Roger Boyce
443-496-2007

Chestertown MD Real Estate & Homes for Sale

46 Properties Found

The median home value in Chestertown, MD is $279,000. This is higher than the county median home value of $192,000. The national median home value is $231,815. The average price of homes sold in Chestertown, MD is $279,000. Approximately 43% of Chestertown homes are owned, compared to 42% rented, while 15% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


1–25 of 46 properties displayed
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Beds:
4
Baths:
2 Full
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
MDQA146072
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.52 Acres
Courtesy: Long & Foster Real Estate, Inc.
View additional info
Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
NEW LISTING
MLS#:
MDKE117406
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

Take a look at this beautiful townhome located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a terrific galley kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. The three bedroom units are priced at $129,900 and the two bedroom units are priced at $119,900. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40.00 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,160
Status:
Active
MLS#:
MDQA145942
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.37 Acres
Year built:
2004
Courtesy: EXIT On The Bay
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Driving up to this home one quickly is drawn to the eye-catching curb appeal that you don't often find in this price range. Enjoy comfy, cozy one level living. The attached one-car garage could be converted into more finished living space. Features include hardwood floors throughout, a large deck off the back of the home that would be perfect for cookouts, and a spacious level private backyard. Flat-screen television mount in living room stays, as does Direct TV antenna on the roof(buyer will need to subscribe to service to use this service.) There is a swing set/slide in the back yard that is not included, however, the tenant who is moving out would sell for $500 (or remove prior to closing.) The community has voluntary HOA fees, and community amenities.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE117342
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Estates
Lot size:
0.34 Acres
Year built:
2018
Courtesy: Douglas Realty, LLC
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Wonderful starter or retirement home! Maintenance-free living at its best. Great open floor plan. Private master suite separated from the other 2 bedrooms by the family room. Home shows like new, with all appliances so this is a complete package. Fenced back yard has semi-permanent vinyl clad fence...leave as is or easily remove. Nice storage shed for your lawnmower and tools. The property line goes behind the trees. Enjoy sweltering summer days in your easy to maintain above-ground pool. The owners have taken wonderful care of this home. There is a very friendly dog, Maddie, and an equally friendly cat, Nieko--please do not let them out of the home. Come see this home quickly, as it will not stay on the market long. Flexible possession is easy...so if you need to be in quick, we can make this happen!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,288
Status:
Active
MLS#:
MDQA145776
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1988
Courtesy: Doug Ashley Realtors, LLC
View additional info

Cute as a button, three bedroom 2 bath cottage with an open living area. Back yard is adorable, extremely private, with a deck, and plenty of room for kids of all ages, and their furry friends. Come see this terrific home in Chester Harbor. You can join the association for a normal fee and enjoy water access. There is a park and picnic area, and Rosin Creek for some water front. You can access the Chester River as well!

Beds:
1
Baths:
1 Full/1 Half
Sq.Ft.:
936
Status:
Active
MLS#:
MDKE117300
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.04 Acres
Year built:
1900
Courtesy: Select Land & Homes, LLC
View additional info

This charming Downtown Chestertown home offers a semi open floor plan and cozy feel with hardwood floors throughout! The first floor features a dining and living area, powder room and kitchen with side door that leads to landscaped backyard. Upstairs is a full bathroom with laundry, bedroom and sitting room (or second bedroom) with built in shelves and exposed brick chimney. The courtyard garden with brick walkway lead to Downtown, waterfront, shops and restaurants. Bike trails and park for your enjoyment are nearby. The delightful home makes for easy living! More Photos Coming Soon.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
Active
MLS#:
MDKE117236
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

Take a look at this beautiful townhome located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a terrific galley kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. The three bedroom units are priced at $129,900 and the two bedroom units are priced at $119,900. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40.00 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,360
Status:
Active
MLS#:
MDQA145652
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1988
Courtesy: Keller Williams Select Realtors
View additional info

Quiet, one level living on a spacious .34 acre property in Chester Harbor with community water access, beach & picnic area with dock. This well maintained 3 bedroom, 2 full bath, low maintenance home is on a level lot with huge fenced back yard for a garden, play area for the kids and plenty of room for the dog. All electric utilities, added addition has large laundry area w full bath, pantry & plenty of additional space, space. A 2016 remodel replaced the septic, roof, vinyl siding, kitchen and many other up grades making this a great home to raise a young family or would be perfect for retirement. Just a hop across the Chester River Bridge to downtown Chestertown, Farmers Market, Washington College, hospital, restaurants, music & shopping, etc. Come and take a look at this very affordably priced gem and make it yours.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,316
Status:
Active
MLS#:
MDQA145556
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1969
Courtesy: RE/MAX Executive
View additional info

OPEN HOUSE - SUN. Nov. 22nd - 2pm to 4pm - *HURRY! Completely updated and gorgeous!! This 4BR, 2 bath one-level living is in move-in, excellent condition. Granite countertops, island, table space, opened floorplan, beautiful baths, huge yard and fenced just waiting for your furry friend. This will not last, so make your appointment now to be the first to view this lovely home in a great water priv. Community!!

