Homes with Pools for Sale in Caroline County, MD

139 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Well built and lovingly maintained 3 bedroom, 2 bath rancher on 1 acre. New roof installed 2024. Nice open yard with established shade trees around the house. Small barn at rear of the property.

$359,000

3 beds2 baths1,642 sq ft

4215 Preston Rd, Preston, MD 21655

1 acre lot • 4 parking spots • Built 1959

(410) 479-2000

NEW 28 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Seller Requestes to use Cardinal Title. Sold AS-IS and Priced to Sell! Located on a quiet rural road, this 1-acre property is ideal for investors, homeowners or builders. Major rehab needed or tear down and build your dream home. Great opportunity!

$89,900

3 beds1 bath1,152 sq ft

22415 Hillsboro Rd, Denton, MD 21629

1-acre property • 1 acre lot • Built 1910

(443) 317-8125

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Nestled in the serene Meadow Wood subdivision, this charming brick Colonial home offers a perfect blend of comfort and tranquility. With 2.56+/- acres of partly wooded land, enjoy the peaceful ambiance of nature right in your backyard, complete with a picturesque pond view. This 3 Bedroom, 3 Bath home offers 2645 +/- sq ft living space and a true secluded and private country feel. The inviting interior features an open floor plan that seamlessly connects the family room to the country-style kitchen, ideal for gatherings. The kitchen boasts upgraded countertops, an island, and essential appliances, including a newer refrigerator, self-cleaning oven and dishwasher, making meal prep a delight.

$385,000

3 beds3 baths2,645 sq ft

14957 Cherry Ln, Ridgely, MD 21660

Open floor plan • Upgraded countertops • Partly wooded land

(410) 822-6665

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Enjoy the best of Eastern Shore living with the tranquility of a quiet, country setting while remaining conveniently located just outside of the quaint little town of Ridgely. This nanticoke rancher features a nice family room addition off the kitchen and is located on a private 2 acre lot on the end of a cul-de-sac. Featuring 3 bedrooms and 2 full baths and a two car garage. This property also has a green house that is in need of a little tlc, and a total of 3 wells. Home is subject to a solar lease and is being sold as-is.

$399,000

3 beds2 baths1,792 sq ft

24029 Meadows Dr, Ridgely, MD 21660

2 acre lot • 2 garage spots • Built 1990

(410) 476-2201

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
A Private Eastern Shore Compound Designed for Living, Relaxing & Entertaining! Welcome to 13539 Hokum Drive, a rare Eastern Shore retreat offering privacy, amenities, and “room to breathe” on a gorgeous, partially wooded landscape. This isn’t just a home — it’s a full lifestyle setting, complete with multiple outbuildings, an in-ground pool, wooded trails, and incredible outdoor living spaces, and did we mention an Island! From the moment you enter the long, tree-lined gravel driveway, the property unfolds like a private estate. Mature oaks frame the entrance, opening to a wide courtyard of parking and easy access to the home, the detached garage, and th

