fill
fill
fill
DEE DEE MCCRACKEN
fill

dmccracken@
cbmove.com
fill
fill
fill
fill
fill
fill
fill
Buyers Info
fill
Sellers Info
fill
Owning Your Home
fill
Investing Advice
fill
Mortgage Info
fill
Neighborhood Info
fill
School Info
fill
Mortgage Calculator
fill
fill
fill

Chestertown MD Real Estate & Homes for Sale

68 Properties Found

The median home value in Chestertown, MD is $282,500. 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 $282,500. 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 68 properties displayed
Refine Property Search
Page 1 | 2 | 3 of 3    Prev | Next
Beds:
2
Baths:
1 Full
Sq.Ft.:
948
Status:
NEW LISTING
MLS#:
MDKE117302
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.12 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Adorable one level bungalow in Downtown Chestertown that backs to the rails to trails allowing easy access to running, biking and overall walkable to all that Downtown has to offer. This home is rare in that it has a driveway in the front and has a back alley making the rear yard accessible for additional parking. Current conditions seem structurally sound for renovations and necessary corrections allowing you to make your mark and make this home exactly what you want it to be. Save costs on building a new home and fix this one!

Beds:
1
Baths:
1 Full/1 Half
Sq.Ft.:
936
Status:
NEW LISTING
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:
NEW LISTING
MLS#:
MDKE117236
Type:
Other
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.:
2,156
Status:
NEW LISTING
MLS#:
MDKE117262
Type:
Single Family, Single Family-Detached
Subdivision:
Foxley Manor
Lot size:
0.44 Acres
Year built:
1969
Courtesy: Rosendale Realty
View additional info

COMING SOON! Great 3 Bedroom/2 Bathroom home on .44 acres in Foxley Manor listed at $220,000! A wonderful place to call Home - with it's Country Kitchen, Cozy Family Room, Possible 4th Bedroom/Den/Office, plus an Extra Bonus Room off of the Sun Room - this house everything you need! Freshly painted interior and completely MOVE-IN READY! Don't wait - as this one will go QUICK!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,360
Status:
NEW LISTING
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:
NEW LISTING
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

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:
3
Baths:
2 Full
Sq.Ft.:
1,502
Status:
NEW LISTING
MLS#:
MDKE117210
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.29 Acres
Year built:
1973
Courtesy: Rosendale Realty
View additional info

WHAT AN OPPORTUNITY TO MOVE TO CHESTERTOWN. CUTE BRICK RANCHER CLOSE TO COLLEGE, HOSPITAL, AND ALL TOWN AMENITIES. HOME HAS LARGE LIVINGROOM, DINING ROOM AND BREAKFAST AREA, NICE BEDROOMS AND GREAT SUNROOM OUT BACK TO ENJOY COFFEE OR COCKTAILS. HOME NEEDS YOUR INDIVIDUAL TOUCHES BUT WILL BE A REAL CHARMER. RENTALS ARE ALMOST ALWAYS IN SHORT SUPPLY. COULD BE NICE INVESTMENT PROPERTY AS WELL. CARPORT AND SHED COMPLETE THE PICTURE OUTSIDE. DO NOT DELAY. THIS IS A BANK HANDLED ESTATE SALE SO IT WILL BE " AS IS" BUT THE PROPERTY APPEARS TO BE READY FOR ALL TYPES OF FINANCING. ALL PARTIES MUST SIGN A COVID RELEASE PRIOR TO VIEWING

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,184
Status:
NEW LISTING
MLS#:
MDKE117276
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.23 Acres
Year built:
2007
Courtesy: Select Land & Homes, LLC
View additional info

This 3 bedroom 2.1 bath home is in move in condition! The floors are recently improved with luxury vinyl on the main level and brand new carpet on the upper level. The updated kitchen flows to the family room with a wood burning fireplace. A covered deck off the eat in kitchen further extends the living space! Downstairs is a finished basement with laundry and storage area. Upstairs is a spacious master bedroom with a large walk in closet and master bathroom. With two other nice size bedrooms and another full bathroom, this is a great home for a family. Outside there is a fully fenced rear yard and attached two car garage. Call Select Land and Homes to schedule your tour today!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,528
Status:
NEW LISTING
MLS#:
MDKE117170
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.55 Acres
Year built:
1900
Courtesy: Gunther-McClary Real Estate
View additional info
Beds:
3
Baths:
2 Full/2 Half
Sq.Ft.:
2,437
Status:
NEW LISTING
MLS#:
MDKE117270
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Estates
Lot size:
0.46 Acres
Year built:
2008
Courtesy: Doug Ashley Realtors, LLC
View additional info

Custom built by current owner, this 2604 square foot home has the first floor owner's suite, a formal dining room, living room, open floor plan with the kitchen and family room. Well landscaped with three bedrooms, 2 full baths, and 2 half baths, a nice back yard with a patio. This home is about 5 minutes from Chestertown, and shows well. Plenty of storage with an attached one car garage, a storage shed and upstairs has an additional storage room over the garage. There is an office or a crafting room, your choice!

