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Chestertown MD Real Estate & Homes for Sale

82 Properties Found

The median home value in Chestertown, MD is $257,000. 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 $257,000. 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 82 properties displayed
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Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,393
Status:
NEW LISTING
MLS#:
MDKE116906
Type:
Other
Subdivision:
Chester River Landing
Lot size:
0.07 Acres
Year built:
2015
Courtesy: RE/MAX Executive
View additional info

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 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.

Beds:
5
Baths:
3 Full
Sq.Ft.:
2,376
Status:
NEW LISTING
MLS#:
MDKE116904
Type:
Single Family, Single Family-Detached
Subdivision:
Crestview
Lot size:
0.69 Acres
Year built:
1990
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Welcome to Crestview! Located right outside of town and just minutes to Downtown Chestertown! This 5 bed, 3 bath home is nicely situated on a corner lot w/ mature landscaping & at the beginning of a Cul-De-Sac! Granite counter tops, gas fireplace and 2 master bedrooms (one on the 1st floor) are just some of the amazing things this home has to offer. Solar panels are about 5 years into the lease and save the homeowner a bundle in electric! A home inspection was completed and seller is willing to share after an offer is made, saving the buyer costs in inspections!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,690
Status:
NEW LISTING
MLS#:
MDQA144792
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.45 Acres
Year built:
2001
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Lovely 3 bedroom, 2 bath Cape Cod in Chester Harbor. Situated on a large, very private lot with mature trees and super charming, expansive back yard. Nestled in near Rosin Creek this home is a walk to the community beach, convenient to Historic Chestertown, as well as, easy commute to metropolitan hubs. Perfect work from home spot! The home features, upgraded appliances, built in cabinets, hard wood flooring, spacious garage, main level bedroom and more!

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
975
Status:
NEW LISTING
MLS#:
MDKE116792
Type:
Townhouse
Subdivision:
Vicker's Row
Lot size:
0.01 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
View additional info

Pristine end unit townhouse located in Vicker's Row with fresh paint throughout! Two bedrooms, 1 1/2 baths, gorgeous hardwood floors throughout. Private rear deck with extra storage and off street parking! Newer roof & HVAC system! Enjoy minimal maintenance living within walking distance to the farmer's market, downtown shopping, restaurants, galleries, the Chester River and Washington College.

Beds:
4
Baths:
6 Full
Sq.Ft.:
3,237
Status:
NEW LISTING
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
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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. Currently run as a bed and breakfast. Additional buildable lot at the rear of the property included in the sale. Driveway with 6-8 parking spaces makes hosting guests easy.

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,470
Status:
NEW LISTING
MLS#:
MDKE116826
Type:
Single Family, Single Family-Detached
Subdivision:
Langford Bay Estates
Lot size:
1.15 Acres
Year built:
1980
Courtesy: Cross Street Realtors LLC
View additional info

Water view and water access home in Langford Bay Estates has something for everyone! Main-level living, a 2-car attached garage with workshop, mature landscaping, beautiful Four Season room off the back, and large living room with gas fireplace. Improvements include an additional bedroom or office off the garage, a new (2018) 20 SEER heat pump and whole house propane generator. The boat slip at the community pier is only $500 a year!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,976
Status:
NEW LISTING
MLS#:
MDKE116888
Type:
Townhouse
Subdivision:
Oakstreet
Lot size:
0.08 Acres
Year built:
2003
Courtesy: Benson & Mangold, LLC
View additional info
Beds:
3
Baths:
2 Full
Sq.Ft.:
1,979
Status:
NEW LISTING
MLS#:
MDKE116858
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.57 Acres
Year built:
2000
Courtesy: Benson & Mangold, LLC
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Beautifully landscaped corner lot in Coventry Farms with house featuring the finest in one story living. Brazilian cherry flooring throughout compliments the decor. Master bath has handicapped accessible tiled walk-in shower, heated tile floors , granite counter tops, and walk-in closets. Large master bedroom suite opens onto back Trex built porch with awning so you can enjoy your morning coffee. Kitchen boasts Bosch appliances with granite counter tops and attached breakfast nook. Soft close kitchen cabinets with full extension pull out drawers.Gas convection oven range with warming drawer. Recessed lighting in kitchen and living room. Screened in porch off the breakfast nook allows for easy access for outdoor dining options. Open floor plan with kitchen overlooking living area and also a separate dining area. Oversized two car garage attached to the house with built-in cabinets. Detached additional two car garage to store your boat and ample room for your workshop. Detached garage features separate entrance, three zone heat, it's own electrical subpanel and separate entrance off Devon Dr.. Outdoor patio has hot tub with pergola. Landscaped lot has 11 zone irrigation system. Roof is one year old and and a/c-heat pump and furnace was replaced two years ago.This house is meticulously maintained and show extremely well.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,160
Status:
NEW LISTING
MLS#:
MDKE116860
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.18 Acres
Year built:
1969
Courtesy: Rock Hall Properties Real Estate
View additional info

Very unique home in Tolchester Estates with breath taking views of the Chesapeake Bay. This home has ceramic tile floors, lots of stone and tile work throughout. Stainless Steel appliances and whirl pool tub in the Master bedroom. Like I said, very unique and beautiful. Definitely a "Must See".

