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$205,000
3 Beds ⋅ 1 Baths

202 Pine St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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
$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
$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
$339,900
3 Beds ⋅ 2 Baths
Nestled in the charming Rock Hall community, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 2006, this well-maintained residence features spacious living space, thoughtfully designed for modern living. The corner lot provides ample outdoor space for gardening, play, or simply enjoying the serene surroundings. Step inside to discover three inviting bedrooms and two full bathrooms, ideal for relaxation and privacy. The open layout encourages a warm flow between living areas, making it perfect for gatherings or quiet evenings at home. The attached front-entry garage and driveway provide convenient parking options, ensuring you and your guests feel right at home. Rock Hall is known for its friendly atmosphere and community spirit with local shops, restaurants, marinas, Ferry Park Beach and the Chesapeake Bay and many more area attractions. This property is not just a house; it's a place where memories are made. With its inviting design and prime location, it offers a wonderful opportunity to embrace a lifestyle of comfort and community. Don't miss your chance to make this charming home your own!

5925 Williams St, Rock Hall

Listing courtesy of Century 21 Downtown. 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
$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
$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:

$550,000
3 Beds ⋅ 2 Baths
Rare opportunity to purchase five contiguous parcels totaling 3.765± acres in a prime location near Rock Hall Harbor. Parcel 505 features an older manufactured home situated on approximately 1.27± water-view acres with scenic views of North Point Marina and Rock Hall Harbor. The additional parcels include Parcel 504 (0.853± acres), Parcel 503 (1.04± acres), Parcel 502 (0.258± acres), and Parcel 501 (0.344± acres), offering endless possibilities for expansion, investment, or future development (subject to applicable approvals). The existing home offers over 1,200 square feet of one-level living with three bedrooms and two full baths. While the home is in need of renovation and repairs, it presents an excellent opportunity to create a charming vacation retreat, retirement home, or investment property in a highly desirable waterfront community. The property is being sold As-Is. The lots are cleared and level, providing a fantastic setting to enjoy all that Rock Hall has to offer.

5666 Walnut St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$339,900
3 Beds ⋅ 2 Baths
321 West Street in Millington, Maryland is now available for you. This lovely 5-year-old home features vinyl siding, three bedrooms and 2 full bathrooms; Inside, you'll find a formal living room, a dining area, and a fully equipped kitchen with stainless steel appliances, along with a nicely sized island that offers additional space for dining. The main level also includes a laundry room with stackable washer & dryer included. Down the spiral staircase to the ground level you'll discover a one-car garage and a full unfinished basement with daylight windows - perfect for extra storage or future possibilities. Situated on a level rectangular .23 acre lot, this property offers both comfort and potential. Settlement date is negotiable and we kindly ask for a 1 hour prior notice for all showings. This home DOES HAVE an FHA assumable mortgage.

321 West St, Millington

Listing courtesy of RE/MAX Associates - Newark. Contact: (302) 453-3200
$344,000
3 Beds ⋅ 2 Baths
Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and ample cabinet space. A new HVAC system, brand-new roof, and a ONE-YEAR HOME WARRANTY provide peace of mind, allowing you to move in and enjoy your new home from day one. Outside, the expansive 1.66-acre lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provides additional space for tools, lawn equipment, or outdoor hobbies. Whether you're a first-time homebuyer, someone looking for convenient one-level living, or looking for a move-in-ready home with room to spread out, this property checks all the boxes! Conveniently located just minutes from historic downtown Chestertown, Rock Hall, nearby marinas, dining, shopping, and waterfront activities - with convenient access to major routes into Delaware and Pennsylvania - this property offers the ideal balance of peaceful rural living and easy travel. This is a rare combination of acreage, versatility, and affordability. In addition, this property has public water and sewer. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape!

