Land for sale in Chestertown Maryland | Page 1 of 4 | Lands of Maryland
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Land for sale in Chestertown Maryland - Page 1 of 4

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$2,395,000 65.13 acres 5 Beds | 5 Baths | 1 ½ Bath | 5800 sqft
5793 QUAKER NECK LANDING ROAD, Chestertown, MD 21620 - Kent County

65.13 acres Chestertown, MD

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.
Jonathan Ginn Meredith Fine Properties
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$7,900,000 37.23 acres
TALBOT BOULEVARD, Chestertown, MD 21620 - Kent County

37.23 acres Chestertown, MD

RADCLIFFE MEADOW - High Density zoning, 400 units - public water/sewer access - Zoned R-4, Multiple Family, 92 acres with 38 acres to be developed - 14,000' waterfront Radcliffe Creek - convenient traffic access - conveniently located to area shopping, restaurants, college and medical facilities - rails to trails - one of few developable properties in town limits of Chestertown.
Jonathan Ginn Meredith Fine Properties
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$7,900,000 37.23 acres
0 TALBOT BOULEVARD, Chestertown, MD 21620 - Kent County

37.23 acres Chestertown, MD

RADCLIFFE MEADOW - High Density zoning, 400 units - with public water/sewer access - Zoned R-4, Multiple Family, 92 acres with 38 acres to be developed - 14,000' waterfront on Radcliffe Creek - convenient traffic access - conveniently located to area shopping, restaurants, college and medical facilities - rails to trails - one of few developable properties in town limits of Chestertown.
Jonathan Ginn Meredith Fine Properties
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$285,000 0.56 acres 5 Beds | 3 Baths | 2600 sqft
816 S MEADOWVIEW DRIVE, Chestertown, MD 21620 - Kent County

0.56 acres Chestertown, MD

Exhale and enjoy a one level living lifestyle near Downtown Chestertown. With 5 bedrooms total, this home offers all pocket doors and an in-law suite with a handicap accessible master bathroom. The other side of the home sits a master bedroom w/ on-suite and 3 other bedrooms. Freshly painted, move in ready with an updated kitchen with newer stainless steel appliances, granite countertop and a large pantry. The oversized garage allows for small boat storage, ATV's or other fun toys. Bring the outdoors in with two sliders, extending the family room onto the screened porch and back yard.
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$649,000 1.7 acres 4 Beds | 4 Baths | 1 ½ Bath | 2906 sqft
509 Fey Road, Chestertown, MD 21620 - Queen Annes County

1.7 acres Chestertown, MD

Just Reduced! 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.
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$319,000 1 acres 4 Beds | 2 Baths | 2766 sqft
201 RIVER ROAD, Chestertown, MD 21620 - Queen Annes County

1 acres Chestertown, MD

Large home with great space, Den featuring a beautiful wood burning fireplace and built in shelves. There is a terrific porch overlooking the pool and the back yard. Wood floors, tiled floor in the kitchen dining room, and carpet in the enclosed porch. Two large bedrooms on the main level and 2 wonderful bedrooms upstairs. There are two baths in all. Corner lot with a sneak peek of the Chester River. There is water access at the end of the road for kayak, canoeing and enjoying the Chester River. Public marinas nearby for launching a bigger boat.
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$3,499,000 150.77 acres 7 Beds | 9 Baths | 2 ½ Baths | 9651 sqft
4845 CLIFFS CITY ROAD, Chestertown, MD 21620 - Kent County

150.77 acres Chestertown, MD

Bachelors Hope Farm, available for the first time in over 50 years, is a once-in-a-lifetime waterfront and hunting farm. The 9,600 square foot, seven bedroom Main Home is situated within feet of the Chester River. With three master suites, an in-law suite, and ample room to relax... the sweeping River views from every room are breathtaking. The 420 foot dock has eight feet MLW, water & electric, and six (or more!) slips. The large, insulated, and heated boathouse has a 150 foot private railway launch. With over 3,000 feet of River frontage and over 1,400 feet of stone revetment, the waterfront is quite literally just outside the door. Of the total 164.13 acres, 96 are tillable, 43 are wooded, and the farmland boasts three ponds. The four be
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$649,000 1.7 acres 4 Beds | 4 Baths | 1 ½ Bath | 2906 sqft
509 FEY ROAD, Chestertown, MD 21620 - Queen Annes County

