Chestertown MD Real Estate & Homes for Sale

94 Properties Found

The median home value in Chestertown, MD is $215,500. 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 $215,500. 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.


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1–25 of 94 properties displayed
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Beds:
3
Baths:
2.00
Sq.Ft.:
1,144
Status:
Active
MLS#:
MDQA116350
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.38 Acres
Year built:
1992
Courtesy: Champion Realty, Inc.
View additional info

Beautiful 3 BR, 2BA Rancher situated on a corner lot with mature shade trees. Short walk to Rosin Creek and public boat launch. Corian counters, separate laundry room off the kitchen. Nice 10x15 screened-in porch.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,582
Status:
Active
MLS#:
MDKE101958
Type:
Single Family
Subdivision:
Chestertown
Lot size:
166 Acres
Year built:
1920
Courtesy: Select Land & Homes, LLC
View additional info
Beds:
3
Baths:
2.00
Sq.Ft.:
960
Status:
Active
MLS#:
MDKE103818
Type:
Single Family
Subdivision:
Georgetown
Lot size:
0.86 Acres
Year built:
1970
Courtesy: CR Realty
View additional info

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.

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

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
MDKE102324
Type:
Single Family
Subdivision:
None
Lot size:
1.64 Acres
Year built:
1972
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,002
Status:
Active
MLS#:
MDKE102890
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.06 Acres
Year built:
1920
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This property is now under auction terms. The property is subject to a 5% buyer~s premium pursuant to the Auction Terms & Conditions (minimums may apply). All auction assets will be sold subject to seller approval.This lovely historic home has a lot of potential & appeal, which includes beautiful hard wood floors, silestone counter tops and cherry cabinets in the kitchen. The master suite has a huge walk-in closet with built-ins plus the master bath has a claw foot tub and separate shower. Close to downtown for dining and shopping. Call today to make an appointment to see this great property.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,000
Status:
Active
MLS#:
MDKE102614
Type:
Single Family
Subdivision:
Quaker Estates
Lot size:
0.34 Acres
Year built:
1963
Courtesy: Doug Ashley Realtors, LLC
View additional info

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!

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE100810
Type:
Townhouse
Subdivision:
Chester River Landing
Lot size:
0.04 Acres
Year built:
2007
Courtesy: Cross Street Realtors LLC
View additional info

Experience true luxury in this magnificent Chestertown waterfront residence. Gleeming hardwood floors, high ceilings and well-appointed architectural detail accent the main level open floor plan outfitted with a great room that includes a grand foyer, formal seating area, and living room, gourmet kitchen, and dining space. The wrap-around porch affords more room for entertaining while the surround sound system adds to the acoustic ambiance. In addition to unobstructed expansive views of the Chester River, the large and ample windows provide an abundance of natural light that tastefully compliments the sophisticated paint scheme enjoyed throughout the home. Take the elevator or the stairs and retreat to the master bedroom suite where you can enjoy a bubble bath in the Jacuzzi tub while watching your favorite program or a nightcap in front of the fireplace or out on the private balcony. * Guests can retreat to the en-suite just down the hall. The third level, which can also be accessed by the elevator, features two bedrooms and a jack & jill bathroom. These rooms currently serve as an art studio and office. * Located in Chester River Landing, one of Kent County's most coveted waterfront communities, homeowners enjoy elite privileges with the peace of mind of having low maintenance, which certainly compliments an enthusiastic and active lifestyle. * 114 Little Harbor Way is one of the few with a deeded boat slip offering 4' mlw, detached garage and private off-street brick parking spaces for 2 vehicles. * NOTICE TO BUYERS: Total Finished Square Feet - 3,406, Property Taxes - $8,051.40 + Town Tax - $2,982.00.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,582
Status:
Active
MLS#:
MDKE102294
Type:
Single Family
Subdivision:
None
Lot size:
166.65 Acres
Year built:
1920
Courtesy: Select Land & Homes, LLC
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166 +/- total acre farm with 66 tillable acres, 75 wooded acres and the remaining in home site, barns, and active gravel pit. The farm offers excellent deer, turkey and waterfowl hunting and has several potential pond sites. Located near Remington Farms and approximately 10 minutes between Rock Hall and Chestertown, this farm is priced to sell at $5,391 an acre! Property lines in aerial photo are approximate.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,136
Status:
Active
MLS#:
MDKE100150
Type:
Townhouse
Subdivision:
None Available
Lot size:
0.07 Acres
Year built:
1992
Courtesy: Sommers Enterprises, Inc.
View additional info

Live in town as personal residence or continue renting to current or future tenant(s) as investment. Located well for access to all Town conveniences. Large level fully fenced yard that wraps two sides of house.

