Homes with Pools for Sale in Caroline County, MD

140 homes

Sort:

Recommended

NEW 1 HR AGO

$99,000

2 beds1 bath956 sq ft

804 Gay St, Denton, MD 21629

7,750 sq ft lot • Built 1915

(410) 479-2000

NEW 39 MINS AGO

$110,000

3 beds1 bath1,032 sq ft

536 Gay St, Denton, MD 21629

5,400 sq ft lot • Built 1910

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
The Home You’ve Been Waiting For! Welcome to 26056 Fox Grape, where country charm meets modern functionality. This 3-bedroom, 2-bath rancher boasts an open-concept layout with a spacious eat-in kitchen flowing seamlessly into the living area—perfect for gatherings and everyday comfort. Step outside to enjoy a 16x16 back deck overlooking a private, fully fenced yard with plenty of room to play, relax, or entertain. A storage shed adds convenience, while thoughtful upgrades—including newer laminate flooring, water heater, dishwasher, and a 2021 well—ensure peace of mind. Ideally situated at the entrance of the subdivision, you’ll love the easy access to Greensbor

$275,000

3 beds2 baths1,215 sq ft

26056 Fox Grape Rd, Greensboro, MD 21639

0.59 acre lot • 6 parking spots • Built 1981

(410) 479-4663

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Step into this charming Victorian home, a delightful blend of classic elegance and modern comfort. With three spacious bedrooms and a full bathroom, this residence offers a warm and inviting atmosphere perfect for relaxation and gatherings. The traditional floor plan enhances the flow of the living spaces, while the hardwood flooring adds a touch of timeless beauty. The heart of the home features a cozy dining area, ideal for sharing meals and creating lasting memories. Natural light pours in through new windows, illuminating the interior and creating a welcoming ambiance. The kitchen is equipped with newer appliances, including a gas oven/range, refrigerator, washer, and dryer, ensuring co

$200,000

3 beds1 bath1,136 sq ft

208 S 3rd St, Denton, MD 21629

6,300 sq ft lot • 2 garage spots • Built 1900

(443) 988-0483

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

Property at 24029 Meadows Dr, Ridgely, MD 21660, 3 beds, 2 baths

$399,000

3 beds2 baths1,792 sq ft

24029 Meadows Dr, Ridgely, MD 21660

(410) 476-2201

Property at 4215 Preston Rd, Preston, MD 21655, 3 beds, 2 baths

$359,000

3 beds2 baths1,642 sq ft

4215 Preston Rd, Preston, MD 21655

(410) 479-2000

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

$375,000

4 beds2 baths1,568 sq ft

24383 Robins Creek Rd, Preston, MD 21655

(410) 770-3600

Property at 132 Hobbs St, Greensboro, MD 21639, 2 beds, 2 baths

$268,490

2 beds2 baths1,059 sq ft

132 Hobbs St, Greensboro, MD 21639

(301) 407-2600

Property at 130 Charlotte Ave, Federalsburg, MD 21632, 3 beds, 2 baths

$315,000

3 beds2 baths1,646 sq ft

130 Charlotte Ave, Federalsburg, MD 21632

(410) 464-5500

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 13539 Hokum Dr, Greensboro, MD 21639, 5 beds, 3 baths

$1,100,000

5 beds3 baths3,704 sq ft

13539 Hokum Dr, Greensboro, MD 21639

(443) 256-3773

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

Property at 109 Buena Vista Buena Vista Ave, Federalsburg, MD 21632, 3 beds, 1.5 baths

$155,000

3 beds1.5 baths1,393 sq ft

109 Buena Vista Buena Vista Ave, Federalsburg, MD 21632

(410) 754-7000

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 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

$374,900

4 beds2 baths2,076 sq ft

4305 Langrell Rd, Preston, MD 21655

(443) 274-1900

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 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 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 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 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 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

$315,000

5 beds2 baths2,574 sq ft

305 Central Ave, Ridgely, MD 21660

(410) 822-9000

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 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 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 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 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 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 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 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 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 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 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 207 Bloomingdale Ave, Federalsburg, MD 21632, 3 beds, 2 baths

$247,500

3 beds2 baths1,684 sq ft

207 Bloomingdale Ave, Federalsburg, MD 21632

(302) 217-6692

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

Viewing page 1 of 4

Homes with Pools for Sale in Caroline County

There are currently 140 homes with pools for sale in Caroline County at a median listing price of $325K. 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 71 days and receive 2 offers. This map is refreshed with the newest listings in Caroline County every 15 minutes.

In the past month, 30 homes have been sold in Caroline County. In addition to houses in Caroline County, there was also 1 condo, 5 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

Cities

Nearby Counties

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.