Pending Listings in Caroline County, MD

48 homes

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UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Caroline County, MD:
✨Charming Updated Cottage in the Heart of Greensboro, MD Welcome home to this beautiful 2-bedroom, 1-bath rancher offering the perfect blend of comfort and modern style. Step inside to find a bright, open-concept living space featuring warm wood floors, recessed lighting, and a cozy family room that flows seamlessly into the stunning kitchen. The kitchen boasts upgraded cabinetry, butcher block countertops, stainless steel appliances, and a large island with seating — ideal for entertaining or casual dining. The spacious bathroom has been completely remodeled with contemporary finishes, including a custom vanity with sliding barn doors, luxury vinyl plank flooring, and stylish fixture

$189,900

2 beds1 bath840 sq ft

116 Stonesifer Dr, Greensboro, MD 21639

Upgraded cabinetry • 9,806 sq ft lot • Built 1954

(301) 970-2447

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Caroline County, MD:
* * Accepting other offers * * Situated on 4.14± private acres, this 3-bedroom, 2.5-bath home couples serene country living with exceptional craftsmanship. Inside, the first floor offers a formal dining room, large eat in kitchen with stainless steel appliances, vaulted ceiling living room with two story stone fireplace, first floor primary with walk in closet and Whirlpool tub, office with built ins, and sunroom. Upstairs, 2 well sized bedrooms sit at each side of the home, connected by an overlook to the living room. The oversized 2-car attached garage provides plenty of storage and includes a finished room above with mini-splits, creating a flexible space for guests, office, or

$740,000

3 beds2.5 baths3,326 sq ft

3485 Gallagher Rd, Preston, MD 21655

Private acres • Large eat in kitchen • Formal dining room

(410) 822-6665

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Caroline County, MD:
Welcome home to this beautifully updated 4-bedroom, 2.5-bath Colonial tucked away in a peaceful neighborhood just minutes from historic downtown Denton! Enjoy the best of both worlds — a quiet suburban setting with easy access to Rt. 404, Rt. 50, and Rt. 301, and only about 30 minutes to the Bay Bridge for commuters or weekend getaways. Built in 2006 and thoughtfully refreshed with modern updates, this home truly shines. Recent improvements include a brand-new water heater (2024), new carpeting throughout (2024), contemporary lighting inside and out, remodeled bathrooms (2024), new laundry appliances (2024), white vinyl fencing (2025) and a premium 50-year architectural roof (installe

$408,000

4 beds2.5 baths2,994 sq ft

1208 Painted Fern Rd, Denton, MD 21629

0.25 acre lot • 2 garage spots • Built 2006

(410) 583-0400

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Caroline County, MD:
Stunning waterfront property on the Choptank River featuring a private dock, boat lift and deep water access. This spacious home offers 4 bedrooms and 2 bathrooms, an inviting sunroom, hardwood flooring throughout, and a cozy fireplace. The unfinished basement provides potential for customization. Additional amenities include a 2 car attached garage on a 1 acre lot with no covenants or restrictions. NOTE: New roof, septic, and many more improvements throughout! Perfect property for enjoying serene river views and outdoor living!

$725,000

4 beds2 baths2,273 sq ft

25211 Adams Landing Rd, Denton, MD 21629

Boat lift • Hardwood flooring • Private dock

(410) 479-3993

UNDER CONTRACT

ABOUT THIS HOME
Pending Listing in Caroline County, MD:
Approximately 2 acres (parcels 289, 196) on a point on Little Creek off the Choptank River. Two bedroom, one bath log cabin with loft. An additional accessary log cabin. Easy access to Easton or Preston. Great waterfowl location.

