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$1,750,000
5 Beds ⋅ 3 Baths
Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3 feet mlw. Take the boat to dinner at any of the five riverfront restaurant options, or catch your own dinner on the Chesapeake Bay. There’s plenty of off river activities as well, with 20x40 in-ground saltwater pool, pickleball court, spacious yard, outdoor shower, firepit, and woods. In summer, the 5 acre wildflower field bursts into color, inviting quail, butterflies and songbirds of every sort. With very easy access to points north and south, you can easily spend a day in Annapolis or zip less than 60 miles to the Philadelphia airport. The booming community of Middletown is 15 minutes away, with unlimited restaurant and shopping options. This stunning residence provides an ideal retreat for nature lovers and outdoor enthusiasts alike. Store all your toys in the attached garage and the large outbuilding. Imagine unwinding on your private dock as you enjoy friends and family playing/boating on the river. Launch your kayak or standup paddleboard directly from the property's floating dock. Relax and cool off in the pool after a great day on the river or an invigorating pickleball game. Inside, spacious living areas feature expansive windows that take full advantage of breathtaking water views, creating a light-filled and welcoming atmosphere throughout the home. Every detail has been designed for comfort, convenience, and fun, making this riverfront oasis a truly special place to call home.

14183 Roberts Dr, Golts

Listing courtesy of Gunther-McClary Real Estate. Contact:

$299,900
3 Beds ⋅ 3 Baths
Sellers are offering $5,000 in closing cost help for an acceptable offer! Easy, low-maintenance living in the heart of Rock Hall. New roof, heat, and central air in Spring 2026. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, new roof, heat, central air, and fresh paint throughout. The entry level offers a flexible bedroom or home office with en-suite bath, while the main living level features a seamless flow from kitchen to dining and family room—ideal for everyday living and entertaining. Upstairs, the primary bedroom boasts vaulted ceilings and a private balcony, alongside an additional bedroom and full bath. The garage provides ideal storage for water toys, fishing gear, or a golf cart. Whether you’re looking for a full-time residence or an easy weekend escape, this home delivers the best of Rock Hall living.

21103 Striper Run, Rock Hall

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$15,000
Half acre+ secluded wooded lot. There used to be a house on the property but county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot and there is a 16' right of way to access. Buyer to do any due diligence. Could be a great hunting property surrounded by woods and farmland!

22681 Wood Yard Ln, Chestertown

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

$339,000
5 Beds ⋅ 3 Baths

6746 Quaker Neck Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$339,000
What used to be known as the 'Pomona Store' is back on the market with fresh updates throughout! 4 bedroom house with in-law suite (additional 2 rooms on main level) and income producing unit attached! This property has so many possibilities for all types of businesses! Come and bring your imagination! House is 2444 sq ft with an additional 1100 sq ft (approx) of commercial space. Set on over half an acre in idylic Quaker Neck, yet only minutes from downtown Chestertown!

6746 Quaker Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$389,000
2 Beds ⋅ 2 Baths
THE PRICE HAS CHANGED — THE WATERFRONT LIFESTYLE HASN'T. Newly reduced $10,000! Where else can you find Chester River waterfront with a private dock at this price? Welcome to 32135 River Road in Millington, where peaceful waterfront living, beautiful views, and convenience come together. Situated on 0.53 acres along the upper Chester River, this inviting carriage house offers panoramic water views and a private dock — approximately 15 minutes from Middletown, Delaware. Here, the river becomes part of everyday life. Bring your kayaks, canoes, or paddleboards and explore the upper Chester River right from your own backyard. Spend an afternoon fishing from the dock, relax by the water, or simply enjoy the ever-changing river views. One of the property's standout features is the expansive IPE Brazilian hardwood waterfront deck. With plenty of space for outdoor dining and entertaining, it's the perfect setting for morning coffee, summer evenings with friends, or watching the sunset over the Chester River. Inside, this light-filled home features two bedrooms plus a loft and two full baths, along with granite, hardwood floors, and beautiful finishes throughout. Water views and natural light add to the relaxed waterfront atmosphere. Whether you're searching for a primary residence, weekend retreat, second home, or potential waterfront investment, the easy-to-maintain layout makes it simple to enjoy the property instead of spending your weekends maintaining it. Additional highlights include a new roof, public water and sewer, no HOA, private dock with electric, expansive IPE Brazilian hardwood deck, and 0.53-acre waterfront lot. Enjoy the tranquility of the Eastern Shore while remaining close to everyday conveniences. Middletown's shopping, restaurants, and medical facilities are approximately 15 minutes away, and convenient access to Route 301 makes travel to points north and south easy. Waterfront. Private dock. Panoramic Chester River views. IPE hardwood deck. Public utilities. No HOA. And now an even better price. Waterfront properties offering this combination of price, views, private water access, public utilities, and proximity to Middletown are increasingly difficult to find. If you've seen this property before, take another look at the new price. If you haven't, now is the time to discover it. Schedule your private showing and come experience the Chester River lifestyle for yourself.

