Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored Second Empire home on Chestertown Historic District’s most prominent corner. Water views are appreciated from two sides. Great balance of modern amenities and layout matched with historic design elements and style. The builders who took on this passion project are some of the most renowned in Kent County. 30-60 day estimated timeframe to complete upon contract acceptance. The detached garage is a huge plus with highly sought after off street parking.

This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or water toys. The river room is flooded with natural night and offers prime views of the surrounding wildlife. Stay cozy with the wood burning fireplace. Fishing and hunting are prime in this location. Feel a sense of peace and tranquility on this very private 9 acres while being able to drive to the historic district for the shops, art galleries, theatre, and restaurants in less than 10 minutes. Chestertown is located just 1.5 hours from Washington DC, Philadelphia, and Baltimore.

PROFESSIONAL PHOTOS COMING SOON- Perfectly situated on over an acre, this custom-built masterpiece offers over 4,000 SF with three fully finished levels thoughtfully designed for luxurious living and effortless entertaining.From the moment you arrive, you'll appreciate the meticulous care, craftsmanship, and extensive upgrades this home has to offer.Step inside to find a spacious formal dining room framed by elegant segmental archways, setting a warm and inviting tone. The main level flows seamlessly into the heart of the home — the gourmet kitchen — featuring soft-close cabinetry, a large center island, dual ovens, under-cabinet lighting, an induction cooktop, a spacious walk-in pantry, and a reverse osmosis water filtration system connected to both the kitchen sink and refrigerator. Adjacent to the kitchen, a cozy breakfast nook provides the perfect space for everyday meals.The expansive family room offers the ideal gathering place, complete with a pellet stove, a beautiful wet bar perfect for entertaining, and oversized sliders that fill the space with natural light. These sliders open directly to the screened-in porch — newly updated with pet-resistant screens — and lead to an attached deck, creating even more space for outdoor relaxation.Upstairs, the second level is designed for ultimate comfort.The luxurious oversized primary suite features a private propane fireplace, dual walk-in closets, and a spa-like en-suite bathroom with a luxury stone jacuzzi tub, rainfall shower, abundant natural and overhead lighting, and separate his-and-hers vanities. Two additional bedrooms with spacious closets, a large bonus room with a pellet stove (ideal for a recreation room or optional sixth bedroom), and a second full bathroom complete this floor. For added convenience, a second-floor laundry room makes everyday living even easier.The third level offers two more versatile bedrooms, a full bathroom, and access to the HVAC system — perfect for home offices, guest suites, or teen retreats.The outdoor space is just as impressive.Enjoy a partially fenced yard, ideal for children and pets to safely roam, an oversized attached 2-car garage with access to the crawl space, a detached 2-car garage that makes an excellent workshop, storage space, or man cave, plus an additional storage shed. A partial whole-house generator provides added peace of mind.And the best part? No HOA!Located just minutes from downtown Centreville's charming shops, restaurants, marina, and parks, with easy access to Route 301 and only 13 miles from the Bay Bridge, this property truly leaves no comfort feature overlooked.Welcome to a home where luxury, privacy, and convenience meet — your Eastern Shore dream awaits.

Welcome to 8543 Ingleton Rd., a beautiful one-level home located in a sought-after water access community! Offering 3 spacious bedrooms, 2.5 baths, and a dedicated office, this home is designed for comfortable living and easy entertaining. Enjoy the cozy charm of a brick wood-burning fireplace, perfect for relaxing evenings. The stylish kitchen features granite countertops and stainless steel appliances, ideal for preparing meals with ease. The open layout flows seamlessly to a large patio overlooking your private in-ground pool—an ideal spot for outdoor gatherings. Plus, take advantage of water access for boating, kayaking, and other adventures. Conveniently located between Easton and St. Michaels for all your dining and shopping pleasures. Call today to schedule your tour

Stunning farmhouse circa 1880 with lovely views of the Corsica River. Located in historic Centreville, in walking distance to many attractions. Primary suite with huge bath and dressing room, balcony with water views. Double sided brick fireplace. Gorgeous kitchen with quartz countertops and stainless steel appliances. Lots of character and charm in this house! Very close to Centreville Landing and Wharf Park, with boat and kayak launch. You'll want to tour this property!

Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and one bedroom in the walk out basement, there’s plenty of space for family and guests. The open-concept living area is perfect for gatherings, featuring ample natural light and gorgeous views of the surrounding landscape & lake! Enjoy convenience and comfort with two full bathrooms on the second, one full bath on the lower level and an additional half bath on the first, designed with modern fixtures and finishes. The finished walk-out basement provides excellent additional living space, bath/bedroom & perfect for a game room, entertainment area, or a private office. It also offers direct access to the beautiful outdoors. The property spans 2.62 acres, providing ample room for outdoor activities, gardening, or simply unwinding in nature. The partially wooded area enhances your privacy while allowing for serene nature walks right in your backyard & along the Lakes edge! Located on Urieville Lake, enjoy fishing, boating, kayaking and other recreational activities just moments from your doorstep. This private setting is perfect for those looking to escape the hustle and bustle of city life. Urieville Lake is about 35 acres in size and is shaped like the letter Y. The average depth is about 3 feet and supports a standard bass/bluegill fishery and is managed accordingly. Anglers may also occasionally catch other species including pumpkinseed sunfish, brown bullhead catfish, golden shiners and common carp. Welcome home!

Lovely colonial in Country Club Estates. The property goes back to Country Club Lane. 3 bedrooms and 3 full baths. One of the full baths is on the first floor so there is potential for a main floor bedroom. Screened-in porch overlooking the landscaped yard. 2 gas fireplaces. Open kitchen to family room. Mature landscaping. Nicely set back from the road. Well water, public sewer. Side entry garage charming shed. Beautiful wood floors. Close to town and Chester River Yacht and Country Club. Well-kept home ready for its new owners.

Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

Discover Your Dream Oasis!Welcome to this magnificent 2,042 sq. ft. home nestled on a sprawling 1.72-acre park-like setting, where tranquility meets luxury living. The 20,000-gallon in-ground saltwater pool, complete with maintenance free decking and a liner replaced in the fall of 2022, serves as the centerpiece of outdoor enjoyment. Imagine summer days spent poolside in your personal paradise!Over the past two years, this home has seen numerous upgrades that enhance its value and comfort. A brand-new septic system (2023) and well pressure tank ensure reliability and peace of mind. The attached two-car garage features a new door with epoxy flooring that is both stylish and easy to maintain. Inside, enjoy a refreshed hall bath with a new shower and flooring, fresh paint, and new lighting. New outdoor rear awnings were installed to provide generous shade over the poolside deck areas.Step inside to discover a spacious open floor plan perfect for family gatherings. The large kitchen boasts all-new appliances, a massive island, ample counter space, and plenty of cabinets to make this kitchen a culinary enthusiast’s dream. The inviting living room features a pellet stove fireplace insert, while the adjacent all-season room offers seamless access to the pool and deck area, blending indoor and outdoor living effortlessly.The primary suite is a private sanctuary, complete with a cozy sitting area, a luxurious en-suite bathroom, a generous walk-in closet, and exclusive access to a serene concrete deck by the pool — an ideal spot for a hot tub!In addition to the main house, the property includes a two-story detached garage with electric and water access, perfect for a workshop or lounge area. It even has its own separate driveway! Two additional sheds provide convenient storage for lawn and pool equipment. A chicken coop is located by the detached garage..chickens can be included!This exceptional property backs onto a wonderfully wooded area, enhancing your privacy. Once overgrown, this space has been thoughtfully cleared to create a serene retreat. With plenty of room for future additions like a pole barn, the possibilities are endless.The property is conveniently located off Route 1 for easy commuting, minutes from Bayhealth hospital, and only 23 miles from Rehobeth Beach! Do not miss the opportunity to own this stunning home, designed for both relaxation and entertaining. Schedule your private tour today and experience the perfect blend of modern upgrades and natural beauty!

Spacious Waterford Model with Over 4,800± Sq. Ft. on .32 Acre LotThis Waterford model offers exceptional living space and thoughtful design, situated on a .32-acre lot in a quiet, established community.Boasting approximately 4,800± square feet of total living area, this home features a brick front and a 2-car garage.The main level welcomes you with gorgeous hardwood floors and a gourmet kitchen equipped for culinary enthusiasts. The kitchen opens to a bright breakfast room with access to a deck overlooking a large, level yard that backs to protected woods, providing privacy and a natural setting.The cozy recreation room includes a gas fireplace, architectural columns, and a bump-out that adds extra space for relaxing or entertaining.The expansive main bedroom suite is a private retreat, featuring a sitting room, tray ceiling, and a spa-like garden bath. Additional convenience is offered with a second-floor laundry room.The home currently includes four spacious bedrooms, with potential for six total. The walk-out basement has framed rooms with windows ready for finishing to create additional bedrooms, a media room, or flexible living space. The basement also includes a finished recreation room with a full bath and loads of storage space.Additional highlights include an owned propane tank, eliminating lease concerns, and a $480 yearly HOA fee.Property details include four bedrooms with potential for six, 3.5 bathrooms, a 2-car attached garage, a .32-acre lot, approximately 4,800± square feet of living area, and a $480 yearly HOA fee.This home combines space, style, and privacy in a desirable location, offering tremendous flexibility for your lifestyle and future growth.

Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage than you could imagine. The Villages at Kennedyville is a quiet, local community. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Just a few minutes to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Seller offering $7,000 credit at closing to repair the Air Conditioning units.

FRESHLY PAINTED WHOLE EXTERIOR, GARAGE/IRON FENCING!!!!!! PHOTOS ARE GENERATED TO SHOW IDEAS!!! HOME IS CURRENTLY VACANT!!! Welcome to the Johnson-Lindsey House, a rare opportunity to own a piece of Chesapeake City’s history. Located in the heart of the Historic District, this Federal-style home was built around 1850 by Joseph W. Lindsey, the town’s sawmill and lumber yard owner. Zoned Village Center (VC), the property offers incredible flexibility for residential or commercial use, making it ideal for those looking to blend history with modern living or business potential. Situated along the route of Chesapeake City’s beloved parades and festivals, it’s just a short walk to waterfront dining, boutique shopping, and local attractions.This charming home exudes character with its classic wood-sided Federal-style architecture and distinctive bump-out picture windows on the south side. The original cast and wrought iron fence still encloses the front courtyard. The front entrance welcomes you with intact stained glass and an old-style door ringer, setting the tone for the timeless beauty within.Inside, the home showcases original hardwood flooring, tall wood windows with storm covers, and six-inch floor moldings. The light-filled foyer leads into a spacious family room with floor-to-ceiling windows and an electric fireplace wired for propane. From there, the dining room offers built-in cabinetry and access to a covered side porch. The remodeled kitchen seamlessly blends old-world charm with modern updates, featuring Quartz Silestone countertops, Italian subway tile, luxury vinyl plank flooring, a new sink, stainless steel appliances, and professionally painted cabinets. Off the kitchen, a remodeled powder room and an enclosed laundry room with an antique sink provide added convenience.The second level offers a generously sized primary suite with a fully remodeled bath, including a tile walk-in shower and luxury vinyl plank flooring. Two additional bedrooms on this floor provide space for guests, family, or a potential additional full bath if desired. The third level features another bedroom and another room currently used as storage, with ample space to add a third full bath.The backyard is a hidden retreat, offering a courtyard-style space with a side porch, a brick side patio, and a rear brick patio leading to the detached two-car garage. Very few homes in town offer garage parking, making this a rare and valuable feature. With electricity, a concrete floor, and a propane heating element, the garage could easily be transformed into a carriage house, Airbnb rental, or business space. A parking pad allows for two additional vehicles, making this property one of the few in the historic district with a backyard backing to woods and extra off-street parking.This home has been meticulously maintained with a series of updates, including five new mini-split heating and cooling units installed in 2024, along with a new storm door, professionally painted kitchen cabinets, and new ceiling fans. Recent improvements also include luxury vinyl plank flooring in the kitchen and primary bath, updated carpeting on the stairs and upper hallway, a new furnace, oil tank, and hot water heater, as well as professional interior painting. The main architectural shingle roof was replaced in 2019 with a 30-year warranty.The Johnson-Lindsey House has been featured on the Candlelight Tour and is prominently displayed on the cover of the Chesapeake City town map. Annual grant opportunities through the Maryland Historic Trust provide additional incentives for restoration and improvements. Whether you're looking for a distinctive home, a commercial opportunity, or a combination of both, this historic gem is truly one of a kind.

Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas stove, upgraded quartz countertops, solid wood cabinetry, and stylish open shelving—perfect for both cooking and entertaining. The spacious living areas boast brand-new LVP flooring, fresh finishes, and an inviting atmosphere throughout.Upstairs, the primary bedroom is a private retreat, complete with a mini-split AC/heat unit, a large dressing room, and a convenient half bath.Head downstairs to a versatile lower level, where an open-concept space offers endless possibilities—whether you need a media room, game area, crafting space, or home gym. The large laundry area and utility room provide added functionality.Step outside to your own backyard oasis, enclosed by a beautiful privacy fence. Enjoy the spacious patio, detached garage/barn, and storage shed—ideal for hobbies, storage, or workshop space.This home is completely move-in ready and packed with upgrades—all it needs is you! Don’t miss your chance to see this hidden gem—schedule your private showing today!

This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted neighborhoods. One floor living makes things a breeze with this open and easy floor plan. Serious structural updates have been performed on the home, the crawl space has been encapsulated, and the kitchen and bathrooms have been remodeled. The home was also recently had the entire exterior painted and much of the interior as well. The primary suite includes an en suite bathroom, make up parlor, and walk in closet. Outdoor living is a plus here with a partially shaded, fully fenced rear yard which includes a deck and a front private courtyard perfect for dinner parties. The detached 2 car garage allows for storing all of the toys that come along with the Eastern Shore lifestyle. This is the perfect balance with walkability, a spacious yard and the tranquility of living on a quiet cul de sac.

