Recently Sold Homes in Caroline County, MD

130 homes

Sort:

Recommended

SOLD JUL 16, 2026

ABOUT THIS HOME
Recently Sold Home in Caroline County, MD:
Price Reduction! Well built and lovingly maintained by the original owner. This 3 bedroom, 2 bath rancher featuring oak floors, central air, a brick fireplace and is situated on 1 acre. This home is conveniently located and move in ready. A new roof was installed in 2024. Nice open yard with established shade trees around the house. Three season porch for casual entertaining or enjoying a crab feast with family and friends. Small barn with cement floor at rear of the property.

$290,000 Last sold price

3 beds2 baths1,642 sq ft

4215 Preston Rd, Preston, MD 21655

(410) 479-2000

SOLD AUG 7, 2026

ABOUT THIS HOME
Recently Sold Home 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, new 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 guest spac

$335,000 Last sold price

4 beds2 baths2,076 sq ft

4305 Langrell Rd, Preston, MD 21655

(443) 274-1900

SOLD AUG 14, 2026

ABOUT THIS HOME
Recently Sold Home in Caroline County, MD:
Welcome to 102 Lister Lane in Ridgely, MD! This spacious, 4 bedroom 3 full bath home offers plenty of room for you to spread out with a functional layout designed for everyday living. The main level even includes an office and the upper level an open loft area. The unfinished basement offers endless possibilities for additional living space, such as a home gym, workshop, or just plain storage space. While ready for your personal cosmetic touches, this home is a fantastic opportunity to build some sweat equity while making it your very own. Conveniently located in the desirable Lister Estates Community you can enjoy the perfect blend of small town charm with easy access to near by shopping,

$367,000 Last sold price

4 beds3 baths2,612 sq ft

102 Lister Ln, Ridgely, MD 21660

(410) 255-3690

SOLD JUL 31, 2026

ABOUT THIS HOME
Recently Sold Home in Caroline County, MD:
Welcome to 109 Briarwood Cir in the sought-after Sandy Meadows community of Denton, offering an impressive blend of space, comfort, and flexibility with over 3,300 finished square feet plus an additional 1,525 sq ft unfinished walkout basement ready for your future vision. With its stately two-story presence, beautiful architectural windows, mature landscaping, and inviting curb appeal, this home makes a memorable first impression before you even step inside. From the moment you enter, natural light pours through the front entry and oversized windows into the sun-filled two-story foyer accented with decorative molding and elegant details. Fresh paint, new carpet, and hardwood flooring creat

$410,000 Last sold price

4 beds3.5 baths3,372 sq ft

109 Briarwood Cir, Denton, MD 21629

(410) 729-7700

SOLD JUN 29, 2026

ABOUT THIS HOME
Recently Sold Home in Caroline County, MD:
Set on a private, wooded 1.37± acre lot in Harmony Woods, this beautifully maintained home offers a warm, inviting layout with abundant natural light and thoughtful updates throughout. A welcoming front porch leads into the main level with hardwood floors, detailed trim work, and easy flow from the kitchen and breakfast area to the living room with a wood-burning fireplace. Full-view doors open to a spacious screened-in porch and adjoining deck overlooking the fenced backyard and mature trees. The spacious first-floor primary suite includes direct access to the screened porch, a private primary bathroom with two granite-topped vanities, a jetted soaking tub, a tiled walk-in shower,

