Homes with Pools for Sale in Caroline County, MD

18 homes

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ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Welcome to 320 N Main St in the charming town of Greensboro! Step inside and discover a home that immediately invites you to kick off your shoes and stay awhile. Situated on a spacious half-acre lot, this 3-bedroom, 2.5-bath home offers the perfect blend of comfort, functionality, and style. The beautifully updated kitchen is sure to impress, featuring a five-burner gas range, stainless steel appliances, farmhouse sink, and granite countertops. The kitchen opens seamlessly to the dining area and spacious living room, creating a wonderful flow for everyday living and entertaining. Upstairs, you'll find the home's private sleeping quarters. The primary suite features an en-suite bathroom and

$389,900

3 beds2 baths1,816 sq ft

320 N Main St, Greensboro, MD 21639

Farmhouse sink • Updated kitchen • Granite countertops

(410) 827-4663

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Be sure to schedule a tour of this beautiful home in the heart of Denton, small town living at it's best! Built in 1916 and lovingly updated and maintained throughout the years! Beautiful hardwood floors throughout! Lovely updated custom kitchen with soaring vaulted ceilings, radiant heat flooring, walk in pantry, recessed lighting, farm sink and granite counter tops. Mud room with built-in storage and slide out shelving. Replacement windows, mini-split in TV room heats and cools the downstairs, leaded mahogany front door and lovely entry foyer leads to a formal living room. Upstairs you will find three gracious sized bedrooms, a full bath with jacuzzi style tub and laundry room with new

$467,900

3 beds2 baths2,318 sq ft

104 Riverton Ave, Denton, MD 21629

Custom kitchen • Vaulted ceilings • Walk in pantry

(410) 479-3993

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Welcome to 107 Sunset Blvd in Preston, MD! This spacious 3-bedroom, 2.5-bath brick home offers comfortable living, thoughtful updates, and everyday convenience. The inviting interior features an open living and dining area with plenty of room to gather, entertain, and make yourself at home. Newer LVP flooring, fresh paint, and upgraded recessed lighting create a clean, modern feel throughout the main living spaces. The kitchen features new appliances installed approximately one year ago, while the master bathroom and electric heat pump were replaced within the last year. Additional updates include new exterior doors, upgraded ceiling fans, and a hall bathroom remodel completed within the la

$375,000

3 beds2.5 baths1,736 sq ft

107 Sunset Blvd, Preston, MD 21655

New exterior doors • New appliances • 0.39 acre lot

(410) 543-4545

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

$549,900

3 beds2.5 baths2,769 sq ft

7884 Laurel Ln, Denton, MD 21629

Private acres • Finished bonus room • Sunken family room

(410) 476-2201

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
* Major Price Improvement * * * Thoughtfully Renovated & Move-In Ready * * Welcome to a beautifully renovated home offering 3 bedrooms plus a flexible bonus space with potential for a 4th bedroom in the water front community of Two Johns. Extensively updated from top to bottom, this home offers a fresh, modern feel while maintaining a warm and inviting atmosphere. As you enter, you’ll immediately notice the all-new flooring and lighting throughout, freshly painted rooms, new interior doors, and crown molding featured in most spaces, creating a clean and cohesive look throughout the home. The updated kitchen combines style and functionality with beautiful quartz countertops

