Chestertown MD Homes For Sale

More photos and a floor plan to follow along with descriptive commentary. Meanwhile, this property is immediately adjacent to the beautifully designed and well-crafted new houses of Cannon Square ($600-800,000+).

410 Cannon St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$439,900

5 Beds ⋅ 4 Baths

Welcome to Your Forever Home! Step into luxury with over 3,000 sqft of living space, and that's just the beginning. As you explore this exquisite property, you'll discover an almost fully finished basement that adds an additional 1,300 sqft of potential. Upon entering, be greeted by the elegance of the entry level, which boasts an office, a charming dining room, a well-appointed kitchen, and a spacious Great room. Venture upstairs, where you'll find three generously sized bedrooms in one direction, and in the other, a massive primary bedroom that will sweep you off your feet. The grand primary bathroom and walk-in closet are sure to captivate you and make you feel right at home. But that's not all – head down to the almost fully finished basement, which could easily be a home of its own. With a game room, a comfortable bedroom, a well-appointed bathroom, and a cozy family room, it's the perfect space for an in-law suite. This is more than a house; it's a place where memories are made, and dreams come true. Welcome to your forever home.

110 Camelot Dr, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (443) 978-3330

$12,000

Kent County Health Dept has no record of perc

LOTS 253-254 Carimon Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$110,000

2 Beds ⋅ 1 Baths

Estate sale - Investor alert- major rehab needed - sold strictly AS IS - price to sell quickly- country location with in minutes of Chestertown - NO Well or Septic records on file - contact county for more information.

6292 Broad Neck Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact: (443) 274-1900

$460,000

This spacious Colonial home in Coventry Farms is within the town limits of Historical Chestertown in Kent County on the Eastern Shore of Maryland. Its location is conveniently located to many waterways for watercraft pleasure, marinas, public beach, dining, cultural activities and Washington College. The two-story open front foyer home of over 3000 SF offers an open floor plan which includes a sun room with an abundance of natural light overlooking the in-ground pool in the fenced rear yard. The home also offers a separate/formal dining room, finished rec room on the lower level and a 2-car attached garage. This three bedroom, two and one-half bath home is the perfect space for family and entertaining friends.

129 Trafford Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$875,000

This contemporary waterfront property offers the perfect blend of modern living and waterfront serenity. The open floor plan affords views of Mill Creek from every room. The first floor features a three sided fireplace, a gorgeous great room with floor to ceiling windows/doors, gourmet kitchen which opens to the dining area, plus two bedrooms and two full baths. Upstairs you have a cozy loft area perfect for curling up with a book or for tv. There's also another bedroom and full bath and an office with a balcony looking over Mill Creek. Most of the furniture will convey! If you enjoy outdoor living this property is for you. There's a screened porch - the perfect setting for a crab feast! Plus a wrap around deck for relaxing and entertaining. The property includes private access to Mill Creek, making it perfect for boating, kayaking, and other water activities. And for those needing deeper water you will find Worton Creek Marina right around the bend! UPDATE: The health department has confirmed that it is possible to put a garage on the parcel where the septic system is located

10761 Kasota Rd, Chestertown

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

$299,500

Looking for that quiet location in a water access community? You will feel right at home in this 3 bedroom, 2 bath cape in Chesapeake Landing just minutes outside Chestertown and Rock Hall. From the front door to the back deck, the owners have taken great care and it shines through. Easy to maintain LVP flooring runs throughout the main floor. There's a bedroom and full bath as well as the kitchen with table space, dinging room with barn doors and a nice size living room, all located on the main floor. Two large bedrooms and hall bath are located on the second floor. Outdoors you will find a nice back yard for play and an abundance of parking including the electrical hook up for that RV. The storage shed is the perfect spot to keep the toys, lawn tools and equipment. Join the voluntary community association and enjoy the water access with the marinas and boat launch.