$318,000

2 beds1 bath1,438 sq ft

4935 Edmondson Creek Rd, Preston, MD 21655

Waterfowl location • Accessary log cabin • Log cabin

(410) 822-6665

Property at 8259 Haven St, Denton, MD 21629, 3 beds, 1 bath

$280,000

3 beds1 bath1,392 sq ft

8259 Haven St, Denton, MD 21629

(410) 822-1415

Property at 311 Holt St, Federalsburg, MD 21632, 3 beds, 1 bath

$130,000

3 beds1 bath1,696 sq ft

311 Holt St, Federalsburg, MD 21632

(410) 690-7356

Property at 409 Main St, Goldsboro, MD 21636, 2 beds, 1.5 baths

$205,000

2 beds1.5 baths1,252 sq ft

409 Main St, Goldsboro, MD 21636

(410) 543-4545

Property at 25946 Garey Rd, Denton, MD 21629, 3 beds, 2.5 baths

$435,000

3 beds2.5 baths2,105 sq ft

25946 Garey Rd, Denton, MD 21629

(888) 822-7573

Property at 25749 Herring Ln, Denton, MD 21629, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths2,190 sq ft

25749 Herring Ln, Denton, MD 21629

(443) 205-4007

Property at 22991 Westview Dr, Preston, MD 21655, 3 beds, 1 bath

$272,000

3 beds1 bath1,032 sq ft

22991 Westview Dr, Preston, MD 21655

(410) 643-5005

Property at 14990 Greensboro Rd, Goldsboro, MD 21636, 3 beds, 2 baths

$399,000

3 beds2 baths2,016 sq ft

14990 Greensboro Rd, Goldsboro, MD 21636

(410) 479-2000

Property at 1233 Painted Fern Rd, Denton, MD 21629, 5 beds, 3.5 baths

$459,500

5 beds3.5 baths4,222 sq ft

1233 Painted Fern Rd, Denton, MD 21629

(410) 822-2152

Property at 5135 Clark Canning House Rd, Federalsburg, MD 21632, 3 beds, 2.5 baths

