    203 Barren Ridge Rd, Chester, MD 21619

    Nestled in the tranquil community of Chester, Maryland, 203 Barren Ridge Road offers a unique blend of coastal charm and suburban comfort. This inviting Colonial-style home, situated on a 0.31-acre lot, features three bedrooms and one and a half bathrooms, providing ample space for living and entertaining both in and outdoors. With a spacious living room, a cozy family room, and a beautifully

    Beth Bearinger Keller Williams Gateway LLC

    203 Barren Ridge Rd, Chester, MD 21619
  • 315 Cross Creek Ct, Chester, MD 21619
    315 Cross Creek Ct, Chester, MD 21619
    315 Cross Creek Ct, Chester, MD 21619
    /43

    $585,000

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

    315 Cross Creek Ct, Chester, MD 21619

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

    Jimmy White Long & Foster Real Estate, Inc.

    315 Cross Creek Ct, Chester, MD 21619
  • 1405 Little Creek Rd, Chester, MD 21619
    1405 Little Creek Rd, Chester, MD 21619
    /2

    $19,500

    • 2 Beds
    • 1 Bath
    • 764 Sq Ft

    1405 Little Creek Rd, Chester, MD 21619

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

    Dustin Parker The Parker Group

    1405 Little Creek Rd, Chester, MD 21619
  • 2723 Cox Neck Rd, Chester, MD 21619
    2723 Cox Neck Rd, Chester, MD 21619
    2723 Cox Neck Rd, Chester, MD 21619
    /41

    $479,900

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

    2723 Cox Neck Rd, Chester, MD 21619

    Harbor View - 100% Financing is Available!!! PLUS - Seller is offering a 1 Point Rate Buy Down for an acceptable contract received by July 31th! This newly constructed home features 4 bedrooms and 2.5 baths. Offering a first-floor bedroom or this would be a great office as well. Inside, enjoy the warmth of upgraded LYP floors that flow seamlessly throughout the first floor living spaces and

    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

    1872 Harbor Drive, Chester, MD in the Sought-After Harbor View CommunityPremium Corner Lot | Nearly 3⁄4 Acre | Renovated Brick RancherLocated in the established Harbor View neighborhood, this fully renovated brick rancher sits on a rare, oversized corner lot—nearly three-quarters of an acre made up of two parcels. The expanded lot offers flexibility for future additions, such as an

    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
  • 413 Dominion Rd, Chester, MD 21619
    413 Dominion Rd, Chester, MD 21619
    413 Dominion Rd, Chester, MD 21619
    /30

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft

    413 Dominion Rd, Chester, MD 21619

    KENT ISLAND *Single Family Home * 3 bedrooms, 2 full bathrooms * Main level has a spacious eat in kitchen with french doors leading to the backyard deck, family room with lots of natural light and brand new full bathroom with newer LG front loading washer and dryer * There are 3 bedrooms and a full bathroom with tub/shower upstairs *Heat pump system with central AC* Many upgrades through out the

    Suzanne Hitt Coldwell Banker Waterman Realty

    413 Dominion Rd, Chester, MD 21619
  • 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

    $566,000

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

    205 Anchor Ln, Chester, MD 21619

    Price Improvement! Need more room? This expansive home is ready to welcome your whole family! With 5 bedrooms, 3 full bathrooms and an over-sized 4-car garage, there's plenty of space for everyone to spread out and enjoy their own privacy.You'll be delighted by a mix of formal and casual living spaces, including a bright formal living room, a cozy lower-level family room, and a huge

    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
  • 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
  • 308 Dominion Rd, Chester, MD 21619
    308 Dominion Rd, Chester, MD 21619
    308 Dominion Rd, Chester, MD 21619
    /35

    $334,900

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

    308 Dominion Rd, Chester, MD 21619

    Charming Rancher in Chester, MD - Welcome to 308 Dominion Rd, a beautifully updated 3-bedroom, 2-bathroom rancher offering 1,280 sq. ft. of comfortable living space. Situated on a spacious 0.31-acre lot, this home features brand-new luxury vinyl plank flooring throughout the main areas, plush carpeting in the bedrooms, and a newly installed HVAC system for year-round comfort. The generously sized

    Tyler Burch Burch Real Estate Group, LLC

    308 Dominion Rd, Chester, MD 21619

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Houses for Sale in Chester, MD

Why Live in Chester

Chester, MD, located on Kent Island between the Chester River and Chesapeake Bay, offers a blend of coastal charm and modern convenience. The area is known for its maritime atmosphere, with numerous marinas and waterfront views. Chester is 17 miles from Annapolis, home to the United States Naval Academy. Outdoor enthusiasts can enjoy Terrapin Nature Park's walking paths and tidal marshes, or the Cross Island Trail for hiking and cycling. Castle Marina provides opportunities for boating and fishing. Indoor fitness options include Club One Fitness and Aerobics. Housing in Chester ranges from ranch-style homes and colonials to New Traditional builds, with properties south of Highway 50 dating back to the mid-20th century and newer developments in the north. The area features a mix of single-family homes, condos, and townhouses, with some waterfront estates requiring additional flood insurance. Annual events like the Kent Island Crab Feast and the Annapolis Baygrass Music Festival foster community spirit. Shopping and dining are centered around Highway 50, with big-box stores like Safeway and Target, and bayside dining options in nearby Kent Narrows, including The Jetty and Bridges. Chester's schools are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving commendable scores. Highway 50 is the main transportation route, connecting Chester to Annapolis, Baltimore, and Washington, D.C., while BWI International Airport is about 30 miles away.
Learn more about living in Chester

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 45 days on the market compared to the national average of 70 days. The median sale price for homes in Chester, MD over the last 12 months is $649,900, down 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$649,900
Median Single Family Sale Price
$685,450
Median Townhouse Sale Price
$469,000
Median 2 Bedroom Sale Price
$540,000
Average Price Per Sq Ft
$347
Number of Homes for Sale
17
Last 12 months Home Sales
122
Months of Supply
1.70
Median List Price
$649,900
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 46 houses for sale, offering an array of options for potential buyers. With houses priced between $19,500 to $2,050,000, there's a range to accomodate every budget. As of July, 2025 the median home price in Chester is $649,900, while the average sale price is $605,859, offering insights into the local housing market. On average, houses spend 45 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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