35

Chester, MD 1-Story Homes for Sale

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  • /62

    $530,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - $10,000 Closing Cost Assistance Available - Turn Key & 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

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 936-3917

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • /74

    $499,000

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

    170 Harrier Way Unit 11, Chester, MD 21619

    ***Redfin powered by Rocket Mortgage Preferred Pricing*** Enjoy with a 1% lower interest rate for your initial year or potential savings of up to $6,000 on your closing costs when you finance with Rocket Mortgage*** Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent

    Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
  • /24

    $659,900 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
  • /10

    $740,900 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
  • /12

    $474,990 New Construction

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

    Magothy, 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

    K Hovnanian's Four Seasons

    Magothy, Chester, MD 21619
  • /27

    $844,900 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
  • /56

    $950,000

    • 4 Beds
    • 4 Baths
    • 3,450 Sq Ft

    255 Sailcloth Way, Chester, MD 21619

    COMING SOON - The Double Primary Bedroom Santorini model with 3,500 sq ft that everyone loves, perfectly situated on a cul de sac lot with a long list of upgrades including the gourmet kitchen, luxury baths in BOTH primary bedrooms, the loft with full bath and sky basement, Screened porch and so much more! This is perfect for multi-generational living! Four Seasons on Kent Island is a resort

    Kathleen Higginbotham Keller Williams Flagship

    255 Sailcloth Way, Chester, MD 21619
  • /47

    $619,900

    • 2 Beds
    • 2 Baths
    • 1,913 Sq Ft

    224 Bayberry Dr, Chester, MD 21619

    Discover the charm of this meticulously maintained, one-owner Donegal model nestled in the highly desirable, water-privileged 55+ community of Four Seasons at Kent Island. This stunning single-family home features an expansive open-concept layout, enhanced with designer lighting and custom finishes that elevate the home's ambiance.Step into a spacious kitchen that serves as the heart of

    Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
  • /45

    $639,500

    • 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
  • /28

    $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
  • /32

    $779,900 New Construction

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

    121 Wheelhouse Way, Chester, MD 21619

    Charming gourmet kitchen featuring designer cabinets & center island.Connected dining area & great room for seamless flow.Convenient dry bar & electric firepelace in main living spaces.Peaceful owner's suite & bath with walk-in closet.Organized home office for leisure activities.Versatile balcony for outdoor enjoyment.

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • /18

    $719,900 New Construction

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

    121 Wheelhouse Way, Chester, MD 21619

    Beautiful gourmet kitchen overlooks open concept living spaces.Spacious great room with warm fireplace.Sun-lit dining area with drybar, perfect for hosting dinner parties.Lavish owner's suite & bath featuring dual walk-in closets & sitting room.Convenient laundry room located near secondary bedrooms.Lovely balcony for outdoor relaxation.

    K Hovnanian's Four Seasons

    Severn, Chester, MD 21619
  • /58

    $784,900 New Construction

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

    201 Switchgrass Way Unit 1443, Chester, MD 21619

    Welcome home to the Chester, a beautifully crafted 2-bedroom, 2.5-bath residence with a 1-car garage, offering low-maintenance luxury and stylish finishes throughout. Ideal for full-time living or a lock-and-leave lifestyle, this home delivers comfort, flexibility, and charm in every room.Inside, you’ll find a dedicated home office with lighted French doors, perfect for remote work or a

    Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1443, Chester, MD 21619
  • /58

    $784,900 New Construction

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

    201 Switchgrass Way Unit 1442, Chester, MD 21619

    Experience the perfect balance of function and finesse in the Chester, a 2-bedroom, 2.5-bath home with a 1-car garage, designed for effortless living and elevated comfort.Thoughtfully laid out, this home includes a stylish home office with lighted French doors, a dry bar for entertaining, and a welcoming electric fireplace to anchor the living space. Elegant tray ceilings in both the great room

    Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1442, Chester, MD 21619
  • /21

    $559,990 New Construction

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

    Severn, 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's Four Seasons

    Severn, Chester, MD 21619
  • /11

    $762,900 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
  • /12

    $626,900 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
  • /33

    $474,990 New Construction

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

    Chester, 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

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • /81

    $739,950 New Construction

    • 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
  • /26

    $510,000

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft

    1872 Harbor Dr, Chester, MD 21619

    1872 Harbor Drive, Chester, MD in the Sought-After Harbor View CommunityPremium Corner Lot | Nearly 3⁄4 Acre | Renovated Brick RancherLocated in the established Harbor View neighborhood, this fully renovated brick rancher sits on a rare, oversized corner lot—nearly three-quarters of an acre made up of two parcels. The expanded lot offers flexibility for future additions, such as an

    Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • /19

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1906 Harbor Dr, Chester, MD 21619

    Great opportunity for a savvy investor to buy way below market value. This 3 brm 2 ba rancher, can easily be converted to a 4 brm. Needs work! Sold Strictly AS IS. Seller never occupied the property, therefore cannot guarantee accuracy in this listing, especially regarding utilities, well and sewer. Buyer must do their own due diligence before submitting an offer.

    Alex Fox Allfirst Realty, Inc.

