Chestertown, MD Multifamily properties for sale

Updated: Jul 10

Mixed-Use Income Property with Retail

200204 High Street, Chestertown, MD 21620

$2,300,000

1860‑built downtown Chestertown building with 5 apartments and 3 storefronts
Renovated to the studs in 2022; since renovations, no vacancies reported
Replaced major systems in 2022: new electric service, wiring, plumbing (PEX), water and septic lines, and energy‑efficient water heaters and appliances
New windows, insulation, and air sealing; monitored fire alarm system and rebuilt foundation
Roof work includes new rear portions roof (front 50‑year cedar roof replaced in early 2000s)

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Updated: Apr 24

Updated Apartment Building in Chestertown

104 MAPLE Ave, Chestertown, MD 21620

$1,350,000

Turnkey, stabilized asset with strong fundamentals.
Well‑balanced unit mix with a 3‑bedroom and five 2‑bedroom units.
Updated units feature hardwood flooring, quartz countertops (select units), LED lighting, and in‑unit washer/dryers (most units).
Significant building‑wide improvements completed in 2019.
Located in Chestertown's historic, walkable community near downtown restaurants, waterfront, and shopping.

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Historic Chestertown Multi-Family Opportunity

349 & 351 HIGH STREET, Chestertown, MD 21620

$395,000

3,664 sqft 0.13 AC lot

Multi-family property in Chestertown's Historic and Arts & Entertainment Districts.

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Based on your search, we've compiled 11 Potential Opportunities for your consideration. Besides 3 Active listings in Chestertown, MD, we suggest exploring several alternatives: 4 properties in Nearby Cities, plus 4 Land Listings that present a potential for development.

Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Duplex Near Historic Chestertown

12712 and 12714 STILL POND Road, Still Pond, MD 21667

$549,000

4,305 sqft 0.43 AC lot

Duplex offers income potential near Chestertown and Betterton Beach.

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Duplex-Configured Residence with Split Entrances

2507 ISLAND VIEW Road, Essex, MD 21221

$565,000

2,970 sqft 0.23 AC lot

Duplex-designed home with two exterior entrances, high-end finishes, and split HVAC units throughout.

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Modern Farmhouse Duplex Opportunity

2507 ISLAND VIEW ROAD, Essex, MD 21221

$565,000

2,970 sqft 0.23 AC lot

Custom-built home with two en-suites and two exterior entrances, designed as a duplex with flexible in-law or rental potential.

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Corner Retail and Residential Income

26622 Medders Road, Still Pond, MD 21667

$425,000

7,566 sqft

Mixed-use property with a corner retail storefront and three rented apartments under separate zoning designations.

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Potential Development Sites for Consideration

Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

Central Business Zoned Development Land

107 HOWARD Street, La Plata, MD 20646

$250,000

0.23 AC lot

Central Business zoned parcel with plans for a three-story mixed-use building and 15 parking spaces.

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Turnkey Camping Property in Horntown

354-355* SEA BASS DR lot: 2Lots, Horntown, VA 23395

$163,500

0.16 AC lot

High-end camping with access to numerous amenities.

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Lot Near Crabbing Pier

WALLOPS DRIVE lot: 153, Horntown, VA 23395

$57,500

0.09 AC lot

Residential lot with septic and water view in Horntown.

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Land Near Shepherd University

8285 MARTINSBURG Pike, Shepherdstown, WV 25443

$650,000

3.70 AC lot

Prime land near Shepherd University with development potential.

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Chestertown, MD Multifamily Properties Market Trends and Statistics

Explore 3 multifamily properties for sale in Chestertown, MD, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 3,664 square feet of properties for sale, with an estimated market value of $4,045,000.

Sale prices for multifamily properties in Chestertown, MD start at $395,000, averaging $1,348,333, and reaching up to $2,300,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

Neighborhood	Average Price
21620	$1.4M

Neighborhood

Average Price

21620

$1.4M