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14 Third Ave, Betterton
$245,000
3 Beds ⋅ 3 Baths
A rare opportunity near the Chesapeake Bay! Bring your vision to life in the charming waterfront community of Betterton. This Victorian-style home offers over 2,068 sq. ft., featuring a completed exterior and an unfinished interior that gives the next owner the opportunity to finish and customize the home to their own style. Designed for 3 bedrooms and 3 full bathrooms, with the potential for a 4th bedroom or additional living space above the garage. The unfinished interior features open stud walls with roughed-in plumbing and electric, underground electric with 200-amp service, 2x6 exterior walls, 9-foot ceilings on the first floor and basement, Andersen windows, steel entry doors, and an oversized garage door. A beautiful wrap-around porch, attached side-entry garage, and cleared, level 0.24-acre lot add to the possibilities. Located just 3 short blocks from the Chesapeake Bay and a short walk to Betterton Beach, enjoy convenient access to the beach, boardwalk, boat ramp, fishing, swimming, basketball and tennis courts, picnic pavilions, and a town playground. Whether you're envisioning a year-round residence, vacation getaway, or investment opportunity, much of the vision is already in place. Bring your ideas and make this unique property near the Bay your own!

14 Third Ave, Betterton

Listing courtesy of Foraker Realty Co.. Contact:

21899 Lovers Ln, Rock Hall
$131,000
2 Beds ⋅ 1 Baths
Welcome to peaceful country living in this cozy 2-bedroom, 1-bath manufactured home. Nestled in a serene setting, this home offers several recent improvements. Major updates include a new roof installed in 2026 with a lifetime warranty, newly installed storm door, insulated pipes, hot water heater, and gutters. Step outside and enjoy the covered rear porch—perfect for relaxing and taking in the tranquil surroundings. The partially fenced backyard provides additional outdoor space, while the detached shed offers convenient storage and is equipped with electricity and cable-ready connections. With its recent updates, peaceful setting, and outdoor amenities, this home is ready for its next owner to make it their own. Property is being sold strictly as-is.

21899 Lovers Ln, Rock Hall

Listing courtesy of Coldwell Banker Realty. Contact:

25373 Worton Lynch Rd, Worton
$175,000
1 Beds ⋅ 1 Baths
Charming "TINY" house within quiet community of Worton off the main thoroughfare. Woods, public water and sewer, mature trees, deck with view of woods. One bedroom and bath, eat-in kitchen. Separate laundry/utility room. Not fancy by delightful on large lot. Only ten minutes from Historic Chestertown where one can find all daily needs plus many year-round cultural events including live performances. Washington College, tenth oldest college in America, offers programs and events continually. Minutes from Lockbriar (Pick Your Own) Farm and rest of beautiful County of Kent. Bettertown sandy Public beach on Chesapeake Bar and modern playground is nearby. Weekends? Year-round living?

25373 Worton Lynch Rd, Worton

Listing courtesy of Maryland Heritage Properties. Contact:

34155 Bradford Johnson Rd, Galena
$55,000
1 Beds ⋅ 1 Baths
Small detached dwelling on secluded .50 Acre lot. Property recently acquired through tax foreclosure. Seller has no knowledge of the property including condition of septic and well. Buyer encouraged to conduct due diligence.

34155 Bradford Johnson Rd, Galena

Listing courtesy of Taylor Properties. Contact:

7415 Wilkins Ln, Chestertown
$229,000
3 Beds ⋅ 1 Baths
This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly increase rental income or resale value. The spacious 0.34-acre lot provides ample outdoor space, while off-street and driveway parking enhances convenience for residents. A shed on the property offers additional storage options, appealing to renters seeking practicality. With no pool maintenance costs and a straightforward layout, this property is low-maintenance, making it an attractive option for investors looking to maximize returns. The combination of location, features, and potential for appreciation makes this property a compelling addition to any real estate portfolio.

7415 Wilkins Ln, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

10520 Worton Rd, Worton
$100,000
3 Beds ⋅ 1 Baths
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/6/2026, 10:00 AM. Bidding ends 10/8/2026, 12:45 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 County, this single-family home offers approximately 1,896 square feet of living area on a 0.51± acre lot. The home is situated along Worton Road, approximately five miles north of historic Chestertown. The location provides convenient access to shopping, dining, employment centers, recreational amenities, and the surrounding waterfront communities of Kent County. Maryland Route 297 provides connectivity throughout the Worton and Chestertown areas, while nearby routes offer access toward Rock Hall, Betterton, Cecil County, and Delaware. Each person entering the property is required to complete a right of entry agreement prior to touring the property.