23240 Clarissa Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact: (443) 274-1900

$385,000

The BEST of in-town Chestertown living! Single level living in this open floor plan, custom built home. Hardwood floors, spacious primary suite with walk-in closet, fully fenced back yard, impeccably maintained. Two blocks from Washington College & Kent County Middle School, one block from Baily Park Dog Park, a short jaunt into Downtown Chestertown restaurants, shops, & the waterfront. More pictures coming on 9/21, ready for showings on 9/22... schedule soon!

411 Greenwood Ave, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344

$234,900

Come by this lovely BRAND NEW middle unit home in a Triplex in Historic Chestertown, available for move in in October. This home features Luxury Vinyl Flooring throughout, White Shaker Cabinets, Granite Counters, Spacious Living Room, Eat in Kitchen area, covered patio off the kitchen, spacious bedrooms including a large primary bedroom suite and much more! These homes are selling faster than they can be built, so come by today and take advantage of this opportunity while it lasts. There are only a few of these homes left ! Special financing programs available, including Zero Down payment loans and closing costs assistance programs so you can own this home for less than renting. Home is delivered at the asking price the way you see it in the photos with the exception of the siding color, which may be different.

114 Metcalf Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact: (443) 292-9250

$449,000

Nestled within the desirable community of College Heights, this charming Colonial-style home offers the perfect blend of classic design and modern convenience. Step inside to discover a well-designed floor plan that seamlessly integrates both form and function. The spacious living room features hardwood floors, large windows that flood the space with natural light, and a cozy fireplace that's perfect for chilly evenings. The updated kitchen offers an abundance of storage and prep space and opens to the formal dining room, both with original hardwood floors. Retreat to the three generous bedrooms, each designed to offer a peaceful haven for rest and relaxation. The master suite features a private bathroom two closets. This property also includes a two-car garage, dual zone heating and cooling, and a basement that offers ample storage space or potential for customization to fit your needs, as well as a screened back porch and large deck area, and a fenced back yard. This home has been lovingly cared for, with updates that blend seamlessly with its classic character. You'll find peace of mind in knowing that it's move-in ready.

209 E Campus Ave, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$495,000

Three bedroom ranch home in very desirable neighborhood. Located in between downtown Chestertown and the Country Club.

7920 Carriage Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$95,000

3 Beds ⋅ 1 Baths

Classic 2 story located in Chestertown Historic District steps away from downtown shopping and restaurants ! Deep back yard with large shade tree. Large kitchen, separate dining room, and front living room just off the front porch. 2 or 3 bedrooms possible. Very aggressive pricing for historic district !

109 S College Ave, Chestertown

Listing courtesy of Maryland Realty Connection. Contact:

$2,200,000

4 Beds ⋅ 5 Baths

Custom built house on the East Fork of Langford Creek set on 8+ acres with a private dock. This is the first time the house has been for sale; original owners. It was built by Patrick Jones and designed by architects Dunning & Dunning from Swathmore, PA. Beautiful sunsets. It captures the lay out of the property and celebrates the water from every window. There is deep water (4.5 MLW, buyer to verify). 7-ton boat lift. Sunken living room with vaulted ceiling. White Oak floors through much of the house. Designed for outdoor living. There is a Deck, screened in porch, covered front porch. 2 car garage off the kitchen. Storage area above the garage with separate outside access. Huge basement, partially finished. Plenty of room for guests, a workshop, and a garage door for all the toys. Shown by appointment only. No drive by's please. High speed internet.

23829 E Fork Dr, Chestertown

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

$215,000

2 Beds ⋅ 1 Baths

MOVE IN READY!! Adorable, Affordable & 2 Blocks from the Chesapeake Bay! You don't want to miss this 2 Bedroom, 1 Bathroom home in Tolchester Estates! Featuring a Brand New Roof (2022), New Dishwasher (2023), New Washer (2022), beautifully updated, tiled Bathroom, lovely pergo wood flooring, bright & inviting Kitchen & cozy Family Room. Enjoy fishing or relaxing at the Private Community Beach or head over to Tolchester Marina & The Shanty Beach Bar right down the road for entertainment, dining and boating! Great location just 10 minutes from downtown Chestertown or Rock Hall, where you can enjoy tons of marinas, restaurants, shops & regular events! Not a thing to do but move in and enjoy everything this home and location has to offer! Whether this is your full time residence or 2nd home this adorable home has so much to offer! Come see for yourself!

