Real Estate

Real Estate and Homes for Sale in Chestertown, MD

(1 - 15 of 92)
  1. An elegant new offering located on the Chester River in Quaker Neck, just south of Historic Chestertown. This magnificent family residence has it all: ideal waterfrontwildlife habitat, a private pier w/ 3ft MLW, marvelous panoramic southern water ...
    Christopher Mcclary ·Over 4 weeks ago on RealtyWW
  2. Custom built house on the East Fork of Langford Creek set on 8+ acres with a private dock. This is the first time the house has been for sale; original owners. It was built by Patrick Jones and designed by architects Dunning & Dunning from Swathmo...
    Over 4 weeks ago on ListedBuy
  3. Smith-ringgold house. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort. Originally a merchant’s home in the heart of historic Chestertown, the Smith-Ringgold house has been modified repr...
    Nancy McD McGuire ·Over 4 weeks ago on ListedBuy
  4. Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road, cr...
    Retha Arrabal ·4 weeks ago on RealtyWW
  5. Over 13 acres at the corner of routes 213291 in Chestertown. High traffic count intersection. Per MDOT, current Annual Average Daily Traffic is 14, 710. Zoned RB Professional Office. Located within 1 hour of Annapolis and Wilmington. 90 minutes to...
    Courtney Chipouras ·Over 4 weeks ago on RealtyWW
  6. Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away....
    Over 4 weeks ago on ListedBuy
  7. This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht andCountry Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The la...
    Lisa Raffetto ·2 days ago on RealtyWW
  8. Outstanding Waterfront property, with excellent deer, turkey, and waterfowl hunting with two impoundment ponds, an irrigation well, and 4.5 +/- tillable acres, on 9.75 acres nestled along Phillips Creek. The restored and renovated farmhouse featur...
    Richard Evans ·Over 4 weeks ago on RealtyWW
  9. Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. The Sultana model is an exquisite four-bedroom, two-and-a-half-bath home that offers luxurious living and breathtaking views of the C...
    Kaitlyn Cole Collins Benson & Mangold ·Over 4 weeks ago on Kaitlyn Cole Collins Benson & Mangold (via ListedBuy)
  10. Welcome to the former historic HILLTOP HOTEL! A charming estate which underwent significant renovations in 2021 while preserving many of the original characteristics the home has to offer. This property is unlike any other - offering historic char...
    Over 4 weeks ago on ListedBuy
  11. Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Ne...
    Over 4 weeks ago on ListedBuy
  12. (Pics are from a prior listing. New pics on the way) Escape to the Country! This home is perfect for the outdoor enthusiast. Bring the horses, dogs, chickens, hunters, hobbyist,...you name it. 15 acres, with small pond and open areas for your anim...
    Tom Boeshore ·Over 4 weeks ago on RealtyWW
  13. Quaint, historic home in Great Oak Landing with tons of character. Double front doors and double parlors. Randon width 18th-century floors. Sunroom and screened-in porch. 2 gas fireplaces. Fenced-in yard, gorgeous gardens with pond, deck, and bric...
    Lisa P Raffetto ·Over 4 weeks ago on ListedBuy
  14. Modern Cape Cod style home in peaceful Orchard Hill sitting on 1.89 acres. Interior boasts vaulted ceilings, ground floor primary bedroom , upgraded kitchen offering granite counter tops, quality stainless appliances, island with gas cooktop and b...
    Kenneth Roderick ·Over 4 weeks ago on RealtyWW
  15. 33.6 ACRES....approx 1.5 acre open field fronting Airy Hill Road with an entrance to the rear of property offering another open area of approx 1 acre with remaining land beyond that being wooded with inclusion of a pond that owner states is approx...
    Debbie Meikle ·Over 4 weeks ago on RealtyWW
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