5,132

Chester, MD Homes

Section Image Section Image Section Image
  • /40

    $659,000 Under Contract

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    132 Claiborne St, Chester, MD 21619

    Discover exceptional living on an oversized fenced lot in the sought-after community of Gibson’s Grant on Kent Island. This beautifully maintained home offers a rare combination of space, versatility, and thoughtful upgrades—inside and out. A welcoming front porch overlooks a peaceful community green space, setting the tone for the charm found throughout. Step inside to hardwood floors spanning

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 490-0332

    132 Claiborne St, Chester, MD 21619
  • /2

    $1,750 per month

    • 1 Bed
    • 1 Bath
    • 640 Sq Ft
    • Townhouse for Rent

    26D Queen Anne Way, Chester, MD 21619

    Super Cute Condo in popular Queen's Landing with views of the pond from your private back patio. Laundry in unit and 2 storage closets on patio along with convenient parking. Community features pool, tennis, fitness, walking paths, and access to cross island trail as well as restaurants and local marinas.

    26D Queen Anne Way, Chester, MD 21619
  • /106

    $630,000 Sold Oct 30, 2025

    204 Skipper Ln, Chester, MD 21619

    • 6 Beds
    • 3 Baths
    • 3,760 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Below List Price
    • $168/SF
    • 40 Days On Market

    Last Listing Agent Andy Schweigman Douglas Realty, LLC

    204 Skipper Ln, Chester, MD 21619
    • /23

      Est $290,740 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,080 Sq Ft

      1823 Chester Dr, Chester, MD 21619

      1823 Chester Dr, Chester, MD 21619
  • /41

    $869,000

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft

    162 Kirwans Landing Ln, Chester, MD 21619

    BIG PRICE IMPROVEMENT. Private Waterfront Living in Kirwans Landing!Nestled on 1.4 acres in the water-privileged community of Kirwans Landing, this property offers the perfect blend of privacy, comfort, and resort-style outdoor living. Step outside to your own outdoor oasis, complete with a saltwater pool, spacious deck, and beautifully hardscaped patio surrounded by mature landscaping. A

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 941-2361

    162 Kirwans Landing Ln, Chester, MD 21619
  • /18

    $2,150 per month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Condo for Rent

    214 Teal Ct Unit G, Chester, MD 21619

    Water Views! 2-bedroom 2-bathroom 1,200 sqft condo ready for a new tenant. Primary bedroom has connecting full bathroom and walk in closet. Living room, dining room & all bedrooms have water views. Stainless steel appliances, balcony with water views and full-size washer & dryer. All carpeting has been updated. Walking distance to local restaurants and close proximity to shopping and the Kent

    John Freeman Coldwell Banker Realty

    214 Teal Ct Unit G, Chester, MD 21619
  • /55

    $989,000 Sold Sep 11, 2025

    330 Macum Creek Dr, Chester, MD 21619

    • 4 Beds
    • 3.5 Baths
    • 3,949 Sq Ft
    • Built 2015

    Last Sold Summary

    • $250/SF
    • 27 Days On Market

    Current Estimated Value $978,434

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    330 Macum Creek Dr, Chester, MD 21619
    • /73

      Est $626,336 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,096 Sq Ft

      104 Sunset Dr, Chester, MD 21619

      104 Sunset Dr, Chester, MD 21619
  • /47

    $435,000 Under Contract

    • 4 Beds
    • 2 Baths
    • 1,980 Sq Ft

    1701 Bayside Dr, Chester, MD 21619

    Welcome to 1701 Bayside Dr, a beautifully updated rancher offering direct, unobstructed waterviews of Crab Alley Bay. The main home features 3 bedrooms and 1 full bath, highlighted by LVP flooring throughout, a gorgeous updated kitchen with granite countertops, and spacious living and family rooms—each with water views. The primary bedroom is generously sized with two closets. Two generously

    Agent Photo

    Charlotte Savoy

    The KW Collective

    (410) 936-3989

    1701 Bayside Dr, Chester, MD 21619
  • /30

    $2,800 per month

    • 3 Beds
    • 2.5 Baths
    • 1,778 Sq Ft
    • House for Rent

    318 Hanna Ct, Chester, MD 21619

    Great location in established neighborhood of Clayborne Woods. New roof. Newer paint and carpet. Kitchen with breakfast nook, newer appliances and granite countertops, including a gas stove. Large room sizes, 9'ceilings, family room and separate living room. First floor primary bedroom with walk in closet, jetted tub, double vanity, and vaulted ceiling with ceiling fan. Powder room on main level.