Welcome to your private Eastern Shore escape! Nestled on 8.36 tranquil acres just outside the charming waterfront town of Rock Hall and only 20 minutes from historic Chestertown, this beautifully updated property offers a rare blend of nature, comfort, and recreation. Surrounded by abundant wildlife, this property is a haven for hunters and nature lovers alike—ideal for deer, turkey, and waterfowl hunting right in your backyard. Birdwatchers will delight in the daily sightings of eagles, owls, and an array of coastal birds, while gardeners will appreciate the expansive space ready for planting, harvesting, and quiet reflection. Located just minutes from the Rock Hall Yacht Club and Lankford Bay Marina, and with easy access to the Chester River and the Chesapeake Bay, you're perfectly positioned to enjoy some of the region’s best boating, sailing, fishing, and crabbing. This is true Eastern Shore living at its finest. Inside, recent renovations bring modern comfort and style to this peaceful retreat. The kitchen has been completely updated with new windows, new cabinets, granite countertops, farmhouse sink, new stove and microwave, and new flooring and lighting. Ductless/mini-split units in all living areas ensure year-round climate control. The spacious family room has been expanded and remodeled to create an inviting space for gathering, with views of your wooded acreage just outside. The extension has new windows, rear door, and flooring. The downstairs bathroom has also been tastefully redone with a walk-in shower, updated flooring, and new fixtures. A new roof was completed in May 2025, offering peace of mind for years to come. A formal dining room offers flexibility—convert it into a main-level bedroom and pair it with the remodeled first-floor bath for convenient single-level living. Whether you're seeking a peaceful primary residence, a hunting lodge, or a getaway close to the water, this property has it all—scenic acreage, modern updates, and unbeatable access to the best of Maryland’s Eastern Shore. Don’t miss this opportunity to own your own piece of paradise just minutes from Rock Hall’s waterfront charm.

Fantastic Opportunity to own over 23 acres in northern Calvert County. This property is a rare combination of a private rural setting with easy city access to D.C., Annapolis or Andrews Air Force Base. Rolling farmland adjacent to dense wooded areas create a scene environment for a homestead. Recently built 40' x 70' two level metal pole barn is currently used for farm equipment storage but could be upgraded. Currently only agriculture operations. Farm and Forest District Zoning allows some commercial uses.

Back on the market at no fault of seller. Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Chesapeake. Located at the confluence of the Sassafras River and Chesapeake Bay, Betterton got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This 3 bedroom, 2 bathroom unit is being sold fully furnished and with a deep water boat slip, boat lift and jet-ski lift. As one of the larger units; it has plenty of room for the whole family. Natural light abounds with water views from both balconies or anywhere inside. Galley kitchen with granite countertops and stainless steel appliances. The main floor has an open floor plan, two bedrooms and a full bathroom. Large primary bedroom with ensuite bath and office space upstairs. Plenty of closet space throughout. Full basement has plenty of room for storing outdoor toys and equipment. Recent upgrades include: primary bathroom remodel, waterproof luxury vinyl plank flooring (original hardwoods underneath), carpets, Anderson windows, washer/dryer, water heater, interior doors, paint, and much more. Condo Association just finished renovating the decks and siding. Condo amenities include: private pier with water and electric, designated boat slip with 6,000 pound lift, community pool and kayak storage. Just a few steps from the water. This is the perfect weekend getaway or primary residence on the Eastern shore. Come see all that the Jewel of the Chesapeake has to offer.

This charming 2-bedroom, 1-bathroom waterfront home is the perfect getaway for those who love the water. Nestled along the river, it offers a peaceful and relaxing atmosphere with stunning views right from your living room, thanks to the beautiful bay windows that frame the water. Enjoy the convenience of your own private boat ramp and dock, making it easy to set off on a day of boating, fishing, or crabbing. Whether you're watching the sunrise over the river, casting a line from the dock, or simply unwinding with the soothing sounds of the water, this home is a serene retreat for nature lovers and water enthusiasts alike.

