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$289,900
2 Beds ⋅ 2 Baths
Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom, home office, or additional living space. The welcoming living room and eat-in kitchen both feature sliding glass doors that open to the side deck, creating a wonderful space for entertaining or simply relaxing while enjoying the peaceful surroundings. The kitchen offers vinyl plank flooring, oak cabinetry, an electric range, built-in microwave, dishwasher, and plenty of space for casual dining. The primary bedroom includes two closets and a private half bath, while the second bedroom features convenient washer and dryer hookups. Upstairs, the spacious loft boasts beautiful wood flooring and access to a second-story deck overlooking the wooded backyard. Stay comfortable year-round with central air conditioning, electric baseboard heat, and the cozy warmth of a wood stove that serves as an excellent supplemental heat source during the cooler months. Additional updates include a newer central A/C system (approximately 6 years old), a new water heater, and a new water softener. Need extra space for hobbies, storage, or projects? The detached 20' x 24' outbuilding with electricity, wood flooring, and a garage door offers endless possibilities as a workshop, studio, or storage for your outdoor gear. Enjoy everything Tolchester Estates has to offer, including exclusive resident access to a private community beach and boat ramp. Just a short walk or golf cart ride away, you'll also find Tolchester Marina and The Shanty Beach Bar, where you can enjoy waterfront dining, live music, boating, and breathtaking Chesapeake Bay sunsets. Whether you're searching for a full-time residence, weekend getaway, or vacation home, this property offers an incredible opportunity to enjoy the Chesapeake Bay lifestyle while adding your own personal touches. Being sold as-is.

21146 Montana Ave, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$650,000
List Price is opening bid. Online Auction Only! Bidding begins Saturday, August 15 and ends Thursday, August 20, 2026 at 1:00 PM. Exceptional Multi-Family Investment Opportunity in Chestertown! Introducing 104 Maple Avenue, a beautifully updated 6-unit apartment building ideally located in Kent County's desirable Chestertown area. Thoughtfully renovated, this income-producing property seamlessly blends modern finishes with practical functionality, making it an outstanding addition to any investment portfolio. Each unit has been carefully improved to provide attractive, comfortable living spaces designed to appeal to today's renters. The extensive updates enhance both the property's aesthetic appeal and long-term value while helping to minimize future maintenance concerns. Upon full occupancy, the property offers an impressive Gross Annual Rent of $129,300±, presenting an exceptional opportunity for investors seeking strong cash flow and long-term appreciation. Conveniently situated near Washington College, University of Maryland Medical Center, & downtown Chestertown's restaurants, shops, waterfront, and local amenities, the location further enhances its desirability for tenants. Whether you're expanding your real estate portfolio or acquiring a high-performing multi-family asset, 104 Maple Avenue represents a rare opportunity to own a updated six-unit building in one of Kent County's most charming and sought-after communities. Features and Highlights: • (6) Apartments • Thoughtfully Updated & Beautifully Maintained Building • Stabilized Asset in a Prime Location • Gross Annual Rent of $129,300± • 7 Electric Meters • 7 Electric Panels • 3 Forced Hot Air Units • 7,296± SF Building • 8± Onsite Parking Spaces Property Breakdown: Main Level -Central A/C -Forced Hot Air Heat Unit 1 Rented for $2,225/ mo 2 Bedrooms, 1 Full Bathroom Unit 2 Rented for $1,890/ mo 2 Bedrooms, 1 Full Bathroom Second Level -Mini Split A/C & Heating System(s) Unit 3 Rented for $1,520/ mo 2 Bedrooms, 1 Full Bathroom Unit 4 Rented for $1,820/ mo 2 Bedrooms, 1 Full Bathroom Note: tenant vacating at end of August. Third Level -Central A/C -Forced Hot Air Heat Unit 5 Rented for $1,400/ mo 2 Bedrooms, 1 Full Bathroom Unit 6 Rented for $1,920/ mo 2 Bedrooms, 2 Full Bathrooms Lower Level Unfinished Basement housing utilities & storage space. The information contained herein was obtained from sources deemed to be reliable, but is offered for informational purposes only. Neither the auctioneer or the owner make any representations or warranties with respect to the accuracy of information.

