Chestertown Homes with Trees/Woods View

Chestertown Homes with Trees/Woods View

Welcome to Chestertown, Maryland—a charming riverside town that perfectly blends history, nature, and a vibrant community spirit. Nestled along the banks of the Chester River, Chestertown is renowned for its picturesque streets, historic architecture, and rich cultural heritage. As one of Maryland's oldest towns, founded in 1706, it boasts a delightful array of boutiques, art galleries, and eateries that celebrate local flavors and craftsmanship.

One of the most enchanting aspects of Chestertown is its abundant natural beauty. Imagine waking up to the gentle rustle of leaves and the serene sights of towering trees and lush woods right outside your window. Homes with trees and woods views in this idyllic town offer a unique opportunity to immerse yourself in nature while enjoying the comforts of modern living. Whether you prefer cozy cottages or spacious family homes, many properties in Chestertown are thoughtfully designed to maximize the stunning vistas of the surrounding greenery.

The community here is close-knit and welcoming, hosting events like the annual Chestertown Tea Party Festival and the renowned Washington College’s Riverfront Concert Series. With its vibrant arts scene, rich history, and stunning landscapes, Chestertown is not just a place to live; it’s a lifestyle choice that embraces the beauty of nature and the warmth of community.

If you're seeking a home that harmonizes with nature, Chestertown’s tree-lined streets and wooded views provide a perfect backdrop for your next chapter. Come explore the charm of this delightful town, where every day feels like a breath of fresh air.

Newest Chestertown Homes with Trees/Woods View

$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:

$885,000
5 Beds ⋅ 4 Baths
Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

7680 Country Club Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. 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:

$135,000
Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still being just 9 minutes from Historic Chestertown. Convenient access to Routes 213 and 544 makes travel to Centreville, Easton, and Middletown easy. Quotes are already available for septic installation, well installation, and clearing of the existing structure and brush.

109 2nd St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$15,000
Half acre+ secluded wooded lot. There used to be a house on the property but county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot and there is a 16' right of way to access. Buyer to do any due diligence. Could be a great hunting property surrounded by woods and farmland!

22681 Wood Yard Ln, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$813,900
3 Beds ⋅ 4 Baths
**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

104 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$839,500
3 Beds ⋅ 3 Baths
**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

102 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$320,000
3 Beds ⋅ 2 Baths
Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$10,000
Build Your Dream Home on Two Expansive Lots in Chesapeake Landing! 15,000 SQFT of prime land combining Lots 191 & 192 on the south side of Clarissa Road, Block 2 of Chesapeake Landing, all under one tax ID. This is a rare opportunity to design and build your custom home in a sought-after community where nearby homes are selling in the high $600Ks! Enjoy the charm of Chestertown living, just minutes from Historic Downtown Chestertown, the scenic Chesapeake Bay, and Washington College. Conveniently close to local parks, restaurants, and waterfront amenities, this location combines tranquility with accessibility. Don’t miss this incredible chance to secure your lot and bring your dream home to life. Opportunities like this don’t come often—act now and make your vision a reality!

Clarissa Rd, Chestertown

Listing courtesy of Samson Properties. Contact: (703) 378-8810
$60,000
Back on the market due to buyer's failure to perform. Due diligence was done with the County as far as hooking up to the septic system but verify with Kent County Public Works. The corners have been marked and survey is in the documents tab. E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Loads of opportunities for a private wooded oasis. Located about 15 minutes from Chestertown or Rock Hall.

Georgetown Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$150,000

Caulks Field Road, Chestertown

Listing courtesy of RE/MAX Allegiance. Contact:

$150,000
Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty. Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and the beautiful Chester River, which flows right through Chestertown. Whether you're looking for a peaceful retreat or a place to create your forever home, this is an opportunity you don’t want to miss!

Georgetown Rd Se, Chestertown

Listing courtesy of RE/MAX Allegiance. Contact:

Start Your Search