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Chestertown MD Real Estate & Homes for Sale

132 Properties Found

The median home value in Chestertown, MD is $225,000 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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$129,900

610 High Street Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9988524
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.1104 Acres
Year built:
1900
A broker reciprocity listing Courtesy: The Hogans Agency Inc.
View additional info

Spacious and affordable home located near the heart of Chestertown. Walking distance to fine arts, restaurants and waterfront. Great location, close to elementary school and Washington College. Hardwood throughout with a large eat-in kitchen and recently renovated bathroom. Sizeable yard and off street parking.

$229,900

108 Longfellow Drive Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
QA9987143
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.3444 Acres
Year built:
1974
A broker reciprocity listing Courtesy: Keller Williams Select Realtors
View additional info

Just remodeled! This beautiful 3 bedroom 2 bath home has 2 master suites! Open floor plan. Large bedrooms and closets. New kitchen with granite counters, ceramic tile, new appliances. All new ceramic tile baths. New HVAC, roof, paint, carpet, fixtures. Bonus room can be office or den. Large fenced yard. Detached, 2 car garage. Covered deck. Fenced rear yard. Professionally landscaped.

$186,000

8890 Fairlee Rd Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,232
Status:
NEW LISTING
MLS#:
KE9985575
Type:
Single Family
Subdivision:
Fairlee
Lot size:
0.2434 Acres
Year built:
2016
A broker reciprocity listing Courtesy: Long & Foster Real Estate, Inc.
View additional info

5 miles from Chestertown and $6000 in sellers help will allow you to live in this lovely new home in Fairlee. Master suite has a full bath and double vanity. Open living area with a large Kitchen/Dining rm with center island too!. Great yard and outdoor entertaining on the deck!!! Take a look, it is worth it!

$295,000

202 Cannon Street Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9983012
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.0328 Acres
Year built:
1924
A broker reciprocity listing Courtesy: J2 Real Estate
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Simply charming 3BR/2.5BA ideally located a block and a half b/t the water and historic downtown. Character abounds featuring HWF throughout, great floorplan/flow, fantastic light, SS appliances, eat-in breakfast nook, wetbar, spa-like master suite w/walk-in closet, clawfoot tub, exposed brick, finished artist loft, and abundant basement storage. Fabulous rear garden with masonary stone tiles.

$184,900

870 Washington Avenue Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
1,454
Status:
Active
MLS#:
KE9981721
Type:
Single Family
Subdivision:
Chester Heights-Rt 213 N
Lot size:
0.2066 Acres
Year built:
1956
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

This adorable bungalow can be residential or commercial. Conveniently located right on Rt. 213 with Redners, Verizon, UPS Store, McDonald's & more across the street. 3 bedroom or office spaces with 1 bathroom and screened in porch. Come take a peek!

$154,900

Poplar Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9981640
Type:
Single Family
Subdivision:
Quaker Estates
Lot size:
0.3289 Acres
Year built:
2017
A broker reciprocity listing Courtesy: Rosendale Realty
View additional info

THIS HOME PACKS A LOT INTO THE PACKAGE. LARGE OPEN LIVING & KITCHEN GIVE IT AN OPEN AIRY FEEL. SPLIT FLOOR PLAN, COZY HEAT PUMP, SEP LAUNDRY NICE KITCHEN APPLIANCE PACK ALL IT WORTH THE WAIT TO HAVE IT BUILT. CONTRACT NOW FOR EARLY 2018 DELIVERY. BUYER MAY SELECT MOST EVERYTHING FROM BUILDERS SAMPLES. MULTIPLE LOTS AVAILABLE MHBR #3717 PICS ARE OF A PREVIOUSLY CONSTRUCTED HOME.

$689,000

7703 Waterview Lane Chestertown, MD 21620

Beds:
3
Baths:
4.00
Sq.Ft.:
3,257
Status:
Active
MLS#:
KE9980579
Type:
Single Family
Subdivision:
Country Club Estates
Lot size:
0.9183 Acres
Year built:
1969
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

If your golf game had as much attention to detail as this stunning country club home, you'd be a Pro! Situated just off the 13th hole, this timeless design radiates both elegance & comfort while expansive views over the course to the Chester River relax the soul. 2 master suites, gourmet kit, wet bar, great room, library, apartment, generous/custom storage capacity & an abundance of built-ins...

$249,900

8550 Camp Road Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
2,968
Status:
Active
MLS#:
KE9977957
Type:
Single Family
Subdivision:
Kent Acres
Lot size:
0.545 Acres
Year built:
1973
A broker reciprocity listing Courtesy: Keller Williams Integrity
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An amazing opportunity for home ownership awaits you in this charming brick rambler! HDW floors span Liv/DinRMs w/gasFP& bayWIN. Spacious KIT offers corian counters, solid oakCABS &sunken BrkfstRM w/access to brick patio& private BY w/serene views! Rest easy in ML MDB w/2xCL &attBA or entertain in sprawling FinLL feat. FamRM w/WBFP& built-ins, GameRM, RecRM& BonusRM w/halfBA& outdoor access!

$309,900

326 Devon Drive Chestertown, MD 21620

Beds:
5
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9972032
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.2312 Acres
Year built:
2008
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
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Located in the desirable Coventry Farms community just 2 miles from Downtown Chestertown, this property is a cut above the rest! Meticulously maintained over the years w/ ALL the upgrades, this 3,168 sf, extremely clean home is move-in ready. Spacious kitchen, large morning room, luxury master suite with cathedral ceilings, finished basement with powder room, low-maintenance Trex decking, & more!

