Homes with Pools for Sale in Talbot County, MD

305 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Talbot County, MD:
Waterfront Retreat in Cookes Hope - Located in the highly desirable Oxford Road corridor, this custom waterfront home in Cookes Hope offers a perfect balance of elegance and comfort with breathtaking water views and thoughtfully designed living spaces by Pam Gardner. With 3 bedrooms, 2.5 baths, and a one-level open floor plan, this home is ideal for relaxed waterfront living. A two-story foyer leads into the expansive family room, where vaulted ceilings, skylights, wood floors, and a striking catwalk create a bright and airy atmosphere, perfectly framing the stunning waterfront backdrop. The waterside primary suite offers a private retreat with a fireplace, custom bath featuring a steam s

$1,695,000

4 beds3.5 baths3,400 sq ft

6780 Cookes Hope Rd, Easton, MD 21601

1.9 acre lot • 2 garage spots • Built 2001

(410) 673-3344

SHORT SALE

ABOUT THIS HOME
Home with a Pool for sale in Talbot County, MD:
Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a spacious main-level layout designed to impress. The expansive living room is flooded with natural light and flanked by a formal dining area, a warm and inviting den, and a breakfast nook with vaulted ceilings—all connected by elegant sight lines and polished hardwoods. A true chef

$1,200,000

5 beds2.5 baths4,214 sq ft

5520 Leeward Ln, Tilghman, MD 21671

1.19 acre lot • 3 garage spots • Built 2005

(302) 360-0300

ABOUT THIS HOME
Home with a Pool for sale in Talbot County, MD:
Extremely well maintained Skipton Estates colonial. Situated on a wooded 2 acre lot which offers loads of privacy. This home offers a 1st floor primary with 3 additional bedrooms on 2nd floor as well as a spacious bonus room. Formal living and dining rooms, perfect kitchen for entertaining with bar area and center island, oversized family room with gas fireplace and large rear deck. More features and photos to come.

$865,000

4 beds3.5 baths3,740 sq ft

29583 Skipton Estates Dr, Cordova, MD 21625

2 acre lot • 3 garage spots • Built 2006

(410) 822-6665

ABOUT THIS HOME
Home with a Pool for sale in Talbot County, MD:
Welcome to your spacious and beautifully upgraded home in The Woods at Stoney Ridge—one of Easton’s most desirable neighborhoods. This stunning 3-bedroom, 2.5-bath Colonial is ideally situated on a quiet cul-de-sac and offers an ideal blend of timeless charm, modern amenities, and functional living. Inside, a traditional floor plan unfolds with inviting spaces that include a formal dining room, a bright kitchen, a comfortable family room, a versatile office or bonus room, and the convenience of a first-floor laundry. Upstairs, the expansive primary suite is a true retreat, featuring a spa-inspired bath complete with a soaking tub, walk-in shower, and dual-sink vanity. Two additi

$439,000

3 beds2.5 baths1,825 sq ft

7144 Fir St, Easton, MD 21601

Bright kitchen • Formal dining room • Upgraded home

(302) 360-0300

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Talbot County, MD:
Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oa

