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Chester, MD Houses for Sale

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  • /30

    $465,000

    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft

    1713 Bayside Dr, Chester, MD 21619

    PRICE IMPROVEMENT! The perfect opportunity to customize your dream home with water views in the coveted Marling Farms community!Seated across from Crab Alley Bay, this rancher style home is ready for it's next owners to make it their own. With two spacious living areas, water views from the whole front of the house, a primary suite with huge walk in closet, three full bathrooms, a sunroom

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 247-8740

    1713 Bayside Dr, Chester, MD 21619
  • /42

    $679,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,134 Sq Ft

    194 Evelyne St, Chester, MD 21619

    Welcome to 194 Evelyne Street, located in the sought-after waterfront community of Gibson's Grant! Get ready to embrace the laid-back, coastal lifestyle you’ve always dreamed of—right from the comfort of home. If you've been searching for the ease and comfort of one-level living, your search ends here!This beautifully crafted Stanford model by Koch Homes offers just over 2,000 square feet of

    Tara Trout Keller Williams Flagship

    194 Evelyne St, Chester, MD 21619
  • /61

    $850,000

    • 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
  • /70

    $929,500

    • 3 Beds
    • 3.5 Baths
    • 3,514 Sq Ft

    235 Bayberry Dr, Chester, MD 21619

    Experience Kent Island living at its finest in this upgraded luxurious San Sebastian model in the prestigious Four Seasons community. Featuring an open floor plan with 10’ ceilings, designer finishes, newly renovated enclosed four-season porch and patio overlooking a gorgeous premium lot, this residence provides an ideal setting for both entertaining and everyday comfort. Arriving home, manicured

    Ralph Kennedy RE/MAX Executive

    235 Bayberry Dr, Chester, MD 21619
  • /28

    $850,000

    • 3 Beds
    • 2.5 Baths
    • 1,588 Sq Ft

    120 Hopkins Rd, Chester, MD 21619

    Imagine waking up to the tranquil sounds of nature and being surrounded by breathtaking waterfront views every day. This spacious Cape Cod property offers the perfect balance of privacy and beauty, nestled between serene marshlands and towering trees. Enjoy your evenings watching stunning sunsets through expansive waterside windows and doors that bring the outdoors in.Inside, you'll find an

    Lisa Barton Coldwell Banker Realty

    120 Hopkins Rd, Chester, MD 21619
  • /45

    $655,000

    • 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
  • /62

    $799,000

    • 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
  • /67

    $1,250,000

    • 4 Beds
    • 3 Baths
    • 2,876 Sq Ft

    1360 Calvert Rd, Chester, MD 21619

    Exceptional Waterfront Home with Spectacular Views.This beautiful waterfront home offers the perfect blend of elegance, comfort, and breathtaking scenery. Nestled among mature shade trees, it provides stunning water views, refreshing summer breezes, and unforgettable sunsets. Designed for both relaxation and entertaining, this home is an ideal retreat for creating lasting memories with family

    Alex Hodges Cottage Street Realty LLC

    1360 Calvert Rd, Chester, MD 21619
  • /29

    $789,000 Open Sun 12PM - 3PM

    • 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
  • /49

    $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 glass doors, provides stunning views of the water, while the family room features a cozy fireplace. A separate formal living

    Dee Dee McCracken Coldwell Banker Realty

    1771 Harbor Dr, 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
  • /54

    $654,900 New Construction

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

    241 Warbler Way, Chester, MD 21619

    Jenkins Home Design - Projected Settlement Date: June 2025Welcome to the Jenkins, a beautifully designed home located on Lot 374, offering both comfort and style in a thoughtfully planned layout. This home features 2 bedrooms, 2 full bathrooms, and a 2-car garage, making it perfect for easy living with modern flair.Highlights Include:Dedicated Home Office – ideal for remote work or a quiet

    Mary Anne Kowalewski KOVO Realty

    241 Warbler Way, Chester, MD 21619
  • /42

    $719,900 New Construction

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

    510 Warbler Way, Chester, MD 21619

    Introducing the Simone – Where Modern Comfort Meets Farmhouse CharmProjected for settlement on July 2025, the Simone home design 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

    Mary Anne Kowalewski KOVO Realty

    510 Warbler Way, Chester, MD 21619
  • /12

    $852,900 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
  • /27

    $787,900 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
  • /25

    $629,900 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
  • /12

    $849,900 New Construction

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

    Munich-ESP, Chester, MD 21619

    Extra Suite Plus for multi-generational living. Striking kitchen with large center island and corner pantry. Spacious great room with tons of windows for natural sun light. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities and optional freestanding tub. Private home office off foyer for working from home.

    K Hovnanian's Four Seasons

    Munich-ESP, Chester, MD 21619
  • /11

    $742,900 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
  • /10

    $720,900 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
  • /14

    $661,900 New Construction

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

    Simone, Chester, MD 21619

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

    K Hovnanian's Four Seasons

    Simone, Chester, MD 21619
  • /12

    $596,900 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
  • /27

    $824,900 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
  • /34

    $671,400 Open Sun 11AM - 2PM

    • 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
  • /2

    $670,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,551 Sq Ft

    106 Woods Rd, Chester, MD 21619

    Coming Soon!

