Recently Sold Homes in Caroline County, MD

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SOLD OCT 22, 2025

ABOUT THIS HOME
Recently Sold Home in Caroline County, MD:
Historic charm meets endless potential in this spacious corner-lot home in the heart of downtown Denton—formerly home to the beloved local flower shop! With 4 bedrooms and 1.5 bathrooms, this well-maintained property offers incredible space, character, and small-town walkability. From the welcoming front porch to the large family room that opens to an oversized deck, this home is perfect for entertaining or relaxing in your own downtown retreat. The detached garage includes a workshop and a massive upper-level storage area, offering endless possibilities for hobbies, business, or expansion. Ready for your personal touches, this property blends original charm with room to grow. Located

$255,000 Last sold price

4 beds1.5 baths2,406 sq ft

108 S 2nd St, Denton, MD 21629

(443) 274-1900

SOLD SEP 26, 2025

ABOUT THIS HOME
Recently Sold Home in Caroline County, MD:
Don't Miss This Stunning Cape Cod w/ A Spacious Open Floor Plan and Welcoming Front Porch. You Will Love The Two Story Great Room w/ Pine Floors and Ceiling As Well As Wood Fireplace That Is Open To The Bright Kitchen w/ large Island, Granite Counters. Retreat To The First Floor Primary Suite w/ Full Bath and Walk In Closet. The Home Also Boasts A Beautiful Formal Dining Room and Office / Living Room. Upstairs You Have A Finished Family Room and Cat Walk Overlooking The Great Room + 2 More Nice Bedrooms. Relax On Your 26x15 Screened Porch and Deck That Overlooks Your Private Rear Yard. You Also Have A Great Walk In Attic Storage Space That's 23x12 and A Two Car Garage. The HVAC Systems are

$475,000 Last sold price

4 beds3 baths3,206 sq ft

8534 Duffers Dell, Denton, MD 21629

(410) 549-3500

SOLD OCT 24, 2025

ABOUT THIS HOME
Recently Sold Home in Caroline County, MD:
Coming Soon! Downtown Charm Meets Cozy Comfort Step into this delightful downtown bungalow—move-in ready and brimming with character. Featuring 2 spacious bedrooms, 1 full bathroom, a welcoming living area, and a functional galley kitchen, this home offers the perfect blend of simplicity and style. Start your mornings on the cozy front porch, ideal for sipping coffee and watching the world go by. Out back, enjoy a large fenced-in yard with plenty of space for pets, gardening, or entertaining—plus a handy storage shed for all your tools and gear. Prime location in the heart of downtown means you're just steps away from local shops, restaurants, and community events. Whether you'r

$215,000 Last sold price

2 beds1 bath640 sq ft

522 Lincoln St, Denton, MD 21629

(410) 479-4663

SOLD SEP 16, 2025

ABOUT THIS HOME
Recently Sold Home in Caroline County, MD:
Charming 4 bedroom, 2 bath Cape Cod just a short distance to the Newly Open 2025 Caroline Country Club. Situated on over 1/2 acre with access off Pealiquor Rd or Woods Rd. Mature shade trees and extensive landscaping. A large deck leading to your own gazebo with hot tub, buyer to verify working condition. Updated kitchen with granite and Stainless Appliances. The roof was replaced in 2023 and new heat pump 2025. There is a whole home generator, so no need to worry about power outages.

$420,000 Last sold price

4 beds2 baths2,040 sq ft

24711 Pealiquor Rd, Denton, MD 21629

(410) 822-1415

SOLD SEP 4, 2025

ABOUT THIS HOME
Recently Sold Home in Caroline County, MD:
Welcome to 8534 Briar Patch Drive. This very well maintained home has so much to offer. This beautifully maintained property offers four spacious bedrooms and three bathrooms, providing ample space and comfort for family living or entertaining guests. The main floor includes a foyer, living room, formal dining room, family room, living room, kitchen, sunroom, and a breakfast nook that overlooks the serene backyard through sliding doors that lead out to the back deck. There is also an office off the kitchen that could easily be converted into a butler's pantry. Featuring brand-new flooring throughout, the interior feels fresh and updated, blending style with functionality. Other features inc