$7,500,000

5 beds5 baths10,000 sq ft

7090 Cooper Point Rd, Bozman, MD 21612

Waterfront estate • Landscaped acres • Sweeping views

(410) 673-3344

Property at 6403 Bozman Neavitt Rd, Neavitt, MD 21652, 3 beds, 2 baths

$469,500

3 beds2 baths1,834 sq ft

6403 Bozman Neavitt Rd, Neavitt, MD 21652

(410) 745-2596

Property at 110 N Morris St N, Oxford, MD 21654, 5 beds, 5.5 baths

$1,295,000

5 beds5.5 baths3,574 sq ft

110 N Morris St N, Oxford, MD 21654

(410) 822-1415

Property at 8000 Bozman Neavitt Rd, Bozman, MD 21612, 3 beds, 2 baths

$585,000

3 beds2 baths1,761 sq ft

8000 Bozman Neavitt Rd, Bozman, MD 21612

(410) 745-0415

Property at 8620 Bozman Neavitt, Saint Michaels, MD 21663, 6 beds, 9 baths

$8,495,000

6 beds9 baths17,402 sq ft

8620 Bozman Neavitt, Saint Michaels, MD 21663

(202) 944-5000

Property at 22349 Cooper Ln, Wittman, MD 21676, 2 beds, 1 bath

$245,000

2 beds1 bath1,270 sq ft

22349 Cooper Ln, Wittman, MD 21676

(410) 822-6665

Property at 29638 Janets Way, Easton, MD 21601, 3 beds, 3 baths

$525,000

3 beds3 baths2,342 sq ft

29638 Janets Way, Easton, MD 21601

(410) 266-0600

Property at Lot 16 North, Easton, MD 21601, 3 beds, 2.5 baths

$780,000

3 beds2.5 baths2,065 sq ft

Lot 16 North, Easton, MD 21601

(410) 822-6272

Property at 24362 Widgeon Pl #4, Saint Michaels, MD 21663, 2 beds, 2.5 baths

$349,000

2 beds2.5 baths1,800 sq ft

24362 Widgeon Pl #4, Saint Michaels, MD 21663

(410) 822-6272

Property at 13 Sandy Ln, Easton, MD 21601, 3 beds, 2 baths

$659,000

3 beds2 baths1,606 sq ft

13 Sandy Ln, Easton, MD 21601

(410) 745-0415

Property at 26546 Presquile Dr, Easton, MD 21601, 7 beds, 7 baths

$8,400,000

7 beds7 baths8,001 sq ft

26546 Presquile Dr, Easton, MD 21601

(410) 822-6272

Property at 29031 Howell Point Rd, Trappe, MD 21673, 4 beds, 3 baths

$11,500,000

4 beds3 baths9,833 sq ft

29031 Howell Point Rd, Trappe, MD 21673

(410) 524-7700

Property at 8062 N Fork Blvd, Easton, MD 21601, 3 beds, 2.5 baths

$729,500

3 beds2.5 baths2,184 sq ft

8062 N Fork Blvd, Easton, MD 21601

Property at 7651 Main St, Sherwood, MD 21665, 2 beds, 2 baths

$425,000

2 beds2 baths1,776 sq ft

7651 Main St, Sherwood, MD 21665

(410) 745-0283

Property at 1674 Lake Placid Dr, Trappe, MD 21673, 4 beds, 2.5 baths

$365,690

4 beds2.5 baths1,990 sq ft

1674 Lake Placid Dr, Trappe, MD 21673

Listing provided by Zillow

Property at 28028 Playtor Rd, Easton, MD 21601, 4 beds, 3.5 baths

$1,250,000

4 beds3.5 baths4,443 sq ft

28028 Playtor Rd, Easton, MD 21601

(410) 770-9255

Property at 21477 Island Club Rd, Tilghman, MD 21671, 4 beds, 2.5 baths

$1,200,000

4 beds2.5 baths3,040 sq ft

21477 Island Club Rd, Tilghman, MD 21671

(410) 745-2596

Property at 5654 Trafalgar Cir, Tilghman, MD 21671, 3 beds, 2 baths

$499,888

3 beds2 baths1,710 sq ft

5654 Trafalgar Cir, Tilghman, MD 21671

(410) 745-0415

Property at 29 Kensington Dr, Easton, MD 21601, 2 beds, 2.5 baths

$229,000

2 beds2.5 baths1,887 sq ft

29 Kensington Dr, Easton, MD 21601

(410) 745-0415

Property at 6394 Bozman Neavitt Rd, Neavitt, MD 21652, 2 beds, 2 baths

$550,000

2 beds2 baths1,570 sq ft

6394 Bozman Neavitt Rd, Neavitt, MD 21652

(410) 745-2596

Property at 133 N Washington St, Easton, MD 21601

$850,000

— beds— baths2,875 sq ft

133 N Washington St, Easton, MD 21601

(410) 822-1415

Property at 6827 Bellevue Rd, Royal Oak, MD 21662, 3 beds, 1.5 baths

$385,000

3 beds1.5 baths1,363 sq ft

6827 Bellevue Rd, Royal Oak, MD 21662

(410) 429-7425

Property at 7849 Ward Brothers Cir, Easton, MD 21601, 3 beds, 2.5 baths

$499,990

3 beds2.5 baths1,978 sq ft

