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$2,900,000
Historic Radcliffe Mill, located on the Eastern Shore of Maryland, dates back to 1891 and is on the National Register of Historic Places. Restoration of the flex complex was completed in 2007 and is comprised of the 4-story mill building and the annex/seed house. Set in Chestertown on 2.3-acres next to Radcliffe Creek, the site has been important to Kent County agriculture since 1694. (Main photo courtesy of Tyler Campbell Photography). The main building features a reception area with an elevator leading to business offices, while the sushi-thai restaurant, is just off the main lobby. Radcliffe Studios is located in the Seed House offering a yoga studio, cafe, and several small wellness businesses. Property amenities include a 61-car park, a loading dock and an original grain elevator. South Fork Studio Landscape was part of the design team working on the project. The convenient location is within walking distance of Washington College and the Wayne Gilchrest Walking Trail and is just one-mile from downtown Chestertown. Founded in 1706, Chestertown is set on the banks of the Chester River. Stroll the brick sidewalks lined with lovely period homes, shops, theatre, galleries and dining options including an Oyster Bar, cafes and restaurants. Residents and visitors alike enjoy the farmers market, Fountain Park, Chester River Walk, annual Tea Party Festival and public cruises on the Chester River Packet. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia, and 1-hour from Wilmington.

860 High St, Chestertown

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

$1,995,000
5 Beds ⋅ 4 Baths
Welcome to paradise! This incredible estate, situated on a bluff overlooking the Fairlee River will take your breath away. Situated in a peaceful, private setting, this masterpiece of a home is graced by soaring ceilings and abundant windows, incredible new renovations throughout such as the gourmet kitchen and spa-like baths, all thoughtfully designed to maximize it's best feature, the glorious water views. The finishes by Colebrook Designs (who you can find on Instagram) are some of the best you'll ever see The entryway draws you into the thoughtfully designed living area, created to delight the most descriminating host. The beautifully appointed great room adjacent to the chefs kitchen creates a dramatic focal point on the main level, accompanied by an elegant formal dining room and a secondary living area, which features another fireplace to create those cozy evening settings. The fully customized kitchen features amazing amenities such as luxury Cafe' appliances, many upgrades in the soft close cabinetry, the island that seats 7+ people, all with expansive water views. Upstairs, you'll find an open lounge area which opens to a spacious second floor balcony, one of many glorious outdoor spaces. Moving on to the bedrooms, if you desire easy one floor living this home provides a great opportunity featuring the most amazing first floor suite. With a soaking tub and walk in shower in the bathroom that's graced by skylights, and expansive water views from the bedroom, this is a space that you'll never want to leave. Dual walk in closets and a seperate seating area rounds out this magical space. Upstairs you'll find the two spacious guest bedrooms, served by another gorgeous full bath featuring a soaking tub of its own to round out the second floor. Back downstairs before you head outside you'll find a spacious laundry area, and a thoughfully designed first floor guest bath that also features a walk in shower for your convenience to clean up after enjoying watersports in the river. And through the breezeway to the 2 car garage, where you'll find a separate room that's set up as a gym, featuring it's own handbuild sauna! And finally outside, you'll adore the spacious cedar deck that's perfectly positioned to enjoy the broad water views. Besides the deck, this space features a custom outdoor kitchen and a covered patio area perfectly positioned for cool breezes to flow through on hot summer days, all set in the beautiful, mature landscaping that bursts into a riot of color in the spring and summertime. The newly rebuild dock features 5 boat slips as well as multiple lifts for jet skis and a boat, and super easy access to the great expanse of the Chesapeake, with 5-6 feet MLW depth at the dock. All of this is set in the beautiful neighborhood of Great Oak Landing, which features access to a 350 slip marina, restaurants, a community pool, beach, and a 9 hole executive golf course, all of which are a short walk or golf cart ride away, all for an annual membership fee of only $350! This will make an amazing home for its next owners, and would also make an amazing vacation rental for those who would choose to not live here full time. Make the most of your summers to come in this glorious home, come take a tour while it's still available!

