8

Deal Island Historic District, MD Homes for Sale

Section Image Section Image
  • 23232 Lola Wheatley Rd, Deal Island, MD 21821
    23232 Lola Wheatley Rd, Deal Island, MD 21821
    23232 Lola Wheatley Rd, Deal Island, MD 21821
    /51

    $249,900

    • 4 Beds
    • 2 Baths
    • 1,692 Sq Ft

    23232 Lola Wheatley Rd, Deal Island, MD 21821

    **Restored 1900 Traditional Farmhouse in Historic Deal Island, Maryland** Discover the charm of this beautifully restored 1900 traditional farmhouse, nestled in the picturesque setting of historic Deal Island. This stunning home perfectly balances timeless character with modern amenities, offering a unique opportunity to own a piece of history. As you enter, you'll be greeted by the warm ambiance

    Agent Photo

    Justin Yon

    Century 21 Home Team Realty

    (667) 297-6589

    23232 Lola Wheatley Rd, Deal Island, MD 21821
  • Parcels B & C Rolfe Ln, Deal Island Historic District, MD 21821
    Parcels B & C Rolfe Ln, Deal Island Historic District, MD 21821
    Parcels B & C Rolfe Ln, Deal Island Historic District, MD 21821
    /8

    $149,999

    $25K PRICE INCREASE
    • Land
    • 2.67 Acres
    • $56,179 per Acre

    Parcels B & C Rolfe Ln, Deal Island Historic District, MD 21821

    RARE WATERFRONT OPPORTUNITY ON TANGIER SOUND – 2.34 ACRES WITH PRIVATE BEACH!This is one of the last remaining waterfront lots featuring a private beach along the scenic Tangier Sound with approved septic. Spanning a generous 2.34 acres, this property offers a perfect blend of seclusion and open-water views. Imagine building your dream home nestled in the private wooded area of the lot while

    Timothy Morgan Keller Williams Realty Delmarva

    Parcels B & C Rolfe Ln, Deal Island Historic District, MD 21821
  • Parcel 96 Deal Island Rd, Deal Island Historic District, MD 21821
    Parcel 96 Deal Island Rd, Deal Island Historic District, MD 21821
    /2

    $24,999

    • Land
    • 13,068 Sq Ft
    • $83,330 per Acre

    Parcel 96 Deal Island Rd, Deal Island Historic District, MD 21821

    0.3 acre commercially zoned property located on the corner of Deal Island Rd and Hotel Rd. Lot was previously home to a gas station in the 1980s, which has since been demolished. Old perc records are available. Lot is conveniently close to the Deal Island boat ramp and within minutes you can be out on the Chesapeake Bay. Great corner location! Owner financing is available.

    Melissa Laird LAIRD & ASSOCIATES

    Parcel 96 Deal Island Rd, Deal Island Historic District, MD 21821
  • 10116 Deal Island Rd, Deal Island, MD 21821
    10116 Deal Island Rd, Deal Island, MD 21821
    10116 Deal Island Rd, Deal Island, MD 21821
    /54

    $209,000

    • 2 Beds
    • 1 Bath
    • 1,096 Sq Ft

    10116 Deal Island Rd, Deal Island, MD 21821

    Let "Home" be here! Your forever vacation in a quaint rural nautical town or make this cottage home a great 2nd home for seasonal getaways! Neighborly community with water access in every direction.This charming 2 Bedroom 1 Bathroom cottage home hosts all NEW stainless steel kitchen appliances and solid hardwood floors! Large unfinished attic space can be finished as a bonus room. All

    Caroline Reed Century 21 Harbor Realty

    10116 Deal Island Rd, Deal Island, MD 21821
  • 23290 Custom House Rd, Deal Island, MD 21821
    23290 Custom House Rd, Deal Island, MD 21821
    23290 Custom House Rd, Deal Island, MD 21821
    /64

    $299,900

    • 5 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    23290 Custom House Rd, Deal Island, MD 21821

    Looking for peace, tranquility, and true Eastern Shore living? Welcome home. This unique 5-bedroom retreat on Deal Island is still in its teenage years and ready to meet its next chapter. Lovingly cared for by the original owner since completion in 2008, this 2,400-sq-ft home blends comfort, privacy, and value rarely found in this setting. Tucked into its own private pocket of mature trees and

    William Brown EXP Realty, LLC

    23290 Custom House Rd, Deal Island, MD 21821
  • 23163 Rolfe Ln, Deal Island, MD 21821
    23163 Rolfe Ln, Deal Island, MD 21821
    23163 Rolfe Ln, Deal Island, MD 21821
    /81

    $1

    Open Fri 12PM - 3PM
    • 4 Beds
    • 2.5 Baths

    23163 Rolfe Ln, Deal Island, MD 21821

    ***AUCTION***Price of $1 is Not the Reserve or List Price. This property is being sold at auction, do not make offers to purchase prior to the sale based on this amount. For more information and our online bidding, please visit our website KaufmanAuctionsWV*** Waterfront Home on 1.87+/- Acre with Deep Water Dock on Tangier Sound - Deal Island, MD. Location: 23163 Rolfe Lane Deal Island, MD 21821.

    James Yoder Kaufman Realty and Auctions

    23163 Rolfe Ln, Deal Island, MD 21821
  • 23258 Hastings Dr, Deal Island, MD 21821
    23258 Hastings Dr, Deal Island, MD 21821
    23258 Hastings Dr, Deal Island, MD 21821
    /56

    $285,500

    $13K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,130 Sq Ft

    23258 Hastings Dr, Deal Island, MD 21821

    A Corner lot with great water views at Scott's Cove! Life here is surely going to bring you the relaxation and luxury at this waterfront community! This treasure of a rancher has all the bells and whistles. Fully Furnished (flatscreens and mounts included), 2 Bedroom 2 Bath with flex space for a workout room or hobby room, etc. The house details will amaze you! New Kraftmaid kitchen cabinets with

    Caroline Reed Century 21 Harbor Realty

    23258 Hastings Dr, Deal Island, MD 21821
  • 10515 Cassandra Dr, Deal Island, MD 21821
    10515 Cassandra Dr, Deal Island, MD 21821
    10515 Cassandra Dr, Deal Island, MD 21821
    /34

    $415,000

    • 6 Beds
    • 2.5 Baths
    • 2,401 Sq Ft

    10515 Cassandra Dr, Deal Island, MD 21821

    Beautiful Waterfront Retreat on Tangier Sound Welcome to the island life! This unique waterfront home offers a rare opportunity to own a property with 180 feet of bulkhead on the navigable Tangier Sound. Imagine spending your days crabbing and fishing right from your own backyard, and your mornings with a cup of coffee watching breathtaking sunrises. The evenings are just as magical, with

    Jennifer Whittington EXP Realty, LLC

    10515 Cassandra Dr, Deal Island, MD 21821
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