$540,000 Last sold price

4 beds3 baths3,039 sq ft

8534 Briar Patch Dr, Denton, MD 21629

(855) 849-4663

Property at 25790 Herring Ln, Denton, MD 21629, 3 beds, 2 baths

$469,000 Last sold price

3 beds2 baths2,132 sq ft

25790 Herring Ln, Denton, MD 21629

(410) 822-6272

Property at 306 S 2nd St, Denton, MD 21629, 5 beds, 2.5 baths

$399,000 Last sold price

5 beds2.5 baths2,267 sq ft

306 S 2nd St, Denton, MD 21629

(410) 822-6272

Property at 515 Franklin St, Denton, MD 21629, 3 beds, 1.5 baths

$270,000 Last sold price

3 beds1.5 baths1,409 sq ft

515 Franklin St, Denton, MD 21629

(410) 583-0400

Property at 614 Market St, Denton, MD 21629, 3 beds, 2.5 baths

$325,000 Last sold price

3 beds2.5 baths2,508 sq ft

614 Market St, Denton, MD 21629

(410) 758-2929

Property at 9709 Foy Rd, Denton, MD 21629, 3 beds, 2 baths

$94,900 Last sold price

3 beds2 baths2,312 sq ft

9709 Foy Rd, Denton, MD 21629

(877) 328-4400

Property at 529 N 6th St, Denton, MD 21629, 3 beds, 1 bath

$249,500 Last sold price

3 beds1 bath1,019 sq ft

529 N 6th St, Denton, MD 21629

(443) 496-4040

Property at 26042 Line Rd, Denton, MD 21629, 3 beds, 1 bath

$80,000 Last sold price

3 beds1 bath720 sq ft

26042 Line Rd, Denton, MD 21629

(410) 479-3993

Property at 6999 Breeding Rd, Federalsburg, MD 21632, 3 beds, 2 baths

$184,000 Last sold price

3 beds2 baths1,500 sq ft

6999 Breeding Rd, Federalsburg, MD 21632

(410) 543-4545

Property at 122 Mill St, Greensboro, MD 21639, 3 beds, 2 baths

$280,000 Last sold price

3 beds2 baths1,104 sq ft

122 Mill St, Greensboro, MD 21639

(410) 224-0600

Property at 113 Boyce Ml, Greensboro, MD 21639, 3 beds, 2 baths

$235,000 Last sold price

3 beds2 baths1,200 sq ft

113 Boyce Ml, Greensboro, MD 21639

(410) 479-0777

Property at 13243 Greensboro Rd, Greensboro, MD 21639, 2 beds, 2 baths

$100,000 Last sold price

2 beds2 baths1,092 sq ft

13243 Greensboro Rd, Greensboro, MD 21639

(410) 479-0777

Property at 502 N Academy St N, Greensboro, MD 21639, 3 beds, 2 baths

$385,000 Last sold price

3 beds2 baths2,378 sq ft

502 N Academy St N, Greensboro, MD 21639

(443) 988-0114

Property at 603 W Sunset Ave, Greensboro, MD 21639, 5 beds

$175,950 Last sold price

5 beds— baths1,983 sq ft

603 W Sunset Ave, Greensboro, MD 21639

(410) 643-5005

Property at 12680 Greensboro Rd, Greensboro, MD 21639, 3 beds, 1 bath

$229,000 Last sold price

3 beds1 bath720 sq ft

12680 Greensboro Rd, Greensboro, MD 21639

(410) 778-0330

Property at 406 N Academy St, Greensboro, MD 21639, 3 beds, 2 baths

$325,000 Last sold price

3 beds2 baths1,528 sq ft

406 N Academy St, Greensboro, MD 21639

(240) 583-1183

Property at 111 Parkland Rd, Greensboro, MD 21639, 4 beds, 2 baths

$289,990 Last sold price

4 beds2 baths1,460 sq ft

111 Parkland Rd, Greensboro, MD 21639

(301) 407-2600

Property at 508 W Sunset Ave, Greensboro, MD 21639, 3 beds, 1 bath

$250,000 Last sold price

3 beds1 bath1,120 sq ft

508 W Sunset Ave, Greensboro, MD 21639

(410) 224-2200

Property at 104 Hobbs St, Greensboro, MD 21639, 3 beds, 1 bath

$265,000 Last sold price

3 beds1 bath1,248 sq ft

104 Hobbs St, Greensboro, MD 21639

(301) 970-2447

Property at 17635 Cool Spring Rd, Marydel, MD 21649, 3 beds, 2 baths

$320,000 Last sold price

3 beds2 baths1,782 sq ft

17635 Cool Spring Rd, Marydel, MD 21649

