5

Homes for Sale in 21866

Section Image
  • 3011 Union Church Rd, Tylerton, MD 21866
    3011 Union Church Rd, Tylerton, MD 21866
    3011 Union Church Rd, Tylerton, MD 21866
    /22

    $60,000

    • 4 Beds
    • 1 Bath
    • 1,230 Sq Ft

    3011 Union Church Rd, Tylerton, MD 21866

    Discover a rare opportunity to own a charming, four bedroom, one bath home on historic Smith Island, Maryland in the heart of the Chesapeake Bay. Nestled on a quiet street in the quaint village of Tylerton, this furnished home is a true slice of island life, brimming with close-knit community spirit. The vinyl siding , windows and roof were updated within the last 10 - 15 years. The island has

    Laura Evans Wilson Realty

    3011 Union Church Rd, Tylerton, MD 21866
  • 21125 Bay Berry Rd, Smith Island, MD 21824
    21125 Bay Berry Rd, Smith Island, MD 21824
    21125 Bay Berry Rd, Smith Island, MD 21824
    /20

    $105,000

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft

    21125 Bay Berry Rd, Smith Island, MD 21824

    Escape the bustle of the mainland and step into the serene rhythm of island life with this charming 3-bedroom, 2-bathroom home nestled in the tight-knit waterman’s island village of Tylerton Maryland. This open floor plan home offers a large kitchen with upgraded cabinetry, dining room, spacious living room, sizable laundry area, and more. Surrounded by wildlife, marshes, and the Chesapeake Bay,

    Chris Thomas Berkshire Hathaway HomeServices PenFed Realty

    21125 Bay Berry Rd, Smith Island, MD 21824
  • 21129 Bugeye Rd, Smith Island, MD 21866
    21129 Bugeye Rd, Smith Island, MD 21866
    21129 Bugeye Rd, Smith Island, MD 21866
    /11

    $29,500

    • Land
    • 0.25 Acre
    • $118,000 per Acre

    21129 Bugeye Rd, Smith Island, MD 21866

    Cleared quarter-acre lot with expansive water views in the village of Tylerton, on historic Smith Island., Maryland. The property had a house on it in the past, the imprint/footprint is clearly visible. Water and public sewer hookups are available. Buyer must do due diligence on permits. It is conveniently located near the water, dock, market, and church.

    Laura Evans Wilson Realty

    21129 Bugeye Rd, Smith Island, MD 21866
  • 21132 Tuff St, Smith Island, MD 21866
    21132 Tuff St, Smith Island, MD 21866
    21132 Tuff St, Smith Island, MD 21866
    /11

    $100,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    21132 Tuff St, Smith Island, MD 21866

    Welcome to Tylerton, Maryland, a small, quiet village located on Smith Island, Maryland. If you are looking for a peaceful lifestyle, look no further. gathering family and friends together for a vacation getaway or the perfect retirement home. Come see what the island has to offer! This 3 bedroom 1 bath home sits on a large lot. Home has had some work done but stills needs TLC. Home is sold AS

    Melissa Laird LAIRD & ASSOCIATES

    21132 Tuff St, Smith Island, MD 21866
  • 0 Tylerton Rd Unit MDSO2003212, Tylerton, MD 21866
    0 Tylerton Rd Unit MDSO2003212, Tylerton, MD 21866
    0 Tylerton Rd Unit MDSO2003212, Tylerton, MD 21866
    /18

    $45,000

    • Land
    • 1.02 Acres
    • $44,118 per Acre

    0 Tylerton Rd Unit MDSO2003212, Tylerton, MD 21866

    “This parcel has historically contained a home, shanty shack, tool shed, and a dock extending approximately 100–150 feet, but it is currently offered as a single homesite pending confirmation from the Maryland Department of the Environment. An on‐site evaluation has been requested. The property has been continuously maintained and treated as upland throughout decades of family

    Timothy Meadowcroft Long & Foster Real Estate, Inc.

    0 Tylerton Rd Unit MDSO2003212, Tylerton, MD 21866
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group