Homes with Pools for Sale in Caroline County, MD

139 homes

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ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
This home is high on a hill across from the Tuckahoe Creek with some winter views of the water. --the park across the street has a ramp for boats, kayaks, and canoes. The home has 3 bedrooms and a small room for office or nursery or whatever you want it to be; , and one full bath -- all upstairs. The front porch entrance opens to a foyer and the living room to the right and then the dining room and on to the kitchen in the rear of the home. The washer and dryer are located in a utility room that also has the old-fashioned "cellar door" in the floor that enables access to the basement below. The kitchen needs all new appliances and cabinets, etc. The home is a fixer-upper but cou

$189,900

3 beds1 bath1,904 sq ft

21948 Main St, Hillsboro, MD 21641

Utility room • High on a hill • Ramp for boats

(410) 479-3993

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and extra space for modern living. Outside, you’ll find an oversized shop/garage ideal for hobbies, storage, or a workshop. The property also includes a home generator, adding peace of mind. While the home does need some work, it has great bones and endless potential to become a stunning residence onc

$245,000

3 beds2 baths1,840 sq ft

158 Wright St, Preston, MD 21655

6,550 sq ft lot • Built 1890 • Listed 101 days

(410) 822-9000

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Why wait months to build when you can start enjoying this meticulously built, and finely crafted contemporary farmhouse home right now? Situated on an . 85 acre lot in the established community of Ashworth, this 2023 built, 3,168 square foot, 4 bedroom, 2.5 bath home contemporary farmhouse-style home blends rustic charm with contemporary elegance. The exterior features classic white siding, complemented by black trim and large windows that enhance its inviting façade Inside, the open concept layout is accentuated by beautiful luxury vinyl plank flooring, high ceilings, and tall windows that flood the space with natural light. The spacious great room boasts a decorative gas fireplace,

$595,000

4 beds2.5 baths3,168 sq ft

24766 Tribbett Cir, Ridgely, MD 21660

0.85 acre lot • 2 garage spots • Built 2023

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Three Bedroom, 1 and a half bathrooms, located on a quiet county road. This house has been freshly painted inside and outside, new LVP flooring installed throughout the house, all interior doors have been replaced with white six panel doors and new light fixtures in each room. New washer/dryer and refrigerator installed, heat pump is 1 year old, and there is a 22 kw Generac generator as a backup power supply. No town Taxes and only minutes away from tax free shopping.

$299,900

3 beds1.5 baths864 sq ft

26606 Idlewild Rd, Federalsburg, MD 21632

0.34 acre lot • 4 parking spots • Built 1968

(410) 479-3993

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Over 3,300 sq. ft. two-story building, constructed in 2006, offers endless potential with a little imagination. Currently a pharmacy, gift shop, and ice cream parlor, it could easily be transformed into a fantastic four-bedroom, 2.5-bath residence or adapted for other mixed-use purposes. Both levels feature open, flexible layouts—ready to be reimagined to suit your vision. Located in the charming town of Ridgely, a convenient commuter hub to both the Western Shore and Delaware, the property is zoned C-2 (Central Business District), allowing for a wide range of possibilities. Additional features include handicap accessibility, a detached storage garage, and a paved parking lot with 14

