Poplar Avenue

Status: SOLD

Address: 8687 Poplar Avenue Chestertown, MD 21620

A must see charming renovation in a private setting! This fully updated home features 3 bedrooms, 2 full bathrooms, hardwood and ceramic tile floors, efficient geothermal HVAC, a new roof, hardiplank siding, and a detached garage. Improved with an inside/outside home stereo system, horseshoe pit, and an outdoor shower, this home great for entertainment. Located within walking distance to Tolchester Marina and the Shanty Tiki Bar, this move in condition property is the perfect full time residence or weekend getaway. The sale includes 3 neighboring lots for a total of .459 acre to secure the private setting.


Chestertown Office Building

Status: SOLD

Address:  500 Washington Ave, Chestertown, MD 21620

0.52 acres

Office building conveniently located in high traffic area on route 213 in Chestertown. Near Washington College, hospital, shopping, and downtown. Building features large reception area and 3, private offices. Newer heat pump/ac. Zoning is Institutional. See Town of Chestertown ordinance for approved and conditional uses.

110 S Kent Street Chestertown MD
French Door Entry 110 S
Kitchen 110 S Kent ST
Entry 110 S Kent ST
Stairs Entry 110 S Kent ST
110 S Kent Street Chestertown MD
Stairs Entry 110 S Kent ST
Patio Yard 110 S Kent Street MD


Chestertown Colonial

Status: SOLD

Address:  110 S. Kent ST, Chestertown, MD 21620

This Historical home has undergone a tasteful renovation to include 3 bedrooms, 2 full bathrooms, new plumbing and HVAC. Home offers an open floor plan with decorative touches which include wide plank pine floors, shiplap, original doors with hardware and original mouldings. The courtyard garden with brick patio and walkway lead to Downtown, waterfront, shops and restaurants. Bike trails and park for your enjoyment are nearby. The delightful, turnkey home blends history with
comfort and convenience.

Centreville Home on 2+ Acres

Status: SOLD

Address: 325 Brownsville Road, Centreville, MD 21658

A well maintained home with lots of character! Located on 2+ acres just outside of Centreville this home features hardwood floors throughout, updated kitchen with custom cabinets and granite counters, updated HVAC, and a full basement. The stone driveway is large enough to store multiple cars, boats or an RV. A detached garage/shop site is present with water and electric.

Gibson's Grant


Status: SOLD

Address: 178 Evelyne St, Chester, MD 21619

Better than new in desirable Gibson's Grant. Designer kitchen w/ large island, double wall oven & cooktop opens to family room w/ gas fireplace. Hardwoods abound. Large master suite. Tons of storage. Spectacular finishes. Community features fitness center, clubhouse, pool, & pier. Located on Cross Island Trail. Minutes from Bay Bridge. Easy commute to Annapolis/DC/Baltimore. 

Main Street Galena

102 Main Street, Galena


Status: SOLD

Solid home in the heart of Galena. Residence has wood floors, 3 bedrooms, a screened porch and two car garage! Priced to sell.

Waterfront Cottage


Status: SOLD

Address: 214 Front Street, Crumpton, MD 21628

Perfect Waterfront Retreat! This ideal cottage getaway is situated on a rip-rapped shore of the upper Chester River offering expansive views and access to navigable water. Property features include a 1.23 acre lot with 165+/- feet of Chester River frontage, a two bedroom cottage with exceptional water views, several outbuildings, easy access to major highways, and a deep water boat launch just down the street! Fairly priced at $349,900.

Chestertown Condo


Status: SOLD

Address: 105 Water Street #4

Sold in 44 days! Bright and delightful waterfront condo in the Heart of Chestertown’s Historic District! Move in condition with 2 bd, 2ba, cheerful kitchen/family room overlooking the river, wood floors, fireplace and cozy waterfront porch. Second floor unit includes private boat slip at your back door. Short scenic stroll to quaint shops, restaurants, farmer’s market, and Washington College.

Chestertown Bungalow


Status: SOLD

Address: 206 Philosopher's Terrace, Chestertown, MD 21620

Sold in 13 days for 96% asking price! A cute Chestertown bungalow on a large lot with plenty of space! This charming house features hardwood floors, a screen porch, spacious kitchen and a partial basement. The large upstairs bedrooms offer lots of closet space and natural light. The property is in a great location next to Washington College and within walking distance to Downtown Chestertown.

413 High Street, Chestertown, MD 21620


Status: SOLD

4BR 4.5BA Renovated house on High Street. Hardwood floors throughout with and updated kitchen, high ceilings, a screen porch and two car garage. Master suite features a huge walkin closet, full updated bath and a roof top deck.

13950 Huyett Lane, Galena, MD 21635


Status: SOLD

Custom cedar home on over 4.5 acres with 2 car detached garage with storage above. This custom home features an open floor plan with cathedral ceilings, wide plank wood floors, deluxe custom kitchen with wet bar, rear deck, and full walk out basement. Close to Marinas and restaurants.

1253 Philosopher's Terrace, Chestertown


Status: SOLD

4 bedroom 3.5 bathroom Chestertown Residence. Open floor plan with wood floors, 2 gas fireplaces and large deck. Minimal maintenance!

8373 Broad Neck Road

8373 Broad Neck Road


Status: SOLD

3 bedroom, 2 bath residence on 4 acres close to Chestertown! Property needs minor cosmetic repairs, but priced to sell! SOLD IN 13 DAYS!

Residential - Mallard Road


Status: SOLD

2 bedroom 2.5 bath brick home on 7.8 acres. Property has 5 acres of marsh on the Chester River. 

Residential - 103, 1st Ave., Betterton


Status: SOLD

Charming 3 bedroom 1 bath cottage in Betterton. Cottage has hardwood floors, front porch and views of the Chesapeake Bay.

Residential - 106 1/2 Water Street


Status: SOLD

Unique Downtown Chestertown Residence with pine wood floors, built in bookshelves, an elevator,  slate patio and 2 car garage. One of a kind property  with great privacy! Sold in 93 Days!

Residential - Trustee Street, Still Pond


Status: SOLD

Newly renovated in 2017 this 3 bedroom 1.5 bath residence has a large kitchen, new appliances, large detached garage and country views. Sold in 21 Days!

Residential - 114 High Street


Status: SOLD

Great Investment in desirable Downtown Chestertown! 3 unit multi family residence fully occupied and low vacancy rate. Sold in 69 Days! 

Image coming soon!

Residential - River Road


Status: SOLD

3 bedroom 2.5 Bath Residence on River Road. Property has wood floors, 2 car garage, and views of the Chester River. 

Residential - Lands End Road


Status: SOLD

Marvelous Chester River Waterfront! This custom home has hardwood floords, large updated kitchen and complete privacy. Sold in 3 Days!

8373 Broad Neck Road

Residential - Broad Neck Road


Status: SOLD

Solid brick home with wood floors, large shop and spacious yard. Close proximity to Chestertown. Sold in 10 Days!

Residential - Collins Avenue


Status: SOLD

Brick home in Country Club Estates. This home is move in ready after a tasteful remodel. New kitchen, hardwood floors, brick porch and limited water views!