Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts!Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike. Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential.Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one side and two apartments on the other, the possibilities are boundless. While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts.This property is a bona fide fixer-upper and is exclusively offered in its current as is condition, awaiting the transformative touch of its next custodian. With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Located squarely in the Arts & Entertainment District and Enterprise Zone, both residential and commercial uses are permitted.Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture.Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!

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

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.

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.

Comfort. Nature. Luxury. All are expressed in this Contemporary waterfront home on Southeast Creek. Listen to Ospreys from your screened porch or private second floor balcony. Cool off in the pool or practice yoga in the poolside studio space. Friends from far away can come use your detached guest cottage as a tranquil retreat. Walk down your dock and go sailing with easy access to the Chester River and beyond. Gather with the ones you care about most on the central open floor plan on the main floor. Upstairs has everything you need to decompress and take in the fine Eastern Shore lifestyle. The home is less than 15 minutes from Historic Downtown Chestertown by boat or car and less than 2 hours from Washington D.C., Philadelphia, or Baltimore.

This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The floor plan was opened up to accommodate your lifestyle in 2025. New bathrooms and kitchen were custom designed. A grand 3 story staircase greets you at the foyer along with arched entryways to introduce you to the level of detail to be found throughout. The front porch allows you to sit back to watch everything happening in town or simply admire the water. The updated layout is designed for optimal flow and natural light. The primary suite captivates you with a fireplace, spacious walk in closet, and tiled shower room with views of the water from two sides. The Mansard roof allows for the full third floor. In the basement there is a partially finished space perfect for your wine cellar along with extra unfinished tidy space for storage. There is also a fenced in rear yard perfect for intimate gatherings, pets, and gardening. Off street parking is a huge plus as well with a detached garage connecting to the rear yard. Due to this property's grandeur and scope of work, the sellers are going to let you decide on some finishes to make you feel you spend wisely. Allowance lists to be provided to interested parties. Turn this important and updated piece of Chestertown History into your Legacy property.

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.

Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living room with fireplace. The upstairs has 4 bedrooms including the primary suite with dressing room, private balcony and en suite bathroom equipped with radiant floor heat. Half of the third floor is finished as well with a mini split and skylights for hobbies while the other half is perfect for storage. Not that storage is a issue with this full basement including a workout room and dance studio as well. The lush grass yard is tastefully landscaped and easily enjoyed with privacy on your rear deck. Keep your cars and favorite toys clean with the 3 car garage. Spare no detail and live luxuriously in this Eastern Shore gem.

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!

Welcome to this beautifully maintained 4-bedroom, 3-bath home offering serene views of the Chesapeake Bay in the quiet and friendly community of Tolchester Estates.This wonderful home is nestled just 10–15 minutes from the cities of Chestertown and Rock Hall. This close proximity provides access to shopping, restaurants, a farmers market, theater and local arts. The area abounds with hunting, fishing, crabbing, boating, and much more. A local full-service marina with a restaurant, summer concerts, and a beach is only 5 minutes away.The main level of the home provides a light-filled open layout featuring gleaming hardwood floors on the main level and expansive windows offering lovely views to the Chesapeake Bay. The beautiful living room features new built-in custom cabinetry flanking a cozy gas fireplace, with seamless flow into an all-season sunroom and multiple decks—perfect for entertaining or unwinding after a hectic day.The living room adjoins a fully appointed chef’s kitchen with a gas cooktop, wall ovens, refrigerator, and dishwasher. There is plenty of cabinetry, along with an inviting eat-in area and high-top breakfast bar with seating, and access to the decks for grilling. A formal dining room just around the corner offers additional space for hosting.The first-floor primary suite is a private retreat with direct deck access and water views. The ensuite bath features a double vanity, jet tub, and separate shower, complemented by a walk-in closet and laundry area for ultimate convenience. A second bedroom with an attached full bath completes the main level, with both bedrooms updated with new carpet in 2023.Upstairs, you'll find newer luxury vinyl plank flooring, 2 additional bedrooms, and a full bath. The generously sized water facing bedroom provides a great view and is sized for a suite full of furnishings or is ideal for a “bunkhouse” type setup, ideal for guests or family. The rear 4th bedroom completes the upper level and features an entry into the walk-in attic storage.The oversized, rear-entry 2-car garage includes built-in cabinetry and provides 1 of 2 inside entries to a full unfinished basement—ready for your vision. Recent updates include a brand-new roof the week of May 5, 2025), a propane-fired whole-house generator, custom living room cabinetry, upgraded insulation, all new multi-faceted water treatment systems, and custom structural enhancements.Don’t miss this rare opportunity to own a peaceful bay-view sanctuary with modern upgrades and timeless charm. Your Chesapeake escape awaits!

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!

Countryside elegance at its finest in this sprawling and updated Dutch Colonial in the rolling farmlands of Worton. A tasteful blend of traditional colonial character along with modern amenities creates your perfect setting for a peaceful retreat. The primary suite includes cathedral ceilings, private balcony, and a beautifully remodeled en suite bathroom. The spacious living room gracefully flows out to a private screened rear porch. The den or office has wonderful built-ins and feels cozy with one of the 2 fireplaces in the residence. Stainless steel appliances and natural light make this spacious kitchen a hit for entertaining large groups. A half bathroom on the first floor also is perfect for receiving guests. Upstairs are two large bedrooms and another full bathroom. The basement is perfect for storage or your next project and one side even has a garage! Outdoor living space is the true hit with this property. Life can be enjoyed on the full length covered front porch with Ipe flooring or on the large back deck. Thoughtfully curated landscaping has created a tranquil oasis including a fenced in rear yard perfect for pets. The property is located just a short drive from Historic Chestertown and less than 2 hours from Philadelphia, Washington DC, and Baltimore.

Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2 more bedrooms and an office. Updates include: new carpet primary BR, garage door 2024, roof Dec 2022. Enjoy the serene ambiance from the large deck, overlooking a picturesque pond with not one, but two enchanting waterfalls. The soothing sound of cascading water creates a tranquil atmosphere, perfect for relaxation and unwinding. This property is a true retreat, offering an idyllic escape right in your backyard. Located just minutes from the Chester River and Chestertown’s historic district.

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.

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!

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 deeded deep water boat slip. 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.

**OPEN HOUSE 6/22 **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!

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. Property was previously perc'd and approved for a commercial building but will need to be reevaluated for residential uses.

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. More info and photos to come.

**OPEN HOUSE JUNE 14TH**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 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.

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. Wether is a morning coffee or an evening cocktail for watching sunsets, enjoy the cozy front porch where you can relax and take in sweeping views of the surrounding farmland. A peaceful retreat with thoughtful upgrades—move-in ready and waiting for you! * PROFESSIONAL PHOTOS COMING*

Charming Single-Level Living in a Prime Location!Welcome to this inviting single-family home, offering the ease of one-level living in a beautifully designed space. This residence features a thoughtfully laid-out floor plan with ample natural light and open, flowing spaces. The heart of the home is the spacious living area, seamlessly connected to a large kitchen with room for an island, perfect for entertaining. With 3 bedrooms and 2 full bathrooms, each room is designed for comfort and convenience, making it ideal for anyone seeking a low-maintenance lifestyle either as a first time home buyer or for aging in place. A split bedroom layout is ideal as the main bedroom suite adorns the entire one side of the home with a walk in closet and bath. New carpet has been installed in the living room as of 12/3/24, The home is located a few minutes from Killens Pond State Park, Harrington Raceway & Casino, and a short distance to Delaware Beaches. Make your appointment today to take advantage of owning single level living in a quiet neighborhood.

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.

Open house! This Saturday, April 19th 11am-1pm. Brand new stainless steel appliances, fresh paint and newly stained deck! Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open kitchen with granite counters and a kitchen island. Sliders to patio and to upper level deck. Large yard. Half bath on the main floor. 3 bedrooms and 2 full baths on the upper floor. Family room in the basement as well as an oversized 1 car garage with lots of storage. Roof has recently been replaced. Overall, a great unit in a great location!

Back on market because financing fell through! Move right in and make yourself at home! Located just a stones throw from Worton Park, Kent County Community Center and Kent County High School, this 3 bedroom 1 bathroom home has been updated, well maintained and nicely landscaped. The property is on town water and sewer and is .87 acres comprised of 3 lots zoned village. There are sewer allocations available in the area so subdivision may be possible. The size of the property also provides plenty of room for a garage, pole barn or an addition. Check with the County for more information. From the front of the house there are views of farm fields and in the back there are historic train tracks. Enjoy the rural character of the location with the convenience of being just minutes from Chestertown.

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! 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.

Well maintained charming bungalow in North Elkton. Open floor plan and two large bedrooms. Laundry room and utility room in the back. Spacious backyard enclosed with a new privacy fence and a shed for garden tools. Perfect for a first time home buyer or investor. Recent improvements include: all windows replaced with double pane insulated vinyl and heat treated windows in front, mini-split system for central heat and air, privacy fence in backyard, water heater. Two driveways allow for plenty of parking and back fence can be opened to pull all the way through. Steps from shops and restaurants. Easy commuting to Route 95 or 40.

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!

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.

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!

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!

Great 3 Bedroom 2.5 Bath home located in Chestertown within close proximity of the college, downtown, and local shopping. The house will be available starting July 1st. There is a credit check, background check and rental application needed. No pets, no smoking. Excellent credit is required.

Brand new, barely lived in, 3 bedrooms, 2 full baths and move in ready! Townhouse end unit. All on one floor, neutral colors, LVP floors in kitchen, living area and hall with carpet in the bedrooms. The kitchen has granite countertops, large island, stainless steel appliances plus washer and dryer in the unit. Located on a quiet road with private driveway and back door sliders off the primary bedroom to a small patio and nice yard space. Convenient to grocery stores, many conveniences, restaurants, YMCA and hospital. No HOA fee. Only a few minutes away from charming downtown Chestertown. **Tenants will be responsible for electric, town water and sewer, internet services and lawn maintenance. To qualify, applicants need a credit score of 600 or higher with no delinquent accounts, and a monthly income close to three times the rent. Additionally, all household members over the age of 18 must complete an application.**

Spacious and well-maintained 4-bedroom, 1.5-bath home available for rent in the heart of Chestertown! This charming residence offers plenty of living space and character, including beautiful hardwood floors throughout, a cozy layout, and lots of natural light.Enjoy the convenience of two off-street parking spots, and in-unit laundry in the basement.Located just a short walk to downtown shops, restaurants, Washington College, and local parks — you’ll love the community and small-town charm.**Tenants will be responsible for electric, town water and sewer, and internet services. To qualify, applicants need a credit score of 600 or higher with no delinquent accounts, and a monthly income close to three times the rent. Additionally, all household members over the age of 18 must complete an application.**