Homes with Basements for Sale in Caroline County, MD

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COMING SOON

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
Welcome to 24712 Tribbett Circle — a beautifully appointed 2016-built home set on 2.43 pristine acres in one of Ridgely’s most desirable neighborhoods. This luxurious 4-bedroom, 4-bathroom property seamlessly blends timeless style with modern comfort, offering an exceptional living experience both inside and out. The main level is adorned with rich bamboo flooring, creating a warm and sophisticated ambiance throughout. At the heart of the home, the spacious and thoughtfully updated kitchen features abundant cabinetry, premium finishes, and an intuitive layout ideal for everyday living as well as elevated entertaining. Its open design enhances natural light and promotes a seamles

$629,900

4 beds4 baths3,491 sq ft

24712 Tribbett Cir, Ridgely, MD 21660

2.43 acre lot • 2 garage spots • Built 2016

(410) 546-3211

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
Welcome to this beautifully updated rancher that checks every box — and then some. Sitting on over half an acre, this home blends modern upgrades, spacious living, and incredible functionality, all wrapped into the perfect Eastern Shore retreat. Step inside to find new LVP floors, fresh siding, and a brand-new roof, giving the home a crisp, clean, move-in-ready feel. The heart of the home is the large family room, featuring soaring vaulted ceilings that flood the space with natural light and make every gathering feel special. With 4 generous bedrooms plus a dedicated office, this home offers the flexibility and layout today’s buyers need, whether you work from home, need extra g

$399,000

4 beds2 baths2,076 sq ft

4305 Langrell Rd, Preston, MD 21655

0.59 acre lot • 2 garage spots • Built 1963

(443) 274-1900

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
This property is full of character, rare to find beautiful pine paneling in its natural state. With Built-in book shelves and hard wood flooring under the carpets original to the house. A spare room on the first floor could be used as a 4th bedroom . The basement has room for expansion as well. The back deck is great for entertaining or just enjoying the view. Solid house making this appealing to home buyers and investors. This was just recently a rental property and met all requirements.

$219,000

3 beds1 bath1,350 sq ft

115 Boyce Mill Rd, Greensboro, MD 21639

Hard wood flooring • Back deck • Room for expansion

(410) 479-0777

$440,000

4 beds3 baths3,212 sq ft

21405 Tanyard Rd, Preston, MD 21655

3.29 acre lot • Built 1974 • Listed 22 days

(301) 970-2447

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
Experience timeless elegance and Eastern Shore charm at this beautifully restored 4-bedroom, 3.5-bath colonial retreat set on 7 acres along the Choptank River. Once known as “Hazelwood, ” this historic Governor’s Mansion is one you don’t want to miss! Inside, you’ll find expansive formal and informal rooms flow seamlessly for entertaining and family living alike. This estate features refinished wood floors (2023), freshly replastered / painted walls (2023), updated marble bathrooms, brand new gas stove (2025), HVAC split systems (2019), roof (2016), septic (2009), well (2013), pool liner (2020), and a new propane tank and pool heater (2022) for the in-ground po