    1906 Harbor Dr, Chester, MD 21619
  • /22

    $393,000

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    1838 Sherman Dr, Chester, MD 21619

    Nestled in the heart of Chester, Maryland on the beautiful Eastern Shore, this charming single-story rancher offers the perfect blend of comfort, charm, and convenience. Set on a spacious, fully fenced lot, this home provides a serene retreat with plenty of outdoor space to relax or entertain.Step inside to find a bright and inviting interior with tasteful neutral tones, modern finishes, and a

    Kara Shaffer Engel & Völkers Annapolis

    1838 Sherman Dr, Chester, MD 21619
  • /31

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,795 Sq Ft

    307 Skipper Ln, Chester, MD 21619

    Welcome to Your Refreshing New Home with First-Floor Living! This beautifully updated residence offers the perfect blend of comfort and convenience with three spacious bedrooms and two full baths, all on the main level. The expansive primary suite features a private, fully updated bath for your relaxation. The gorgeous kitchen is a true standout, boasting quartz countertops, brand new stainless

    Dee Dee McCracken Coldwell Banker Realty

    307 Skipper Ln, Chester, MD 21619
  • /73

    $510,000

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

    170 Harrier Way Unit 22, Chester, MD 21619

    For a limited time, $4000 credit towards Capital Contribution Fee for full price offer.When I asked the seller what is the best part of living here, she said......"the best things about my place is the balcony and view !! Unobstructed. No buildings directly between my unit and the river". Easy place to live !! Lock the door and leave everything to someone else !!

    Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, Chester, MD 21619
  • /26

    $499,000

    • 2 Beds
    • 2 Baths

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Priced to Sell! Seller is ready for their next adventure! Move in, in May! Enjoy low-maintenance living in the amenity-rich, 55+ community of Four Seasons on Kent Island. This 2-bedroom, 2-bath home offers comfortable one-level living with an open layout, perfect for entertaining or relaxing. The property includes a 1-car garage with additional storage units—ideal for keeping your home organized

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • /59

    $498,000

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

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. With 1900 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, 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

    $334,900

    • 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
  • /27

    $469,900

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1340 Queen Anne Dr, Chester, MD 21619

    Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • /10

    $541,900 New Construction

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

    121 Wheelhouse Way, Chester, MD 21619

    Efficient gourmet kitchen featuring vast center island & designer cabinets.Cozy electric fireplace adds character & warmth to great room.Refined dining area featuring convenient dry bar.Lavish owner's suite & spa bath with walk-in closet.Productive home office with double doors.Inviting covered patio for relaxing outdoors.

    K Hovnanian's Four Seasons

    Magothy, Chester, MD 21619
  • /45

    $999,900 New Construction

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

    327 Kingfisher Ln, Chester, MD 21619

    Welcome to the Tuscaloosa, a stunning 5-bedroom, 4.5-bath home designed for flexible living and modern style. With a 3-car garage, open-concept layout, and high-end finishes, this home is the perfect blend of comfort and sophistication.Enjoy thoughtful details throughout, including a cozy fireplace, versatile home office, bright loft, and a relaxing screened patio. The kitchen features a full

    Mary Anne Kowalewski KOVO Realty

    327 Kingfisher Ln, Chester, MD 21619
  • /24

    $684,900 New Construction

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

    201 Switchgrass Way, Chester, MD 21619

    Gourmet kitchen with wall oven & spacious central island.Dry bar in the dining area adds a stylish touch.Great room features an electric fireplace for cozy evenings.Sliding doors open to a private balcony off the great room.Owner’s suite with direct balcony access for fresh air.Dual vanities in the spa-inspired owner’s bath.Thoughtfully designed layout with

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • /25

    $784,900 New Construction

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

    201 Switchgrass Way, Chester, MD 21619

    Private home office with double doors for a quiet workspace.Central island anchors the gourmet kitchen with wall oven.Great room with a warm electric fireplace & balcony access.Dining area includes a dry bar, perfect for hosting.Owner’s suite offers a retreat with private balcony entry.Spa-like owner’s bath with dual vanities & modern

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • /25

    $784,900 New Construction

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

    201 Switchgrass Way, Chester, MD 21619

    Home office with elegant double-door entry.Gourmet kitchen with wall oven & oversized island.Dining area includes a built-in dry bar for entertaining.Great room with an electric fireplace & natural light.Access to the balcony from both the great room & owner’s suite.Dual vanities in the owner’s spa bath for a luxe feel.Smartly designed floorplan

    K Hovnanian's Four Seasons

    Chester, Chester, MD 21619
  • /19

    $739,900 New Construction

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

    211 Switchgrass Way, 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's Four Seasons

    Severn, Chester, MD 21619

Home Trends in Chester, MD

Housing Trends

Median Sale Price
$562,500
Median Single Family Sale Price
$610,000
Median Townhouse Sale Price
$424,875
Median 2 Bedroom Sale Price
$499,000
Median 1 Bedroom Sale Price
$296,500
Average Price Per Sq Ft
$293
Number of Homes for Sale
73
Last 12 months Home Sales
165
Months of Supply
5.30
Median List Price
$560,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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