$568,900

3 beds3 baths2,343 sq ft

7737 Westerly Dr, Preston, MD 21655

1.07 acre lot • 2 garage spots • Pool

(410) 972-4000

Property at 3325 Sharon Ct, Federalsburg, MD 21632, 3 beds, 1.5 baths

$335,000

3 beds1.5 baths1,396 sq ft

3325 Sharon Ct, Federalsburg, MD 21632

(302) 856-1458

Property at 22733 Squire Ln, Queen Anne, MD 21657, 4 beds, 2.5 baths

$575,000

4 beds2.5 baths2,854 sq ft

22733 Squire Ln, Queen Anne, MD 21657

(410) 643-2244

Property at 25722 Old Mill Ln, Greensboro, MD 21639, 4 beds, 3.5 baths

$649,997

4 beds3.5 baths2,758 sq ft

25722 Old Mill Ln, Greensboro, MD 21639

(443) 320-1344

Property at 4 N Maryland Ave, Ridgely, MD 21660, 4 beds, 2.5 baths

$375,000

4 beds2.5 baths2,552 sq ft

4 N Maryland Ave, Ridgely, MD 21660

(302) 360-0300

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

$1,250,000

4 beds3 baths3,358 sq ft

23071 Tuckahoe Springs Dr, Denton, MD 21629

(410) 228-2525

Property at 1624 Blue Heron Dr, Denton, MD 21629, 4 beds, 3.5 baths

$289,900

4 beds3.5 baths2,280 sq ft

1624 Blue Heron Dr, Denton, MD 21629

(410) 643-4131

Property at 412 N Main St, Greensboro, MD 21639, 3 beds, 2 baths

$359,900

3 beds2 baths2,160 sq ft

412 N Main St, Greensboro, MD 21639

(302) 677-0020

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

$385,000

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

$324,900

3 beds2 baths1,414 sq ft

504 Main St, Goldsboro, MD 21636

(302) 217-6692

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

$230,000

3 beds2.5 baths1,693 sq ft

1204 Blue Heron Dr, Denton, MD 21629

(443) 992-4990

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ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Nestled in the charming Mulberry Station community, this delightful traditional home offers a perfect blend of comfort and style. A thoughtfully designed living space, ideal for creating lasting memories awaits you. Step inside to discover a warm and inviting interior featuring beautiful wood floors that flow seamlessly throughout the main living areas. The kitchen is equipped with modern stainless steel appliances, including a built-in microwave, dishwasher, and electric oven/range, ensuring that meal preparation is a breeze. A charming breakfast area invites you to enjoy your morning coffee while overlooking the serene backyard. The family room, conveniently located off the kitchen, featu

$489,900

4 beds2.5 baths2,094 sq ft

8862 Roundhouse Cir, Easton, MD 21601

Separate dining room • Walk-in closet • Gas fireplace

(410) 822-9000

OPEN SUN, 2PM TO 4PM

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, DE:
Welcome to 3494 Woodpecker Rd, a spacious ranch-style home offering comfortable one-level living in a quiet Seaford setting. This 3-bedroom, 2-bath home features an oversized primary suite complete with a walk-in closet and ensuite bathroom with both a soaking tub and separate stall shower. Ample storage throughout the home, along with a dedicated laundry room, adds everyday convenience. The attached two-car garage provides additional storage and parking, while solar panels offer an energy-conscious feature. Outside, enjoy an in-ground pool, hot tub, and pavilion—creating an inviting space for relaxing or entertaining. A detached storage building provides even more room for equipment,

$390,000

3 beds2 baths1,640 sq ft

3494 Woodpecker Rd, Seaford, DE 19973

Soaking tub • Walk in closet • Ensuite bathroom

(302) 856-1458

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Bring your vision and your renovation plans to 9144 Honeysuckle Drive in Easton! This three-bedroom, one-bath split-foyer home is being offered at $250,000 and presents an opportunity for investors, contractors, or buyers looking to create a home tailored to their own style. The property needs a full rehab, but the potential is here. The existing layout offers three bedrooms, one full bath, and the versatility of a split-foyer design. Out back, an in-ground swimming pool adds an attractive feature that could become the centerpiece of the finished property. Located in Easton, this property offers the opportunity to transform an existing home into something special while taking advantage of t

$250,000

3 beds1 bath2,394 sq ft

9144 Honeysuckle Dr, Easton, MD 21601

Split-foyer design • 0.26 acre lot • 2 parking spots

(888) 860-7369

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
ONLINE AUCTION: Bidding begins 10/08/2026 @ 10:00 AM. Bidding ends 10/12/2026 @ 11:50 AM. List Price is Suggested Opening Bid. Deposit: $5,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Mobile Home located in the Active 55+ Hyde Park Community in Talbot County. Enjoy the convenience of Easton's historic downtown, dining, shopping and arts scene. Easy access to parks, trails and the Tred Avon River. Easy access to major traffic artery US-50 (Ocean Gateway). Property is vacant.