    Penny Hope Long & Foster Real Estate, Inc.

    318 Hanna Ct, Chester, MD 21619
  • /52

    $553,000 Sold Apr 30, 2025

    1106 Cox Neck Rd, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,646 Sq Ft
    • Built 1975

    Last Sold Summary

    • $209/SF
    • 53 Days On Market

    Current Estimated Value $559,193

    Last Listing Agent April Heim Rosendale Realty

    1106 Cox Neck Rd, Chester, MD 21619
    • /28

      Est $343,143 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,280 Sq Ft

      29H Queen Mary Ct, Chester, MD 21619

      29H Queen Mary Ct, Chester, MD 21619
  • /44

    $549,000 Under Contract

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft

    47 D Queen Anne Way, Chester, MD 21619

    Accepting backup contracts! Enjoy resort style living every day in the gorgeous waterfront condo. Watch the sun & moon rise as you sip your favorite beverage. This sought after townhome/condo has extensive view of the Chester River & Eastern Neck Island. The owner has updated & made this place like no other. Soundproof quiet rock, custom barn doors throughout, gourmet kitchen with granite

    Agent Photo

    Brenda Fornos

    Taylor Properties

    (410) 623-7650

    47 D Queen Anne Way, Chester, MD 21619
  • /54

    $3,950 per month

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft
    • House for Rent

    1606 Howard Rd, Chester, MD 21619

    Welcome to Crab Alley Bay, Chester, MDThis cherished waterfront home offers one of the most captivating settings on the Eastern Shore—perched on a point with sweeping 270-degree panoramic views of Crab Alley Bay. Resting on approximately three-quarters of an acre, the property is as peaceful and restorative as it is beautiful, providing a rare opportunity to enjoy true waterfront

    Lisa Barton Coldwell Banker Realty

    1606 Howard Rd, Chester, MD 21619
  • /53

    $475,000 Sold Sep 29, 2025

    203 Barren Ridge Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 2,072 Sq Ft
    • Built 1988

    Last Sold Summary

    • $229/SF
    • 38 Days On Market

    Last Listing Agent Beth Bearinger Keller Williams Gateway LLC

    203 Barren Ridge Rd, Chester, MD 21619
    • /48

      Est $357,184 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,747 Sq Ft

      307 Schooner Way Unit 42, Chester, MD 21619

      307 Schooner Way Unit 42, Chester, MD 21619
  • /81

    $814,900

    • 3 Beds
    • 3 Baths
    • 2,399 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

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset Ln, Chester, MD 21619
  • /2

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,222 Sq Ft
    • House for Rent

    1820 Chester Dr, Chester, MD 21619

    3 bedroom 2 bath ranch style home in Harbor View community. Deck off eat in kitchen, large yard, with a section fenced off. New shed being installed in back corner. Long driveway with room for 4 vehicles. Freshly painted and cleaned. Will be ready for November 1st. Close to all amenities that Kent Island provides. Easy on off of Rt. 50. Just minutes from the Bay Bridge.

    Cindy Jacobs Maryland Residential Management Co

    1820 Chester Dr, Chester, MD 21619
  • /43

    $1,025,000 Sold Nov 26, 2025

    318 Old Point Rd, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,656 Sq Ft
    • Built 2024

    Last Sold Summary

    • $619/SF
    • 6 Days On Market

    Last Listing Agent Annie Eaton Coldwell Banker Realty

    318 Old Point Rd, Chester, MD 21619
    • /81

      Est $796,469 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,771 Sq Ft

      136 Evelyne St, Chester, MD 21619

      136 Evelyne St, Chester, MD 21619
  • /51

    $599,900 Pending

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

    224 Bayberry Dr, Chester, MD 21619

    Welcome to Easy Living on the Eastern Shore! ***Discover the perfect blend of comfort, style, and resort-style living in this impeccably maintained, one-owner home — tucked into the highly sought-after, water-privileged 55+ community of Four Seasons at Kent Island.From the moment you walk in, you’ll notice the difference. The open-concept floor plan is thoughtfully designed and

