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$1,250,000
4 Beds 3 Baths
Cedar Point Farm is a rare, intact nineteenth-century Chesapeake farmstead set along the Big Annemessex River between Manokin and Upper Fairmount. Approached by a long, tree-lined lane from Fairmount Road, the property encompasses upland fields, mature woodland, tidal marsh, ponds, and more than 2,200 feet of protected river frontage. The landscape is one of the most historically significant and ecologically rich tracts remaining in lower Somerset County. Originally constructed in the third quarter of the nineteenth century, the farmhouse reflects the architectural transition of rural Somerset during this period. Tradition and documentary evidence associate its principal construction phase with the 1881 marriage of Mary “Mollie” E. Ballard and Charles A. Curtis, descendants of the long-established Waters and Ballard families of Tudor Hall. The two-story side-hall/parlor plan features original arched doorway trim, turned newel post, walnut stair rail, rear service wing, and a two-story porch with lattice balusterwork. Subsequent early-twentieth-century improvements added a west wing and shed dormers while retaining the overall historic character. Accompanying the residence are several nineteenth- and early-twentieth-century outbuildings, including a board-and-batten barn, beaded weatherboard smokehouse, pump houses, sheds, and remnants of an earlier detached kitchen chimney. These structures reinforce the authenticity and continuity of the farm as a working Chesapeake landscape. Cedar Point Farm consists of two contiguous parcels—Tax Map 39, Parcels 363 and 193—held together as a single historic property. Both parcels are protected in perpetuity under a 2016 Conservation Easement granted to the Maryland Environmental Trust (MET) and the Lower Shore Land Trust (LSLT). The easement was established to preserve the property's agricultural productivity, forest resources, wetlands, wildlife habitat, and scenic Chesapeake shoreline. The easement safeguards approximately: 111 acres of mature forest, 36 acres of tidal and forested wetlands, 2 acres of ponds, 2,280 linear feet of Big Annemessex River frontage, and Habitat for Forest Interior Dwelling Birds and State-significant species. The land lies within a Targeted Ecological Area designated by Maryland DNR and sits adjacent to the Fairmount Wildlife Management Area and Chesapeake Forest Lands, forming part of a more than 5,000-acre protected block of conserved Chesapeake habitat. A mandatory 100-foot natural buffer along the river restricts disturbance and maintains the property’s scenic and ecological integrity. Property is subject to a no hunting covenant held by the current owner. GIS acres and deeded acres do not align. Buyer to perform their own due diligence. Additional information and documents available through listing agent.

27947 Fairmount Rd, Westover

Listing courtesy of The Land Group. Contact: (410) 934-3478

$199,000
3 Beds 3 Baths
RENOVATED VICTORIAN IN THE CRAB CAPITAL OF THE UNITED STATES! Welcome to the waterfront town of Crisfield, home of the annual Hard Crab Derby, the Soft Crab Celebration and the J. Millard Tawes Crab and Clam Bake. This small town hosts these large events as well as the Wheels on the Waterfront Classic Car Show and the Bluegrass Festival. Crisfield is home to the Somers Cove Marina, whose natural harbor hosts yachts, sailboats and ferry boats. Other waterfront harbors host recreation boats as well as working seafood boats. Located on high ground is this 3 Bedroom, 3 Full Bathroom Victorian that is nestled on a .521 acre fully fenced in lot. The updates include a full house HVAC system comprising of Ductless Min-Splits, thermal pane tilt-in Windows, the addition of two New Bathrooms, new Stainless Steel Kitchen Appliances, new Hot Water Heater, and new Washer and Dryer on the inside. On the outside there is fencing encapsulating the entire property, a new shed and a detached garage. The electrical and plumbing system have also been upgraded. The house offers Hardwood, LVP and Terra Cotta Floors, The home is located five minutes from local restaurants and specialty shops, ten minutes from Janes Island State Park that offers walking trails and waterfront sports and the Great Hope Golf Course. Crisfield was voted as One of the Safest Cities in America and it's the home of the Ward Brothers, nationally recognized wildlife artists and decoy carvers. The downtown boardwalk pavilion offers gorgeous sunsets and twilight view of Smith Island. If you are looking for a town that honors it's historic waterfront heritage but possesses modern conveniences, Crisfield checks all of your boxes. Contact the listing agent to make a showing appointment. Seller is listing this property at a reduced price and is selling it "As Is. Where Is".

232 N Somerset Ave, Crisfield

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$495,000
3 Beds 3 Baths
Seller is willing to do some owner financing to help with down payment as a second mortgage! Beautiful Waterfront Home in Annemessex Ridge!! Home is over 2500 sq ft and sits on 3 lots. Home has had many upgrades and renovation done. New roof has been put on 2025, freshly painted inside and new flooring. The kitchen has beautiful cabinets and granite counter tops. Tons of cabinet and counter space. The large living room has a gas burning fireplace. There is a nice family room with water views. The oversized porch is a great party room looking out over canal. The master suite is LARGE, with his and hers closets and master bath. There are 2 more very large bedrooms and 2 baths. The patio off the back of house leads to the dock and pier for your boats or jet skis!!

5111 Old Auger Rd, Crisfield

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

$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

$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

$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