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
6,050
Status:
Active
MLS#:
MDKE117208
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
26 Acres
Year built:
1966
Courtesy: TTR Sotheby's International Realty
View additional info

Presenting "Honest Point Farm" - Embrace the finest of Eastern Shore Living, Serenity and Nature at Honest Point Farm. Three Waterfront homes in Chestertown's Estate area all situated on 26 acres. This rare property consists of a beautifully maintained and updated main estate residence with breathtaking views and two charming guest homes- Winter Cottage and Summer Cottage. The main residence boasts 5 bedrooms (4 en-suite) a recently added expansive gourmet kitchen, renovated bathrooms, refinished hardwood floors, generator, 3 new heat pumps and a recently refinished waterside gunite pool. The guest homes each boast 2 bedrooms and one bath, perfect for company or as rentals. Ideally located, each dwelling has its own privacy and gorgeous views. Grounds also include an orchard, garden, wooded area, dock, in ground pool, barn, pond, various outbuildings with approximately 20 acres of woods. Given the acreage and all the fabulous amenities, this property is an exceptional offering! **Property Video in Virtual Tours**

Beds:
6
Baths:
3 Full/1 Half
Sq.Ft.:
4,048
Status:
Active
MLS#:
MDKE117086
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.15 Acres
Year built:
1910
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

A real restoration opportunity on Water St. This Victorian is a project for someone who has a love of old houses.It needs attention. This house has a Mansard roof is covered in pressed tin. Hardwood floors throughout and high ceilings. Crown moldings, chair- railings built-ins and fireplaces. There is a total of 5 bedrooms and 3.5 baths. Wide covered porch in the front. Screened porch in the rear. 2 car garage and driveway for off street parking. Heat is not functioning, needs a new roof(part is covered with a tarp). Partial central air. Some views of the river over the 18th century houses from the second and third floors. This house has great potential and is a rare find for Water St. It is waiting to be restored to its former glory. Property is being sold in as-is condition; some restoration plans available.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,064
Status:
Active
MLS#:
MDKE117128
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.06 Acres
Year built:
1920
Courtesy: RE/MAX Executive
View additional info

Solid investment property. Property is currently leased for a year through 5/15/2021. Rental market is strong because of close proximity to College and downtown. Fenced in rear yard allows privacy and shed has ample storage for yard accessories. If your are looking to add to your investment portfolio, take a look as this has positive cash flow. 24 hours showing notice required because house is tenant occupied. Lister must accompany. There is no sign on property.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,269
Status:
Active
MLS#:
MDKE117004
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

Take a look at this beautiful model home located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a terrific galley kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. The three bedroom units are priced at $129,900 and the two bedroom units are priced at $119,900. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40.00 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
3
Baths:
2 Full/2 Half
Sq.Ft.:
3,248
Status:
Active
MLS#:
MDKE116774
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
35.76 Acres
Year built:
1856
Courtesy: Cross Street Realtors LLC
View additional info

Middle Plantation Circa 1856, better known as Running Fox Farm, is one of the finest hunting farms in Kent County, Maryland - abundant deer, Canada and Snow geese, dove and turkey. The residence has been meticulously renovated, an extensive, well-documented project that includes upgrades such as 400 amp electric service and wiring, updated plumbing, custom restorations true to the period, and more. 213 acres with 166.6 prime soils, 60.5acres in CRP... all on FIVE 30+ acre subdivided, perc-approved lots.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,393
Status:
Active
MLS#:
MDKE116906
Type:
Other
Subdivision:
Chester River Landing
Lot size:
0.07 Acres
Year built:
2015
Courtesy: RE/MAX Executive
View additional info

JUST REDUCED! Welcome to 114 Landing Lane in the Chester River Landing community located on the Chester River in historic Chestertown Maryland. This beautiful 3 Bedroom, 2.5 Bath, home is 2300 sq. ft (tax record is incorrect) and is awaiting it's next owner. Feel the pride of ownership in this home from the hardwood flooring, to the upgraded gourmet kitchen. The large great room featuring a gas fueled fireplace and large windows to allow in the natural light, situated just off the kitchen is a wonderful area to relax, read or just gather with family and friends. The second level of the home features an area that can be utilized as a den or large office. Proceed another half level upstairs to an expansive family room with dining area, 2 additional bedrooms and another full bath. There are two large rear decks on this home, one off the kitchen on the main level and a second off the family room on the second level. Enjoy the views of the Chester River from the 2nd level deck. Be advised that the tax record is showing an incorrect square footage on the home, the actual square footage is over 2300 sq. ft.

