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Chestertown MD Real Estate & Homes for Sale

115 Properties Found

The median home value in Chestertown, MD is $231,000. This is higher than the county median home value of $200,000. The national median home value is $209,892. The average price of homes sold in Chestertown, MD is $231,000. Approximately 43% of Chestertown homes are owned, compared to 42% rented, while 15% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


Sort Results:
1–25 of 115 properties displayed
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Beds:
4
Baths:
4.00
Sq.Ft.:
2,492
Status:
NEW LISTING
MLS#:
MDKE100005
Type:
Single Family
Subdivision:
Fannell's Meadow
Lot size:
10 Acres
Year built:
2006
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore Vermont style farmhouse built in 2006 is set on a rural 10-acre meadow backing up to woods. The farmland across the street is in conservation. This beautiful, thoughtfully designed home with two geo-thermal wells, high ceilings and large windows offers pastoral views of fields and woods, yet is surprisingly located just 5 minutes from the Chester River and Chestertown~s historic district. Maple hardwood floors, wood detail and a stunning Finnish Tulikivi soapstone wood stove create warm, bright interior spaces, while serene views from the screened porch and terrace invite outdoor living. Charming separate guest quarters, library, media room and a basement with large windows and high ceilings are among other desirable amenities. The property is also ideal for a horse farm. Founded in 1706, Chestertown is set on the banks of the Chester River where visitors and residents alike enjoy strolling along the brick walkways lined with 18th century homes, cafes, shops, live theater, river walk and waterfront dining. It is also home to Washington College, the Chester River Yacht and Country Club and Wilmer Park on the Chester River. Kent County also offers beaches, public landings, rails to trails for hiking and biking, the farmers market and Eastern Neck National Wildlife Refuge. Chestertown is located about 90-minutes from Washington and Philadelphia.

Beds:
2
Baths:
1.00
Sq.Ft.:
884
Status:
NEW LISTING
MLS#:
MDQA141196
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1963
Courtesy: Rosendale Realty
View additional info
Beds:
3
Baths:
2.00
Sq.Ft.:
1,092
Status:
NEW LISTING
MLS#:
MDKE115556
Type:
Single Family
Subdivision:
Washington Park
Lot size:
0.5 Acres
Year built:
1965
Courtesy: Century 21 Downtown
View additional info

BELOW MARKET FORECLOSURE SALE WITH PRICE NOW APPROVED AS AN ASSIGNMENT OF THE BANKS CONTRACT SOLD IN AS IS CONDITION FIX IT FLIP IT , ADD TO RENTAL PORTFOLIO FOR POSITIVE CASH FLOW AND GREAT RETURN EMAIL LA FOR SPECIAL ASSIGNMENT DOCUMENTS PLEASE SUBMIT HIGHEST AND BEST OFFER

Beds:
3
Baths:
2.00
Sq.Ft.:
1,404
Status:
NEW LISTING
MLS#:
MDKE115566
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.46 Acres
Year built:
2005
Courtesy: D N K Real Estate, LLC
View additional info

3 BR Cape Cod in quiet, waterfront community of Chesapeake Landing. Located just off Worton Creek in beautiful, historic Chestertown. A short drive to the restaurants and shops of Rock Hall on the Chesapeake Bay. Home located in a peaceful cul de sac surrounded by trees and tranquility. Recent upgrades include all new carpet & flooring, professional painting, and new side entry door. 1st level Master BR with full bath. Upstairs, 2 BR and full bath. Large, eat in kitchen. Living Room. Separate front room for dining, office or family room needs. Oversized back deck and groomed back yard is perfect for entertaining. Community is water access with 2 marinas, boat slips and docks. A perfect location to keep your boat for a weekend away on the beautiful Eastern Shore or to make this your permanent home.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,459
Status:
NEW LISTING
MLS#:
MDKE115548
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.69 Acres
Year built:
2004
Courtesy: Doug Ashley Realtors, LLC
View additional info

This home looks barely lived in! As you walk in the front door you are welcomed with an open floor plan with wood floors, cathedral ceiling, skylights that brighten the room, formal dining area and a gas log fireplace to take the chill off. The kitchen has all of the major appliances plus a little breakfast nook. The split bedroom floor plan has the owners suite at one end of the house and the additional bedrooms are at the other end. The basement is partially finished and provides a walk out to the back yard. The rear deck overlooks the backyard and the open space area for the community. There is a 2 bay garage with a propane wall gas heater could allow for a small workshop. There is even a central vacuum system!!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,348
Status:
Active
MLS#:
MDQA141104
Type:
Single Family
Subdivision:
Kingstown
Lot size:
0.26 Acres
Year built:
1944
Courtesy: Doug Ashley Realtors, LLC
View additional info

Cute Cape Cod that was updated 8+/- years ago with replacement windows, heat pump and more. Living room is carpeted but has wood flooring underneath. Dining has wood floors. There is a sitting area/possible office area off the living room. The partial basement is neat and tidy. The rear deck overlooks the private backyard. There is even a one car garage. Property is zoned Suburban Commercial so it allows for uses other than residential. Just a short drive over the Chester River Bridge to Historic Chestertown.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,656
Status:
Active
MLS#:
MDKE115544
Type:
Single Family
Subdivision:
Quaker Neck
Lot size:
51.55 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
View additional info

Excellent Hunting and Waterfront - the Best of Both Worlds! Visit the grassymeade website for ALL information. As you will see, the location of the main house, 3 cottages, in-ground pool & pool house in the critical area buffer make this waterfront farm compound offering one that is extraordinary and extremely rare. Situated on the banks of Comegys Bight roughly 7.5 miles from Historic Chestertown and 16 +/- nautical miles from the Chesapeake Bay is a 51.55-acre whimsical oasis with nature & riding trails, pastures, barns, farmland, woodlands... a special place some refer to as Camelot that could be yours!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,248
Status:
Active
MLS#:
MDKE115522
Type:
Single Family
Subdivision:
Fairlee
Lot size:
0.78 Acres
Year built:
1965
Courtesy: Sassafras River Realty, Ltd.
View additional info

Well maintained rancher with major renovations~ Just finished updating Kitchen including all new appliances, Bathrooms, HW flooring refinished, fresh Paint, all new carpet in all BR. New boiler, new water heater, new central A/c in 2011. Full basement -Office/den in basement w/ built-in book shelves. Partially fenced in rear of property. Blacktop drive & new landscaping. Nice shade in the large yard.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,004
Status:
Active
MLS#:
MDQA141026
Type:
Single Family
Subdivision:
None Available
Lot size:
1 Acres
Year built:
1992
Courtesy: Village Real Estate Company LLC
View additional info

AMAZING CONTEMPORARY HOME! Pristine condition following a through renovation from top to bottom including all new roof, skylights, hardwood flooring, carpet, brand new central heating and air conditioning, new wiring, new plumbing, new lighting, and a fully encapsulated crawlspace. The stylish new kitchen has an awesome layout for cooking and entertaining with updgraded stainless appliances, granite countertops, subway tile backsplash, and barnwood accents. The first floor master bedroom features a HUMONGOUS walk in closet and a luxurious private bathroom with tiled shower. The home also boasts a large deck for entertaining and a 1 car attached garage and all of this one just over an acre. At a price like this, it's too good to be true! Come see for yourself today!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,997
Status:
Active
MLS#:
MDKE115526
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.27 Acres
Year built:
2007
Courtesy: Continental Real Estate Group
View additional info

Spectacular 4 Bedroom 3.5 Bath home in COVENTRY FARMS II for SALE. Located just outside of Chestertown's Historic District. This is the beautiful Victoria model from Ryan Homes. This home has all the upgrades that were available at time of purchase including upgraded cabinets, granite countertops, hardwood floor, ceramic tile, and carpet. This home has a finished basement with a full bath. This home had the additional bump outs added including a morning room and sitting room in the owner's bedroom.

Beds:
3
Baths:
1.00
Sq.Ft.:
2,376
Status:
Active
MLS#:
MDKE115442
Type:
Single Family
Subdivision:
None Available
Lot size:
1.3 Acres
Year built:
1969
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This lovingly maintained home is located in the middle of Kent County's Prime Farmland surrounded by pastoral views and has been updated over the years including new windows, crown molding, stainless steel appliances, roof and so much more. Five minutes from Downtown Chestertown this 1.3 acre property is located in the Agricultural District and allows up to 8 chickens (see zoning for more info). This home features a full home Generac Generator, gas fireplace, newly painted exterior, new landscaping, original wood floors ( & under the carpet) and a unique split level rear entrance. The side entrance has a spacious deck and ramp that adjoins the large black top driveway. The unfinished basement is the same size footprint as the main floor and can be turned into finished living space. About an hour commute to the PA line on 95 or an hour and fifteen minute commute to BWI!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,600
Status:
Active
MLS#:
MDKE115520
Type:
Single Family
Subdivision:
Downtown Chestertown
Lot size:
0.05 Acres
Year built:
1852
Courtesy: Select Land & Homes, LLC
View additional info

A charming colonial on S Kent Street. This tasteful renovation features 3 bedrooms, 2 full updated bathrooms, pine and slate floors, updated HVAC,a new roof, and modern kitchen. Enjoy the open floor plan which leads out to a brick patio and gardens. Located on a quiet street this home has the conveniences of walking to the downtown waterfront, shops and restaurants. The historical charm and move in condition truly make this home a must see!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,120
Status:
Active
MLS#:
MDKE115474
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.39 Acres
Year built:
1994
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Wonderful home in water-oriented Chesapeake Landing. Well maintained and tasteful renovations done in the kitchen and upscale wood floors. Open floor plan. Lovely patio in rear of the house for shaded private outdoor meals. Enjoy the views of deer and birds in the woods across the street. Keep your boat at the marina or launch it from the community area. Welcome Home!

Beds:
1
Baths:
1.00
Sq.Ft.:
756
Status:
Active
MLS#:
MDKE115496
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:
3
Baths:
2.00
Sq.Ft.:
1,392
Status:
Active
MLS#:
MDQA140940
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.76 Acres
Year built:
1976
Courtesy: Doug Ashley Realtors, LLC
View additional info

One level living. Master suite has new carpet, a walk in cedar closet, master bathroom features a walk in shower. Large living room with wood stove. Three bedrooms/2 full baths. Detached 2 car garage, shed, and a wonderful yard. New gas stove in 2019. new window unit 2019. Sump pump in crawl space with lifetime warranty. There used to be a pool, but this was removed and closed in

Beds:
3
Baths:
1.00
Sq.Ft.:
1,200
Status:
Active
MLS#:
MDKE115484
Type:
Single Family
Subdivision:
Quaker Estates
Lot size:
0.64 Acres
Year built:
1963
Courtesy: Doug Ashley Realtors, LLC
View additional info

Nice little rancher in Quaker Estates waiting for you to put your stamp on it! Family room addition off kitchen makes it roomier than most. Home will need some updating and repairs but with a Newer roof, Updated bathroom, and hardwoods under carpet, you've got a head start to your dream home!

Beds:
4
Baths:
3.00
Sq.Ft.:
4,358
Status:
Active
MLS#:
MDKE115462
Type:
Single Family
Subdivision:
Great Oak Estates
Lot size:
1.36 Acres
Year built:
2005
Courtesy: Cross Street Realtors, LLC
View additional info

This exquisite Chesapeake Bay Waterfront home is the definition of perfection! Stunning panoramic sunsets and broad water views are yours from nearly every room. An incredible four season room with large picture windows and tile floors flows into the gourmet kitchen and open dining area. The kitchen features a six-burner Viking gas range and double oven, granite counters, custom wood cabinetry, and large island. A two-story living room with double-sided gas fireplace allows access to the waterside deck with elevated views. Some of the best views are reserved for the beautiful Master suite, offering vaulted ceilings, a private balcony, and a large Master bath with tiled shower enclosure, double vanity and luxurious soaking tub. Three additional bedrooms and two full baths provide ample space for guests. Rounding out the complete package is the sizeable finished basement with premium sound, flat screen and projector and game area, as well as an attached 3-car garage. Bold, elevated views, a private beach, privacy, and a long list of amenities make this property one of a kind!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,087
Status:
Active
MLS#:
MDKE115466
Type:
Single Family
Subdivision:
Tolchester
Year built:
1955
Courtesy: Rock Hall Properties Real Estate
View additional info

Why rent when you can buy one of these affordable homes for less than $900 per month. There are three, 2 bedroom duplex-style homes available. Completely renovated and upgraded, these single level units have new carpet, stainless steel appliances, HVAC & metal roofs. Up to 97% financing is available to qualified buyers. Buyers must be owner-occupants.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,425
Status:
Active
MLS#:
MDKE115382
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.71 Acres
Year built:
2015
Courtesy: RE/MAX One
View additional info

From the time you enter this property, it exceeds all expectations. Custom built, designed by owner, no space is without purpose. Great entertainment areas, efficient, energy smart, wood & tile flooring, top of the line materials from the construction to the lighting fixtures. There is nothing like this home. And then, there are the incredible bay views! Mahogany front door, Ipe porch, Hardiplank siding, NANA WALL opens to bring the outside in... screens, remotely controlled. Room for a garage, plenty of parking, over sized hot tub with adjustable privacy walls and outside shower. Waterviews from almost every room, Master suite w/ huge walk in shower, whirlpool tub, full vanity wall, walk-in closet, outside balcony. Main level has extensive seating areas in great room for breakfast bistro, cocktails, dining, wine bar, coffee station, cocktail station, large porches and balcony. Cozy living room with propane fireplace. Kitchen w/ top of the line appliances, walk in pantry/mud room. The list is too long to cover. This is a must see! Don't miss a photo, it all tells a story.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,269
Status:
Active
MLS#:
MDKE115458
Type:
Townhouse
Subdivision:
Tolchester
Year built:
1955
Courtesy: Rock Hall Properties Real Estate
View additional info

Buy for less than you can rent in Kent County's newest affordable living community! Six 3 bedroom townhouse-style units are available in Tolchester Village Condominiums. The complex has been completely renovated & upgraded with public water & sewer, new roofs, new kitchens & baths, new HVAC, etc. Total cost of ownership is less than $900 per month. Financing avilable to qualified buyers. Buyers must be owner occupants.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,616
Status:
Active
MLS#:
MDKE115452
Type:
Single Family
Subdivision:
College Heights
Lot size:
0.46 Acres
Year built:
1959
Courtesy: Doug Ashley Realtors, LLC
View additional info

Immaculate condition home with four bedrooms, new carpet, wood floors, great landscaping. Two bedrooms on the main level with 2 full baths, and 2 bedrooms upstairs with 1.5 baths. Nice location on a dead end street. There are 2 laundry areas, one in the basement and one upstairs in the half bath.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDKE115460
Type:
Single Family
Subdivision:
Chester Arms
Lot size:
0.09 Acres
Year built:
1980
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Easy living on a quiet street in Chestertown. Walk to the grocery store, pharmacy and other shopping and dining. 3 bedrooms and one and a half bath. Enclosed rear porch. Fenced back yard and a shed for storage.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,476
Status:
Active
MLS#:
MDKE115456
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.08 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Quiet Mill St with historic charm. A contemporary open floor plan for this classic Victorian. Original wood floors, East Lake style mantle, bulls eye molding, plantation shutters, wood stove, upgraded kitchen. Large rear yard has a patio, gardens, and paths. Living roof on the shed. Enjoy the church bells. A stone's throw from the library, gym, college, dining and shops. Store your bikes in the side yard.

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA140770
Type:
Single Family
Subdivision:
Blakefield
Lot size:
1 Acres
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

CONSTRUCTION UNDERWAY. 3 BEDROOM 2 BATH RANCHER WITH GARAGE. ONE OF 9 LOTS TWO PICK FROM. HOUSE GOING TO BE LOADED WITH UPGRADES. SIT BACK AND ENJOY THE VIEWS. OPEN FLOOR PLAN OR BRING US YOUR PLANS AS WELL. YOU CAN PICK OUT YOUR COLORS AND MAKE THIS BABY ALL YOURS.

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA140774
Type:
Single Family
Subdivision:
Blakefield
Lot size:
1 Acres
Year built:
2019
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

PRICES STARTING AT $269,000.00. 9 LOTS TO PICK FROM. HOUSE IS UPGRADED WITH STAINLESS STEEL APPLIANCES, UPGRADED FLOORING. OPEN FLOOR PLAN AND CAN PICK COLORS OF HOUSE. OR BRING US YOUR PLANS TO PRICE. PICTURE IS OF HOUSE TO BE BUILT

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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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