109

Chester, MD Homes for Sale

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  • 540 Warbler Way, Chester, MD 21619
    540 Warbler Way, Chester, MD 21619
    540 Warbler Way, Chester, MD 21619
    /29

    $929,990

    New Construction $41K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    540 Warbler Way, Chester, MD 21619

    Elegant kitchen featuring white cabinetry & glass-front uppers.Vast center island, perfect for prepping family meals.Stunning fireplace adds character & warmth to spacious great room.Lavish primary suite & bath featuring bath barn door.Secluded Extra Suite for overnight guests.Functional home office for leisure activities.Cozy screened patio for outdoor relaxation.

    K. Hovnanian Homes Builder
    540 Warbler Way, Chester, MD 21619
  • 131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    /11

    $709,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    Kelly Plan at Four Seasons at Kent Island - Single Family, 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 Homes Builder
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
  • 830 Warbler Way Unit 34, Chester, MD 21619
    830 Warbler Way Unit 34, Chester, MD 21619
    830 Warbler Way Unit 34, Chester, MD 21619
    /18

    $849,990

    New Construction $29K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    830 Warbler Way Unit 34, Chester, MD 21619

    Gourmet kitchen with large island & built-in wall oven.Bright dining area includes a convenient dry bar.Great room features an electric fireplace.Balcony offers a perfect space for outdoor entertaining.Owner's suite includes a sitting room & balcony access.Two walk-in closets provide ample storage in the suite.Spa bath features dual vanities for added convenience.

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 34, Chester, MD 21619
  • 532 Cross Creek Ct, Chester, MD 21619
    532 Cross Creek Ct, Chester, MD 21619
    /2

    $555,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,486 Sq Ft

    532 Cross Creek Ct, Chester, MD 21619

    Eastern Shore living begins here! Welcome to 532 Cross Creek Court in the desirable Claybourne Woods community of Chester. This beautifully maintained 4-bedroom, 2.5-bath home offers plenty of space to gather, relax, and create lasting memories. Whether you're hosting gatherings, enjoying quiet evenings at home, or entertaining friends, this home provides the perfect setting. Located on Kent

    Jerilynn Montgomery Long & Foster Real Estate, Inc.

    532 Cross Creek Ct, Chester, MD 21619
  • 233 Peregrine Dr, Chester, MD 21619
    233 Peregrine Dr, Chester, MD 21619
    233 Peregrine Dr, Chester, MD 21619
    /63

    $724,999

    $25K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    233 Peregrine Dr, Chester, MD 21619

    Why wait for new construction when you can move right into this beautiful Simone model in the highly sought-after Four Seasons at Kent Island? This spacious home offers 4 bedrooms, 3 full baths, and the perfect blend of comfort, style, and low-maintenance living.The open floor plan makes everyday living and entertaining easy, with a bright kitchen featuring quartz countertops, stainless steel

    Michelle Abplanalp Rosendale Realty

    233 Peregrine Dr, Chester, MD 21619
  • 302 Merganser Ct Unit A, Chester, MD 21619
    302 Merganser Ct Unit A, Chester, MD 21619
    302 Merganser Ct Unit A, Chester, MD 21619
    /21

    $309,900

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

    302 Merganser Ct Unit A, Chester, MD 21619

    Welcome to coastal living in this beautifully updated first-floor, end-unit condo, offering the perfect blend of comfort, convenience, and resort-style amenities in one of Kent Island's most sought-after communities. With no stairs to navigate and handicap-accessible features, this home provides effortless everyday living while enjoying the added privacy and abundant natural light that only an

    Jen Kenney Keller Williams Flagship

    302 Merganser Ct Unit A, Chester, MD 21619
  • 102 Boatswain Way Unit 2932, Chester, MD 21619
    102 Boatswain Way Unit 2932, Chester, MD 21619
    102 Boatswain Way Unit 2932, Chester, MD 21619
    /47

    $829,990

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

    102 Boatswain Way Unit 2932, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office

    David Willman Berkshire Hathaway HomeServices PenFed Realty - OP

    102 Boatswain Way Unit 2932, Chester, MD 21619
  • 132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    /29

    $700,000

    $80K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    132 Wheelhouse Way Unit 11, Chester, MD 21619

    Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its replacement value. Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four

    Matthew Arnold Real Broker, LLC

    132 Wheelhouse Way Unit 11, Chester, MD 21619
  • 233 Kingfisher Ln, Stevensville, MD 21666
    233 Kingfisher Ln, Stevensville, MD 21666
    233 Kingfisher Ln, Stevensville, MD 21666
    /84

    $999,000

    $46K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    233 Kingfisher Ln, Stevensville, MD 21666

    Welcome to luxury coastal living in the highly desirable Four Seasons at Kent Island 55+ community in Chester. Built in 2025, this practically new home offers the perfect blend of elegance, comfort, and convenience — without the wait for new construction. Ideally situated on coveted Kingfisher Lane, this exceptional Tuscaloosa model offers over 3,200 square feet of beautifully designed living

    Tara Trout Samson Properties

    233 Kingfisher Ln, Stevensville, MD 21666
  • 111 Marshgrass Way Unit 43, Chester, MD 21619
    111 Marshgrass Way Unit 43, Chester, MD 21619
    111 Marshgrass Way Unit 43, Chester, MD 21619
    /65

    $765,000

    • 2 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 43, Chester, MD 21619

    Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floor unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design

    John Freeman Coldwell Banker Realty

    111 Marshgrass Way Unit 43, Chester, MD 21619
  • 532 Warbler Way, Chester, MD 21619
    532 Warbler Way, Chester, MD 21619
    532 Warbler Way, Chester, MD 21619
    /25

    $929,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    532 Warbler Way, Chester, MD 21619

    First-floor Extra Suite adds flexibility for guests.Ceiling detail & crown molding carry through the kitchen and great room.Stacked cabinetry with glass-front uppers brings added depth to the kitchen.Fireplace creates a warm focal point in the great room.Screened patio off the great room extends the living space outdoors.Decorative feature walls in the foyer & primary suite

    K. Hovnanian Homes Builder
    532 Warbler Way, Chester, MD 21619
  • 2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    2000 Herons Nest Way Unit 401, Chester, MD 21619
    /36

    $700,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    Newly adjusted price. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River.The gourmet kitchen is the heart of the home,

    Matthew Arnold Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • 205 Riverside Dr, Chester, MD 21619
    205 Riverside Dr, Chester, MD 21619
    205 Riverside Dr, Chester, MD 21619
    /38

    $749,000

    • 3 Beds
    • 2 Baths
    • 1,524 Sq Ft

    205 Riverside Dr, Chester, MD 21619

    Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This

    Melissa Chick Engel & Völkers Annapolis

    205 Riverside Dr, Chester, MD 21619
  • 830 Warbler Way Unit 33, Chester, MD 21619
    830 Warbler Way Unit 33, Chester, MD 21619
    830 Warbler Way Unit 33, Chester, MD 21619
    /25

    $689,990

    New Construction $28K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    830 Warbler Way Unit 33, Chester, MD 21619

    Private home office with elegant French double doors.Gourmet kitchen features a center island & built-in wall oven.Dining area includes a dry bar for added convenience.Great room with an electric fireplace opens to the balcony.Owner's suite offers balcony access for a relaxing retreat.Spa bath provides comfort with dual vanities & modern design.Laundry room includes

    K. Hovnanian Homes Builder
    830 Warbler Way Unit 33, Chester, MD 21619
  • 131 Flycatcher Way Unit 36503530, Chester, MD 21619
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
    /21

    $589,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    Severn Plan at Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms.Lavish gourmet kitchen and formal dining area.Huge great room with large corner balcony.Fantastic owner’s suite and sitting room with access to balcony.Extravagant owner’s spa bath with two walk-in closets.Large secondary bedrooms for all of your company.Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
  • 320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    /3

    $897,750

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 2,331 Sq Ft

    320 Bayberry Dr, Chester, MD 21619

    Be part of the fastest growing 55+ community on Marylands Eastern Shore. Bayberry was the first street in Four Seasons Kent Island where construction in 2021 was superior to those today. 320 Bayberry Drive sits on a Premium Lot which abuts lands owned and maintained by the HOA. The developer is charging a Lot Premium of up to $400,000 for the extra space on remaining lots. The seller just