21217 Texas Ave, Chestertown

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

$225,000

This property is perc approved and ready for your fresh ideas. With 2 different zonings you can turn your dreams into a reality! This almost 6-acre parcel located on the corner of RT 544 and Pine Tree Rd has so many possibilities. With Suburban Estate and Village Center zoning here are just a few things you could envision on this large parcel of land. This property is approved for 2, you saw that right, 2 four-bedroom homes! Just think you could live in one, rent the other or have a mini family compound. Don't want to build 2 homes? That's okay the property also allows for a commercial zoning, ever thought of starting your own business? You could build your dream home and walk to your business all on the same property! But don't wait, properties like this don't come around often. Set your appointment to see this one today!

112 Pine Tree Rd, Chestertown

Listing courtesy of Rosendale Realty. Contact:

$249,900

Priced To Sell Fast! Charming Updated 1 Level Rambler, Spacious Kitchen with QUARTZ Counters, Stainless Steel Appliances, Spacious Bedrooms, New Custom Paint, Updated Bathrooms, New Flooring, New Lighting, Fenced Backyard, Storage Shed, Much More!! Close to Schools, Shopping, and Commuter Routes. This Will Not Last!

10755 Glenola Rd, Chestertown

Listing courtesy of ANR Realty, LLC. Contact: 877-328-4400

$474,900

5 Beds ⋅ 4 Baths

Bask in the beauty of this incredible 1920s home in downtown Chestertown! At 2890 square feet, this freshly painted 5 bedroom, 3.5 bathroom property has tons of space and an oversized lot featuring a secluded backyard with mature trees, fire pit, and off-street parking, most of which are very rare to find downtown! The many updates include a brand new HVAC system and hot water heater; updated electric, new slider doors, cooktop, combination wall ovens, dishwasher, and 2nd floor bath fixtures along with a meticulously restored stairway in the entry hall. Other features include original hardwood floors on the first floor & stairway & newel post, some original windows, refinished floors on first floor, original hardwood floors on the second floor, freshly painted and repaired dormers, privacy fence, revitalized front door, and much more! Aside from the fantastic interior space, you'll fall in love with the charming front porch and lovely balcony off the second story primary bedroom. The exterior is further improved with new topsoil, grass seed, fertilizer, straw, and flowers. 204 N Mill is located on a quiet street close to downtown shops, Washington College, waterfront, restaurants, farmer's market and shopping. Whether a residence or an AirBnb, this home has endless possibilities!

204 Mill St, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$179,900

3 Beds ⋅ 1 Baths

INVESTOR ALERT!!! Bring all offers! You definitely want a property in the highly sought-after Chester Harbor community, located in historic Chestertown, home of Washington College! Portions of this community are waterfront and waterview. Use the beauty of your imagination to renovate this home into an income producing AirBnb, long-term rental, or to use as your vacation home oasis where you can enjoy kayaking or fishing at the pier! Very close to parks and recreation and a short ride to Centreville and Kingstown.

149 Longfellow Dr, Chestertown

Listing courtesy of Keller Williams Flagship of Maryland. Contact:

$47,500

Build on almost an acre with the water & sewer allocation paid for & just steps away from the public ramp at Fairlee Creek! Trailer your toy & enjoy the perfect spot for tubing, skiing, wakeboarding, knee boarding, kayaking, paddle boarding, crabbing or whatever your heart desires. Great Oak Marina & Jelly Fish Joel’s sits at the head of the creek with easy access to the Chesapeake Bay! Enjoy the public beach where you can swim, eat, drink & listen to a band! Anchor out for the day or dock at Jelly’s! Rock Hall & Historic Chestertown are just a short drive away. * 45 minutes to Middletown DE * 1 hour to Easton MD * 1 hr 20 minutes to Philadelphia Airport * 1 hr 45 minutes to BWI Airport