$1,100,000

5 beds3 baths3,704 sq ft

13539 Hokum Dr, Greensboro, MD 21639

3.14 acre lot • 5 garage spots • Pool

(443) 256-3773

Property at 24712 Tribbett Cir, Ridgely, MD 21660, 4 beds, 4 baths

$629,900

4 beds4 baths3,491 sq ft

24712 Tribbett Cir, Ridgely, MD 21660

(410) 546-3211

Property at 26067 Goldsboro Rd, Goldsboro, MD 21636, 3 beds, 2.5 baths

$629,900

3 beds2.5 baths2,080 sq ft

26067 Goldsboro Rd, Goldsboro, MD 21636

(410) 643-5005

Property at 106 Briarwood Cir, Denton, MD 21629, 3 beds, 2.5 baths

$399,900

3 beds2.5 baths2,551 sq ft

106 Briarwood Cir, Denton, MD 21629

(410) 255-3690

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

$369,000

3 beds2 baths1,292 sq ft

3 Sunrise Ave, Ridgely, MD 21660

(410) 543-4545

Property at 11 N Maple Ave, Ridgely, MD 21660, 3 beds, 1 bath

$200,000

3 beds1 bath814 sq ft

11 N Maple Ave, Ridgely, MD 21660

(410) 304-2250

$155,000

3 beds1.5 baths1,393 sq ft

109 Buena Vista Buena Vista Ave, Federalsburg, MD 21632

(410) 754-7000

Property at 4218 Harmony Rd, Preston, MD 21655, 8 beds, 12 baths

$2,999,000

8 beds12 baths9,364 sq ft

4218 Harmony Rd, Preston, MD 21655

(410) 543-4545

Property at 106 S 6th St, Denton, MD 21629, 3 beds, 2 baths

$169,000

3 beds2 baths2,776 sq ft

106 S 6th St, Denton, MD 21629

(410) 543-4545

Property at 318 Carter Ave, Denton, MD 21629, 2 beds, 2 baths

$258,900

2 beds2 baths606 sq ft

318 Carter Ave, Denton, MD 21629

(410) 770-9255

Property at 4305 Langrell Rd, Preston, MD 21655, 4 beds, 2 baths

$399,000

4 beds2 baths2,076 sq ft

4305 Langrell Rd, Preston, MD 21655

(443) 274-1900

Property at 9946 New Bridge Rd, Denton, MD 21629, 3 beds, 1 bath

$250,000

3 beds1 bath960 sq ft

9946 New Bridge Rd, Denton, MD 21629

(443) 215-4663

Property at 5585 Harmony Woods Dr, Preston, MD 21655, 4 beds, 2.5 baths

$549,000

4 beds2.5 baths3,442 sq ft

5585 Harmony Woods Dr, Preston, MD 21655

(410) 770-9255

Property at 121 Edenton Ln, Denton, MD 21629, 3 beds, 2 baths

$315,000

3 beds2 baths1,232 sq ft

121 Edenton Ln, Denton, MD 21629

(410) 822-6665

Property at 26091 Hokum Dr, Greensboro, MD 21639, 4 beds, 2.5 baths

$429,900

4 beds2.5 baths2,248 sq ft

26091 Hokum Dr, Greensboro, MD 21639

(410) 260-2800

Property at 8578 Tuckahoe Rd, Denton, MD 21629, 4 beds, 3 baths

$425,000

4 beds3 baths1,680 sq ft

8578 Tuckahoe Rd, Denton, MD 21629

(443) 448-8320

Property at 24276 Asbury Dr, Denton, MD 21629, 4 beds, 2.5 baths

$642,900

4 beds2.5 baths2,920 sq ft

24276 Asbury Dr, Denton, MD 21629

(410) 822-9000

Property at 115 Boyce Mill Rd, Greensboro, MD 21639, 3 beds, 1 bath

$219,000

3 beds1 bath1,350 sq ft

115 Boyce Mill Rd, Greensboro, MD 21639

(410) 479-0777

Property at 305 Central Ave, Ridgely, MD 21660, 5 beds, 2 baths

$330,000

5 beds2 baths2,574 sq ft

305 Central Ave, Ridgely, MD 21660

(410) 822-9000

Property at 23629 Willow Pond Rd, Denton, MD 21629, 1 bed, 1.5 baths

$450,000

1 bed1.5 baths1,596 sq ft

23629 Willow Pond Rd, Denton, MD 21629

(410) 770-3600

Property at 229 Oldtown Rd, Goldsboro, MD 21636, 3 beds, 2 baths

$296,000

