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Chester, MD Homes for Sale in a Senior Community

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  • 4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    /70

    $560,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 390-0346

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $814,900

    • 3 Beds
    • 3 Baths
    • 2,795 Sq Ft

    135 Nauset Ln, Chester, MD 21619

    If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities.

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset Ln, Chester, MD 21619
  • 131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    /12

    $499,990 New Construction

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

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

    Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owner’s suite with spa bath . Fantastic great room with large windows for your viewing pleasure. Large secondary bedroom with opt. door to access patio. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    /10

    $752,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    Taylor Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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 Homes Builder
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
  • 131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    /12

    $886,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    Mykonos Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, 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 storage.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
  • 131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    /27

    $858,990 New Construction

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

    Franklin Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, 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 Homes Builder
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • 131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    /24

    $669,990 New Construction

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

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, 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 Homes Builder
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
  • 131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    /27

    $819,990 New Construction

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

    Kerr Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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 Homes Builder
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • 131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    /40

    $848,990 New Construction

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

    Tuscaloosa Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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 Homes Builder
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • 1000 Herons Nest Way Unit 42, Chester, MD 21619
    1000 Herons Nest Way Unit 42, Chester, MD 21619
    1000 Herons Nest Way Unit 42, Chester, MD 21619
    /54

    $599,000

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

    1000 Herons Nest Way Unit 42, Chester, MD 21619

    Rarely on the market Penthouse level Chester model available immediately! Balcony views from the top floor leftside provide view of the Chester River, Macum Creek and the Community Kayak's. Located within the serene and vibrant community of Four Seasons at Kent Island, this exquisite 2-bedroom, 2.5 bath Built in 2020, this elegant unit combines modern design with high-end finishes, creating a

    Dan Judge RE/MAX United Real Estate

    1000 Herons Nest Way Unit 42, Chester, MD 21619
  • 169 Harrier Way, Chester, MD 21619
    169 Harrier Way, Chester, MD 21619
    169 Harrier Way, Chester, MD 21619
    /85

    $779,900 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,394 Sq Ft

    169 Harrier Way, Chester, MD 21619

    Look no further—welcome to the prestigious 55+ resort-style community of Four Seasons at Kent Island, where refined living meets effortless elegance. This exquisitely upgraded Killarney model offers over 2,300 square feet of thoughtfully designed single-level living, featuring an open-concept layout and high-end finishes throughout.At the heart of the home is a stunning gourmet kitchen,

    Dorothea Slaughter Century 21 Redwood Realty

    169 Harrier Way, Chester, MD 21619
  • 249 Warbler Way, Chester, MD 21619
    249 Warbler Way, Chester, MD 21619
    249 Warbler Way, Chester, MD 21619
    /68

    $699,000

    • 2 Beds
    • 2 Baths
    • 2,025 Sq Ft

    249 Warbler Way, Chester, MD 21619

    **OPEN HOUSE SATURDAY 3/28/26! 10am to 12pm** No waiting on the Builder here! This almost brand new Jenkins II Model was built just last year and boasts soaring, coffered and vaulted ceilings in the 2,025 sf of spaciousness! The generously sized primary suite & spa like bath with a huge walk-in-closet, double vanities & walk-in-shower is sure to make you feel like Royalty! The 2nd bedroom & full

    Pamela Ackermann-Doll RE/MAX Executive

    249 Warbler Way, Chester, MD 21619
  • 266 Peregrine Dr, Stevensville, MD 21666
    266 Peregrine Dr, Stevensville, MD 21666
    266 Peregrine Dr, Stevensville, MD 21666
    /73

    $728,000

    • 4 Beds
    • 3 Baths
    • 2,870 Sq Ft

    266 Peregrine Dr, Stevensville, MD 21666

    Huge Price Reduction on this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features 4 bedrooms and 3 full baths is awaiting it's next owner and priced well below the new construction models. With recent improvements including paint and Plantation Shutters, this home is move in ready so that you can enjoy this

    Edward Beres RE/MAX Executive

    266 Peregrine Dr, Stevensville, MD 21666
  • 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
    /83

    $750,000

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

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    HERE IT IS! This Rare Luxurious Severn Penthouse, available immediately, offers a lifestyle that seamlessly blends comfort and elegance. Built in 2020, this beautifully maintained residence showcases an open floor plan with windows throughout that invite natural light to dance across its spacious interiors, creating a warm, inviting atmosphere. Step into the heart of the home, where a stunning

    Veronica Lawson Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • 132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    /45

    $995,000

    • 4 Beds
    • 3.5 Baths
    • 3,634 Sq Ft

    132 Kestrel Ln, Chester, MD 21619

    Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay. From the moment you arrive, the covered front

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, Chester, MD 21619
  • 230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    230 Switchgrass Way Unit 21, Chester, MD 21619
    /67

    $694,500 Open Sat 10AM - 12PM

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

    230 Switchgrass Way Unit 21, Chester, MD 21619

    --------------------------------------EXCEPTIONAL PANORAMIC VIEWS -------------------------------------Immediate Move In Ready. Nature, water and sunshine abound in this beautifully situated, stunning 3BR corner unit at Four Seasons. Flexible closing available. South, west and north exposures through 17 windows and two sets of sliding doors assure that this condo is drenched in sunshine, water

    Lawrence Doyle Long & Foster Real Estate, Inc.

