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Chestertown MD Real Estate & Homes for Sale

34 Properties Found

The median home value in Chestertown, MD is $270,000. This is higher than the county median home value of $207,500. The national median home value is $266,648. The average price of homes sold in Chestertown, MD is $270,000. 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.


1–25 of 34 properties displayed
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Open House:

Saturday, 5/1 12:00-2:00PM

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
NEW LISTING
MLS#:
MDKE118012
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

There are only 6 units left... so come take a look now! Only 2 bedroom townhomes are left! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Open House:

Saturday, 5/1 12:00-2:00PM

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
NEW LISTING
MLS#:
MDKE118010
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

There are only 6 units left... so come take a look now! Only 2 bedroom townhomes are left! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
1,036
Status:
NEW LISTING
MLS#:
MDKE117994
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.03 Acres
Year built:
1920
Courtesy: Select Land & Homes, LLC
View additional info

Enjoy Chestertown living in this completely renovated Downtown colonial! The first floor features an open floor plan with living room and gas fireplace, dining room and updated kitchen with side door leading to the outdoor patio. Upstairs offer two bedrooms and a renovated full bathroom. The tasteful patio offers built in seating around a firepit, planter boxes to grow herbs and vegetables and exterior access that leads to Downtown, waterfront, shops and restaurants. Bike trails and park for your enjoyment are nearby. The delightful, turnkey home blends history with comfort and convenience.

Open House:

Saturday, 4/24 11:00-2:00PM

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
3,300
Status:
NEW LISTING
MLS#:
MDKE117926
Type:
Condo
Subdivision:
Chester River Landing
Year built:
2008
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Bring your sailboat! The water depth is 20'! Slip A5 is included. Grace and elegance name this Waterfront 3 level townhouse. Garage included. Top Hat construction with only the best of amenities. Enter the front door and the open floor plan gives views of the Chester River through the Living Room. Don't worry about the stairs, the elevator goes to all 3 floors. The third floor was originally 1 large bedroom that has been converted into 2 offices. Use them as you please. The views from the first Floor Back porch and the upstairs balcony give mesmerizing views. Do you just want to do some crabbing and fishing? There's a pier for that too. Or stroll along the beautifully landscaped walking paths. A community pool to enjoy in the warm weather. Enjoy the calming peace and good life in this Chestertown Waterfront home. Chester River Landing has it all.

Open House:

Saturday, 5/1 12:00-2:00PM

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
NEW LISTING
MLS#:
MDKE117998
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

There are only 6 units left... so come take a look now! Only 2 bedroom townhomes are left! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
7
Baths:
5 Full/2 Half
Sq.Ft.:
10,328
Status:
NEW LISTING
MLS#:
MDKE117878
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
21.02 Acres
Year built:
1800
Courtesy: Select Land & Homes, LLC
View additional info

This Majestic stately residence is perched at a perfect elevation with incredible views of undeveloped, preserved farmland and gently sloping lawn to the 1000' of white sandy beach on the Upper Chesapeake Bay. This awesome property offers ultimate privacy with the convenience to several urban centers within 90 minutes away. Historic Chestertown and the bayside town of Rock Hall are only moments away as well! Property features include a restored Georgian Colonial main residence in great condition with many original features and numerous recent updates, a large enclosed pool with attached recreation play house, 4 stall barn with 4 acre fenced pasture, tenant house, detached garages, extensive patios and landscape features, gorgeous private beach with bath house and much, much more! Come take a look and take advantage of all the value at a very reasonable asking price! Subject to Maryland Environmental Trust Easement, see documents.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,454
Status:
NEW LISTING
MLS#:
MDKE117962
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Heights-Rt 213 N
Lot size:
0.21 Acres
Year built:
1956
Courtesy: Cross Street Realtors LLC
View additional info

PRIME LOCATION!!! This adorable 3 BR, 1 BA bungalow is located on one of the main thoroughfares in Chestertown. Zoned Intense Village which allows residential and/or a broad range of commercial uses. The living space includes a large family room off the galley kitchen, new heat-pump with central air, new carpet, screened in-porch and a detached 2-car garage with ample off street parking. Close to all Chestertown offers; Washington College, restaurants, hospital, local shops, new marina and much more. Lots of possibilities here!