(410) 729-7700

Property at 104 Roe St, Greensboro, MD 21639, 3 beds, 2 baths

$275,000 Last sold price

3 beds2 baths1,204 sq ft

104 Roe St, Greensboro, MD 21639

(410) 721-1500

Property at 15551 Wharton Rd, Goldsboro, MD 21636, 3 beds, 2 baths

$804,000 Last sold price

3 beds2 baths2,160 sq ft

15551 Wharton Rd, Goldsboro, MD 21636

(302) 217-6692

Property at 17990 Henderson Rd, Marydel, MD 21649, 1 bed, 1 bath

$165,000 Last sold price

1 bed1 bath1,527 sq ft

17990 Henderson Rd, Marydel, MD 21649

(410) 677-0909

Property at 15 Ridgeway Dr, Ridgely, MD 21660, 3 beds, 2 baths

$354,900 Last sold price

3 beds2 baths1,560 sq ft

15 Ridgeway Dr, Ridgely, MD 21660

(410) 643-3033

Property at 24316 Auction Rd, Preston, MD 21655, 3 beds, 1 bath

$350,000 Last sold price

3 beds1 bath1,438 sq ft

24316 Auction Rd, Preston, MD 21655

(410) 745-0415

Property at 23274 Holly Park Dr, Preston, MD 21655, 4 beds, 3 baths

$875,000 Last sold price

4 beds3 baths2,119 sq ft

23274 Holly Park Dr, Preston, MD 21655

(443) 274-1900

Property at 23290 Ninetown Rd, Ridgely, MD 21660, 4 beds, 2 baths

$605,000 Last sold price

4 beds2 baths2,005 sq ft

23290 Ninetown Rd, Ridgely, MD 21660

(410) 543-4545

Property at 12615 Eveland Rd, Ridgely, MD 21660, 3 beds, 3 baths

$369,900 Last sold price

3 beds3 baths2,607 sq ft

12615 Eveland Rd, Ridgely, MD 21660

(410) 643-2244

Property at 8816 Dorothy Ln, Denton, MD 21629, 4 beds, 3.5 baths

$940,000 Last sold price

4 beds3.5 baths4,092 sq ft

8816 Dorothy Ln, Denton, MD 21629

(302) 217-6692

Property at 317 Central Ave W, Federalsburg, MD 21632, 4 beds, 1.5 baths

$240,000 Last sold price

4 beds1.5 baths1,670 sq ft

317 Central Ave W, Federalsburg, MD 21632

(301) 442-7222

Property at 107 Butler Dr, Denton, MD 21629, 4 beds, 1.5 baths

$359,000 Last sold price

4 beds1.5 baths2,974 sq ft

107 Butler Dr, Denton, MD 21629

(301) 970-2447

Property at 25432 Piney Branch Ln, Denton, MD 21629, 3 beds, 2 baths

$360,000 Last sold price

3 beds2 baths1,746 sq ft

25432 Piney Branch Ln, Denton, MD 21629

(410) 822-6665

Property at 102 Roe St, Greensboro, MD 21639, 3 beds, 2 baths

$229,000 Last sold price

3 beds2 baths1,212 sq ft

102 Roe St, Greensboro, MD 21639

(443) 448-8320

Property at 609 Cedar Ln, Greensboro, MD 21639, 1 bed, 1 bath

$149,900 Last sold price

1 bed1 bath800 sq ft

609 Cedar Ln, Greensboro, MD 21639

(410) 479-2000

Property at 25266 Smith Landing Rd, Denton, MD 21629, 2 beds, 1 bath

$315,000 Last sold price

2 beds1 bath1,256 sq ft

25266 Smith Landing Rd, Denton, MD 21629

(443) 448-8320

Property at 12194 Knife Box Rd, Greensboro, MD 21639, 2 beds, 2 baths

$225,000 Last sold price

2 beds2 baths1,488 sq ft

12194 Knife Box Rd, Greensboro, MD 21639

(302) 217-6692

Property at 512 Lincoln St, Denton, MD 21629, 3 beds, 2 baths

$294,000 Last sold price

3 beds2 baths1,420 sq ft

512 Lincoln St, Denton, MD 21629

(410) 543-4545

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Recently Sold Homes in Caroline County

There are currently 132 recently sold homes 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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Recently Sold Homes in Caroline County, MD

Recently Sold Homes in Caroline County

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