104 Maple Ave, Chestertown

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

$415,000
3 Beds ⋅ 3 Baths
Beautifully updated and maintained Colonial home in Dogwood Village. This spacious home offers nearly 2000 square feet of living plus a basement area. There is an attached 2 car garage and both a screened porch and open deck at the rear of the home. A fireplace in the living room adds warmth to cool fall and winter days. The rear of the home is accented by both spacious screened porch and an open deck. Perfect location with easy access to highways and tax free shopping in Middletown.

189 Birchwood, Galena

Listing courtesy of L. C. Parker Real Estate. Contact:

$380,000
3 Beds ⋅ 2 Baths
Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, this is a rare opportunity with tremendous potential. Property is being sold as-is

8312 Broad Neck Rd, Chestertown

Listing courtesy of Pearson Smith Realty, LLC. Contact: 5713861075
$740,000
3 Beds ⋅ 3 Baths
Welcome to your Eastern Shore oasis, an impressive nearly 3,700-square-foot home offering river access on almost 2 acres, a boat slip, stunning water views, and beautifully established grounds surrounded by mature trees. Inside, you’ll find a dramatic two-story foyer, hardwood floors, a designer kitchen with granite countertops and an oversized walk-in pantry, multiple living spaces, a wood-burning fireplace, and an enclosed sunroom overlooking the water. Step outside to the expansive Trex deck with a recessed hot tub, then follow the path directly to the river. With three bedrooms, three full bathrooms, a walkout lower level, two bonus space, and a two-car garage, this home delivers the space, finishes, and lifestyle you’ve been waiting for. Schedule your private tour today and experience this waterfront retreat for yourself. Furniture is available for purchase as well!

14540 Stirrup Lane Ln, Galena

Listing courtesy of Keller Williams Flagship. Contact:

$300,000
4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800
$500,000
A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Chestertown, this charming church of a little over 3,500 square feet offers a unique opportunity for continued use as a place of worship, community gathering space, or potential conversion. The property features wheelchair accessibility, on-site parking, and a layout ideal for a variety of uses. With its peaceful setting and classic structure, this building is ready to serve its next purpose. Also available with mls MDKE2006846 additionally

201 N Lynchburg St, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800
$259,900
3 Beds ⋅ 1 Baths
Coming Soon in Rock Hall! Freshly renovated and ready to welcome you home. This property offers a bright new feel from the moment you step inside. Thoughtful updates and beautiful finishes create an inviting interior, while the spacious yard and mature trees provide plenty of room to enjoy the outdoors. Whether you’re searching for your first home, looking to downsize or low maintenance living, this home is one you’ll want to see! OPEN HOUSE WEEKEND : Saturday August 8th 10AM-12PM and Sunday August 9th 12PM-2PM

6179 E Dorlon Dr, Rock Hall

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$824,900
5 Beds ⋅ 4 Baths
Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home’s main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub. Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath. The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling inground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market. Updates to the home are available in Documents

8999 Orchard Dr, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$289,000
2 Beds ⋅ 2 Baths
This charming cottage on the outskirts of town is full of character, thoughtful updates, and endless potential to make it your own. Step inside to find beautiful wide-plank flooring in the living room, creating a warm and welcoming atmosphere. The laundry room and convenient half bath feature brand-new luxury vinyl plank flooring, with the half bath offering enough space to easily add a full-size shower or tub if desired. The kitchen has been updated with stainless steel appliances, making it both stylish and functional. Enjoy relaxing on the enclosed back porch or the inviting front porch, where you'll have a front-row seat to the town's Fourth of July parade. Upstairs, you'll find two cozy bedrooms and a full bathroom with a new vanity and brand-new luxury vinyl plank flooring. The current owners combined two bedrooms to create a spacious primary bedroom, but the layout could easily be converted back to three bedrooms if needed. The outdoor space is just as impressive, featuring a large, fully fenced backyard with a 6-foot privacy/security fence and an oversized garage/barn complete with a brand-new barn door—perfect for storage, hobbies, or a workshop.

