Kent County MD Houses for Sale

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  $295,000

  • 4 Beds
  • 2 Baths
  • 1,000 Sq Ft

  6374 Rock Hall Rd, Rock Hall, MD 21661

  Looking for your first place or a weekend stay to enjoy Marylands beautiful eastern shore, look no more! Located just outside of Rock Hall, this charming ranch-style residence offers the convenience of one-level living, perfectly situated on a spacious, treed lot just minutes from downtown. Recently remodeled from top to bottom, this home features sleek stainless steel appliances, stunning

  Dee Dee Miller Long & Foster Real Estate, Inc.

  6374 Rock Hall Rd, Rock Hall, MD 21661
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  /52

  $1,395,500

  • 5 Beds
  • 4.5 Baths
  • 3,243 Sq Ft

  105 High St, Chestertown, MD 21620

  Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored Second Empire home on Chestertown Historic District’s most prominent corner. Water views are appreciated from two sides. Great balance of modern amenities and layout matched with historic design elements and style. The builders who took on this passion project are some of

  Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  105 High St, Chestertown, MD 21620
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  /46

  $5,900,000

  • 6 Beds
  • 4.5 Baths
  • 4,214 Sq Ft

  5135 Crosby Rd, Rock Hall, MD 21661

  A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas

  Courtney Chipouras TTR Sotheby's International Realty

  5135 Crosby Rd, Rock Hall, MD 21661
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  /43

  $5,900,000

  • 6 Beds
  • 4.5 Baths
  • 4,214 Sq Ft

  5135 Crosby Rd, Rock Hall, MD 21661

  A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas

  Courtney Chipouras TTR Sotheby's International Realty

  5135 Crosby Rd, Rock Hall, MD 21661
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  /16

  $232,000

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  21217 Texas Ave, Chestertown, MD 21620

  MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, flooring recently upgraded, beautifully tiled bathroom, Pergo wood flooring. Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings fireplace, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The

  Terry Catalano RE/MAX Leading Edge

  21217 Texas Ave, Chestertown, MD 21620
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  /78

  $184,000

  • 2 Beds
  • 1 Bath
  • 658 Sq Ft

  1 Kent Dr, Betterton, MD 21610

  Charming Bungalow by the Bay!Discover the perfect coastal retreat in this delightful 2-bedroom bungalow, just one block from the beach! Nestled in a quaint town of only 283 residents, this home boasts beautiful hardwood ceilings, a screened front porch for relaxing evenings, and spacious back and side decks ideal for outdoor entertaining. The lower-level laundry and ample storage provide

  Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  1 Kent Dr, Betterton, MD 21610
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  /6

  $1,800,000

  • 7 Beds
  • 6.5 Baths
  • 12,520 Sq Ft

  6520 Swan Creek Rd, Rock Hall, MD 21661

  The owner is offering a rare opportunity to subdivide and purchase a spectacular 20-acre waterfront parcel. Renovate the 12,520-square-foot residence, designed by renowned architect Paul Rudolph, and create a breathtaking waterfront estate with panoramic views—just steps from the Chesapeake Bay. An acceptable offer will be contingent upon completion of the subdivision at the buyer's expense. The

  Deborah Laggini Long & Foster Real Estate, Inc.

  6520 Swan Creek Rd, Rock Hall, MD 21661
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  $4,850,000

  • 5 Beds
  • 8 Baths
  • 9,852 Sq Ft

  23620 Lands End Rd, Chestertown, MD 21620

  80 private acres beautifully situated on the highly prized Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. One of only 4 properties on Orchard Point and sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to

  Richard Keaveney Cross Street Realtors LLC

  23620 Lands End Rd, Chestertown, MD 21620
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  /22

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft

  866 Washington Ave, Chestertown, MD 21620

  Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use

  Jeff Guthrie Cross Street Realtors LLC

  866 Washington Ave, Chestertown, MD 21620
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  /36

  $1,165,000

  • 5 Beds
  • 3.5 Baths
  • 2,174 Sq Ft

  4938 Huntingfield Rd, Rock Hall, MD 21661

  Nestled on .83 acres, this captivating Chesapeake Bay waterfront home offers the perfect blend of comfort and coastal charm just outside of Rock Hall. The property includes a 3-bedroom plus bonus room, 2 1/2-bath main house and a detached garage with a 1-bedroom, 1-bath efficiency apartment, ideal for guests or potential rental use. Step inside to be welcomed by a stunning wall of windows

  Courtney Chipouras TTR Sotheby's International Realty

  4938 Huntingfield Rd, Rock Hall, MD 21661
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  /67

  $659,000

  • 4 Beds
  • 3.5 Baths
  • 3,684 Sq Ft

  11040 Kylie Ln, Chestertown, MD 21620

  Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and

  Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  11040 Kylie Ln, Chestertown, MD 21620
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  /65