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,858
Status:
NEW LISTING
MLS#:
MDQA147250
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
4.55 Acres
Year built:
2004
Courtesy: Chaney Homes, LLC
View additional info

Beautiful Charming Colonial on over 4.5+ acre's - secluded wooded lot (some cleared areas) in Queen Anne's County - Lot #1 is 2 acres and already perc approved for additional build - Lot #2 - 2.55 wooded acre lot holds charming 4 bedroom 3 bath custom built colonial with unique features and updates throughout - 2600+ square feet - Beautiful brick fireplace with gleaming cherry hardwood floors - New carpet just installed - open floor plan with formal dining room and large eat in country kitchen - Room for an in-home office or keep as additional recreational area - luxury master suite with loft, walk in closet and private en-suite master bath - charming claw tub and separate shower offer relaxation after a long day - Laundry on Upper floor for added convenience - Work from home in your built in Studio on the main floor and when your done....float in the above ground pool and entertain off the large paver patio just off the back sliders - Relax on a beautiful wrap around front porch - Nature abounds - NO HOA RESTRICTIONS - Room to indulge your backyard desires - Perfect location with minutes to 301 - Downtown Chestertown - Centreville or The Bay Bridge

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,064
Status:
NEW LISTING
MLS#:
MDKE117958
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.06 Acres
Year built:
1920
Courtesy: CENTURY 21 New Millennium
View additional info

INVESTOR OPPORTUNITY. Great rental property in a college town. Well maintained, updated and reasonably priced home located near the heart of Chestertown. Walking distance to fine arts, restaurants and waterfront. Potential space for a half bathroom off of the dining room. Safe location, close to elementary school. Hardwood throughout, and a fenced-in backyard with a 10 x 20 storage shed. Perfect for a new family or someone looking to downsize. A rare find. Sold As-Is.

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,050
Status:
NEW LISTING
MLS#:
MDKE117956
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.37 Acres
Year built:
1969
Courtesy: The Hogans Agency Inc.
View additional info

Cozy ranch style lakefront cottage on large lot with beautiful hardwood floors - one half mile from Public Landing Marina. Scenic views and wildlife abound with outstanding fishing on the the lake. A must see - your enjoyment awaits!

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,356
Status:
Active
MLS#:
MDKE117886
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.31 Acres
Year built:
1966
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Well maintained 4 BD 2 BA ranch in College Heights. Office, wood floors throughout with an attached garage and a detached garage/shop. Nice deck out back and beautiful mature trees. Close to the Historic District, Washington College, shops and restaurants. Tenant occupied so advanced notice needed.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,152
Status:
Temporarily Off Market
MLS#:
MDKE117900
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
3 Acres
Year built:
1978
Courtesy: Keller Williams Flagship of Maryland
View additional info

Temp of the market, till renters move out.-Looking to be away from it all, but close to amenities? Then you have found your home. Home is 1152 sq. ft. of main living on 3 acres, plus an additional .50 ac lot in front. Both lots are level. Main level living with large bright living room, country kitchen with dining area, and laundry closet. 3 bedrooms and 2 full baths. Front porch and back decking. Privacy and Location, Location, Locations. Short drive to Great Oak Landing Marina/Golf Club, Water, Speedway, and downtown Chestertown for shopping, restaurants, and pier. Stone throw to Rock Hall and Delaware. Please note -this home is not a mobile home as stated on tax records. The home is AS-IS and has renters on a month-to-month basis. Do not enter the property without an appointment. Septic was just pumped and inspected.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,400
Status:
Active
MLS#:
MDQA147184
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.34 Acres
Year built:
2021
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Beautiful 4 bedroom 2 bath in lovely Chestertown. Under Construction, but will be done within the month. An open kitchen to allow for all of the family to gather. Separate laundry room off of the kitchen. Master Bedroom has 2 large closets. This home has everything you need! Large family room, with lots of natural lighting. Settlement on date of completion.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,728
Status:
Active
MLS#:
MDKE117860
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.35 Acres
Year built:
1970
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Chestertown - This 3 bedroom 2 bath home sits in a beautiful family neighborhood walking distance from the Washington College campus. This home has had new windows installed, new gutters, a new water heater and new laminate flooring in the kitchen and dining room all within the last 2 years. A new central air and heating system was installed within the last 5 years. The solar panels produce plenty of energy and have no outstanding lease. There is a large back deck off the family room entrance perfect for entertaining. The back deck opens up to a large fenced in backyard. This home offers a Jack and Jill bath in addition to the master suite that has an attached dressing room. There is a full unfinished basement and a large attic with outside stair access that offers additional storage. The large living room offers plenty of space for family time in addition to the family room with a wood burning fireplace. The washer and dryer are on the main level of the house. An attached carport provides protection for your vehicle. Call today for your private showing!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,680
Status:
Active
MLS#:
MDKE117838
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.64 Acres
Year built:
1957
Courtesy: Doug Ashley Realtors, LLC
View additional info
Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,200
Status:
Active
MLS#:
MDKE117826
Type:
Condo
Subdivision:
Chester River Landing
Year built:
2007
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