1.7 acres Chestertown, MD

Just Reduced! 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.
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$589,000 0.91 acres 4 Beds | 4 Baths | 3257 sqft
7703 WATERVIEW LANE, Chestertown, MD 21620 - Kent County

0.91 acres Chestertown, MD

This magnificent residence is situated just off the 13th hole. If you like to golf, the convenience of accessing the course doesn't get much better! Expansive views over the Chester River Yacht & Country Club Golf Course to the Chester River are certainly appreciated. Two main level master suites, gourmet kit, wet bar, great room, den/bedroom, and sizeable laundry room just off of the mud-room complete the interior of the home... The breezeway connects the spacious 2-car garage with epoxy flooring, and finished 2nd level to the home, which comes in handy when the weather is not cooperating! Generous custom storage capacity & an abundance of built-ins will impress any Buyer in need of extra space. This precious gem is not going to las
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$269,000 0.92 acres 4 Beds | 2 Baths | 2352 sqft
10205 JOHN CARVILL ROAD, Chestertown, MD 21620 - Kent County

0.92 acres Chestertown, MD

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.
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$209,000 0.5 acres 3 Beds | 2 Baths | 1188 sqft
23055 OLD FAIRLEE ROAD, Chestertown, MD 21620 - Kent County

0.5 acres Chestertown, MD

One level living in Fairlee with a detached 2 car garage and workshop area. In good condition, master en suite with mostly hardwood flooring. The furnace is new and the roof was replaced in 2018. Living room, three bedrooms, eat in kitchen. Updated, well kept and turn key. Just waiting on you!
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$174,900 0.55 acres 3 Beds | 2 Baths | 1344 sqft
351 ROUND TOP ROAD, Chestertown, MD 21620 - Queen Annes County

0.55 acres Chestertown, MD

A 3 BR, 2-bath Nanticoke ranch home built just for you. Large living room made for relaxing, a couple of trees that could hold a hammock and landscaping that's close to maintenance free. Located in a water oriented community just minutes from downtown Chestertown and walking distance to Round Top Park. With low and even a possible no-down payment, there's no need to wish. Call to schedule your showing today!
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$239,000 2.01 acres 3 Beds | 2 Baths | 2437 sqft
11138 PERKINS HILL ROAD, Chestertown, MD 21620 - Kent County

2.01 acres Chestertown, MD

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.
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$3,499,000 150.77 acres 7 Beds | 9 Baths | 2 ½ Baths
4845 CLIFFS CITY ROAD, Chestertown, MD 21620 - Kent County

150.77 acres Chestertown, MD

Bachelors Hope Farm, available for the first time in over 50 years, is a once-in-a-lifetime waterfront and hunting farm. The 9,600 square foot, seven bedroom Main Home is situated within feet of the Chester River. With three master suites, an in-law suite, and ample room to relax... the sweeping River views from every room are breathtaking. The 420 foot dock has eight feet MLW, water & electric, and six (or more!) slips. The large, insulated, and heated boathouse has a 150 foot private railway launch. With over 3,000 feet of River frontage and over 1,400 feet of stone revetment, the waterfront is quite literally just outside the door. Of the total 164.13 acres, 96 are tillable, 43 are wooded, and the farmland boasts three ponds. The four be
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$270,000 0.72 acres 2 Beds | 3 Baths | 1 ½ Bath
207 BIRCH RUN ROAD, Chestertown, MD 21620 - Kent County

0.72 acres Chestertown, MD

Mile Tree Village Cape Cod home with three fireplaces, a traditional floor plan, living room, family room, screened porch, backs to woods. Home needs some updating and TLC, but it's a wonderful neighborhood. There are two bedrooms, 2 full baths, 1/2 bath, wood floors, loads of built ins both upstairs and in the family room. Within minutes to historic downtown Chestertown, but a peaceful and quiet setting. Upstairs has central air, public water and sewer. Basement has a bathroom that has been started, a fireplace, it's unfinished for the most part.
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$1,050,000 1.1 acres 4 Beds | 5 Baths | 1 ½ Bath | 4133 sqft
9326 N BAYVIEW AVENUE, Chestertown, MD 21620 - Kent County