    Jeremy McDonough Mr. Lister Realty

    320 Bayberry Dr, Chester, MD 21619
  • 0 Harley Ln, Chester, MD 21619
    0 Harley Ln, Chester, MD 21619
    /2

    $149,900

    • Land
    • 12,632 Sq Ft
    • $516,897 per Acre

    0 Harley Ln, Chester, MD 21619

    Lot 1 of two newly formed building lots on Kent Island in Chester just off Dominion Road. Sewer Allocation has been paid (a $11,800 value!) and this lot has a working well! The site work has been done. Right around the corner from the Goodhands Creek Landing to launch your boat. Close to Rt 50/301 & Main Street for convenient commuting and shopping!

    Jason Dey Kevin Dey Realty

    0 Harley Ln, Chester, MD 21619
  • 209 Harrier Way, Chester, MD 21619
    209 Harrier Way, Chester, MD 21619
    209 Harrier Way, Chester, MD 21619
    /122

    $747,900

    Open Sun 9AM - 11AM
    • 4 Beds
    • 3 Baths
    • 3,142 Sq Ft

    209 Harrier Way, Chester, MD 21619

    Welcome Home! JUST LISTED & OPEN Sunday 8/9 from 9am-11am OR by APPT DAILY! Barely lived in, this home still looks like new, offering all the benefits of new construction without the wait. The thoughtfully designed floor plan of the Simone model offers exceptional flexibility. The main level features a stunning gourmet kitchen with crisp white cabinetry, a large center island, stainless steel

    Violeta Aguirre Long & Foster Real Estate, Inc.

    209 Harrier Way, Chester, MD 21619
  • 102 Boatswain Way Unit 43, Chester, MD 21619
    102 Boatswain Way Unit 43, Chester, MD 21619
    102 Boatswain Way Unit 43, Chester, MD 21619
    /32

    $929,990

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

    102 Boatswain Way Unit 43, Chester, MD 21619

    Beautiful gourmet kitchen featuring designer cabinetry & an efficient layout for everyday living.Bright great room with an electric fireplace adding warmth & character.Dining area complemented by a convenient dry bar for easy entertaining.Private owner’s suite with walk-in closet & direct access to the spa bath.Home office with double doors ideal for work or quiet

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 43, Chester, MD 21619
  • 193 Spinnaker Way, Chester, MD 21619
    193 Spinnaker Way, Chester, MD 21619
    193 Spinnaker Way, Chester, MD 21619
    /41

    $856,000

    • 3 Beds
    • 3 Baths
    • 2,527 Sq Ft

    193 Spinnaker Way, Chester, MD 21619

    Welcome to Your Dream Home at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Lille Loft model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious

    Alex Estill Long & Foster Real Estate, Inc.

    193 Spinnaker Way, Chester, MD 21619
  • 723 Warbler Way, Chester, MD 21619
    723 Warbler Way, Chester, MD 21619
    723 Warbler Way, Chester, MD 21619
    /15

    $789,990

    New Construction $40K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    723 Warbler Way, Chester, MD 21619

    Elegant kitchen with white cabinetry & center island.Open concept living spaces featuring cozy fireplace.Serene primary suite with stylish ceiling treatment & feature wall.Polished primary bath featuring brushed nickel finishes & walk-in closet.Formal home office provides a quiet space for working remotely.Versatile screened patio for relaxing with friends.Functional

    K. Hovnanian Homes Builder
    723 Warbler Way, Chester, MD 21619
  • 232 Evelyne St, Chester, MD 21619
    232 Evelyne St, Chester, MD 21619
    232 Evelyne St, Chester, MD 21619
    /35

    $840,000

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,312 Sq Ft

    232 Evelyne St, Chester, MD 21619

    Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs,

    Courtney Chipouras TTR Sotheby's International Realty

    232 Evelyne St, Chester, MD 21619
  • 0 Harley Ln, Chester, MD 21619
    0 Harley Ln, Chester, MD 21619
    /2

    $139,900

    • Land
    • 12,632 Sq Ft
    • $482,414 per Acre

    0 Harley Ln, Chester, MD 21619

    Lot 2 of two newly formed building lots on Kent Island in Chester just off Dominion Road. Sewer Allocation has been paid (a $11,800 value)! The site work has been done. Right around the corner from the Goodhand's Creek Landing to launch your boat or go fishing. Close to Rt 50/301 & Main Street for convenient commuting and shopping!