$1,295,000

4 beds3.5 baths4,496 sq ft

24800 Pealiquor Rd, Denton, MD 21629

Backyard dock • In ground pool • Tranquil water views

(304) 645-7700

Property at 4 S 1st St S, Denton, MD 21629, 3 beds, 3 baths

$699,000

3 beds3 baths2,756 sq ft

4 S 1st St S, Denton, MD 21629

(410) 479-4663

Property at 5 Lister Ln, Ridgely, MD 21660, 4 beds, 2.5 baths

$429,500

4 beds2.5 baths2,692 sq ft

5 Lister Ln, Ridgely, MD 21660

(301) 261-9700

Property at 12618 Knife Box Rd, Greensboro, MD 21639, 3 beds, 2 baths

$797,500

3 beds2 baths2,342 sq ft

12618 Knife Box Rd, Greensboro, MD 21639

(410) 479-0777

Property at 8 W Liberty St, Ridgely, MD 21660, 5 beds, 2 baths

$429,900

5 beds2 baths4,060 sq ft

8 W Liberty St, Ridgely, MD 21660

(410) 479-3993

Property at 21948 Main St, Hillsboro, MD 21641, 3 beds, 1 bath

$189,900

3 beds1 bath1,904 sq ft

21948 Main St, Hillsboro, MD 21641

(410) 479-3993

Property at 1010 S 2nd St, Denton, MD 21629, 3 beds, 2 baths

$365,900

3 beds2 baths1,588 sq ft

1010 S 2nd St, Denton, MD 21629

(410) 643-4663

Property at 208 Main St, Federalsburg, MD 21632, 4 beds, 1.5 baths

$150,000

4 beds1.5 baths2,668 sq ft

208 Main St, Federalsburg, MD 21632

(410) 754-7000

Property at 24766 Tribbett Cir, Ridgely, MD 21660, 4 beds, 2.5 baths

$595,000

4 beds2.5 baths3,168 sq ft

24766 Tribbett Cir, Ridgely, MD 21660

Property at 14271 Cedar Ln, Greensboro, MD 21639, 6 beds, 3 baths

$1,475,000

6 beds3 baths3,756 sq ft

14271 Cedar Ln, Greensboro, MD 21639

(443) 292-6767

Property at 27279 Jenny Hye Ln, Marydel, MD 21649, 3 beds, 2.5 baths

$355,000

3 beds2.5 baths2,286 sq ft

27279 Jenny Hye Ln, Marydel, MD 21649

(410) 690-7356

Property at 22005 Main St, Hillsboro, MD 21641, 3 beds, 3 baths

$545,000

3 beds3 baths3,088 sq ft

22005 Main St, Hillsboro, MD 21641

(410) 778-9319

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Nearby homes that match your criteria

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
Discover the potential of this beautiful 1 acre property, perfectly positioned among open farmland and just one minute from Route 301. The existing home offers 4 bedrooms, 2 baths, and 2,160 sq ft above grade, plus a full 1,400 sq ft basement. While the house requires major renovation, and may be best suited for a tear down, the property itself provides a solid foundation with an existing well and septic already in place. Whether you’re looking to rebuild, restore, or reimagine, the possibilities here are truly endless.

$120,000

4 beds2 baths2,160 sq ft

1040 Price Station Rd, Church Hill, MD 21623

1.01 acre lot • Built 1929 • Listed 2 days

(410) 220-4648

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
If you’ve been looking for a home you can truly make your own, this is the opportunity. This property offers a large, open floor plan with all the square footage and layout you’ve been wanting. It simply needs the right buyer to bring it back to life. Inside, you’ll find a dedicated office, a formal dining room, and an expansive kitchen and family room that make everyday living and entertaining effortless. Upstairs, all 4 bedrooms are generously sized, including a massive primary suite complete with a large bathroom and a huge walk-in closet. The full basement offers even more potential — whether you envision a rec room, gym, theater, or additional living space, it&r

$425,000

4 beds2.5 baths2,597 sq ft

143 Long Creek Way, Centreville, MD 21617

0.23 acre lot • 2 garage spots • Built 2012

(443) 274-1900

OPEN DEC 6, 11AM TO 1PM

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a . 345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic dining space, and a large all-seasons room off the kitchen—perfect for gatherings or relaxing year-round. The full basement offers a blank slate, ready to finish as a recreation room, workshop, or extra storage. A brand-new septic system provides peace of mind, while the attached two-ca

$399,000

3 beds2.5 baths2,034 sq ft

121 Primrose Rd, Chestertown, MD 21620

0.34 acre lot • 2 garage spots • Built 1971

(410) 778-0330

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
Renovated 3-story townhouse-style condo that feels brand new! Updates include luxury vinyl plank flooring on the main level, new carpet upstairs, replacement windows, a stunning kitchen with quartz countertops, new cabinetry, deep sink and stainless appliances. On the main level rounding out the appliance package is a brand new Maytag washer and dryer. Enjoy 3 spacious bedrooms, 2.5 baths, and a large rear deck overlooking open space. The one-car garage provides additional parking for up to three vehicles total. You’ll find ample shopping nearby—Target, BJ’s, Dick’s Sporting Goods, Aldi, Harris Teeter, and more—along with a wide variety of dining options such a

$295,000

3 beds2.5 baths1,568 sq ft

29595 Dutchmans Ln #602, Easton, MD 21601

$200 HOA • Garage • Built 1989

(410) 822-6272

COMING SOON

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
Welcome to 530 Kennersley Farm Lane, nestled in the private waterfront community of Kennersley Farm. Set on 5 private acres along Island Creek, this property offers lots of privacy and nature. A long, tree-lined driveway leads you past mature landscaping and ample parking, where you can see views of the water. Inside, there is beautiful flooring and a bright, open layout. The kitchen features granite countertops, a center island, upgraded GE Profile appliances, and an eat-in area overlooking the in-ground pool and Island Creek. The primary suite, located on the first floor, is a true retreat with a huge walk-in closet, featuring a soaking tub, dual granite vanity, and tile shower. This roo