Beds:
5
Baths:
6 Full
Sq.Ft.:
4,100
Status:
Active
MLS#:
MDKE116878
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.66 Acres
Year built:
1860
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Welcome to the historic John . Stam house, the only "A-rated" Victorian in Chestertown according to the Secretary of the Interior. This property has so much to offer. A Gothic Revival Victorian with painted fire places, a double parlor with pocket doors, and entrance hall. Features such as hand painted plastered ceilings, Jenny doors, and original medallions, make this a one of a kind home. Dado chair rail and paneling, Bradbury and Bradbury Art Wallpapers, Soapstone fireplaces, China closet, and the list goes on. The details are such that the property really needs to be seen to be appreciated. Kitchen is completely upgraded with Delohghi stove and sub zero refrigerator. Waterfall in the back yard with gracious gardens make for a charming outdoor oasis. "Carriage slate "architectural shingle roof. Currently run as a bed and breakfast. Additional buildable lot at the rear of the property included in the sale which makes the total property approximately 1.3 acres. . Driveway with 6-8 parking spaces makes hosting guests easy.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,976
Status:
Active
MLS#:
MDKE116888
Type:
Townhouse
Subdivision:
Oakstreet
Lot size:
0.08 Acres
Year built:
2003
Courtesy: Benson & Mangold, LLC
View additional info

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.

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,428
Status:
Active
MLS#:
MDKE116756
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.04 Acres
Year built:
1880
Courtesy: Cross Street Realtors LLC
View additional info

This downtown Chestertown house with good bones and rear yard, ready and waiting for a "this old house" renovation either as a residence or an apartment (perhaps two).

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,138
Status:
Active
MLS#:
MDKE116820
Type:
Single Family, Single Family-Detached
Subdivision:
Byford Court
Lot size:
0.86 Acres
Year built:
1969
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Views of the Chester River from this Byford Court property. One floor living. 2 wood burning fireplaces, hardwood floors. Much attention to detail. French doors, spectacular kitchen, skylights in all the best places, wonderful landscaping includes a mature fig tree. Just a short walk to the heart of Chestertown. Private back and rear yards. Long rear all weather porch.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,260
Status:
Active
MLS#:
MDQA144628
Type:
Manufactured/Mobile Home
Subdivision:
Ducks Neck
Lot size:
0.51 Acres
Year built:
1976
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Water privileged community in North Queen Anne's county on the Chester River! 1976 Mobile Home with additions. Tear down and use existing building pad. Functioning septic and well. Short distance ( 3 Lots) to private community beach/boat ramp on Chester River. Nice 1/2 acre lot with mature trees. Property backs to Duck Neck Campground. Probate/Estate sale. Prices below assessment. Zone X Flood Zone

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
1,562
Status:
Active
MLS#:
MDKE116682
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.11 Acres
Year built:
1900
Courtesy: The Hogans Agency
View additional info

Charming historic home featuring high ceilings, hardwood on every floor, covered front porch, formal dining or sitting room with pocket doors, detailed trim and so much more! Recently replaced hot water heater, electrical panel and HVAC systemic . This property is zoned Residential/Business (RB) and can be used as a single family home or as professional offices. Located one block from the Chester River waterfront. Seller Assistance considered. 1 parking space behind rear porch and numerous street spaces directly in front of the home. Can be shown between 10-4 and will need 48 hours notice to show.

Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
11,840
Status:
Active
MLS#:
MDKE116698
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
306.12 Acres
Year built:
1990
Courtesy: TTR Sotheby's International Realty
View additional info

"Walnut Point Farm" ~ Exquisite 300+ Acre Waterfront Farm with over a mile of Shoreline is the perfect Eastern Shore Retreat! The Estate offers a 7,500+/- Main House with indoor and outdoor pools, Pier with Grand Boathouse and lift with 7ft+/- MLW, Large 3 bedroom Historic Guest House, Waterfront Caretakers Home, Large Barn for all farming equipment, Covered Bridge with many other outbuildings and blinds plus a few waterfowl ponds. This Estate is perfect for those looking for and escape from the hustle and bustle of the metropolitan lifestyle that would like to take in all that nature offers with a plethora of high end amenities. Please See Truplace Interactive Tour For more Photos and Floorplan at https://mls.TruPlace.com/property/406/84311/

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,258
Status:
Temporarily Off Market
MLS#:
MDQA144146
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.35 Acres
Year built:
2006
Courtesy: RE/MAX Executive
View additional info

3D Tour: https://unbranded.youriguide.com/165_char_nor_manor_blvd_chestertown_md Welcome to 165 Char Nor Manor Blvd on the QA County side of Chestertown!!! Looking for water views that are basically water front??? This is the ONE!!! Unobstructed Chester River views without the waterfront price tag!!! Enjoy the peace and serenity that this property has to offer. This is a one of a kind property. Situated at the end of the waterfront street, this home is boasting over 2200 sq ft with an attached 2 car garage. No neighbors to your right and nothing behind you but water!!! When you enter this home you will notice that the entire home has been freshly painted, brand new carpet installed, new tile floor installed, and is ready for you to call it home! Entering the foyer you have a nice tile floor that leads to GORGEOUS hardwood floors through out the main level of the home. The Family Room is to the left and is open to the kitchen, giving this home an open, airy feel. The family room is large with an abundance of windows bringing in all the natural light and nature this property offers and it boasts a wood burning fireplace! From the family room you have 2 wide open entrances into the MASSIVE kitchen. The kitchen is gorgeous and offers water views that no other home has to offer!!! The kitchen offers you a large island with bar seating and pendant lighting, and abundance of countertop space and cabinet space, gorgeous hardwood floors, stainless steel appliances, an eat in table area, and the VIEWS are amazing!!! New tiles have also been installed in front of the sliding glass door leading to the deck. Finishing off the main level is the updated half bathroom, massive laundry room, which has plenty of room for storage also, and the entrance to the 2 car garage!!! Moving upstairs you will find 4 freshly painted LARGE bedrooms with great closet space. and brand new carpet throughout the entire second level. There is a bonus room off of the 4th bedroom that could be a possible 5th bedroom, playroom, office, etc. Endless possibilities with the bonus room!! Moving down the hallway you will find an updated, large full bathroom for the bedrooms boasting tile floors, fresh paint, and updated fixtures. Moving into the Master Suite!! AHHH peace and relaxation in this room!! Large bedroom with vaulted ceilings, fresh paint, new carpet, and it's own balcony so you can soak up those water views EVERY SINGLE MORNING!!! Wake up to the sounds of nature and water!!! Moving into the master bathroom you will find upgraded tile floors, upgraded fixtures, a HUGE Master Closet, a separate shower and 2 windows bringing in all the natural sunlight with water views. This master suite is one of a kind!!! You won't see these views anywhere else!!! Moving outback, you will find a freshly painted deck all overlooking the backyard, water, and nature. These views, this setting, you can't and won't find anywhere else!!! Privacy and water for a fraction of the price!!! The home is a convenient location to all major routes, only minutes to Downtown Chestertown, minutes to Centreville, short easy commute to Middletown, Dover, Annapolis, DC, the Beaches. AND you get the all the benefits from QA County and the QA County Schools!!! Put this home on your list today so you don't miss out on an almost waterfront property without the price tag!!!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,198
Status:
Active
MLS#:
MDKE116670
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.13 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Lovely Victorian with many original details. Beautiful wood floors, fireplace, updated kitchen and baths, new carpet in master bedroom and fresh paint throughout. Third floor bedroom could be home office. The porches and patio provide nice outdoor living space.Located in Chestertown's Historic District it is within walking distance to Washington College, shopping, restaurants and the Chester River.

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,000
Status:
Active
MLS#:
MDKE116496
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester
Lot size:
1.37 Acres
Courtesy: Cross Street Realtors LLC
View additional info

TO BE BUILT - List price reflects the lot & lot development with the Haydn model. There are many other floor plans and upgrades available with Caruso Homes, however there is no builder tie-in. All on two parcels totaling approximately 1.81 Acres on a quiet street among well-kept homes and manicured lawns. The second parcel is located on Elm St which allows access from the front or back of the property. This property also includes a paid sewer allocation! Just steps from the Tolchester Marina & The Shanty and only a quick drive to Rock Hall or Chestertown.

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