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Chestertown MD Real Estate & Homes for Sale

119 Properties Found


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1–25 of 119 properties displayed
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Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9758157
Type:
Single Family-Detached
Subdivision:
N/A
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 & new baths, while retaining the Victorian signatures of high ceilings, spacious rooms, fine wood floors, detailed wood trim, long windows, arched halls & graceful staircase. Rear & side gardens, 2 car detached garage with wine room & potting shed at the end of this Water St. driveway.

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9917072
Type:
Single Family-Detached
Subdivision:
N/A
Lot size:
0.22 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This Beaux Art house is European/Mediterranean with a splash of Spanish influence; on the Chester River; in Historic Chestertown. Huge front hall, enormous Great room, River room, attached heated Spa & garden room + skylights. Large Master, sitting room & master bath. 2 car attached garage. Double lot. Enjoy the river from inside or on the Terrace. Unique house in the heart of a special town.

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9801884
Type:
Single Family-Detached
Subdivision:
N/A
Lot size:
0.06 Acres
Year built:
1760
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

The Banning House; Exceptional & unusual circa 1760. Much attention paid to preserving original features while bringing the house into 21st century comforts and amenities. Double front porches, off street parking, rear fenced patio & accompanying Ice House ,Rear sunroom, Glimpse of the Chester River. Walk to coffee, shops, restaurants, river & Washington College; all charm & no traffic.

Beds:
3
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10055156
Type:
Single Family-Attached
Subdivision:
N/A
Lot size:
0.05 Acres
Year built:
1999
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Affordable Chestertown town house with 1st floor bedroom overlooking Wilmer Park and the Chester River,located in town, near shops or restaurants. Nice rear patio or sit on the front porch and watch the boating. Marina near by for your boat. Inside Family room has wood burning fireplace, skylights,raised ceiling & opens to a screened porch overlooking the patio complete with pavers.

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10067650
Type:
Single Family-Detached
Subdivision:
BYFORD HEIGHTS
Lot size:
0.36 Acres
Year built:
1974
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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One floor living in this brick rancher in Byford Heights. Close enough for a winter water glimpse, but far enough from the river that flood insurance is not needed. Just a few blocks to Washington College and the heart of Chestertown. Excellent flow for entertaining and easy living.

Beds:
5
Baths:
5.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9662196
Type:
Single Family-Detached
Subdivision:
CHESTERTOWN
Lot size:
65.13 Acres
Year built:
1970
Courtesy: Meredith Fine Properties
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The Kentfields Farm-A country Estate for all seasons - Kentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful Eastern Shore. This 65 acre estate on Jarrett Creek, just off the Chester River and Chesapeake Bay. The home provides a comfortable Eastern Shore lifestyle. A unique living/sporting/entertaining property.

Beds:
5
Baths:
5.00
Sq.Ft.:
4,748
Status:
Active
MLS#:
KE9934443
Type:
Single Family-Detached
Subdivision:
QUAKER NECK
Lot size:
42.07 Acres
Year built:
1800
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Quintessential Eastern Shore Waterfront Farm is set on 42-acres with 690 ft. of water frontage and long views of Langford Creek. Inviting tree-lined drive leads to the lovely, well-maintained home, c.1800. Property features rip-rap shoreline, 33-tillable acres, outbuildings and garage. Enjoy the local wildlife, hunting or water activities. Adjacent 11-acre private waterfront lot is also available.

Beds:
5
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9588584
Type:
Single Family-Detached
Subdivision:
POMONA
Lot size:
113 Acres
Year built:
1810
Courtesy: Cross Street Realtors LLC
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Magnificent 113 Acre Waterfront Farm with a Three-Bay Two-Story Brick Colonial built in 1810 near Historic Chestertown. 97.9 acres tillable, 13.9 acres in Conservation Reserve Program and 1 acre Wildlife Habitat Incentives Program - Impoundment. 1 Deep Water Pond. Tilling rights under lease for 2016 growing season.

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10056028
Type:
Single Family-Detached
Subdivision:
SARAH SKIPPER LANDS
Lot size:
0.61 Acres
Year built:
1995
Courtesy: The Hogans Agency
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Located across the river from Historic Chestertown, this private, well landscaped, Dutch Colonial is the perfect getaway! Entertain with ease with the spacious open first floor and french doors leading to the waterfront deck, patio, pool, and hot tub. Sit out on the balcony from any of the 3 adjoining bedrooms and enjoy the views the Chester River has to offer - there is something for everyone!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,940
Status:
Active
MLS#:
KE10055129
Type:
Single Family-Detached
Subdivision:
LANGFORD FARM
Lot size:
2.45 Acres
Year built:
1997
Courtesy: Cross Street Realtors LLC
View additional info

Extraordinary Waterfront WITH Pool Permit! Gourmet kitchen for the culinary artist, well-appointed detail throughout - from heated flooring to imported Mexican tile. 2 screened porches coupled w/ expansive views to the waterfront invite the outdoor tranquility into the residence. The highly efficient mechanics and systems will impress the energy conscious "smart home" buyer.