    230 Switchgrass Way Unit 21, Chester, MD 21619
  • 111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, Chester, MD 21619
    111 Marshgrass Way Unit 22, Chester, MD 21619
    /102

    $539,000

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

    111 Marshgrass Way Unit 22, Chester, MD 21619

    Rare resale condo, turnkey! Your dream retreat awaits in this stunning luxury condo, where modern elegance meets breathtaking natural beauty. This exquisite residence features two spacious bedrooms, each with its own en-suite bath, and an additional half bath for guests. The thoughtfully designed office boasts custom built-in cabinets, providing both functionality and style.--Step into the heart

    Dee Dee Miller Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 22, Chester, MD 21619
  • 1000 Herons Nest Way Unit 23, Chester, MD 21619
    1000 Herons Nest Way Unit 23, Chester, MD 21619
    1000 Herons Nest Way Unit 23, Chester, MD 21619
    /32

    $494,900

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

    1000 Herons Nest Way Unit 23, Chester, MD 21619

    Welcome to 1000 Herons Nest Way, where you can live the good life at an great price. This immaculate two bedroom condo, with two and a half baths and additional flex space, provides turn key convenience and resort style amenities. This home is a MUST SEE! This FORMER MODEL is like new and includes features that other condos won’t - including decorator upgrades, custom designed closets, plantation

    Nola Meyers EXP Realty, LLC

    1000 Herons Nest Way Unit 23, Chester, MD 21619
  • 200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    /44

    $659,900

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    200 Harrier Way Unit 21, Chester, MD 21619

    Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway tile

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, Chester, MD 21619
  • 1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    /28

    $499,000

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

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Step into the good life in the sought-after Four Seasons on Kent Island, where low-maintenance living meets waterfront vibes. This 2-bedroom, 2-bath home offers spacious one-level living with an open, airy layout, freshly painted interiors, and a stylish kitchen featuring a modern glass subway tile backsplash—perfect for entertaining or unwinding after a day on the Shore. The 1-car garage plus

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • 110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    110 Kinglet Ct, Chester, MD 21619
    /40

    $889,990 New Construction

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

    110 Kinglet Ct, Chester, MD 21619

    First-floor Extra Suite with private bath for guest comfort. Home office with sliding barn doors adds character. Kitchen, dining area & great room share a vaulted ceiling with beams. Kitchen with central island highlighted by matte black pendant lighting. Shiplap fireplace with hearth anchors the great room. Screened patio off the great room for relaxed outdoor living. Primary suite with ceiling

    K. Hovnanian Homes Builder
    110 Kinglet Ct, Chester, MD 21619
  • 102 Boatswain Way Unit 11, Chester, MD 21619
    102 Boatswain Way Unit 11, Chester, MD 21619
    102 Boatswain Way Unit 11, Chester, MD 21619
    /13

    $663,917 New Construction

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

    102 Boatswain Way Unit 11, Chester, MD 21619

    Open home office just off the main living space. Gourmet kitchen with central island for everyday cooking & gathering. Dining area with dry bar for easy entertaining. Electric fireplace adds warmth to the great room. Patio connects seamlessly to the great room & owner’s suite. Owner’s suite with dual closets for added storage. Owner’s bath with dual sinks & glass shower enclosure. Bedroom 2 with

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 11, Chester, MD 21619
  • 102 Boatswain Way Unit 21, Chester, MD 21619
    102 Boatswain Way Unit 21, Chester, MD 21619
    102 Boatswain Way Unit 21, Chester, MD 21619
    /21

    $901,540 New Construction

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

    102 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island & sleek finishes. Dining area with built-in dry bar for easy entertaining. Bright great room with electric fireplace & open layout. Private balcony just off the great room. Owner’s suite with dual walk-in closets for added storage. Sitting room in owner’s suite with direct balcony access. Spa-inspired owner’s bath with dual sinks & glass-enclosed

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 21, Chester, MD 21619
  • 102 Boatswain Way Unit 12, Chester, MD 21619
    102 Boatswain Way Unit 12, Chester, MD 21619
    102 Boatswain Way Unit 12, Chester, MD 21619
    /13

