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.

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.

18th century historic home in downtown Chestertown with a separate carriage house! The main home features 3 bedrooms all with en-suite baths. The carriage house has an additional 2 bedrooms and 2 baths with separate laundry and a brick patio. Entrances to the property from Queen St. and Horsey Lane, 2 driveways with plenty of parking spaces. Original wood flooring throughout much of the house. The first floor features a living room, dining room, kitchen, and half bath. New owner to add vanity and toilet to one of the upstairs baths. Second-floor laundry room. Lovely landscaping and fenced-in yard between the main house and the carriage house. Just a short walk to the heart of downtown Chestertown. Definitely a rare find.

Welcome to this charming and elegant 2 bedroom, 2.5 bathroom condo nestled in a tranquil water-oriented community near the Chester River in the historic town of Chestertown, Maryland.This gorgeous home is situated in a prime location, offering easy access to nearby shops, cafes, and restaurants. As you step inside, you'll be greeted by a warm and inviting atmosphere that seamlessly blends classic charm with modern convenience.On the main level , you'll find access from the attached garage or front porch. Off the spacious hallway you have the enclosed Washer/Dryer unit, storage closet and full bathroom. French Doors leading to the first floor study with a bedroom to the left and straight ahead to the downstairs screened in porch overlooking the serene community pond.The upper level features an open-concept living area that's perfect for entertaining. You'll love the spacious kitchen with its stainless steel appliances, sleek countertops, and ample cabinet space. The dining area is flooded with natural light, creating the perfect ambiance for family meals and gatherings with friends. Enter the upstairs porch overlooking the pond with views of the pond, this is true indoor/outdoor entertaining.The upstairs primary suite is a true retreat, complete with a luxurious en-suite bathroom featuring double sinks, shower and stunning finishes. A huge walk in closet completes this experience.This home is also ideally situated within a water-oriented community, providing easy access to boating, fishing, and other water activities. The community offers a dock, boat ramp, as well as grilling areas and a swimming pool for your enjoyment.With its stunning finishes, prime location, and luxurious amenities, this 2 bedroom, 2.5 bathroom condo is the perfect place to call home. Don't miss your chance to experience the best that Chestertown has to offer!

Sprawling brick rancher in a lovely, peaceful setting. Over 2800 sq ft. Large rooms with lots of natural light. Huge family room with cathedral ceilings and fireplace overlooking the ample rear yard. Formal living and dining rooms with hardwood floors and crown molding. HVAC is only one year old. New well pump and WIFI controlled garage door. Water heater new in 2017. Home has a grand, palatial feel with relaxing views from all the windows. Close to Chestertown and a golf cart ride to the Chester River Yacht and Country Club. High speed internet available on site.

A delightful 2 bedroom 1 bath Duplex Condo in the lovely Riverside Terrace community. The unit has been well-maintained and has breathtaking water views from the front yard and both upper and lower decks. Nestled in the heart of Historic Chestertown with easy access to town, the river, shops, Washington College, and hospital. Enjoy the beautiful tree-lined streets of this colonial-era town, the Saturday farmers' market, local theater and everything that Chestertown has to offer.

This sprawling brick rancher will take your breath away! Renovated top to bottom with updated systems, brand new stylish kitchen, luxury bathrooms, rich hardwood flooring, and a fabulous rear patio set on a large deep lot with mature trees. Single floor living with low maintenance ALL BRICK exterior, a 1 car attached garage and plenty of space for the entire gang! Minutes from Rt. 301 and commuting/shopping in Delaware, all set in a picturesque quiet small town with playground park just down the street. RECENTLY REDUCED! Come check it out today before someone else does!

Beautiful, well maintained 3 bedroom end unit townhome. Just minutes from downtown Chestertown. Features freshly refinished hardwood floors, new carpet, new roof, vaulted master bedroom, soaking tub and separate shower in the master bath, 9 foot ceilings on the first floor, walk out second story deck, and an over-sized garage with a workshop. The home is very close to shopping and restaurants. A perfect place for weekends or year-round lifestyle living.

Lovely cottage in Byford Heights, convenient location that's just minutes from the local hospital, shopping and schools. This mid-century home is move-in ready and you can take your time updating as you like...or keep it in it's current mid-century style. With 4 bedrooms and 2 full baths, there is plenty of room for a growing family. Hardwood floors throughout. Attached garage with a nice driveway provides ample parking. Large fenced in back yard with storage shed. Come see this lovely home today!

Just a few blocks away from the heart of downtown Chestertown, this bungalow could be your perfect home, or great investment property. With a large kitchen and dining room for entertaining and a living room with an abundance of natural light, this could be your happy place. The bedrooms are large, one with a half bath attached and the laundry/mud room has plenty of room for storage with a closet and cabinets.