This is the one you’ve been waiting for! With over 2,100 square feet of living space, this 4-bedroom, 2-bath home sits on a spacious half-acre lot and has all the room you need—inside and out. The layout is so functional, with three bedrooms and a full bath on the main level, plus an XL living room with a cozy gas fireplace and loads of natural light.The real showstopper? The entire second floor is dedicated to the primary suite—your own private retreat! You'll love the large bathroom, walk-in closets, and the Juliet porch with gorgeous views... it’s like a breath of fresh air every single morning.There’s even more to love outside—fire up the grill and enjoy the deck and outdoor entertaining space. And if you’ve been dreaming of a workshop, gym, or storage for all the toys, you’ll flip for the 30x40 pole barn out back. Still need more? The house also has an attached garage and a separate laundry room tucked away for convenience.This one checks all the boxes—and then some. Come see it for yourself!

Coming Soon!Completely Remodeled Water Oriented Home in Easton. Gutted down to the studs, this house is turn-key ready for its new owners. New roof, new siding, new electric and plumbing, new insulation and drywall, new doors and windows, new floorings and fixtures. New HVAC. Contemporary kitchen featuring stainless steel appliances, quartz countertops, and a huge island. Even the waterfront shed has new shingles and siding. Water views of the Tred Avon River with easy access steps from your front door to launch a kayak or paddleboard. One level laid-back living on the Eastern Shore!

Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This home has been meticulously cared for and features a first floor primary bedroom with walk-in closet and ensuite bath with a massive ceramic tile shower. Large formal living room with brick fireplace flows into the kitchen / dining room combo behind with sun-room and back deck. Recent upgrades include: crawl space encapsulation, stainless steel kitchen appliances, downstairs heat pump, backyard fence, solid wood plantation shutters, automatic retractable blinds and more. Quick drive to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a brand new YMCA. Enjoy easy country living on the Eastern Shore.

Welcome to this inviting 3-bedroom, 1-bathroom townhouse nestled in the vibrant heart of Downtown Frederick. Blending character with comfort, this home offers a warm and welcoming atmosphere, perfect for both relaxing and entertaining.Step into the spacious living room, featuring cozy carpet underfoot—ideal for curling up after a long day. The rest of the home boasts beautiful hardwood flooring, adding a touch of timeless elegance throughout.Enjoy your morning coffee or unwind in the evening on the private balcony, or step outside to the back patio—perfect for small gatherings or simply enjoying the outdoors.Located just steps away from shops, dining, and the rich culture of downtown, this townhouse combines urban convenience with residential charm. Don’t miss the opportunity to make this Downtown Frederick gem your new home!

Pride in Ownership! Amazingly maintained rancher offering one-level living with open floor plan. Chill on your front porch looking out on the fields that make this area so special. Or relax on the new huge back deck while you grill or pick crabs with family and friends. This quiet setting is removed from the hustle and bustle of daily life, yet close to highway access points to DE and the Bay Bridge with easy hop on/hop off of Rte 404.Updated bathrooms with an ample-size tiled primary walk-in shower that you can party in or just meditate and relax in. The massive flat yard gives plenty of opportunities for all types of enthusiastic hobbyists and professionals to use.

A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and commercial uses—making it an ideal candidate for those looking to merge lifestyle, business, and history.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.

A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and commercial uses—making it an ideal candidate for those looking to merge lifestyle, business, and history.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.

Situated on a generous 0.653-acre lot just outside of Chestertown, this property offers the best of both worlds—proximity to town amenities with the added benefit of space and privacy. This well-maintained home features 3 bedrooms and 2.5 bathrooms, including two recently updated baths. The interior boasts a welcoming entryway, formal dining room, and a spacious kitchen equipped with an island, gas cooktop, and a cozy breakfast nook. You'll also find a dedicated laundry room with a convenient side entrance.Flooring throughout the home includes a mix of wood, tile, and carpet, while the living room offers a comfortable gathering space anchored by a working fireplace.Step outside to enjoy the expansive backyard, perfect for entertaining or relaxing. The detached two-car garage includes an additional space ideal for a workshop or home office, plus a loft area with endless possibilities.Don't miss this opportunity to enjoy country-style living just minutes from downtown Chestertown!