    $663,917 New Construction

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

    102 Boatswain Way Unit 12, Chester, MD 21619

    Open home office for flexible work or study. Gourmet kitchen with central island at the heart of the home. Dining area with dry bar for easy entertaining. Great room with electric fireplace for a cozy focal point. Patio off the great room with direct access to the owner's suite. Owner's suite with dual closets for added storage. Owner's bath with dual sinks & glass shower enclosure. Bedroom 2

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 12, Chester, MD 21619
  • 102 Boatswain Way Unit 34, Chester, MD 21619
    102 Boatswain Way Unit 34, Chester, MD 21619
    102 Boatswain Way Unit 34, Chester, MD 21619
    /21

    $1,003,673 New Construction

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

    102 Boatswain Way Unit 34, Chester, MD 21619

    Stylish gourmet kitchen centered around a large island. Dining space with convenient dry bar for hosting. Open great room featuring an electric fireplace. Balcony extending from the main living area. Owner’s suite with two spacious walk-in closets. Private sitting area in owner’s suite with balcony connection. Owner’s bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 34, Chester, MD 21619
  • 102 Warbler Way Unit 2912, Chester, MD 21619
    102 Warbler Way Unit 2912, Chester, MD 21619
    102 Warbler Way Unit 2912, Chester, MD 21619
    /63

    $649,990 New Construction

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

    102 Warbler Way Unit 2912, Chester, MD 21619

    Welcome to the Magothy, 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

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2912, Chester, MD 21619
  • 102 Warbler Way Unit 2934, Chester, MD 21619
    102 Warbler Way Unit 2934, Chester, MD 21619
    102 Warbler Way Unit 2934, Chester, MD 21619
    /44

    $989,990 New Construction

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

    102 Warbler Way Unit 2934, 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 December 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2934, Chester, MD 21619
  • 211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    /19

    $739,900 New Construction

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

    211 Switchgrass Way Unit 31, Chester, MD 21619

    Striking gourmet kitchen with designer cabinets & chef-worthy island.Elegant dining area featuring fancy dry bar.Refined great room featuring stunning fireplace.Serene owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish shower.Wonderful balcony for relaxing outdoors.

    K. Hovnanian Homes Builder
    211 Switchgrass Way Unit 31, Chester, MD 21619
  • 102 Warbler Way Unit 2921, Chester, MD 21619
    102 Warbler Way Unit 2921, Chester, MD 21619
    102 Warbler Way Unit 2921, Chester, MD 21619
    /44

    $889,990 New Construction

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

    102 Warbler Way Unit 2921, 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 December 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2921, Chester, MD 21619
  • 102 Warbler Way Unit 2911, Chester, MD 21619
    102 Warbler Way Unit 2911, Chester, MD 21619
    102 Warbler Way Unit 2911, Chester, MD 21619
    /63

    $649,990 New Construction

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

    102 Warbler Way Unit 2911, Chester, MD 21619

    Welcome to the Magothy, 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

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2911, Chester, MD 21619
  • 719 Warbler Way, Chester, MD 21619
    719 Warbler Way, Chester, MD 21619
    719 Warbler Way, Chester, MD 21619
    /16

    $889,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,807 Sq Ft

    719 Warbler Way, Chester, MD 21619

    Polished kitchen with white cabinets & glass-front uppers. Vast island & quartz countertops for prep & dining. Welcoming great room featuring elegant fireplace. Screened patio with direct access to the great room. Charming dining area for mealtime enjoyment. Lavish primary suite & bath with dual vanities & feature wall. Private home office for leisure activities.

    K. Hovnanian Homes Builder
    719 Warbler Way, Chester, MD 21619
  • 110 Boatswain Way Unit 41, Chester, MD 21619
    110 Boatswain Way Unit 41, Chester, MD 21619
    110 Boatswain Way Unit 41, Chester, MD 21619
    /18

    $949,990 New Construction

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

    110 Boatswain Way Unit 41, Chester, MD 21619

    Welcoming foyer leads into open-concept living spaces. Gourmet kitchen featuring ample cabinetry & seamless connection to the dining area. Dry bar adds a stylish touch, ideal for hosting guests. Spacious great room highlighted by a cozy fireplace. Owner’s suite features a private sitting room & walk-in closet. Owner’s bath showcases a frameless shower door for a modern, elevated feel. Balcony

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 41, Chester, MD 21619
  • 110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    /28

    $799,990 New Construction

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

    110 Boatswain Way Unit 42, Chester, MD 21619

    Gourmet kitchen with designer cabinetry & vast center island. Inviting great room featuring a cozy electric fireplace. Dry bar creates a polished space for serving & entertaining. Peaceful owner's suite with stylish tray ceiling & private bath. Home office with double doors offers a quiet, flexible workspace. Balcony extends the living space outdoors for relaxing or unwinding.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 42, Chester, MD 21619
  • 110 Boatswain Way Unit 32, Chester, MD 21619
    110 Boatswain Way Unit 32, Chester, MD 21619
    110 Boatswain Way Unit 32, Chester, MD 21619
    /29