9126 Fairlee Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$435,000
3 Beds ⋅ 2 Baths
Charming waterfront rancher on the Chester River! This move-in ready home features 3 bedrooms, 1.5 baths, and luxury viny plank flooring throughout. Recent upgrades include all-new appliances (2021), a 12' x 20' shed/workshop (2023), and new HVAC and viny siding (2024). Step outside to a spacious deck overlooking the river and your private dock--perfect for fishing, launching kayaks, or docking a small boat. Conveniently located just 15 minutes from both Chestertown, MD and Middletown, DE, this waterfront retreat offers the ideal blend of comfort, convenience, and outdoor enjoyment. A must-see!

31923 River Park Rd, Millington

Listing courtesy of RE/MAX Chesapeake. Contact:

$935,000
3 Beds ⋅ 3 Baths
This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance and lifestyle of the Eastern Shore with crabbing, fishing, hunting, water skiing, sailing and hikes on the nature trail all available on site. Outdoor living is huge here with multiple spaces to connect with nature and enjoy the privacy of your own waterfront sanctuary. The home is the perfect size for a weekend getaway or full time residence with a floorplan that has been expanded and opened up to accommodate the amazing views and 2026 lifestyle. Storage is a breeze with a full basement including a shop and rec room for grandkids or guests to go enjoy with privacy. One floor living makes for an easy flow with the primary suite opening to a brick patio with sliders and including both an ensuite bathroom and walk in closet. The blend of amenities on site and proximity to Chestertown's Historic District make this the perfect "magnet house" to attract friends and family or an amazing investment opportunity.

24050 Macs Ln, Worton

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

$449,000
3 Beds ⋅ 2 Baths
COMING SOON - NEW ROOF!!! Your Chesapeake Bay getaway just steps from Haven Harbour South Marina. Launch your boat, dine on the waterfront, stroll to the beach, and enjoy resort-style living from this beautifully updated home. This updated 3-bedroom, 2-bath rancher situated on an expansive lot with glimpses of the water and room to relax, entertain, and enjoy the Eastern Shore lifestyle. The spacious detached garage provides ample storage for vehicles, boats, and recreational equipment. Unwind in the cooled three-season room overlooking the fenced backyard, offering the perfect setting for gatherings with family and friends after a day on the water. Ideally located just a short walk or golf cart ride from Haven Harbour South Marina, you'll enjoy convenient access to boat slips, waterfront dining, a sandy beach, marina amenities, and breathtaking Chesapeake Bay sunsets. Whether you're seeking a year-round residence, weekend escape, or boating retreat, this property offers comfort, convenience, and the best of Rock Hall living. Wake up, walk to your boat, spend the day on the Chesapeake Bay, enjoy waterfront dining, watch the sunset, and return home to relax in your private backyard. Every day feels like you're on vacation.

21120 Green Ln, Rock Hall

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

$395,000
3 Beds ⋅ 2 Baths
Brand-new construction in the Crosby Woods Subdivision! This beautifully designed 3-bedroom, 2-bathroom home offers comfortable one-level living on a private 0.835-acre lot. The open-concept floor plan features granite countertops, a center kitchen island, pantry, stainless steel appliances, recessed lighting, and a dedicated laundry/utility room. The spacious primary suite includes a tiled private bathroom, while the additional bedrooms provide flexibility for guests, family, or a home office. Enjoy your morning coffee on the front porch or relax on the rear deck overlooking the wooded backdrop. Set back from the road and backing to a protected forest conservation area that cannot be developed, this property offers both privacy and a peaceful setting. Conveniently located just a half mile from the charming waterfront Town of Rock Hall, with its restaurants, marinas, shops, and community events.

21718 Centennial Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$415,000
3 Beds ⋅ 3 Baths
Brand-new construction in the Crosby Woods Subdivision! This thoughtfully designed 3-bedroom, 3-bath home offers convenient one-level living with an open floor plan, recessed lighting, granite countertops, a kitchen island, pantry, and stainless steel appliances. The home features two primary suites with private tiled bathrooms, including one with an additional sitting area for added comfort and flexibility. A dedicated laundry/utility room, welcoming front porch, and rear deck provide both convenience and outdoor enjoyment. Situated on a spacious 0.601-acre lot backing to trees and set back from the road, this property offers privacy while remaining just 0.5 miles from downtown Rock Hall. Don't miss the opportunity to own this beautiful new home!

