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

Chestertown MD Real Estate & Homes for Sale

108 Properties Found

The median home value in Chestertown, MD is $220,000. 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 $220,000. 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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Beds:
3
Baths:
1.00
Sq.Ft.:
952
Status:
NEW LISTING
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.:
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.

Open House:

Saturday, 11/17 10:30-12:30PM

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
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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
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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.

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
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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
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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:
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
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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:
3
Baths:
1.00
Sq.Ft.:
960
Status:
Active
MLS#:
1009949688
Type:
Single Family
Subdivision:
Washington Park
Lot size:
0.52 Acres
Year built:
1965
Courtesy: Keller Williams Select Realtors
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Remodeled rancher in Chestertown. New, eat-in kitchen with granite counters, stainless appliances. Hardwood floors. Tile bath. New carpet. Recessed lighting in living room and kitchen. New HVAC, New wiring,plumbing, Large lot. Great home for the price. Just move in.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,404
Status:
Active
MLS#:
1009958372
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.47 Acres
Year built:
2005
Courtesy: The Hogans Agency Inc.
View additional info

Dutch colonial in water privileged community with docks and boat ramp close to marina. Nice size rooms, first floor bedroom, deck off Dining Room. Large lot. Home is in excellent condition - like new.

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:
3
Baths:
2.00
Sq.Ft.:
1,500
Status:
Active
MLS#:
1009933688
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1989
Courtesy: Century 21 Downtown
View additional info

Deeply Discounted Foreclosure Opportunity in Chester Harbor. Property was previously renovated/updated. Large, clean rancher w/ addition in need of TLC. Sold Subject to ground rent if existing seller will not redeem. Assignment of a bank foreclosure, special papers needed for offer. Contact LA. Sold as-is cash or hard money . Conventional w/ 20% down possible. NO FHA . Seller does not guarantee accuracy in this listing, buyer/agent to verify.

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
Beds:
3
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

OPEN SAT, 27TH, 12-2 PM! AMAZING CUSTOM-BUILT ESTATE sited on almost 14 acres w/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.

Beds:
3
Baths:
2.00
Sq.Ft.:
852
Status:
Active
MLS#:
1009223586
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1987
Courtesy: Wyble Enterprises
View additional info

Raised rancher with 3-bedrooms, 1 1/2 baths, partially-finished basement, deck, 1-car garage, central heat and AC. om a water-privileged community 3 miles from Chestertown. Being Sold AS IS with inspections. Clothes dryer, water softener and microwave are not in working order. Possible investment opportunity.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,364
Status:
Active
MLS#:
1008349662
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.26 Acres
Year built:
2009
Courtesy: Real Estate Professionals, Inc.
View additional info

Stately Colonial Style Home now Available in the Coventry Farms Neighborhood of Chestertown. This Home Features 4 Bedrooms and 2.5 Baths, a Gourmet Kitchen with Breakfast Nook and Separate Dining Room, and Finished Basement with Access to Spacious Back Yard. Seller Financing May Be Available

Beds:
7
Baths:
9.00
Sq.Ft.:
9,651
Status:
Active
MLS#:
1008176730
Type:
Single Family
Subdivision:
Quaker Neck
Lot size:
164.13 Acres
Year built:
1965
Courtesy: Cross Street Realtors LLC
View additional info

Bachelors Hope Farm, available for the first time in 50+ years, is a once-in-a-lifetime waterfront & hunting farm. 9,600 square foot, 7 bed Main Home is situated within feet of the Chester River. 420 foot dock has 8 feet MLW, water & electric, with railway. 3,000+ feet of River frontage with 1,400+ foot revetment. 164+ acres: 96 tillable, 43 wooded & 3 ponds. 4 bed Farm Home & barn. Exquisite & prestigious Quaker Neck locale.

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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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