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Chestertown MD Real Estate & Homes for Sale

126 Properties Found

The median home value in Chestertown, MD is $219,500. This is higher than the county median home value of $183,500. The national median home value is $185,800. The average price of homes sold in Chestertown, MD is $219,500. Approximately 41.87% of Chestertown homes are owned, compared to 42.32% rented, while 15.82% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


Sort Results:
1–25 of 126 properties displayed
Refine Property Search
Page 1 | 2 | 3 | 4 | 5 | 6 of 6    Prev | Next
Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
QA10303295
Type:
Single Family
Subdivision:
Royston Shores
Lot size:
0.43 Acres
Year built:
1986
A broker reciprocity listing Courtesy: Sullivan Select, LLC.
View additional info

Spectacular waterfront home located on the Chester River! Enjoy the beautiful sunset right from the family room! 2 large decks with screened in porch, large dock, new kitchen, new cork floors, upgrades throughout, detached 1 garage with unfinished space above. Master on main level, waterfront view from each bedroom!! Come and get this beautiful retreat!

Open House:

Saturday, 7/28 12:00-2:00PM

Beds:
5
Baths:
4.00
Sq.Ft.:
5,563
Status:
NEW LISTING
MLS#:
QA10303238
Type:
Single Family
Subdivision:
21 Private Acres
Lot size:
21.06 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Chaney Homes, LLC
View additional info

Hurry to this Unique Opportunity!! Over 21 Acres Ready for your Horses & Existing Vineyard- Entertainer's Delight- Nearly 5600 sq ft, 5 Bedrooms, 3.5 Baths. In-Ground Pool, Large Patio. Fenced Pasture. Large Outbuilding with 2 Stalls, Main-Level Master Suite w/ ADDITIONAL Potential In-Law Bedroom/Rec Room w/ Access to 1/2 Bath & Washer/Dryer, 3- Car Side-Load Garage,. 3 LARGE upper-level Bedrooms!

Beds:
3
Baths:
20.00
Sq.Ft.:
1,722
Status:
NEW LISTING
MLS#:
QA10301766
Type:
Single Family
Subdivision:
Kingstowne Manor
Lot size:
0.49 Acres
Year built:
1974
A broker reciprocity listing Courtesy: Long & Foster Real Estate, Inc.
View additional info

Love HGTV home transformations? Ready to give it a go right here at this lovely spot? Bring your color swatches, cabinet designs, appliance finish preferences ... and start the makeover. If you want to go at it slowly, the house is livable as it is..and does have some deferred maintenance that needs attention. Great room sizes, prime lot location for convenience and privacy.

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10302159
Type:
Single Family
Subdivision:
Downtown Chestertown
Lot size:
0.03 Acres
Year built:
1800
A broker reciprocity listing Courtesy: Select Land & Homes, LLC
View additional info

Built in 1735 and completely restored in 1977, the Buck-Bacchus House is rich with history and detail. Situated one block off the Chester River this house features hardwood floors, original fixtures and lots of character! The living room boasts a large wood burning fireplace with a Tuscan grill. The cellar is complete with heating & air and a workshop. One of Chestertowns most distinguished homes!

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10301284
Type:
Single Family
Subdivision:
Counrty
Lot size:
0.5 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

A diamond in the rough! Older farmhouse on quiet street 15 minutes outside of Chestertown and within minutes from Chesapeake Bay, marinas/restaurants. House is in need of major repairs, or possibly tear down and build the home of your dreams. Public water/sewer is a big plus! Whether you are looking for a little fixer-upper or you're a seasoned investor, this would be a great spot to call home

Beds:
3
Baths:
3.00
Sq.Ft.:
1,727
Status:
NEW LISTING
MLS#:
KE10291999
Type:
Single Family
Subdivision:
Mile Tree Village
Lot size:
0.3 Acres
Year built:
1980
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This attractive contemporary is located in sought after Mile Tree Village, quietly nestled along the river in the town limits of Chestertown. This is an artfully designed house created for one floor living offering a welcome ambiance with its wood detail and abundance of natural light. House and property are well maintained. A short walk into Historic downtown. shopping, college and dining.

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10299171
Type:
Single Family
Subdivision:
In Town
Lot size:
0.18 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Wyble Enterprises
View additional info

Attractive residence with attached garage on dead-end street, large open back-yard, fencing, hard-surface driveway, will need updating. Most windows have been upgraded to vinyl clad energy efficient. Possible investment potential. Residence occupied. Showing appointment required.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,500
Status:
NEW LISTING
MLS#:
QA10298782
Type:
Single Family
Subdivision:
Country Living
Lot size:
3.48 Acres
Year built:
2018
A broker reciprocity listing Courtesy: Brenton and Clark Realty LLC
View additional info

LESS THEN 6 MONTHS OLD, QUALITY BUILT RANCHER...Looking for the road less traveled? Relaxed, Easy Living, Inviting country charmer tucked away on 3.5 +/-acres, this one level living boasts 3 bd, 2 ba, a large open kitchen, dining & living area great for entertaining & everyday life, cathedral ceiling, recessed lighting, island/breakfast bar, SS appliances, garage & 14 x 16 deck in progress

Beds:
1
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10298267
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.32 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

First floor has been completely updated with a new bath, new kitchen, new flooring, fresh paint. Super cute one bedroom chalet with an outdoor shower, a one car garage, but two bays, and one is a workshop area. Stack washer/dryer, and water conditioner located in workshop area on main level. Very cute home, slider to outside as well. Limited peek of water & access thru private beach. .

Beds:
3
Baths:
1.00
Sq.Ft.:
1,224
Status:
Active
MLS#:
KE10293902
Type:
Single Family
Subdivision:
Chester Heights-Rt 213 N
Lot size:
0.21 Acres
Year built:
1949
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

ATTENTION!!! SELLER OFFERS $10,000.00 CREDIT TOWARDS CLOSING ASSISTANCE AND/OR IMPROVEMENTS, WITH FULL PRICE OFFERS! HOME WARRANTY IN PLACE UNTIL FEB 2019! Ready for your own touch! Walk or Bike to all amenities, food/shopping and Washington College! Nice large basement for extra storage as well! GREAT opportunity for home based business too! Home had TOTAL Renovation in 2006! Home sold As-Is!

Open House:

Saturday, 7/28 11:00-1:00PM

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10296136
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.21 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Select Land & Homes, LLC
View additional info

An upgraded colonial home on revitalized Cannon Street. This home features hardwood floors throughout, upgraded kitchen and baths, vaulted ceilings, central HVAC, first floor powder room, and a Tulikivi pizza oven! Outside is a custom two story workshop with electric, gardens, and fenced backyard. Property also has rear alley access. A must see to appreciate! Offered below the appraised value.

Beds:
5
Baths:
4.00
Sq.Ft.:
5,367
Status:
Active
MLS#:
KE10295204
Type:
Single Family
Subdivision:
Gorgeous & A Must See! Like New!!
Lot size:
13.17 Acres
Year built:
2006
A broker reciprocity listing Courtesy: Champion Realty, Inc.
View additional info

This is it!! Fabulous Custom-Built Home to the highest standards boasting a modern open floorplan, Chef's Designer kitchen including, What! - 3 Ovens!!, Outer Banks inspired wall of glass in family room w/FP, 5367 sf + 2500 sf basement & woodstove, 20x22 screened porch, second floor balcony overlooking FR & kit, gleaming hardwood flrs, Awesome home for entertaining perched on over 13 acres-Hurry!

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10295125
Type:
Single Family
Subdivision:
Fannell's Meadow
Lot size:
2.84 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

The peaceful setting & glorious garden of this post and beam reflect the civilized pace of the Eastern Shore while modern conveniences & quality details let you enjoy the rustic setting w comfortable ease. The cathedral ceiling gives a lodge feel to the LR & the brick FP ensure a cozy backdrop for every cool or snowy day. A kitchen renovation added shaker style cabinets and granite counters.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,682
Status:
Active
MLS#:
KE10289959
Type:
Single Family
Subdivision:
Fairgale Properties
Lot size:
2.72 Acres
Year built:
2000
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Located in an exclusive water-oriented community, this magnificent home offers an open plan design for those who enjoy entertaining and being active. The prominent eye-catching architectural style of the interior accents a classic paint scheme throughout. Various seating spaces, lavish main level master suite, large kitchen, sunroom, bonus room, 4 zones, 3-bay garage, deeded boat slip with 4' MLW

Beds:
2
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10290907
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.34 Acres
Year built:
1992
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Super cute, tidy home on Glenola just a few yards from the Marina & Harbor House. Chesapeake Landing location, you can join the HOA and have water privileges. Enjoy peace and quiet, just a short ride from Chestertown. This home could be three bedrooms, owner opted to have a laundry room. Open kitchen/living room. Great outdoor entertaining space with an above ground pool that can be removed

Beds:
5
Baths:
4.00
Sq.Ft.:
4,416
Status:
Active
MLS#:
KE10287497
Type:
Single Family
Subdivision:
Fairgale Properties
Lot size:
1.95 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous Water Front Beauty. Perfect in every detail! Gleaming wood floors, 4 fireplaces. Gourmet Kitchen with High End appliances. Master suite with gorgeous Bath, extra large walk in closet and deck. Living Room has tray ceiling and built-in cabinets/shelves. Enjoy the lovely views of landscaping and Fairlee Creek. 3.5 bay garage. Deep water slip has 10,000 lb metal boat lift, a short walk away.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,934
Status:
Active
MLS#:
KE10289289
Type:
Single Family
Subdivision:
Fairgale Properties
Lot size:
20.18 Acres
Year built:
2018
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Build your waterfront dream home on this little slice of heaven, offering the best of both worlds with 20+ acre of farmland and fringe woodlands on Fairlee Creek, with deeded slip at the private community dock with deep water! Hunting, fishing, horses, waterfront homestead...there are so many possibilities to enjoy the Eastern Shore lifestyle! Pictures show options & upgrades that can be built.

Beds:
1
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10288755
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.18 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Nice home lot on quiet road in Tolchester Estates. 2 extra lots convey with house making it a corner lot (Bayview and Tennessee) with possible water views of the Chesapeake Bay. Speak with county regarding setbacks and restrictions. Tolchester is a water privileged community wit a sandy beach, boat launch, and some of the best sunsets on the eastern Shore!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,138
Status:
Active
MLS#:
KE10287082
Type:
Single Family
Subdivision:
Lovely Cove
Lot size:
3.28 Acres
Year built:
1966
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Nature's paradise on Lovely Cove-enjoy a short and peaceful boat ride from your dock to the East Fork of Langford Creek. This unique waterfront residence celebrates 180 degrees water view, available from virtually all rooms. Outbuildings include garage area, workshop, storage, and potting shed.Over 3 1/4 acres of woods, cleared and privacy. Your own dock and 9 Ft. wide concrete launching ramp.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,485
Status:
Active
MLS#:
KE10286898
Type:
Single Family
Subdivision:
None
Lot size:
0.69 Acres
Year built:
1962
A broker reciprocity listing Courtesy: Rock Hall Properties Real Estate
View additional info

Private setting on over 1/2 acre close to Chestertown, this remodeled 4BR, 2 bath brick cape cod has lots of great outdoor features like the in-ground pool, decks & cabana. Inside there are newer wood floors & like new kitchen with granite counter-tops and newer appliances. Over-sized 1 car garage and paved driveway. Driveway is shared with neighbor. House next door is also for sale.

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10285771
Type:
Single Family
Subdivision:
Kent County
Lot size:
1.35 Acres
Year built:
2009
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Conveniently located between Chestertown and Rock Hall, this home offers country living at it's best. Situated on 1.35 acres, additional acreage available(2*/-). Just off Rt20 surrounded by farmland, only minutes from popular restaurants and marinas. No HOA,1680 sqft split floor plan main level and a full finished basement 9' ceilings and full bath. Do Not Enter Property Without Agent

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10284953
Type:
Single Family
Subdivision:
Kingstown
Lot size:
0.2 Acres
Year built:
1930
A broker reciprocity listing Courtesy: EShore
View additional info

Two story thoroughly remodeled Victorian with Chester River views. Short walk to river. Two bedrooms, but room for more. Great move-in condition, low maintenance exterior. Master bedroom with enclosed porch with river views. Separate shop/shed. Living room with stone fireplace, separate dining room. All appliances included.

Beds:
2
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10284541
Type:
Single Family
Subdivision:
None
Lot size:
0.5 Acres
Year built:
1959
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

Investment Potential! Small rancher in the country just outside town and not far from the country club in need of your vision and care. Come make this house your home!

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10275074
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.48 Acres
Year built:
1963
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Affordable water front home with 40' ft x 6' wide pier + 10'x 14' "L" at end and 2800 pound boat lift with electric + water. Cozy modular home on full basement. Lovely screened-in porch to enjoy the water-views and some crabs. Retro look with panel walls + 1960's bath + kitchen.Well maintained. Very private quiet location. Perfect retreat from the city, or full time retirement on the water.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,152
Status:
Active
MLS#:
KE10280653
Type:
Single Family
Subdivision:
None
Lot size:
3 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Move in ready 3 bedroom, 2 bath rancher on secluded 3 acres. Close to Chestertown. Perfect for your chickens and dogs.

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.

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