10108 3rd Point Rd, Chestertown

Listing courtesy of Keller Williams Elite. Contact: (717) 553-2500
$1,499,000
3 Beds ⋅ 4 Baths
Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the community! This exquisite three-bedroom, three-and-a-half-bath home offers luxurious living and breathtaking, panoramic views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Little Harbor Way Unit #1, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$1,099,999
3 Beds ⋅ 3 Baths
Sportsmans Paradise..... 3 Bed 2.5 Bath Cape Cod nestled on 36 acres, Granite kitchen counters, stainless appliances, hard wood flooring, Open floor plan concept, mud/laundry room off the side entrance. First floor Primary bedroom, 2 bedrooms upstairs with walk in closets and a jack & jill bathroom. Spare office room on 2nd floor as well. Out back a nice patio area & fire pit overlooking your Large 40'x60'x17' pole barn with 2 lean toos and a additional storage shed. On to the rest of the 36 Acres there is a trail running back to the main wooded area, 4 different access points to the property from both roads. There is 2 stocked fishing ponds, a waterfowl impoundment, theres been lots of time, money and effort spent here improving the habitat for for wildlife, including multiple food plots of clover a fruit orchard, buffer grasses & cypress trees. This property offers great deer, turkey, and waterfowl hunting and is a sportsmans dream come true. " Buy land, there not making it anymore "

411 Pine Tree Rd, Chestertown

Listing courtesy of Taylor Properties. Contact:

$998,500
5 Beds ⋅ 4 Baths
Welcome to the Esau Watkins House (circa 1739), believed to be the earliest remaining dwelling on the Chester River in Historic Chestertown, the capitol of Kent County, Maryland. Rarely does a home of this significance become available in the heart of Chestertown’s famed Water Street district. This five-bedroom, three-and-one-half-bath historic gem offers captivating, unobstructed views of the unspoiled Chester River. Notable features of this home include extensive random width wood plank flooring, proportionally balanced trim work, gorgeous scalloped built-in corner cupboards, a sun-filled riverside enclosed porch, a living room with wood burning fireplace, spacious second-floor primary suite, adequate “step-in” closets, and storage, walk out full basement, lush waterside garden, and sea-walled frontage with pier deck for water access. This highly sought-after location is within a short, pet-friendly, walking distance to several well-reviewed restaurants, two delicious bakeries, intriguing boutique shops/galleries, and the highly acclaimed Downtown Chestertown Farmer’s Market. The Chester River offers endless watersports, world-class crabbing, fishing, kayaking, and undisturbed shoreline exploration. Chestertown is home to Washington College, the Chestertown Tea Party, and the sailing ship “Sultana.” Come Enjoy! Please note that the property history and previous listing information is incorrect!

109 Water St N, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$995,000
3 Beds ⋅ 4 Baths
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

230 S Water St Unit #1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$995,000
3 Beds ⋅ 4 Baths
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants.

226 S Water St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$950,000
3 Beds ⋅ 4 Baths
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

228 S Water St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$949,900
4 Beds ⋅ 4 Baths
Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite four-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #25, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$895,000
Commercial Development Site on busy MD Rte 213, Prime location across from Washington College Campus. Approx 1 acre, zoned C-3. Suitable for retail, restaurant, service uses. Water and sewer available.

515 Washington Ave, Chestertown

Listing courtesy of EShore. Contact:

$859,900
3 Beds ⋅ 4 Baths
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.

212 N Queen St, Chestertown

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

$850,000
2 Beds ⋅ 3 Baths
Waterfront and low maintenance located less than 1 mile from Historic Chestertown! The home is thoughtfully designed with an attached garage and first floor ensuite to allow for main level living (present or future). The abundance of natural light that fills the interior highlights the architectural detail throughout and is further balanced by the neutral paint scheme and hardwood flooring. **Open floor plan, soft close cabinetry, 2 propane fireplaces, expansive unobstructed water views of the Chester, and more...

318 Landing Ln Unit #30, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$815,000
3 Beds ⋅ 4 Baths
Check out Chester River Landing's newest construction! This middle unit, three bedroom, three and a half bath townhouse is spacious and has incredible views of the Chester River. Built with the finest finishes, the main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #12, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$805,000
3 Beds ⋅ 4 Baths
Check out Chester River Landing's newest construction! This three bedroom, three and a half bath, townhouse is a spacious end unit with incredible views of the Chester River and is built with the finest finishes. The main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #11, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$799,000
4 Beds ⋅ 2 Baths
New price! Wait until you see this beautiful renovation! No detail has been overlooked in this open-concept historic Chestertown gem. The owners were able to achieve the perfect balance of updating the living space while maintaining the charm and character of the original house. Tall ceilings and thick moldings with high-end modern amenities give this property a one-of-a-kind feel. New kitchen with a large island, quartz countertops, gorgeous GE Cafe appliances. Both baths have been renovated and are some of the most beautiful we've seen. New HVAC, new roof and flashing. off-street parking with a garage/shed. The first floor features a living room, an open kitchen and dining area, a full bath, and a huge laundry/mud room. Doors lead out to the fenced-in yard and new patio. Behind the yard is an alley with off-street parking and the renovated garage/shed. The second floor has 3 bedrooms, an additional room that could be a bedroom if desired, and another stunning full bath. An additional bedroom or bonus room on the finished 3rd floor. Much of the original hardwood flooring remains. Fireplaces are non-functional but gas inserts could be added. Walking distance to all that historic Chestertown has to offer.

207 N Queen St, Chestertown

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

$775,000
4 Beds ⋅ 3 Baths
Welcome to 121 Lyons Lane in Chestertown! This stunning property offers the best of both worlds, a waterfront private wooded setting on 3.5 acres AND located within walking distance to the quaint shops and restaurants of Chestertown! Watch the sunset over Fishing Creek from the wrap-around front porch with the Chester River and downtown in the distance. The home offers 4 bedrooms, 2.5 bathrooms and a detached studio. The living room features hardwood floors made from reclaimed wood from Camden Yards baseball stadium in Baltimore, fireplace with pretty wood mantel, crown molding and beautiful water views. The dining room features crown molding and chair rail molding, providing an elegant space for gatherings. The sunroom, with its wrap-around windows, allows you to immerse yourself in the beauty of the outdoors. The kitchen features newer stainless steel appliances, new tile flooring, and a spacious Williams Sonoma marble top island with seating. The pantry closet offers ample storage space, and the laundry mudroom area from the garage provides added convenience. The main level also includes a powder room and a primary bedroom with an en-suite bathroom, ideal for one floor living! Upstairs, you'll find three spacious bedrooms, and generously sized closets. The bathroom has recently been gorgeously remodeled and showcases a large glass shower with a picture window overlooking the water, a separate soaking tub, a dual sink vanity and designer tile. Outside, you'll discover a screened-in gazebo, perfect for enjoying outdoor dining while taking in the tranquil surroundings. A separate fully-finished studio, equipped with its own climate system, offers endless possibilities as a home office, gym, or art studio. Situated on a private lot, this home also features outdoor sheds for additional storage, in addition to the large two-car garage with storage systems. The circular driveway provides convenience and ample parking. Three separate parcels combine to make the 3.5 acres, including one perc approved lot, which offers flexibility and potential for future expansion, guest house, etc. Just under a mile away is historic Chestertown with its quaint shops, delightful restaurants, vibrant Farmer's Market, and waterfront parks - all within walking distance. The sellers have an approved permit for pier that is valid until 2024 and can convey with the property. Chestertown Marina is also approximately 1 mile away. Don’t miss this incredibly special waterfront property!

121 Lyons Lane, Chestertown

Listing courtesy of Washington Fine Properties. Contact: info@wfp.com
$649,000
Owner is offering six (6) months rent free. This property backs to Kent Countries largest industrial park which has several buildings constructed and occupied and many under construction. This Industrial is changing the business climate of Chestertown tremendous growth is in process. Pizza Hut restaurant has recently closed and contains an already in place layout for a new restaurant to re-brand this location. The building has the additional potential to be renovated into a mixed use facility with a single or multiple MEDICAL tenants. The location is nearby to town, which is home to Washington College, and is located only 90 minutes from Baltimore, Philadelphia and Washington,D.C. This property backs to Kent Countries largest industrial park which has several buildings constructed and occupied and many under construction.

