Refine Search
Sort by
$299,900
5 Beds 3 Baths
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 marsh, the property spans just over 2 acres—perfectly balanced with usable yard space and low-maintenance natural beauty. Spend less time on upkeep and more time enjoying small beaches, boat launches, fishing, bird-watching, and peaceful scenic walks just moments away. Inside, the first floor offers three bedrooms—including a primary suite with en-suite bath and walk-in closet—plus a full hall bath and a bonus room for flexible use. A generous laundry/utility room provides side entry and flows into an efficient kitchen with heat-resistant Corian countertops and dining space. Off the dining area, a screened-in porch overlooks the serene backyard, while the spacious living room welcomes you from the extended covered front porch poised for daytime sunshine. Upstairs offers two oversized bedrooms and a convenient half bath. Hard flooring throughout the main level, thoughtful design, and natural light elevate everyday living, all wrapped in a home under 20 years old. The potential here is exceptional—ample indoor space, a private outdoor setting, minimal-traffic street, and sweeping views where the Nanticoke, Wicomico, and Manokin Rivers meet the Chesapeake Bay and Tangier Sound. Though tucked away, you're minutes from Deal Island Harbor Beach and its westerly sunsets, and surrounded by 13,000+ acres of protected natural land within the Deal Island Wildlife Management Area—perfect for paddling, birding, and exploring. While it feels like a getaway, you're just 20 minutes from Princess Anne and under an hour to Salisbury and Pocomoke for healthcare, schools, dining, and shopping. Maryland, Delaware, and Chincoteague beaches are a little over an hour away—close enough for weekend escapes, far enough to savor quiet coastal life. Don’t miss this rare opportunity to claim your own peaceful slice of the Shore. Call today to schedule your private tour!

23290 Custom House Rd, Deal Island

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$305,000
4 Beds 3 Baths
Discover incredible space and potential at 29759 Kingston Lane in Westover, Maryland — a 4-bedroom, 3 bath home with over 2,600 square feet of living area, set on nearly two acres of peaceful countryside. Offering exceptional square footage and versatility for the price, this home is ready for its next chapter with room to update and make it your own. Inside, the spacious floor plan features a large living room, formal dining area w/ gas firepalce, and a bright eat-in kitchen with plenty of cabinet space. A first-floor bedroom provides convenience and flexibility, while upstairs you’ll find a primary ensuite, additional bedrooms, a full bath, loft area, generous closet storage, and a bonus room perfect for a home office, playroom, or hobby space. Enjoy the outdoors on the screened porch or entertain on the large rear deck overlooking a private, wooded backdrop. The property includes a two-car garage and multiple outbuildings, all with electric — including a finished building ideal for an art studio, craft area, fitness room, or home-based business, plus a large lean-to storage shed and an additional powered storage space for tools or equipment. The home also features solar panels for energy savings, a roof replaced about five years ago, tankless hot water system, and a wooded setting that enhances the sense of privacy and country charm — all just a short drive from Crisfield’s shops, restaurants, and waterfront attractions. With its generous size, flexible layout, and versatile outdoor spaces, this property offers remarkable value for the money — a wonderful opportunity to enjoy space, privacy, and potential in a tranquil Eastern Shore setting.

29769 Kingston Ln, Westover

Listing courtesy of Real Broker, LLC - Salisbury. Contact: 8554500442

$120,000
This beautiful building lot on Monie Creek is ready and waiting for your custom home. Covington Cove is an established Messick Developed neighborhood that offers waterfront living at an affordable cost. The homes are very well maintained and offer gorgeous views over calm waters laden with fish and waterfowl. Enjoy watching the eagles nesting in the branches overhead. There is no formal HOA however, residents pay an annual maintenance fee of $200 for the upkeep of the community boat ramp and common areas. This community is only 15 minutes from south Salisbury and even closer to stores and services in Princess Anne. There is a community boat ramp for your use. It's worth the trip to check this one out!