Welcome home to your Eco-Friendly Waterfront Sanctuary on the Chester River! Discover your own private haven along the Chester River, just minutes from Rt. 301—offering an easy commute north or south while providing a peaceful escape from the everyday. This 2.9-acre waterfront property, consisting of three separate parcels, is designed for nature lovers, outdoor enthusiasts, and those seeking a tranquil lifestyle. Enjoy peaceful river views from your oversized screened-in porch or launch your kayak or canoe from the dedicated riverside area. A concrete landing is perfect for casting a fishing line or simply unwinding in the shade. Inside, the home features a bright open floor plan with a spacious living area with cathedral ceilings, anchored by a beautiful fieldstone fireplace with gas insert. The adjoining kitchen and dining space make entertaining easy, while newer luxury vinyl plank flooring adds modern appeal. Two bedrooms with new carpet are separated by a fully remodeled bath. Stylish barn door sliders create functional transitions between the living space and the laundry area, and rear entrance. An oversized screened in porch with outdoor ceiling fan and lighting allows for peaceful relaxation in the outdoors with all the comforts of a screened in space. Imagine a candlelight dinner on an evening overlooking the river, listening to the frogs and crickets, and maybe catching some fireflies. The property has been lovingly maintained with sustainability in mind to provide the most benefit to the land, water, and wildlife. The National Wildlife Foundation has certified this property as a National Wildlife Habitat. The Audubon Society has professionally evaluated the property based on their strict requirements and officially recognized it as a Bird Friendly Habitat. Bay Wise, through the University of Maryland Extension Services has also certified that the owner has planted and maintained a sustainable landscape to promote the health of the Chesapeake Bay and its tributaries. Recent upgrades include a new septic system (2019), professionally installed swale for drainage, and a fully remediated crawl space—all enhancing both comfort and peace of mind. Whether you're hosting family, enjoying riverfront sunsets, or catching a few fish for dinner, this special property blends comfort, beauty, and environmental stewardship in one rare offering. Schedule your appointment to tour the property soon, the rest of the summer is waiting for you!

Welcome to 33 Marabou Way, a beautifully crafted new home, built just few months ago, nestled in the desirable Heron Point community—just minutes from Cambridge’s vibrant downtown shops, restaurants, and waterfront attractions.This thoughtfully designed two-story residence offers over 1,680 square feet of contemporary living space, featuring an open-concept main level ideal for entertaining and daily living. The expansive great room flows seamlessly into a designer kitchen with a center island and stainless steel appliances,—perfect for casual gatherings or family dinners.Upstairs, retreat to a private owner’s suite complete with walk-in closet and a en-suite bath. Three additional bedrooms provide generous space for family, guests, or a home office. A full laundry room and secondary bath complete the upper level for added convenience.Located in a beautiful, growing neighborhood, this home offers the perfect blend of modern comfort and Eastern Shore charm. Whether you're strolling through the historic downtown, dining along the Choptank River, or enjoying nearby parks and marinas, you'll love the convenience and lifestyle this address delivers.*For VA buyers—take advantage of a rare opportunity to assume the seller’s VA loan at a below-market interest rate, offering significant savings compared to today’s rates!

Welcome to 12776 Still Pond Road: an endearing early 20th Century Victorian in the quiet town of Still Pond. This could be the perfect Eastern Shore retreat or full time residence. Historic Charm abounds with pocket doors, bay windows, 9 foot ceilings, hardwood floors, bullseye corner moldings, mahogany front porch, oak mantels, custom built-ins, and so much more. Enjoy rolling farmland views and picturesque sunsets from the front porch swinging bench. The sun-filled formal parlor flows seamlessly through the large pocket door into the dining room and kitchen. Follow the solid-wood staircase and railing upstairs to find 3 generously sized bedrooms and a 4th bedroom or office space. Massive 3rd floor could be finished for a 4th bedroom or den / game room. Recent upgrades include: architectural shingle roof, 6 mini-split systems for central heating and air, water conditioner, water heater, fireplace mantel with propane insert, and a brand new Fuji septic system. Almost 3/4 of an acre allows plenty of space for the dogs and kids to play. Open farmland surrounds for great views from any direction. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Quick drive to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a brand new YMCA with full gym, racquet sports, lap pool, sauna, etc. Enjoy country living on the Eastern Shore.

Cute as a button in the historic district on South Kent St. This 1 bedroom, 1.5 bath home is in the center of town within walking distance to the farmers market and all the shops and restaurants. There is potential for a second bedroom upstairs. Adorable backyard. Perfect for one or two people as a full-time residence or weekend getaway.

Don't miss this beautiful, original owner, 3rd floor unit. Well-kept and ready to move in. 2 bed and 2 full baths with spacious loft that could be used as guest bedroom, office, playroom and so much more. Newly upgraded granite countertops, HVAC and wood floors. Plenty of closet storage and cathedral ceilings in main area and primary bedroom. This is a must see! Just minutes to The Avenue at White Marsh!