$365,900

3 beds2.5 baths1,872 sq ft

5135 Clark Canning House Rd, Federalsburg, MD 21632

(410) 543-4545

Property at 113 Maple Ave, Goldsboro, MD 21636, 3 beds, 2 baths

$230,000

3 beds2 baths1,448 sq ft

113 Maple Ave, Goldsboro, MD 21636

(410) 822-6272

Property at 21084 Marsh Creek Rd, Preston, MD 21655, 3 beds, 2 baths

$299,900

3 beds2 baths1,144 sq ft

21084 Marsh Creek Rd, Preston, MD 21655

(410) 822-1415

Property at 207 Gay St, Denton, MD 21629, 4 beds

$249,900

4 beds— baths1,820 sq ft

207 Gay St, Denton, MD 21629

(410) 479-2000

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

$289,000

3 beds1 bath1,392 sq ft

6101 Bethlehem Rd, Preston, MD 21655

(410) 822-9000

Property at 3345 Gallagher Rd, Preston, MD 21655, 3 beds, 2 baths

$375,000

3 beds2 baths1,312 sq ft

3345 Gallagher Rd, Preston, MD 21655

(302) 629-5575

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

$229,000

3 beds2 baths1,212 sq ft

102 Roe St, Greensboro, MD 21639

(443) 448-8320

Property at 13070 Ridgely Rd, Greensboro, MD 21639, 3 beds, 2 baths

$370,000

3 beds2 baths1,344 sq ft

13070 Ridgely Rd, Greensboro, MD 21639

(410) 778-0330

Property at 8197 Detour Rd, Denton, MD 21629, 3 beds, 3 baths

$629,000

3 beds3 baths2,565 sq ft

8197 Detour Rd, Denton, MD 21629

(410) 228-0800

Property at 6401 Laurel Grove Rd, Denton, MD 21629, 3 beds, 2 baths

$1,200,000

3 beds2 baths2,320 sq ft

6401 Laurel Grove Rd, Denton, MD 21629

(302) 227-5000

Property at Iron Gate Rd, Federalsburg, MD 21632

$75,000

— beds— baths— sq ft

Iron Gate Rd, Federalsburg, MD 21632

(443) 448-8320

Property at 3622 Choptank Rd, Preston, MD 21655, 2 beds, 1.5 baths

$299,900

2 beds1.5 baths1,700 sq ft

3622 Choptank Rd, Preston, MD 21655

(410) 220-4648

Property at 8 Sunrise Ave, Ridgely, MD 21660, 3 beds, 2 baths

$384,900

3 beds2 baths1,292 sq ft

8 Sunrise Ave, Ridgely, MD 21660

(410) 543-4545

Property at 314 Kerr Ave, Denton, MD 21629, 3 beds, 2 baths

$375,000

3 beds2 baths1,764 sq ft

314 Kerr Ave, Denton, MD 21629

(410) 479-3993

Property at 120 Julie Ln, Federalsburg, MD 21632, 3 beds, 2.5 baths

$220,990

3 beds2.5 baths1,365 sq ft

120 Julie Ln, Federalsburg, MD 21632

(301) 407-2600

Property at 334 Deep Shore Rd, Denton, MD 21629, 3 beds, 2 baths

$359,500

3 beds2 baths1,640 sq ft

334 Deep Shore Rd, Denton, MD 21629

(443) 988-0483

Property at 1626 Blue Heron Dr, Denton, MD 21629, 4 beds, 3.5 baths

$289,900

4 beds3.5 baths2,244 sq ft

1626 Blue Heron Dr, Denton, MD 21629

(410) 643-4131

Property at 301 Central Ave, Ridgely, MD 21660, 4 beds, 1 bath

$189,000

4 beds1 bath1,706 sq ft

301 Central Ave, Ridgely, MD 21660

(410) 822-6665

Property at 10 Sunrise Ave, Ridgely, MD 21660, 4 beds, 3 baths

$399,000

4 beds3 baths1,768 sq ft

10 Sunrise Ave, Ridgely, MD 21660

(410) 543-4545

Property at 1111 Ruddy Duck Ct, Denton, MD 21629, 4 beds, 2.5 baths

$389,900

4 beds2.5 baths2,670 sq ft

1111 Ruddy Duck Ct, Denton, MD 21629

(717) 461-7201

Property at 120 Parkland Rd, Greensboro, MD 21639, 2 beds, 2 baths

$259,990

2 beds2 baths1,059 sq ft

120 Parkland Rd, Greensboro, MD 21639

(301) 407-2600

Property at 1111 Daylily Ln, Denton, MD 21629, 4 beds, 2.5 baths

$399,000

4 beds2.5 baths3,838 sq ft

1111 Daylily Ln, Denton, MD 21629

(443) 274-1900

Property at 125 Parkland Rd, Greensboro, MD 21639, 4 beds, 2 baths

$292,990

4 beds2 baths1,460 sq ft

125 Parkland Rd, Greensboro, MD 21639

(301) 407-2600

Property at 26674 Bentley Pl, Henderson, MD 21640, 4 beds, 2.5 baths

$427,000

4 beds2.5 baths2,124 sq ft

26674 Bentley Pl, Henderson, MD 21640

(410) 747-2800

Property at 153 Riverwalk Ter, Federalsburg, MD 21632, 3 beds, 2.5 baths

$214,990

3 beds2.5 baths1,365 sq ft

153 Riverwalk Ter, Federalsburg, MD 21632

(301) 407-2600

Property at 14 N Maple St, Ridgely, MD 21660, 3 beds, 1 bath

$315,000

3 beds1 bath1,056 sq ft

14 N Maple St, Ridgely, MD 21660

(410) 643-4663

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

$175,000

3 beds1 bath1,763 sq ft

24872 Meeting House Rd, Denton, MD 21629

(703) 378-8810

Property at 113 Parkland Rd, Greensboro, MD 21639, 3 beds, 2 baths

$269,990

3 beds2 baths1,219 sq ft

113 Parkland Rd, Greensboro, MD 21639

(301) 407-2600

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Pending Listings in Caroline County

There are currently 48 pending listings 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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Pending Listings in Caroline County, MD

Pending Listings in Caroline County

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