12465 Mallard Ln, Princess Anne

Listing courtesy of ERA Martin Associates. Contact: 4107491818

$315,000
4 Beds 3 Baths
Welcome to your very own slice of paradise on Smith Island, Maryland! This rare offering is a water and nature enthusiast’s delight. Currently as one of the island's most desirable rentals, this fine property is an ideal weekend/vacation retreat or full-time island home for the most discerning buyer. Existing bookings are already secured for the upcoming season! Enjoy convenient one floor living, situated on almost a full acre of land, including a 20x20 outdoor storage shed, the property boasts one of the largest yards on the entire island. This four-bedroom, two-and almost a-half-bath, cozy and inviting home has many outstanding features. The kitchen, family room, and large sun/recreation room all offer ample space for entertaining. From the new front porch accentuated with a comfortable low country bed/swing overflowing with cozy pillows, to the back deck abounding with scenic views of the marshes and a variety of waterfowl and migratory birds. Upon entering the home, you’ll be greeted with a lovely built-in, electric wall mounted fireplace encased in custom shiplap. It adds ambiance and supplementary heat to the family room. Also, a beautiful bow/picture window overlooks the front yard. The floors are newly installed luxury vinyl plank in the family room, kitchen, bathrooms and hallways. The fully updated kitchen, located just off the family room, boasts a recently installed custom, decorative glass backsplash, new butcher block countertops, and all-new black stainless GE appliances. Through the kitchen, you’ll enter a mudroom space to hang outerwear, coats and jackets. The separate laundry room, which includes a new hot water heater, washer, a new Whirlpool dryer an additional toilet. A beautiful sunroom spans the back of the kitchen featuring built in desk space, large windows and sliding doors. Currently used as a recreation/game room, this three-season room offers spectacular views of the island’s surroundings, including marshes and canals. The home has four bedrooms, with an additional storage room that could be converted into another bedroom. The primary bedroom is situated on the opposite side of the home from the three bedrooms, providing privacy. It has two large closets, an en suite bathroom with a double vanity, new toilet, and a garden tub with a separate stall shower. The three bedrooms are located on the opposite side of the home and feature a full bathroom, with tub/shower, a linen closet, extra water heater, and access to the attic space. Step outside and you’ll be greeted by a brand-new deck that spans across the back of the house. The sunrise views from this deck are absolutely breathtaking! This home has everything you need: seller offering a one-year home warranty and most of the furnishings will convey. Most homes on the island need extensive work, but this one is move in ready! If you had to describe this property with just one word, it would be STUNNING! Call today for an exclusive showing.

20949 Somers Road, Ewell

Listing courtesy of Wilson Realty. Contact: (410) 968-1882

$190,000
3 Beds 2 Baths
Welcome to a true classic in the heart of Crisfield, MD—104 years young and filled with charm! This timeless home has been thoughtfully updated to give you the best of both worlds: historic character and modern comfort. Inside, you’ll find hardwood floors throughout, a spacious living and dining room, a well-appointed kitchen, and 3 bedrooms with 2 full baths that provide plenty of space for family or guests. The enclosed front porch/sunroom is heated and cooled so you can enjoy it year-round, while the large back deck is perfect for entertaining or relaxing outdoors. A sizable shed/workshop with 80AMPS Electric Service adds extra space for storage or projects. In the last 7 years, the Seller has invested in all the big-ticket updates for peace of mind—new HVAC system, updated electric, new insulation, new paint, new appliances, a sump pump in the crawlspace, a tankless water heater, updated bathrooms, and even a water softener system, just to name a few things! Plus, enjoy the convenience of city services with no worries about well or septic. This home is full of heart, character, and thoughtful upgrades—and waiting for you to make new memories! And when you’re ready to explore, enjoy all that Crisfield, Maryland has to offer—from world-class crabbing and fishing, to fresh seafood dining, boating, and breathtaking sunsets over the Chesapeake Bay. Please note, Buyers proof of funds or financing pre-approval must be submitted to the Listing Agent prior to showing confirmation.