1.1 acres Chestertown, MD

Expansive frontage on the Bay. Private, end of road lot. Large fenced pool with breathtaking bay view. House completely renovated in 2002 including infrastructure. 1st and 2nd floor Master Suites. Open den/study on second floor. Maintained steps and deck down to the water. Stone wood burning fireplace makes open living room extra cozy. Mature landscaping including vegetable garden. And of course spectacular bay views from every room. Separate artist studio and garden shed near pool. First floor master has private screened porch. Second floor master has private deck, coffee bar, gas fireplace and whirlpool bath.
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$459,900 1.01 acres 4 Beds | 3 Baths | 1 ½ Bath | 3248 sqft
7844 CHESTER COURT, Chestertown, MD 21620 - Kent County

1.01 acres Chestertown, MD

Close to Chester River Yacht & Country Club & Historic downtown Chestertown this meticulously maintained home offers office and den/library, huge owners suite w/11'ceilings, living/dining room combo w/wood floors, built-in bookcase & gas fireplace, large kitchen w/tiled floors, Silestone counters & center island. Rear screened porch & professionally landscaped. Solar panels provide energy savings!
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$538,000 1.84 acres 3 Beds | 2 Baths | 2437 sqft
5830 LANGFORD BAY ROAD, Chestertown, MD 21620 - Kent County

1.84 acres Chestertown, MD

Cozy 3 bdr waterfront home with all the natural, private surroundings the eastern shore has to offer. Very easy access to more than 300 feet of bulkheaded shoreline. 2 large detached garages to store all the waterfront toys you will need to take advantage of all Langford Creek has to provide, fishing, crabbing, year round hunting or whatever you waterfront dreams desire.
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$535,000 1.98 acres 5 Beds | 4 Baths | 1 ½ Bath | 4024 sqft
25201 FOXCHASE DRIVE, Chestertown, MD 21620 - Kent County

1.98 acres Chestertown, MD

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!!
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$589,000 2.34 acres 3 Beds | 4 Baths | 1 ½ Bath | 2745 sqft
10191 RILEYS MILL ROAD, Chestertown, MD 21620 - Kent County

2.34 acres Chestertown, MD

Very private 3 bedroom home in park like setting 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.
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$248,900 0.61 acres 3 Beds | 3 Baths | 1 ½ Bath | 1466 sqft
105 PINE COVE LANE, Chestertown, MD 21620 - Queen Annes County

0.61 acres Chestertown, MD

Immaculate Split Level Home in Pine Cove - A Water Accessible Community. 3 bed 2.5 Bath 2 Car Garage with Custom Built-in Shelving and Awesome work Table. Plant your garden in Raised Beds and Enjoy Nature. Bring your Boat and your Water Toys. Move-In READY! Minutes from Chestertown. Close to RT 301
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$459,000 2 acres 3 Beds | 4 Baths | 1 ½ Bath | 3004 sqft
8265 MOUNT PLEASANT PLANTATION LANE, Chestertown, MD 21620 - Kent County

2 acres Chestertown, MD

Sellers were transferred to another state, which is the Only reason they are selling. Originally constructed in 2000, this custom-built Yetman Builders' home has been meticulously maintained and improved over the last year: Brand new pole building, HVAC, sidewalk, wood fence, gas range, sump-pump, and professional landscaping to include Weeping Willow, Magnolia, Red Twig Dogwood, Kousa Dogwood, Dwarf Winter Berry, etc. 4 miles to Downtown Chestertown.
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$1,850,000 168.76 acres 4 Beds | 3 Baths | 1 ½ Bath
7250 PENTRIDGE LANE, Chestertown, MD 21620 - Kent County

168.76 acres Chestertown, MD

Rarely do you find a true contemporary residence in this traditional area in Kent County on Maryland's Eastern Shore. This architecturally designed house is surrounded by 168 private acres of open fields, virgin woods & ponds. The 3000 square footage includes soaring beamed ceilings, open kitchen/living area, wood floors, soap stone counters, gourmet kitchen. An exotic European style "woodstove" (far from your ordinary woodstove - see photos) dominates the outstanding design. Multiple French door & casement windows flow to a 700 sq. ft. deck & 1700 slate A& brick patio. A handsome pergola completes the design of the groundsAn exciting contemporary post & beam guest house shares the acreage and is located a private distance away. The open
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$380,000 2.22 acres 4 Beds | 3 Baths | 1 ½ Bath | 2186 sqft
8320 BEAVER COURT, Chestertown, MD 21620 - Kent County