Quiet Community, public water access block away, walking trail, Sunrise and sunset water views. Private fencing on one side, fencing for dogs in back yard. New Patio great for fire pit. Inside new wooden blinds, new luxury vinyl floor, new ceiling fan in living room, new gas stove. TAX free shopping in Middletown Delaware 15 minutes away. This is a very nice duplex.

Welcome to country living! This is a beautiful brick rancher in a beautiful country setting. Enjoy the peace and quiet of the surrounding Kent County farmland. Enjoy the beautiful Hardwood floors and natural colors as you walk through the front door. You will love the rear screened in porch, looking out over the trees and shrubs of Angelica Nurseries. Almost 1 acre of land for you to spread out on. You can stop over to Crow Vineyard and Winery and enjoy the winery and grass fed beef! You are close to Delaware and Tax Free Shopping , close to the water was well, stop down to Turner's Creek Park and Boat Ramp. Lots to do in the area for sure!

Priced To Sell Fast! Charming 2 Level Colonial, Spacious Kitchen with QUARTZ Counters, Stainless Steel Appliances, Modern Tile Backsplash, Spacious Bedrooms, New Custom Paint, Updated Bathroom, Brand New HVAC, New Flooring, Updated Lighting, Driveway, Much More!! Close to Schools, Shopping and Commuter Routes. This Will Not Last!

Lovely well-cared for home in the center of Kennedyville. 3br, 1.5ba 2 story home with large fenced in yard. New roof and flooring installed in 2019. Freshly painted and move-in ready! Should go for any financing type. Easy access to Delaware and points north. Minutes from Chestertown.

1600 SF 3 BR/2.5 BA home that shows like new located in the Village at Kennedyville offers a front porch that overlooks the community pond...full basement and garage...hardwood flooring on the first floor, beautiful cabinetry with a very spacious kitchen pantry

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.

Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all flower beds. New paint inside and out. House has had major remodels in 2000 and 2020. Town sewer. Not far from town, but the property has a private feel. Come and be amazed!! All buyers must be pre-approved.

***Photos reflect the progress as of 3 months ago. The property is now nearly completed and is simply awaiting a finishing coat of paint and a layer of sod on the newly fenced in rear yard. A superb level of craftsmanship and scope of work not to be missed.***Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored legacy 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 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.

Enjoy the waterfront lifestyle with this one floor gem perched up on the banks of the Choptank River just 10 minutes from historic Denton. Relaxation and a connection with nature are easily achieved inside and outside of the home. Outdoor living areas are abundant with a private screened-in gazebo to sit back and enjoy the wildlife, winter deck to catch some rays, and a back patio with Choptank views and no houses on the opposite shoreline. Upon walking into the home, this same goal is achieved with large windows along the water side providing sweeping views. The river room has glass all of the way around flooding the space with light and perfect for reflection or entertaining. Hardwood floors bring serious charm and warmth to the home. The primary bedroom is spacious and includes an ensuite bathroom while the other two bedrooms provide river views. An oversized 2 car garage allows extra space to mess around on your workbench and store those beloved kayaks. The large and cleared yard has a split rail fence and trees that along with the meandering paved driveway provide a sense of privacy. The community itself is very quiet and has the Jim and Mary B. Lynch Preserve adjacent which provides roughly 2 miles of walking trails and is currently managed by the Eastern Shore Land Conservancy. Make this your own tranquil Eastern Shore retreat.

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!

The luxury waterfront lifestyle is awaiting you on Spa Creek in Eastport. This updated unit has the exterior wall opened up for a picture window to let in natural light, a modern kitchen with stainless steel appliances, and a high end mini split system for silent and efficient heating and cool. The flow of the unit is one of the highlights with the kitchen and living room opening out to the covered and private outdoor deck. Moments are to be enjoyed here with views of the yachts meandering along Spa Creek with historic Annapolis in the backdrop. The community amenities include a waterfront pool to relax and enjoy the best views in town, outdoor grilling and dining area, exercise room, and sauna. Storage space is made easy with an assigned storage unit and also a bicycle room for additional space. This maintenance free condo is walking distance from the greatest marinas and dining options in Eastport and just a short water taxi ride from City Dock.

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!

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.

Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement has a workshop space and garage. Hardwood floors. Spacious family room with woodstove. Nice screened-in porch and outdoor patio with a fire pit. Home is ready for your finishing touches. Near the Chester River Yacht and Country Club and just a few minutes to historic downtown Chestertown.

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.

Discover this spacious home offering 3,100 sq ft of living space on a ½ acre lot with deeded access to the Chester River. Generously sized rooms and an inviting floor plan create an ideal setting for both everyday living and entertaining. The main level bedroom features a recently remodeled bath and large walk in closet. Enjoy the natural light and tranquil views from the sunroom, perfect for relaxing year-round.*New roof has been installed!