Beds:
5
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9795358
Type:
Single Family-Detached
Subdivision:
LANGFORD FARM
Lot size:
4.42 Acres
Year built:
1998
Courtesy: Cross Street Realtors LLC
View additional info

An exquisite custom built home w/ incredible architectural detail! Reclaimed VT barn hardwood floors; 1st floor master w/ luxurious ensuite bath & walk-in closets; gourmet kitchen; sweeping river views from almost every room; pier w/ boat lift, floating dock & 4+ MLW depth; 3 bay garage w/ breezeway; whole-house backup generator; too many more to list! Private, but only 10 min to Downtown!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,778
Status:
Active
MLS#:
KE10075510
Type:
Single Family-Detached
Subdivision:
CHANTILLY FARM
Lot size:
30.45 Acres
Year built:
1955
Courtesy: TTR Sotheby's International Realty
View additional info

SPECTACULAR VIEWS FROM THIS 30 ACRE ESTATE ON THE CHESAPEAKE BAY WITH 1000 ft OF SHORE LINE AND GRADUAL SLOPE TO WATER, SANDY BEACH, GUEST COTTAGE, WINE CELLAR IN LARGE BASEMENT, 3 CAR GARAGE, GENERATOR, UNLIMITED WILDLIFE AND BEAUTY EVERYWHERE! FRESH WATER POND, TROMBE WALL, PASSIVE SOLAR BUILDING DESIGN IN FAMILY ROOM. HOUSE AND PROPERTY HAVE BEEN IMMACULATELY MAINTAINED.

Beds:
5
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10005230
Type:
Single Family-Detached
Subdivision:
LANGFORD FARM
Lot size:
3.43 Acres
Year built:
1994
Courtesy: Doug Ashley Realtors, LLC
View additional info

Very nice home on the East Fork, Langford Creek. There is a dock with 3+ MLW, w/ electric/water at the dock. Swimming pool, covered deck, mature trees, beautiful yard. Open floor plan inside with living room, family room with fireplace, updated kitchen. Fresh paint, wood floors, new carpet upstairs, 1st floor suite, Water views from most rooms of the home. Nice waterfront!

Beds:
5
Baths:
4.00
Sq.Ft.:
4,866
Status:
Active
MLS#:
KE9898545
Type:
Single Family-Detached
Subdivision:
GREAT OAK
Lot size:
1.36 Acres
Year built:
1997
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Chesapeake Bay waterfront residence with 150~ of rip rap shoreline boasts breathtaking panoramas from most every room. Custom built 5-bedroom home offers a family room, living room, study, gourmet kitchen, casual dining space as well as a formal dining room, and temperature controlled wine cellar. Located in community of Great Oak, just 15 minutes from historic Chestertown and Washington College.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,086
Status:
Active
MLS#:
KE9777301
Type:
Single Family-Detached
Subdivision:
HISTORIC CHESTERTOWN
Lot size:
0.28 Acres
Year built:
1788
Courtesy: Maryland Heritage Properties
View additional info

Fine landmark property rarely available. Brick w all refinements of 1788 c. maintained w great care. Grand stair hall flows to all social rooms. Perfect "stage" for fine collections. Quiet setting in Chestertown Hist. Dist. Handsome glass sunporch overlooks private garden & 3car garage wi climatized room + workshop/garden area & large open studio/office. Immediate to River/shops/Arts/live theatre.

Open House:

Saturday, 10/28 12:00-2:00PM

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10004714
Type:
Single Family-Detached
Subdivision:
SARAH SKIPPER LANDS
Lot size:
0.85 Acres
Year built:
1964
Courtesy: Doug Ashley Realtors, LLC
View additional info

Sweeping views of the Chester River can be experienced from most rooms in this exquisitely renovated Contemporary home! Updates in past 7 years include new HVAC, new roof, new kitchen, new master bath, new 2nd bath, new Trex deck and more! The open floor plan is perfect for formal or casual entertaining. 95'+/- dock with 3'+/- MLW. No flood insurance! Across the river from Historic Chestertown.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,257
Status:
Active
MLS#:
KE9980579
Type:
Single Family-Detached
Subdivision:
COUNTRY CLUB ESTATES
Lot size:
0.92 Acres
Year built:
1969
Courtesy: Cross Street Realtors LLC
View additional info

If your golf game had as much attention to detail as this stunning country club home, you'd be a Pro! Situated just off the 13th hole, this timeless design radiates both elegance & comfort while expansive views over the course to the Chester River relax the soul. 2 master suites, gourmet kit, wet bar, great room, library, apartment, generous/custom storage capacity & an abundance of built-ins...

