156

Kent County MD Homes for Sale

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  • /53

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • /16

    $170,000

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft

    107 Conley Dr, Chestertown, MD 21620

    Purchase of opportunity thru rehab financing for completion of a new kitchen, painting and flooring . Call for details and will assist you with your dream of owning your own home.

    Debbie Meikle Doug Ashley Realtors, LLC

    107 Conley Dr, Chestertown, MD 21620
  • /22

    $240,000

    • 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
  • /17

    $1,125,000

    • Land
    • 0.51 Acre
    • $2,205,882 per Acre

    #2 Lawton Ave, Rock Hall, MD 21661

    Over half an acre of prime bayfront property! Build a beautiful home on popular Lawton Avenue, the Gratitude neighborhood in Rock Hall. Enjoy sunsets, spectacular views of the bay, and additional views of Swan Creek in back. Spend idyllic afternoons watching the boats sail by! Lawton Ave offers privacy, but is only a short stroll to multiple restaurants, the town beach, and many marinas; there is

    Lynn Hilfiker Gunther-McClary Real Estate

    #2 Lawton Ave, Rock Hall, MD 21661
  • /44

    $344,900

    • 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
  • /2

    $19,900

    • Land
    • 0.11 Acre
    • $180,909 per Acre

    25034 Lambs Meadow Rd, Worton, MD 21678

    This property, situated on a 0.11-acre lot, offers a blank canvas for your vision. Located in Kent County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.

    Dustin Parker The Parker Group

    25034 Lambs Meadow Rd, Worton, MD 21678
  • /8

    $364,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft

    21133 Striper Run, Rock Hall, MD 21661

    New Construction Alert! The last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates are now for sale. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the 1st and 2nd levels is included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious

    Cindy Genther Rock Hall Properties Real Estate

    21133 Striper Run, Rock Hall, MD 21661
  • /3

    $125,000

    • Land
    • 0.75 Acre
    • $166,667 per Acre

    12 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

    12 Wilson Point Rd, Galena, MD 21635
  • /3

    $175,000

    • Land
    • 0.75 Acre
    • $233,333 per Acre

    8 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

    8 Wilson Point Rd, Galena, MD 21635
  • /24

    $395,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2 Baths
    • 2,162 Sq Ft

    21733 Centennial Ln, Rock Hall, MD 21661

    Welcome to Crosby Woods, a charming new community located less than a mile from downtown Rock Hall. This thoughtfully designed neighborhood features just ten single-family homes situated on a quiet cul-de-sac with shared open space and no HOA. This brand-new 2,162 sq. ft. rancher offers comfortable one-level living with four bedrooms and two full bathrooms. The home features beautifully finished

    Sarah Ulrick Rock Hall Properties Real Estate

    21733 Centennial Ln, Rock Hall, MD 21661
  • /29

    $390,000

    • 3 Beds
    • 2.5 Baths
    • 1,712 Sq Ft

    21124 Striper Run, Rock Hall, MD 21661

    This beautiful home as has many upgrades. There is a lovely front porch, as well as a screened back porch. The back porch provides lots of privacy and faces trees and wildlife for viewing. The open floor plan features a kitchen and dining area, while leading from the living room with a warm propane fireplace. There's a nice pantry for storage and a half bath on the main level. Upstairs features

    Robin Fithian Rock Hall Properties Real Estate

    21124 Striper Run, Rock Hall, MD 21661
  • /2

    $345,000 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,215 Sq Ft

    11350 Lynch Rd, Worton, MD 21678

    Welcome home to this well-maintained 3-bedroom, 11⁄2-bath brick rancher that combines classic charm with a ready-to-go layout, making it yours to make your own. Nestled in the peaceful countryside just minutes from Chestertown and an easy commute to Middletown, this home offers the best of rural living with open views and fresh country air. Step inside to find a cozy living room, hallway and

    Grace Crockett Doug Ashley Realtors, LLC

    11350 Lynch Rd, Worton, MD 21678
  • /2

    $37,000

    • Land
    • 0.34 Acre
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • /48

    $1,395,500 Open House 3/28

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

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners near Widehall and the Custom House. Completely restored in 2024–2025 by one of the town’s most iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /3

    $150,000

    • Land
    • 0.75 Acre
    • $200,000 per Acre

    11 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

    11 Wilson Point Rd, Galena, MD 21635
  • /3

    $120,000

    • Land
    • 0.75 Acre
    • $160,000 per Acre

    3 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

    3 Wilson Point Rd, Galena, MD 21635
  • /13

    $259,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    107 Metcalfe Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxuryvinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granitecountertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment.Upstairs you'll find generously sized bedrooms including a large primary

    David Moore Real Broker, LLC

    107 Metcalfe Rd, Chestertown, MD 21620
  • /2

    $9,500

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • /8

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • /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
  • /6

