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Newest Eastern Shore Listings

9 Chesapeake Cir, Earleville image
9 Chesapeake Cir, Earleville $589,000

COMING SOON - Chesapeake Bay Views in Earleville! Enjoy breathtaking, unobstructed views of the Chesapeake Bay in the popular water-oriented community of Bay View Estates...

  • 3 Beds
  • 2 Baths
  • MDCC2023726 MLS
8014 Gosling Pond Ct, St Michaels image
8014 Gosling Pond Ct, St Michaels $775,000

Beautifully situated on an exceptional lot overlooking a picturesque pond, this spacious home in the desirable Back Creek Landing community offers gorgeous sunset views, ...

  • 4 Beds
  • 3 Baths
  • MDTA2015458 MLS
5 S Park St S, Easton image
5 S Park St S, Easton $575,000

This stunning Bungalow with a seperate commercial rental was beautifully renovated in 2020 and offers a perfect blend of modern luxury and timeless charm. With 1,168 sq. ...

  • 3 Beds
  • 3 Baths
  • MDTA2015526 MLS
14971 Cherry Ln, Ridgely image
14971 Cherry Ln, Ridgely $699,900

TWO HOMES, NEARLY 2.5 ACRES, AND AN IMPRESSIVE 30’ X 60’ DETACHED GARAGE! A truly unique opportunity awaits at 14971 Cherry Lane in Ridgely! Situated on 2.42 acres, this ...

  • 6 Beds
  • 3 Baths
  • MDCM2008044 MLS
property image
9789 Pearson Rd, Denton $234,900

None

  • 3 Beds
  • 2 Baths
  • MDCM2008070 MLS
200 High Thicket Ln, Stevensville image
200 High Thicket Ln, Stevensville $1,800,000

A RARE OPPORTUNITY TO OWN OVER 17 SPRAWLING ACRES ON KENT ISLAND! Discover the beauty, privacy, and endless possibilities of this extraordinary estate nestled in the pict...

  • 4 Beds
  • 4 Baths
  • MDQA2019206 MLS
227 New St, Church Hill image
227 New St, Church Hill $339,900

Coming Soon - You won't want to miss this one. Fully renovated home in the heart of Church Hill. New everything - new roof, windows, doors, flooring, kitchen, bathrooms, ...

  • 3 Beds
  • 2 Baths
  • MDQA2019210 MLS
331 Utah Rd, Stevensville image
331 Utah Rd, Stevensville $420,000

Welcome to 331 Utah Rd. This well-maintained home is being offered for the first time and is conveniently located so close to the water in Kent Island Estates. Featuring ...

  • 3 Beds
  • 2 Baths
  • MDQA2019172 MLS
25468 Auction Rd, Denton image
25468 Auction Rd, Denton $80,000

ONLINE AUCTION: Bidding begins 11/12/2026 @ 10:00 AM. Bidding ends 11/16/2026 @ 11:00 AM. List Price is Suggested Opening Bid. Deposit: $15,000. This auction takes place ...

  • 3 Beds
  • 1 Baths
  • MDCM2008066 MLS
727 Warbler Way, Chester image
727 Warbler Way, Chester $979,990

Welcome to the Mykonos, a beautifully designed home that blends an open-concept floorplan with Classic-inspired style, creating the perfect balance of comfort and functio...

  • 4 Beds
  • 4 Baths
  • MDQA2019208 MLS
3881 Laurel Grove Rd, Federalsburg image
3881 Laurel Grove Rd, Federalsburg $699,000

YOUR OWN PRIVATE RETREAT ON NEARLY 7 ACRES — WHERE COUNTRY CHARM MEETS COMFORT, SPACE, AND ENDLESS POSSIBILITIES! Welcome to 3881 Laurel Grove Road, an inviting Colonial...

  • 4 Beds
  • 3 Baths
  • MDCM2008064 MLS
244 Warbler Way, Chester image
244 Warbler Way, Chester $700,000

Welcome to 244 Warbler Way, a beautifully appointed Jenkins model built in 2025 and located in the sought-after 55+ community of Four Seasons at Kent Island. This thought...

  • 2 Beds
  • 2 Baths
  • MDQA2019196 MLS
111 Kent St S, Chestertown image
111 Kent St S, Chestertown $450,000

Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this ...

