Chestertown Land for Sale

Chestertown Land for Sale

Welcome to Chestertown, Maryland—a charming riverside town that beautifully blends history, culture, and natural beauty. Nestled in Kent County along the banks of the Chester River, Chestertown is known for its rich colonial heritage, vibrant arts scene, and a welcoming community spirit. With its picturesque streets lined with historic homes, boutique shops, and delightful eateries, Chestertown offers a unique small-town experience that is hard to resist.

As you explore this quaint town, you’ll find a plethora of outdoor activities to enjoy. The Chester River is perfect for kayaking, sailing, and fishing, while the surrounding landscapes invite hiking and biking enthusiasts to discover the stunning natural beauty of the area. Chestertown also hosts various festivals and events throughout the year, showcasing local artisans, musicians, and the region's rich agricultural heritage.

For those looking to invest in land, Chestertown presents a unique opportunity. With available parcels of land for sale, you can create your dream home or develop a project that contributes to the town’s vibrant community. Imagine waking up to serene views and the gentle sounds of nature, all while being just a stone's throw away from the heart of a thriving town.

Whether you're seeking a peaceful retreat or a place to build a new chapter in your life, Chestertown offers the perfect backdrop. Don’t miss the chance to explore the land for sale in this enchanting corner of Maryland—where history meets opportunity and community thrives.

Newest Chestertown Land for Sale

$695,000
Rarely do vacant parcels like this become available so close to historic Chestertown! Offering approximately 43 acres, this exceptional property presents a unique opportunity to create your own private estate while enjoying outstanding recreational and hunting opportunities. The current owners have strategically developed and maintained the property for exceptional deer and turkey hunting through their partnership with HuntingPlots.com. Thoughtful habitat and land management includes established travel corridors, bedding areas, food plots, an artificial water pond, and carefully planned tree management, creating an ideal environment for wildlife. The property is subject to a Maryland Environmental Trust conservation easement; however, the easement permits the construction of one homestead, offering the opportunity to build a private residence surrounded by acreage and natural beauty. Please refer to the Kent County Health Department percolation letter and additional easement information included in the documents. Location is truly a standout feature of this rare offering. Situated within approximately 1.5 miles of downtown Chestertown, the property provides convenient access to Chester River boat ramps, Washington College, the Chester River Yacht & Country Club, shopping, dining, and all that Chestertown has to offer. Included are 3 Ten Point box deer stands, several tacticam deer cameras, and several other ladder stands. A rare combination of acreage, privacy, recreational value, and proximity to town, an exceptional opportunity on Maryland’s Upper Eastern Shore.

Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$50,000
This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.

Towhee Rd, Chestertown

Listing courtesy of The Parker Group. Contact: 3022176692
$89,000
Very private 5+ acre parcel with well and perc approved septic. Just minutes from Chestertown and very easy access to points north and south via route 301

27942 Old Morgnec Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,195,000
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.

302 S Mill St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$450,000
Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops, restaurants, waterfront activities, and all that historic Chestertown has to offer. Water and sewer hookups available. No property address has yet been assigned to the 9,381 sq ft lot; the 3,097 parcel is designated as 620 Cannon Street. Buyer to verify zoning, permitted uses, building requirements, and utility availability. Each lot is listed separately in separate listings.

Cannon St, Chestertown

Listing courtesy of Taylor Properties. Contact:

$350,000
Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops, restaurants, waterfront activities, and all that historic Chestertown has to offer. Water and sewer hookups available. The adjacent lot at the corner of Cannon and Lynchburg is also available for purchase. No property address has yet been assigned to this lot. Buyer to verify zoning, permitted uses, building requirements, and utility availability.

Cannon St, Chestertown

Listing courtesy of Taylor Properties. Contact:

$99,999
Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available. Buyer to confirm with the Town of Chestertown allowable uses and the use of the previous water/sewer allocation.

620 Cannon St, Chestertown

Listing courtesy of Taylor Properties. Contact:

$300,000
4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800
$60,000
Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

305 Roosevelt Dr, Chestertown

Listing courtesy of Taylor Properties. Contact:

$60,000
Vacant lot ready for your own choice of residence. Walking distance to the Chester River community access by boat or just enjoy the waterfront on the community deck.

233 Merganser Dr, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$75,000
Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Engineered plans are in place as well as architect plans for a 3 bedroom, 2 bath home. Buyer welcome to use these plans if it fits their needs. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land Records in Plat Book MLM liber1, Folio 391 dated 6/19/1995.

Fairlee Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$69,900
Discover the possibilities on this beautiful 4+ acre parcel. Recently surveyed, with water and sewer allocations paid, a value exceeding $16,000! This property offers a rare combination of privacy, recreation, and convenience. Whether you're seeking a peaceful retreat, hunting property, or camping getaway, this versatile parcel offers endless opportunities. Enjoy the tranquility of nature, abundant wildlife, and the privacy of a secluded setting. A small portion near the middle of the parcel is designated as non-tidal wetlands; however, it has never been observed with standing water, even after substantial rainfall.

8886 Georgetown Rd, Chestertown

Listing courtesy of Samson Properties. Contact: 4433178125
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