Taylors Island Real Estate

Taylors Island Real Estate

Welcome to Taylors Island, a hidden gem nestled within the picturesque Dorchester County of Maryland. This quaint and charming community, surrounded by the serene waters of the Chesapeake Bay, offers a unique blend of natural beauty and rich history that captivates both residents and visitors alike.

Taylors Island is renowned for its stunning waterfront views and lush landscapes, making it an ideal destination for outdoor enthusiasts. Whether you’re kayaking through tranquil creeks, fishing in the bay, or simply enjoying a leisurely stroll along the scenic shores, the area is a paradise for those who appreciate the great outdoors. The island's natural beauty is complemented by the warm, welcoming spirit of its residents, fostering a close-knit community atmosphere that makes everyone feel at home.

History buffs will find plenty to explore as Taylors Island boasts a rich maritime heritage. Originally a thriving hub for oystering and crabbing, the island's historical roots are evident in its charming architecture and local landmarks. Visitors can immerse themselves in the stories of the past while enjoying the modern conveniences that make life here so enjoyable.

With its peaceful ambiance, friendly community, and abundant recreational opportunities, Taylors Island is not just a place to live; it’s a lifestyle. Whether you’re considering a permanent move or a weekend getaway, this enchanting island offers a unique chance to experience the best of Maryland’s Eastern Shore. Discover the allure of Taylors Island, where every day feels like a vacation!

Newest Listings in Taylors Island

3 Beds ⋅ 3 Baths

This Extremely well maintained Property has so much to offer. Starting with 2 lots 519 & 521 together for 6.18 ac. The Solar Panels provide a large percentage of Electric with most months electric bills costing not much more than $35.00. The 3 BR w oversized closet space 2 1/2 Baths , Full laundry room, storage. A walk up stairs to the attic that is fully floored and has a exhaust fan. The immaculate 3 car garage has a 4th door in the back, electric, cement floors and work benches with tons of storage. Included is the Hustler 72" Zero Turn Mower. Out building #2 48x16 cement floor, electric. Out building #3 is 32x48 with a 16x48 addition. One with a 14' overhead door and the other with a standard door both are equipped with electric and cement floors and are all in Immaculate Condition. Their is a BIP (Bermed Infiltration Pond) located on the property and the tax fee is $250.00 annually per lot. Enjoy the Fresh Seafood specialties just steps away at the Boats & Hose Restaurant. Visit the Camp Ground on Bay Shore Rd. and Crabbing & fishing steps away several feet away at the Taylors Is. Bridge. Lots of Wildlife seen here. Hurry take a look.

Taylors Island

Listing courtesy of Brenton Realty Group. Contact: 4104794663

4 Beds ⋅ 3 Baths

MAJOR PRICE REDUCTION! A rare opportunity to own a private waterfront retreat that not only offers an exceptional Eastern Shore lifestyle, but also a proven income-producing investment — with over $46,000 in rental payouts over the past two years and an active upcoming reservation calendar, the next owner can enjoy immediate revenue while still reserving time for personal use. Escape the pace of city life and discover your own secluded waterfront sanctuary on St. John's Creek, nestled among 3.5 picturesque acres. Conveniently located within an easy drive of Baltimore, Washington, D.C., and Northern Virginia, this peaceful retreat is surrounded by the natural beauty of Maryland's Eastern Shore, where bald eagles, osprey, herons, ducks, geese, sika deer, and other wildlife are part of everyday life. The charming cottage is filled with warmth and character, offering a welcoming living room with a mantle and pellet stove, a cozy kitchen and dining area, a versatile first-floor bedroom, laundry room with daybed, and a full bath. Upstairs, a spacious bedroom with a half bath and wood stove creates a peaceful, storybook-like retreat. The brick-floored screened porch overlooks St. John's Creek and the private pier, providing the perfect setting for morning coffee, evening cocktails, or simply watching boats and wildlife pass by. Designed for gathering family and friends, the thoughtfully crafted carriage house (guest house/second dwelling) significantly expands the property's versatility. It features a spacious bunk room with six bunk beds, an oversized second-floor bedroom accommodating two queen beds, plus a main level with kitchen, dining area, living room, and full bath. An attached two-car barn-style garage provides additional storage and functionality. Between the cottage and carriage house, the property comfortably sleeps up to 15 overnight guests. Offered fully furnished and completely turnkey, the property is ready to enjoy from day one. Relax around the waterside fire pit, launch kayaks and paddleboards from your private pier, or dine just minutes away at the popular Boats & Hose Restaurant. Due to the property's active vacation rental schedule, showing availability is limited — a comprehensive virtual tour will be available soon, allowing prospective buyers to experience the property while private showings are accommodated around existing guest reservations. Whether you're looking for a private waterfront getaway, a full-time residence, or an investment with established income potential, this property offers the flexibility to do it all. This is a rare opportunity to purchase a turnkey waterfront property with immediate income already in place.

4004 Robinson Neck Rd, Taylors Island

Listing courtesy of Sharon Real Estate P.C.. Contact:

Eastern Shore hunting at its best. Taylors Island Property includes hunting cabin and small deck for crabs/fishing/trapping, etc. Large waterfront Parcel with 2 off-shore deeded islands bringing the total to 101 acres. No Utilities. This property has not been perc, but there are several sites that will. Possible owner financing (Buyer verifiable- subject to credit/financing terms). Bring your camper, atvs, boat, firearms, friends, and enjoy being away from it all! This is your FT retreat at an end of the road property. Complete Privacy! Don't miss this price reduction!! This type of property is nearly impossible to find these days-

Robinson Neck Rd, Taylors Island

Listing courtesy of XRealty.NET LLC. Contact:

Welcome to this beautiful Taylors Island lot facing the breathtaking Chesapeake Bay! This private lot enjoys over 700 feet of exposure to the magnificent bay along with 300 feet on the protected Oyster Cove. This 38+ acre lot is absolutely pristine while enjoying a soothing combination of 50% specimen trees and 50% open level pasture land. If you are a nature enthusiast look no farther as this land enjoys a plethora of wildlife from sika deer to a wide range of ducks, geese, fish and butterflies. In fact, fishermen delight in the abundant schools of rockfish and perch swimming just off the coast. This lot is well situated on Taylors Island as it is just 1 mile from the marina and 2 great local restaurants, yet just 45 minutes from Oxford, Easton and St. Michaels and 1.5 hours from Annapolis and Ocean City. Privacy abounds yet excellent internet, phone, and great electric service are readily available. BWI Airport is less than 2 hours away and it is less than 3 hours to our fabulous capitol city Washington, DC! The lot has a great potential building site and an existing perc that is well documented. The site provides great water views. Entrance to the lot is to the right of 4550 Hoopers Neck Road and is marked by a sign at the beginning of the farm road. The main gravel driveway at 4550 Hoopers Neck Road leads to to an existing home with wonderful additional waterfront acreage. Lot 37 as 4550 is referred to enjoys 2000 linear feet along the Chesapeake Bay in addition to 400 feet along Oyster Cove! The buyer of the 38 acre lot will be offered the "first right of refusal" to purchase this additional parcel so that the combined acreage could exceed 61 acres.

Hoopers Neck Rd, Taylors Island

Listing courtesy of Compass. Contact: (410) 429-7425

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