6022 N Main St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$259,900
3 Beds ⋅ 2 Baths
Brand new home in Historic Chestertown available for move-in now. This interior unit 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 closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

115 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$240,000
3 Beds ⋅ 1 Baths
Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl plank flooring that creates a warm and inviting feel. The living area opens up to the dining area and flows into the completely remodeled kitchen that showcases crisp white soft close cabinetry, elegant quartz countertops, and stainless steel appliances; perfect for everyday living and entertaining. The home also features a renovated full bathroom, in-unit washer and dryer, and a convenient one story layout designed for comfort and accessibility. Enjoy your morning coffee or unwind at the end of the day on the covered back porch. Additional peace of mind comes with a brand new roof installed in May 2026. Whether you’re a first time homebuyer searching for a stylish, affordable, move in ready home, looking to downsize into a low maintenance property, or an investor seeking a rental opportunity in a desirable location, this home offers incredible potential. Don’t miss the chance to own a beautifully renovated home in one of Kent County’s most charming communities! Disclosure: Listing agent has an ownership interest in the entity that owns the subject property.

107 Conley Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$369,000
3 Beds ⋅ 2 Baths
Charming 3-bedroom, 2-bath rancher situated on a 0.4-acre lot in Ferry Park, just one block from Rock Hall Beach. This 1,458 sq. ft. home features an open-concept kitchen and dining area, creating a bright and inviting space for everyday living and entertaining. Located on a quiet street, yet within walking distance of local restaurants, marinas, and all that downtown Rock Hall has to offer. Enjoy the perfect combination of peaceful living and convenient access to the Chesapeake Bay lifestyle.

20725 Wilkins Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$799,000
3 Beds ⋅ 3 Baths
Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room showcasing vaulted, beamed ceilings, a fireplace, and sweeping views of the expansive rear yard. Rich hickory hardwood flooring runs throughout the kitchen, breakfast area, living room, office, and formal dining room, creating a warm and cohesive flow across the main living spaces. The formal dining room is enhanced with elegant crown molding, offering a refined setting ideal for both everyday living and entertaining. The updated gourmet kitchen features granite countertops, abundant cabinetry, and a seamless connection to the breakfast area and main living spaces, making it both functional and inviting. The private primary suite is generously sized and offers two walk-in closets along with a beautifully appointed en-suite bath featuring a luxury soaking tub, double vanity, travertine tile flooring, and a tiled walk-in shower. Two additional bedrooms provide ample closet space and share a well-appointed full bath, also finished with travertine tile flooring and a tiled shower. Outdoor living is equally impressive with extensive mature landscaping that enhances privacy and natural beauty. A stone patio and a combination of brick and Trex decks provide multiple spaces for relaxing or entertaining while enjoying the serene surroundings. Additional features include an attached two-car garage as well as a detached one-car garage, offering exceptional storage and flexibility. Ideally located just minutes from historic Chestertown and only a golf cart ride to the Chester River Yacht and Country Club and the Chester River, this exceptional home blends privacy, convenience, and luxury Eastern Shore living at its finest.

7828 Country Club Ln, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$325,000
4 Beds ⋅ 2 Baths
A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-filled sunroom that works beautifully as a screened porch when the doors are all open or as extra living space during the shoulder seasons. Two of the bedrooms sit on the upper level, while two large bedrooms flow comfortably below. Out back, the large, gently sloped corner lot offers privacy, mature trees, and room to garden, entertain, or simply enjoy a quiet afternoon. The setting feels tucked away, while the rest of Chestertown is just a short jaunt from the front door. The two-bay carport keeps your vehicles safe from the elements in the wide stone driveway. What truly sets this home apart is its condition. It has been maintained impeccably — spotlessly clean, carefully tended, and gently lived in. The HVAC system is new, and the kitchen and laundry appliances are all young as well, giving the next owner the best of both worlds: classic character on the outside, modern mechanicals where it counts. The remaining finishes offer a thoughtful canvas for the next owner to put their own stamp on it, with the confidence that the bones and the care have already been handled. Classic character, pristine condition, and convenience to it all.

200 Manor Ave, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$1,595,000
4 Beds ⋅ 2 Baths
Enjoy sweeping water views, a bulkheaded shoreline, and a lawn extending to the water's edge—an exceptional and hard-to-find combination. Boating enthusiasts will appreciate the private dock, complete with a boat lift and Jet Ski lift and the location on the river. This charming four-bedroom home blends timeless character with everyday functionality. The thoughtfully designed floor plan features a first-floor primary suite, hardwood floors throughout, and spacious living areas ideal for both relaxing and entertaining. The detached garage includes a private apartment with an additional bedroom and an additional full bathroom, offering excellent space for guests or extended family. Including the garage apartment, this property has 5 bedrooms and 3 full baths, The expansive kitchen and living area open through sliding glass doors to a patio, screened porch, and beautifully landscaped lawn all overlooking the water, creating seamless indoor-outdoor living with broad water views. Mature trees provide shade, beauty, and privacy throughout the property. Conveniently located just minutes from Georgetown, you'll enjoy easy access to restaurants and a sought-after boating destination. Whether your passion is waterskiing, wakeboarding, paddleboarding, fishing, or peaceful kayaking, this location offers endless opportunities to enjoy life on the water. This is a property that truly should be experienced in person to appreciate its unique setting, exceptional amenities, and waterfront lifestyle.

