Chestertown, MD Homes For Sale | Real Living Reserve Realtors | Real Living Real Estate

Chestertown MD Real Estate & Homes for Sale

80 Properties Found

The median home value in Chestertown, MD is $236,000. 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 Chestertown, MD is $236,000. 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 80 properties displayed
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Beds:
4
Baths:
2.00
Sq.Ft.:
1,567
Status:
NEW LISTING
MLS#:
MDKE107890
Type:
Single Family
Subdivision:
Quaker Estates
Lot size:
0.36 Acres
Year built:
1968
Courtesy: Champion Realty, Inc.
View additional info
Beds:
1
Baths:
1.00
Sq.Ft.:
756
Status:
Active
MLS#:
MDKE107882
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.18 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

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!

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

Beds:
2
Baths:
2.00
Sq.Ft.:
816
Status:
Active
MLS#:
MDKE107850
Type:
Single Family
Subdivision:
N/A
Lot size:
0.5 Acres
Year built:
1900
Courtesy: Harlan C. Williams Co.
View additional info

Rehab potential value is in the land only

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE107824
Type:
Single Family
Subdivision:
Quaker Estates
Lot size:
0.34 Acres
Year built:
2018
Courtesy: Rosendale Realty
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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. PICS ARE OF PREVIOUS HOME

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
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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
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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
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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:
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
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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:
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.
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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:
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
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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.:
5,250
Status:
Active
MLS#:
MDKE100016
Type:
Single Family
Subdivision:
None
Lot size:
76.07 Acres
Year built:
1781
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.:
2,040
Status:
Active
MLS#:
1010003886
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.25 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
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A true diamond in the rough. Everyone loves a swing on a front porch, it always brings such a welcoming feel and looks so inviting to take a few minutes to relax on. Then into the open foyer with a beautiful stair case that leads to the 3rd floor. Pocket door from parlor to dining area is in wonderful condition. Original trim and molding that you will want to keep for sure. Hardwood flooring is in good condition, light refinish would do the trick . Original doors that are in gorgeous condition with original hardware. This home is ready for renovation with so much good to offer that gives this home so much of its character. Selling As IS.

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.:
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!

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!

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:
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:
5
Baths:
6.00
Sq.Ft.:
10,870
Status:
Active
MLS#:
1000346718
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:
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
Beds:
2
Baths:
1.00
Sq.Ft.:
1,125
Status:
Active
MLS#:
1008362670
Type:
Single Family
Subdivision:
Beautiful Quaker Neck Peninsula
Lot size:
0.47 Acres
Year built:
1949
Courtesy: Doug Ashley Realtors, LLC
View additional info

Bring your water toys and enjoy this cute cottage located approximately 1.5 miles from Quaker Neck Landing! Family/dining area combination has wood floors, a wood burning stove and beamed wood ceiling. First floor bedroom has walk-in closet and hookup for stack-able washer/dryer. Upstairs has a 2nd bedroom and currently used as "the Bunk Room" . The grounds have been well landscaped and there is even an outdoor shower! Use as a retreat, primary home, hunting cabin/cottage, etc. Not too far from Historic downtown Chestertown!!

Beds:
5
Baths:
4.00
Sq.Ft.:
5,367
Status:
Active
MLS#:
1009688038
Type:
Single Family
Subdivision:
None
Lot size:
13.17 Acres
Year built:
2006
Courtesy: Champion Realty, Inc.
View additional info

AMAZING CUSTOM-BUILT ESTATE sited on almost 14 acres w/stream & Every luxury & upgrade + 2500 sf basement. First floor master, 4 addtnl Brs, Phenomenal kitchen includes 3 ovens, double dishwasher, granite counters, custom Amish lighted, glass cab., custom tile floors, double sinks + veg sink, conv. micro, table space, serving counter, desk area. STUNNING wall of glass & two-story brick FIREPLACE in open family room w/balcony overlook. HUGE screened porch w/vaulted ceiling & brick floor. Amazing brick front porch w/entertainment area to capture every country view! IT'S WORTH A LOOK; YOU'LL FALL IN LOVE!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
1008616880
Type:
Manufactured Home
Subdivision:
Militota
Lot size:
2 Acres
Year built:
1972
Courtesy: Doug Ashley Realtors, LLC
View additional info

Double-wide home on a great 2 acre corner lot! House is being sold "AS IS" but with a little work this could be a great home. Has a relatively new metal roof.

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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

Chestertown MD Real Estate Listings Provided By:

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1768 Business Center Drive Ste. 320
Reston, VA 20190
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