Beds:
3
Baths:
1.00
Sq.Ft.:
952
Status:
Active
MLS#:
MDKE100034
Type:
Single Family
Subdivision:
None-Available
Lot size:
0.5 Acres
Year built:
1900
Courtesy: The Hogans Agency Inc.
View additional info

House that needs complete renovation on half acre with public water and sewer hooked up. Sold "As Is".

Beds:
5
Baths:
3.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
1009979876
Type:
Single Family
Subdivision:
Crestview
Lot size:
0.56 Acres
Year built:
1998
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Exhale and enjoy a one level living lifestyle near Downtown Chestertown. With 5 bedrooms total, this home offers all pocket doors and an in-law suite with a handicap accessible master bathroom. The other side of the home sits a master bedroom w/ on-suite and 3 other bedrooms. Freshly painted, move in ready with an updated kitchen with newer stainless steel appliances, granite countertop and a large pantry. The oversized garage allows for small boat storage, ATV's or other fun toys. Bring the outdoors in with two sliders, extending the family room onto the screened porch and back yard.

Beds:
5
Baths:
6.00
Sq.Ft.:
5,190
Status:
Active
MLS#:
MDKE100018
Type:
Single Family
Subdivision:
None
Lot size:
76.07 Acres
Year built:
1800
Courtesy: Brandywine Fine Properties Sot
View additional info

A quintessential 76-acre Eastern Shore waterfront estate built in 1781 & restored in the 90's. Providence Plantation defines Country Elegance with a fabulous 1st flr MBR suite, a new 3BR tenant house, dock with lift & an in-ground pool. A 3rd home may be built to create a family compound. Enjoy the peace and serenity of Eastern Shore outdoor Life. Agent/Owner.

Beds:
6
Baths:
6.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE100016
Type:
Single Family
Subdivision:
None
Lot size:
76.07 Acres
Year built:
1782
Courtesy: Brandywine Fine Properties
View additional info

A quintessential 76-acre Eastern Shore waterfront estate built in 1781 & restored in the 90's. Providence Plantation defines Country Elegance with a fabulous 1st floor master bedroom suite, a new 3 BR Tenant House, dock with lift and an in-ground pool. A 3rd home may be built to create a family compound. Enjoy the peace and serenity of the Eastern Shore outdoor life. Owner is Licensed Real Estate Agent.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,867
Status:
Active
MLS#:
1009970936
Type:
Single Family
Subdivision:
Kingstowne Manor
Lot size:
0.46 Acres
Year built:
2004
Courtesy: Cross Street Realtors, LLC
View additional info

Move-in ready home in Queen Anne's County, but just a few minutes from Downtown Chestertown! Offering new carpets, paint and landscaping. Desirable split bedroom, single level living floor plan. Large Master suite offers walk in closet and great Master bath with tiled floors, double vanity, separate shower and corner soaking tub! Two additional bedrooms share a full bath with tiled floors. Large kitchen/breakfast area with stone tile floors and wood cabinets opens to screened porch. Open family room with propane fireplace for chilly Fall nights. Separate formal dining room or office space. Oversize 2-car garage and a fully fenced rear yard round out the total package.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,548
Status:
Active
MLS#:
MDKE100000
Type:
Condo/Townhouse
Subdivision:
None Available
Lot size:
0.03 Acres
Year built:
2008
Courtesy: Doug Ashley Realtors, LLC
View additional info

Pretty townhome in a four unit building. Very clean, looks brand new. Stainless appliances, a full dry basement with inside access. Sprinkler system, wood floors, community pond with a soothing fountain feature, gazebo. No maintenance. HOA is 150/quarterly. Gorgeous light with loads of windows. Granite countertops, open kitchen/living room with a breakfast bar.

Open House:

Saturday, 1/5 11:00-2:00PM

Beds:
4
Baths:
3.00
Sq.Ft.:
800
Status:
Active
MLS#:
1010004222
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.69 Acres
Year built:
2004
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This home shows like a model! Wonderful floor plan makes it a delight and great for entertaining! Gleaming Hardwood floors, vaulted ceilings, upgraded cabinetry throughout. Gourmet kitchen with gas double oven and stainless steel appliances. Great room has lovely views of rear yard and woods and a nice balcony off it. Current owner finished basement with Family Room and bar, a fabulous full bathroom and a bonus room that is currently used as a spare bedroom. Well maintained home ready for your quick settlement!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,500
Status:
Active
MLS#:
1010003642
Type:
Single Family
Subdivision:
Waterfield
Lot size:
6 Acres
Year built:
1989
Courtesy: Select Land & Homes, LLC
View additional info

A country treasure located just outside of Chestertown on 6 open acres with views of 4 acre waterfowl pond. Spacious home with lots of desirable features. Room for animals, hobby crops, a pool, or whatever you want. Recent roof replacement and brand new well. Metal shop building with tractor shed attached. The possibilities are endless!

Open House:

Saturday, 1/5 11:00-1:00PM

Beds:
5
Baths:
4.00
Sq.Ft.:
5,563
Status:
Active
MLS#:
1009997800
Type:
Single Family
Subdivision:
21 Private Acres
Lot size:
21.06 Acres
Year built:
2005
Courtesy: Chaney Homes, LLC
View additional info

Over 21 Acres Ready for your Horses & Existing Vineyard- Possible B&B! 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!

Open House:

Saturday, 1/5 11:00-1:00PM

Beds:
5
Baths:
4.00
Sq.Ft.:
5,563
Status:
Active
MLS#:
1002071386
Type:
Single Family
Subdivision:
21 Private Acres
Lot size:
21.06 Acres
Year built:
2005
Courtesy: Chaney Homes, LLC
View additional info
Beds:
4
Baths:
3.00
Sq.Ft.:
2,114
Status:
Active
MLS#:
1009954076
Type:
Single Family
Subdivision:
Downtown Chestertown
Lot size:
0.1 Acres
Year built:
1884
Courtesy: Cross Street Realtors LLC
View additional info

Iconic Mill Street home, this "Folk Victorian" has been lovingly maintained & thoughtfully upgraded while maintaining the historic features: refinished Heart Pine flooring throughout, crown moulding, chair rails, built-in shelving, & an extra-long claw foot soaking tub . Upgrades include high-velocity HVAC, blown-in insulation (walls, attic, & cellar), granite counters & new cabinetry in the kitchen, tiled bathrooms, dressing room off the Master bedroom with a walk-in closet, & encapsulated cellar. The backyard oasis is private, quiet, & low-maintenance; seasonal trees & plants bloom three seasons of the year. The garden shed & shop is tucked away, but offers great storage & work space. Situated in the heart of Downtown Chestertown, take a peek at this home soon!

Beds:
2
Baths:
1.00
Sq.Ft.:
768
Status:
Active
MLS#:
1009957738
Type:
Single Family
Subdivision:
Calvert Homes
Lot size:
0.09 Acres
Year built:
1949
Courtesy: Cross Street Realtors LLC
View additional info

Affordable home beautifully and thoroughly renovated in 2015 with new roof, kitchen, windows, bathroom, range, dishwasher, washer & dryer. You could own this home for LESS than $950/mo and this INCLUDES taxes & insurance. This is a must see to appreciate everything this house has to offer including the front porch, rear deck and completely fenced yard. TENANT OCCUPIED so please allow 24 hour notice. Investor Buyers - Tenant would like to stay if possible!

Beds:
5
Baths:
6.00
Sq.Ft.:
10,870
Status:
Active
MLS#:
1009942958
Type:
Single Family
Subdivision:
Chestertown
Lot size:
300 Acres
Year built:
1990
Courtesy: Benson & Mangold, LLC
View additional info

300+/- acre waterfront estate with exceptional amenities. Main house with 7,500+/- sq ft, with a retreat feel and open floor plan. Indoor and outdoor pools, high elevation and expansive southern and western views down coveted West Fork Langford Creek. Boat house with 7'+.- MLW, tenant house, historic farm house, antique covered bridge, large barn, waterfowl ponds and 1.5+/- miles of shoreline.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,128
Status:
Active
MLS#:
1008575416
Type:
Single Family
Subdivision:
None Available
Lot size:
10 Acres
Year built:
2005
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore Georgian style home is situated on a serene, rural 10-acres, yet is conveniently located just 2 miles from the colonial town of Chestertown. Designed by the architect, Andrea Lombardini, and built in 2005, the thoughtfully designed interior lends an airy elegance harmoniously linking the sunlit living areas, including the first floor master suite. Taking full advantage of the pastoral views, the home showcases the finest details including random width wood floors, built-ins, high ceilings and a terrace overlooking the naturally beautiful setting. Chestertown offers a river walk, brick lined streets with 18th century homes, galleries, live theater and cafes. It enjoys a vibrant arts community, outdoor educational programs and is home to Washington College. Located about 90-minutes from Washington and Philadelphia.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,168
Status:
Active
MLS#:
1009918978
Type:
Single Family
Subdivision:
Fairlee
Lot size:
2 Acres
Year built:
1948
Courtesy: Champion Realty, Inc.
View additional info
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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 participates, and is provided by BRIGHT through a licensing agreement. 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. Copyright BRIGHT, All Rights Reserved

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The data relating to real estate for sale on this website appears in part through the TReND Broker Reciprocity (SM) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Schneider Real Estate, NJ participates, and is provided by TReND through a licensing agreement.

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