Beds:
4
Baths:
5.00
Sq.Ft.:
2,800
Status:
NEW LISTING
MLS#:
KE10086646
Type:
Single Family-Detached
Subdivision:
SCOTT'S POINT
Year built:
2008
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous Townhouse in desirable Scott's Point. Great waterviews of the Chester River & Wilmer Park. 2 deeded boat slips. Open Floor plan is enhanced by beautiful wood floors and cabinets. Wonderful Gormet Kitchen opens to dining and living area. Balconies on each floor. First Floor Den options as bedroom. Large open airy rooms gives simple elegance with light. Walkable to everything downtown!

Beds:
3
Baths:
3.00
Sq.Ft.:
3,300
Status:
Active
MLS#:
QA9842553
Type:
Single Family-Detached
Subdivision:
PHEASANT
Lot size:
20 Acres
Year built:
2002
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.

Beds:
6
Baths:
6.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9950177
Type:
Single Family-Detached
Subdivision:
HISTORIC CHESTERTOWN
Lot size:
1.15 Acres
Year built:
1860
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

The John L Stam House, circa 1860, is a beautifully restored Gothic Revival Victorian. Currently run as a B&B there are 4 guest rooms with full baths and an additional 2 BR in the owners quarters. The first floor features original faux painted fireplaces, hand painted plastered ceilings, and "Jenny Doors" leading to a gracious veranda. A recently added water feature enhances the beautiful gardens

Beds:
5
Baths:
4.00
Sq.Ft.:
5,200
Status:
Active
MLS#:
KE9930010
Type:
Single Family-Detached
Subdivision:
GSM INDUSTRIES
Lot size:
1 Acres
Year built:
2000
Courtesy: Doug Ashley Realtors, LLC
View additional info

Stunning 5BR, 3.5BA custom Georgian residence perfect for relaxing & entertaining. Close to Town/Marina/Country Club. Designer molding details, open kitchen w/granite/stainless app, built in Media cabinet, widow's walk w/water view, huge screened porch overlooks lush backyard. Custom carved fireplace. Hardwood floors. French doors. Italian rose marble foyer and dining rm. Agent owner.

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10000453
Type:
Single Family-Detached
Subdivision:
ROYSTON SHORES
Lot size:
0.43 Acres
Year built:
1986
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Enjoy all the Chester River has to offer from this beautiful waterfront home. Two levels of decks and screened in porch overlook the dock and farmland beyond. The house has many recent upgrades including new kitchen,cork floors and systems. Master bedroom is on first floor with two huge bedrooms upstairs. Sit back and relax in the family room facing the water and watch the abundant wildlife.

Beds:
5
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9600471
Type:
Single Family-Detached
Subdivision:
HISTORIC CHESTERTOWN
Lot size:
0.42 Acres
Year built:
1877
Courtesy: Benson & Mangold, LLC
View additional info

A beautiful 1877c Victorian home in the heart of historic Chestertown. Currently operating as a B & B, this exemplary primary residence, welcomes you and your family. Offering a separate carriage house, two car garage, beautiful gardens & add'l lot., w/ ample parking. A short walk to the Chester River, Washington College, restaurants, shops and farmers market. Turn-Key business available.

Beds:
5
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10011782
Type:
Single Family-Detached
Subdivision:
TOLCHESTER ESTATES
Lot size:
0.89 Acres
Year built:
1952
Courtesy: RE/MAX First Choice
View additional info

Welcome to Castle Point! This 3,100+ square foot home features 5 huge bedrooms, 3.5 baths, tons of natural lights, water views from every angle, multiple private balconies, and rec room. Master bathroom boasts a huge soaking tub, ceramic shower with bench and dual shower heads both with relaxing water views. Spend your evenings sitting around your stone fire pit on your private slice of heaven!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,496
Status:
Active
MLS#:
KE9927220
Type:
Single Family-Detached
Subdivision:
DOWNTOWN CHESTERTOWN
Lot size:
0.03 Acres
Year built:
1735
Courtesy: Cross Street Realtors LLC
View additional info

Historically certified Buck Bacchus House reverently restored. This iconic house has offered its residents a perfect setting for quiet and relaxing times as well as enchanting dinner parties in its' candlelit dining room. The chef of the house has the option of a beautifully crafted galley kitchen, authentic cooking fireplace in living room or the outside grill. The attention to detail says it all

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.