Georgetown Rd, Chestertown

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

$187,777

21123 Montana Avenue is located in a Chesapeake Bay water oriented community on the Eastern Shore . You can make this a full time residence or your get away space. You have water views as you drive up and enter your driveway. In Tolchester Estates you will have access to the private community beach, boat ramp and you will be welcomed to the community center that holds a variety of events through out the year. All ready to move into and you can be in to enjoy the Fall season. This home offers a split floor plan. Main bedroom and full bath on the left as you come in the front door and then two bedrooms and full bath to the right. Open living room, kitchen, eat in kitchen and extended bar for stools. Out back you have a deck and the back door where you can enter into the mud room/laundry room. The screen porch will let you relax looking out into a nice size private back yard with mature trees and deer to watch. Home is being sold as is.

21123 Montana, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$59,000

One of the last buildable lots in Chestertown with public sewer and water hookup available. Cleared and ready to build your dream home. No historic district regulations. Rear lot line was adjusted in 2021 allowing 16 more feet to build behind the beautiful Japanese Maple tree. Just a few minutes walk to the heart of downtown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Wonder at the historic architecture and enjoy local shopping, restaurants, art galleries, music stores, and waterfront walkways and parks. Chestertown is home to many festivals and the local Farmer's Market on Saturdays. 30 minutes to Middletown, Delaware and tax-free shopping. 90 minutes to Baltimore and/or Washington, D.C. 60 minutes to Philadelphia. 90 minutes to Delaware Beaches. Survey from 2021 on file.

709 High St, Chestertown

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

$245,000

THIS CHARMING HOME OFFERS A COZY LIVING SPACE THAT MAXIMIZES EFFICIENCY! Its modern 2023 renovations provide an inviting atmosphere with plenty of natural lighting throughout! The home features a primary bedroom with attached bath, kitchen with plenty of storage space, and a back yard patio, great for relaxing or entertaining! Minutes from local Rock Hall marinas, Waterman's Crab House, Harbor Shack, and other dining, this home is perfect for a full-time residence or vacation home.

8899 Georgetown Rd, Chestertown

Listing courtesy of Keller Williams Realty Delmarva. Contact: (410) 524-6400

$10,000

Chesapeake Landing has a voluntary Home Owners Association which offers access to Worton Creek. Parcel has failed perc.

Millbrook Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$129,000

3 Beds ⋅ 1 Baths

This hidden gem is ready for its new owner!

301 Burchard Sawmill Rd, Chestertown

Listing courtesy of Sky Realty. Contact: (302) 525-0004

$739,000

4 Beds ⋅ 4 Baths

Beautiful home with stately presence on a large corner parcel within Chestertown's Historic District. Mill Street offers privacy and quiet living in the heart of town. Lovely landscaped courtyard and a sunny patio/deck. Gracious flowing floor plan with beautiful, large, squared rooms that retain many of their original design elements. The original part of the house dates to the 1840's . You will love the wood floors throughout, large gourmet kitchen with soapstone countertops and ample storage, including a spacious walk-in pantry. Formal dining and sitting room with a fireplace, as well as flex room for entertaining. Upstairs there is a large primary bedroom with a walk-in closet, a smaller bedroom with a connected bathroom, as well as a third bedroom and additional full bath. This second level also boasts an office and library or tv room. The third floor has a large fourth bedroom and plenty of attic space for storage. The property offers the rare in-town feature of an enchanting courtyard/garden which leads to an oversized garage/workshop. Plenty of off-street parking with an additional driveway facing Cannon street. 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, a bakery, galleries, theatre, oyster bar and restaurants. Stroll down to the Chester River waterfront, the farmers market on Saturday morning, or Zelda’s Speakeasy and multiple restaurants in the evening. Just a block from the Chestertown's Rail Trail, which connects multiple parks and is great for walking or biking. A short walk to wonderful shops, restaurants, bakeries and less than a block to a natural foods grocery store, this corner home on Mill Street offers privacy and spacious living, yet is only steps away from all Chestertown has to offer. Chestertown is located about 90 minutes from Washington, D.C. Philadelphia and South Jersey, and 1-hour from Wilmington.

