Homes for Sale near Kent County High School

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  /20

  $157,400

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft

  132 Prospect St, Chestertown, MD 21620

  Beautifully Remodeled Two-Level Colonial Offering Timeless Charm and Modern Comfort. This home features a Brand New Kitchen with New Cabinets (2026), Quartz Counters, Stainless Steel Appliances (2026), and a Stylish Tile Backsplash. Enjoy Fully Updated Bathrooms, New Flooring Throughout, and Spacious Bedrooms Filled With Natural Light. New Modern Lighting (2026) and Fresh Custom Paint enhance the

  Matthew Altizer ANR Realty, LLC

  132 Prospect St, Chestertown, MD 21620
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  /39

  $299,500 Open Sat 11AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 1,867 Sq Ft

  108 Oak Leaf Dr, Chestertown, MD 21620

  This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location provides additional natural light, creating a bright and inviting atmosphere throughout. The home has been freshly painted and features brand-new carpeting, while the ceramic tile and hardwood flooring in other areas are in

  Grace Crockett Doug Ashley Realtors, LLC

  108 Oak Leaf Dr, Chestertown, MD 21620
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  /4

  $1,250,000

  • Land
  • 86 Acres
  • $14,535 per Acre

  Lot 1 Carroll Clark Rd, Galena, MD 21635

  Lot 1 is +/- 86 acres of prime development land in Kent County's Rt. 301 Growth Corridor. With +2,500 ft along Rt. 301 and 1,295 ft along Carroll Clark Rd, this property offers easy access to Middletown, DE and Rt. 1. The property is zoned Employment Center and qualifies for Kent County and Maryland State incentives. Approximately 46 acres are currently in ag use. There is a cell tower on the

  Cindy Genther Rock Hall Properties Real Estate

  Lot 1 Carroll Clark Rd, Galena, MD 21635
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  /2

  $58,000

  • Land
  • 1 Acre
  • $58,000 per Acre

  11729 Saint James Newtown Rd, Worton, MD 21678

  Dee Dee Miller Long & Foster Real Estate, Inc.

  11729 Saint James Newtown Rd, Worton, MD 21678
• 

  

  

  /4

  $50,000

  • Land
  • 37,026 Sq Ft
  • $58,824 per Acre

  0 Walnut St, Rock Hall, MD 21661

  This listing is for the sale of parcel 504, a 0.85 ac property off Walnut St in the town of Rock Hall. A buyer should confirm buildability and availability of public water and sewer.

  Cindy Genther Rock Hall Properties Real Estate

  0 Walnut St, Rock Hall, MD 21661
• 

  

  /43

  $399,000

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft

  6416 Edesville Rd, Rock Hall, MD 21661

  Completely renovated from the studs up, this beautifully updated 3-story home offers 2,200 square feet of thoughtfully designed living space just outside of Rock Hall. Featuring 3 spacious bedrooms and 3 full bathrooms — one on each level — this home provides flexibility and comfort for everyday living or guests. The open-concept main floor showcases luxury flooring, brand-new stainless steel

  Sarah Ulrick Rock Hall Properties Real Estate

  6416 Edesville Rd, Rock Hall, MD 21661
• 

  

  /22

  $1,099,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,784 Sq Ft

  25 Landing Ln, Chestertown, MD 21620

  **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

  Julia Hilfiker Gunther-McClary Real Estate

  25 Landing Ln, Chestertown, MD 21620
• 

  

  /23

  $849,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,980 Sq Ft

  104 Little Harbor Way, Chestertown, MD 21620

  **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

  Julia Hilfiker Gunther-McClary Real Estate

  104 Little Harbor Way, Chestertown, MD 21620
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  /9

  $110,000 New Construction

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft

  5656 Circle Park Dr Unit 5594, Rock Hall, MD 21661

  Brand new 2025 Clayton Ruby Z located in the Circle Park mobile home community in Rock Hall. This 2-bedroom, 2-bathroom home features a spacious open floor plan with a full bedroom and bathroom on either end, offering privacy and flexibility. The home comes complete with brand-new appliances and is ready for its first owners. Public water and sewer. Financing available through Clayton Homes,

  Sarah Ulrick Rock Hall Properties Real Estate

  5656 Circle Park Dr Unit 5594, Rock Hall, MD 21661
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  /3

  $175,000

  • Land
  • 32,670 Sq Ft
  • $233,333 per Acre

  7 Wilson Point Rd, Galena, MD 21635

  Build your custom Eastern Shore home at Wilson Point Estates, this intimate 14-lot community minutes from the Sassafras River and local marinas. Homesites feature a builder tie-in with Concierge Homes, offering a fully custom design experience guided by Construction Concierge by Conestoga. Design review and minimum building requirements apply. Pricing varies by lot and home design.

  Aaron Clark Patterson-Schwartz-Middletown

  7 Wilson Point Rd, Galena, MD 21635
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  /12

  $425,000 Open House 5/09

  • 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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  /12

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  26663 Maple Ave, Still Pond, MD 21667

  Three bedroom home in Still Pond. This renovated home has new kitchen, HVAC, baths, carpet, paint flooring and more! Located on .38 acres amenities include covered front and side porch, shed, 1.5 baths, Chestertown is a short drive away with restaurants and shopping. This is a Fannie Mae home, submit all offers on Homepath site.

  Aaron Butler Real Estate Consultants

  26663 Maple Ave, Still Pond, MD 21667
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  /46

  $147,000

  • Land
  • 1 Acre
  • $147,000 per Acre

  0 Lot 30 Hagy Rd, Rock Hall, MD 21661

  Welcome to Little Neck Farm - this waterfront community has 30 homesites within a 354 acre farm with 4 miles of protected shoreline and plenty of open space where getting back to nature is possible. Lot 30 is available for sale - it is a generous level one acre lot with plenty of room to build your dream or getaway home. The lot has evergreens and crape myrtle plantings outlining a portion of the

  Cindy DelZoppo Northrop Realty

  0 Lot 30 Hagy 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. The rear portion of the property is designated forested shrub wetlands, though it’s been

  Maryn LeClair Chesapeake Real Estate Associates, LLC

  0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
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  /62

  $3,150,000

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

  6520 Swan Creek Rd, Rock Hall, MD 21661

  All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+/- acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser

  William Norris Select Land & Homes, LLC

  6520 Swan Creek Rd, Rock Hall, MD 21661
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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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  /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 Real Estate

  2 Sassafras Cove Rd, Galena, MD 21635
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  /2

  $38,000

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

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

  Dee Dee Miller Long & Foster Real Estate, Inc.

  0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
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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

  $299,000 Open Sun 1PM - 3PM

  • 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 kitchen is

  ALICE BENNETT Patterson-Schwartz Real Estate

  11060 Plum Dr, Worton, MD 21678

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