7849 Ward Brothers Cir, Easton, MD 21601

(240) 375-5074

Property at 10380 Chapel Rd, Easton, MD 21601, 5 beds, 3 baths

$1,450,000

5 beds3 baths3,878 sq ft

10380 Chapel Rd, Easton, MD 21601

(410) 934-3478

Property at 21948 Main St, Hillsboro, MD 21641, 3 beds, 1 bath

$189,900

3 beds1 bath1,904 sq ft

21948 Main St, Hillsboro, MD 21641

(410) 479-3993

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

$443,900

2 beds2 baths1,385 sq ft

29500 Cromwell Ln, Easton, MD 21601

(240) 375-5074

Property at 6119 Country Club Dr, Easton, MD 21601, 3 beds, 3 baths

$1,895,000

3 beds3 baths2,568 sq ft

6119 Country Club Dr, Easton, MD 21601

(410) 822-6665

Property at 29244 Corbin Pkwy, Easton, MD 21601, 3 beds, 2 baths

$359,000

3 beds2 baths2,200 sq ft

29244 Corbin Pkwy, Easton, MD 21601

(410) 822-6665

Property at 28477 Wedgeway Cir, Easton, MD 21601, 3 beds, 2.5 baths

$649,000

3 beds2.5 baths2,044 sq ft

28477 Wedgeway Cir, Easton, MD 21601

(443) 249-7653

Property at 6135 Summit St, Tilghman, MD 21671, 2 beds, 1 bath

$365,000

2 beds1 bath864 sq ft

6135 Summit St, Tilghman, MD 21671

(410) 714-9166

Property at 24749 Swan Rd, St Michaels, MD 21663, 3 beds, 2.5 baths

$650,000

3 beds2.5 baths2,496 sq ft

24749 Swan Rd, St Michaels, MD 21663

(410) 745-0415

Property at 11340 Longwoods Rd, Easton, MD 21601, 3 beds, 2 baths

$799,999

3 beds2 baths1,822 sq ft

11340 Longwoods Rd, Easton, MD 21601

(410) 822-6272

Property at 13 N Thoroughgood Ln #24, Easton, MD 21601, 2 beds, 2.5 baths

$339,900

2 beds2.5 baths1,340 sq ft

13 N Thoroughgood Ln #24, Easton, MD 21601

(410) 255-3690

Property at 4957 Bar Neck Rd, Tilghman, MD 21671, 3 beds, 3 baths

$699,900

3 beds3 baths2,660 sq ft

4957 Bar Neck Rd, Tilghman, MD 21671

(410) 729-7700

Property at 300 Dixon St #303, Easton, MD 21601, 3 beds, 2.5 baths

$379,700

3 beds2.5 baths2,000 sq ft

300 Dixon St #303, Easton, MD 21601

(410) 263-3400

Property at 22860 Middle Point Rd, Neavitt, MD 21652, 3 beds, 2 baths

$1,150,000

3 beds2 baths2,642 sq ft

22860 Middle Point Rd, Neavitt, MD 21652

(410) 745-0415

Property at 8745 Harper Way, Easton, MD 21601, 3 beds, 2 baths

$461,990

3 beds2 baths1,905 sq ft

8745 Harper Way, Easton, MD 21601

(301) 407-2600

Viewing page 4 of 8

Homes with Pools for Sale in Talbot County

There are currently 305 homes with pools for sale in Talbot County at a median listing price of $535K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Talbot County stay on the market for 102 days and receive 1 offers. This map is refreshed with the newest listings in Talbot County every 15 minutes.

In the past month, 52 homes have been sold in Talbot County. In addition to houses in Talbot County, there was also 1 condo, 35 townhouses, and 5 multi-family units for sale in Talbot County last month. Find your dream home in Talbot 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 Talbot County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Talbot County. If you're looking to sell your home in the Talbot County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Talbot 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 Talbot County, MD

More to explore in Talbot County, MD

How to buy a house in Talbot 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.

Homes with Pools for Sale in Talbot County, MD

Homes with Pools for Sale in Talbot County

More real estate resources for Talbot County, MD

Nearby Counties

Cities

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in Talbot County, MD

How to buy a house in Talbot County, MD

Popular Markets in Maryland