$533,900 Last sold price

4 beds2.5 baths3,442 sq ft

5585 Harmony Woods Dr, Preston, MD 21655

(410) 770-9255

Property at 1308 Chesapeake Dr, Denton, MD 21629, 3 beds, 2 baths

$319,000 Last sold price

3 beds2 baths1,460 sq ft

1308 Chesapeake Dr, Denton, MD 21629

(302) 360-0300

Property at 12136 Holly Rd, Ridgely, MD 21660, 4 beds, 3 baths

$750,000 Last sold price

4 beds3 baths2,432 sq ft

12136 Holly Rd, Ridgely, MD 21660

(410) 543-4545

Property at 1309 Fairfield Ct, Denton, MD 21629, 3 beds, 2.5 baths

$345,000 Last sold price

3 beds2.5 baths1,360 sq ft

1309 Fairfield Ct, Denton, MD 21629

(410) 255-3690

Property at 6326 Statum Rd, Preston, MD 21655, 3 beds, 2 baths

$375,000 Last sold price

3 beds2 baths1,344 sq ft

6326 Statum Rd, Preston, MD 21655

(410) 224-2200

Property at 1507 Blue Heron Dr, Denton, MD 21629, 3 beds, 2.5 baths

$185,000 Last sold price

3 beds2.5 baths1,860 sq ft

1507 Blue Heron Dr, Denton, MD 21629

(410) 271-1265

Property at 23283 Magnolia Hills Rd, Denton, MD 21629, 3 beds, 2 baths

$435,000 Last sold price

3 beds2 baths2,044 sq ft

23283 Magnolia Hills Rd, Denton, MD 21629

(410) 304-2250

Property at 24254 Mallow Dr, Preston, MD 21655, 3 beds, 2 baths

$399,000 Last sold price

3 beds2 baths1,650 sq ft

24254 Mallow Dr, Preston, MD 21655

(410) 643-4663

Property at 7805 Dyer Rd, Denton, MD 21629, 3 beds, 2.5 baths

$950,000 Last sold price

3 beds2.5 baths1,800 sq ft

7805 Dyer Rd, Denton, MD 21629

(302) 539-0800

Property at 7837 Shore Dr, Preston, MD 21655, 4 beds, 2.5 baths

$474,000 Last sold price

4 beds2.5 baths1,920 sq ft

7837 Shore Dr, Preston, MD 21655

(410) 822-1415

Property at 24383 Robins Creek Rd, Preston, MD 21655, 4 beds, 2 baths

$360,000 Last sold price

4 beds2 baths1,568 sq ft

24383 Robins Creek Rd, Preston, MD 21655

(410) 770-3600

Property at 28035 Possum Hill Rd, Federalsburg, MD 21632, 4 beds, 30 baths

$82,000 Last sold price

4 beds30 baths1,428 sq ft

28035 Possum Hill Rd, Federalsburg, MD 21632

(703) 538-1113

Property at 5 7th St, Ridgely, MD 21660, 3 beds, 1 bath

$295,000 Last sold price

3 beds1 bath1,024 sq ft

5 7th St, Ridgely, MD 21660

(410) 479-3993

Property at 12397 Ridgely Rd, Ridgely, MD 21660, 2 beds, 2 baths

$435,000 Last sold price

2 beds2 baths1,952 sq ft

12397 Ridgely Rd, Ridgely, MD 21660

(410) 224-2200

Property at 4 Maple Ave, Ridgely, MD 21660, 2 beds, 1 bath

$250,000 Last sold price

2 beds1 bath864 sq ft

4 Maple Ave, Ridgely, MD 21660

(443) 274-1900

Property at 13023 Mason Branch Rd, Ridgely, MD 21660, 3 beds, 3 baths

$344,000 Last sold price

3 beds3 baths2,030 sq ft

13023 Mason Branch Rd, Ridgely, MD 21660

(410) 822-6665

Property at 12 N Maple Ave, Ridgely, MD 21660, 2 beds, 1 bath

$272,500 Last sold price

2 beds1 bath1,056 sq ft

12 N Maple Ave, Ridgely, MD 21660

(410) 822-9000

Property at 11231 River Rd, Ridgely, MD 21660, 3 beds, 2 baths

$395,000 Last sold price

3 beds2 baths1,600 sq ft

11231 River Rd, Ridgely, MD 21660

(410) 479-4663

Property at 12658 Oakland, Ridgely, MD 21660, 4 beds, 2 baths

$380,000 Last sold price

4 beds2 baths1,692 sq ft

12658 Oakland, Ridgely, MD 21660

(410) 758-0333

Property at 12104 Holly Rd, Ridgely, MD 21660, 3 beds, 2 baths

$557,500 Last sold price

3 beds2 baths1,568 sq ft

12104 Holly Rd, Ridgely, MD 21660

(410) 745-8060

Property at 24872 Meeting House Rd, Denton, MD 21629, 3 beds, 1 bath

$180,000 Last sold price

3 beds1 bath1,763 sq ft

24872 Meeting House Rd, Denton, MD 21629

(703) 378-8810