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 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!

Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space.Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly evenings. The eat-in kitchen provides plenty of space for casual dining, while the formal dining room offers flexibility—use it as a traditional dining area, home office, or playroom to suit your lifestyle.All three bedrooms are located on the second level, along with two full bathrooms. A convenient half bath is located just off the main living area, and a dedicated laundry room adds to the home’s practical layout. The attached two-car garage offers additional storage and convenience.Enjoy the outdoors with a private back deck, patio area, and two large side yards surrounded by beautiful landscaping—ideal for entertaining, gardening, or simply unwinding after a long day.Don’t miss your opportunity to own a well-cared-for home on a generously sized lot in a lovely neighborhood just minutes from downtown Chestertown.

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.

Spacious One-Level Living Near Downtown Chestertown & The Chester River! (PROFESSIONAL PICTURES TO COME)Welcome to this beautiful 3-bedroom, 2.5-bath home offering 1,850 sq ft of single-level living on nearly a half-acre (.46 acres) in Queen Anne’s County. Ideally located just minutes from historic downtown Chestertown and The Chester River, this property blends convenience with comfort.Step inside to find a bright, open floor plan featuring vaulted ceilings with skylights, a cozy gas fireplace, and gleaming hardwood floors throughout. The bonus room off the living area makes a perfect home office, den, or playroom.The spacious kitchen offers a pantry and ample storage, while the large utility room and numerous closets provide excellent organization options. Generously sized bathrooms add to the home’s comfort, and the oversized garage gives you plenty of room for vehicles, tools, or hobbies.Enjoy the privacy of your nearly half-acre lot, all while being close to charming shops, restaurants, marinas, and community events.This home is move-in ready and designed for easy living — a desirable find near The Chester River!

PROFESSIONAL PHOTOS COMING WK OF 9/8/25.Escape to the tranquility of rural living with this delightful 3 bedroom, 2 bath property nestled on a sprawling 1-acre parcel. Located in the heart of the countryside, this inviting home is ideal for a permanent home or as a second home to enjoy everything the Eastern Shore of Maryland has to offer, such as hunting, fishing, boating, or just a peaceful getaway. The vaulted living area is spacious and accented by a wood stove that provides both a cozy ambiance and efficient heating during colder months. The living room opens to a new 2-level outdoor deck, as well as the kitchen, perfect for entertaining family and friends. The large kitchen has an overabundance of new granite countertops, plenty of cabinets, and an island. The perfect kitchen for multiple cooks, and maybe an even larger island! The laundry room is located directly off the kitchen with access to the back yard, and to the garage. Perfect for extra storage or as a mudroom. The home features three nice sized bedrooms, including a primary suite with a full bathroom and dual closets. The property has plenty of room for a garden, boat or RV storage, or just sit back and enjoy the serenity of country living. Located just 1.5 miles from Route 301, the location is perfect for commuting north to Wilmington or Philadelphia, or head south to Annapolis and Washington DC.

Enjoy peaceful country living in this charming 3-bedroom, 2-bath rancher set on 2.5 acres backing to open farmland. The home welcomes you with a comfortable living room featuring a cozy gas fireplace and a separate dining space just off the kitchen. The kitchen offers newer appliances and opens to an enclosed sun room—a versatile space perfect for an office, playroom, art studio, or home gym.The primary bedroom includes a remodeled private bath with a walk-in shower, while two additional bedrooms share a conveniently located hall bath. Outside, you’ll find a detached 2-car garage, ideal for vehicles, storage, or stowing your kayaks for quick trips to the nearby Choptank River.The full unfinished basement has inside access from the kitchen, as well as an outside entry. The basement has been completely framed in for some rooms and a large open family room area. The basement provides another 1344 sqft of space.With 2.5 acres of open land, the property offers future potential for a pasture, small crops, a pool, or even a barn. Located just minutes from Greensboro and a short drive to Denton for shopping and dining, this home blends country charm with modern convenience.

Welcome to 204 S Church Street — a charming 3BR/3BA home in the heart of Sudlersville!This beautifully maintained and thoughtfully updated home offers comfort, style, and modern conveniences. One of its standout features is the spacious first-floor primary bedroom complete with a private en-suite bathroom, offering ease and accessibility rarely found in homes of this style. This home boasts 3-bedrooms and 3 full bathrooms and features a wrap-around porch perfect for morning coffee or evening relaxation.Inside, you'll find an inviting layout with granite countertops in the kitchen, a cozy fireplace in the living area, and dual-zone HVAC to keep you comfortable year-round. The home is equipped with a tankless water heater, ensuring endless hot water and energy efficiency.Enjoy privacy and room to play in the fully fenced-in yard, ideal for pets, gardening, or entertaining. O head over to nearby Sudlersville Park!This move-in-ready gem offers the perfect combination of small-town living and modern amenities.Don’t miss your chance to make it yours!