  $899,900

  • 4 Beds
  • 2 Baths
  • 2,880 Sq Ft

  21 6th Ave, Betterton, MD 21610

  This incredibly private retreat property is situated on 9+ acres in Northern Kent County Maryland overlooking it's own private lake loaded with record size fish and includes a nearly new 2800+/- sq. foot home built in 2020, two detached 3-bay metal shop buildings, and a vast variety of native wildlife including bald eagles, herons, turkeys, deer, and multiple waterfowl species. The home itself

  William Norris Select Land & Homes, LLC

  21 6th Ave, Betterton, MD 21610
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  /25

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,326 Sq Ft

  5686 S Main St, Rock Hall, MD 21661

  Sweet corner property in downtown Rock Hall, right on the "parade route," and just two blocks from the Rock Hall Harbor/ Chesapeake Bay. Welcoming home with a first floor primary bedroom, and large living room with a woodstove. There is a formal dining room, or you could enjoy meals outside in the fenced in back yard! Upstairs offers two more bedrooms, a full bath and an additional room, perfect

  Lynn Hilfiker Gunther-McClary Real Estate

  5686 S Main St, Rock Hall, MD 21661
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  /46

  $230,000

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft

  26670 Maple Ave, Still Pond, MD 21667

  The listing includes 26670 Maple Avenue with a 1920 dwelling of 2024 SF on .54 acre of land as well as 26680 Maple Avenue dwelling of 1680 SF on .624 acre of land and a parcel of land 100 X 160. Both homes are in need of major repair; however, one will find potential. Final perc information for sewage system will be provided by Kent County Health Department when water table is acceptable which

  Debbie Meikle Doug Ashley Realtors, LLC

  26670 Maple Ave, Still Pond, MD 21667
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  /23

  $319,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  4921 Piney Neck Rd, Rock Hall, MD 21661

  Welcome to your new home in the historic harbor town of Rock Hall! Quality new construction built with meticulous attention to detail. This 3 bedroom/2 bath home is clean and sleek with modern, tasteful upgrades and color palette. Every appliance and ammenity is brand new, from the HVAC to the bathroom vanities and recessed lighting. Any chef would be thrilled with this substantial kitchen

  Andy Batch Keller Williams Select Realtors of Annapolis

  4921 Piney Neck Rd, Rock Hall, MD 21661
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  /4

  $325,000 Coming Soon

  • 1 Bed
  • 1.5 Baths
  • 936 Sq Ft

  108 S Kent St, Chestertown, MD 21620

  Cute as a button in the historic district on South Kent St. This 1 bedroom, 1.5 bath home is in the center of town within walking distance to the farmers market and all the shops and restaurants. There is potential for a second bedroom upstairs if you add a wall between the bedroom and the sitting area. Adorable backyard. Perfect for one or two people as a full-time residence or weekend getaway.

  Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  108 S Kent St, Chestertown, MD 21620
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  $345,000 Coming Soon

  • 3 Beds
  • 3 Baths
  • 1,872 Sq Ft

  127 Cedarwood Dr, Galena, MD 21635

  Welcome to 127 Cedarwood Drive a charming and spacious Cape Cod-style home nestled on a beautifully landscaped corner lot in the desirable Dogwood Village community of Galena. This well-maintained 3-bedroom, 3-bathroom home offers over 1,800 square feet of comfortable living space and a full partially finished basement perfect for future expansion, storage, or recreational use.Step

  Dottie Walker Empower Real Estate, LLC

  127 Cedarwood Dr, Galena, MD 21635
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  /3

  $199,900 Coming Soon

  • 2 Beds
  • 1 Bath
  • 1,296 Sq Ft

  234 N College Ave, Chestertown, MD 21620

  Investor Special – Charming Colonial in Prime Chestertown Location!Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation

  Anastasia Zivkovic Cummings & Co. Realtors

  234 N College Ave, Chestertown, MD 21620
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  /16

  $110,000

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft

  11054 Austin Ln, Worton, MD 21678

  ONLINE AUCTION: Bidding begins 8/6/2025 @ 10:00 AM. Bidding ends 8/8/2025 @ 12:30 PM. List Price is Suggested Opening Bid. Deposit: $20,000. Single Family Home located in the Knights Landing area of Kent County, MD. JUST MINUTES to the many attractions of the Chestertown area. Easy access to major traffic artery Lambs Meadow Rd. Property is occupied.

  Adam Shpritz Ashland Auction Group LLC

  11054 Austin Ln, Worton, MD 21678

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