    Jason Dey Kevin Dey Realty

    0 Harley Ln, Chester, MD 21619
  • 123 Flycatcher Way, Chester, MD 21619
    123 Flycatcher Way, Chester, MD 21619
    123 Flycatcher Way, Chester, MD 21619
    /24

    $1,100,000

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    123 Flycatcher Way, Chester, MD 21619

    Well-equipped kitchen with stacked dark stained cabinetry & glass uppers. Cozy fireplace adds warmth & character to spacious great room. Tranquil primary suite with generous walk-in closet. Productive home office for studying or reading. Private Extra Suite, great for overnight guests. Inviting screened patio for outdoor entertaining. Second floor loft provide addtionial living space.

    K. Hovnanian Homes Builder
    123 Flycatcher Way, Chester, MD 21619
  • 111 Marshgrass Way Unit 21, Chester, MD 21619
    111 Marshgrass Way Unit 21, Chester, MD 21619
    111 Marshgrass Way Unit 21, Chester, MD 21619
    /57

    $680,000

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    111 Marshgrass Way Unit 21, Chester, MD 21619

    A rare blend of coastal proximity and refined living unfolds within this beautifully appointed corner residence in the sought-after 55+ waterfront community of Four Seasons at Kent Island. Built in 2024 and impeccably maintained , this like-new residence offers the comfort of immediate enjoinment without the wait for new construction. Positioned near a tranquil creek leading to the Chesapeake

    Marisol Cardona Samson Properties

    111 Marshgrass Way Unit 21, Chester, MD 21619
  • 106 Bodys Neck Rd, Chester, MD 21619
    106 Bodys Neck Rd, Chester, MD 21619
    106 Bodys Neck Rd, Chester, MD 21619
    /46

    $435,000

    • 3 Beds
    • 2.5 Baths
    • 1,595 Sq Ft

    106 Bodys Neck Rd, Chester, MD 21619

    Welcome to Bayside, where coastal living and resort-style amenities come together in one of the area’s most desirable waterfront communities. This 3-bedroom, 2.5-bath condo offers a relaxing marina-side setting with both upper and lower decks overlooking the marina, creating the perfect backdrop for morning coffee, evening sunsets, and everything in between. Inside, you’ll find a spacious layout

    Bill Longest Realty Navigator

    106 Bodys Neck Rd, Chester, MD 21619
  • 102 Boatswain Way Unit 33, Chester, MD 21619
    102 Boatswain Way Unit 33, Chester, MD 21619
    102 Boatswain Way Unit 33, Chester, MD 21619
    /32

    $829,990

    New Construction $33K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 33, Chester, MD 21619

    Private home office with elegant French doors. Chef-worthy gourmet kitchen with sprawling island. Formal dining area with dry bar, perfect for entertaining. Gorgeous great room with cozy electric fireplace. Sophisticated owner's suite with triple windows. Stunning owner's spa bath featuring split vanities. Beautiful balcony has access through primary suite & great room.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 33, Chester, MD 21619
  • 3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    /66

    $479,000

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    3000 Herons Nest Way Unit 11, Chester, MD 21619

    A price improvement has been made, making this unit the best value in the entire community. This home shows like a model with approximately $55,000.00 in upgrades. No need to wait for new construction this unit is ready for immediate occupancy. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings

    John Freeman Coldwell Banker Realty

    3000 Herons Nest Way Unit 11, Chester, MD 21619
  • 131 Flycatcher Way Unit 36455262, Chester, MD 21619
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
    131 Flycatcher Way Unit 36455262, Chester, MD 21619
    /16

    $883,990

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

    Munich ESP Plan at Four Seasons at Kent Island - Single Family, 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. Large covered patio for enjoying the outdoors.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36455262, Chester, MD 21619

Showing Results 81 - 109, Page 3 of 3

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