Chestertown MD Real Estate & Homes for Sale

115 Properties Found

The median home value in Chestertown, MD is $212,500. 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 $212,500. 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!
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$174,900

116 Fairview Drive Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
QA9897064
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.45 Acres
Year built:
1976
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Move-In Ready!! This 3 BR, 1 BA rancher features new HVAC with a lifetime guarantee transferrable to one owner, new BAT septic system, new roof, new flooring, new kitchen appliances, lead free certificate and freshly painted throughout. Located in a water oriented community with optional HOA minutes from Chestertown and walking distance to Round Top Park.

$181,720

10577 Watonga Road Chestertown, MD 21620

Beds:
4
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9896607
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.47 Acres
Year built:
2003
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

This property is now under auction terms. Please contact an agent for more info on how to purchase this home. This property is subject to a 5% or $2,500 minimum buyer's premium pursuant to the Auction Terms & Conditions.

$199,000

24039 Chestertown Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9895172
Type:
Single Family
Subdivision:
Chesapeake Estates
Lot size:
0.46 Acres
Year built:
1970
A broker reciprocity listing Courtesy: Keller Williams Select Realtors
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Beautifully renovated rancher conveniently located on Chestertown Road. Upscale renovation. Totally new interior - HVAC, plumbing, electric, insulation, drywall, doors. flooring, lighting, paint, appliances, water heater. Ceramic tile baths. Upgraded kitchen appliances and granite counters. Recessed lighting. New carpet and paint. Detached garage. Nice level lot backing to farm land. Easy to show.

$107,000

218 Concord Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
QA9893331
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.43 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

Nice rancher with a split floor plan- three bedrooms and two baths. Kitchen is large and there's a screened back porch. Good storage and closet space. It has everything you need to start out. Located in Chester Harbor. Sold as-is.

$160,000

10767 Carimon Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9890820
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.41 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Great home in water-access community of Chesapeake Landing offers recent updates including new flooring, as well as an updated bathroom & kitchen. The property backs to woods and wetlands and has a fenced rear yard, outdoor sitting area w/ fire pit & rear deck for outside entertaining. Well maintained & landscaped w/ mature trees, this property is move-in ready!

$385,000

206 Queen Street Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9889259
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.19 Acres
Year built:
1900
A broker reciprocity listing Courtesy: RE/MAX Executive
View additional info

Lovely home located in Chestertown's Historic District. Beautiful wood floors throughout. Huge family room addition in rear. Large formal dining room with French doors to living room. Gas insert in living room fireplace could be converted back to wood burning. Wonderful front porch. Take a look today - turn of the century charm awaits you.

$370,000

7 Cedar Chase Court Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
2,397
Status:
Active
MLS#:
KE9889244
Type:
Single Family
Subdivision:
Miletree Village
Lot size:
0.48 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Coldwell Banker Residential Brokerage
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Intimate, traditional home, with big views of the Chester river & private pond. Central location to town, located on a quite cul-de-sac ! Large deck & screened porch, ready for your grilling parties on the deck with water views. Kitchen up-dated with tile back splash, Fire place, elevator, two car plus garage, main floor master bedroom, screened porch. bonus space, to be possible finished.

$473,500

213 Birch Run Road Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
2,444
Status:
Active
MLS#:
KE9887802
Type:
Single Family
Subdivision:
Mile Tree Village
Lot size:
0.46 Acres
Year built:
1998
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Co
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Eastern Shore home offers expert craftsmanship and is ideally set in a quiet neighborhood just a short walk from historic Chestertown and Washington College. Renovated home with first floor master suite has spacious rooms and an open main living area inviting casual living and entertaining. Kitchen with granite countertops opens to the screened porch overlooking the professionally landscaped yard.

$314,900

200 Camelot Drive Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9884075
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.27 Acres
Year built:
2010
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
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Beautiful home, corner lot in Coventry II. Pool is only a couple of years old, beautiful hardscaping. Central vac, wood burning fireplace, sitting area off the kitchen, fully finished basement that was finished very nicely, with a craft/sewing room and a work out area. Many amenities, huge master suite, four bedrooms, 2.5 baths. Two car side loading garage. Must see!

$369,000

10202 John Carvill Road Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9883067
Type:
Single Family
Subdivision:
Great Oak Estates
Lot size:
3.26 Acres
Year built:
1984
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
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Seasonal water view of Fairlee Creek, wood floors, detached garage (1152 sq feet) with 3 garage doors, a pole barn that' 1080 sq feet, with electric and garage door. Deck, wood floors, wood stove, updated kitchen with quartz countertops, 35 kw Cummins propane generator, propane tank is owned. Front patio with fountain, very privately landscaped. Priced below appraisal!

$199,900

209 Creston Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
1,056
Status:
Active
MLS#:
QA9880989
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.35 Acres
Year built:
1976
A broker reciprocity listing Courtesy: The Hogans Agency
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Located in a water-oriented community just min. from downtown Chestertown, this 3 bed 1 bath home on .35 acre corner lot is the perfect starter home! This move-in ready home features new central AC/Heat in the past 5 years, new roof in the past 6 months, new vinyl siding, exterior windows and doors installed with the last 9 months, as well as recent updates to the kitchen and bathroom.

$284,500

7885 Whitworth Court Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,720
Status:
Active
MLS#:
KE9880109
Type:
Single Family
Subdivision:
Heather Heights
Lot size:
0.93 Acres
Year built:
1979
A broker reciprocity listing Courtesy: Davis Real Estate, Inc.
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Low maintenance home in excellent condition located near Chestertown, Chester River Yacht and Country Club with access to the Chester River. New roof and windows in 2016. New heat pump and interior paint in 2017. Home shows well and possession is after July 1, 2017.

$646,000

7980 Airy Hill Road Chestertown, MD 21620

Beds:
3
Baths:
4.00
Sq.Ft.:
3,768
Status:
Active
MLS#:
KE9879580
Type:
Single Family
Subdivision:
Rural Kent County 10 Min From Chestertown
Lot size:
10.01 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Maryland Heritage Properties
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A Greg North INGENIOUS RENOVATION! Built 1987. Transformed into 18th c period home. Exquisite details - floors, light fixtures, hardware, moldings, plus. Stunning "Great Room" w brick floor & massive period fireplace & paneling. Social spaces beautifully presented. 10.1 acres (Ag. tax credits?). 3120 sf barn w/shop. Hist. period garden bldg. Asparagus, nut trees, orchard. 10 min. to C'town.

$339,900

100 Adela Way Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
3,799
Status:
Active
MLS#:
KE9878844
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.32 Acres
Year built:
2008
A broker reciprocity listing Courtesy: Long & Foster Real Estate, Inc.
View additional info

WELCOME TO RESORT LIVING ALONG THE EASTERN SHORE, STUNNING BRICK FRONT 4 BR/4 BATH HOME IS MAGNIFICENTLY UPGRADED FROM TOP TO BOTTOM! BEAUTIFUL HARD WOOD FLRS, RECESSED LIGHTING, GOURMET KIT W/GRANITE, GAS RANGE, OVERSIZED CENTER ISLAND, SUN RM W/FRENCH DOORS TO PATIO. BSMT CLUB RM IS ENTERTAINER'S DREAM W/WET BAR AND PRIVATE SAUNA. HIGH EFFICIENCY FURNACE. PARK & RIDE FROM KENT ISLAND TO DC.

$93,000

8881 Georgetown Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
948
Status:
Active
MLS#:
KE9877793
Type:
Single Family
Subdivision:
Georgetown
Lot size:
0.66 Acres
Year built:
1945
A broker reciprocity listing Courtesy: The Hogans Agency Inc.
View additional info

Nice bungalow - well kept, hardwood floors, public water and sewer. Great buy at this price. Must see to appreciate.

$199,000

118 Malone Avenue Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9870816
Type:
Single Family
Subdivision:
Foxley Manor
Lot size:
0.34 Acres
Year built:
1973
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Awesome home that has been lovingly cared for with many updates. Basement has been partially finished with a kitchenette and pellet stove. Gleaming wood floors are throughout most of the main level. Tile in the dining area. The rear covered deck is great for summer entertaining. Brick faced with with vinyl siding added in the past few years. Heat pump for heating and cooling. House Generator!

$265,000

131 Queen Street UNIT UNIT1 Chestertown, MD 21620

Open House:

Sunday, 3/26 11:00-2:00PM

Beds:
2
Baths:
3.00
Sq.Ft.:
1,684
Status:
Active
MLS#:
KE9855389
Type:
Condo/Townhouse
Subdivision:
Chestertown Historic District
Year built:
1900
A broker reciprocity listing Courtesy: Champion Realty, Inc.
View additional info

Take Advantage of this Rare Opportunity to Own One Unit of A Charming Duplex Condo in the Heart of Chestertown Historic District * Known As "The Willis Double House" * Perfect in-town Location; Walk to Shops, Restaurants, Parks,Theater and the Beautiful Chestertown, Chester River Waterfront * Just a short drive to Historic Washington College * Move-in Ready * Call Today for Your Personal Showing !