Fully Renovated in 2024! This charming 3-bedroom, 2-bath home offers a perfect blend of modern updates and country serenity. The main level features a convenient first-floor bedroom and full bath, ideal for aging in place. Enjoy stylish & durable vinyl plank flooring throughout and soaring cathedral ceilings upstairs that create an airy, open feel. Situated on a spacious corner lot on almost a half of an acre & a newly installed well. Whether it’s a morning coffee or an evening cocktail for watching sunsets, enjoy the cozy front porch where you can relax and take in the sweeping views of the surrounding farmland. A peaceful retreat with thoughtful upgrades—move-in ready and waiting for you! - Buyer got cold feet, walked and never scheduled inspections , terminated in default and forfeited their EMD -

Great house with good bones. Lots of the big ticket items have already been done. Situated on an oversized lot with a fully fenced yard. Large driveway for plenty of parking. 3 bedrooms and 1 bath. Central air and heat. Newer roof. BAT septic system. The house is older and needs updating. but wait until you see the basement! Huge unfinished basement that the seller uses for storage and crafting. Adds a ton of space to the house. The woodstove in the basement is capable of heating the whole house. On the Queens Anne's county side of Chestertown. Queen Anne's county schools. Being sold as-is.

Charming 3-bedroom, 1-bathroom home on 1.3 acres with room to grow! This well-maintained, one-family-owned property features recent upgrades throughout, including a new roof (2024), hot water heater (2023), new appliances and countertops (2024), fresh paint (2024), new fencing (2024), and a brand-new septic system. The oversized 2-car garage offers ample storage or workspace. The primary bedroom includes an attached bonus room, perfect for a future second full bathroom. Zoned Village Commercial, this property offers flexibility for residential or potential business use. A rare find with both comfort and opportunity!

Meticulously maintained, turn-key, one-bedroom one-bathroom Condo available just in time for summer! Open concept kitchen / living space. Spacious balcony includes hurricane storm shutters and small storage shed for beach equipment / toys. Recent upgrades include: Washer/Dryer 2023; Refrigerator 2019; Google Nest Thermostat. 2 short blocks to the Ocean and walking distance to the Iconic Ocean City boardwalk. Walking distance to many great restaurants, shopping and Jolly Roger Amusement Park, Splash Mountain, mini golf. Never rented or smoked in. Unit comes fully furnished. Condo fees include cable T.V.

Welcome to the Village of Fountainview 55+ Community! This spacious home offers 2,500+ sq. ft. of comfortable living in a sought-after active adult community. The open floor plan and serene wooded views make it perfect for relaxing or entertaining. The main level features a welcoming foyer with a half bath, a large kitchen with a center island that opens to the family room, and a main-level bedroom with dual closets and a private full bathroom. A slider from the family room leads to a deck overlooking a peaceful wooded area. The upper level includes a loft area, a second bedroom, a full bathroom, and a bonus area that could easily be converted into a third bedroom. The home also includes a full unfinished basement for additional storage or future finishing and an attached two-car garage. HOA fees are approximately $2600/Quarterly. Seller to pay one year of dues at settlementThe condo association takes care of all exterior maintenance, including lawn care, snow removal, and trash services. Community amenities include a pool and walking trails, ensuring a convenient and enjoyable lifestyle.

Charming One-Level Living Near the Chesapeake Bay!This 3-bedroom, 1-bath home offers comfortable one-level living on a spacious 0.45-acre lot just minutes from downtown Chestertown. With 1,000 sq ft of living space, the home features a bright interior, a walk-in shower, and recent updates including a plastic vapor barrier in the crawl space for peace of mind.Enjoy your mornings on the shaded back deck, overlooking a large yard with a brand-new shed—perfect for storage or hobbies. Nestled on a quiet street, this property provides easy access to the Chesapeake Bay, and with optional HOA membership, you can unlock marina privileges for boating or kayaking adventures.Whether you're looking for a weekend retreat or a full-time residence close to town and proximity to water access, this home offers the perfect blend of convenience and tranquility.

A home finished your way with what could be over 3,078 square feet of living space! Complete your new Victorian style home with the finishes & colors you enjoy! Located within a .3 mile walk to Betterton Beach and the Town Dock! Public showers, rest rooms and transient boat slips are all at your disposal! The interior of the home is a blank slate and has been protected from the elements. The home features a full concrete basement, a large kitchen space with access to the garage and the wrap around porch, formal dining, living room with an octagon window setting allowing natural light to fill the room and full bath on the 1st floor. Moving up the stairs to the 2nd floor are 3 bedrooms 2 full baths, laundry and the possibility for a large 4th bedroom or playroom/game room! The large two car garage has ample space for your bikes, jet ski and all your water toys! A builder/contractor is awaiting your call, with enough notice I can have a Builder/contractor walk through with you as you discuss your needs, likes and wants along with your budget! This is not a rehab, the home was built and never finished.

Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch.Enjoy the convenience of a patio out back—perfect for relaxing or entertaining. Located just minutes from town, you’ll love the easy access to shopping, dining, and everything Chestertown has to offer. Easy to show—schedule your tour today!