112 S Mill St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$225,000

8.27 +/- acres in Queen Anne's County ready for your dream home! One perk approved building site and two more pending the next "wet season" for testing. This size residential lot is hard to come by and with the possibility for more than one building site! Existing structure on property is of no value.

327 Pine Tree Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$224,500

2 Beds ⋅ 2 Baths

Why RENT???? Wonderful opportunity to obtain a well maintained single family home with water/beach/boat ramp access. Locate on off of the main road and surrounded by wooded lots on all but one side. Home is a split bedroom design with 2 full baths. Many updates were done in 2021. Seller is willing to consider settlement assistance with acceptable offer. Currently tenant occupied - photos are prior to occupancy. Tenant may consider staying if desired. Please DO NOT enter drive- showings are by appointment only.

21286 Maine Ave, Chestertown

Listing courtesy of L. C. Parker Real Estate. Contact:

$249,999

This charming three-bedroom rancher sounds like the perfect home for those who love to entertain guests. The split bedroom concept, open floor plan, and large backyard make it an excellent choice for hosting gatherings. The separate laundry room is a convenient feature, and the kitchen's great looking counters and island add a touch of elegance. The front door is located on the west/northwest side, and there is a ramp to the side door for easy accessibility. Plus, being just minutes from downtown historic Chestertown and historic Washington College makes this property an ideal location for those who appreciate history and culture. While it looks great, it's important to note that the property is being sold in as-is condition.

7499 Poplar Ave, Chestertown

Listing courtesy of Realty Navigator. Contact: (410) 643-3404

$249,990

The move-in ready interior townhome in The Village at Chestertown! This two-story Jefferson is an open-concept townhome with three bedrooms and two and a half bathrooms. The first floor is spacious with a large, thoughtfully designed kitchen with modern gray cabinets. stainless steel appliances, a storage closet and a peninsula island with space for seating. The kitchen is open to the living and dining area providing your ideal space to entertain. The first floor also offers a powder room. The second floor has three large bedrooms, each with plenty of closet space, a hall bathroom, a linen closet, and a laundry closet with an included washer and dryer. The owner’s suite offers privacy away from the other bedrooms and features its own full bathroom and a walk-in closet. The included white blind package and the exclusive Smart Home® package will give you complete peace of mind. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

237 Island Lark Way, Chestertown

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

$250,990

New home, under construction, this two-story Jefferson is an open-concept townhome with three bedrooms and two and a half bathrooms. The first floor is spacious with a large, thoughtfully designed kitchen with beautiful white cabinets. stainless steel appliances, a storage closet and a peninsula island with space for seating. The kitchen is open to the living and dining area providing your ideal space to entertain. The first floor also offers a powder room. The second floor has three large bedrooms, each with plenty of closet space, a hall bathroom, a linen closet, and a laundry closet with an included washer and dryer. The owner’s suite offers privacy away from the other bedrooms and features its own full bathroom and a walk-in closet. The included white blind package and the exclusive Smart Home® package will give you complete peace of mind. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

241 Island Lark Way, Chestertown

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

$148,500

Lot 5- A one acre building lot in the desirable Prestwick community on the golf course. No builder tie-in. Public sewer and well water. Surrounded by mature beech trees. Roads will have final paving after the last few lots are sold. Prestwick is a 12 lot community next to Chester River Yacht and Country Club, 4 miles from Chestertown. A perfect place to build your dream home.

