Homes with Pools for Sale in Caroline County, MD

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ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Offered for the first time, this custom-built home is nestled on 2 private acres in the highly sought-after water access community of Forest Landing, conveniently located between historic downtown Denton and Easton. Beautifully updated and move-in ready, this property offers 3 bedrooms, 2.5 baths, and a finished bonus room, providing flexible space for a home office, gym, playroom, or guest accommodations. Designed with comfort and functionality in mind, the home features a spacious sunken family room ideal for gathering with family and friends, while the living room's gas fireplace creates a warm and inviting atmosphere during the cooler months. Recent improvements include a new roof and m

$569,900

3 beds2.5 baths2,769 sq ft

7884 Laurel Ln, Denton, MD 21629

Private acres • Finished bonus room • Sunken family room

(410) 476-2201

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Photos coming soon! Welcome Home! Don't miss out on this lovely 3 bdrm/2 bath ranch style home with granite counters, stainless appliances, lovely wooden cabinets in the kitchen leading to a screened in porch overlooking the in ground pool and pastoral views! Situated on just over 1 acre of land with a 2 car detached garage, this home offers privacy and peaceful living. Plenty of room for the camper and boat to be parked at home saving on those extra fees. The pellet stove insert can offset those winter heating bills while everyone stays cozy and comfy! Discover Ridgely, Maryland where quiet and peaceful times still exist with an easy drive to all of the necessary amenities. This home has

$399,900

3 beds2 baths1,344 sq ft

11498 Reed Cir, Ridgely, MD 21660

Screened in porch • Stainless appliances • Wooden cabinets

(410) 823-0033

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
More Details & Photos Coming Soon

$649,900

4 beds3 baths2,343 sq ft

7737 Westerly Dr, Preston, MD 21655

1.07 acre lot • 2 garage spots • Pool

(410) 972-4000

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Space, flexibility, and outdoor living come together at 2792 Meadowbrook Road! This spacious 5-bedroom, 2.5-bath split-level home sits on a beautiful . 46-acre lot. The upper level features three bedrooms, including a primary bedroom with its own private bath. The living room offers an open feel and an opportunity to create an even more unique space with the potential for an upper balcony. The kitchen provides abundant cabinet storage and plenty of natural light. Downstairs, you'll find two additional bedrooms, a large family room with an electric fireplace, and a charming stone sitting area with a large sliding glass door that opens directly to the backyard and expansive concrete patio. Th

$325,000

5 beds2.5 baths2,232 sq ft

2792 Meadowbrook Rd, Federalsburg, MD 21632

Stone sitting area • Private bath • Sliding glass door

(302) 360-0300

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
You'll love this custom home nestled on 2.13 private acres, offering over 2,500 square feet of thoughtfully designed living space with 4 bedrooms and 2.5 baths. The open floor plan is highlighted by rich Brazilian hardwood floors, cathedral ceiling, and a welcoming great room anchored by a dramatic floor-to-ceiling brick fireplace. The spacious kitchen opens seamlessly to the great room and features an island, abundant cabinetry, generous counter space, and a built-in breakfast area. The formal dining room provides the perfect setting for holiday meals and special occasions. Relax in the spacious family room or the bright four-season room. It is heated and cooled and overlooks the backyard.

