Chesapeake City Real Estate

Welcome to Chesapeake City, Maryland, a quaint and picturesque town nestled in the heart of Cecil County. This charming community, with its rich history and scenic waterfront views, offers a unique blend of small-town charm and modern amenities that makes it an ideal place to call home.

Founded in the early 19th century, Chesapeake City is steeped in history, with beautifully preserved architecture that tells the story of its past. Stroll down the tree-lined streets and admire the stunning Victorian homes, many of which have been lovingly restored. The town's historic district is a treasure trove of quaint shops, delightful eateries, and local art galleries, providing a perfect backdrop for leisurely afternoons.

One of the highlights of Chesapeake City is its stunning location along the Chesapeake and Delaware Canal. The waterfront offers a range of outdoor activities, from boating and fishing to scenic walking trails that showcase the area’s natural beauty. The town's parks provide ample space for picnics, playdates, and community events, fostering a strong sense of belonging among residents.

Chesapeake City is also known for its vibrant community spirit, hosting numerous events throughout the year, including the popular annual Canal Day Festival. With a friendly atmosphere and a close-knit community, this town is perfect for families, retirees, and anyone seeking a peaceful lifestyle.

If you're looking for a place where history meets modern living, Chesapeake City is the perfect choice. Discover your dream home in this enchanting town and experience the warmth and charm that make Chesapeake City a true gem in Maryland.

Newest Listings in Chesapeake City

14 Buddy Blvd, Chesapeake City $115,000

Welcome to your new three bedroom 2 bath home located in Chesapeake Estates. This well maintained with recent added roofs and an additional parking space that makes thre...

3 Beds
2 Baths

Courtesy of Real-Trust-Associates, LLC.

Listing courtesy of Real-Trust-Associates, LLC.. Contact: (443) 553-2206

966 Biddle St, Chesapeake City $399,999

Take advantage of this opportunity to build your dream home on the breath taking 1.6 acre lot. This property features views of the canal and is just minutes from the his...

Courtesy of Patterson-Schwartz-Middletown

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

Lot 5 Old Telegraph Rd, Chesapeake City image

Lot 5 Old Telegraph Rd, Chesapeake City $229,900

Discover your dream home location with this private and serene 4.6-acre wooded lot. Nestled among other wooded properties and situated across from a picturesque tree nurs...

Courtesy of Patterson-Schwartz-Brandywine

Listing courtesy of Patterson-Schwartz-Brandywine. Contact: 3024750800

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

42 Lamborn Ln, Chesapeake City $299,900

Rare opportunity to own a 7.42 acre parcel in Chesapeake City, MD! Just a short drive to downtown Chesapeake City and Middletown, DE! Currently, a mobile home is located ...

3 Beds
1 Baths

Courtesy of RE/MAX Chesapeake

Listing courtesy of RE/MAX Chesapeake. Contact:

Chestnut Springs Rd, Chesapeake City image

Chestnut Springs Rd, Chesapeake City $399,000

OVER 10.5 ACRES FOR SALE OFF CHESTNUT SPRINGS RD, LAKE ON THE PROPERTY, LAND IS UNDEVELOPED, HAS LOTS OF DIFFERENT POTENTIALS

Courtesy of RE/MAX Distinctive Real Estate, Inc.

Listing courtesy of RE/MAX Distinctive Real Estate, Inc.. Contact: 3019660035

34 Buddy Blvd, Chesapeake City $90,000 ▼

Wonderfully landscaped and spacious 3 bedroom 2 bathroom handicap-accessible manufactured home in Chesapeake Estates! Upon entry up the front ramp, you'll notice the love...

3 Beds
2 Baths

Courtesy of RE/MAX Chesapeake

Listing courtesy of RE/MAX Chesapeake. Contact:

904 Biddle St, Chesapeake City $824,904

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:

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:

344 Cayots Corner Rd, Chesapeake City image

344 Cayots Corner Rd, Chesapeake City $249,000 ▼

Welcome Home To Your 3 Bedroom Chesapeake City Rancher Located Just Outside Of Town, Peaceful Country Setting Among Sprawling Horse Farms . The Bohemia School District An...

3 Beds
1 Baths

Courtesy of Key Realty, Incorporated

Listing courtesy of Key Realty, Incorporated. Contact:

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