Property at 316 Liberty Rd, Federalsburg, MD 21632, 1 bed, 1 bath

$90,000 Last sold price

1 bed1 bath692 sq ft

316 Liberty Rd, Federalsburg, MD 21632

(410) 754-7000

Property at 27311 Patricia Ct, Federalsburg, MD 21632, 3 beds, 1.5 baths

$239,000 Last sold price

3 beds1.5 baths1,248 sq ft

27311 Patricia Ct, Federalsburg, MD 21632

(410) 543-4545

Property at 311 Maple Ave, Federalsburg, MD 21632, 3 beds, 2 baths

$260,000 Last sold price

3 beds2 baths1,500 sq ft

311 Maple Ave, Federalsburg, MD 21632

(410) 543-4545

Property at 112 Vernon Ave, Federalsburg, MD 21632, 2 beds, 2 baths

$205,000 Last sold price

2 beds2 baths884 sq ft

112 Vernon Ave, Federalsburg, MD 21632

(410) 255-3690

Property at 121 E Central Ave, Federalsburg, MD 21632, 4 beds, 2 baths

$230,000 Last sold price

4 beds2 baths2,320 sq ft

121 E Central Ave, Federalsburg, MD 21632

(302) 856-1458

Property at 3410 Seaman Rd, Preston, MD 21655, 3 beds, 2.5 baths

$549,000 Last sold price

3 beds2.5 baths1,988 sq ft

3410 Seaman Rd, Preston, MD 21655

(410) 479-3993

Property at 313 Holt St, Federalsburg, MD 21632, 3 beds, 2 baths

$225,000 Last sold price

3 beds2 baths1,008 sq ft

313 Holt St, Federalsburg, MD 21632

(240) 793-2485

Property at 302 Vernon Ave, Federalsburg, MD 21632, 3 beds, 1 bath

$230,000 Last sold price

3 beds1 bath1,252 sq ft

302 Vernon Ave, Federalsburg, MD 21632

(410) 822-1415

Property at 21579 Tanyard Rd, Preston, MD 21655, 4 beds, 2 baths

$235,000 Last sold price

4 beds2 baths1,816 sq ft

21579 Tanyard Rd, Preston, MD 21655

(410) 822-6665

Property at 21134 Dover Bridge Rd, Preston, MD 21655, 3 beds, 2 baths

$275,000 Last sold price

3 beds2 baths1,586 sq ft

21134 Dover Bridge Rd, Preston, MD 21655

(410) 770-9255

Property at 6101 Bethlehem Rd, Preston, MD 21655, 3 beds, 1 bath

$295,000 Last sold price

3 beds1 bath1,392 sq ft

6101 Bethlehem Rd, Preston, MD 21655

(410) 479-0777

Property at 128 Main St, Preston, MD 21655, 3 beds, 2.5 baths

$435,000 Last sold price

3 beds2.5 baths2,839 sq ft

128 Main St, Preston, MD 21655

(410) 304-2250

Property at 4669 Gadow Rd Unit `, Preston, MD 21655, 2 beds, 1 bath

$60,000 Last sold price

2 beds1 bath904 sq ft

4669 Gadow Rd Unit `, Preston, MD 21655

(410) 479-3993

Property at 4310 Bethlehem Rd, Preston, MD 21655, 2 beds, 1 bath

$130,500 Last sold price

2 beds1 bath696 sq ft

4310 Bethlehem Rd, Preston, MD 21655

(410) 770-9255

Property at 3675 Seaman Rd, Preston, MD 21655, 3 beds, 2 baths

$245,000 Last sold price

3 beds2 baths1,787 sq ft

3675 Seaman Rd, Preston, MD 21655

(410) 479-2000

Property at 5026 Bethlehem Rd, Preston, MD 21655, 3 beds, 2 baths

$285,000 Last sold price

3 beds2 baths1,922 sq ft

5026 Bethlehem Rd, Preston, MD 21655

(410) 479-3993

Viewing page 1 of 4

Recently Sold Homes in Caroline County

There are currently 130 recently sold homes for sale in Caroline County at a median listing price of $337K. 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 77 days and receive 2 offers. This map is refreshed with the newest listings in Caroline County every 15 minutes.

In the past month, 27 homes have been sold in Caroline County. In addition to houses in Caroline County, there was also 1 condo, 12 townhouses, and 2 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.

More real estate resources for Caroline County, MD

Nearby Counties

Cities

Nearby Counties with Recently Sold Homes

More to explore in Caroline County, MD

How to buy a house in Caroline County, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.