Homes for Sale near Kent County High School

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  /60

  $1,495,000

  $155K PRICE DROP

  • 9 Beds
  • 6.5 Baths
  • 4,776 Sq Ft

  8796 Maryland Pkwy, Chestertown, MD 21620

  Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past

  Tracy Stone Coldwell Banker Chesapeake Real Estate Company

  8796 Maryland Pkwy, Chestertown, MD 21620
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  /54

  $425,000

  • 2 Beds
  • 1.5 Baths
  • 2,368 Sq Ft

  6202 Rock Hall Rd, Rock Hall, MD 21661

  This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance store—showcasing its adaptability for a wide range of business ventures. The second-floor

  William Sutton Coldwell Banker Chesapeake Real Estate Company

  6202 Rock Hall Rd, Rock Hall, MD 21661
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  /8

  $90,000

  • Land
  • 3.92 Acres
  • $22,959 per Acre

  0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

  Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. Enjoy the peace and quiet of the woods, with plenty of deer and wildlife all around. Buyer

  Maryn LeClair Chesapeake Real Estate Associates, LLC

  0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
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  /2

  $289,000

  • 1,874 Sq Ft

  31001 Chesterville Bridge Rd, Millington, MD 21651

  Bring your vision to this rare 15-acre property offering privacy, natural beauty, and endless possibilities. Mostly wooded with a picturesque pond, this property is an ideal setting for those seeking a private retreat, recreational getaway, or future homesite. An original structure dating back to 1980 remains on the property and includes a full basement. The condition existing home is believed

  Terri Murray RE/MAX Executive

  31001 Chesterville Bridge Rd, Millington, MD 21651
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  /70

  $1,495,000

  Coming Soon Sep 2

  • 5 Beds
  • 3.5 Baths
  • 2,620 Sq Ft

  23911 Kinnards Point Dr, Worton, MD 21678

  Discover the best of waterfront living in the sought-after community of Kinnairds Point. Set in a private, peaceful setting, this spacious home offers easy access to the water and a private dock on protected waters, with the Bay just around the corner.Thoughtfully designed for both everyday comfort and effortless entertaining, the home provides generous space for guests while maintaining

  Christopher McClary Gunther-McClary Real Estate

  23911 Kinnards Point Dr, Worton, MD 21678
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  /20

  $200,000

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  117 N Water St Unit 1B, Chestertown, MD 21620

  117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

  Liddy Campbell TTR Sotheby's International Realty

  117 N Water St Unit 1B, Chestertown, MD 21620
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  /2

  $15,000

  • Land
  • 1 Acre
  • $15,000 per Acre

  23741 L Rd, Chestertown, MD 21620

  Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

  Taylor Leaverton Benson & Mangold, LLC

  23741 L Rd, Chestertown, MD 21620
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  /34

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  896 Washington Ave, Chestertown, MD 21620

  A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

  Peter Heller Coldwell Banker Chesapeake Real Estate Company

  896 Washington Ave, Chestertown, MD 21620
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  /16

  $95,000

  • Land
  • 35,719 Sq Ft
  • $115,854 per Acre

  2 Sassafras Cove Rd, Galena, MD 21635

  Welcome to Wilson Point Estates! A 14 Lot Custom Home Eastern Shore Community. Designed for those who value craftsmanship and intention, Wilson Point Estates is not a production neighborhood, it’s a place where each home is purposefully designed to complement the character of the Shore. Picture gracious porches, elevated coastal details, and interiors tailored to how you truly live, entertain,

  Jenyne Ward Patterson-Schwartz-Middletown

  2 Sassafras Cove Rd, Galena, MD 21635
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  /2

  $38,000

  $23K PRICE INCREASE

  • Land
  • 14,810 Sq Ft
  • $111,765 per Acre

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

  Dee Dee Miller Paul Wesley Real Estate

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
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  /26

  $399,000

  Open Sun 12PM - 2PM $81K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,156 Sq Ft

  11944 Augustine Herman Hwy, Kennedyville, MD 21645

  Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences.From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying

  William Sutton Coldwell Banker Chesapeake Real Estate Company

  11944 Augustine Herman Hwy, Kennedyville, MD 21645
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  /29

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  21336 Haven Rd, Rock Hall, MD 21661

  UPDATE - New carpet just installed! Convenient one-level living in this 3BR, 2.5 bath rancher. The house has a desirable split bedroom layout with the primary bedroom, bath & closet off the kitchen and two bedrooms and another full bath off the other side of the house. The sun room has a propane stove and exits to a 12' x 15' deck. There's a 10' x 16' shed. Nice quiet, in-town location.

  Cindy Genther Rock Hall Properties Real Estate

  21336 Haven Rd, Rock Hall, MD 21661
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  /3

  $125,000

  • Land
  • 32,670 Sq Ft
  • $166,667 per Acre

  4 Wilson Point Rd, Galena, MD 21635

  Welcome to Wilson Point Estates – Nestled in a peaceful, secluded setting, this exclusive community offers 14 generously sized lots with No Builder Tie-In but developer must approve the architectural appearance of the home. With each lot carefully placed to preserve the natural beauty and privacy of the landscape, Every residence will reflect quality craftsmanship, offering both comfort and style

  Aaron Clark Patterson-Schwartz-Middletown

  4 Wilson Point Rd, Galena, MD 21635
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  /14

  $265,000

  $34K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  11060 Plum Dr, Worton, MD 21678

  Discover this beautiful 3-bedroom Cape Cod home in the heart of Worton, Maryland, conveniently located near local amenities and scenic Eastern Shore attractions. Thoughtfully updated with over $20,000 in upgrades, this residence effortlessly blends classic charm with modern comfort.The inviting living spaces feature abundant natural light and elegant finishes throughout. The upgraded

  ALICE BENNETT Patterson-Schwartz-Newark

  11060 Plum Dr, Worton, MD 21678
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  /43

  $100,000

  $25K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,896 Sq Ft

  10520 Worton Rd, Worton, MD 21678

  ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/15/2026, 10:00 AM. Bidding ends 9/17/2026, 12:40 PM. The list price is the suggested opening bid. Deposit: $15,000.This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Maryland’s Eastern Shore in Kent

  Adam Shpritz Ashland Auction Group LLC

  10520 Worton Rd, Worton, MD 21678
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  /20

  $324,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,216 Sq Ft

  9126 Fairlee Rd, Chestertown, MD 21620

  Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living.

  Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

  9126 Fairlee Rd, Chestertown, MD 21620

Showing Results 201 - 216, Page 6 of 6