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Chestertown Condos for Sale

Welcome to Chestertown, Maryland – a hidden gem nestled along the banks of the Chester River in Kent County. This charming town, rich in history and natural beauty, offers a vibrant blend of small-town charm and modern conveniences. With its picturesque streets lined with beautifully preserved 18th-century buildings, Chestertown is a hub for art, culture, and community. Residents and visitors alike enjoy the lively atmosphere created by local galleries, boutiques, and cafes, as well as the annual events that celebrate the town's heritage, such as the Chestertown Tea Party Festival.

For those seeking a serene yet engaging lifestyle, our selection of condos for sale in Chestertown presents an exceptional opportunity. These modern residences are designed for comfort and convenience, featuring spacious layouts, contemporary finishes, and stunning views of the surrounding landscape. Many condos are located within walking distance to the vibrant downtown area, allowing you to easily explore local shops, restaurants, and the scenic waterfront.

Imagine sipping your morning coffee on your private balcony, taking in the peaceful ambiance of the river, or enjoying a leisurely stroll through the historic district. With a strong sense of community and a commitment to preserving its rich heritage, Chestertown is not just a place to live; it's a place to thrive. Whether you're a first-time homebuyer, a retiree looking for a peaceful retreat, or an investor seeking a promising property, Chestertown's condos offer a unique blend of lifestyle and opportunity. Come discover your new home in this delightful town!

Newest Chestertown Condos for Sale

105 N Water St Unit #3, Chestertown image
105 N Water St Unit #3, Chestertown $489,000

Second story, waterfront condo in historic Chestertown. Private boat slip. Many more details and pictures to come. Stay tuned! You won't want to miss this!

  • 2 Beds
  • 2 Baths
Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

117 N Water St Unit #3B, Chestertown image
117 N Water St Unit #3B, Chestertown $295,000

Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with...

  • 1 Beds
  • 1 Baths
Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

117 Water St N Unit #2B, Chestertown image
117 Water St N Unit #2B, Chestertown $350,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

  • 1 Beds
  • 1 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

117 Water St N Unit #2A, Chestertown image
117 Water St N Unit #2A, Chestertown $375,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

  • 2 Beds
  • 1 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

117 Water St N Unit #1B, Chestertown image
117 Water St N Unit #1B, Chestertown $200,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

  • 1 Beds
  • 1 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

117 Water St N Unit #1A, Chestertown image
117 Water St N Unit #1A, Chestertown $685,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

  • 3 Beds
  • 3 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

117 Water St N Unit #1A, 1B, 2A, & 2B, Chestertown image
117 Water St N Unit #1A, 1B, 2A, & 2B, Chestertown $1,500,000 ▼

**Listing price is for FOUR units for sale as an investment package! 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a ...

  • 7 Beds
  • 5 Baths
Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

#37 Landing Ln, Chestertown image
#37 Landing Ln, Chestertown $765,900

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The h...

  • 3 Beds
  • 3 Baths
Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. Contact:

#25 Landing Ln, Chestertown image
#25 Landing Ln, Chestertown $1,099,900

**To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms an...

  • 4 Beds
  • 4 Baths
Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. Contact:

Little Harbor Way Unit #1, Chestertown image
Little Harbor Way Unit #1, Chestertown $1,459,000

**To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The h...

  • 3 Beds
  • 3 Baths
Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. Contact:

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