903 Washington Ave, Chestertown

Listing courtesy of EXIT On The Bay. Contact: (410) 304-2011
$625,000
4 Beds ⋅ 3 Baths
Quaint, historic home in Great Oak Landing with tons of character. Double front doors and double parlors. Randon width 18th-century floors. Sunroom and screened-in porch. 2 gas fireplaces. Fenced-in yard, gorgeous gardens with pond, deck, and brick patio. 2 bedrooms and 2 full baths on the main level. Additional 2 bedrooms and full bath on the second floor. Also on the second floor is a vast storage or bonus room. A leisurely stroll to Great Oak Marina and a golf course. $350/year road maintenance fee. Voluntary community civic association and Great Oak Marina have offered privileges to paid community members ($100 annual dues), including 9 hole golf course, boat ramp, pool, and beaches. Boat slips are available to rent.

10230 John Carvill Rd, Chestertown

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

$625,000
3 Beds ⋅ 3 Baths
Enjoy water views from this Eastern Shore two-story brick condo that is just a short walk from downtown Historic Chestertown parks, shops and dining. A major renovation in 2014 included a new kitchen and new baths. Bright with natural light and designed for first floor living, the home offers a spacious primary master suite, living room, half bath, kitchen and dining area opening to a deck. The inviting living room features a cathedral ceiling and wood-burning fireplace. The second floor has a comfortable, flexible layout with two bedrooms and a full bath. Another sought-after amenity is a detached over size two-car garage with storage. Founded in 1706, Chestertown is set on the banks of the Chester River and is home to Washington College. Brick sidewalks are lined with lovely period homes, shops, bakeries, galleries, theatre, oyster bar and restaurants. Residents and visitors alike enjoy the river walk, parks, farmers market, walking trails, community activities and annual festivals. River cruises are available on the Chester River Packet and Schooner Sultana. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia and 1-hour from Wilmington.

407 S Cross St Unit #4, Chestertown

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

$600,000
4 Beds ⋅ 2 Baths
BUY THIS AWESOME HOME FOR LESS THAN $2,800 PER MONTH OR TRADE! SPECIAL FINANCING AVAILABLE: RATES LESS THAN 4.6% FOR THOSE WHO QUALIFY. OCCUPYING A VAST, RESIDENTIAL BLOCK ALREADY SUBDIVIDED FOR FUTURE DEVELOPMENT, THIS UNIQUE HOME BLENDS COUNTRY SERENITY AND URBAN CONVENIENCE WITH THE HISTORIC CHESTERTOWN JUST A FEW MINUTES AWAY. IT IS A SUPER RARE OFFERING WITH 10 ACRES OF LAND. INCLUDING HORSE STABLES A LARGE BARN AND SPACE TO STORE YOUR FARM EQUPMENT. IMAGINE ALL THE POTENTIAL! THE RESIDENCE ENJOYS OVER 2,300 SF OF FINISHED LIVING SPACE FEATURING A 3-SEASONS ROOM IN FRONT, A LARGE KITCHEN WITH PANTRY AND LAUNDRY AREA, BEAUTIFUL WOOD FLOORS IN MAIN AREAS, MUD ROOM AT THE BACK, PLUS NEW ROOF, BACK UP GENERATOR, AND DECK FOR ENTERTAINING. THE GENEROUS MASTER SUITE EASILY TRANSITIONS TO THE OUTDOOR THROUGH A SLIDER. BONUS ROOMS INCLUDE A SMALL OFFICE OFF OF THE FAMILY ROOM AND A SECOND OFFICE SPACE RIGHT IN THE HALL. IT'S IDYLLIC FOR THOSE LOOKING FOR PEACE AND PRIVACY. RENOVATE FOR COMFORT OR EXPLORE ITS DEVELOPMENT POTENTIAL. OPEN HOUSE EVERY DAY - CALL FOR TIMES!