  • 2 Beds
  • 3 Baths
  • MDKE2007120 MLS
214 Penny Ln, Stevensville image
214 Penny Ln, Stevensville $499,900

A short stroll from the Eastern Bay front community center, this brand new home is complete and ready for you to move in before the holidays! One level living with LVP f...

  • 3 Beds
  • 2 Baths
  • MDQA2019204 MLS
7004 Beulah Rd, Hurlock image
7004 Beulah Rd, Hurlock $299,900

Country Charm Meets Modern Comfort! Welcome to 7004 Beulah Road in Hurlock, MD! This beautifully remodeled 3-bedroom, 2-bath home offers the perfect blend of peaceful cou...

  • 3 Beds
  • 2 Baths
  • MDDO2013464 MLS
403 Calvert St, Chestertown image
403 Calvert St, Chestertown $135,000

INVESTOR OPPORTUNITY! Come see this 3-bedroom, 1.5-bath townhome offering great potential to add to your portfolio! Recent improvements include drywall replacement, newly...

  • 3 Beds
  • 2 Baths
  • MDKE2007244 MLS
200 Anchor Ln, Chester image
200 Anchor Ln, Chester $559,900

Welcome to 200 Anchor Lane, where the charm of an established Kent Island neighborhood meets the convenience of a nearly new home! Situated on a spacious 0.42-acre corner...

  • 3 Beds
  • 2 Baths
  • MDQA2019192 MLS
8710 Cummings Rd, Wittman image
8710 Cummings Rd, Wittman $1,285,000

Well maintained one level living on Cummings Creek. 3 BR's, 2.5 baths, DR, kitchen, waterside living room, 2 car garage, oversized screen porch. Beautiful Westerly sunset...

  • 3 Beds
  • 3 Baths
  • MDTA2015520 MLS
18 Sugar Dr, East New Market image
18 Sugar Dr, East New Market $375,000

Welcome to 18 Sugar Dr, where a breezy front porch, spacious layout, and inviting backyard make it easy to feel at home! Recently painted and featuring vinyl plank floori...

  • 4 Beds
  • 3 Baths
  • MDDO2013468 MLS
302 W Oak Ave, Easton image
302 W Oak Ave, Easton — Easton $269,500

Traditional one-story living in great location off S. Washington Street close to Idlewild Park. Hardwood floors, separate laundry room. Picture window in living room. Spa...

  • 2 Beds
  • 1 Baths
  • MDTA2015512 MLS
  • Easton Bldg.
201 Garland Way, Chestertown image
201 Garland Way, Chestertown $375,000

Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of pote...

  • 4 Beds
  • 3 Baths
  • MDKE2007232 MLS
190 Harrier Way Unit 24, Chester image
190 Harrier Way Unit 24, Chester $675,000

Designed for effortless, low-maintenance living, this beautifully appointed three-bedroom, 2.5-bath condominium offers approximately 2,600 square feet of thoughtfully des...

  • 3 Beds
  • 3 Baths
  • MDQA2019194 MLS
6522 Cabin Creek Rd, Hurlock image
6522 Cabin Creek Rd, Hurlock $240,000

Freshly remodeled and ready for its new owner! This 3-bedroom, 2-bathroom manufactured home features new cabinetry, flooring, stainless steel appliances, siding, windows,...

  • 3 Beds
  • 2 Baths
  • MDDO2013462 MLS
377 Hemsley Dr, Queenstown image
377 Hemsley Dr, Queenstown $1,775,000

Exceptional Wye River Waterfront Living – A Boater’s Paradise! An extraordinary opportunity to enjoy the very best of Wye River waterfront living! Perfectly positioned a...

  • 4 Beds
  • 4 Baths
  • MDQA2019178 MLS
Ocean Gtwy, Trappe image
Ocean Gtwy, Trappe $27,000

None

  • MDTA2015518 MLS

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Eastern Shore Md Real Estate is our Specialty. We Realize Searching for a New home can be overwhelming. So we wanted to offer an Easy one stop shop of a Real Estate Search Website that has big clear pictures to view, loads fast, super Easy to use and Navigate through and keeps you informed at all times on New homes listed in your areas as well as price reductions on properties to give you that advantage of deals before everyone else. We Specialize in helping people find their dream property here on the Eastern Shore, Queen Anne's, Kent, Talbot, Caroline and Cecil are our main areas of focus we service best.

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Taylor Properties
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