174

Homes for Sale near Kent County High School

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  • /43

    $449,000

    • 3 Beds
    • 2.5 Baths

    1 Idlewhile Ave Unit 4, Betterton, MD 21610

    Crew's Landing 3 bedroom Townhouse, located in Betterton, The Jewel of the Chesapeake. This 12 unit complex has become a premier waterfront community on the upper Bay. Located on a 5 acre setting of beautiful landscape offering carefree living. It includes a community dock and a great private sandy beach. The unit has had upgrades with wood plank tile floors, kitchen with granite countertops, and

    Ashton Kelley Gunther-McClary Real Estate

    1 Idlewhile Ave Unit 4, Betterton, MD 21610
  • /15

    $550,000

    • Land
    • 50 Acres
    • $11,000 per Acre

    0 Bradford Johnson Rd, Golts, MD 21635

    Excellent Opportunity to own a great 50+/- acre hunting and recreational property in northern Kent County Maryland. Diverse wooded acres provide for good privacy with reasonable road frontage and an excellent habitat lending an upper hand for Deer, Turkey and other diverse wildlife species. The convenience of this wooded parcel is another reason to move it to the top of your list at around 20

    BRIAN MORRIS The Land Group

    0 Bradford Johnson Rd, Golts, MD 21635
  • /40

    $598,000

    • 3 Beds
    • 3 Baths
    • 2,672 Sq Ft

    5807 Blue Claw Ct, Rock Hall, MD 21661

    Welcome to luxury living in Waterman’s Estates in the heart of Rock Hall! This beautifully updated 4-bedroom, 3-bath home offers approximately 2,600 square feet of light-filled living space with soaring vaulted ceilings and an open, inviting floor plan. A propane fireplace in the living room creates a warm and welcoming focal point, while plenty of storage throughout the home adds everyday

    Cindy Genther Rock Hall Properties Real Estate

    5807 Blue Claw Ct, Rock Hall, MD 21661
  • /24

    $419,900

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

    109 S College Ave, Chestertown, MD 21620

    Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors,

    Jeff Guthrie Taylor Properties

    109 S College Ave, Chestertown, MD 21620
  • /29

    $299,000

    • 2 Beds
    • 2 Baths
    • 1,628 Sq Ft

    5188 Skinners Neck Rd, Rock Hall, MD 21661

    This beautifully updated home in Rock Hall offers a blend of classic charm and modern improvements. The open living area features refinished original fir wood floors and flows into an updated kitchen with gas range, dishwasher, refrigerator and ample workspace that is ideal for everyday cooking or entertaining. The main level includes a bedroom and full bath, while the second-floor owner’s suite

    Jordan Larigan LPT Realty, LLC

    5188 Skinners Neck Rd, Rock Hall, MD 21661
  • /82

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,383 Sq Ft

    8276 Broad Neck Rd, Chestertown, MD 21620

    Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room and an office.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8276 Broad Neck Rd, Chestertown, MD 21620
  • /7

    $675,000

    • Land
    • 14.11 Acres
    • $47,838 per Acre

    14200 Metasequoia Ct, Galena, MD 21635

    It is a rare opportunity for a private waterfront lot off the Sassafras River to come available. This 14 acre parcel of land is located above the bridge in a well established small community of Gentle Winds. Scenic and tranquil area for birding watching, kayaking or taking a short boat ride to restaurants located down the river. With this 14 acre lot, there are open areas and woods to play with.

    Ashton Kelley Gunther-McClary Real Estate

    14200 Metasequoia Ct, Galena, MD 21635
  • /40

    $309,900

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    301 Lincoln Dr, Chestertown, MD 21620

    Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow between the living, dining, and kitchen areas — ideal for both everyday living and entertaining.The spacious kitchen features a central island, stainless steel appliances, and ample cabinetry, making it as functional as it is

    Heather Dolan Chesapeake Real Estate Associates, LLC

    301 Lincoln Dr, Chestertown, MD 21620
  • /58

    $437,500

    • 3 Beds
    • 1 Bath
    • 1,440 Sq Ft

    5827 S Hawthorne Ave, Rock Hall, MD 21661

    Just a block and a half from the water, this adorable Cape Cod is the retreat you’ve been dreaming of. Whether you’re looking for a peaceful primary residence, a weekend or vacation getaway, or an investment property to Airbnb, this home perfectly balances cozy character with nearby conveniences. Peace and quiet doesn’t mean being disconnected. You're just a short stroll or drive from downtown

    Amy Mullen Iron Valley Real Estate Ocean City

    5827 S Hawthorne Ave, Rock Hall, MD 21661
  • /11

    $79,999

    • Land
    • 0.69 Acre
    • $115,941 per Acre

    32072 Shorewood Rd, Galena, MD 21635

    ***PRICE REDUCED***Build Your Dream Home in Shorewood Estates! Choose your own builder or pick up where seller's left off.Looking for peace, quiet, and a true Eastern Shore lifestyle? Welcome to Shorewood Estates, a private water-oriented community on Swantown Creek off the Sassafras River. This .69-acre elevated lot backs to woods and has passed perc test—perfect for your dream build. Owners

    Tanya Luckenbill Integrity Real Estate

    32072 Shorewood Rd, Galena, MD 21635
  • /51

    $1,279,000

    • 5 Beds
    • 3 Baths
    • 2,956 Sq Ft

    231 Richard Dr, Chestertown, MD 21620

    Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town

    Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, Chestertown, MD 21620
  • /45

    $489,900

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    201 Ericsson Ave, Betterton, MD 21610

    Phenomenal 3.75 acres+- in sought after Betterton. The hidden bay front town retreat from the past.Rolling pasture like setting with specimen trees. Farmhouse style home with pinewood floors perched up high overlooking the property. Detached garage and 2 other large sheds on the property. Craftsman's dream. Deer and all other creatures abound. Short walk to town beach, gazebo and boat ramp.

    Jonathan Olsavsky Coldwell Banker Waterman Realty

    201 Ericsson Ave, Betterton, MD 21610
  • /73

    $1,600,000

    • 7 Beds
    • 6 Baths
    • 5,400 Sq Ft

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

    **Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 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

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
  • /23

    $350,000

    • 7 Beds
    • 6 Baths
    • 850 Sq Ft

    117 N Water St Unit 2B, 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 2B, Chestertown, MD 21620
  • /24

    $375,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, 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 2A, Chestertown, MD 21620
  • /46

    $685,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

    117 N Water St Unit 1A, 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 1A, Chestertown, MD 21620
  • /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
  • /13

    $795,000

    • 2 Baths
    • 2,045 Sq Ft

    201 N Lynchburg St, Chestertown, MD 21620

    Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • /22

    $235,000

    • 3 Beds
    • 1.5 Baths
    • 1,278 Sq Ft

    25044 Travis Trail, Worton, MD 21678

    Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town

    Jay McCall Coldwell Banker Chesapeake Real Estate Company

    25044 Travis Trail, Worton, MD 21678
  • /44

    $339,000

    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a

    Gregory Morris Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
  • /56

    $675,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
  • /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
  • /38

    $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
  • /16

    $95,000

    • Land
    • 0.82 Acre
    • $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
  • /20

    $310,000

    • 3 Beds
    • 2.5 Baths
    • 1,628 Sq Ft

    21103 Striper Run, Rock Hall, MD 21661

    Easy, low-maintenance living in the heart of Rock Hall. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, and fresh paint throughout. The entry level offers a flexible bedroom or home office with en-suite

    Courtney Chipouras TTR Sotheby's International Realty

    21103 Striper Run, Rock Hall, MD 21661
  • /33

    $510,000

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft

    32135 River Rd, Millington, MD 21651

    Experience true waterfront living on the beautiful Chester River in Millington, just 15 minutes from Middletown, DE. Situated on 0.53 acres, this charming riverfront carriage house captures breathtaking panoramic water views and offers the perfect blend of relaxation, recreation, and convenience. An expansive lighted deck creates the ideal setting for morning coffee, outdoor dining, entertaining

    Christine Catalano Coldwell Banker Realty

    32135 River Rd, Millington, MD 21651
  • /15

    $295,000

    • 3 Beds
    • 1 Bath
    • 952 Sq Ft

    423 Cypress St, Millington, MD 21651

    Turn-key, one-level living in the heart of charming downtown Millington! Welcome to 423 Cypress Street, a beautifully maintained and thoughtfully updated home that is truly move-in ready!! Take advantage of the seller’s option to convey the home fully furnished as they relocate out of state. This stress-free property has been lovingly cared for, and it shows in every detail. Major updates include

    Jenyne Ward Patterson-Schwartz Real Estate

    423 Cypress St, Millington, MD 21651
  • /25

    $270,000

    • 2 Beds
    • 2 Baths
    • 720 Sq Ft

    10971 Bottom Rd, Worton, MD 21678

    Nestled among the farmland and waterways in Kent County is a cul de sac of new homes on Bottom Road just outside of Chestertown. The new 2 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered

    Andy Batch Keller Williams Select Realtors of Annapolis

    10971 Bottom Rd, Worton, MD 21678
  • /2

    $15,000

    • Land
    • 0.52 Acre
    • $28,846 per Acre

    22681 Wood Yard Ln, Chestertown, MD 21620

    Half acre+ secluded wooded lot. There used to be a house on the property but county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot and there is a 16' right of way to access. Buyer to do any due diligence. Could be a great hunting property surrounded by woods and farmland!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22681 Wood Yard Ln, Chestertown, MD 21620
  • /62

    $3,500,000

    • 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
  • /38

    $385,000

    • 3 Beds
    • 2.5 Baths
    • 1,270 Sq Ft

    11981 Dewees Ln, Kennedyville, MD 21645

    Come see this home in the sought after community of Village at Kennedyville. This beautiful, updated 3 bedroom 2 and 1/2 bath home is awaiting it's next owner. As you enter this home you immediately feel the pride in ownership and notice the updates. From the bright open feel of the home and gourmet kitchen featuring stainless appliances with the refrigerator replaced in 2023, the dishwasher

    Edward Beres RE/MAX Executive

    11981 Dewees Ln, Kennedyville, MD 21645
  • /28

    $340,000

    • 3 Beds
    • 1.5 Baths
    • 1,233 Sq Ft

    5916 N Main St, Rock Hall, MD 21661

    Welcome to this charming 3-bedroom rancher in the quaint town of Rock Hall. Featuring beautiful wood floors throughout, this cozy home is being sold as-is—perfect for buyers looking to add their own personal touch. A standout feature is the detached garage with a bathroom rough-in, currently used as an entertainment space or “man cave.” With a few updates, it could easily be transformed into a

    Christine Johnson RE/MAX Executive

    5916 N Main St, Rock Hall, MD 21661
  • /5

    $21,000

    • Land
    • 2.6 Acres
    • $8,077 per Acre

    23698 L Rd, Chestertown, MD 21620

    Property record consists of two lots for a total of 2.6 Acres zoned Village. Please notify listing agent if you intend to walk the property.

    Joe Howerton Taylor Properties

    23698 L Rd, Chestertown, MD 21620
  • /45

    $525,000

    • 5 Beds
    • 3.5 Baths
    • 3,932 Sq Ft

    218 Camelot Dr, Chestertown, MD 21620

    Picture Perfect Colonial in Coventry Farms – Chestertown, MarylandWelcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates

    Dee Dee McCracken Coldwell Banker Realty

    218 Camelot Dr, Chestertown, MD 21620
  • /32

    $39,000

    • Land
    • 1.51 Acres
    • $25,828 per Acre

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620

    Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map 27, lots 254-257 & 297-300 (2 contiguous lots). The site is level & wooded. Raw land near Worton's Marina. Community has a boat ramp and offers easy access to the Chesapeake Bay. Chesapeake Landing has a voluntary HOA giving you access to the boat ramp, marina and a slip for an

    Becky Schor Berkshire Hathaway HomeServices Homesale Realty

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
  • /46

    $155,000

    • Land
    • 1 Acre
    • $155,000 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
  • /40

    $525,000

    • 5 Beds
    • 3.5 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    REDUCED! 311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • /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
  • /17

    $995,000

    • Land
    • 18.62 Acres
    • $53,437 per Acre

    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661

    Discover 18.62 acres of waterfront land on Tavern Creek, offering 1,086 feet of shoreline and stunning natural surroundings. Zoned Resource Conservation and currently tilled, this property provides a rare opportunity for those seeking space, privacy, and water access. A small portion of the shoreline lies within the flood zone; buyer to confirm buildability.

    Sarah Ulrick Rock Hall Properties Real Estate

    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661
  • /18

    $275,000

    • 2 Beds
    • 1.5 Baths
    • 920 Sq Ft

    611 Cannon St, Chestertown, MD 21620

    This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing

    Hayley Norris Select Land & Homes, LLC

    611 Cannon St, Chestertown, MD 21620

Showing Results 41 - 80, Page 2 of 5

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