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

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.

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

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

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

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

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

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

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!

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

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

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.

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.

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!

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.

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

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

Welcome to 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. 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 -

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.

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.

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

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

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

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

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

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.

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!

Beautiful cape in a peaceful setting. 3 bed and 2 baths. Updated kitchen. Fireplace with built in book shelves in the living room. Lovely screened in porch overlooking the private back yard. Credit score of at least 700 required. No pets. No smoking.