$575,000

4 beds2.5 baths2,426 sq ft

22733 Squire Ln, Queen Anne, MD 21657

Private acres • Spacious kitchen • Custom home

(410) 643-2244

Property at 3769 Bradley Rd, Federalsburg, MD 21632, 3 beds, 2 baths

$755,000

3 beds2 baths2,504 sq ft

3769 Bradley Rd, Federalsburg, MD 21632

(410) 543-4545

Property at 23130 Sparks Road Rd, Ridgely, MD 21660, 3 beds, 2 baths

$599,900

3 beds2 baths1,938 sq ft

23130 Sparks Road Rd, Ridgely, MD 21660

(443) 225-4100

Property at 23071 Tuckahoe Springs Dr, Denton, MD 21629, 4 beds, 3 baths

$1,350,000

4 beds3 baths3,358 sq ft

23071 Tuckahoe Springs Dr, Denton, MD 21629

(410) 228-2525

Property at 28402 Liden School Rd, Denton, MD 21629, 3 beds, 2 baths

$599,000

3 beds2 baths1,834 sq ft

28402 Liden School Rd, Denton, MD 21629

(410) 479-0777

Property at 7392 Todds Wharf Rd, Preston, MD 21655, 3 beds, 2 baths

$399,000

3 beds2 baths1,300 sq ft

7392 Todds Wharf Rd, Preston, MD 21655

(410) 479-3993

Property at 504 Main St, Goldsboro, MD 21636, 3 beds, 2 baths

$342,900

3 beds2 baths1,414 sq ft

504 Main St, Goldsboro, MD 21636

(302) 217-6692

Property at 129 Bloomingdale Ave, Federalsburg, MD 21632, 3 beds, 2 baths

$319,999

3 beds2 baths2,079 sq ft

129 Bloomingdale Ave, Federalsburg, MD 21632

(410) 543-4545

Property at 1204 Blue Heron Dr, Denton, MD 21629, 3 beds, 2.5 baths

$235,000

3 beds2.5 baths1,693 sq ft

1204 Blue Heron Dr, Denton, MD 21629

(443) 992-4990

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3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Welcome to 120 Meadowcroft Drive, where space, style, and your own backyard retreat come together! Offering over 3,100 square feet, this beautifully updated home is designed for both everyday living and entertaining. Step inside to find LVP flooring throughout the main level, fresh finishes, and a spacious, functional layout. The kitchen features quartz countertops, generous workspace, and plenty of room to gather. A main-level office provides the perfect space for working from home. Upstairs, you’ll find four generously sized bedrooms, including a primary suite you won’t want to leave, a spacious retreat designed for relaxing at the end of the day. Upper-level laundry adds ever

$559,999

4 beds2.5 baths3,183 sq ft

120 Meadowcroft Dr, Centreville, MD 21617

Quartz countertops • In-ground pool • Main level office

(443) 274-1900

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
BUYER MUST BE APPROVED FOR PURCHASE BY THE HYDE PARK OFFICE BEFORE SUBMITTING AN OFFER. SUBJECT TO MONTHLY GROUND RENT THAT WILL INCREASE FROM $643 CURRENTLY TO $678 IN NOVEMBER 2026. This 2 bed, 1.5 bath mobile home is priced for quick attention--She's ready for the new owner to put their own fresh touches on her and start writing their next chapter in this thriving and active 55+ community! Pool, clubhouse, new dog park, covered shuffle boards and horseshoe pits means you will never be bored! Convenient to everything you need in 2 miles or less--unbeatable value for all this home and location have to offer.

$89,000

2 beds1.5 baths930 sq ft

6 Albion Ct, Easton, MD 21601

Dog park • Clubhouse • Shuffle boards

(410) 304-2250

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
This spacious 4-bedroom, 3.5-bath home offers a peaceful rural setting just minutes from downtown Easton. Set on 2+/- acres with an additional 5.92+/-acre non-buildable lot included in the sale, the property offers plenty of space both inside and out. The main level features a large living room with a stone-surround gas fireplace, formal dining room, sunroom, and a well-appointed kitchen with stainless steel appliances, and a large island that makes gathering and entertaining easy. A first-floor office or library adds flexibility, while A whole-home Sonos sound system adds another layer of convenience for everyday living and entertaining. Upstairs, the spacious primary suite includes a priv

$1,075,000

4 beds3.5 baths4,062 sq ft

29747 Easton Farms, Easton, MD 21601

Quartz countertops • 5.92 acre lot • 2 acres

(410) 822-6665

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Chesapeake by Del Webb. The Hillsboro model offers an exceptional combination of space, convenience, and comfortable living. Located directly across from the Community Center and pool, this home features more than 3,400 square feet of thoughtfully designed living space. The main level includes two generously sized bedrooms and two full bathrooms, along with a separate office, living room, family room with fireplace, and bright sunroom. Upstairs, you'll find an additional bedroom, full bathroom, and spacious living area—ideal for guests, family members, or a private retreat. Step outside to the rear patio, where extensive landscaping creates a beautiful setting for outdoor entertaining

$559,000

3 beds3 baths3,465 sq ft

29580 Charles Dr, Easton, MD 21601

New hot water heater • Rear patio • Hvac system

(410) 822-1415

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Nestled in the serene enclave of Indian Grant (one of Dorchester's most sought after neighborhoods), this exquisite 5-bedroom, 4-bathroom residence embodies the perfect blend of luxury and comfort. It was built in 1998 by a local, esteemed custom home builder, Thom Huntington. It has recently been thoughtfully renovated. This home showcases a stunning French Colonial architectural style, enhanced by modern amenities and meticulous attention to detail. Step inside to discover an inviting open floor plan that seamlessly connects the living spaces, ideal for both entertaining and everyday living. The gourmet kitchen is a chef's dream, featuring upgraded countertops, a spacious island, an