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
6,050
Status:
NEW LISTING
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:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,136
Status:
NEW LISTING
MLS#:
MDKE117256
Type:
Single Family
Subdivision:
Calvert Homes
Lot size:
0.05 Acres
Year built:
1992
Courtesy: Coldwell Banker Realty
View additional info

Beautifully renovated townhome in the heart of Chestertown. Walk to restaurants, shops and the waterfront. Home offers on street parking, a carport, fenced in backyard and covered front porch. New carpet upstairs and laminate flooring on the first floor. Home a large living room and set in kitchen.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,512
Status:
NEW LISTING
MLS#:
MDKE117254
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.48 Acres
Year built:
2020
Courtesy: D N K Real Estate, LLC
View additional info

BRAND NEW CONSTRUCTION complete and READY FOR MOVE IN. 3 BR Cape Cod. 1st level Master BR with full sized bathroom, dual vanities and granite countertops. Master BR has oversized walk in closet. Open floorplan with separate side entrance into mudroom / laundry room with ample space to store outdoor shoes and coats. Large, bright eat in kitchen with granite countertops and picturesque country view of tree lined backyard. Open Living Area with ceiling fan and separate front entrance. Upstairs, spacious 2 BR and full bathroom. Back patio is perfect for entertaining. Located 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. Community dock with easy water access to Chesapeake Bay. Community is water access with 2 marinas, boat slips and docks. A perfect location for a weekend away on the beautiful Eastern Shore or to make this your permanent home.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,789
Status:
NEW LISTING
MLS#:
MDKE117252
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.99 Acres
Year built:
1969
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Lovely well-maintained home with major updates: new furnace and air conditioning, new septic and new well 2018, roof is approx. 4 years old, hot water heater 3 years old and new water conditioner. The kitchen has been updated with oak cabinetry to include slide out shelves, pantry cabinet, cutting board, appliance garage and two decorative glass cabinets. Large deck on the rear has access from the master bedroom and large family room. Wood burning fireplace has been converted to gas logs. The home is located at the end of Club Road with no thru traffic. Home is located in a water-privileged community and is only walking distance to the community boat ramp and boat slips. HOUSE SALE INCLUDES THREE SEPARATELY DEEDED LOTS OFFERING A TOTAL LOT SIZE OF .996 ACRE PER PUBLIC RECORD.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,074
Status:
NEW LISTING
MLS#:
MDKE117224
Type:
Single Family
Subdivision:
Tolchester
Lot size:
0.14 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

Updated in 2020, and shows great. Living areas and bedrooms are carpeted, all major appliances, to include washer/dryer, microwave, stove, refrigerator. Kitchen is a galley style kitchen with washer and dryer under the countertop. A community playground and sport court, great location and very pretty area. Close to the Chesapeake Bay

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,087
Status:
Active
MLS#:
MDKE117194
Type:
Single Family
Subdivision:
Tolchester
Lot size:
0.14 Acres
Year built:
1958
Courtesy: Doug Ashley Realtors, LLC
View additional info

You can't beat the condition... the price or the location. Completely remodeled and shows so well. Two bedrooms, one bath, a beautiful living area, outside storage, a porch, patio with a privacy fence to separate the neighboring patio. Backs to trees and completely affordable. There is a basketball court, a playground for kids. You own the property, it's not a condo situation. Beautiful location. Come and see!

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,400
Status:
Active
MLS#:
MDQA145502
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.4 Acres
Year built:
2020
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Quiet and Peaceful. Your chance to get a new home for a great price! Being built, is a 4 bedroom 2 bath open floorplan rancher. Everything you need. Why settle for any house when you can create your memories here, brand new. This home is conveniently located to all the major routes, only minutes away from Downtown Chestertown and Centreville. A short easy commute to Middletown, Dover, Annapolis, DC, and the beaches. Located in QA County school District. Attached is the list of specifications for construction, with time to upgrade where you may think is necessary.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE117096
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Estates
Lot size:
0.33 Acres
Year built:
2020
Courtesy: Rosendale Realty
View additional info

CUTE RANCHER FEATURES SPLIT BEDROOM DESIGN WITH LARGE OPEN CENTRAL LIVING ROOM, DINING AREA, AND KITCHEN. WHITE CABINETS, STAINLESS APPLIANCES, VINYL LAMINATE FLOORS FOR EASY MAINTENANCE. ARCHITECTURAL SHINGLES PRIVATE WELL AND PUBLIC SEWER. HOME SHOULD APPEAL TO THOSE LOOKING FOR DURABILITY AND EASY MAINTENANCE. INTERIOR PICTURES ARE OF A PREVIOUSLY BUILT MODEL AND FEATURES ARE VERY SIMILAR BUT COUNTERS AND FLOORING MAY NOT BE EXACTLY THE SAME. HARD TO FIND A QUALITY NEW BUILD AT THIS PRICE AND THEY GO QUICKLY ONLY 3 MORE LOTS LEFT AFTER THIS ONE. BUYER PAYS ALL RECORDATION AND TRANSFER CHARGES AND ANY CLOSING COST HELP IS ADDED TO THE PRICE. MHBR #3717

