22

Kent County MD Homes under $300,000

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  • 423 Cypress St, Millington, MD 21651
    423 Cypress St, Millington, MD 21651
    423 Cypress St, 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
  • 301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    /40

    $299,900

    • 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
  • 6374 Rock Hall Rd, Rock Hall, MD 21661
    6374 Rock Hall Rd, Rock Hall, MD 21661
    6374 Rock Hall Rd, Rock Hall, MD 21661
    /34

    $295,000 Open Sat 11AM - 1PM

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

    6374 Rock Hall Rd, Rock Hall, MD 21661

    Welcome to life in Rock Hall — a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living. *SELLER ASSISTANCE AVAILABLE TOWARDS CLOSING COSTS* This lovingly renovated home was thoughtfully updated by owners who cared about the details—not a quick flip—resulting in a property full of character and quality improvements

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    6374 Rock Hall Rd, Rock Hall, MD 21661
  • 11167 Oak Ln, Worton, MD 21678
    11167 Oak Ln, Worton, MD 21678
    11167 Oak Ln, Worton, MD 21678
    /17

    $299,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    11167 Oak Ln, Worton, MD 21678

    Affordable, updated, and close to the water! Welcome to easy Eastern Shore living in this beautifully updated 3-bedroom, 1-bath home that truly feels like new. Recently updated with a new roof, water heater, HVAC system, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, and a vapor barrier and insulation in the crawlspace. This home brings modern

    Marti McGinty Chesapeake Real Estate Associates, LLC

    11167 Oak Ln, Worton, MD 21678
  • 10971 Bottom Rd, Worton, MD 21678
    10971 Bottom Rd, Worton, MD 21678
    10971 Bottom Rd, Worton, MD 21678
    /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
  • 611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    /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
  • 21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    /20

    $265,000

    • 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, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head

    Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
  • 26663 Maple Ave, Still Pond, MD 21667
    26663 Maple Ave, Still Pond, MD 21667
    26663 Maple Ave, Still Pond, MD 21667
    /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
  • 11060 Plum Dr, Worton, MD 21678
    11060 Plum Dr, Worton, MD 21678
    11060 Plum Dr, Worton, MD 21678
    /14

    $299,000

    • 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
  • 25044 Travis Trail, Worton, MD 21678
    25044 Travis Trail, Worton, MD 21678
    25044 Travis Trail, Worton, MD 21678
    /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
  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /4

    $250,000

    • Land
    • 37,026 Sq Ft
    • $294,118 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • 139 Prospect St, Chestertown, MD 21620
    139 Prospect St, Chestertown, MD 21620
    139 Prospect St, Chestertown, MD 21620
    /28

    $225,000

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft

    139 Prospect St, Chestertown, MD 21620

    Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in

    Barbara McCaffrey Redfin Corp

    139 Prospect St, Chestertown, MD 21620
  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /7

    $225,000

    • Land
    • 37,897 Sq Ft
    • $258,621 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.87± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic.There is also

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620
  • 5898 Williams St, Rock Hall, MD 21661
    5898 Williams St, Rock Hall, MD 21661
    /2

    $250,000

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

    5898 Williams St, Rock Hall, MD 21661

    Welcome to 5898 Williams Street, Rock Hall, MD! This 5-acre cleared parcel offers an exciting development opportunity in the heart of Rock Hall. With public water and sewer available, the property provides excellent development potential. Formerly zoned MCI, it is now zoned residential under the newly adopted Rock Hall 2040 Comprehensive Plan, opening the door for possible subdivision. Situated

    Cindy Genther Rock Hall Properties Real Estate

    5898 Williams St, Rock Hall, MD 21661
  • 31695 Olivet Cir, Galena, MD 21635
    31695 Olivet Cir, Galena, MD 21635
    31695 Olivet Cir, Galena, MD 21635
    /18

    $200,000

    • 3 Beds
    • 2 Baths
    • 1,701 Sq Ft

    31695 Olivet Cir, Galena, MD 21635

    Welcome Home to 31695 Olivet Circle, this 3 bedroom 2 bath home is a great started home! Beautiful property with lots of possibilities! Off the beaten path & surrounded by nature with a detached garage.

    Donnie Horton RE/MAX Chesapeake

    31695 Olivet Cir, Galena, MD 21635
  • 301 Hilltop Ln, Chestertown, MD 21620
    301 Hilltop Ln, Chestertown, MD 21620
    301 Hilltop Ln, Chestertown, MD 21620
    /36

    $225,000

    • 3 Beds
    • 2.5 Baths
    • 1,197 Sq Ft

    301 Hilltop Ln, Chestertown, MD 21620

    Move-in ready and priced to sell, this 3-bedroom, 2.5-bath end-unit townhouse offers the perfect blend of value, comfort, and natural light. Tucked alongside community open space, this home lives larger than expected with added privacy and bright, airy interiors. Inside, you’ll find upgraded flooring and modern lighting throughout, creating a clean, updated feel from the moment you walk in. Two

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    301 Hilltop Ln, Chestertown, MD 21620
  • 26670 Maple Ave, Still Pond, MD 21667
    26670 Maple Ave, Still Pond, MD 21667
    26670 Maple Ave, Still Pond, MD 21667
    /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
  • 115 Acorn Dr, Chestertown, MD 21620
    115 Acorn Dr, Chestertown, MD 21620
    115 Acorn Dr, Chestertown, MD 21620
    /40

    $296,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 2.5 Baths
    • 1,864 Sq Ft

    115 Acorn Dr, Chestertown, MD 21620

    Welcome to 115 Acorn Drive in the desirable Oak Hollow community of Chestertown, Maryland—an end-unit townhome offering space, comfort, and convenience. This three-level home is ideally located near shopping, the YMCA, and local schools, making everyday living easy and accessible. The ground level features a front-entry one-car garage with interior access, leading to a versatile finished space

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    115 Acorn Dr, Chestertown, MD 21620
  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /22

    $259,900 New Construction

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

    103 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, 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 suite with walk-in

    David Moore Real Broker, LLC

    103 Metcalf Rd, Chestertown, MD 21620
  • 24581 Willow Oak Ln, Chestertown, MD 21620
    24581 Willow Oak Ln, Chestertown, MD 21620
    24581 Willow Oak Ln, Chestertown, MD 21620
    /29

    $229,990

    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    24581 Willow Oak Ln, Chestertown, MD 21620

    If you're looking for that secluded spot, with land, room to grow and stretch, and don't mind a project, look no further! Dream location on a private road, backing to farmland, and yet just a few miles outside of downtown Chestertown! The house is midway through a full renovation. Walls are in place, electric run, plumbing roughed-in, new siding and a brand New HVAC! All the hard stuff is done!

    Michele Palmer Doug Ashley Realtors, LLC

    24581 Willow Oak Ln, Chestertown, MD 21620
  • 108 Oak Leaf Dr, Chestertown, MD 21620
    108 Oak Leaf Dr, Chestertown, MD 21620
    108 Oak Leaf Dr, Chestertown, MD 21620
    /39

    $299,500

    • 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
  • 117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, 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
Maryland Kent County

Real Estate & Homes in Kent County, MD under $300,000

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