24543 Chestertown Rd, Chestertown

Listing courtesy of Your Home Sold Guaranteed Realty. Contact: (410) 793-1616
$598,500
4 Beds ⋅ 2 Baths
Your dream house awaits in the most perfect location! This delightful custom built home, being offered on one of the most sought after streets in Downtown Chestertown, and perfectly situated at the 'quiet end' of Queen Street, is only one block to the Marina, restaurants/shops, and overlooks Wilmer Park, with the Chester River beyond. Although this home has the true look of a an Period Colonial Home, it was actually newly constructed in 2006, on the original footprint of an older historic home. The owners have not only built , but meticulously cared for, and loved it throughout the years, being located so conveniently to all the things everyone loves about Historic Chestertown. As you walk up to the house you will find the porches very inviting and you will get so much enjoyment being out there at any time of day. As you come in you will find a front living room with a wood burning fireplace that adds warmth and enjoyment to the whole home. through to a cozy dining room or extended living room . Next, a pristine kitchen, refreshing and full of light, which offers plenty of storage and counter space. There's a main level laundry offered and then what could be a Primary Bedroom at the back of the house (with a full bath), or it can be used as a family room, as it is currently now. Through out the house which is not standard, but was thoughtfully and custom added, are very ample, oversized closet spaces for plenty of storage. You will also find an upstairs staircase to the floored attic that allows plenty of room for all your additional storage needs. On the second floor you have the option for a very spacious primary bedroom at the back of the house and an additional 2 rooms which have been a guest room and office . Through out the house you will find gorgeous plantation shutters to help allow the sun in when you want or help keep it out. Very tastefully done. As you settle into the heart of downtown you will be able to enjoy the Traditional Farmers Market on Saturdays , The well known Tea Party Festival , The Dickens Holiday Celebration and Down Rigging Weekend, just to name a few. The Garfield Center is always a favorite with a line up of theatrical shows and musical attractions. You will quickly fall into your favorite enjoyments and pass times that Chestertown has to offer . Some of the favorites of downtown will be the coffee spots, eateries and dining options which can all be with in within a few minute walk. Many details about this house can still be shared but come see and feel the welcome and the ease of a well built costume home that has been well taken care off and ease of low maintenance.

223 S Queen St, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$595,000
3 Beds ⋅ 3 Baths
You will appreciate peaceful living in this waterfront community on the Chester River just minutes from historic Chestertown.. A light-filled and spacious open floor plan is wonderful for enjoying the elegant interior amenities. You will also want to sun bathe or swim at the lovely pool, stroll the shell walking paths throughout the community and along the shoreline, go kayaking from the community dock, or just sit back and relax while enjoying the Eastern Shore lifestyle.

209 Landing Ln, Chestertown

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

$569,000
2 Beds ⋅ 3 Baths
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!

103 Landing Ln, Chestertown

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

$495,000
Ready to build and level 2.7 acre commercial lot in Chestertown. Check with Town regarding water/sewer hookup and potential uses in C-1 Zoning. Sign posted.

125 Scheeler Rd, Chestertown

Listing courtesy of The Hogans Agency Inc.. Contact: (410) 778-1665
$495,000
Rare offering - 2.7 acres with C-1 Zoning ready to build on. Prime corner commercial lot with many possibilities. Check with the Town as to potential uses - store, hotel, gas station - and public water/sewer hookup. Motivated Sellers have priced to sell.

125 Scheeler Rd, Chestertown

Listing courtesy of The Hogans Agency Inc.. Contact: (410) 778-1665
$492,000
3 Beds ⋅ 3 Baths
Ranch home located on a large lot in Orchard Hill. New kitchen, new shingles, paint and other custom improvements. Located one mile from historic Chestertown, several miles to the Chesapeake Bay, minutes to the Chester River and Chester River Yacht and Country Club. The exterior of this home is low maintenance.

