Chestertown MD Real Estate & Homes for Sale

The median home value in Chestertown, MD is $211,500. 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 $211,500. 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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Type:
Single Family
Sq.Ft.:
1,144
Status:
NEW LISTING
Beds:
3
Lot size:
0.38 Acres
Year built:
1992
Baths:
2.00
MLS#:
MDQA136802
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

Beautiful 3 BR, 2BA Rancher situated on a corner lot with mature shade trees. New dog kennel installed. Separate laundry room off of the kitchen. Nice 10 x 15 screened in porch.

Type:
Single Family
Sq.Ft.:
1,804
Status:
NEW LISTING
Beds:
4
Lot size:
0.24 Acres
Year built:
2009
Baths:
3.00
MLS#:
MDKE113878
Subdivision:
Coventry Farm

ADDITIONAL INFORMATION

Updated home with new flooring, fresh paint, and shows so well. Come and check out this cute, well priced home in Coventry II. Close to Chestertown, with four bedrooms, and 2.5 baths. Nice den/family room in partially finished basement. Fenced back yard, with a nice patio and well landscaped. Such a nice place to call home!

Type:
Single Family
Sq.Ft.:
2,496
Status:
Active
Beds:
3
Lot size:
0.52 Acres
Year built:
1960
Baths:
1.00
MLS#:
MDQA136696
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

Nicely maintained (original owners) rancher in Chester Harbor. Perched on a hill with oversized lot and overlooking fields. House is fixer-upper but with loads of potential and good bones. Bonus family room off kitchen has separate entrance and flued for a wood stove. Hardwoods throughout with vinyl in kitchen and bath. Large separate laundry with back entrance. Kitchen is spacious with dining area and solid wood cabinets. New metal roof 2017! 3 separate lots behind house ( on Concord) also available at $39,900.

Type:
Single Family
Sq.Ft.:
1,280
Status:
Active
Beds:
3
Lot size:
0.09 Acres
Year built:
1992
Baths:
3.00
MLS#:
MDKE113428
Subdivision:
Chester Arms

ADDITIONAL INFORMATION

3 BR Duplex style Townhome with recent upgrades and renovations including all new carpet & vinyl flooring and newly installed 6 panel white interior doors. Large Anderson windows allow for ample natural light. Kitchen upgrades include new countertops, sinks, faucets and dishwasher. Entryway opens to large living area. Separate dining area or second living area adjacent to kitchen. Bathrooms with new toilets. 3 BR upstairs with adjoined full bath. Entire home professionally painted. Back porch has large storage area. Back yard lined with trees add extra privacy. Home is located on quiet dead end street in Historic Chestertown, home to Washington College. Historic shops, restaurants, inns, waterfront and marina are within 1-2 miles. This property will make a wonderful home or investment rental property.

Type:
Single Family
Sq.Ft.:
785
Status:
Active
Beds:
1
Lot size:
11.05 Acres
Baths:
1.00
MLS#:
MDKE112628
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Luxury Apartments for rent. One, two and three bedroom apartments available from $895- $1,295 per month plus utilities. All apartments have wall to wall carpet, stove, refrigerator, dishwasher, microwave, washer, dryer, walk in closet, oak cabinets and garbage disposal. Located near Washington College and walking distance of downtown Chestertown, shopping, churches, and hospital. NO PETS.

Type:
Single Family
Sq.Ft.:
1,900
Status:
Active
Beds:
3
Lot size:
0.05 Acres
Year built:
2004
Baths:
3.00
MLS#:
MDKE110396
Subdivision:
Oak Hollow

ADDITIONAL INFORMATION

Lovely 3 bed/2.5 bath townhouse with large family room, eat-in kitchen, bonus room on main floor that could make a 4th bedroom, bedroom-level laundry and much more. Move-in ready and ready for a new owner to call it home! Call today to schedule a showing!

Type:
Single Family
Sq.Ft.:
2,008
Status:
Active
Beds:
3
Lot size:
0.32 Acres
Year built:
2010
Baths:
3.00
MLS#:
MDKE107880
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

9 year old cape with wonderful open floor plan. Nestled in the woods for privacy. Bay water privileges and marina nearby. This property is part of Tolchester Estates.