32135 River Rd, Millington

Listing courtesy of Coldwell Banker Realty. Contact: timothy.dominick@cbmove.com
$765,900
3 Beds ⋅ 3 Baths
**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and large walk-in closet. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

#37 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$753,500
3 Beds ⋅ 3 Baths
**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private second floor balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

#36 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$786,900
3 Beds ⋅ 3 Baths
**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

#35 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$813,900
3 Beds ⋅ 4 Baths
**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

104 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,099,900
4 Beds ⋅ 4 Baths
**To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living options. Upstairs, the second primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club. Listing Office

#25 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$839,500
3 Beds ⋅ 3 Baths
**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

102 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$90,000
Nearly 4 Acres of Wooded Privacy! Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. Enjoy the peace and quiet of the woods, with plenty of deer and wildlife all around. Buyer will need to install a driveway and connect to utilities.

Georgetown Rd, Chestertown

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

$663,000
Discover 18.62 acres of waterfront land on Tavern Creek, offering 1,086 feet of shoreline and stunning natural surroundings. Zoned Resource Conservation and currently tilled, this property provides a rare opportunity for those seeking space, privacy, and water access. A small portion of the shoreline lies within the flood zone; buyer to confirm buildability.

Swan Creek Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$635,000
Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club. Enjoy the close proximity to ample shops, dining options, and Chestertown’s year-round farmers market.

108 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$2,950,000
6 Beds ⋅ 2 Baths
Located along Shipyard Creek just outside Rock Hall, this 113-acre farm offers a strong combination of productive soils, waterfront access, and long-term investment value. The property includes approximately 100 tillable acres with primarily Mattapex soils— moderately well-drained and highly rated for grain and forage production. The balance consists of woodland providing natural buffers between the creek and fields as well as quality wildlife habitat. Improvements include a 3,200 square foot Colonial Revival home and versatile shop. Both lay along 1,500 feet of shoreline steps away from a private dock offering 4'+ MLW. Farms of this size and quality rarely become available in Kent County. The property represents a solid opportunity for operators, investors, or buyers seeking a balanced agricultural and recreational tract on Maryland’s Eastern Shore. Property is subject to existing farm and hunting lease. Do not enter the property without permission from Cross Street Realtors.

Rock Hall

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$799,900
3 Beds ⋅ 4 Baths
**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

106 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,459,000
3 Beds ⋅ 3 Baths
**To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, walk-in closets, and doors to the private waterfront deck. Two additional bedrooms share a full bath. the upstairs is complemented by a convenient second-floor laundry. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porch and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Little Harbor Way Unit #1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$849,900
3 Beds ⋅ 3 Baths
**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

104 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,245,500
5 Beds ⋅ 5 Baths
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.

105 High St, Chestertown

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

$489,900
4 Beds ⋅ 3 Baths
Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot Air, Fuel Oil Heating; Central Air Conditioning. Well water pump upgraded in 2016. New, top-of-the-line “Meyers” well pump, with increased HP. Public sewer so no septic systems to deal with. Four upstairs Bedrooms. The MBR and BR2 are huge. MBR has slider door to lovely Sunroom/Sitting room. The MBR features wainscotting on all walls; crown molding; custom wide molding around all 3 doors and the closet with remote controlled ceiling fan with dimmable light. Large living room with stunning fireplace. Wide, extra-long mantle, matching storage cabinets on both sides of fireplace, large picture window and crown molding. Two full bathrooms with showers are upstairs, each with new, in 2024, quiet, yet powerful Panasonic exhaust fan and LED light. One Powder Room is downstairs. Bright and airy, extra-long dining room. Tray ceiling. dimmable LED ceiling lights on separate, inner and outer ring circuits for versatility. Ceiling centerline is pre-wired (includes 3-way switches) for one or more chandelier lights; Pass-through window to kitchen with fancy tempered glass shelf. Family room with dropped ceiling bar area. Bar sink, granite counters, gorgeous glass door cabinets, wood-burning stove, versatile lighting, and a slider door to a the main level sunroom. Modern, ample-sized kitchen with movable island. Nearly new, upscale glass cooktop/oven, dishwasher and microwave. Build-in refrigerator surrounded by cabinets. Double sink, disposal and PC workstation with shelving matching cabinet. Extraordinary lighting includes under and over cabinet lights plus a ceiling fan with fancy light globes and attractive light globes over sink. MAJOR ADDITION & REHAB done in 2013: Extended DR by 13 feet and added 2nd story sunroom/sitting room on top of DR extension Total rehab of 1st floor sunroom. Top quality, long lasting architectural roof shingle for entire house; new flashing and roof vent seals. Both sunrooms have attractive, casement-style windows for exceptional ventilation. Seven Ceiling fans with attractive lighting: MBR, BR2, BR3, 2nd story sunroom/sitting room, kitchen and 2 on the porch. All four Slider Doors (servicing the porch and the 2 sunrooms) have built-in blinds for privacy and versatile light and view control. Spacious screened porch with porch swing. Massive stone and paver patio area includes three 10x10 ft flat, paved areas for table & chairs. Large Campfire ring within the patio. Two lovely, Amish garden sheds in excellent condition and loaded with options: 12x16 ft. shed installed in 2010, and a 10x14 ft. shed installed in 2021. Huge 16x18 ft. Raised Deck using long-life Trex engineered planks; custom Pergola over one corner. Deep Shaded, 10 x 12 ft Outer Patio Area with Pergola. Mature Trees for great privacy and shade, especially around property perimeter. Three-level, split rail fence on rear and side yard property lines. (Left-side fence only is owned and maintained by the neighbor.) Extra-Wide Driveway. Paved Parking for 10 vehicles! Also suitable for camping trailer or boat.