16 Columbia Ave, Crisfield

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$415,000
6 Beds 3 Baths
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 romantic sunsets that are perfect for a quiet glass of wine. The home's main floor features an open floor plan with a combination living room and kitchen, complete with new granite countertops. The upstairs loft is a versatile space with two large rooms, both offering incredible water views of the Tangier Sound. From here, you can watch crab and oyster boats sail by from the nearby marina. The property also includes a separate laundry room and a double-car garage with high-bay doors, perfect for storing extra-large items. A public boat ramp is less than five minutes away, so you can easily launch your boat, jet skis, kayaks, and canoes. This is your chance to enjoy your very own waterfront island property! More Details This home has three bedrooms and two full bathrooms. There are three additional guest rooms, perfect for visitors. The owner has more renovations planned and is willing to work with the buyer to choose some of the final updates. Don't let this incredible opportunity pass you by!

10515 Cassandra Dr, Deal Island

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4105463211

$199,000
3 Beds 2 Baths
Welcome to Crisfield, the Crab Capital of the United States! Located close to Crisfield High School is this INVESTOR ALERT! This charming home has a one year lease for $1,700 per month. As soon as you purchase the home you collect the rent. The home has been renovated and it offers 3 Bedrooms and 2 Bathrooms. The 20'x8' Three Season Front Porch has jalousie windows and wooden floors. The first floor offers an 18'x14' Living Room with a Gas Fireplace, a 16'x14' Dining Room, a 13'x11' Kitchen with an Electric Stove and a Stainless-Steel Refrigerator. There's a 13'x8' Sunroom and a rear 8'x9' private Rear Porch. Rounding out the first floor is a Utility Room and a Full Bathroom with a Step-In Shower. The second floor has 3 Bedrooms, all with Walk-In Closets and a Full Bathroom with a Step-In Shower. There is a lower-level 26'x20' Enclosed Room that is used for extra storage and a workbench. The home is nestled on a .45-acre lot that has a large, cleared back yard. The upgrades include Double Paned Tilt-In Windows and new Plumbing and Showers in the Bathrooms. In 2022 the entire kitchen was upgraded with new Countertops and Appliances. Crisfield is a small town with big time entertainment. Many public events that draw large crowds are the Crab Derby during the Labor Day Weekend, the Soft Shell Crab Celebration, the Bluegrass Music Festival, Wheels on the Waterfront Classic Car Show, and the J. Millard Tawes Crab and Clam Bake. Crisfield's Waterfront offers Spectacular Views and numerous Public Boat Ramps. Somers Cove Marina is home to Yachts, Sailboats and Seafood Working Boats. Come and enjoy the best that the Eastern Shore offers!

225 N N Somerset Ave, Crisfield

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$139,900
Bring your current or future business in this spacious and versatile building located in a quaint town surround by water. Freshly Painted main entry room, new doors installed. New HVAC , New Water Heater, This sale includes an additional parcel of land .50 Acre Parcel 64, Grid 0023 Deal Island Rd (Tax ID 2014004637). Bring your business dreams for great possibilities for a Community Hall, Event Center, Wellness Center, Retail Space, Office space,Daycare, Medical Center, Dr. Offices, or a place of worship! Nestled in a nautical community with plenty to do on your down time! Enjoy the outdoors! Kayaking, Boating, Jet Skiing, Fishing, Crabbing or just taking a swim. People find this town to be a great place to visit in the Spring and Summer with Multiple year round Air B and B's Located nearby. Make your dream business a reality. Buyer and Buyer's Agent must do their due diligence and verify any and all information pertaining to the property to include schools, taxes and any and all information.

10080 Deal Island Rd, Deal Island

Listing courtesy of Century 21 Harbor Realty. Contact: 4105482100

$319,900
3 Beds 2 Baths
Situated on the shores of the Chesapeake Bay at Tangier Sound, this waterfront condo is the perfect base camp for avid anglers and boating enthusiasts. Just minutes from some of the Mid-Atlantic's premier fishing grounds, trophy fish await in the deep waters and island edges surrounding Smith Island, Tangier Island, and Tunnels Island. Leave the hassle of boat ramps behind with your own 25-foot deeded boat slip, conveniently located just a short 3-minute walk from the condo. From there, you're less than an hour by boat to renowned fishing destinations known for exceptional Rockfish, Red Drum, and Speckled Trout. Adding to the appeal, enjoy significant savings compared to the cost of private marina slips in Annapolis, Kent Island, or along the New Jersey Shore. The location also offers convenient access to some of the Mid-Atlantic's most popular destinations—approximately 1.5 hours from Ocean City, 3 hours from Washington, D.C. and Virginia Beach, and just 4 hours from North Carolina's Outer Banks. After a day on the water, return home to relax and take in breathtaking bay views from your private balcony or screened porch. This direct bayfront condominium offers 1,436 square feet of comfortable living space, featuring 3 bedrooms and 2 full baths, making it an ideal waterfront retreat, vacation getaway, or year-round residence.

103 Williams St Unit #213, Crisfield

Listing courtesy of Century 21 Harbor Realty. Contact: 4105482100

$134,900
2 Beds 2 Baths
Discover the charm of this delightful manufactured home nestled in the serene community of Crisifield. With 2 spacious bedrooms and 2 full bathrooms, this 920 sq. ft. single-wide home recently updated offers a cozy retreat for those seeking comfort and convenience. Built in 1984, it combines classic design with modern living, making it a perfect choice for anyone looking to settle in a welcoming neighborhood. The expansive 2.96-acre lot provides ample outdoor space for gardening, recreation, or simply enjoying the tranquility of nature. Imagine sipping your morning coffee on the community pier while basking in the peaceful surroundings. The community atmosphere is vibrant, with friendly neighbors and a strong sense of belonging. Crisifield is not just about the home; it's about the lifestyle. Enjoy easy access to local parks, perfect for weekend picnics or leisurely strolls. The neighborhood is well-connected, ensuring that shopping and dining in the seafood capital of the world, entertainment options are just a short drive away. Public services in the area are reliable, providing peace of mind for residents. Whether you're looking for a quiet place to unwind or a community that feels like home, this property offers the best of both worlds. Embrace the opportunity to create lasting memories in a space that truly feels like your own. Don't miss out on this gem in Crisifield!

2894 Byrdtown Rd, Crisfield

Listing courtesy of Keller Williams Realty. Contact: 3023600300

$247,999
3 Beds 2 Baths
Welcome to this well-maintained 3-bedroom, 2-bath home offering comfort, convenience, and room to grow! The main level features a spacious, easy-living layout and a kitchen with granite countertops—perfect for both everyday living and entertaining. A permanent staircase leads to a large unfinished second floor, ideal for storage or future expansion. Enjoy relaxing or hosting on the screened-in porch and adjoining deck. Ideally located near University of Maryland Eastern Shore and just a short drive or bike ride to Historic Downtown Princess Anne, this home offers the best of small-town charm and convenience. With low-maintenance outdoor space and practical features throughout, it’s a wonderful option for easy living.

30471 Manor Dr, Princess Anne

Listing courtesy of The Spence Realty Group. Contact:

$149,999
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 enjoying unobstructed panoramic views of the bay and its ever-changing maritime activity. New survey completed, and the lot is ready for your vision. Watch majestic boats pass by, and end each day with breathtaking sunsets that paint the sky. Don't miss this extraordinary chance to own a piece of waterfront paradise. Call today for more details or to schedule your private tour.

Parcels B & C Rolfe Ln, Deal Island

Listing courtesy of Keller Williams Realty Delmarva. Contact: (410) 524-6400

$162,900
2 Beds 2 Baths
Welcome to 409 Myrtle Street, nestled in the heart of Crisfield…proudly known as the Seafood Capital of the World! 🌊🦀 This charming 2-bedroom, 1.5-bath bungalow captures the essence of Chesapeake Bay heritage and small-town coastal charm. Inside, you’ll find a practical and inviting layout featuring a combined living and dining area, a full bathroom, and a half bath currently serving as a laundry room which offers both comfort and versatility. Whether you’re seeking a cozy full-time residence or an ideal seasonal getaway, this home is full of potential and ready for its next chapter. Don’t miss your chance to own a slice of Crisfield’s rich history. Schedule your showing today!