Type:
Single Family
Sq.Ft.:
2,722
Status:
Active
Beds:
3
Lot size:
0.14 Acres
Year built:
2015
Baths:
3.00
MLS#:
MDKE107934
Subdivision:
Historic District Chestertown

ADDITIONAL INFORMATION

Located in historic Chestertown, this home was built in 2015 and is gorgeous. Offers upgrades such as wood floors, gas fireplace, open living room/dining room, with an open kitchen. There is a first floor master suite, a laundry room, a screened porch, semi private picket fenced back yard. So much to love about this home! Detached garage with additional storage. There are three bedrooms all today, with two large rooms upstairs and a large bath. Just a short jaunt to all the fun in downtown Chestertown.

Type:
Single Family
Sq.Ft.:
3,371
Status:
Active
Beds:
4
Lot size:
0.68 Acres
Year built:
1900
Baths:
3.00
MLS#:
MDKE110538
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

PRICE IMPROVEMENT - MOTIVATED SELLERS! Impeccably maintained 4 bed/2.5 bath home with income unit attached! Zoned 'Village', it would be perfect as a multitude of things including: restaurant, deli/general store, florists shop, taxidermists, mechanic/car parts store... you name it! (2,444 sq.ft.) On over a half acre set in Quaker Neck, yet only about 5 miles from Downtown Ctown!

Type:
Single Family
Sq.Ft.:
1,584
Status:
Active
Beds:
3
Lot size:
48 Acres
Year built:
1973
Baths:
3.00
MLS#:
MDKE110432
Subdivision:
000

ADDITIONAL INFORMATION

A rare offering in an ideal location. 48 acres of farm fields,woods, waterfrontage w/ deep water & expansive panoramic views, prime hunting including puddle & diving ducks, turkey, deer, rockfish, multiple blinds, pond, oak tree-lined driveway, ranch house situated in an excellent spot w/ spectacular water views,easy access to the water, large detached garage and additional shed/barn, privacy...

Type:
Single Family
Sq.Ft.:
1,528
Status:
Active
Beds:
3
Lot size:
0.46 Acres
Year built:
1953
Baths:
1.00
MLS#:
MDQA124126
Subdivision:
None

ADDITIONAL INFORMATION

Welcome home! You will fall in love with this beautiful home. Charming kitchen, hardwood floors, new carpet, granite countertops, full basement, living room separate dining area, family room, three bedrooms and an appealing front porch. House is on a large corner lot close to all of the delightful attractions of Chestertown.

Type:
Single Family
Sq.Ft.:
2,940
Status:
Active
Beds:
5
Lot size:
0.2 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE107910
Subdivision:
Historic District Of Chestertown

ADDITIONAL INFORMATION

Priced below appraised Value!! Incredible home.. "The Pink Lady" This Victorian has been given a new lease on life with a completely updated, gorgeous new kitchen, shining floors, washer and dryer on kitchen level. This house is beautiful. Great location, within steps to downtown shopping and restaurants, and just a couple of blocks from the Chester River. There is parquet flooring, new kitchen cabinets, granite countertops, a breakfast room, new windows, beautiful stainless glass windows going up the classically beautiful staircase. Five bedrooms all total on the two upper levels. You will enjoy a sunny and bright reading level, and also a media area. It's just a beautiful home, wrap front porch. Gorgeous landscaping. The Pink Lady has been loved, updated and turn key condition!

Type:
Single Family
Sq.Ft.:
2,660
Status:
Active
Beds:
4
Lot size:
0.11 Acres
Year built:
1920
Baths:
3.00
MLS#:
MDKE107896
Subdivision:
Historic District

ADDITIONAL INFORMATION

Charm and character abound in this home, renovated and updated inside and out in 2008. Nice layout on main level includes gracious kitchen with wet bar, pantry, powder room, wood stove fireplace insert in family room, open dining room and separate craft room. Second floor offers nice master bedroom with private tiled shower and soaking tub plus two additional bedrooms, ceramic tile bath and bedroom level laundry. Third floor includes an additional finished 500 sq ft with 2 rooms, one of which could be 4th bedroom. Hardwood floors throughout. Privacy fenced back yard with deck overlooks space that will not be developed and includes a cute and functional shed. Off street parking included. Property is ideally located on a desirable street one block from college and an easy walk to downtown. Currently rented but available immediately subject to lease, or after June 1st. Agent related to owners.