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,848
Status:
Active
MLS#:
MDKE117156
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.08 Acres
Year built:
1900
Courtesy: Gunther-McClary Real Estate
View additional info

Want to live on one of Chestertown's most desirable streets? Look no further! The lovely home boasts hardwood flooring, tall ceilings, elegant molding and trim, and ornate oversized windows. Main floor features an inviting living room, formal dining room, large kitchen, full bathroom, and mudroom/laundry room. Upstairs you'll find 4 large bedrooms. Two are located on the 2nd floor with a full bathroom and two others on the 3rd floor. There's space for everyone! Welcoming front porch is the perfect spot to greet guests. Private and spacious backyard with patio and shed complete this unique home. The possibilities are endless. Only 2 blocks from the Chester River. Close to restaurants, shops and schools. Make this place your home!

Beds:
4
Baths:
2 Full
Sq.Ft.:
2,284
Status:
Active
MLS#:
MDKE117142
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
1.54 Acres
Year built:
1975
Courtesy: Select Land & Homes, LLC
View additional info

Mill Creek Waterfront, situated at the end of a quiet cul-de-sac in Chesapeake Landing within a short ten minute drive to Chestertown or Rock Hall. This 1.5+ /- wooded acre point of land is bordered on two side s by the creek. One side slopes gently to the creek and the other offers elevated views of water, marsh and unspoiled woodland. An abundance of wildlife including deer, turkeys, herons, eagles and waterfowl frequent the property and surroundings. This site offers access to Mill Creek for canoe, kayak, and paddle board. Chesapeake Landing has a small marina for larger boats, Worton Creek Marina offers marine maintenance and slips for larger boats, and there is also a County Landing near by. The residence offers views of the creek from most rooms in the recently upgraded raised rancher. There are two bedrooms, living areas with fireplaces, and kitchens on both levels. The waterside barn is in need of repairs but serves as a perfect building for watersport equipment storage, woodshop, " man cave" or "she shed". This is the ideal property to getaway from it all and decompress from the hustle and bustle of a fast paced lifestyle. Utility easement runs with the property.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
2,408
Status:
Active
MLS#:
MDKE117148
Type:
Single Family, Single Family-Detached
Subdivision:
Heather Heights
Lot size:
0.8 Acres
Year built:
1976
Courtesy: Cross Street Realtors LLC
View additional info

This Heather Heights jewel has had quite the transformation - the main level features a tastefully updated/upgraded kitchen with breakfast nook, hardwood flooring, built-ins, separately zoned spacious master suite with reading/sitting room, walk-in closet with custom built-ins and laundry + large master bathroom... the upper level boasts 4 bedrooms and 2 full bathrooms. The basement offers generous storage capacity and game area, all of which is protected by a french drain system... The garage is even heated and cooled!

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:
4
Baths:
2 Full
Sq.Ft.:
1,820
Status:
Active
MLS#:
MDKE117068
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee Creek
Lot size:
5.05 Acres
Year built:
1993
Courtesy: Gunther-McClary Real Estate
View additional info

Best of all worlds. with 5+ acres of private woodland. This waterfront home has very easy water access and natural surroundings. Located on Fairlee Creek, just minutes from the Chesapeake Bay. Just feel the peace that engulfs you as you look out from the many windows of the great room. Boat, walk, bike, or drive to a marina, golf course, tennis, pool, restaurants and beach. A perfect Eastern Shore retreat. Co-broke commisssion will not be paid unless co-broke arranges and attends all showings

Beds:
4
Baths:
3 Full
Sq.Ft.:
3,136
Status:
Active
MLS#:
MDQA145180
Type:
Single Family, Single Family-Detached
Subdivision:
Pheasantfield
Lot size:
37.09 Acres
Year built:
1995
Courtesy: Hagan Realty
View additional info

This 37-acre waterfront farm offers endless possibilities and an exceptional opportunity to generate multiple streams of income! The property backs to the Chester River and is one of the top duck hunting locations in the county. Kayak and canoe right from your own backyard or go across the street to Deep Landing to launch larger boats. The main level of the home boasts 3 bedrooms, 2 full baths, and new laminate flooring in a wood finish. The basement is a full in-law suite complete with a separate entrance, kitchen, living room, bedroom, full bath, and a bonus room that can be used as a bedroom or an office. The equestrian amenities are countless with a 25-stall barn, 11 pastures, a small indoor arena suitable for lunging or starting young horses, automatic waterers, 2 large run-in sheds, a large garage for vehicle or equipment storage, and more! The pastures were thoughtfully designed for handling foals and young horses and the wide trails through the woods are excellent for riding.

Refine Property Search
Page 1 | 2 | 3 of 3    Prev | Next
1–25 of 68 properties displayed

How may I help you?

Get property information, schedule a showing or find an agent






We respect your privacy