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Chesapeake City Homes for Sale

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Chesapeake City Homes for Sale

Welcome to Chesapeake City, Maryland—a picturesque gem nestled in Cecil County that perfectly embodies the charm of small-town living while offering a vibrant community spirit. Known for its stunning waterfront views along the Chesapeake and Delaware Canal, this quaint town is steeped in history and brimming with natural beauty. With its quaint streets lined with unique shops, delightful eateries, and historic homes, Chesapeake City invites you to experience a lifestyle that is both relaxed and enriching.

The heart of Chesapeake City is its thriving waterfront, where you can enjoy leisurely strolls along the canal, take in breathtaking sunsets, or indulge in outdoor activities like kayaking and fishing. This tight-knit community hosts various events throughout the year, including festivals, farmers' markets, and art shows, making it easy to connect with neighbors and create lifelong memories.

For those considering a move to this enchanting town, there are a variety of homes for sale that cater to diverse tastes and lifestyles. From charming historic homes that echo the town's rich heritage to modern properties that offer contemporary comforts, Chesapeake City has something for everyone. Whether you’re looking for a cozy cottage with waterfront access or a spacious family home in a peaceful neighborhood, you’ll find a perfect fit here.

With its blend of history, natural beauty, and a warm community atmosphere, Chesapeake City is not just a place to live—it’s a place to thrive. Come explore the homes for sale and discover your dream home in this delightful corner of Maryland!

Newest Chesapeake City Homes for Sale

82 Woodside Dr, Chesapeake City image
82 Woodside Dr, Chesapeake City $459,000

Welcome to 82 Woodside Drive, a beautifully maintained 5-year-old Colonial situated on a .34-acre lot in the desirable water-oriented community of Elk River Basin in Ches...

  • 4 Beds
  • 3 Baths
Courtesy of Coldwell Banker Chesapeake Real Estate Company

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

904 Biddle St, Chesapeake City image
904 Biddle St, Chesapeake City $799,000

There's no place like home when you live along the Chesapeake & Delaware Canal, offering wide water views, natural light, and peaceful surroundings. Set on a spacious lo...

  • 3 Beds
  • 3 Baths
Courtesy of Integrity Real Estate

Listing courtesy of Integrity Real Estate. Contact:

416 Mitton Rd, Chesapeake City image
416 Mitton Rd, Chesapeake City $6,750,000

Unicorn Farm includes two parcels, #022095 and #007967. Total acreage is 393.346. Set on a picturesque landscape, this exceptional working equestrian estate offers a r...

  • 4 Beds
  • 4 Baths
Courtesy of Patterson-Schwartz - Greenville

Listing courtesy of Patterson-Schwartz - Greenville. Contact: 3024294500

2871 Augustine Herman Hwy, Chesapeake City image
2871 Augustine Herman Hwy, Chesapeake City $298,000

Purchase includes Map 48(Tax ID 0802004771), Parcels 80, 74 (Tax ID 0802004712) and 84 (Tax ID 0802013525) Total of 2.81 acres

  • 2 Beds
  • 1 Baths
Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. Contact:

240 Randalia Rd, Chesapeake City image
240 Randalia Rd, Chesapeake City $885,000

Set on 15.11 acres in the peaceful countryside of Chesapeake City, this distinctive property offers the space, privacy, and versatility that are increasingly hard to find...

  • 3 Beds
  • 3 Baths
Courtesy of Keller Williams Realty

Listing courtesy of Keller Williams Realty. Contact: (302) 360-0300

2418 Old Telegraph Rd, Chesapeake City image
2418 Old Telegraph Rd, Chesapeake City $795,000 ▼

Welcome to 2418 Old Telegraph Rd, Chesapeake City Maryland. The home is a car enthusiasts dream with an attached 2 car garage and oversized detached garage with finished ...

  • 4 Beds
  • 4 Baths
Courtesy of Berkshire Hathaway HomeServices PenFed Realty

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

244 Cherry St, Chesapeake City image
244 Cherry St, Chesapeake City $95,000

Own a Piece of Chesapeake City History Step into the past with this truly one-of-a-kind property, originally built as an early 1900s church and rich with architectural...

  • 99 Beds
  • 99 Baths
Courtesy of Patterson-Schwartz-Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact: 3022855100

246 Biddle St, Chesapeake City image
246 Biddle St, Chesapeake City $699,999

There’s no place like home at 246 Biddle Street, a Victorian home full of Chesapeake City history and classic craftsmanship. Believed to have been built by master carpent...

  • 4 Beds
  • 4 Baths
Courtesy of Integrity Real Estate

Listing courtesy of Integrity Real Estate. Contact:

320 Cecil St, Chesapeake City image
320 Cecil St, Chesapeake City $305,000 ▼

NEW PRICE! Folk Victorian home, featuring gingerbread trim and over 2000 sq ft., offers a versatile layout ideal for everyday living and entertaining. Spacious kitchen a...

  • 3 Beds
  • 2 Baths
Courtesy of Long & Foster Real Estate, Inc.

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 879-8080

943 Cayots Corner Rd, Chesapeake City image
943 Cayots Corner Rd, Chesapeake City $109,999 ▼

needs work sold as is

  • 3 Beds
  • 1 Baths
Courtesy of Thurston Wyatt Real Estate, LLC

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact: 4103206785

1455 Cayots Corner Rd, Chesapeake City image
1455 Cayots Corner Rd, Chesapeake City $19,900,000 ▼

Rarely… does such a unique, well-designed, constructed, and maintained world-class equestrian facility grace the international real estate market. Spanning 510 preserved ...

  • 4 Beds
  • 5 Baths
Courtesy of Monument Sotheby's International Realty

Listing courtesy of Monument Sotheby's International Realty. Contact: 3026546500

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