10520 Worton Rd, Worton

Listing courtesy of Ashland Auction Group LLC. Contact:

10540 Worton Rd, Worton
$90,000
3 Beds ⋅ 1 Baths
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/6/2026, 10:00 AM. Bidding ends 10/8/2026, 12:50 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 County, this single-family home offers approximately 1,056 square feet of living area on a 0.46± acre lot. The home is situated along Worton Road, approximately five miles north of historic Chestertown. The location provides convenient access to shopping, dining, employment centers, recreational amenities, and the surrounding waterfront communities of Kent County. Maryland Route 297 provides connectivity throughout the Worton and Chestertown areas, while nearby routes offer access toward Rock Hall, Betterton, Cecil County, and Delaware. Each person entering the property is required to complete a right of entry agreement prior to touring the property.

10540 Worton Rd, Worton

Listing courtesy of Ashland Auction Group LLC. Contact:

316 Middle St, Millington
$25,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/2/2026, 10:00 AM. Bidding ends 10/6/2026, 12:40 PM. The list price is the suggested opening bid. Deposit: $5,000. This two-story detached house is located in Millington, MD within Kent County. Residents can enjoy the nearby attractions and facilities such as the Waterfront Park, Rob Vanary Park & Millington Park. The property is vacant but is in a dilapidated condition, ready for a major build up. It has easy access to Maryland Routes 291 and 313, connecting Route 301.

316 Middle St, Millington

Listing courtesy of Ashland Auction Group LLC. Contact:

5804 Downey Ave, Rock Hall
$199,000
Unique opportunity to restore and customize the historic former "Rock Hall Shirt Factory!" This 5,558± sq. ft. building is situated on a 0.31± acre in-town lot and offers endless potential for investors, developers, or buyers looking for a one-of-a-kind project. The interior has been framed and studded for rooms, providing a head start on the renovation process while allowing you to complete the layout to suit your vision. Zoned R-3 High Density Residential, the property may offer the potential for multiple apartments or conversion into duplex or triplex units, subject to Town of Rock Hall approval and all applicable zoning and building requirements. The property features two separate driveways, a one-car garage, and all remaining contents will convey with the sale, potentially including valuable construction materials to assist with completing the project. Conveniently located just a short walk from Rock Hall's charming Main Street, you'll enjoy easy access to local shops, restaurants, the harbor, and community events. Bring your imagination and transform this historic property into something truly special!

5804 Downey Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

25028 Heather Ln, Worton
$90,000
3 Beds ⋅ 2 Baths
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/1/2026, 10:00 AM. Bidding ends 10/5/2026, 12:00 PM. The list price is the suggested opening bid. Deposit: $15,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. 1,184± SF ranch-style single family home located in the Knights Landing area of Worton, Maryland. The property is located in Kent County, within close proximity to local schools, neighborhood amenities, Chestertown-area shopping and services, and Eastern Shore recreation destinations including Betterton and the surrounding Chesapeake Bay region.

25028 Heather Ln, Worton

Listing courtesy of Ashland Auction Group LLC. Contact:

11989 Augustine Herman Hwy, Kennedyville
$245,000
2 Baths
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

104 Conley Dr, Chestertown
$239,900
3 Beds ⋅ 2 Baths
Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

104 Conley Dr, Chestertown

Listing courtesy of Cummings & Co. Realtors. Contact:

11989 Augustine Herman Hwy, Kennedyville
$245,000
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

234 N College Ave, Chestertown
$85,000
2 Beds ⋅ 1 Baths
Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown’s shops, restaurants, and waterfront, the location can’t be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland’s most beloved small towns. Sold as-is. Cash or renovation loans preferred.

234 N College Ave, Chestertown

Listing courtesy of Cummings & Co Realtors. Contact:

5656 Circle Park Dr Park Unit #5594, Rock Hall
$89,000
2 Beds ⋅ 2 Baths
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, subject to credit score and financing approval. Offered at $110,000. Buyer must be approved by the park. Ground rent is $550/month (buyer to verify). Contact us to schedule a tour.

5656 Circle Park Dr Park Unit #5594, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

26663 Maple Ave, Still Pond
$223,000
3 Beds ⋅ 2 Baths
Price Reduced! 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.

26663 Maple Ave, Still Pond

Listing courtesy of Real Estate Consultants. Contact:

117 Water St N Unit 1B, Chestertown
$200,000
1 Beds ⋅ 1 Baths
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 of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006164 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 1B, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: