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Newest Eastern Shore Listings

249 Island Lark Way, Chestertown image
249 Island Lark Way, Chestertown $259,900

Interior Pictures Coming Soon! Fantastic opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in The Village of Chestertown, offered at a price that i...

  • 3 Beds
  • 3 Baths
  • MDKE2006972 MLS
414 Church St, Sudlersville image
414 Church St, Sudlersville $435,000

Welcome to this beautifully maintained `three-bedroom, two-bathroom home, built in 2021 and offering a like-new feeling. The thoughtfully designed interior features moder...

  • 3 Beds
  • 2 Baths
  • MDQA2018328 MLS
109 Walnut St, Ridgely image
109 Walnut St, Ridgely $419,000

If you've been dreaming of peaceful country living without giving up the convenience of town, this beautifully maintained Colonial in the desirable Lister Estates communi...

  • 5 Beds
  • 3 Baths
  • MDCM2007764 MLS
2321 Millington, Millington image
2321 Millington, Millington $1,200,000

COMING SOON - Rare opportunity to own TWO homes, an impressive 4,800+ sq. ft. shop, additional pole barn, and 25+ acres—all just minutes from Route 301! The heated and i...

  • 6 Beds
  • 5 Baths
  • MDQA2018348 MLS
330 Prospect Bay Dr W, Grasonville image
330 Prospect Bay Dr W, Grasonville $899,000

Beautiful home in Prospect Bay community. Five bedrooms, three on the main floor and two on the second level. Modern kitchen perfect for entertaining. New roof (2021), ne...

  • 5 Beds
  • 3 Baths
  • MDQA2018104 MLS
2792 Meadowbrook Rd, Federalsburg image
2792 Meadowbrook Rd, Federalsburg $325,000

PROFESSIONAL PHOTOS COMING SOON! Space, flexibility, and outdoor living come together at 2792 Meadowbrook Road! This spacious 5-bedroom, 2.5-bath split-level home sits o...

  • 5 Beds
  • 3 Baths
  • MDCM2007762 MLS
207 Thomas White Blvd, Chester image
207 Thomas White Blvd, Chester $819,900

Located in the sought-after waterfront community of Gibson’s Grant, this beautiful Koch Homes property features the popular Ashford model, with a first-floor Primary Bedr...

  • 3 Beds
  • 3 Baths
  • MDQA2018222 MLS
30300 Kings Meadow Pl, Easton image
30300 Kings Meadow Pl, Easton $775,000

Welcome to 30300 Kings Meadow Place! This spacious home is what peaceful country living is all about! Located on 1.5 acres just outside Easton town limits, you will enj...

  • 4 Beds
  • 4 Baths
  • MDTA2014836 MLS
478 Eagle Manor Dr, Church Hill image
478 Eagle Manor Dr, Church Hill $699,500

COMING SOON! This exceptional 4-bedroom, 2.5-bath custom home offers a level of thoughtful design, upgrades, and attention to detail that truly sets it apart. Located on ...

  • 4 Beds
  • 3 Baths
  • MDQA2018344 MLS
1003 Twin Ct, Chestertown image
1003 Twin Ct, Chestertown $524,900

Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renov...

  • 3 Beds
  • 3 Baths
  • MDKE2006974 MLS
111 Chesapeake Ave, Saint Michaels image
111 Chesapeake Ave, Saint Michaels $949,000

Beautifully upgraded and thoughtfully designed, this home showcases designer‑selected wallpapers, custom finishes, and every modern convenience. The gourmet kitchen featu...

  • 4 Beds
  • 3 Baths
  • MDTA2014834 MLS
123 Trafford Dr, Chestertown image
123 Trafford Dr, Chestertown $375,000

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for...

  • 4 Beds
  • 3 Baths
  • MDKE2006970 MLS
111 Chestnut Rd, Stevensville image
111 Chestnut Rd, Stevensville $499,900

BRAND NEW HOME ON KENT ISLAND for under $500,000! Ready to move in! Located in Chesapeake Estates! Shorter drive to Route 50 than most other new construction on Kent I...

  • 3 Beds
  • 3 Baths
  • MDQA2018340 MLS
305 E Water St, Centreville image
305 E Water St, Centreville $450,000

Mixed-use commercial property offering exceptional exposure in a sought-after location. The first floor commercial space features about 1800+ sq' separated between a lar...

  • 2 Beds
  • 3 Baths
  • MDQA2018338 MLS
158 Wright St, Preston image
158 Wright St, Preston $235,000

Bring your vision and make this spacious Preston home your own! Offering more than 1,800 square feet, this property features three bedrooms, two full bathrooms, and plent...

  • 3 Beds
  • 2 Baths
  • MDCM2007746 MLS
4300 Main, Grasonville image
4300 Main, Grasonville $459,000

Location, Location, Location! This GVC zoned property offers multiple possibilities to both investors and businesses located across from Grasonville Post Office. Perfect ...

  • 1 Baths
  • MDQA2018336 MLS
925 Riverview Terrace, Saint Michaels image
925 Riverview Terrace, Saint Michaels $1,190,000

Presenting 925 Riverview Terrace, a move in ready, charming home ideally located in the sought after Bently Hay neighborhood just minutes from historic downtown St. Micha...

  • 3 Beds
  • 3 Baths
  • MDTA2014744 MLS
3968 Burrsville Rd, Harrington image
3968 Burrsville Rd, Harrington $446,375

Your Country Dream Starts Here Welcome home to country living at its best! This spacious 4 bedroom, 2 bathroom ranch offers over 2,600 sq. ft. of finished living space, ...

  • 4 Beds
  • 2 Baths
  • DEKT2047920 MLS
108 Wall St, Queenstown image
108 Wall St, Queenstown $349,900

Welcome to this adorable cottage on a quarter acre lot that was completely renovated last year! A MUST-SEE! 2 bedroom, 2 full baths, PLUS DEN/ office that can be used as ...

  • 2 Beds
  • 2 Baths
  • MDQA2018320 MLS
14671 Fox Chase Cir, Ridgely image
14671 Fox Chase Cir, Ridgely $345,000

Welcome to this spacious ranch-style home situated on approximately 1.98 private, wooded acres, offering an exceptional combination of space, privacy, and versatility. W...

  • 4 Beds
  • 3 Baths
  • MDCM2007720 MLS
4928 Edmondson Creek Rd, Preston image
4928 Edmondson Creek Rd, Preston $349,000

Tucked away between Preston and Easton, this charming one-level ranch home offers comfortable living, inviting outdoor spaces and a peaceful setting on 1+/- acre. The spa...

  • 3 Beds
  • 2 Baths
  • MDCM2007754 MLS
315 Main St, Greensboro image
315 Main St, Greensboro $249,900

Charming Greensboro bungalow ready to welcome you home! This 3-bedroom, 1-bathroom property offers a warm blend of character and modern updates throughout. The dining are...

  • 3 Beds
  • 1 Baths
  • MDCM2007760 MLS
7884 Laurel Ln, Denton image
7884 Laurel Ln, Denton $569,900

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...

  • 3 Beds
  • 3 Baths
  • MDCM2007758 MLS
Houston Branch Rd, Federalsburg image
Houston Branch Rd, Federalsburg $2,500

ONLINE REAL ESTATE AUCTION TO THE HIGHEST BIDDER OVER $2,500!! Online Bidding Opens - Tuesday, September 15, 2026. Bidding Closes - Thursday, September 17, 2026 at 12:00 ...

  • MDCM2007756 MLS
641 Lomax St, Easton image
641 Lomax St, Easton $369,900

Charming and beautifully maintained 3-bedroom, 2-full bathroom home offering classic character, thoughtful updates, and exceptional outdoor living. Original hardwood floo...

  • 3 Beds
  • 2 Baths
  • MDTA2014826 MLS

Search Eastern Shore Md Real Estate

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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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