Muirfield Dr, Chestertown

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

$251,990

New townhome, under construction in the Village at Chestertown! This two-story Jefferson is an open-concept townhome with three bedrooms and two and a half bathrooms. The first floor is spacious with a large, thoughtfully designed kitchen with stylish white cabinets. stainless steel appliances, a storage closet and a peninsula island with space for seating. The kitchen is open to the living and dining area providing your ideal space to entertain. The first floor also offers a powder room. The second floor has three large bedrooms, each with plenty of closet space, a hall bathroom, a linen closet, and a laundry closet with an included washer and dryer. The owner’s suite offers privacy away from the other bedrooms and features its own full bathroom and a walk-in closet. The included white blind package and the exclusive Smart Home® package will give 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.

239 Island Lark Way, Chestertown

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

$309,900

Plenty of natural light brightens this 4 bedroom, 2 bath split level home located in Foxley Manor. There are gleaming wood floors throughout most of this home. There are 3 bedrooms on the upper level and one large bedroom on the lower level with access to the backyard. The main level offers a living room/dining room "L" that flows into the "galley style" kitchen. The roof and mini-splits are relatively new. There is a partial, unimproved basement. Property has most recently been used as a short term Airbnb rental. Property is on a corner lot and close to shopping, restaurants, movies and more!!

100 Malone Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$375,000

5 Beds ⋅ 2 Baths

Welcome to 210 Rosin Dr in the desirable Chester Harbor neighborhood. As you walk in, you will notice the spacious open layout and the beautiful Bamboo flooring throughout the main level. There is ample space is this home with over 2300 sf including the full basement (rare for this area). Both bathrooms and kitchen have been tastefully updated. Enjoy watching the wildlife and winter water views of Rosin Creek/Chester River from the back deck. Roof (2011), HVAC (2017), Water Heater (2017). The basement features 3 additional bedrooms and a full bath. Chester Harbor Community has a voluntary HOA which offers community events, beaches and a playground. Chestertown is quite the charming Eastern Shore town! Come check it out.

210 Rosin Dr, Chestertown

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690

$65,000

Almost 1 acre ready for you to build. Foundation from the original structure still on site as is the public water & sewer at the property. Contact the county for more information . Owner had plans to build but life took a different direction. His loss is your gain. Pick up where the seller left off. A lot of sweat equity went into this property. Driveway stone in place. Owner cleared the property making room for your dream. Country living with town utilities. The best of both worlds. *Recent survey done showing lot is .957 acres. Tax record reflects 1 acre.

8858 Georgetown Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact: (443) 274-1900

$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:

$145,000

5.34 acre lot with 2 percs. Close to Chestertown, Church Hill, Centreville and more. Great place to build your dream home

Church Hill ( Lot 2) Rd, Chestertown

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

$15,000

Redfield Rd, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

$25,000

Caulks Field Rd, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

$20,000

23710 L Rd, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

$15,000

Fish Hatchery Rd, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

$76,000

23693 L Rd, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

$21,000

Spinnaker Rd, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

$799,900

6 Beds ⋅ 4 Baths

Welcome to the former historic HILLTOP HOTEL! A charming estate which underwent significant renovations in 2021 while preserving many of the original characteristics the home has to offer. This property is unlike any other - offering historic charm, tranquil atmosphere, ample privacy, outdoor living & entertaining as well as turnkey amenities. The property sits perched high above the hillside of the Eastern Shore providing for stunning sunsets as you relax on the wraparound porch feeling the gentle breeze from the Chesapeake Bay. As you enter and proceed up the gravel driveway you are greeted by a large circular drive, beautifully manicured lawn, 4.74 acres of mature landscaping and the grandeur of the 3 story historic home. The first and second floors have been updated to include bright new paint throughout, remodeled kitchen offering an abundance of natural light, all new appliances, french doors were installed off the kitchen and study leading out to a new beautiful brick terrace overlooking scenic countryside views, updated powered room on the first floor, primary second floor bath has been completely remodeled to include updated amenities. The second floor offers 3 bedrooms, 2 full baths along with a spacious laundry room. As you make your way up to the third floor you immediately noticed the extensive renovations. Every aspect of the third floor was meticulously remodeled and redesigned including new insulation, new plumbing, new electric, new drywall, new commercial grade HVAC system and all 14 windows throughout the third floor were replaced. The third floor offers 3 bedrooms, 1 full bath and large beautiful living area. All hardwood floors throughout the home were refinished to their original beauty. New commercial grade water treatment system was installed. The wraparound porch was completely painted and all porch columns were wrapped. The exterior back of the home was sealed and painted. New roof installed. Both chimneys were repointed. Dual zone HVAC. This is a COMMERCIALLY ZONED property - Zoned Crossroads Commercial. Perfect for B&B or commercial use. Centrally located between historic Chestertown, MD and Rock Hall, MD. Owners are open to selling property furnished with the exception of several items.