$275,000

211 Leeds Court Chestertown, MD 21620

Beds:
5
Baths:
4.00
Sq.Ft.:
2,970
Status:
Active
MLS#:
KE9861355
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.34 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Large 5-Bedroom Colonial offers a fully finished basement & a brand new composite deck! The kitchen w/ ceramic tile flooring, gas range & kitchen island opens to breakfast area & family room. Also offers a formal dining room, living room & Master Suite w/ 2 walk-in closets & large bath w/ soaking tub. Located at the end of a quiet cul-de-sac w/ 2-car garage & paved drive! Motivated Seller!

$275,000

209 Campus Avenue Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9866525
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.36 Acres
Year built:
1947
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Co
View additional info

Upgrades completed! This charming & spacious home in Chestertown, close to Washington College & walking distance to Fountain Park will sweep you off your feet. Wood floors, granite kitchen counters, screened porch and fenced backyard. Relax in this beauty and enjoy your close proximity to everything Chestertown has to offer! Beautiful yard with mature trees and a 2 car garage complete the picture.

$229,000

301 Campus Avenue Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
KE9865380
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1964
A broker reciprocity listing Courtesy: Sassafras River Realty, Ltd.
View additional info

Brick Home in Chestertown ready for you to move-in! Renovations have been made including Kitchen & A/C. Hardwood floors throughout most rooms, fireplace in Large Living Rm, bright rooms with plenty of closet space & built-in shelves. Storage area attached to carport. Blacktop driveway. Corner lot that is landscaped.

$379,900

110 Kent Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,600
Status:
Active
MLS#:
KE9861885
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.05 Acres
Year built:
1852
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Restored with superior quality - wood clapboard exterior, natural pine & slate floors, soapstone counters, detailed moldings & chair rail, shiplap pine walls in dining area, preserved interior doors, hardware, trim, stair treads & railing, french doors, brick alley & patio, new structural piers, 2 sump pumps in concrete crawlspace, new floor joists, new sewer lines, new electric, plumbing & roof!

$258,500

204 Brown Street Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9845730
Type:
Single Family
Subdivision:
None
Lot size:
0.51 Acres
Year built:
1950
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Located in a quiet Chestertown community, this spacious home offers easy access to both the local hospital and Kent County Middle School. With large family spaces and a big back yard, this house is great for those seeking either a quiet life or who are interested in entertaining.

$394,000

1530 McGinnes Road Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
2,858
Status:
Active
MLS#:
QA9845321
Type:
Single Family
Subdivision:
Not In A Subdivision
Lot size:
4.55 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Spacious home w/ privacy on 4.5+ wooded acres, including additional buildable lot, close to Chestertown & 301. Huge Master Suite w/ large en-suite bath w/ shower & claw foot tub, dressing/sitting room & walk-in closet. Brazilian cherry & bamboo flooring throughout the main level w/ an open kitchen & family area. The 2-car garage has been converted for daycare but is easily put back.

$195,000

913 Round Top Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9858146
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
2017
A broker reciprocity listing Courtesy: Rosendale Realty
View additional info

JUST A BIT OVER RESALES GETS YOU QUALITY RANCH STYLE HOME WITH OPEN LIVING AND KITCHEN. STILL TIME TO MAKE SELECTIONS AND UPGRADES AVAILABLE. MODEL UNDER CONSTRUCTION IN KENT CO. ON CEDAR AVE. ARCH SHINGLES, WOOD LAMINATE FLOORING, NICE FLOOR PLAN. LEVEL LOT WITH EXISTING SHED ON SITE FOR EXTRA STORAGE. COMMUNITY HAS VOLUNTARY HOA. MAIN PIC IS A SIMILAR HOME ON A DIFFERENT LOT MHBR # 3717

$154,982

24745 Langford Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9857177
Type:
Single Family
Subdivision:
Kent County
Lot size:
0.4 Acres
Year built:
1961
A broker reciprocity listing Courtesy: RE/MAX Associates
View additional info

3 BR / 2BA brick ranch , under construction and at point now where the contractor is offering a qualified buyer to go through a selection of finishes to completion. Budget to be determined. Showing by appointment only.

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The data on this web site comes in part from Metropolitan Regional Information Systems (MRIS). The listings presented on behalf of MRIS may come from many different brokers but all MRIS listings may not be visible on this site. Information is believed to be reliable, but not guaranteed.

Chestertown MD Real Estate Listings Provided By:

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