Chester, MD Homes for Sale with Garage

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  $915,000

  • 6 Beds
  • 4.5 Baths
  • 4,165 Sq Ft

  109 John Gibson Dr, Chester, MD 21619

  Start the New Year as a resident of Gibson’s Grant!Discover over 4,100 sq. ft. of high-end, custom elegance in this exceptional Eastern Shore home—perfectly located in one of Chester’s most sought-after waterfront communities. With 6 bedrooms, 4.5 baths, and designer touches at every turn, this residence offers the space, craftsmanship, and lifestyle today’s buyers crave.Step inside the

  Lisa Barton Coldwell Banker Realty

  109 John Gibson Dr, Chester, MD 21619
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  $1,299,990 New Construction

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

  132 Wheelhouse Way, Chester, MD 21619

  This beautifully designed Chester Model Home offers sophisticated comfort and modern convenience, ready for immediate move-in with a flexible month-to-month leaseback opportunity. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home blends style and function seamlessly. Thoughtful touches include a fully furnished interior, a dry bar perfect for entertaining, and an electric fireplace

  Mary Anne Kowalewski KOVO Realty

  132 Wheelhouse Way, Chester, MD 21619
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  $574,990 New Construction

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

  Severn Plan at K. Hovnanian’s® 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
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  $1,899,000

  • 4 Beds
  • 6 Baths
  • 3,460 Sq Ft

  2907 Cox Neck Rd E, Chester, MD 21619

  Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside

  Brad Kappel TTR Sotheby's International Realty

  2907 Cox Neck Rd E, Chester, MD 21619
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  $1,400,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,930 Sq Ft

  117 Flycatcher Way, Chester, MD 21619

  The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio

  Mary Anne Kowalewski KOVO Realty

  117 Flycatcher Way, Chester, MD 21619
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  $1,389,667 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
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  $555,900

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

  3000 Herons Nest Way Unit 11, Chester, MD 21619

  Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. This highly sought-after first-floor condo is move-in ready and has been meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced by crown

  John Freeman Coldwell Banker Realty

  3000 Herons Nest Way Unit 11, Chester, MD 21619
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  $883,990 New Construction

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

  Munich ESP Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, 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
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  $799,990 Open Sat 11AM - 4PM

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

  527 Warbler Way, Stevensville, MD 21666

  Ready NOW! This stunning Kerr home offers an inviting open floor plan designed for both comfort and functionality. Featuring 3 bedrooms, 3 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the

  Mary Anne Kowalewski KOVO Realty

  527 Warbler Way, Stevensville, MD 21666

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