7979 Sandy Bottom Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$179,900

MECHANICS, GREEN THUMBS, CHEFS, NATURALISTS, AND FOOD TRUCKS are just a few of the entrepreneurs that should drop everything and call on this great offer: 1.52 acre corner location with ample parking, free standing 1750 sq ft bldg, excellent visibility and high daily traffic count.

8000 Rock Hall Rd, Chestertown

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: (410) 814-2400

$1,725,000

4 Beds ⋅ 5 Baths

SMITH-RINGGOLD HOUSE. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort. Originally a merchant’s home in the heart of historic Chestertown, the Smith-Ringgold house has been modified representing four defined periods and enlarged over the course of its 250-year history. The present owner took two years to restore the home’s structural integrity from the foundation to the attic, adding a river-side addition and porch, replacing the cedar shingle roof, and completely redoing the plumbing, wiring, heat and A/C systems. The wood floors throughout the house have been beautifully restored. Modern storm windows are energy efficient and all but eliminate street noise. Aside from your own personal touches, this house is move-in-ready. The ground floor has a large double parlor, cozy sitting room, formal dining room, breakfast room, and a stunning chef’s kitchen. An important feature is the hand painted dining room mural by noted artist Jack Schroeder. The front hall, redesigned in about 1860, replaced a steep stairway with a grand and gracefully curving staircase. The second floor contains three large en-suite bedrooms and a laundry room that is also accessible from the kitchen via a “secret” staff stairway. The third floor has a large sitting room, bathroom, and bedroom, with part of the home’s original c. 1759 roof forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River. The free-standing brick garage dates from the early 20th century, when car garages replaced horse barns. This structure could easily be repurposed as an artist’s studio or home workshop. A wide driveway area provides additional off-street parking. Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture. CHESTERTOWN IN THE COUNTY OF KENT Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities. Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian “painted ladies.” With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers. The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleries—but no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today Chestertown is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders.

201 N Water St, Chestertown

Listing courtesy of Maryland Heritage Properties. Contact: (443) 480-7342

$725,000

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-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, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. 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 #37, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$3,000,000

87-acre tract located Northwest of Chestertown. Land tract was annexed into the town of Chestertown and is served with municipal services. The property is zoned residential (R-3 and R-4) and has been previously studied for residential development. The land is approximately 44 acres of tillable and 48 acres of timber. The farmland is surrounded by a forested buffer and may nicely serve the future layout and privacy of a residential community. Site plans and previous preliminary designs are available to review to guide future planning on the property and can be provided.

Flatland Road, Chestertown

Listing courtesy of The Land Group. Contact: (410) 934-3478

$1,499,000

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! The Schooner model is an exquisite three-bedroom, three-and-a-half-bath home that 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

$949,900

4 Beds ⋅ 4 Baths

Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. The Sultana model is an exquisite four-bedroom, two-and-a-half-bath home that 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

$413,500

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:

$625,000

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:

$805,000

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

$815,000

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

$575,000

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:

$50,000

Buildable parcel with the possibility of subdividing into 2 lots.

9048 Georgetown Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 643-3033

$40,000

PERC Approved Lot in Chesapeake Landing! Community offers voluntary association for an annual fee of $40. Dues would provide access to Mill Creek Pier and Worton Wharf Boat Ramp. Boat Slips available via application and at additional costs. More details at chesapeakelanding.org. Plus easy access to Worton Creek Marina! Plenty of options to put the boat, kayak, paddleboard or canoe in the water. It's time to build your new property!