    Jackie Ball Daley Northrop Realty

    106 Woods Rd, Chester, MD 21619
  • /81

    $799,000 Open House 5/10

    • 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
  • /51

    $525,000

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

    2008 Palm Dr, Chester, MD 21619

    You’ve been waiting for this!! Beautiful 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

    Marilyn Hendley EXP Realty, LLC

    2008 Palm Dr, Chester, MD 21619
  • /45

    $449,000

    • 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
  • /35

    $475,000

    • 3 Beds
    • 1 Bath
    • 1,428 Sq Ft

    1017 Dominion Rd, Chester, MD 21619

    This delightful brick home offers the perfect blend of comfortable living and direct access to the beautiful waters of Kirwan Creek. This home features three bedrooms, one bathroom, family room, kitchen and dining room. Enjoy picturesque nature views and water views from your backyard patio. Boaters will appreciate the large, fixed dock as well as the floating docks which are prefect for

    Lisa Lynch Keller Williams Realty

    1017 Dominion Rd, Chester, MD 21619
  • /37

    $535,000

    • 4 Beds
    • 2.5 Baths
    • 2,106 Sq Ft

    327 Cross Creek Ct, Chester, MD 21619

    JUST LISTED & OPEN Sat, 4/26, 1pm-3pm. Do not miss! Clayborne Woods is a private community with one way in and one way out! Neighbors describe it as close knit, friendly, and a place they do not want to leave! This home sits on a prime lot in the neighborhood, with wooded views from almost every side, affording you the Eastern Shore serene living you come here to get! As you enter this home,

    Violeta Aguirre Long & Foster Real Estate, Inc.

    327 Cross Creek Ct, Chester, MD 21619
  • /36

    $515,000

    • 3 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    300 Skyler Ave, Chester, MD 21619

    Welcome to this beautifully maintained home in a quiet Chester neighborhood, just one house off the water. Situated on a spacious 0.75-acre lot, this recently updated home has been freshly painted and is move-in ready. The main level features a spacious kitchen with granite countertops, stainless steel appliances, an island with additional storage, and elegant cabinetry. The open dining area

    Mike Altobelli RE/MAX Realty Services

    300 Skyler Ave, Chester, MD 21619
  • /68

    $1,450,000

    • 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

    Cynthia Sullivan Sullivan Select, LLC.

    1622 Bayside Dr, Chester, MD 21619
  • /24

    $449,000

    • 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
  • /54

    $459,900

    • 3 Beds
    • 2.5 Baths
    • 1,706 Sq Ft

    122 Dundee Ave, Chester, MD 21619

    Rare Opportunity to Own this Amazing 3 BR/2.5BA SFH w/ large backyard on Kent Island. Bonus NO HOA!!! Only One Family Owned. You will fall in love with this Modern Split Foyer with a GREAT OPEN LAYOUT! Home Features Hardwood Flooring through-out the Gourmet Kitchen, Dining Area, Family Room, Hallway and even on the Steps, Cathedral Ceilings, Open Concept Kitchen, Dining and Family Room. All

    Sandy Patterson Taylor Properties

    122 Dundee Ave, Chester, MD 21619
  • /49

    $499,000

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

    203 Anchor Ln, Chester, MD 21619

    Here is your chance to buy in Castle Marina without the hassle! Close walk to local restaurants, or hop onto the cross island trail! Gorgeous classic Kent Island brick rancher featuring new roof, new refrigerator, new water softener & oven range, new water heater, barn doors throughout, wood burning stove, and fully heated/air condition controlled garage! This property is approved for an

    Megan Rosendale Rosendale Realty

    203 Anchor Ln, Chester, MD 21619
  • /45

    $509,500

    • 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

    Bob Chew Berkshire Hathaway HomeServices PenFed Realty

    312 Hanna Ct, 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
  • /35

    $359,900

    • 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
  • /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
  • /56

    $399,900

    • 4 Beds
    • 3 Baths
    • 2,682 Sq Ft

    502 Dominion Rd, Chester, MD 21619

    Charming Home with Endless Potential on Spacious .8-Acre Lot!Discover this unique opportunity to own a property brimming with charm and possibilities! Nestled on a generous .8-acre lot, this home offers the potential for an additional lot—perfect for future expansion or investment—as the previous owner began work to make it a reality.This 2-story gem showcases custom carpentry

    Jim Davidson Coldwell Banker Waterman Realty

    502 Dominion Rd, Chester, MD 21619
  • /94

    $579,000

    • 3 Beds
    • 2.5 Baths
    • 1,852 Sq Ft

    214 Claiborne St, Chester, MD 21619

    Discover refined coastal living in this meticulously maintained contemporary home in the sought-after Gibson's Grant water front community. Built in 2014, this thoughtfully designed 3 bedroom, 2.5 bath residence offers over 1,852 square feet of living space and combines modern aesthetics with contemporary architectural details across two finished levels. As you approach you are greeted by an

    Barbara McCaffrey Redfin Corp

    214 Claiborne St, Chester, MD 21619

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