$495,000

— beds0.5 baths3,321 sq ft

7 W Belle Rd, Ridgely, MD 21660

Paved parking lot • Zoned c-2 • Two story building

(410) 822-6272

Property at 14271 Cedar Ln, Greensboro, MD 21639, 6 beds, 3 baths

$1,475,000

6 beds3 baths3,756 sq ft

14271 Cedar Ln, Greensboro, MD 21639

(443) 292-6767

Property at 300 S 1st St, Denton, MD 21629, 3 beds, 2 baths

$625,000

3 beds2 baths1,616 sq ft

300 S 1st St, Denton, MD 21629

(410) 479-4663

Property at 25513 Hill Rd, Greensboro, MD 21639, 4 beds, 3 baths

$395,000

4 beds3 baths2,464 sq ft

25513 Hill Rd, Greensboro, MD 21639

(410) 479-3993

Property at 2697 Choptank Main St, Preston, MD 21655, 2 beds, 2 baths

$279,000

2 beds2 baths1,104 sq ft

2697 Choptank Main St, Preston, MD 21655

(410) 770-9255

Property at 204 Academy Ave, Federalsburg, MD 21632, 2 beds, 1 bath

$24,500

2 beds1 bath1,024 sq ft

204 Academy Ave, Federalsburg, MD 21632

(410) 677-0909

Property at 25548 Hill Rd, Greensboro, MD 21639, 4 beds

$435,000

4 beds— baths7,260 sq ft

25548 Hill Rd, Greensboro, MD 21639

(410) 742-0300

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

$529,000

4 beds2.5 baths1,920 sq ft

7837 Shore Dr, Preston, MD 21655

(410) 822-1415

Property at 3376 Jefferson Pond Rd, Federalsburg, MD 21632, 3 beds, 2 baths

$300,000

3 beds2 baths1,344 sq ft

3376 Jefferson Pond Rd, Federalsburg, MD 21632

(302) 360-0300

Property at 28219 Bridgeville Rd, Federalsburg, MD 21632, 4 beds, 4.5 baths

$2,750,000

4 beds4.5 baths6,520 sq ft

28219 Bridgeville Rd, Federalsburg, MD 21632

(410) 822-6665

Property at 23296 Wilder Way, Denton, MD 21629, 4 beds, 3.5 baths

$1,395,000

4 beds3.5 baths3,356 sq ft

23296 Wilder Way, Denton, MD 21629

(410) 822-6665

Property at 22005 Main St, Hillsboro, MD 21641, 3 beds, 3 baths

$545,000

3 beds3 baths3,088 sq ft

22005 Main St, Hillsboro, MD 21641

(410) 778-9319

Property at 27279 Jenny Hye Ln, Marydel, MD 21649, 3 beds, 2.5 baths

$355,000

3 beds2.5 baths2,286 sq ft

27279 Jenny Hye Ln, Marydel, MD 21649

(410) 690-7356

Property at 11142 Log Cabin Rd, Denton, MD 21629, 4 beds, 2.5 baths

$899,900

4 beds2.5 baths2,700 sq ft

11142 Log Cabin Rd, Denton, MD 21629

(302) 677-0020

Property at 310 Main St, Marydel, MD 21649, 9 beds

$620,000

9 beds— baths3,600 sq ft

310 Main St, Marydel, MD 21649

(410) 524-6400

Property at 227 Burnite Mill Rd, Harrington, DE 19952, 3 beds, 1.5 baths

$280,000

3 beds1.5 baths2,026 sq ft

227 Burnite Mill Rd, Harrington, DE 19952

(302) 360-0300

Property at 106 Lednum Ave, Preston, MD 21655, 3 beds, 2 baths

$380,000

3 beds2 baths1,440 sq ft

106 Lednum Ave, Preston, MD 21655

(302) 217-6692

Property at 3406 Rose St, Federalsburg, MD 21632, 3 beds, 1.5 baths

$269,900

3 beds1.5 baths1,584 sq ft

3406 Rose St, Federalsburg, MD 21632

(410) 744-6500

Property at 501 Lincoln St, Denton, MD 21629, 3 beds, 1.5 baths

$135,000

3 beds1.5 baths1,664 sq ft

501 Lincoln St, Denton, MD 21629

(410) 479-2000

Property at 505 Maryland Ave, Ridgely, MD 21660, 3 beds, 2 baths

$299,000

3 beds2 baths1,120 sq ft

505 Maryland Ave, Ridgely, MD 21660

(410) 822-6665

Property at 26355 Marydel Rd, Marydel, MD 21649, 1 bed, 1 bath

$155,000

1 bed1 bath512 sq ft

26355 Marydel Rd, Marydel, MD 21649

(410) 479-3993

Property at 208 Oriole Ave, Ridgely, MD 21660, 3 beds, 2 baths

$339,000

3 beds2 baths1,680 sq ft

208 Oriole Ave, Ridgely, MD 21660

(410) 260-2800

Property at Shore Highway-404, Denton, MD 21629

$249,900

— beds— baths— sq ft

Shore Highway-404, Denton, MD 21629

(410) 822-1415

Property at 517 W Sunset Ave, Greensboro, MD 21639, 4 beds

$345,000

4 beds— baths2,260 sq ft

517 W Sunset Ave, Greensboro, MD 21639

(410) 822-6665

Property at 28035 Possum Hill Rd, Federalsburg, MD 21632

$125,000

— beds— baths2,168 sq ft

28035 Possum Hill Rd, Federalsburg, MD 21632

(703) 538-1113

Property at HELENA Plan, Xyrvrp Greensboro, MD 21639, 4 beds, 2 baths

$291,990

4 beds2 baths1,460 sq ft

HELENA Plan, Xyrvrp Greensboro, MD 21639

Listing provided by Zillow

Property at PERRY Plan, Greensboro, MD 21639, 2 beds, 2 baths

$266,990

2 beds2 baths1,059 sq ft

PERRY Plan, Greensboro, MD 21639

Listing provided by Zillow

Property at CURTIS Plan, Greensboro, MD 21639, 3 beds, 2 baths

$276,990

3 beds2 baths1,182 sq ft

CURTIS Plan, Greensboro, MD 21639

Listing provided by Zillow

Property at SULLIVAN Plan, Greensboro, MD 21639, 3 beds, 2 baths

$286,990

3 beds2 baths1,219 sq ft

SULLIVAN Plan, Greensboro, MD 21639

Listing provided by Zillow

Property at 22403 Marsh Creek Rd, Preston, MD 21655, 3 beds, 2 baths

$384,900

3 beds2 baths1,448 sq ft

22403 Marsh Creek Rd, Preston, MD 21655

(410) 744-6500

Property at 23547 Jonestown Ln, Preston, MD 21655

$25,000

— beds— baths728 sq ft

23547 Jonestown Ln, Preston, MD 21655

(410) 972-4000

$30,000

— beds1 bath— sq ft

12087 Wayman St, Ridgely, MD 21660

(240) 737-5000

Property at 5.281 Acres Schulyer Rd, Goldsboro, MD 21636

$169,900

— beds— baths— sq ft

5.281 Acres Schulyer Rd, Goldsboro, MD 21636

(301) 970-2447

Property at Burnt Mill Rd Lot 3, Ridgely, MD 21660

$127,000

— beds— baths— sq ft

Burnt Mill Rd Lot 3, Ridgely, MD 21660

(202) 944-5000

$440,000

— beds— baths— sq ft

River Rd, Ridgely, MD 21660

(410) 479-2000

Property at Trunk Line Rd, Henderson, MD 21640

$139,900

— beds— baths— sq ft

Trunk Line Rd, Henderson, MD 21640

(301) 970-2447

Property at 10440 Burrsville Branch Rd, Denton, MD 21629

$89,000

— beds— baths— sq ft

10440 Burrsville Branch Rd, Denton, MD 21629

(443) 988-0483

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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.

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