$799,000

5 beds4 baths4,000 sq ft

3536 Indian Grant Rd, East New Market, MD 21631

Spacious island • Upgraded countertops • Gourmet kitchen

(410) 228-0800

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS QUICK MOVE IN HOME!! Don’t miss this incredible opportunity—3 Car Garage! 4 bedrooms, 3.5 baths, offering exceptional space and value for today’s lifestyle. Backing to trees for added privacy and a serene view, this home delivers both comfort and setting. The bright sunroom off the kitchen creates the perfect gathering space, while the kitchen itself shines with a farmhouse sink, white cabinetry, quartz countertops, and a gourmet stainless steel appliance package with a hood. Luxury vinyl plank flooring spans the main level. Upstairs, enjoy the convenience of a second-level laundry room with a utility sink. Locat

$599,990

4 beds3.5 baths4,025 sq ft

1953 Silver Lake Ln, Trappe, MD 21673

Quartz countertops • Backing to trees • Farmhouse sink

(703) 420-3322

Property at 29796 Lyons Dr, Easton, MD 21601, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths2,729 sq ft

29796 Lyons Dr, Easton, MD 21601

(410) 822-9000

Property at 1566 Vernon Rd, Harrington, DE 19952, 3 beds, 2 baths

$359,900

3 beds2 baths1,400 sq ft

1566 Vernon Rd, Harrington, DE 19952

(302) 273-4998

Property at 29720 Lyons Dr, Easton, MD 21601, 2 beds, 2 baths

$465,000

2 beds2 baths1,940 sq ft

29720 Lyons Dr, Easton, MD 21601

(410) 822-1415

Property at 611 Clark Corners Rd, Centreville, MD 21617, 4 beds, 2.5 baths

$549,987

4 beds2.5 baths2,596 sq ft

611 Clark Corners Rd, Centreville, MD 21617

(443) 249-7653

Property at 29500 Cromwell Ln, Easton, MD 21601, 2 beds, 2 baths

$399,990

2 beds2 baths1,385 sq ft

29500 Cromwell Ln, Easton, MD 21601

(410) 208-3500

Property at 1471 Lake George Ln, Trappe, MD 21673, 5 beds, 3 baths

$411,490

5 beds3 baths— sq ft

1471 Lake George Ln, Trappe, MD 21673

(833) 335-7433

Property at 1951 Silver Lake Ln, Trappe, MD 21673, 4 beds, 3.5 baths

$584,990

4 beds3.5 baths3,432 sq ft

1951 Silver Lake Ln, Trappe, MD 21673

(703) 420-3322

Property at 122 Fair Brook Way, Centreville, MD 21617, 5 beds, 3 baths

$645,000

5 beds3 baths3,452 sq ft

122 Fair Brook Way, Centreville, MD 21617

(443) 274-1900

Property at 29689 Lyons Dr, Easton, MD 21601, 2 beds, 2 baths

$475,000

2 beds2 baths1,878 sq ft

29689 Lyons Dr, Easton, MD 21601

(410) 770-9255

Property at 30420 Deep Branch Rd, Trappe, MD 21673, 3 beds, 3.5 baths

$750,000

3 beds3.5 baths2,594 sq ft

30420 Deep Branch Rd, Trappe, MD 21673

(410) 822-6272

Property at 29833 Hillary Ave, Easton, MD 21601, 3 beds, 3 baths

$495,000

3 beds3 baths2,800 sq ft

29833 Hillary Ave, Easton, MD 21601

(410) 822-6665

Property at 1 Victoria Ct, Easton, MD 21601, 2 beds, 3 baths

$249,500

2 beds3 baths1,300 sq ft

1 Victoria Ct, Easton, MD 21601

(410) 822-6665

Property at 7401 Casey Ave, Easton, MD 21601, 3 beds, 3 baths

$534,900

3 beds3 baths2,342 sq ft

7401 Casey Ave, Easton, MD 21601

(410) 224-2200

Property at 131 Fair Brook Way, Centreville, MD 21617, 4 beds, 3.5 baths

$585,000

4 beds3.5 baths3,508 sq ft

131 Fair Brook Way, Centreville, MD 21617

Homes with Pools for Sale in Caroline County

There are currently 13 homes with pools for sale in Caroline County at a median listing price of $332K. 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, 45 homes have been sold in Caroline County. In addition to houses in Caroline County, there was also 1 condo, 10 townhouses, and 2 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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