$510,000

7740 Country Club Lane Chestertown, MD 21620

Open House:

Saturday, 7/1 11:00-2:00PM

Beds:
5
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9958346
Type:
Single Family
Subdivision:
Country Club Estates Add
Lot size:
0.542 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous 5 Bedroom, 3 Full Bath home in Country Club Estates. Large eat-in Kitchen with granite counters, built-in Bar, wine racks, Sun Room, 3-Season Porch, Dining Room, Family Room, Marble tile in Master and 2nd Bath. Brick Patio and grilling area, Extensive landscaping backing to woods and creek. Close to the Country Club, Chester River and Historic Chestertown.

$116,600

210 Hilltop Lane Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
KE9972262
Type:
Townhouse
Subdivision:
Tim Dills Sub
Lot size:
0.0667 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Real Home Services and Solutions, Inc.
View additional info

Auction property. 4.5% Buyer Premium charged buyer at closing. No inspection contingency accepted. REO Property sold As-Is w/o repair, warranty or Seller Disclosure. The Listing Broker & Seller assume no responsibility & make no guarantees as to the accuracy of info herein. Seller will accept cash, conventional, 203k offers only. No water activation allowed. Buyer pays entire transfer tax.

$388,500

9822 Fairlee Cove Drive Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9971918
Type:
Single Family
Subdivision:
Fairlee Cove
Lot size:
0.8445 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Beautiful remodeled home situated on Fairlee Creek, just minutes from the Bay. Some updates to this cozy home include stainless appliances, upgraded HVAC system and a wood ceiling. Entertain and enjoy the fenced yard or relax on the deck with shade from many mature trees. Just a short walk away, keep your boat and jet skis ready to go at the private dock that has a power lift and floating dock.

$475,000

10836 Foreston Road Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9970311
Type:
Single Family
Subdivision:
Private
Lot size:
1.34 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous price on the this amazing waterfront home! Bring the family & friends to enjoy the waterfront. Plenty of room for everyone! Quality built home with open easy flowing floor plan. 4 Bedrooms & 3 full bathrooms. Great Room on main level that opens to large screened-in porch & deck. Large family room has bar & opens to steps down to water & dock. Take boat to Bay or kayak Worton-Mill Creek.

$125,000

340 Pine Tree Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9968880
Type:
Single Family
Subdivision:
None
Lot size:
12 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Rosendale Realty
View additional info

Build your dream home on 12 Acres of mostly wooded property. Peaceful country setting in Queen Anne's County convenient to 301. Enjoy the small stocked pond and private wooded acres for nature watching or hunting. Existing home is a tear down but shed just needs a new roof. Do not enter home. Enter shed at own risk.

$177,000

501 Kent Street N Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9967627
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.3352 Acres
Year built:
1965
A broker reciprocity listing Courtesy: RE/MAX First Choice
View additional info

Great opportunity in this 3 bedroom 2 bath home! Hardwood floors, separate dining room, formal living room, screened in porch and more!

$37,900

2007 Pondtown Road Chestertown, MD 21620

Beds:
1
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9965712
Type:
Single Family
Subdivision:
Pondtown
Lot size:
4 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

CALLING ALL TINY HOUSE ENTHUSIASTS!! Live small and reduce your footprint in this simple home on 4 ACRES!! Room for a garden, live off the land in the country! Home needs TLC so come with a CAN DO ATTITUDE! The price is right, so COME ON DOWN!

$149,500

108 Malone Avenue Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9965353
Type:
Single Family
Subdivision:
Foxley Manor
Lot size:
0.365 Acres
Year built:
1962
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Nice home in chestertown. Close to everything and ready to move into. Walk out basement makes convenient shop area and extra living space that is sectioned off. Open living room and kitchen area creates such a bright open area. Visit and add your personal touches to make it home.

$315,000

111 Maple Avenue Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9959108
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.1242 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

The charm of yesteryear is found throughout this lovely Victorian. Wood floors, high ceilings, fireplaces, porches and more add to the historic feel. New gourmet kitchen with granite countertops and cherry cabinets is simply beautiful. Close to restaurants, shops, Chester River and Washington College.

$349,000

10202 John Carvill Road Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
3,250
Status:
Active
MLS#:
KE9961390
Type:
Single Family
Subdivision:
Great Oak Estates
Lot size:
3.26 Acres
Year built:
1984
A broker reciprocity listing Courtesy: The Hogans Agency Inc.
View additional info

Modern, large rancher updated with 3 car garage (1152 sq ft), pole barn (1080 sq ft) with 2 garage doors, deck and patio. Located in water privileged community of Great Oak Estates. Amenities include 9 hole golf course, beach, pool and boat ramp at Great Oak Marina. Has 35 KW propane generator. Appraised value is $420,000. Great bargain.

$112,000

8895 Queen Anne Street Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
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.

$265,000

133 Queen Street UNIT 1 Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
1,685
Status:
Active
MLS#:
KE9958213
Type:
Condo/Townhouse
Subdivision:
Chestertown Historic District
Year built:
1873
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 known 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:
Active
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
View additional info

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:
Active
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.
View additional info

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.

$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.

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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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