You will appreciate peaceful living in this waterfront community on the Chester River just minutes from historic Chestertown. A light-filled and spacious open floor plan is wonderful for enjoying the elegant interior amenities. You will also want to sun bathe or swim in the lovely pool, walk the shell walking paths throughout the community and along the shoreline, go kayaking from the community launching area, or take a bike ride or walk into town. Lots of ways to enjoy the care-free Eastern Shore lifestyle! Boat slip available. 3 bedrooms, 2 1/2 baths and includes a garage. Gigabit fiber internet available.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE117708
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
168.77 Acres
Year built:
2002
Courtesy: Maryland Heritage Properties
View additional info

PENTRIDGE WOODS FARM, in an unspoiled corner of Marylandâ s Eastern Shore, could be a weekend refugeâ or your forever family home. On almost 170 private acres, with a modern and comfortable main house and a contemporary guest cottage down the road, this low-maintenance property has tilled fields, two ponds, and a dense forest. Pentridge Lane neighbors are a friendly community of mostly waterfront homes. Nearby Chestertown offers cultural and athletic events at Washington College, golf and sailing at the informal country club, a renowned farmers market on Saturdays, live music and theatre venues, a hospital, good schools, coffee shops and restaurants, and a thriving arts community. The area has long been a major sailing and cycling destination and is rapidly becoming an equestrian center. While Kent County fiercely preserves its agricultural heritage, it is less than a two-hour drive from Washington, Baltimore or Philadelphia and not much farther from the NYC area. The main house, designed by a Yale Architecture School grad as a modern farmhouse with a full basement, has four bedrooms, 2 ý baths, a large detached garage, and an interior courtyard garden. The center of the soaring open-plan main floor is a massive double-sided Finnish soapstone fireplace that divides the kitchen from the sitting area, with French doors opening onto the deck and brick courtyard. This floor also has a dining room/library, two bedrooms and a study/fourth bedroom. The second floor consists of a huge media room or studio and a large en-suite master bedroom. The distinctive two-story guesthouse (a short drive or ten minute walk from the main house) has a large deck and windows that wrap around the corners of the cube-shaped building. The guesthouse is currently a rental property but could easily revert to the owner's personal use. About eighty acres are farmed under a shared profit/loss arrangement by a local farmer (qualifying the owner for agricultural property tax benefits). The forest is prime deer-hunting terrain, also generating revenue. Because strict Kent County zoning laws protect agricultural land and the Chesapeake Bay watershed, this farm can never be subdivided and the deed also designates the woods as an avian refuge. As a result, the farm is home to resident and migratory birds, an oversupply of deer, as well as foxes, rabbits and other small animals. Weekend residents can enjoy all the farm offers with hardly any work, as the farming and garden maintenance are now done by trusted local people. But Pentridge Woods Farm would welcome more active participation by engaged owners, who might want to add an organic vegetable garden, experiment with different market crops, build a stable and keep horses, or establish their own vineyard. The possibilities are endless. Note: the listing agentâ s website has an aerial video and more info/photos. PLEASE NOTE; All Buyer agents MUST attend all showings and inspections before and after Contract. All appointments must to requested by AGENT, not clients.

Beds:
n/a
Baths:
2 Full
Sq.Ft.:
1,998
Status:
Active
MLS#:
MDKE117682
Type:
Single Family, Single Family-Detached
Subdivision:
Melitota
Lot size:
1.91 Acres
Year built:
2008
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Formerly used as a house of worship, this property is zoned Village which could allow for many different uses including a residence. The building is almost 2000 sq. ft. with a large open room and raised stage with a ramp. There are no stairs or pews. There are men's and women's restrooms with double vanities and the other rooms that could be bedrooms or kitchen. The parking lot is located in the rear. It is situated on 1.9 acres, backs to the trees and the views from the front are farm fields. There are many possible uses for the property including, but not limited too, single family dwelling, offices, retail, restaurant, personal service establishment and many more. Some uses are subject to a site plan review.

Beds:
3
Baths:
3 Full
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDKE117594
Type:
Townhouse
Subdivision:
Chestertown
Lot size:
0.05 Acres
Year built:
1999
Courtesy: Doug Ashley Realtors, LLC
View additional info

The Chester River is just across the open space of Wilmer Park, from this townhome! The living room, with vaulted ceiling, fireplace and sky lights, is bright and roomy. Relax on the rear deck, tend to your flowers in the tidy garden or sit in your rocker on the front porch and watch people as they enjoy Wilmer Park. Gleaming wood floors are throughout the main level. There is a main level bedroom and full bath on main level. There is a den area on 2nd level that would make a great office or open up the wall and have sitting room off of the bedroom, as it was originally designed. Easy stroll to the Chester River and the Chestertown Marina. This is a great place to hang your hat part time or full time.