3 beds2 baths1,368 sq ft

229 Oldtown Rd, Goldsboro, MD 21636

(301) 970-2447

Property at 13306 Greensboro Rd, Greensboro, MD 21639, 2 beds, 1.5 baths

$355,000

2 beds1.5 baths708 sq ft

13306 Greensboro Rd, Greensboro, MD 21639

(410) 827-4663

Property at 203 Hobbs St, Greensboro, MD 21639, 3 beds, 2 baths

$286,990

3 beds2 baths1,219 sq ft

203 Hobbs St, Greensboro, MD 21639

(301) 407-2600

Property at 25607 Garey Rd, Denton, MD 21629, 3 beds, 2 baths

$315,000

3 beds2 baths920 sq ft

25607 Garey Rd, Denton, MD 21629

(410) 822-6665

Property at 206 Charles St, Federalsburg, MD 21632, 3 beds, 2.5 baths

$361,000

3 beds2.5 baths1,734 sq ft

206 Charles St, Federalsburg, MD 21632

(302) 539-1777

Property at 8548 Dogwood Blossom Ln, Denton, MD 21629, 4 beds, 2.5 baths

$394,000

4 beds2.5 baths2,176 sq ft

8548 Dogwood Blossom Ln, Denton, MD 21629

(410) 479-4663

Property at 3540 Houston Branch Rd, Federalsburg, MD 21632, 2 beds, 1 bath

$279,000

2 beds1 bath1,140 sq ft

3540 Houston Branch Rd, Federalsburg, MD 21632

(410) 822-1415

Property at 1412 Blue Heron Dr, Denton, MD 21629, 3 beds, 2.5 baths

$240,000

3 beds2.5 baths1,709 sq ft

1412 Blue Heron Dr, Denton, MD 21629

(410) 729-7700

Property at 8025 Laurel Ln, Denton, MD 21629, 5 beds, 2 baths

$425,000

5 beds2 baths2,061 sq ft

8025 Laurel Ln, Denton, MD 21629

(301) 862-4000

Property at 21405 Tanyard Rd, Preston, MD 21655, 4 beds, 3 baths

$440,000

4 beds3 baths3,212 sq ft

21405 Tanyard Rd, Preston, MD 21655

(301) 970-2447

Property at 24800 Pealiquor Rd, Denton, MD 21629, 4 beds, 3.5 baths

$1,295,000

4 beds3.5 baths4,496 sq ft

24800 Pealiquor Rd, Denton, MD 21629

(304) 645-7700

Property at 511 Bernard Ave, Greensboro, MD 21639, 3 beds, 1 bath

$245,000

3 beds1 bath1,385 sq ft

511 Bernard Ave, Greensboro, MD 21639

(410) 827-4663

Property at 3547 Prchal Rd, Preston, MD 21655, 4 beds, 3 baths

$875,000

4 beds3 baths3,149 sq ft

3547 Prchal Rd, Preston, MD 21655

(410) 972-4000

Property at 2766 Veterans Dr, Federalsburg, MD 21632, 3 beds, 1 bath

$299,000

3 beds1 bath1,284 sq ft

2766 Veterans Dr, Federalsburg, MD 21632

(410) 479-4663

Property at 1612 Cattail Commons Way, Denton, MD 21629, 4 beds, 2.5 baths

$399,900

4 beds2.5 baths2,492 sq ft

1612 Cattail Commons Way, Denton, MD 21629

(410) 531-0321

Property at 206 Academy St, Greensboro, MD 21639, 3 beds, 1.5 baths

$239,999

3 beds1.5 baths1,565 sq ft

206 Academy St, Greensboro, MD 21639

(302) 217-6692

Property at 1403 Blue Heron Dr, Denton, MD 21629, 3 beds, 2.5 baths

$225,000

3 beds2.5 baths1,680 sq ft

1403 Blue Heron Dr, Denton, MD 21629

(443) 829-5828

Viewing page 1 of 4

Homes with Pools for Sale in Caroline County

There are currently 139 homes with pools 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.

More real estate resources for Caroline County, MD

Nearby Counties

Cities

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

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

Why Redfin?

Community Impact

Diversity & Inclusion

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.