    Agent Photo

    Petra Quinn

    Realty Navigator

    (410) 505-7792

    224 Bayberry Dr, Chester, MD 21619
  • /46

    $350,000 Sold Apr 04, 2025

    1833 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,024 Sq Ft
    • Built 1986

    Last Sold Summary

    • $342/SF
    • 106 Days On Market

    Current Estimated Value $352,787

    Last Listing Agent Janice O'Donnell Chaney Homes, LLC

    1833 Harbor Dr, Chester, MD 21619
    • /79

      Est $844,007 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,901 Sq Ft

      316 Macum Creek Dr, Chester, MD 21619

      316 Macum Creek Dr, Chester, MD 21619
  • /12

    $489,990 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
  • /76

    $784,900 Sold Jan 20, 2025

    230 Switchgrass Way Unit 1341, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2024

    Last Sold Summary

    • $302/SF
    • 21 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    230 Switchgrass Way Unit 1341, Chester, MD 21619
    • /44

      Est $853,371 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,225 Sq Ft

      326 Thomas White Blvd, Chester, MD 21619

      326 Thomas White Blvd, Chester, MD 21619
  • /26

    $818,900 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
  • /88

    $624,900 Sold Sep 19, 2025

    211 Switchgrass Way Unit 1524, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2024

    Last Sold Summary

    • $240/SF
    • 147 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1524, Chester, MD 21619
    • /46

      Est $612,003 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,824 Sq Ft

      163 Claiborne St, Chester, MD 21619

      163 Claiborne St, Chester, MD 21619
  • /40

    $847,900 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
  • /52

    $365,000 Sold Mar 25, 2025

    6004 Bridgepointe Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,885 Sq Ft
    • Built 1992

    Last Sold Summary

    • $194/SF
    • 26 Days On Market

    Current Estimated Value $367,206

    Last Listing Agent Kathleen Higginbotham Keller Williams Flagship

    6004 Bridgepointe Dr, Chester, MD 21619
    • /38

      Est $690,231 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,320 Sq Ft

      121 Henry Stoupe Way, Chester, MD 21619

      121 Henry Stoupe Way, Chester, MD 21619
  • /71

    $499,000 Pending

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

    170 Harrier Way Unit 11, Chester, MD 21619

    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 Island! Completely move-in ready, this home boasts a gourmet kitchen, a formal dining area, and a cozy family room, all enhanced by luxurious finishes throughout. The spacious primary bedroom features a full ensuite bath, while

    Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
  • /30

    $465,000 Sold Jun 10, 2025

    1713 Bayside Dr, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft
    • Built 1972

    Last Sold Summary

    • $235/SF
    • 42 Days On Market

    Current Estimated Value $487,836

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    1713 Bayside Dr, Chester, MD 21619
    • /60

      Est $593,635 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,240 Sq Ft

      215 John Gibson Dr, Chester, MD 21619

      215 John Gibson Dr, Chester, MD 21619
  • /24

    $668,900 New Construction

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

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - 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
  • /42

    $649,900 Sold Apr 24, 2025

    228 Warbler Way, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft
    • Built 2024

    Last Sold Summary

    • $233/SF
    • 9 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    228 Warbler Way, Chester, MD 21619
    • /70

      Est $733,627 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,148 Sq Ft

      147 Carriage Heath, Chester, MD 21619

      147 Carriage Heath, Chester, MD 21619
  • /27

    $858,900 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
  • /40

    $540,656 Sold Sep 19, 2025

    112 Harbour Sound Dr, Chester, MD 21619

    • 2 Beds
    • 3.5 Baths
    • 2,131 Sq Ft
    • Built 1989

    Last Sold Summary

    • $254/SF
    • 86 Days On Market

    Last Listing Agent Carlos Larraz Annapolis Properties LLC

    112 Harbour Sound Dr, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 18

Home Trends in Chester, MD

Housing Trends

Median Sale Price
$634,900
Median Single Family Sale Price
$649,900
Median Townhouse Sale Price
$365,000
Median 2 Bedroom Sale Price
$540,328
Median 1 Bedroom Sale Price
$320,000
Average Price Per Sq Ft
$293
Number of Homes for Sale
63
Last 12 months Home Sales
188
Months of Supply
4.00
Median List Price
$644,990
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
How to Buy a Home How to Finance a Home How to Sell a Home