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

Chestertown MD Real Estate & Homes for Sale

87 Properties Found

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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Open House:

Saturday, 4/13 1:00-3:00PM

Beds:
2
Baths:
1.00
Sq.Ft.:
1,008
Status:
NEW LISTING
MLS#:
MDKE114110
Type:
Single Family
Subdivision:
Chestertown / Downtown
Lot size:
0.1 Acres
Year built:
1900
Courtesy: RE/MAX Executive
View additional info

ADORABLE and AFFORDABLE! This is town living at it's finest. Walk to local restaurants, shops,Chester River, enjoy festivals and tranquility. Escape the hustle and bustle and enjoy everything historic Chestertown has to offer. This cozy home boasts hardwood floors and a LARGE eat in kitchen. This has been used an income producing Air BnB and used as a great escape from theWestern Shore.

Beds:
6
Baths:
2.00
Sq.Ft.:
2,530
Status:
NEW LISTING
MLS#:
MDKE113968
Type:
Single Family
Subdivision:
Downtown Chestertown
Lot size:
0.1 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
View additional info

Historic Downtown beauty with numerous recent upgrades has a potential FIRST FLOOR MASTER, sought after off street/driveway parking, within ONE block of the new & improved Chestertown Marina, and in the HEART of everything Chestertown has to offer. Totaling four bedrooms - with the possibility for two more, two bathrooms, gorgeous hardwood floors, huge kitchen with stainless steel appliances, the perfect front porch, and a cozy, low maintenance backyard full of raised bed gardens and entertaining space! What more can you ask for in a Downtown home? A must see.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,745
Status:
NEW LISTING
MLS#:
MDKE114020
Type:
Single Family
Subdivision:
Chestertown
Lot size:
2.34 Acres
Year built:
1986
Courtesy: Gunther-McClary Real Estate
View additional info

Very private 3 bedroom home in park like settling located on the upper reaches of Morgnec Creek with water access to the Chester River. Bring your boat to explore all nature has to offer, commune with eagles, herons, terns, deer, turtles and other wildlife on this lovely creek. This home offers waterfront views from nearly every room, numerous upgrades over the past few years, perfect for a weekend get away or a fulltime resident. Just minutes from historic Chestertown and with the new Middletown by-pass less than 1 hour from Wilmington and points north.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE114042
Type:
Single Family
Subdivision:
Chesapeake Landiing
Lot size:
0.36 Acres
Year built:
1992
Courtesy: Doug Ashley Realtors, LLC
View additional info

Well kept home with hardwood floors throughout, a mud room, a three car attached garage with resin flooring, open floor plan, nice light, corner lot, three bedrooms, and 2 baths with ceramic tile and the master bath has a shower. Located in Chesapeake Landing, if you join the HOA you will have access to the water. Upgraded septic system is four years old (BAT system) new water conditioning system (owned) Stainless steel refrigerator and stove.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,437
Status:
Active
MLS#:
MDKE114044
Type:
Single Family
Subdivision:
Country
Lot size:
2.01 Acres
Year built:
1964
Courtesy: Doug Ashley Realtors, LLC
View additional info

Solid brick home with an additional one bedroom apartment, rents for 600.00/month. This could be an office. Lot consists of 2.01 acres, plenty of room to add a pole building or a detached garage. Main home has wood floors, a wood stove, a enclosed porch on the side, three bedrooms and two baths. Great location, about 5 miles outside of Chestertown.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,186
Status:
Active
MLS#:
MDKE114080
Type:
Single Family
Subdivision:
Fannell's Meadow
Lot size:
2.22 Acres
Year built:
1991
Courtesy: Doug Ashley Realtors, LLC
View additional info

Cape Cod designed, wood sided home with a first floor master suite, family room with fireplace, family area with skylights on the 2nd level, could be a great artist's studio. There are four bedrooms all total and 2.5 baths. Nice rear composite deck, patio and a 23 x 15 shed. The three car garage with one bay is used as a workshop, which is heated and cooled. Conditioned crawl space.

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE114060
Type:
Single Family
Subdivision:
Quaker Estates
Lot size:
0.39 Acres
Courtesy: Rosendale Realty
View additional info

ANOTHER AWESOME NEW HOME. 45 DAYS FROM COMPLETION. HOME WILL FEATURE OPEN DESIGN WITH LARGE KITCHEN/DINING/LIVING AREA IN THE CENTER AND BEDROOMS SPLIT TO BOTH SIDES OF THE HOME. LAMINATE VINYL FLOORING FOR DURABLE, EASY MAINTENANCE. BUYER STILL HAS TIME TO SELECT BEDROOM CARPET COLORS. CHESTNUT COLORED CABINETS IN KITCHEN WITH CENTER ISLAND AND FULL KITCHEN APPLIANCE PACKAGE. SEPARATE LAUNDRY ROOM AND 2 FULL BATHROOMS ROUND OUT THE LIST OF GREAT FEATURES. ALL ON LOT BACKING TO WOODS. FINISHED HOME PICS ARE OF A PREVIOUS MODEL: OPTIONS AND COLORS WILL VARY. BUYER PAYS ALL REC AND TRANSFER CHARGES MHBR# 3717

Beds:
3
Baths:
3.00
Sq.Ft.:
2,202
Status:
Active
MLS#:
MDKE114014
Type:
Single Family
Subdivision:
Historic District Chestertown
Lot size:
0.06 Acres
Year built:
1760
Courtesy: Doug Ashley Realtors, LLC
View additional info

This gorgeous home "Banning House" is updated beautifully in the historic district, a couple of blocks from the Chester River. Wood floors are incredible, there is a brick floored den/family room overlooking a private courtyard. It's currently a successful and popular VRBO but makes for a fantastic single family home. Updated kitchen with amazing detail to the upgrades. Stainless steel appliances, new HVAC and loads of charm. Steps to the Chester River, restaurants and so much more.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,352
Status:
Active
MLS#:
MDKE114008
Type:
Single Family
Subdivision:
Great Oak -Fairlee Creek Estates
Lot size:
0.92 Acres
Year built:
1987
Courtesy: Doug Ashley Realtors, LLC
View additional info

Wonderful community of Great Oak. There is a non mandatory HOA but consider joining for access to all the amenities. It's only $60.00 per year! Pool/marina/private beach is awesome. There is also a 9 hole golf course. Home is roomy and in a private setting, just 15 minutes from Historic Chestertown. First floor master, two car garage, den/living room, dining room. Rooms are nice sizes. Check out this nice home.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,923
Status:
Active
MLS#:
MDKE114002
Type:
Single Family
Subdivision:
Chestertown / Downtown
Lot size:
0.12 Acres
Year built:
1900
Courtesy: RE/MAX Executive
View additional info

This home will AMAZE you! Open floor plan with gorgeous built ins. Kitchen renovation with large kitchen island, granite counters, ss appliances, with a view that you won't find any where else in town! The in-ground pool makes this house the ONE! Get out of the hustle and bustle, come home and sit back and relax and let your worries go away. OVERSIZED bedrooms with OVERSIZED bathrooms!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,960
Status:
Active
MLS#:
MDKE114000
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.24 Acres
Year built:
1903
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

A Classic American Victorian, wrap around porch with balustrade. Many new appointments, including a new kitchen and new baths, while retaining the Victorian signatures of high ceilings, spacious rooms, fine wood floors, detailed wood trim, long windows, arched walls and graceful staircase. Rear and side gardens, 2 car detached garage with wine room and potting shed at the end of this Water St. driveway.

Beds:
2
Baths:
1.00
Sq.Ft.:
800
Status:
Active
MLS#:
MDKE113992
Type:
Single Family
Subdivision:
Tolchester
Lot size:
0.54 Acres
Year built:
1943
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Location! Location! Location! Cozy 1940's Bay front cottage on .54 acre lot with spacious screened porch & detached 2 bay garage offers panoramic year round views of the Chesapeake Bay. distant shores & passing ships. Fix up existing cottage or build new. Flood insurance not required. Oversized lot grandfathered for home site. Public sewer. Rare find!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,023
Status:
Active
MLS#:
MDQA136926
Type:
Single Family
Subdivision:
Pear Tree Point & Roysto
Lot size:
0.41 Acres
Courtesy: The Hogans Agency Inc.
View additional info

Unique 2,208 square foot home to be built in the water privileged community of Pear Tree Point. 3 BR, 2.5 baths, granite counter tops, wood, carpet and tile floors. This home provides a very functional split-floor plan, an open kitchen layout with plenty of counter space for a growing family and a bonus room over the garage. The plan features an expansive master bedroom / bath with a trayed ceiling and plenty of storage space in his and her walk-in closets. The large great room also includes a trayed ceiling. Front and rear covered porches make the evenings enjoyable. This home is a great value with a wide variety of innovative features.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,520
Status:
Active
MLS#:
MDKE113950
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.17 Acres
Year built:
1900
Courtesy: Select Land & Homes, LLC
View additional info

Investor alert! Two buildings on one property near Downtown Chestertown and Washington College. Property being sold As-Is.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,824
Status:
Active
MLS#:
MDKE113958
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.17 Acres
Year built:
1900
Courtesy: Select Land & Homes, LLC
View additional info

Investor opportunity near Downtown Chestertown and Washington College. Previously set up as four, 1 bedroom apartments. Property sold As-Is.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,024
Status:
Active
MLS#:
MDKE113904
Type:
Single Family
Subdivision:
Fannell's Meadow
Lot size:
1.98 Acres
Year built:
1992
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Easy living at its finest!! This custom built and meticulously maintained home has all the amenities one could ask for. They include ample living space with storage, in-law suite with separate entrance, grand family room with brick fireplace, a stylish & welcoming kitchen that lends itself not only to the cooking enthusiast but also offers a great family gatherings space, 1st floor master suite with private bath, walk in closet, & dressing area, professional landscaping, private deck off of the family room, and a screened in porch which is great for enjoying the breeze and beautiful surroundings. This is truly a one of a kind home that must been seen. Call to schedule your appointment today!!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,397
Status:
Active
MLS#:
MDKE113952
Type:
Single Family
Subdivision:
College Heights
Lot size:
0.29 Acres
Year built:
1962
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Brick rancher within the town limits offering a front porch, screened rear porch for privacy, attached garage with an enclosed breezeway between the house and garage, open floor plan with gas burning fireplace...home has been well maintained

Beds:
3
Baths:
2.00
Sq.Ft.:
1,248
Status:
Active
MLS#:
MDKE113942
Type:
Single Family
Subdivision:
Kent County
Lot size:
0.46 Acres
Year built:
1970
Courtesy: Keller Williams Select Realtors
View additional info

Like new 3 bedroom/2 bath rancher. This home was completely updated in 2017 with new plumbing, electrical,insulation, HVAC, drywall, doors, flooring, lighting, paint, appliances. Enclosed rear porch, partially fenced rear yard and detached garage. Gutter guards, Updated landscaping, Tranquil views of pasture and pond.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,906
Status:
Active
MLS#:
MDQA136898
Type:
Single Family
Subdivision:
Chestertown/Queen Anne's County
Lot size:
1.7 Acres
Year built:
1958
Courtesy: Coldwell Banker Residential Brokerage-Annapolis
View additional info

Minutes from Chestertown, shops, Washington College, restaurants and cultural events. One level living on the Chester River on one and a half acres. Private dock and a nice sandy beach - you will feel like you are on vacation every day. Waterviews from almost every room and the most amazing sunsets. LARGE screened-in porch and decks. Large kitchen and pantry with lots of storage. Three car garage and workshop. Whole house generator. Perfect second home with a separate wing for your guests. Welcome home to the Eastern Shore of Maryland.

Open House:

Saturday, 4/6 11:00-1:00PM

Beds:
4
Baths:
3.00
Sq.Ft.:
3,708
Status:
Active
MLS#:
MDKE113930
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.33 Acres
Year built:
2006
Courtesy: Doug Ashley Realtors, LLC
View additional info

Starting with the outside, this home has undergone many improvements in the last two years. Custom patio and landscaping, garden boxes, custom wood shutters in the master suite, new ceiling fans in all bedrooms, living room and dining room, drywalled the garade. This is just a partial list of the improvements. Don't miss this beautiful listing in Coventry Farms. Open floor plan, with a gorgeous custom kitchen. This home seems to have it all. Call today to schedule a showing, Some lead time required.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,338
Status:
Active
MLS#:
MDQA136892
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.35 Acres
Year built:
1975
Courtesy: Long & Foster Real Estate, Inc.
View additional info

This "home" is beautiful and cozy; well maintained. Beautiful wood door opens to the foyer from the welcoming front porch. The exquisite stone fireplace is stunning, complete with oak mantel and slate hearth. The stamped concrete circular driveway and parking area is also unique. New vinyl plank flooring in the laundry/mud room. Nice walk-in pantry off mudroom for shopping convenience. Large garden area complete with hydrant and electricity. New HVAC installed in 2018. The shop comes complete with electric (100-amp service) and an outside hydrant. This home makes you feel at home! Come see this lovely one-of-a-kind home today!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,536
Status:
Active
MLS#:
MDKE113922
Type:
Single Family
Subdivision:
Chestertown In Town
Lot size:
0.11 Acres
Year built:
1900
Courtesy: Q. Williams Real Estate Associates
View additional info

This home close to historic district has just been remodeled. Walk to Washington College,shops, restaurants and waterfront.There is a large fenced yard and shed for storage. Off street parking can be available in back yard off the alley. The furnace is in the basement and there is baseboard hot water heat for a toasty warm quaint home in historical Chestertown

Beds:
3
Baths:
3.00
Sq.Ft.:
2,178
Status:
Active
MLS#:
MDKE113912
Type:
Condo/Townhouse
Subdivision:
Stepne Place
Year built:
1996
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Beautiful peaceful setting with lovely water views of the Chester River. Situated just a short stroll to H istoric downtown Chestertown with all its shops and great dining, this All brick two story townhome has much to be desired, 1st floor master bedroom with bath. Over sized 2 car garage with workshop.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDKE113428
Type:
Other
Subdivision:
Chester Arms
Lot size:
0.09 Acres
Year built:
1992
Courtesy: D N K Real Estate, LLC
View additional info

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDKE110396
Type:
Condo/Townhouse
Subdivision:
Oak Hollow
Lot size:
0.05 Acres
Year built:
2004
Courtesy: Rosendale Realty
View additional info

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. Priced to sell!

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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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