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,834
Status:
NEW LISTING
MLS#:
MDKE116856
Type:
Single Family, Single Family-Detached
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1965
Courtesy: Cross Street Realtors, LLC
View additional info

Gorgeous Split Foyer in the Byford Development, that is close to EVERYTHING! This property boasts 4 Bedrooms and 2 full baths , plus a bonus room! Closets in every bedroom! Beautifully updated from the kitchen to the lower level. Private back yard and room for fun! Did I mention the hardwood floors throughout the first level? There is a pellet stove on the lower level that will keep you warm and toasty, while not breaking the bank on heating costs. THIS IS A MUST SEE, WON'T LAST LONG!

Beds:
4
Baths:
4 Full
Sq.Ft.:
2,737
Status:
NEW LISTING
MLS#:
MDKE116838
Type:
Single Family, Single Family-Detached
Subdivision:
Chesmar
Lot size:
0.75 Acres
Year built:
1964
Courtesy: Gunther-McClary Real Estate
View additional info

This wonderful 4 bedroom family home has plenty indoor and outdoor space for everyone. The addition of entire second floor and garage along with first floor renovations were completed in 2008. Separate suite upstairs provides privacy from rest of the family. Only minutes from Chestertown by boat or car. The community of Chesmar, located on the north side of the river provides great boating along the Chester River. The double lot gives additional privacy and space on either side. The screened-in porch houses a hot tub to relax in at night without being bothered by bugs and the balcony off the family room on the second floor offers a beautiful view of the stars and moon over the river. Lots of storage inside and out for all the toys, kayaks and water gear. Walk out to the pier, board the boat and be on the river instantly for fishing , waterskiing or to enjoy abundance of wildlife on a sunset cruise.

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,428
Status:
NEW LISTING
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
Beds:
6
Baths:
3 Full/1 Half
Sq.Ft.:
4,492
Status:
NEW LISTING
MLS#:
MDQA144706
Type:
Single Family, Single Family-Detached
Subdivision:
Flyway
Lot size:
1 Acres
Year built:
1999
Courtesy: Taylor Properties
View additional info

Sheeew where to start! This beautiful 6 Bed 3.5 Bath home boast nearly 4500sqft. Has a laundry list of custom features through out including Oak wood floors, wainscoting, chair railing, crown molding, custom wooden blinds and Smart blinds to name a few. Totally updated kitchen with all new stainless steel appliances, granite counters and a large eat at island. Formal dining area just off the kitchen. Large 1st floor master bedroom/bath. A deep soaking tube and walk in shower Sitting library room with built in book shelves. A large family room with a brick center piece gas fire place for entertaining. Bright sun room with sky lights over looking the large rear porch that's half covered and half open for sun shine. Heated Salt water pool offering great sun during the day and shade in the evening hours provided by mature trees. Fully fenced in rear yard for animals and privacy with large vehicle access gates. Handicap rear access ramp on the rear deck. This house comes with a full Intercom system and an ADT video security system. On demand gas Instant hot water heater for endless hot showers. Smart thermostats to keep tabs homes interior temps. Oversized side entry 2 car garage as well as a 28x43 3 Car detached garage that is insulated. There is a detailed list of all custom features/upgrades with dates upon request. Recent home appraisal at $575,000

Beds:
3
Baths:
3 Full
Sq.Ft.:
2,896
Status:
NEW LISTING
MLS#:
MDKE116790
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
89.23 Acres
Year built:
1965
Courtesy: Cross Street Realtors LLC
View additional info

"Gliding Gander Farm" Spectacular Chesapeake Bay waterfront farm with over 1/2 mile of protected shoreline with sandy beaches. Sunrises over the ponds & Sunsets over the bay. Rockfish out your front door and ducks and geese out your back door. 117.57 acres includes two (2) 10+ acres perced waterfront lots & one (1) Bay view lot. 100 acres of highly productive Mattapex soils with 3 ponds including well service. 2900 SF residence with 3 bedrooms & 3 full bathrooms with views to the Chesapeake from every room. 40 X 80 heated metal workshop for all your toys and more. We are following the COVID-19 guidelines issued by MAR.

Beds:
3
Baths:
3 Full
Sq.Ft.:
2,896
Status:
NEW LISTING
MLS#:
MDKE116788
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
89.23 Acres
Year built:
1965
Courtesy: Cross Street Realtors LLC
View additional info

"Gliding Gander Farm" Spectacular Chesapeake Bay waterfront farm with over 1/2 mile of protected shoreline with sandy beaches. Sunrises over the ponds & Sunsets over the bay. Rockfish out your front door and ducks and geese out your back door. 117.57 acres includes two (2) 10+ acres perced waterfront lots & one (1) Bay view lot. 100 acres of highly productive Mattapex soils with 3 ponds including well service. 2900 SF residence with 3 bedrooms & 3 full bathrooms with views to the Chesapeake from every room. 40 X 80 heated metal workshop for all your toys and more. We are following the COVID-19 guildlines issued by MAR.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
4,874
Status:
Active
MLS#:
MDKE116814
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.26 Acres
Year built:
2009
Courtesy: CR Realty
View additional info