14046 Tockwogh Ln, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$339,900
3 Beds ⋅ 2 Baths
Welcome to this charming 3-bedroom, 2-bath rancher in the heart of Rock Hall! Freshly painted and move-in ready, this well-maintained home offers comfortable one-level living with a spacious and functional layout. The attached 2-car garage provides plenty of room for parking, storage, or a workshop. Whether you're looking for a year-round residence, a weekend retreat, or a place to enjoy Maryland's Eastern Shore lifestyle, this home is an excellent opportunity. Conveniently located near Rock Hall's marinas, restaurants, shops, and waterfront attractions, you'll love the small-town charm and easy access to boating, fishing, and everything this vibrant coastal community has to offer. Don't miss your chance to make this move-in-ready home your own—schedule your showing today!

5925 Williams St, Rock Hall

Listing courtesy of Century 21 Downtown. Contact:

$60,000
Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure, recording is in process. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

305 Roosevelt Dr, Chestertown

Listing courtesy of Taylor Properties. Contact:

$100,000
3 Beds ⋅ 1 Baths
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/4/2026, 10:00 AM. Bidding ends 8/6/2026, 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 1,896 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: 4104883124
$90,000
3 Beds ⋅ 1 Baths
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/4/2026, 10:00 AM. Bidding ends 8/6/2026, 1:00 PM. The list price is the suggested opening bid. Deposit: $15,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. 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: 4104883124
$264,900
3 Beds ⋅ 2 Baths
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 closet and private bath. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations.

121 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$2,300,000
A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and since renovations has had no vacancies, with solid leases in place. During the renovations every major system in the building was replaced, including new electric service, meters and new wiring throughout, all new plumbing using PEX, new water and septic service lines to the building, new energy efficient water heaters and appliances, rebuilt foundation, new Jeldwen Auralast windows, insulation and air sealing, new roof on rear portions of building (front 50-year cedar roof was replaced in early 2000s), new rear egress, a monitored fire alarm system and much more. Two of the storefronts are rented to a local arts non-profit and a yoga/pilates studio recently moved into the third commercial space. The 5 apartments consist of two 2-bedroom units and three 1-bedroom apartments. The steady income stream from the units is complemented by a generous property tax credit through 2032 (buyer to verify transferability). The property also has a Limited Lead-Free certificate, which requires only an exterior visual inspection every two years, and exempts the owner from MDE registration requirements. Complete income and expense information available after signing a confidentiality agreement. Limited photos posted for tenants' privacy. Contact for a private tour today. Please do not disrupt the businesses, they are tenants and the businesses are not part of the sale.

200 High St, Chestertown

Listing courtesy of Taylor Properties. Contact:

$199,000
2 Beds ⋅ 1 Baths
Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining area, where a sliding glass door leads to your own private concrete patio; perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and additional storage space. All appliances convey, making this home truly turnkey. Nestled in a peaceful, wooded setting between Rock Hall and Chestertown, you'll enjoy a serene atmosphere while being just minutes from schools, shopping, beaches, marinas, and local dining. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment property, this beautifully updated townhome checks all the boxes. Don't miss your opportunity to own this hidden gem!

