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200 High St
For Sale $2,300,000
$2,300,000
- Units
- Unknown Sq Ft
- 6,098 Sq Ft
- Unknown Cap Rate
Description
A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and since renovations has had no vacancies, with solid leases in place. During the renovations every major system in the building was replaced. Upgrades include new electric service, meters and new wiring throughout, all new plumbing using PEX, new energy efficient water heaters and appliances, rebuilt foundation, new Jeldwen Auralast windows, insulation and air sealing, new roof on rear portions of building (front cedar roof was replaced in early 2000s), new water and sewer lines and rear egress, a monitored fire alarm system and much more.
Two of the storefronts are rented to a local arts non-profit and a yoga and pilates studio will be moving into the third commercial space in April. The 5 apartments consist of two 2-bedroom units and three 1-bedroom apartments. The steady income stream from the units is complemented by a generous property tax credit through 2032 (buyer to verify transferability). The property also has a Limited Lead-Free certificate, which requires only an exterior visual inspection every two years, and exempts the owner from MDE registration requirements. Complete income and expense information available after signing a confidentiality agreement. Limited photos posted for tenants' privacy.
Contact for a private tour today. Please do not disrupt the businesses, they are tenants and the businesses are not part of the sale.
Amenities
Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt
Property Details
| List Price | $2,300,000 |
| Property Type | Multi-Family |
| Usable Sqft | Unknown |
| Number of Stories | 0 stories |
| Parking Spots | 0 spots |
| Year Built | 1860 |
| Last Sold | Unknown |
| Sold Price | Unknown |
| APN # | 1504008952 |
| MLS # | MDKE2006092 |
| Property ID | 294413836 |
| Lot Sqft | 6,098 |
| Zoning | C2 |
| Days on Market | 27 |
| Original List Price | Unknown |
| Date Updated | February 03, 2026 |
| Date Created | January 28, 2026 |
| Unit # | Beds | Baths | Current Rent | Proforma Rent |
| Unit #1 | $84,000 | $0 |
Listing Provided By
Julie H SANTOBONI an agent of . Lic #672033
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Data last updated: February 24, 2026.
Contact Agent
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Robert Crawford
REAL ESTATE AGENT