21712 Centennial Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$468,000
3 Beds ⋅ 2 Baths
Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home... Living Room: Walk along the cobblestone slate path and pass through the new, classic front door into a spacious living room featuring hardwood floors that run throughout the entire house. Dining & Kitchen: A curved archway leads from the living room directly into the dining room. The dining room has an entryway to the kitchen, which could easily be opened up for an even more open feel. Porch: The dining room leads right out to a comfortable porch—the perfect spot to relax and enjoy this nice, quiet neighborhood. Mudroom & Back Entry: An oversized back entry from the breezeway leads into a large mudroom and utility space. Featuring multiple closets and laundry hookups, this functional area offers plenty of space to be creative and fit your family's needs. Bedrooms: The main floor includes three bedrooms with hardwood floors and two full bathrooms Basement: The full basement features an open space with brand-new windows that allow plenty of natural light inside. It is equipped with a new sump pump, offering a perfect blank canvas for storage, a gym, or a rec room. Utilities, Key Updates & Location The house sits on a generous lot with mature landscaping and is connected to well water and public septic. Recent mechanical and structural updates include: Brand-new roof, oil furnace paired with a new HVAC system for efficient heating and cooling. Fresh paint inside and out. You can enjoy beautiful views of the Chester River coming and going from your new home, as well as scenic river views while taking your neighborhood walks. Enjoy the convenience of being just minutes from downtown shopping and dining. Bring your design ideas to update the interior and make it your own!

25750 Collins Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$575,000
1 Beds ⋅ 2 Baths
Welcome to Wymont Park, a sought-after waterfront community on picturesque Still Pond Creek, where every day feels like a vacation on Maryland's Eastern Shore. From sipping your morning coffee while watching the sunrise over the water to enjoying breathtaking waterfront sunsets from your private floating dock, this unique property offers the lifestyle you dream about. Nestled on a beautiful waterfront lot, this versatile property features two separate living spaces, making it ideal for multi-generational living, guest accommodations, or potential rental opportunities. The charming waterfront cottage offers 1 bedroom, 1 full bath, and 1 half bath, highlighted by a spacious living room with cathedral ceilings and panoramic views of Still Pond Creek. The kitchen provides abundant cabinet and counter space, making it perfect for entertaining. Adding even more value is the oversized detached garage with a fully equipped second-floor apartment, complete with 2 bedrooms, a full kitchen, living room, and full bath. Whether you're hosting extended family, accommodating guests, or creating a private workspace, this additional living area offers endless possibilities. Step outside and discover what truly makes this property special. A large wraparound deck leads to a gazebo, creating the perfect place to relax and take in the peaceful creek views. Follow the path to your private floating dock, ideal for boating, kayaking, fishing, crabbing, paddleboarding, or simply enjoying life on the water. Located in one of Kent County's most desirable waterfront communities, this property offers the perfect combination of privacy, natural beauty, and Eastern Shore charm. Whether you're searching for a full-time waterfront residence or weekend getaway, this rare waterfront property is ready for its next owner to make it their own. Don't miss your chance to own a piece of Maryland's Eastern Shore waterfront lifestyle on Still Pond Creek.

25133 Wymont Park Rd, Worton

Listing courtesy of RE/MAX Chesapeake. Contact:

$1,195,000
4 Beds ⋅ 3 Baths
This property has an amazing amount to offer! There are 3 parcels included with a total of just over 5.5 acres. The complex includes a 4 bedroom, 2.5 baths extremely well built home on 2.68+/- acres, a .35 acre lot and a commercially zoned 2.6+/- parcel with several large outbuildings. The house also offers a spacious kitchen with center island and granite counters, a family area, laminate flooring throughout most of the house, a laundry room, screened porch and a partial basement. Heated and cooled with heat pump and propane backup. Hot water is supplied by tankless water heating system. There is a 1 car attached garage and a large open dirt floor shed for additional space close by. In the rear of the property is a 47' x 42' two bay pole building with 1 bay having a 12'+/- door. The commercial parcel has a 4 bay garage with foam insulation, an approximately 100' long x approximately 30' wide insulated workshop with 14' door that includes a full bath and laundry, a half bath, office and is heated and cooled. There is a 40' x 30' pole building in the rear of the commercial side. Last but not least is a .35+/- acre lot that has potential to be built on but would require a water and sewer allocation. This is a rare find and would be perfect for someone who has a small lawn/landscaping business and wants to expand or possibly a small excavating business and wants to live where they work. The possibilities are are there for the entrepreneur who has vision, to utilize everything this property has to offer!!

10672 Worton Rd, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$380,000
4 Beds ⋅ 2 Baths
Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It won't disappoint.

213 Byford Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$395,000
2 Beds ⋅ 1 Baths
Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gently sloped backyard to the updated bulkhead at the water's edge. Launch your kayak and explore the river and allow the tide to take you as you explore the river. When done relax indoors to an updated home that offers an open floor plan as the living room and kitchen merge as one. This home was updated several years ago so there is very little you would need to do other than adding your own personal touches. There are 2 bedrooms with wood floors and a single bath. The living room and one of the bedrooms offers access to the rear deck through sliding glass doors. There is a full basement with connecting stairs from the main level. Here is where you will find the laundry. There is plenty of storage space and could possibly be finished living space if the new owner would like to tackle the project. You will be hard pressed to find anything on the water this cute and in this price range so come take a look and decide for yourself!

31673 W Edge Rd, Millington

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$399,000
4 Beds ⋅ 2 Baths
Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT, and engineered hardwood flooring throughout. Three bedrooms, with great closet space, share a full bath. At the end of the home, you'll find the primary bedroom, with a spacious primary bath and walk-in closet. The oversized two-car garage has plenty of room for extra storage. One-floor living and a two-car garage are hard features to find in downtown Rock Hall. Outside, the possibilities are endless; there's ample room for outdoor activities or projects. Updates include: -Crawlspace encapsulation and whole house dehumidifier -10 new windows -New 25 year roof -Siding, shutters & new gutters -New flooring, engineered hardwood, LVT and carpet -Completely updated kitchen with custom cabinetry -HVAC heat pump & AC -200 amp breaker panel And more!

21424 Catholic Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$275,000
3 Beds ⋅ 1 Baths
Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in the kitchen. Has an additional coat closet as you come in the side door and a separate pantry. Nice open back yard. A solid house in proximity to town. Good place to make your own and call home, or an investment.

956 Washington Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$280,000
3 Beds ⋅ 1 Baths
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 perfect for both cooking and entertaining, while the spacious bedrooms offer comfort and tranquility. Step outside to a lovely yard with a recently installed privacy fence, ideal for family, pets, evening gatherings, or enjoying your morning coffee. This home offers the perfect combination of charm, comfort, and value. Don’t miss the opportunity to make this beautifully upgraded Cape Cod your new home.

11060 Plum Dr, Worton

Listing courtesy of Patterson-Schwartz Real Estate. Contact: 4108851606
$320,000
3 Beds ⋅ 2 Baths
Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

8706 Elm Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$288,500
3 Beds ⋅ 1 Baths
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 comfort and a bright, inviting feel to every space. Perfectly positioned to enjoy the best of summer on the Shore, you’re just a short drive (approximately 12 minutes) from the charm of historic Chestertown, the sandy shoreline at Betterton Beach, or waterfront dining and boating at Great Oak Landing. Whether your weekends are spent on the water, exploring local shops, or relaxing by the bay, this location puts it all within easy reach. If you’ve been searching for a low-maintenance home with modern updates and unbeatable access to the Shore’s favorite destinations, this one checks all the boxes.

11167 Oak Ln, Worton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact: