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Chestertown MD Real Estate & Homes for Sale

142 Properties Found

The median home value in Chestertown, MD is $217,000 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 , is $. 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 Chestertown real estate agent to arrange a tour today !
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$169,900

132 Darden Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,144
Status:
NEW LISTING
MLS#:
QA9960191
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.3512 Acres
Year built:
1986
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Special financing available! Well maintained 3 BR, 2 BA home on nice corner lot in Chester Harbor with sliding glass doors that open to a large deck. New Heat Pump April 2017. Located in a water oriented community with optional HOA minutes from Chestertown and walking distance to Round Top Park.

$112,000

8895 Queen Anne Street Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9959008
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.36 Acres
Year built:
1951
A broker reciprocity listing Courtesy: The Hogans Agency Inc.
View additional info

Close to the Bay and nearby marina this charming home could be the ideal place to bunk while you enjoy your time on the water. Approximately 10 minutes from Rock Hall and Chestertown. Easy to heat and easy to cool this could be an ideal starter home or great vacation place. The house and Parcels 530 and 531 are included in this sale making the total acreage .36 acres.

$228,900

202 Devon Drive Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9958998
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.3479 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Nice home with open living room,dining and kitchen area. Split floor plan, master with walk in closet and full bathroom to your right. To the left as you enter, two bedrooms with Jack and Jill bathroom. Full basement. This home has been well cared for gently lived in. Original owner. NOT Part of the HOA.

$265,000

133 Queen Street UNIT 1 Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
1,685
Status:
NEW LISTING
MLS#:
KE9958213
Type:
Condo/Townhouse
Subdivision:
Chestertown Historic District
Year built:
1900
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Enjoy the Best of Chestertown in this turn of the century duplex know as "The Willis Double House". Located in the heart of the Historic District with the perfect blend of period charm and modern functionality; updated kitchen and baths, hardwood flooring, large airy rooms with lots of light. Enjoy a private deck and Pocket English Garden. The perfect in-town retreat!

$490,000

127 High Street Chestertown, MD 21620

Beds:
2
Baths:
3.00
Sq.Ft.:
3,286
Status:
NEW LISTING
MLS#:
KE9956645
Type:
Single Family
Subdivision:
Downtown Che
Lot size:
0.0445 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Select Land & Homes, LLC
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Formally The Cahall Store. 4-bay square nineteenth century vernacular bldg. with Greek Revival features, Hip roof with cupola. Superior Downtown Chestertown location. Two main level offices with two 1 bedroom apartments upstairs. Fully rented with excellent tenants.Updated utilities. This is a rare offering of one of Chestertown's most attractive buildings and locations!

$129,500

614 High Street Chestertown, MD 21620

Beds:
2
Baths:
1.00
Sq.Ft.:
1,064
Status:
NEW LISTING
MLS#:
KE9955791
Type:
Townhouse
Subdivision:
Historic Chestertown
Lot size:
0.0567 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Long & Foster Real Estate, Inc.
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HISTORIC DISTRICT HOME. 2BR-1Bath,1064sqft. Semi-detached TOWNHOUSE w/large fenced back/front yards. Porch holds seating. Back yard LOCKABLE Storage SHED. Street PARKING. Tilt-out Insulated WINDOWS. Updated KITCHEN/BATH. Hardwood FLOORS.APPLIANCES convey. Few blocks from HISTORIC DOWNTOWN CHESTERTOWN, Golf Course, Chester River & Wash College.SHOWS WELL!! SOLD AS IS!! 24 HR NOTICE.BY APPT ONLY.

$1,795,000

6324 Quaker Neck Road Chestertown, MD 21620

Beds:
5
Baths:
4.00
Sq.Ft.:
5,938
Status:
NEW LISTING
MLS#:
KE9955543
Type:
Single Family
Subdivision:
N/A
Lot size:
5.25 Acres
Year built:
1937
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
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Stunning waterfront retreat nestled on a 5-acre private point on Langford Creek. The gorgeous, custom built home offers incredible attention to detail, beautiful hardwood floors, gourmet kitchen, private guest quarters and a wonderful water view conservatory. The property also features a deep water dock with lifts, private beach, boat shed, 31x24 barn and carriage house above a 4-car garage.

$249,000

219 Calvert Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
2,233
Status:
Active
MLS#:
KE9954586
Type:
Single Family
Subdivision:
None
Lot size:
0.195 Acres
Year built:
1958
A broker reciprocity listing Courtesy: Long & Foster Real Estate, Inc.
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Super 2 zoneheat/AC house! Large great room w/cathedral ceilings is wonderful for entertaining. Remodeled kitchen opens to the great room. This 3 bedroom 2 bath home is accented w/wood floors throughout. The spacious living room is accented w/a fireplace for when the cooler evenings set in.The two car carport provides vehicles from the weather. The back yard is private and has a very nice patio

$179,000

9919 Flatland Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9950326
Type:
Single Family
Subdivision:
None
Lot size:
0.46 Acres
Year built:
1962
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
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This builder owned and renovated house was meant to be a forever home! All upgrades are custom and completed with care! Custom crown molding and trim were hand made. The kitchen has custom cabinets w/ concrete counters, hand hewn red oak floors and black walnut plank ceilings w/ chrome recessed lighting. Too many upgrades and custom features to mention! Within 5 miles of a Marina!

$248,000

209 Richard Drive Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,444
Status:
Active
MLS#:
KE9953718
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.3238 Acres
Year built:
1974
A broker reciprocity listing Courtesy: Champion Realty, Inc.
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BEAUTIFULLY RENOVATED HOME W/NEW ENERGY EFFICIENT WNDWS, NEW ROOF, UPDATED KIT INCLUDING GRANITE COUNTERS & SS APPL., NEW FLOORING & NEW BATHS INCLUDING TILE FLOORS, HUGE LIVING ROOM W/WOOD BURNING FIREPLACE, GARAGE, GREAT DECK, CENTRAL HEATING & AIR, LOVELY YARD, PLUS PUBLIC WATER & SEWER AND NO ASSESSMENT!

$680,000

557 Fey Road Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9953179
Type:
Single Family
Subdivision:
Chestertown
Lot size:
1.6 Acres
Year built:
1972
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Incredible views and direct access to the scenic Chester River less than 5 minutes from Historic Chestertown. Wonderful inground pool overlooking the river plus dock, boatlifts, BOATHOUSE, sandy beach and 300 feet of waterfront on 1.6 acre park-like lot. New BAT septic and complete set of architectural drawings so you can make a spectacular renovation of this solid home!

$170,000

807 High Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9950819
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.0918 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Great Potential. This fixer-upper is located within walking distance of the college, downtown, and the town waterfront. It also has great investment potential as a rental or office space. Currently used as a rental with a month to month lease in place.

$675,000

114 Washington Avenue Chestertown, MD 21620

Beds:
6
Baths:
6.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9950177
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
1.146 Acres
Year built:
1860
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

The John L Stam House, circa 1860, is a beautifully restored Gothic Revival Victorian. Currently run as a B&B there are 4 guest rooms with full baths and an additional 2 BR in the owners quarters. The first floor features original faux painted fireplaces, hand painted plastered ceilings, and "Jenny Doors" leading to a gracious veranda. A recently added water feature enhances the beautiful gardens

$104,900

516 High Street Chestertown, MD 21620

Beds:
2
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9950182
Type:
Single Family
Subdivision:
Chestertown Historic District
Lot size:
0.0597 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Keller Williams Select Realtors
View additional info

Rehab/investor potential for this single family home in Historic district of Chestertown. 2 level, 2 bedroom/1 bath home. Living room and separate dining room.Home needs repairs. Property sold as-is. Cash or rehab loans only. $177 management fee charged to buyer's agent. Submit offers thru propoffers.

$325,000

1600 Ewingtown Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
2,268
Status:
Active
MLS#:
QA9948291
Type:
Single Family
Subdivision:
None
Lot size:
4 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Keller Williams Flagship of Maryland
View additional info

Gorgeous farm house full of rustic charm situated on 4 acres! Built in the late 1800's, the farm home boasts a handcrafted wood staircase, original hardwood floors throughout, formal living & dining rooms, huge kitchen, spacious bedroom sizes and finished attic with gorgeous view of front pasture. Property offers a newer stable with 2 stalls & water, hay barn and potting shed. Bring your horses!

$300,000

321 Devon Drive Chestertown, MD 21620

Beds:
5
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9948025
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.2737 Acres
Year built:
2008
A broker reciprocity listing Courtesy: Century 21 The Real Estate Centre
View additional info

Huge colonial in sought after Coventry Farms, featuring: 5 bedrooms plus a den, 2.5 bathrooms, family room & bright morning room off the gourmet kitchen, formal dining room, formal living room, hardwood floors, recreation room in basement, 2 car garage, lot backs to woods for privacy, rough in for 3rd full bath in basement, crawl space & large unfinished room in basement for storage. HOME WARRANTY

$199,900

10141 Flatland Road Chestertown, MD 21620

Beds:
4
Baths:
1.00
Sq.Ft.:
2,035
Status:
Active
MLS#:
KE9947876
Type:
Single Family
Subdivision:
Chestertown
Lot size:
2 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Loads of upgrades have already been done on this 3 story traditional farm house. Located on spacious 2 acres and only minutes from down town Chestertown. Room to add bathroom/s or extend kitchen. Lots of charm with wood burning stove and fireplace. Cozy side porch, 3 outbuildings/sheds, gravel drive, updated windows, insulation, new deep well, and much more!

$69,500

409 Calvert Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9945288
Type:
Townhouse
Subdivision:
Calvert Homes
Lot size:
0.0467 Acres
Year built:
1992
A broker reciprocity listing Courtesy: Sommers Enterprises, Inc.
View additional info

Low maintenance, interior town home close enough to walk to all Chestertown amenities. Recent upgrades of interior painting, laminate floor installation, kitchen cabinet redo., tree trimming, new second floor & Stairs wall to wall carpeting. Park off street in rear. Consistent market rental history for investor buyers.

$299,900

209 Garland Way Chestertown, MD 21620

Beds:
5
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9944682
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.2479 Acres
Year built:
2006
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Beautiful 5 Bedroom, 2 1/2 bath home in desirable Coventry Farms just outside Chestertown. This home has a large backyard, A 2-car Garage, Family Room, Dining Room, huge Kitchen and Laundry Room with washer/dryer off of the Kitchen. A Fabulous Master Bedroom and Bath and 4 large bedrooms are upstairs; A huge basement can be finished into a Family/Play room.

$279,000

10205 John Carvill Road Chestertown, MD 21620

Beds:
4
Baths:
2.00
Sq.Ft.:
2,352
Status:
Active
MLS#:
KE9941241
Type:
Single Family
Subdivision:
Great Oak Estates
Lot size:
0.92 Acres
Year built:
1987
A broker reciprocity listing Courtesy: The Hogans Agency Inc.
View additional info

Large Cape Cod with private back yard located in water privileged community of Great Oak Estates with 9 hole golf course, beach, pool, restaurant and boat ramp at Marina.

$69,900

23308 Sandpiper Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9941005
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.4637 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

Single level living in water access community & walk to marina. Great location and very close to Chesapeake Bay, min drive to Great Oak Landing Marina, Club & Golf Course. Make this your Dream home as primary or vacation home. Perfect with large lot & Front Porch for lazy summer evening. Need little TLC and Septic is failed but has great potential & equity. Hurry won~t stay long in the market.

$194,900

515 Kent Street Chestertown, MD 21620

Beds:
4
Baths:
2.00
Sq.Ft.:
2,220
Status:
Active
MLS#:
KE9940756
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.3444 Acres
Year built:
1965
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Large home with four roomy bedrooms, a family room with a wood stove, built in cabinets and the screened porch is just off the family room. Overlooks a private, pretty back yard. Living room has a wood burning brick fireplace. Large dining room, nice generous kitchen with door that leads out to a brick patio. Full basement, a one car side facing garage. Located in Byford Heights.

$565,000

403 Cannon Street Chestertown, MD 21620

Beds:
2
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9940612
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.1206 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Benson & Mangold, LLC
View additional info

Stunning renovation, well thought out and designed! A must-see within walking distance to Historic Chestertown. Great for weekend retreats or year round living with this outdoor oasis. Off-street parking included.

$299,000

101 Kent Street Chestertown, MD 21620

Beds:
2
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9937616
Type:
Single Family
Subdivision:
Historic Downtown Chestertown
Lot size:
0.0386 Acres
Year built:
1880
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

The perfect Downtown Chestertown renovation! Refinished hardwood floors throughout the 1st floor, two master suites, backyard patio oasis, central A/C, cedar siding, butcher block kitchen countertops, plus many extras! This home is ready to host your next cocktail party on the back patio or dinner party in the spacious dining room! Have easy access to all the activities hosted Downtown!

$179,950

9028 Georgetown Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
1,128
Status:
Active
MLS#:
KE9937482
Type:
Single Family
Subdivision:
Fairlee/Chestertown
Lot size:
1.61 Acres
Year built:
1972
A broker reciprocity listing Courtesy: Champion Realty, Inc.
View additional info

THIS IS IT! Just what you are looking for. Completely updated inside: NEW: appliances, heat/AC, flooring, bathroom, kitchen, beautiful bow window for lots of natural lighting, closet doors/ shelving, ceiling fans, siding, and more all new, on a large almost 2-acre lot, complete with public water & sewer. Bring the family and visit your new home. Don't let this one get away. See today!

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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.

Chestertown MD Real Estate Listings Provided By:

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