2.22 acres Chestertown, MD

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.
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$810,000 10 acres 4 Beds | 4 Baths | 1 ½ Bath | 3128 sqft
8020 Airy Hill Rd, Chestertown, MD 21620 - Kent County

10 acres Chestertown, MD

Eastern Shore Georgian style home is situated on a serene, rural 10-acres, yet is conveniently located just 2 miles from the colonial town of Chestertown. Designed by the architect, Andrea Lombardini, and built in 2005, the thoughtfully designed interior lends an airy elegance harmoniously linking the sunlit living areas, including the first floor master suite. Taking full advantage of the pastoral views, the home showcases the finest details including random width wood floors, built-ins, high ceilings and a terrace overlooking the naturally beautiful setting. Chestertown offers a river walk, brick lined streets with 18th century homes, galleries, live theater and cafes. It enjoys a vibrant arts community, outdoor educational programs and i
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$184,900 8.83 acres
0 FAIRGALE FARM LANE, Chestertown, MD 21620 - Kent County

8.83 acres Chestertown, MD

Amazing 8.83 acre parcel located at the head waters of Fairlee Creek and in the desirable community of Fairgale! Perc approved with a cleared area for your new home. Great hunting and just enough water to launch your kayak or canoe. No HOA fees! Road has been installed to home site. Only 10 minutes to Historic Chestertown.
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$729,000 13.17 acres 5 Beds | 4 Baths | 1 ½ Bath
8601 PIPPIN HILL LANE, Chestertown, MD 21620 - Kent County

13.17 acres Chestertown, MD

AMAZING CUSTOM-BUILT ESTATE sited on almost 14 acres w/stream & Every luxury & upgrade 2500 sf basement. First floor master, 4 addtnl Brs, Phenomenal kitchen includes 3 ovens, double dishwasher, granite counters, custom Amish lighted, glass cab., custom tile floors, double sinks veg sink, conv. micro, table space, serving counter, desk area. STUNNING wall of glass & two-story brick FIREPLACE in open family room w/balcony overlook. HUGE screened porch w/vaulted ceiling & brick floor. Amazing brick front porch w/entertainment area to capture every country view! IT'S WORTH A LOOK; YOU'LL FALL IN LOVE!
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$525,000 7.86 acres
PENTRIDGE LANE, Chestertown, MD 21620 - Kent County

7.86 acres Chestertown, MD

Beautiful Eastern Shore waterfront building lot is the last available waterfront lot on Pentridge Lane in the rural community of Langford~Farm. The 7 acre lot with MLW 4~ offers a dock that is shared with one neighbor. Set on the scenic East Fork of Langford Creek, just 10 minutes from historic~Chestertown~s river walk and Washington College. Philadelphia and Washington, D.C. are 90-minutes away.
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$475,000 0.81 acres 3 Beds | 2 Baths | 1107 sqft
10864 FORESTON ROAD, Chestertown, MD 21620 - Kent County

0.81 acres Chestertown, MD

Eastern Shore waterfront retreat is privately sited on Mill Creek. Designed with cedar exterior and interior, the single floor home offers a casual ambiance with great room and large windows with water views. A new roof was installed in 2013. The dock, new deck, hot tub and floating dock invite outdoor living. Enjoy historic Chestertown with its River Walk, Washington College, shops and dining.
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$6,900,000 300 acres 5 Beds | 6 Baths | 1 ½ Bath | 10870 sqft
6798 BROAD NECK ROAD, Chestertown, MD 21620 - Kent County

300 acres Chestertown, MD

300 /- acre waterfront estate with exceptional amenities. Main house with 7,500 /- sq ft, with a retreat feel and open floor plan. Indoor and outdoor pools, high elevation and expansive southern and western views down coveted West Fork Langford Creek. Boat house with 7' .- MLW, tenant house, historic farm house, antique covered bridge, large barn, waterfowl ponds and 1.5 /- miles of shoreline.