Meticulously maintained 3 bedroom home with additional building lots that have a well and septic on site for a total of +/- 2.24 acres. Existing home on 42 Spready Oak Road can be bought with the additional lots or sold by itself for a lower price. This house has been owned by the same person and family for many decades and has been well taken care of. Open floor plan with three bedrooms, spacious garage, nice sized backyard. Great community on a quiet street with easy access to Route 1. More info and pictures to come. Stay Tuned!!

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.

Price improvement! 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. Just 4 blocks from Chestertown's waterfront promenade. There is potential for a second bedroom upstairs. Adorable backyard. Perfect for one or two people as a full-time residence or weekend getaway.

Looking for a home that has an oversized two car garage with electric, heated floors, water, toilet hookup bonus room above and a heated Florida room? Or are you looking for a one story home with hard wood floors, a huge bonus room with heated floors and an updated kitchen all within a mile from a public ramp? You found it! Store your water toys, camper or hunting gear here! The large drive through driveway makes it simple to maneuver your large toys around as it attaches to Broad Neck and Lovely Lane! If needed, the home has a whole home generator along with an updated BAT septic system in 2015! No fear of damage in the craw-space as it was encapsulated for piece of mind! Keep your pets & those close to you safe with fencing around the home adorned by arborvitae’s for privacy! Need to work from home? No problem, it’s easy to do with talkie fiber optic internet! Within 10 minutes from downtown Chestertown, 15 minutes from Rock hall, 40 minutes from Middletown DE, 1 hour 30 minutes from the Philadelphia International Airport & 1 hour 30 minutes from BWI. Start your small town country living now! PLEASE NOTE, THE PUBLIC LANDING IS AT THE END OF BROADNECK RD AND NOT LOVELY LANE. DO NOT ENTER ANY PRIVATE STONE DRIVEWAYS.

Updated in 2024 by a loving family member & their licensed professional! 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 -

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.

Clean, classic mid-century style ranch with REAL wood floors. archways, knotty pine kitchen, a big front porch, large yard, off-street parking and bonus alley access in rear with possible room for a detached garage (buyer to verify) New upgraded electrical service and GFCI outlets, fresh paint, floors refinished and more. Walk to conveniences from this move-in ready charmer in upper Chestertown.

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! Quality Anderson windows throughout and steel entry doors. 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.

Affordable and move in ready! With fresh paint and new LVP flooring you are ready to move right in and start enjoying the freedom of home ownership. The roof & HVAC are all three years young .Tiled kitchen has newer appliances while the finished basement is ready for your work day, play room or extra living space for all of your needs. The low maintenance backyard is ready for your enjoyment with an enclosed deck for that morning coffee or evening cocktail.Hop onto 213 South for a tranquil Chesapeake City retreat or take a left and hop onto route 40 for all your daily needs, all within minutes from your doorstep!

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.

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 Investment Opportunity – Fixer-Upper on 1 Acre LotAttention DIYers, investors, and renovators! This small home, located on a beautiful 1-acre lot, is a diamond in the rough, offering endless potential for the right buyer. Nestled in the quiet, rural setting of Quaker Neck just 1.5 miles from downtown Chestertown, this property is the perfect canvas for a major rehab project.The home, which is in need of significant repairs and updates, is being sold as-is, providing a great opportunity to bring your vision to life. Whether you're looking to restore it to its original charm or transform it into something entirely new, this property offers a solid foundation for your renovation ideas.Property Highlights:* 1-acre lot with plenty of space for expansion, gardening, or outdoor activities* Small house with potential to become a cozy retreat or a profitable rental* Quiet, rural location for privacy and peace of mind* Easy access to Chestertown for shopping and Quaker Neck Landing for water fun!Please note: This home needs extensive repairs and will not qualify for traditional financing, so it's ideal for cash buyers or those with renovation experience. Buyer to perform due diligence. Sellers are willing to provide architectural drawings & site plans for their planned renovation.Don’t miss this opportunity to turn a fixer-upper into your dream home or next big project. Schedule a showing today and imagine the possibilities!

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.

(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!

Wooded lot located in the waterfront community of Chesapeake Landing. There is a voluntary HOA that you can join for a fee to join to gain access to the boat ramp and Marina. Lot backs up to farm land.

This 2 bedroom, 1 bathroom apartment is located above a garage in the Worton area. It was remodeled a few years ago and is in great shape. Still Pond Creek is across the street and there is public access just yards away. The tenant is responsible for the electric, which is split with the tenant in the house, and the oil for the heat. There is no high speed internet, but the owner has contacted Talkie and asked them to address the issue. The tenant in the house uses Atlantic Broadband and a neighbor uses Breezeline. For the first week showings will only be during Open Houses.