8620 Park Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$1,125,000
Over half an acre of prime bayfront property! Build a beautiful home on popular Lawton Avenue, the Gratitude neighborhood in Rock Hall. Enjoy sunsets, spectacular views of the bay, and additional views of Swan Creek in back. Spend idyllic afternoons watching the boats sail by! Lawton Ave offers privacy, but is only a short stroll to multiple restaurants, the town beach, and many marinas; there is a private marina just across the street! Town water and sewer is already installed on site. Federal permission has been granted for a 200 ft long, 6 ft wide pier with a T-dock at the end. There would be approx. 5 ft mean low water depth at end of the pier. Buyer to obtain local permits for dock. Survey is available upon request. Two hours, or less, to Philly, South Jersey, Wilmington, Baltimore ad DC. Build your dream home on idyllic Lawton Avenue, on the Chesapeake Bay! *Online tax record does not reflect up to date property acreage.

#2 Lawton Avenue, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$30,000
Don’t miss this rare opportunity to own 1.72 acres on Galena Rd. Perfect for a commercial or business development, this property offers excellent visibility and accessibility, just off Route 313 and minutes from Massey and Galena. Nearby landmarks include the Massey Aerodrome & Air Museum, combining convenience with local charm.

12374 Galena Rd, Massey

Listing courtesy of EXP Realty, LLC. Contact: (866) 825-7169
$10,000
Build Your Dream Home on Two Expansive Lots in Chesapeake Landing! 15,000 SQFT of prime land combining Lots 191 & 192 on the south side of Clarissa Road, Block 2 of Chesapeake Landing, all under one tax ID. This is a rare opportunity to design and build your custom home in a sought-after community where nearby homes are selling in the high $600Ks! Enjoy the charm of Chestertown living, just minutes from Historic Downtown Chestertown, the scenic Chesapeake Bay, and Washington College. Conveniently close to local parks, restaurants, and waterfront amenities, this location combines tranquility with accessibility. Don’t miss this incredible chance to secure your lot and bring your dream home to life. Opportunities like this don’t come often—act now and make your vision a reality!

Clarissa Rd, Chestertown

Listing courtesy of EXP Realty, LLC. Contact: (866) 825-7169
$48,000
Come build your dream home. Located right off E Sharp Street on Chesapeake Villa is your .46 acre lot. Location is perfect to everything Rock Hall has to offer, from shops to restaurants to the water. Come check it out today. Lot has water/sewer hookup available, contact town of rock hall to confirm fees.

Sharp St, Rock Hall

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

$375,000
3 Beds ⋅ 2 Baths
UPDATE - New carpet just installed! Convenient one-level living in this 3BR, 2.5 bath rancher. The house has a desirable split bedroom layout with the primary bedroom, bath & closet off the kitchen and two bedrooms and another full bath off the other side of the house. The sun room has a propane stove and exits to a 12' x 15' deck. There's a 10' x 16' shed. Nice quiet, in-town location.

21336 Haven Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$499,999
2 Beds ⋅ 3 Baths
MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing; keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board; great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.

103 Landing Ln, Chestertown

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

$385,000
4 Beds ⋅ 3 Baths
Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

23043 Bay Shore Spur, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$469,000
2 Beds ⋅ 2 Baths
Back on the market. Spectacular Chesapeake Bay waterview condo located in the heart of Rock Hall. Beautiful upgrades include LVP flooring, tile bathrooms, kitchen cabinets, backsplash, granite countertops and appliances, plus new electric fireplace. Relax on the recently refinished Bayview deck or cuddle up next to the fireplace. The convenience of condo living lets you enjoy all the festivals and fun Rock Hall has to offer without the maintenance headaches. This unit has been used as a high quality short term rental for more than a year.

21090 W Sharp St Unit #112, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$10,000
HUGE PRICE REDUCTION on a 0.9-acre Vacant land along the Johnsontown Rd, Chestertown, MD and is conveniently located at the corner of Johnsontown Rd and Willow Oak Lane.

Johnsontown Rd, Chestertown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: