Chestertown MD Real Estate & Homes for Sale

116 Properties Found

The median home value in Chestertown, MD is $230,000. This is higher than the county median home value of $180,000. The national median home value is $177,414. The average price of homes sold in Chestertown, MD is $230,000. Approximately 37.21% of Chestertown homes are owned, compared to 43.01% rented, while 19.78% 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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$199,000

118 Malone Avenue Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9870816
Type:
Single Family
Subdivision:
Foxley Manor
Lot size:
0.34 Acres
Year built:
1973
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Awesome home that has been lovingly cared for with many updates. Basement has been partially finished with a kitchenette and pellet stove. Gleaming wood floors are throughout most of the main level. Tile in the dining area. The rear covered deck is great for summer entertaining. Brick faced with with vinyl siding added in the past few years. Heat pump for heating and cooling. House Generator!

$265,000

131 Queen Street UNIT UNIT1 Chestertown, MD 21620

Beds:
2
Baths:
3.00
Sq.Ft.:
1,684
Status:
NEW LISTING
MLS#:
KE9855389
Type:
Condo/Townhouse
Subdivision:
Chestertown Historic District
Year built:
1900
A broker reciprocity listing Courtesy: Champion Realty, Inc.
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Take Advantage of this Rare Opportunity to Own One Unit of A Charming Duplex Condo in the Heart of Chestertown Historic District * Known As "The Willis Double House" * Perfect in-town Location; Walk to Shops, Restaurants, Parks,Theater and the Beautiful Chestertown, Chester River Waterfront * Just a short drive to Historic Washington College * Move-in Ready * Call Today for Your Personal Showing !

$298,975

211 Leeds Court Chestertown, MD 21620

Beds:
5
Baths:
4.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9861355
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.34 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
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Large 5-Bedroom Colonial in Coventry Farms offers a fully finished basement & a brand new composite deck! A large kitchen w/ ceramic tile flooring, gas range & kitchen island opens to breakfast area & family room. Also offers a formal dining room, living room & Master Suite w/ 2 walk-in closets & large bath w/ soaking tub. Located at the end of a quiet cul-de-sac w/ 2-car garage & paved drive!

$275,000

209 Campus Avenue Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9866525
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.36 Acres
Year built:
1947
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Co
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Upgrades completed! This charming & spacious home in Chestertown, close to Washington College & walking distance to Fountain Park will sweep you off your feet. Wood floors, granite kitchen counters, screened porch and fenced backyard. Relax in this beauty and enjoy your close proximity to everything Chestertown has to offer! Beautiful yard with mature trees and a 2 car garage complete the picture.

$229,000

301 Campus Avenue Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
KE9865380
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1964
A broker reciprocity listing Courtesy: Sassafras River Realty, Ltd.
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Brick Home in Chestertown ready for you to move-in! Renovations have been made including Kitchen & A/C. Hardwood floors throughout most rooms, fireplace in Large Living Rm, bright rooms with plenty of closet space & built-in shelves. Storage area attached to carport. Blacktop driveway. Corner lot that is landscaped.

$112,500

116 East Street Chestertown, MD 21620

Beds:
2
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9863836
Type:
Single Family
Subdivision:
Reba L Anthony Subdivisi
Lot size:
0.53 Acres
Year built:
1965
A broker reciprocity listing Courtesy: Coldwell Banker Residential Brokerage
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**Plenty of Room for updates and improvements (add a 3rd bedroom) located in Queen Anne's County, and walking distance to the Chester River. Fully fenced in back yard, enclosed sunroom, detached garage, paved driveway,Fenced in rear yard mature landscaping. Only minutes from downtown Chestertown and Washington

$115,000

203 Hilltop Lane Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9863520
Type:
Townhouse
Subdivision:
Tim Dills Sub
Lot size:
0.05 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Coldwell Banker Residential Brokerage
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Nice Townhome in small Subdivision of Chestertown. Easy to show , Traditional Layout*Make an appt. soon!

$379,900

110 Kent Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,600
Status:
Active
MLS#:
KE9861885
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.05 Acres
Year built:
1852
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
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Restored with superior quality - wood clapboard exterior, natural pine & slate floors, soapstone counters, detailed moldings & chair rail, shiplap pine walls in dining area, preserved interior doors, hardware, trim, stair treads & railing, french doors, brick alley & patio, new structural piers, 2 sump pumps in concrete crawlspace, new floor joists, new sewer lines, new electric, plumbing & roof!

$258,500

204 Brown Street Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9845730
Type:
Single Family
Subdivision:
None
Lot size:
0.51 Acres
Year built:
1950
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
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Located in a quiet Chestertown community, this spacious home offers easy access to both the local hospital and Kent County Middle School. With large family spaces and a big back yard, this house is great for those seeking either a quiet life or who are interested in entertaining.

$394,000

1530 McGinnes Road Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
2,858
Status:
Active
MLS#:
QA9845321
Type:
Single Family
Subdivision:
Not In A Subdivision
Lot size:
4.55 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
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Spacious home w/ privacy on 4.5+ wooded acres, including additional buildable lot, close to Chestertown & 301. Huge Master Suite w/ large en-suite bath w/ shower & claw foot tub, dressing/sitting room & walk-in closet. Brazilian cherry & bamboo flooring throughout the main level w/ an open kitchen & family area. The 2-car garage has been converted for daycare but is easily put back.

$195,000

913 Round Top Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9858146
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
2017
A broker reciprocity listing Courtesy: Rosendale Realty
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JUST A BIT OVER RESALES GETS YOU QUALITY RANCH STYLE HOME WITH OPEN LIVING AND KITCHEN. STILL TIME TO MAKE SELECTIONS AND UPGRADES AVAILABLE. MODEL UNDER CONSTRUCTION IN KENT CO. ON CEDAR AVE. ARCH SHINGLES, WOOD LAMINATE FLOORING, NICE FLOOR PLAN. LEVEL LOT WITH EXISTING SHED ON SITE FOR EXTRA STORAGE. COMMUNITY HAS VOLUNTARY HOA. MAIN PIC IS A SIMILAR HOME ON A DIFFERENT LOT MHBR # 3717

$154,982

24745 Langford Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9857177
Type:
Single Family
Subdivision:
Kent County
Lot size:
0.4 Acres
Year built:
1961
A broker reciprocity listing Courtesy: RE/MAX Associates
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3 BR / 2BA brick ranch , under construction and at point now where the contractor is offering a qualified buyer to go through a selection of finishes to completion. Budget to be determined. Showing by appointment only.

$100,700

10355 Bunting Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,248
Status:
Active
MLS#:
KE9856919
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.34 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Real Home Services and Solutions, Inc.
View additional info

One level living in this single family home located close to Worton Creek! Built in 2002, this home has 1248 finished square feet, three bedrooms, two full baths, large living area and large rear deck. Not too far away is Tolchester Beach and Tolchester Marina for all the water-lovers! This home needs a few cosmetic items but it priced right; come see this one today!

$185,000

10634 Millbrook Drive Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,404
Status:
Active
MLS#:
KE9856549
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.45 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Rock Hall Properties Real Estate
View additional info

Charming cape cod style home in Chesapeake Landing. Popular 3BR/2 bath layout with one bedroom and full bath on the first floor and two bedrooms and another full bath on 2nd floor. Dormers on the 2nd floor provide lots of natural light. Low maintenance vinyl siding and easy-care electric heat pump make this a nice 2nd home or vacation property. Rear deck for entertaining and storage shed for toys.

$36,000

8636 Caulks Field Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,232
Status:
Active
MLS#:
KE9854403
Type:
Single Family
Subdivision:
0000
Lot size:
1.48 Acres
Year built:
2001
A broker reciprocity listing Courtesy: Real Home Services and Solutions, Inc.
View additional info

Auction property. 4.5% Buyer Premium charged buyer at closing. No inspection contingency accepted. REO Property sold As-Is w/o repair, warranty or Seller Disclosure. The Listing Broker & Seller assume no responsibility & make no guarantees as to the accuracy of info herein. Seller will accept cash, conventional, 203k offers only. No water activation allowed. Buyer pays entire transfer tax.

$158,000

23706 L Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,152
Status:
Active
MLS#:
KE9854138
Type:
Single Family
Subdivision:
None
Lot size:
3 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Move in ready 3 bedroom, 2 bath rancher on secluded 3 acres. Close to Chestertown. Perfect for your chickens and dogs.

$249,000

208 Mill Street Chestertown, MD 21620

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9851537
Type:
Single Family
Subdivision:
Downtown Chetsertown
Lot size:
0.08 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

PRICE REDUCED!!! This traditional historic home has original charm, gorgeous hardwood floors, numerous upgrades & a professionally designed backyard sanctuary... ALL in the HEART of Downtown Chestertown on a quiet cul de sac. Walking distance to everything - farmer's market, shops, restaurants, Washington College & the WATERFRONT! (Furnishings available, too!)

$3,000,000

24091 Providence Plantation Lane Chestertown, MD 21620

Beds:
5
Baths:
6.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9849997
Type:
Single Family
Subdivision:
None
Lot size:
76.07 Acres
Year built:
1781
A broker reciprocity listing Courtesy: Brandywine Fine Properties Sothebys INTL Realty
View additional info

A quintessential 76-acre Eastern Shore waterfront estate built in 1781 & restored in 1990. Providence Plantation is very livable with a fabulous 1st flr master BR suite now with a new 3BR tenant house, dock with lift & an in-ground pool plus a 3rd home may be built to create a family compound. Easy access to Annapolis, DC or north to Philadelphia. Agent/Owner

$1,140,000

10080 Third Point Road Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
2,900
Status:
Active
MLS#:
KE9847563
Type:
Single Family
Subdivision:
Great Oak Estates
Lot size:
1.6 Acres
Year built:
1962
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Water views from literally every room! Beautiful glass windows showcase the panoramic southern exposure with a spectacular view of Fairlee Creek! Over 300 feet of rip-rapped waterfront, 5'+/- MLW and a dock with a 15,000 lb boat lift and jet ski lift. There is access from most of the rooms to your spacious water front deck, great outdoor entertaining. This is a home to be loved and treasured!

$269,900

602 Rosin Drive Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9847426
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.49 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Co
View additional info

Waterfront home in Chester Harbor. Large backyard leads to pier for your boat. Catch the tide and boat into the Chester River. Enjoy fishing, crabbing and nature on the water. House has some upgrades including kitchen and bathrooms. Some maintenance repair work needed to bring this gem to perfection. Great second home or full time living. Minutes to down town Chestertown.

$299,000

530 Cannon Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9845702
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.21 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Renovated Colonial Farm house in downtown Chestertown with off street parking detached garage with tons of storage. Kitchen updated 2 years ago and all new appliances.Wood floors through-out. Vaulted ceilings in family room and master bedroom. Beautifully landscaped with fenced in yard and great outdoor living area. Wood stove with a pizza oven in family room.

$109,900

27895 Morgnec Road Chestertown, MD 21620

Beds:
4
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9845628
Type:
Single Family
Subdivision:
Morgnec
Lot size:
0.94 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

This ten year old rancher has four bedroom and two baths, with a functional floor plan, on almost an acre. Conveniently located just 5 minutes to Chestertown and 8 minutes to Route 301. It's just waiting for the right buyer to give it the attention it needs.

$650,000

310 Hickory Lane Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
3,300
Status:
Active
MLS#:
QA9842553
Type:
Single Family
Subdivision:
Pheasant
Lot size:
20 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Keller Williams Flagship of Maryland
View additional info

Custom home situated on 20 acres. 600' of River front property with permittable Boardwalk and Pier. Every window provides a fantastic view. Three River rooms (one on each floor) provide amazing views of the Chester River and the areas Wildlife. Home offers charm with many wood accents throughout. Adjacent wetlands ; the opposite side of the river cannot be developed.

$214,000

211 Waldo Drive Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9838024
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1982
A broker reciprocity listing Courtesy: Rosendale Realty
View additional info

So close to all Chestertown's quaint attractions yet still has the neighborhood feel. Cozy home with beautiful brick fireplace, Exposed Beams, High Ceilings with sky lights! Open concept Kitchen, Hardwood floors, large deck off back Sunroom along with the attached garage and separate -Laundry/Mudd room make this house a must see! Make your appointment soon!

$329,000

204 Birch Run Road Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9833432
Type:
Single Family
Subdivision:
Mile Tree Village
Lot size:
0.45 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Co
View additional info

Mile Tree Village is a special place; a private quiet Cul-de-Sac. Walk into Chestertown, Washington College or the Chester River. Nicely fenced large rear yard with views of the large deck, sunny Florida room and the Chester river.This cape has wood floors, 2 fireplaces, attached garage and a first floor master. Just enjoy the serenity of this great spot.

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The data on this web site comes in part from Metropolitan Regional Information Systems (MRIS). The listings presented on behalf of MRIS may come from many different brokers but all MRIS listings may not be visible on this site. Information is believed to be reliable, but not guaranteed.

Chestertown MD Real Estate Listings Provided By:

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