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listing
1 of 77
Single FamilyFor Sale
$4,850,000
23620 Lands End Road
Chestertown, MD 21620
Listed by: Cross Street Realtors LLC, 4434803453
MLS: Bright MLS
5Beds
6Full2Half Baths
9,852Sq Ft
Est. Mortgage
$25,135/mo

80 private acres beautifully situated on the highly prized Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. One of only 4 properties on Orchard Point and sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to add a modern house inspired by Maryland's historic heritage. The residence succeeds as a home for family comfort, entertaining, relaxing, gardening, hunting, fishing, birding and appreciating wildlife. Its east/west orientation highlights sunrises and sunsets that can be enjoyed from every room in the house. A real retreat. The five bedroom and 7 fireplace (woodburning) home was designed with 12-foot ceilings on the first floor to accentuate the views and the light. A main floor primary suite includes two separate en-suite dressing rooms and bathrooms along with a wood burning fireplace. The second floor has four bedrooms, three with fireplaces, and all with en-suite bathrooms. One bedroom has a separate sitting room. A wide hall runs along the width of the house providing access to all of the rooms. The property features the landscape design of acclaimed D.C. based Oehme, van Sweden. Hardscapes and plantings were strategically orchestrated and include a walled garden filled with flowering trees and shrubs along with a sweep of peonies in the spring. Three ponds invite active wildlife, including a beautiful blue heron. The farm fields are being organically farmed by a neighboring farmer. Two structures in the garden provide a relaxing reading or meditation venue. Bluestone and brick terraces along the entire river facing side of the house lead to a pool and pool pagoda. The property is uniquely designed to capture the feeling of the land while being welcoming and inviting to all who live there or visit. It has been lived in and loved by the original owner for over two decades. Caretaker house with barns and silo are situated at upper end (entry) of property. 50 acres under crop are farmed organically (as are all area farms) and rented to local farmer. Family hunting and fishing are exceptional. Rock Fish is plentiful. The main residence has recently benefited from a new cedar shake roof and updated energy efficient French doors and windows throughout. The unfinished basement is approx. 2900 square feet with 9' ceilings, inviting the next steward to introduce additional lifestyle enhancements. Less than 10 miles to downtown Chestertown, with its restaurants, coffee shops, food stores, bookstore and vibrant music and art scene, this property combines riverfront tranquility with easy access to town. Additional FAQ: 2013-caretaker house built; 2020 small pond redesigned and landscaped; 2021 new cedar shake roof installed, copper gutters and downspouts repaired as needed; 2022 all windows and French doors on main level replaced with top of line Anderson product- trim removed, replaced and painted; 3 lintels in walled garden replaced with black walnut; 2024 resurfaced entire lane from Lands End Road to main residence; all windows and French doors on 2nd level replaced; farm buildings by tenant house painted. Property access is prohibited without a scheduled showing.

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This data is up-to-date as of 08/17/2025 06:51 AM. Listing provided by Richard Keaveney of Cross Street Realtors LLC.
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