Type:
Single Family
Sq.Ft.:
5,080
Status:
Active
Beds:
7
Lot size:
0.45 Acres
Year built:
1903
Baths:
5.00
MLS#:
MDKE107864
Subdivision:
Chestertown

ADDITIONAL INFORMATION

Charming Victorian situated on large level lot. Offers high ceilings, dramatic staircase, lovely arches, original floors, commercial grade kitchen. Large barn on the property and a separate one bedroom carriage house that is currently rented for $995 per month. With obtaining a permit, could be a B and B.

Type:
Single Family
Sq.Ft.:
1,567
Status:
Active
Beds:
4
Lot size:
0.36 Acres
Year built:
1968
Baths:
2.00
MLS#:
MDKE107890
Subdivision:
Quaker Estates

ADDITIONAL INFORMATION

Type:
Single Family
Sq.Ft.:
756
Status:
Active
Beds:
1
Lot size:
0.18 Acres
Year built:
1900
Baths:
1.00
MLS#:
MDKE107882
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

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!

Type:
Single Family
Sq.Ft.:
1,472
Status:
Active
Beds:
2
Lot size:
0.72 Acres
Year built:
1983
Baths:
3.00
MLS#:
MDKE107874
Subdivision:
Mile Tree Village

ADDITIONAL INFORMATION

Mile Tree Village Cape Cod home with three fireplaces, a traditional floor plan, living room, family room, screened porch, backs to woods. Home needs some updating and TLC, but it's a wonderful neighborhood. There are two bedrooms, 2 full baths, 1/2 bath, wood floors, loads of built ins both upstairs and in the family room. Within minutes to historic downtown Chestertown, but a peaceful and quiet setting. Upstairs has central air, public water and sewer. Basement has a bathroom that has been started, a fireplace, it's unfinished for the most part.

Type:
Single Family
Sq.Ft.:
2,571
Status:
Active
Beds:
4
Lot size:
0.38 Acres
Year built:
2000
Baths:
3.00
MLS#:
MDKE107870
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

An extremely well built and maintained custom home in the water oriented community of Chesapeake Landing. Over 2,500 sq ft featuring hardwood floors throughout, 1st floor master with a full bath, exposed axed hewn beams and gas fireplace in the living room, attached heated 2 car garage and 4 bedrooms all with walk in closets! Outside there is a fenced yard, wrap around porch and large garden shed on a concrete pad. Other features include a central vac system, efficient casement windows, upstairs laundry, and accent lighting. Located on a partially wooded private lot this home is close to local marinas, public landings and restaurants.

Type:
Single Family
Sq.Ft.:
816
Status:
Active
Beds:
2
Lot size:
0.5 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE107850
Subdivision:
N/A

ADDITIONAL INFORMATION

Rehab potential value is in the land only

Type:
Single Family
Sq.Ft.:
1,288
Status:
Active
Beds:
2
Lot size:
0.46 Acres
Year built:
2005
Baths:
2.00
MLS#:
MDKE107836
Subdivision:
Tolchester

ADDITIONAL INFORMATION

One level living at it's best. Split floor plan with two bedrooms, 2 baths, loads of storage, a great kitchen, open floor plan concept, new furnace in 2018. There is a screened porch, a detached 20' x 40' garage workshop with a wood stove that conveys to the happy new owner! This home is in move in condition. Check out the photos! Join the optional HOA for $55.00/annually and get access to the Chesapeake Bay, a nice community center. Near a full service public marina as well! With the lots included on the deed you have one private acre that will stay that way. Call for more detail.

Type:
Single Family
Sq.Ft.:
1,232
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
2018
Baths:
2.00
MLS#:
MDKE107824
Subdivision:
Quaker Estates

ADDITIONAL INFORMATION

GREAT NEW BUILD. HOME IS COMPLETE. OPEN DESIGN W/ LARGE KIT & LIVING AREA. UPGRADED FLOORING & STAINLESS KITCHEN PACKAGE W/ KITCHEN ISLAND. LED LIGHTING PACKAGE SEP. LAUNDRY/UTILITY ROOM. SPLIT BEDROOM DESIGN. EXTERIOR COLOR MAY VARY. END OF YEAR DELIVERY. BUYER PAYS ALL REC & TRANSFER. MHBR #3717.

Type:
Single Family
Sq.Ft.:
960
Status:
Active
Beds:
3
Lot size:
0.86 Acres
Year built:
1970
Baths:
2.00
MLS#:
MDKE103818
Subdivision:
Georgetown

ADDITIONAL INFORMATION

This house is basically brand new! It has been completely renovated from top to bottom. All new stainless steel appliances, hot water heater, central air/heat, large 16x16 back deck, metal roof, siding, flooring, plumbing, you name it! On almost an acre of land with public water/sewer and a 16x12 shed that has electric. The house is located on a private and quiet street away from all the hustle and bustle of town but still a short drive away.

Type:
Single Family
Sq.Ft.:
4,214
Status:
Active
Beds:
4
Lot size:
168.77 Acres
Year built:
2002
Baths:
3.00
MLS#:
MDKE104742
Subdivision:
Pentridge Farms

ADDITIONAL INFORMATION

Rarely do you find a true contemporary residence in this traditional area in Kent County on Maryland's Eastern Shore. This architecturally designed house is surrounded by 168 private acres of open fields, virgin woods & ponds. The 3000+ square footage includes soaring beamed ceilings, open kitchen/living area, wood floors, soap stone counters, gourmet kitchen. An exotic European style "woodstove" (far from your ordinary woodstove - see photos) dominates the outstanding design. Multiple French door & casement windows flow to a 700 sq. ft. deck & 1700 slate A& brick patio. A handsome pergola completes the design of the groundsAn exciting contemporary post & beam guest house shares the acreage and is located a private distance away. The open interior design, exposed beamed ceilings & decking compliments the main house design. Pastoral views and farms abound.

Type:
Single Family
Sq.Ft.:
1,400
Status:
Active
Beds:
3
Lot size:
1.64 Acres
Year built:
1972
Baths:
2.00
MLS#:
MDKE102324
Subdivision:
None

ADDITIONAL INFORMATION

Looking for a move in ready home? This is it! Updated kitchen with granite counters and under cabinet lighting. Both baths updated. Wood floors have been refinished. Heat pump installed 5 years ago. New doors and some new windows. Large deck looks over back yard with lots of room for a garden.

Type:
Single Family
Sq.Ft.:
1,000
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1963
Baths:
1.00
MLS#:
MDKE102614
Subdivision:
Quaker Estates

ADDITIONAL INFORMATION

This ranch home is located about five to six minutes outside of Chestertown. Home has new carpet, some new paint. Affordably priced with three bedrooms, 1 bath, and a detached storage shed. Don't be mortgage poor. With a little elbow grease and vision, this can be one cute home!

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Joe Quinn, Maryland License 6089, Xome Inc., License 6089, Joe.Quinn@Xome.com, 844-400-XOME (9663), 300 East Lombard Street, Suite 840, Baltimore, MD 21202
Joe Quinn, D.C. License PB98375891, Xome Inc., License CO98372739, Joe.Quinn@Xome.com, 844-400- 9663, 300 E. Lombard St., Suite 840, Baltimore, MD 21202
Thomas H. O’Leary, PA License #RM423918, Xome Inc., PA License #RB067821, ThomasH.OLeary@Xome.com, 844-400-XOME (9663) 3200 Park Center Drive, 15th Floor, Costa Mesa, CA 92626
Thomas H. O'Leary, NJ License # 1754747, Xome Inc. NJ License # 1861285, ThomasH.OLeary@Xome.com, 844-400-XOME (9663), 3200 Park Center Drive, 15th Floor, Costa Mesa, CA 92626

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

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