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Chester, MD Homes for Sale in a Senior Community

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  • 110 Boatswain Way Unit 3044, Chester, MD 21619
    110 Boatswain Way Unit 3044, Chester, MD 21619
    110 Boatswain Way Unit 3044, Chester, MD 21619
    /44

    $989,990 New Construction

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

    110 Boatswain Way Unit 3044, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in November 2026, this home combines modern style with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. The owner’s suite includes a sitting room and large walk-in closets, providing a

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3044, Chester, MD 21619
  • 110 Boatswain Way Unit 3042, Chester, MD 21619
    110 Boatswain Way Unit 3042, Chester, MD 21619
    110 Boatswain Way Unit 3042, Chester, MD 21619
    /52

    $799,990 New Construction

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

    110 Boatswain Way Unit 3042, 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 October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3042, Chester, MD 21619
  • 110 Warbler Way Unit 3032, Chester, MD 21619
    110 Warbler Way Unit 3032, Chester, MD 21619
    110 Warbler Way Unit 3032, Chester, MD 21619
    /52

    $699,990 New Construction

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

    110 Warbler Way Unit 3032, Chester, MD 21619

    The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 baths, and a 1-car garage. The main living area is anchored by an electric fireplace, while a dry bar adds both function and style for entertaining. A dedicated home office with lighted French doors provides a flexible space

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3032, Chester, MD 21619
  • 110 Warbler Way Unit 3031, Chester, MD 21619
    110 Warbler Way Unit 3031, Chester, MD 21619
    110 Warbler Way Unit 3031, Chester, MD 21619
    /44

    $849,990 New Construction

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

    110 Warbler Way Unit 3031, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3031, Chester, MD 21619
  • 110 Warbler Way Unit 3021, Chester, MD 21619
    110 Warbler Way Unit 3021, Chester, MD 21619
    110 Warbler Way Unit 3021, Chester, MD 21619
    /44

    $749,990 New Construction

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

    110 Warbler Way Unit 3021, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3021, Chester, MD 21619
  • 311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    311 Kingfisher Ln, Chester, MD 21619
    /40

    $899,990 New Construction

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

    311 Kingfisher Ln, Chester, MD 21619

    The Tuscaloosa, located on Lot 588, is scheduled for an April 2026 settlement and offers generous space with 5 bedrooms, 4.5 baths, and a 3-car garage—ideal for growing households and effortless entertaining. Designed with both comfort and function in mind, this home includes a private home office, a screened patio for relaxed outdoor living, and a striking stone fireplace complemented by ceiling

    Mary Anne Kowalewski KOVO Realty

    311 Kingfisher Ln, Chester, MD 21619
  • 127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    /49

    $1,100,000 New Construction

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

    127 Flycatcher Way, Chester, MD 21619

    The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a

    Mary Anne Kowalewski KOVO Realty

    127 Flycatcher Way, Chester, MD 21619
  • 131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    /13

    $701,990 New Construction

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

    Simone Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, 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 floor with 2 secondary bedrooms and full bath.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • 131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    /12

    $636,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    Bernstein II Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, 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 Homes Builder
    131 Flycatcher Way Unit 36492116, 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

    $774,990 New Construction

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

    Kelly Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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
  • 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 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
  • 131 Flycatcher Way Unit 36493320, Chester, MD 21619
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
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    $499,990 New Construction

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

    Chester Plan at K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owner’s suite with spa bath and access to balcony. Large secondary bedroom with access to balcony. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493320, 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

    $584,990 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
  • 111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    111 Flycatcher Way, Chester, MD 21619
    /37

    $1,456,462 New Construction

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

    111 Flycatcher Way, Chester, MD 21619

    Beautiful kitchen with wood-stained cabinetry & pendant lighting. Open concept living spaces with vaulted ceiling & elegant fireplace. Private primary suite & bath with generous walk-in closet. Productive home office for working remotely. Secluded Extra Suite, ideal for overnight guests. Stunning screened patio for outdoor entertaining. Attached 3-car tandem garage for vehicles & storage.

    K. Hovnanian Homes Builder
    111 Flycatcher Way, Chester, MD 21619
  • 117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    117 Flycatcher Way, Chester, MD 21619
    /24

    $1,400,000 New Construction

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

    117 Flycatcher Way, Chester, MD 21619

    Formal dining room off the foyer for hosting celebrations. Breathtaking kitchen with stacked grey cabinetry & glass uppers. Sprawling quartz island perfect for prep & dining. Vaulted ceiling with ceiling beams connects dining area and great room. Elegant fireplace and sliding door to screened patio in great room. Private home office for working remotely. Primary suite & bath with dual vanities

    K. Hovnanian Homes Builder
    117 Flycatcher Way, Chester, MD 21619
  • 123 Flycatcher Way, Chester, MD 21619
    123 Flycatcher Way, Chester, MD 21619
    123 Flycatcher Way, Chester, MD 21619
    /24

    $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
  • 111 Marshgrass Way Unit 43, Chester, MD 21619
    111 Marshgrass Way Unit 43, Chester, MD 21619
    111 Marshgrass Way Unit 43, Chester, MD 21619
    /33

    $765,000 Coming Soon

    • 2 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 43, Chester, MD 21619

    Rare penthouse 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 ever builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the living room, dining area, and kitchen areas, all enhanced by

    John Freeman Coldwell Banker Realty

    111 Marshgrass Way Unit 43, Chester, MD 21619
  • 215 Kingfisher Ln, Stevensville, MD 21666
    215 Kingfisher Ln, Stevensville, MD 21666
    /2

    $1,100,000 Open House 4/18

    • 5 Beds
    • 4 Baths
    • 3,914 Sq Ft

    215 Kingfisher Ln, Stevensville, MD 21666

    COMING SOON! Professional Pictures coming...... Why wait to build? This less-than-one-year-old Tusculusa model on sought-after Kingfisher Lane sits just across from the Chester River, offering peekaboo water views from the covered front porch. You can see the clubhouse from the home! Loaded with over $70k in premium upgrades—owned solar, custom closets, and designer window treatments—all done for

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, Stevensville, MD 21666

Showing Results 41 - 58, Page 2 of 2

Maryland Queen Anne's County Chester

Homes for Sale in a Senior Community in Chester, MD

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In Chester, there are currently 58 homes for sale in a senior community, offering a peaceful and supportive environment for retirees and older adults. Within retirement communities or over 55 communities, residents can access various amenities and services tailored to their specific needs and preferences. From fitness centers and social gatherings to maintenance-free living arrangements and on-site healthcare facilities, homes in senior communities provide residents with opportunities for a fulfilling lifestyle. Browse the selection of condos and homes for sale in senior communities in Chester, MD and find the perfect place for your retirement years.

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