8983 Orchard Dr, Chestertown

Listing courtesy of Davis Real Estate, Inc.. Contact: 410-778-2610
$450,000
3 Beds ⋅ 2 Baths
Lovely rancher on over 3/4 of an acre. Private country setting but only 10 minutes to town. Bedrooms are split with the owner's suite on one side and the two additional bedrooms on the other side. Nice wood stove in the living room for warm, cozy heat during the winter. Beautiful hardwood floors throughout most of the house. Formal dining room. Deck off the living room with pretty views of the backyard. Large unfinished basement. $300 road maintenance fee. Whole house generator with a transfer switch. There is a landing on the river at the end of Venaringham Lane, just a quarter mile from the house. Basement can be finished to be one large room or 2 rooms with a bath for in laws or children.

27336 Preston Ln, Chestertown

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

$440,000
4 Beds ⋅ 3 Baths
Welcome to this charming colonial home nestled on a sprawling corner lot where timeless elegance meets modern comforts. With 4 bedrooms and 2.5 baths, this residence offers ample space for both relaxation and entertainment. As you approach the property, you'll be captivated by its picturesque curb appeal. The classic colonial architecture sets the stage for the delightful surprises awaiting within. Step through the front door and into a world of warmth and sophistication. The main level greets you with dual living rooms guiding you effortlessly throughout the downstairs living space. Newly installed vinyl plank flooring stretches out before you, enhancing the home's inviting atmosphere. The heart of this home is the meticulously designed galley kitchen, featuring gorgeous custom cabinetry, gleaming countertops, and modern appliances. Whether you're a culinary enthusiast or simply enjoy gathering with loved ones, this space will surely inspire memorable moments. The adjacent dining area offers a haven for shared meals, with natural light streaming through the windows, casting a soft glow on the room. It's the perfect spot to savor your morning coffee or host a lively dinner party. When it's time to unwind, make your way to the cozy living room. Bathed in natural light and adorned with a charming fireplace, this space invites relaxation and intimate conversations with friends and family. Retreat to the upper level, where you'll find the luxurious primary suite. The spacious bedroom with walk-in closet creates a haven for restful nights. The en-suite bathroom offers a tranquil escape, complete with modern fixtures, a soaking tub, and a separate shower. Three additional well-appointed bedrooms provide ample space for family, guests, or creative pursuits. Each room exudes a welcoming ambiance, with ample closet space and large windows that bathe the rooms in natural light. The exterior of the home is equally enchanting, with the large corner lot providing endless possibilities for outdoor enjoyment. Whether you envision creating a vibrant garden oasis or hosting lively barbecues, this expansive space will inspire your imagination. Recent upgrades have been thoughtfully implemented, including a roof with a transferrable 50-year warranty, a new garage door, and a hot water heater - all just three years old. Additionally, the 2-zone heating and cooling system ensure year-round comfort and energy efficiency. Located in a desirable neighborhood of Crestview, this home offers convenience and tranquility in equal measure. Explore nearby parks, schools, and shopping destinations, all within easy reach. In summary, this colonial gem combines classic allure with modern amenities, creating a haven you'll be proud to call home. Don't miss your chance to experience the beauty and comfort this property has to offer.

106 Northgate Dr, Chestertown

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

$439,900
3 Beds ⋅ 2 Baths
NEW CONSTRUCTION ON AN ACRE LOT. JUST ABOUT DONE. 3 BEDROOM 2 BATH RANCHER. STAINLESS STEEL APPLIANES WITH ISLAND IN KITCHEN. VINYL PLANKING FLOORING IN LIVING ROOM AND KITCHEN. CATHEDRAL CEILING IN MAIN PART OF HOUSE. BACKS TO FARM LAND. OPEN FLOOR PLAN. IF YOU HAVE WANTED A NEW HOUSE BUT DONT HAVE THE TIME TO BUILD HERE IS YOUR CHANCE.

209 Blakefield Dr, Chestertown

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

$385,945
5 Beds ⋅ 4 Baths
Currently being built in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms and is positioned on a corner homesite. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, classic birch cabinets, a large corner pantry and a peninsula island with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers a fifth bedroom and a third full bathroom, as well as a flex room that could be used for storage. The Verona includes a washer and dryer, luxury vinyl plank flooring, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

107 Flying Cloud Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488