Open House:

Saturday, 5/1 11:00-2:00PM

Beds:
5
Baths:
1 Full/1 Half
Sq.Ft.:
2,940
Status:
Active
MLS#:
MDKE117482
Type:
Single Family, Single Family-Detached
Subdivision:
Historic District Chestertown
Lot size:
0.2 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

Incredible home.. "The Pink Lady" This Victorian has been given a new lease on life with a completely updated, gorgeous new kitchen, shining floors, washer and dryer on main level. This house is beautiful. Great location, within steps to downtown shopping and restaurants, and just a couple of blocks from the Chester River. There is parquet flooring, granite countertops, a breakfast room, new windows, stained glass windows going up the classically beautiful staircase. Five bedrooms all total on the two upper levels. You will enjoy a sunny and bright reading level, and also a media area. It's just an incredible home, wrap front porch. The Pink Lady has been loved, updated but it is an historic home, and has it quirks, as any historic home has. That is the charm! The downstairs half bath Is an EASY conversion back to the full bath, plumbing still in place for that! New flooring in the half bath. OWNER WILL NOT TAKE A HOME SALE CONTINGENCY.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,400
Status:
Active
MLS#:
MDQA146558
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.23 Acres
Year built:
2021
Courtesy: Long & Foster Real Estate, Inc.
View additional info

*UNDER CONSTRUCTION* House to be ready within the month. Quiet and peaceful Eastern Shore living. 4 Bedroom 2 Full baths. Wonderful price in this competitive market to get what you want.. Very open floor plan with the entry, living room, dinning room and kitchen. Lot conveniently located to all the major routes, only minutes away from Downtown Chestertown and Centreville. A short easy commute to Middletown, Dover, Annapolis, DC, and the beaches. Located in QA County school district. Lot size not accurate. A bit over .5

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
4,305
Status:
Temporarily Off Market
MLS#:
MDKE117564
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.84 Acres
Year built:
1950
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock and sandy beach. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. House has had major remodels in 2000 and 2020. Town sewer. Not far from town but the property has a private feel. Come and be amazed!! All buyers must be pre-approved.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,400
Status:
Active
MLS#:
MDQA146372
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.42 Acres
Year built:
2021
Courtesy: Long & Foster Real Estate, Inc.
View additional info

CONTRACT FELL THROUGH. HOUSE WILL BE COMPLETE WITHIN THE NEXT WEEK OR SO. Photos are of model home. Your very own chance to own new construction, at a great price. Open kitchen, dining, and living area. 4 bedrooms, 2 full baths. Front, side, and back door. Very clean layout. Kitchen appliances included, wonderful laundry area. Located 45 minutes from the bay bridge, in a rural area. Quiet and peaceful living! . A short easy commute to Middletown, Dover, Annapolis, DC, and the beautiful beaches. Located in QA County School District. Minutes away from downtown Chestertown and Centreville.

Beds:
3
Baths:
3 Full
Sq.Ft.:
3,292
Status:
Active
MLS#:
MDKE117494
Type:
Single Family, Single Family-Detached
Subdivision:
Great Oak Estates
Lot size:
1.15 Acres
Year built:
2000
Courtesy: Coldwell Banker Realty
View additional info

Don't miss your chance to own in Great Oak Landing. Make this summer a new beginning by the Bay. Play a round on the 9-hole executive golf course or enjoy the summer heat at the pool. Ask friends to join you for a drink at The Landing Restaurant or Jellyfish Joel's Beach Bar before heading to the sandy beach for a sunset bonfire. This is the the Eastern Shore Bay life at its best, just 20 minutes from historic Chestertown and 1.5 hours from Philadelphia. Access to amenities is optional HOA. Spacious colonial with wrap around porch and all the southern charm you need. Large living room with brick fireplace and eat in kitchen with Corian Counters. Off the kitchen there's a sunroom and a separate screened porch for afternoons in. First floor also features a formal dining room, laundry room and full bath. Upstairs you'll find 2 bedrooms, a large hall bath and the master suite with private bathroom and walk in closet. The property also has a 2 car garage with extra 3rd bay perfect for storage or a hobby room.

Beds:
n/a
Baths:
Sq.Ft.:
1,286
Status:
Active
MLS#:
MDKE117436
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.07 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
View additional info

A blank canvas with strong bones... The home was taken down to the studs, beams stabilized, windows restored, Spanish Cedar front door, restored staircase restored... ENTER AT YOUR OWN RISK, INDEMNIFICATION AGREEMENT MUST BE SIGNED PRIOR TO ENTRY.

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