Charming Bungalow by the Bay!Discover the perfect coastal retreat in this delightful 2-bedroom bungalow, just one block from the beach! Nestled in a quaint town of only 283 residents, this home boasts beautiful hardwood ceilings, a screened front porch for relaxing evenings, and spacious back and side decks ideal for outdoor entertaining. The lower-level laundry and ample storage provide convenience, with plenty of space for kayaks, beach chairs, and more.Enjoy the town’s public docks, showers, and restrooms, or explore the nearby Hopkins Game Farm for outdoor adventures. Wine lovers will appreciate Crow Vineyard just a short drive away, while history enthusiasts can visit charming Chestertown. With a local park, tennis/pickleball courts, and a scenic picnic area, this bayfront community has something for everyone. Don’t miss your chance to own a slice of paradise!

Fantastic opportunity to own over 5 acres of buildable, level farmland with two perc approval sites. AG Zoning allows a wide range of residential, outdoor recreational and commercial uses. Property recently surveyed with a custom site plan and ready for your building plans. Property backs to 60+ acre farm in a perpetual forest conservation easement. Right of ways from 213 and neighbors driveway allow two different access points to property. Entire property is tillable. No deeded covenants or restrictions. Easy access to Route 213, Chestertown, Church Hill and Centreville. AG Tax paid by current owner. Buyer to perform own due diligence. Do not enter property without an appointment.

Two fantastic building parcels just off the Chester River. 1.36 acres total on a cul-de-sac at the end of a quiet road. Perc approved and ready for you to design your dream home on the Eastern Shore. Crabbing, fishing, swimming, birdwatching, you name it! Bring your house plans or just camp out and build a fire. Level building area sits on a small bluff well above the water: no flood zone! Public boat landing only a few blocks away. Easy access to Route 301. 90 minutes to Philadelphia, South Jersey, and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Less than 15 minutes to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Property is marked by sign. Perc approval and survey on file. Parcels sold together, not separate. Drive-bys permitted. Do not enter property without an appointment.

Welcome to 515 Main Street in the heart of Church Hill — a charming 1909 end-unit townhouse that blends classic character with great potential. This 3-bedroom, 1-bathroom home offers 1,284 square feet of living space filled with potential and character. Whether you're an investor or a buyer ready to put your personal touch on a historic property, this is a fantastic opportunity.Inside, you'll find original wood floors in some rooms, brand-new carpet in the primary bedroom, fresh flooring in the kitchen and large laundry room, and a flexible bonus room off the primary that's perfect for a home office, nursery, or walk-in closet. The bathroom and bedrooms are generously sized, and there's a partial basement with outside entry for added storage.The home sits on a 0.14-acre lot with a partly fenced yard and plenty of space to create your ideal outdoor setup. Located just a short walk from local shops, the post office, and schools, it's perfectly situated for convenience while still offering small-town charm.

Live just down the road from Fairlee Creek! Public access is less than a mile away allowing the Chesapeake Bay at your fingertips! Great Oak Marina sits at the inlet of Fairlee Creek and The Bay offering a full service resturant, marina and Tiki Beach Bar. A summer full of entertainment, boating, fishing, crabbing, jet skiing, tubing, skiing or anything else your heart deserves! Public water and sewer has been confirmed as available to purchase for each lot.Lot #2 - .259 acresLot #3 - .266 acresLot #4 - .431 acresLot #5 - .452 acres

Great chance to purchase a corner lot just across the river from Chestertown's Historic District. Sit and listen to the birds by the pond on this peaceful retreat just minutes from the town's shops, galleries, and waterfront. There aren't many more opportunities like this. Please see the documents for the perc approval and site plan.

Price improvement!!! Pretty wooded parcel recently surveyed with stakes clearly showing property boundaries. SEE DOCUMENTS for plat and aerial view. Property already has a sewer allocation. Tax record shows 3 acres but recent survey confirms 2.356 acres. There is an old collapsed trailer on site that did have electric at one time. Seller is in the process of removing the trailer and any debris around the trailer so the property will be back in pristine condition soon! This area has also been know for excellent hunting (owner recently took down a couple of deer). Property sits back off the road with a wide gravel right of way back to the parcel. The seller will meet interested parties on Georgetown Rd where a chain is across the right of way. Do not walk the property without the seller or his agent, especially during hunting season.

(Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

Discover this cozy 2-bedroom, 1-bathroom mobile home, perfect for comfortable living. Featuring a large screened-in porch, you can enjoy fresh air year-round without the hassle of bugs! Conveniently located near restaurants, shops, and essential services, this home offers both comfort and convenience. Don't miss out on this affordable and well-located gem!

One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by.County states water/sewer allocation is available. Buyer to confirm with due diligence.

Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.