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, & +/- 7 Miles to downtown Chestertown, Maryland. Easy Access to Major Traffic Artery Fairlee Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
  • /4

    $1,495,000 Coming Soon

    • 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
  • /24

    $80,000

    • Land
    • 0.17 Acre
    • $470,588 per Acre

    0 1st Ave, Betterton, MD 21610

    PRICE REDUCTION!!Wonderful lot in Betterton, only 2 blocks from the beach, and your chance to make wonderful memories in this community known as the "Jewel of the Chesapeake". Betterton sits right on the upper Chesapeake Bay at the mouth of the Sassafras River, an extremely popular boating area. The beach is beautiful with calm waters and amenities for a perfect day at the beach. This

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    0 1st Ave, Betterton, MD 21610
  • /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
  • /3

    $269,900 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,356 Sq Ft

    112 Elm St, Chestertown, MD 21620

    Brian Whitaker Coldwell Banker Waterman Realty

    112 Elm St, Chestertown, MD 21620
  • /8

    $14,900

    • Land
    • 0.84 Acre
    • $17,738 per Acre

    25619 W Hill Rd, Worton, MD 21678

    Explore this unique opportunity to own a versatile piece of land in a prime location. This piece of land offers endless possibilities, so don't miss the opportunity to make it your own! Buyer to conduct their own due diligence to verify all listing information.

    Dustin Parker The Parker Group

    25619 W Hill Rd, Worton, MD 21678
  • /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
  • /3

    $1,250,000

    • Land
    • 49.83 Acres
    • $25,085 per Acre

    0 Rock Hall Rd, Rock Hall, MD 21661

    50 acres of mixed use development property within Rock Hall town limits. Great location with access via state highway/MD Rt. 20, and 3 town roads; almost 1000 ft of road frontage. The property is partially cleared and includes a small area of wetlands that would make a nice pocket park within the development. Public water and sewer service hook ups are available. Fiber optic cables are buried

    Robin Fithian Rock Hall Properties Real Estate

    0 Rock Hall Rd, Rock Hall, MD 21661
  • /6

    $5,000

    • Land
    • 0.34 Acre
    • $14,706 per Acre

    0 Beltram Rd, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 3/16/2026 @ 10:00 AM. Bidding ends 3/18/2026 @ 12:25 PM. The list price is the suggested opening bid. Deposit: $5,000. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, Chestertown, MD 21620
  • /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
  • /2

    $9,000

    • Land
    • 0.34 Acre
    • $26,471 per Acre

    0 Kinglet Rd, Chestertown, MD 21620

    All offers considered! Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Kinglet Rd, Chestertown, MD 21620
  • /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
  • /12

    $164,000

    • Land
    • 2.15 Acres
    • $76,279 per Acre

    7224 Rock Hall Rd, Rock Hall, MD 21661

    Discover the charm of Kent County’s rural lifestyle on this fenced, 2.15-acre cleared lot. Perfectly situated along Rock Hall Road, the property features an existing two-car garage, a 6’x8’ storage shed, and mature trees framing vast pastoral views. With electric service and an existing well already in place, it’s ready for your vision—whether that’s building your dream home, creating a weekend

    Cindy Genther Rock Hall Properties Real Estate

    7224 Rock Hall Rd, Rock Hall, MD 21661
  • /26

    $449,000 Coming Soon

    • 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
  • /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
  • /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
  • /3

    $110,000

    • Land
    • 0.75 Acre
    • $146,667 per Acre

    14 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

    14 Wilson Point Rd, Galena, MD 21635
  • /2

    $399,900 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 2,535 Sq Ft

    104 Flying Cloud Dr, Chestertown, MD 21620

    Welcome to The Verona, a spacious three-story, move-in ready home offering over 2,300 square feet of thoughtfully designed living space. With five bedrooms and three and a half bathrooms, this home provides the perfect balance of comfort, functionality, and flexibility for modern living.Step inside to an inviting foyer that leads to the bright and open main living area, where the family room

    David Moore Real Broker, LLC

    104 Flying Cloud Dr, Chestertown, MD 21620
  • /2

    $22,000

    • Land
    • 0.5 Acre
    • $44,000 per Acre

    0 Dutchtown Rd, Still Pond, MD 21667

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Dutchtown Rd, Still Pond, MD 21667
  • /7

    $89,999

    • Land
    • 0.69 Acre
    • $130,433 per Acre

    32072 Shorewood Rd, Galena, MD 21635

    Build Your Dream Home in Shorewood Estates!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 had plans to build but, life took a different direction. Their loss is your

    Tanya Luckenbill Integrity Real Estate

    32072 Shorewood Rd, Galena, MD 21635

Showing Results 41 - 80, Page 2 of 4

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