$30,000

2 beds2 baths1,568 sq ft

64 Park Ln, Easton, MD 21601

Easy access to parks • 2 parking spots • Community pool

(410) 488-3124

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, MD:
Chesapeake by Del Webb. Gorgeous McDaniel style home has been remodeled with many upgrades in the past 4 years. Living room/office, formal dining room, family room with gas fireplace, open kitchen with new appliances and granite countertops, breakfast area, large sunroom with tile flooring overlooking paver patio with exterior lighting, powder room, 1st floor primary suite with totally renovated bath with custom tile, free standing tub and walk-in shower. 2nd floor offers loft, 2 guest bedrooms, renovated bath and walk-in attic storage. 2 car rear loading attached garage, lawn irrigation system and house security system. Roof and gutters (2020, previous owners), stainless appliances and gra

$550,000

3 beds2.5 baths3,098 sq ft

29574 Charles Dr, Easton, MD 21601

Custom tile • Free standing tub • Granite countertops

(410) 822-1415

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Caroline County, DE:
5 ACRES • 3 PARCELS • 1 EXISTING HOME • ENDLESS POSSIBILITIES! This unique listing combines 3 separate parcels being sold together as 1 package, totaling approximately 5.04 acres! The main residence sits on 2.5 acres, with an additional 1.85-acre flag lot to the left and a . 69-acre lot to the right. Whether you're looking for extra privacy, room for hobbies and recreation, or the opportunity to build a Family Compound, this property provides a rare amount of land in a convenient Hartly location. This 4-bedroom, 2-full-bath Split-Level home with 600 SqFt 2-car garage greets you with a long teardrop driveway complete with its own garden circle. The eat-in kitchen is built for

$570,000

4 beds2 baths2,084 sq ft

1435 Hourglass Rd, Hartly, DE 19953

3 parcels • Open concept • Private bath

(302) 504-6147

Property at 2700 Willow Oak Dr Unit 310C, Cambridge, MD 21613, 2 beds, 2 baths

$395,000

2 beds2 baths1,519 sq ft

2700 Willow Oak Dr Unit 310C, Cambridge, MD 21613

(888) 860-7369

Property at 3506 Aeberle Rd, East New Market, MD 21631, 2 beds, 1 bath

$329,000

2 beds1 bath1,245 sq ft

3506 Aeberle Rd, East New Market, MD 21631

(410) 822-6665

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 213 S Paula Lynne Dr, Seaford, DE 19973, 3 beds, 2.5 baths

$385,000

3 beds2.5 baths1,948 sq ft

213 S Paula Lynne Dr, Seaford, DE 19973

(302) 629-5575

Property at 29812 Dustin Ave, Easton, MD 21601, 3 beds, 2.5 baths

$480,000

3 beds2.5 baths3,098 sq ft

29812 Dustin Ave, Easton, MD 21601

(410) 770-9255

Property at 6 Albion Ct, Easton, MD 21601, 2 beds, 1.5 baths

$89,000

2 beds1.5 baths930 sq ft

6 Albion Ct, Easton, MD 21601

(410) 304-2250

Property at 29747 Easton Farms, Easton, MD 21601, 4 beds, 3.5 baths

$995,000

4 beds3.5 baths6,337 sq ft

29747 Easton Farms, Easton, MD 21601

(410) 822-6665

Property at 29580 Charles Dr, Easton, MD 21601, 3 beds, 3 baths

$499,900

3 beds3 baths3,465 sq ft

29580 Charles Dr, Easton, MD 21601

(410) 822-1415

Property at 1953 Silver Lake Ln, Trappe, MD 21673, 4 beds, 3.5 baths

$599,990

4 beds3.5 baths4,025 sq ft

1953 Silver Lake Ln, Trappe, MD 21673

(703) 420-3322

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

$399,990

5 beds3 baths— sq ft

1471 Lake George Ln, Trappe, MD 21673

(833) 335-7433

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

$459,900

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 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 18 homes with pools for sale in Caroline County at a median listing price of $331K. 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 78 days and receive 2 offers. This map is refreshed with the newest listings in Caroline County every 15 minutes.

In the past month, 32 homes have been sold in Caroline County. In addition to houses in Caroline County, there was also 1 condo, 9 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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