Lot 72 & 73 Buck Neck Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact: (443) 274-1900

$75,000

Two-acre wooded lot with road frontage on Caulks Field Road, Kent Co., MD. Zoned AZD,Village District; land use: Residential. Planned public water/sewer service area. No public water/sewer allocation at this time.

Caulks Field Road, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$60,000

Two-acre wooded lot located SE Georgetown Road, West of Chestertown. Zoned Village District. Planned water/sewer service area. No public water/sewer allocation at this time.

Georgetown Rd Se, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$799,000

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:

$24,000

Lot 142 & 142 - .34 +/- acre lot in Chesapeake Landing. Perc Approved, See documents for perc information. We suggest seeing Kent County Environmental Health for perc verification and further information. Perfect place to build your home or spec house! Located near public boat ramp and marina.

Lot 142 & 143 Clarissa Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

$950,000

Don’t miss out on the opportunity to own this restaurant and bar located in Historic Downtown Chestertown. 98 Cannon offers both indoor and outdoor dining with panoramic views of the Chester River. Ideally located next to the Chestertown Marina so patrons can dock and dine. Ample parking---13 owned spots, 26 shared spots, plus on-street parking. Chestertown’s only restaurant on the River. Unlimited potential for year-round income. Chestertown is located 90 minutes from Baltimore, DC, and Philadelphia and less than 1 hour from Annapolis. Enterprise Zone tax credits available. Buyers requesting additional information must sign NDA. Property is being sold as-is.

98 Cannon St, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 643-3033

$157,000

2 Beds ⋅ 1 Baths

Wonderful turn key living in Chestertown. Whether it is year round or long weekends, Tolchester Village makes it easy to enjoy all the area has to offer. There are plenty of fishing and boating options nearby or take a 25 min ride over to visit Eastern Neck Island to enjoy multiple viewing, hiking and water activities. So close to Rock Hall and several Marina's with Tolchester Marina just 1.8 miles away. Maybe a day in town suits you perusing the quaint shops and or dining at one of numerous options. Then there is always the possibility of relaxing on your very own patio which backs up to protected forest land. Once home, you have a fully renovated 2 bed 1 bath on two levels. Your main level includes an entry hall with two closets, an L shaped kitchen with washer/dryer, dining area extending to living with utility closet with ample extra storage all leading to patio with grilling area and large outdoor shed closet . The upper level boasts two well sized bedrooms, large hall closet, linen closet and full bathroom with a tub/ shower. Let this be your village!!!

21341 Persimmon Dr Unit #17, Chestertown

Listing courtesy of Coldwell Banker Realty. Contact: (703) 471-7220

$42,000

Chesapeake Landing .82 acre wooded building lot with County approved perc site - priced to sell. Community pier and ramp, close to Worton and Chestertown.

Clarissa Road Parcel 161, Chestertown

Listing courtesy of The Hogans Agency Inc.. Contact: (410) 778-1665

$37,000

2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information.

Melitota Ln, Chestertown

Listing courtesy of The Hogans Agency Inc.. Contact: (410) 778-1665

$4,000

Opportunity to own property at Chesapeake Landing. Chesapeake Landing has a voluntary HOA which gives you access to the boat ramp and the Chesapeake Bay and Worton Marina. The marina and boat slip are extra. KC Health Department says the site failed perc test in 1998-9 but check with them about further possibilities.

Lots 233 & 234 Clarissa, Chestertown

Listing courtesy of The Hogans Agency Inc.. Contact: (410) 778-1665

$41,500

New price! 3 wooded lots; 1 building site on Elm Rd as you enter Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by. These lots have a sewer allocation so they are ready for your house. Just over 1/3rd of an acre all together.

Elm Rd, Chestertown

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

$15,000

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.

Sheldrake Dr, Chestertown

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

$995,000

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:

$950,000

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:

$995,000