409 Myrtle St, Crisfield

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$150,000
Historic Chesapeake Masonic Lodge located in Crisfield, MD. Once a booming seaport town, now its a quiet, small town with remainders of it's grand past. Beautiful building dates from 1920, all brick construction with grand architectural details. Meeting room on first floor boasts a wood coffered ceiling, small stage area and a large kitchen. Second floor meeting room has arched windows, intricate plaster detail on the wall and a painted coffered ceiling. There are several storage rooms, and two powder rooms. The roof is leaking, and there is water intrusion due to a missing cornice piece as well. There is plaster damage mainly on the front east corner of the building both upstairs and down. There is ceiling damage on the first floor due to plumbing leaks from ancient plumbing. The ancient boiler no longer works for the oil fired radiator heat. There is a lift for handicapped access to the second floor. It is indeed a diamond in the rough. There is a Maryland Historical Trust Easement on the property. Any prospective buyers should be aware of the implications. Please contact listing agent for details. All potential buyers must be prequalified, and proof provided. Listing agent must be present for showings.

3 W Main St, Crisfield

Listing courtesy of Wilson Realty. Contact: (410) 968-1882

$1,250,000
38 Room Hotel with many upgrades. This is the only hotel in Crisfield that sits on the water with beautiful Somers Cove Marina views. Rooms have water fronts views with pool was renovated 2 years ago. In 2020 the hotel extended its lobby and made a 4 bedroom apartment/home for the owners/managers over top the lobby. In the last few years all room have been Knock down and painted. 18 rooms have been updated with new floors and walk in showers. Building has had new siding put on front of building and new composite decking. In 2022 Somers Cove Hotel became a Choice Hotel as the Rodeway Inn. Since then the hotel and owners have received multiple awards, including Gold & Platinum top Hotel!!! That means they were in the top 3% of all Choice Hotels. Hotel is adjacent Somers Cove Marina. Only water-front guest lodging in Crisfield, MD. 2.47 ac site on $3000/yr 50 yr ground lease, w/ 25 yr renewal option. Features in-ground pool; 2 bldgs, harbor & marina views. Crisfield is a beautiful waterfront community, Maryland's Blue Crab Capitol, Chesapeake Bay sportsmen's' destination.

700 Norris Harbor Dr, Crisfield

Listing courtesy of LAIRD & ASSOCIATES. Contact: (410) 968-0478

$1,500,000
Calling All Investors & Builders! This 14.83-acre commercial opportunity offers endless potential with Route 13 frontage and high visibility directly behind the Veterinary Hospital on the corner. Two parcels included – 11229 (zoned C-2 Highway Commercial) + 11209 Stewart Neck Rd. (Parcel ID#2001014315, zoned Commercial) Water & sewer hook-up available Wells & septic already on each parcel Several rented buildings & a home are currently generating income Partly wooded, offering flexibility for development Whether you envision a small development, commercial venture, or future investment, this property checks the boxes. Sold “as is,” with prime location and unbeatable exposure. Don’t miss this rare chance to own nearly 15 acres of commercial land on Route. 13!

11229 Stewart Neck Rd, Princess Anne

Listing courtesy of ERA Martin Associates. Contact: 4107491818

$1,800,000
ALL SHOWINGS ARE BY APPOINTMENT ONLY---- A comprehensive data sheet on the facility is available in the documents sections of this listing. A full brochure on the property is available in the documents section of this listing by contacting the listing agent or your agent. ---- The Handy Seafood Processing facility is located in historic Crisfield Maryland on the Little Annemessex River. This waterfront facility primarily processes soft crabs, oysters, and value-added items such as crab cakes and breaded seafood items but can be adapted for a variety of different products. Opportunities range from capitalizing on the region's renowned seafood with aquaculture and seafood processing to attracting tourists through recreational offerings like boat tours and waterfront event venues. The facility waterfront is fully bulkheaded. There are two building pad areas on site that can be used for constructing additional structures. ---- R&D Test Kitchen Office and Warehouse Areas With Dock High Access Automatic LED Light System 24-7 Monitoring Security System

101 N. 7th Street, Crisfield

Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440