    $699,990 New Construction

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

    110 Boatswain Way Unit 32, Chester, MD 21619

    Gourmet kitchen with central island for prep & dining. Home office with double doors adds privacy & style. Dining area enhanced by a convenient dry bar. Great room centered around an electric fireplace. Balcony extends living space off the great room. Owner’s suite with private balcony access for relaxation. Spa-like owner’s bath with dual sinks & sleek finishes.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 32, Chester, MD 21619
  • 110 Boatswain Way Unit 31, Chester, MD 21619
    110 Boatswain Way Unit 31, Chester, MD 21619
    110 Boatswain Way Unit 31, Chester, MD 21619
    /21

    $849,990 New Construction

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

    110 Boatswain Way Unit 31, Chester, MD 21619

    Home office with double doors for privacy. Great room with an electric fireplace for warmth & charm. Large central island anchors the gourmet kitchen. Dry bar in dining area creates a perfect hosting space. Owner’s suite with a serene sitting room & balcony access. Dual walk-in closets for organized living. Owner’s bath with sleek dual sinks & spacious layout.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 31, Chester, MD 21619
  • 110 Boatswain Way Unit 21, Chester, MD 21619
    110 Boatswain Way Unit 21, Chester, MD 21619
    110 Boatswain Way Unit 21, Chester, MD 21619
    /21

    $749,990 New Construction

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

    110 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island. Dining area includes a convenient dry bar. Great room features an electric fireplace. Beautiful balcony extends off of the great room. Owner’s suite with dual walk-in closets. Private sitting room with balcony access. Luxurious owner’s bath with dual sinks.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 21, Chester, MD 21619
  • 110 Boatswain Way Unit 44, Chester, MD 21619
    110 Boatswain Way Unit 44, Chester, MD 21619
    110 Boatswain Way Unit 44, Chester, MD 21619
    /22

    $989,990 New Construction

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

    110 Boatswain Way Unit 44, Chester, MD 21619

    Open-concept kitchen, dining area, & great room designed for effortless flow. Gourmet kitchen with ample cabinetry for streamlined storage & prep. Dry bar creates a dedicated space for serving & display. Fireplace adds warmth & character to the great room. Owner’s suite with sitting room, walk-in closet & private bath. Frameless shower door delivers a sleek, spa-like touch in the owner’s bath.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 44, Chester, MD 21619
  • 121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    /42

    $1,099,990 New Construction

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

    121 Kinglet Ct, Chester, MD 21619

    Efficient kitchen featuring white cabinetry & quartz countertops. Open concept living area with vaulted ceiling & cozy fireplace. Pristine primary suite with stylish feature wall & ceiling treatment. Refreshing primary bath featuring a freestanding tub & brushed nickel finishes. Private Extra Suite & home office off foyer. Inviting screened patio for relaxing with friends. Attached 3-car tandem

    K. Hovnanian Homes Builder
    121 Kinglet Ct, Chester, MD 21619
  • 307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    /29

    $979,990 New Construction

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

    307 Kingfisher Ln, Chester, MD 21619

    Welcoming foyer leads to beautiful open concept floorplan. Inviting kitchen featuring white cabinetry, quartz countertops, & center island. Spacious great room with cozy fireplace, perfect for spending time with family. Tranquil primary suite featuring detailed ceiling treatment. Polished primary bath with brushed nickel finishes & generous walk-in closet. Convenient Extra Suite & home office off

    K. Hovnanian Homes Builder
    307 Kingfisher Ln, Chester, MD 21619
  • 110 Boatswain Way Unit 3041, Chester, MD 21619
    110 Boatswain Way Unit 3041, Chester, MD 21619
    110 Boatswain Way Unit 3041, Chester, MD 21619
    /44

    $949,990 New Construction

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

    110 Boatswain Way Unit 3041, 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 3041, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Anne's County Chester

Homes for Sale in a Senior Community in Chester, MD

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 201 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, MD over the last 12 months is $649,900, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$649,900
Median Single Family Sale Price
$682,450
Median Townhouse Sale Price
$380,000
Median 2 Bedroom Sale Price
$549,900
Median 1 Bedroom Sale Price
$294,500
Average Price Per Sq Ft
$298
Number of Homes for Sale
78
Last 12 months Home Sales
214
Months of Supply
4.40
Median List Price
$672,445
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
13%
How to Buy a Home How to Finance a Home How to Sell a Home

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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