This BEAUTIFUL Brick front 4 bedroom 2.5 bath home boosting 4,874 SQFT +/- of living space can be yours at an AMAZING PRICE! This home is located in a well-cared for and quiet neighborhood located in Chestertown on a corner lot backing to open space for more privacy. Inside you start off by walking into a great open floor layout with a formal dining room, living room, large open kitchen with Island overlooking the sun-room and living room. Kitchen has lots of cabinet space, granite counter-tops and stainless appliances. The sun-room has a doorway off the back of house that will lead you to the large recently installed 2nd story deck that~s perfect for grilling and entertaining. As you make your way upstairs, you will find the huge master bedroom with tray ceilings, walk in closet, a large sitting-room, his and her sink, and a shower/tub! Also there are three bedrooms and a full bathroom. The full Basement is just about fully finished and has a walk out level to the back yard. Two car garage and a black top driveway. Call today before this one is SOLD!

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.:
1,080
Status:
Active
MLS#:
MDKE116806
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.1 Acres
Year built:
1970
Courtesy: Taylor Properties
View additional info

Lovely renovated house near downtown Chestertown! Do not miss your chance to own this cute 3 bed 1 bath house that is walking distance from HH Garnet Elementary School, public library, post office, churches, and more! Don't miss your chance and act fast!! Submit offers to listing agent.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,474
Status:
Active
MLS#:
MDKE116796
Type:
Single Family, Single Family-Detached
Subdivision:
Orchard Hill
Lot size:
2.83 Acres
Year built:
1989
Courtesy: Davis Real Estate, Inc.
View additional info

Nice 4 bedroom ranch home on 2.8 acres in Orchard Hill. One mile from Chestertown. Family room with wood burning fireplace, separate dining and living rooms, large enclosed rear porch and attached two car garage.

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:
2
Baths:
1 Full
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE116786
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester
Lot size:
0.69 Acres
Year built:
1954
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Looking for a country get-away? This could be it! Located in the water privilege community of Tolchester, this 2 bedroom, 1 bath home sits on about 3/4 of an acre. There is a screened in front porch and back deck with an outdoor shower. The downstairs has an open floor plan with kitchen and living area with a wood stove. Aside from the two bedrooms and bathroom on the second floor there is also a living/family room all with wood floors. It is in need of some updating, but it's ready to make your own. The detached one car garage and shed for your boat are located on the side yard. Tolchester's HOA is not mandatory, but very reasonable to join. The Tolchester Marina and the Shanty Beach Bar are less than a mile away so you can walk or ride your bike to one of the counties most popular destination. Easy to show so come take a look!

Beds:
4
Baths:
3 Full
Sq.Ft.:
3,069
Status:
Active
MLS#:
MDKE116762
Type:
Single Family, Single Family-Detached
Subdivision:
Byford Court
Lot size:
1.65 Acres
Year built:
1970
Courtesy: Keller Williams Select Realtors
View additional info

Coveted private waterfront home!! Walk into Chestertown, yet have all of the privacy as if you were miles away. Chestertown, founded in 1706, is a quaint town filled with arts, entertainment, fine restaurants, shops, old inns and home to one of the best farmer's market in MD. You can walk to the parades, Chestertown Tea Party Festival and summer concerts along the brick paved walkways and enjoy the water views and boats coming in. This home sits at the end of a culdesac on a very quiet street. Watch the sunrise and the moon reflect on the water. This home was dubbed "moon river" retreat . Over 1.6 acres and just shy of 3,000 sq ft. This rancher is waiting for an update . Wooden floors and huge glass doors looking over the river will make you fall in love. A built in pool and a yard to hold family gatherings, weddings, and a place to make incredible memories awaits you. . Check out the approx. floor plan here https://youriguide.com/8_byford_ct_chestertown_md/doc/floorplan_imperial.pdf

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
2,244
Status:
Active
MLS#:
MDKE116742
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.1 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Victorian style house located the historic district of Colonial Chestertown. Random width flooring. Details like crown molding and chair railing, high ceilings and slate fireplaces. Lovely patio. Detached garage and driveway. New roof in 2019. 1 1/2 blocks to Chester River.

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.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,512
Status:
Active
MLS#:
MDKE116716
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.34 Acres
Courtesy: D N K Real Estate, LLC
View additional info

BRAND NEW CONSTRUCTION 3 BR Cape Cod in quiet, waterfront community of Chesapeake Landing located just off Worton Creek in beautiful, historic Chestertown. A short drive to the restaurants and shops of Rock Hall on the Chesapeake Bay. Excellent area schools, parks and community center. 1st level Master BR with full bath. Upstairs, 2 BR and full bath. Large, eat in kitchen. Living Room. Separate front room for dining, office or family room needs. Back patio is perfect for entertaining. Community is water access with 2 marinas, boat slips and docks. A perfect location to keep your boat for a weekend away on the beautiful Eastern Shore or to make this your permanent home.

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