$978,500

5 beds3 baths2,352 sq ft

530 Kennersley Farm Ln, Church Hill, MD 21623

5 acre lot • 2 garage spots • Pool

(717) 735-8400

ABOUT THIS HOME
Home with Basement for sale in Caroline County, MD:
Nestled in the charming subdivision of Centerville, this exquisite Colonial-style residence offers a harmonious blend of elegance and comfort, perfect for those seeking a refined lifestyle. Built in 2013, this detached home boasts a generous 2,454 square feet of thoughtfully designed living space, ensuring ample room for relaxation and entertainment. As you step inside, you are greeted by a warm and inviting atmosphere. Natural light pours in through large windows, enhancing the inviting ambiance and showcasing the home's sophisticated design. The gourmet kitchen is a culinary enthusiast's dream, featuring high-end appliances and ample counter space, making meal preparation a delight. Wheth

$629,000

3 beds2.5 baths2,454 sq ft

217 Austin, Centreville, MD 21617

1 acre lot • Built 2013 • Listed 24 days

(410) 647-8000

Property at 116 Pasture Ct, Centreville, MD 21617, 4 beds, 2.5 baths

$714,900

4 beds2.5 baths— sq ft

116 Pasture Ct, Centreville, MD 21617

(410) 729-7700

Property at 8658 Camac St, Easton, MD 21601, 4 beds, 4 baths

$545,000

4 beds4 baths3,594 sq ft

8658 Camac St, Easton, MD 21601

(410) 224-2200

Property at 29798 Captain Adamouski St, Easton, MD 21601, 4 beds, 3.5 baths

$509,000

4 beds3.5 baths4,304 sq ft

29798 Captain Adamouski St, Easton, MD 21601

(410) 822-6272

Property at 9134 Honeysuckle Dr, Easton, MD 21601, 3 beds, 1.5 baths

$349,900

3 beds1.5 baths2,200 sq ft

9134 Honeysuckle Dr, Easton, MD 21601

(410) 822-6665

Property at 415 Twin Meadows Farm Ln, Centreville, MD 21617, 4 beds, 2.5 baths

$779,900

4 beds2.5 baths— sq ft

415 Twin Meadows Farm Ln, Centreville, MD 21617

(410) 729-7700

Property at 126 Finley Creek Dr, Centreville, MD 21617, 5 beds, 2.5 baths

$849,000

5 beds2.5 baths2,993 sq ft

126 Finley Creek Dr, Centreville, MD 21617

(443) 496-4040

Property at 331 Kidwell Ave, Centreville, MD 21617, 5 beds, 2.5 baths

$579,000

5 beds2.5 baths2,718 sq ft

331 Kidwell Ave, Centreville, MD 21617

(301) 970-2447

Property at 7287 Shirley Dr, Easton, MD 21601, 4 beds, 2.5 baths

$355,000

4 beds2.5 baths2,200 sq ft

7287 Shirley Dr, Easton, MD 21601

(410) 479-3993

Property at 309 S Main St, Hurlock, MD 21643, 6 beds, 2 baths

$225,000

6 beds2 baths6,970 sq ft

309 S Main St, Hurlock, MD 21643

(410) 220-5745

Property at 325 Twin Meadows Farm Ln, Centreville, MD 21617, 4 beds, 2.5 baths

$764,900

4 beds2.5 baths2,500 sq ft

325 Twin Meadows Farm Ln, Centreville, MD 21617

(410) 729-7700

Property at 515 N Kent St, Chestertown, MD 21620, 4 beds, 2 baths

$499,900

4 beds2 baths2,220 sq ft

515 N Kent St, Chestertown, MD 21620

(410) 778-3779

Property at 104 Pasture Ct, Centreville, MD 21617, 4 beds, 4 baths

$964,607

4 beds4 baths— sq ft

104 Pasture Ct, Centreville, MD 21617

(410) 729-7700

Property at 834 Willow Grove Rd, Felton, DE 19943, 4 beds, 3 baths

$477,000

4 beds3 baths2,200 sq ft

834 Willow Grove Rd, Felton, DE 19943

(302) 677-0020

Property at 7347 Shirley Dr, Easton, MD 21601, 5 beds, 2 baths

$389,000

5 beds2 baths2,344 sq ft

7347 Shirley Dr, Easton, MD 21601

(410) 822-1415

Homes with Basements for Sale in Caroline County

There are currently 16 homes with basements for sale in Caroline County at a median listing price of $320K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Caroline County stay on the market for 58 days and receive 2 offers. This map is refreshed with the newest listings in Caroline County every 15 minutes.

In the past month, 33 homes have been sold in Caroline County. In addition to houses in Caroline County, there was also 1 condo, 4 townhouses, and 4 multi-family units for sale in Caroline County last month. Find your dream home in Caroline County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Caroline County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Caroline County. If you're looking to sell your home in the Caroline County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Caroline County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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