21324 Persimmon Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$25,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/3/2026, 10:00 AM. Bidding ends 8/5/2026, 12:20 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: 4104883124
$565,000
3 Beds ⋅ 3 Baths
Light-filled home with glowing wood floors, exposed beams, skylights, and open living space. This one-level home is nestled on just under two acres! The expansive yard offers room for many activities and provides scenic views from the home. Inside, the open living space is bright and airy, with skylights, bay windows, and vaulted ceilings with exposed beams. The large kitchen has beautiful updated granite countertops, a large pantry, kitchen island with seating, and ample cabinet space. From the dining room you can explore the raised deck with a hot tub! Or enjoy meals on the screened porch, finished with water and electricity. This one-level home boasts 3 spacious bedrooms and 2.5 bathrooms. The primary bedroom has a walk-in closet and opens to a sun-filled studio or office space, which has access to the raised deck. There is an attached two-car garage with ample storage space, which could also make a great workshop. Under 15 minutes to downtown Chestertown and less than an hour to Middletown DE. Recent updates include: -Refinished hardwood floors throughout home -Granite countertops in kitchen -Updated kitchen appliances -Water treatment system - & more! Solar leased through Tesla

25124 E Kentfield Rd, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$335,000
3 Beds ⋅ 2 Baths
Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow throughout the home. The open and airy layout ensures a seamless flow between the living spaces, making it perfect for entertaining or just relaxing at home. The well-equipped laundry area comes complete with both a washer and dryer for added convenience. Take full advantage of the outdoor amenities this property has to offer. Start your mornings with coffee on the cozy screened porch or wind down your evenings on the expansive deck overlooking the fenced yard. There's plenty of space to garden, play, or simply enjoy the outdoors in privacy. The property also includes a garage, providing extra storage space and parking. This home is ideal for those seeking both charm and functionality in a serene setting. Don't miss the opportunity to call 10720 Foreston Rd your new home. Schedule your showing today to experience all that this property has to offer!

10720 Foreston Rd, Chestertown

Listing courtesy of Compass. Contact: (301) 298-1001
$480,000
5 Beds ⋅ 2 Baths
Beautifully updated while preserving its character, this charming home is ideally located just a short distance from the Rock Hall Harbor and Chesapeake Bay, offering easy access to waterfront dining, boating, and all the coastal charm Rock Hall has to offer. Relax on the spacious front porch, or entertain on the screened porch, complete with electricity and plenty of space for outdoor dining. Inside, the home seamlessly blends original character with thoughtful modern updates. The large country kitchen retains its classic charm while featuring updated stainless steel appliances. Off of the kitchen you’ll find the formal living and dining rooms, highlighted by beautiful built-in cabinetry and warm original hardwood floors that extend throughout the home. This home offers a first-floor bedroom and an updated full bathroom, offering hard-to-find single-level living. Upstairs there are four additional bedrooms and a second full bathroom, providing plenty of room for family, visitors, or a home office. The large backyard is adjacent to the civic center, providing lots of open space, yet lined with trees for privacy. Filled with warmth, charm, and modern comforts, this beautifully maintained home offers the perfect opportunity to enjoy life in one of Maryland's most beloved waterfront communities. Short distance to Main Street shops, many restaurants, marinas, and the Rock Hall beach.

21251 Chesapeake Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$225,000
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:

$140,000
3 Beds ⋅ 2 Baths
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 7/30/2026, 10:00 AM. Bidding ends 8/3/2026, 1:00 PM. The list price is the suggested opening bid. Deposit: $25,000. 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: 4104883124
$325,000
3 Beds ⋅ 3 Baths
Welcome to 21128 Striper Run, a charming 3-bedroom, 2.5-bath home nestled in the heart of Rock Hall. Offering an exceptional opportunity to own in one of Maryland's most sought-after waterfront communities, this home combines classic charm, quality features, and outstanding value. Step inside to find beautiful real hardwood flooring throughout the main level, creating warmth and character from the moment you enter. The inviting living room features a cozy gas fireplace, making it the perfect place to gather with family and friends during cooler evenings. The spacious floor plan offers comfortable living with generously sized bedrooms, including a private primary suite with its own full bath. Just off the rear of the home, you'll discover a screened porch overlooking the backyard—a peaceful space to enjoy your morning coffee, entertain guests, or simply relax while taking in the tranquil surroundings. Outside, mature landscaping and a welcoming covered front porch add to the home's curb appeal, while the quiet setting offers the small-town charm that makes Rock Hall such a desirable place to call home. Conveniently located just minutes from marinas, restaurants, shops, parks, and the Chesapeake Bay, this home offers the perfect blend of comfort, character, and Eastern Shore living. Don't miss your opportunity to make 21128 Striper Run your next home!

21128 Striper Run, Rock Hall

Listing courtesy of EXP Realty, LLC. Contact: 8888607369