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$474,900
3 Beds ⋅ 2 Baths
Beautifully maintained 3-bedroom, 2-full bath waterfront brick ranch home situated on a canal in the charming waterfront community of Annemessex Ridge. Nestled on a large corner double lot, this property offers the perfect blend of comfort, convenience, and coastal living. Inside, you’ll find a spacious open floor plan designed for easy entertaining and everyday living. Relax year-round in the inviting 3-season room overlooking the canal, or step outside to the rear deck and patio complete with a hot tub where you can unwind while listening to the peaceful sounds of the water along your private dock. Boating enthusiasts will love the newer boat lift, making it easy to keep your boat ready for a day on the water at a moment’s notice. The property is equipped with impressive 320-amp electric service, including electric at the dock and an RV hookup along the side of the home perfect for hosting friends and family traveling with a camper. Additional highlights include a large side-entry 2-car garage, generous outdoor space, and all the advantages of waterfront living. This exceptional home is the perfect retreat for anyone looking to enjoy life on the water. THE FOLLOWING ITEMS HAVE BEEN UPDATED: 1. NEW ROOF, 2. WASHER/DRYER, 3. KITCHEN COUNTERS AND APPLIANCES, 4. MAIN BATHROOM - 2025, 5. NEW BOAT LIFT - 2024, 6. HOT TUB 2024, 7. ELECTRIC SERVICE (320 AMP), 8. 50 AMP RV CIRCUIT AND SPOT TO PARK, 9. SHED 12X24, 10. HEAT PUMP, 11. BLOWN IN INSULATION IN ATTIC, 12. POWER AT THE DOCK

4974 Annemessex Rd, Crisfield

Listing courtesy of RE/MAX Eagle Realty. Contact: 3026591320
$50,000
3 Beds ⋅ 2 Baths
Come check out this 3-bedroom, 1.5-bath home in the heart of Deal Island offering the best of coastal country living! Tucked on a quiet street and not in a flood zone, this property is ideally located near Deal Island Beach, multiple marinas, public boat ramps, and abundant hunting grounds and wildlife management areas—perfect for outdoor enthusiasts. Set on a half acre with several sheds for added storage, there’s space to make it your own. Whether you're looking for a weekend getaway or a year-round retreat, this home offers incredible potential at a price point that leaves room to customize and create your ideal coastal escape. No HOA. You own the land, no ground rent.

10821 Toddville Rd, Deal Island

Listing courtesy of Northrop Realty. Contact: (302) 539-0800
$110,000
2 Beds ⋅ 1 Baths
Tucked away in a peaceful neighborhood next to Deal Island and the shores of Tangier Sound, this ranch-style home offers comfort and opportunity. Set on a 1-acre, mostly cleared, corner lot, the property provides plenty of room for outdoor entertaining, gardening, or future expansion. Enjoy the best of both worlds—serene coastal living with the convenience of Salisbury just under 30 minutes away, giving you easy access to shopping, dining, and recreation. The surrounding community is warm and welcoming, making it an ideal setting for those seeking a quiet retreat near the water without sacrificing everyday essentials. This 2-bedroom, 1-bath home is being sold as-is and has been refreshed with new paint, offering a clean slate for your vision. With a bit of updating and remodeling, it’s a fantastic opportunity for investors or buyers ready to make it their own. Key updates include a BAT septic system installed in 2009, a new water pump in 2022, HVAC in 2024, and a Sentricon termite bait system added in April 2026—providing peace of mind as you plan your next steps.

10762 Toddville Rd, Chance

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$329,000
3 Beds ⋅ 2 Baths
This 1,568 sq. ft. home offers comfortable living with 2 bedrooms and 1 full bath, plus a private in-law suite ideal for extended family or guests. The main home features electric baseboard heat, central air conditioning, and a floored attic providing valuable additional storage space. The in-law suite includes its own private meter box, 1 bedroom and 1 full bath, a small kitchenette, and a combined dining/sitting area. The suite opens directly to a screened-in porch, creating a peaceful space to relax and enjoy the surroundings. Outside, you’ll find a detached three-car garage, an asphalt driveway, and an additional 0.9-acre cleared lot offering extra space and flexibility. Enjoy water views of Jones Creek, which flows into the Big Annemessex River, adding to the property’s Eastern Shore charm. A public boat ramp within the subdivision provides convenient water access. Call today, this property won’t last!! INSIDE PICTURES COMING SOON!

27030 Hearts Dr, Crisfield

Listing courtesy of LAIRD & ASSOCIATES. Contact: (410) 968-0478
$249,999
3 Beds ⋅ 2 Baths
REDUCED!!! AND READY FOR A NEW OWNER!!! Don't hesitate to see this well maintained 3 bedroom, 2 bath home, nestled on the cul-de-sac in the great community of Beckford Manor, located in Historic Downtown Princess Anne near the Manokin River. It's many features include vaulted ceilings, a welcoming living room with gas fireplace, open kitchen with breakfast bar, bright dining room with double glass doors, master bedroom with attached bathroom with double sinks and walk in closet, UNFINISHED SECOND FLOOR perfect for storage or finish for even more living space, front porch, screen porch, deck, great sod yard with lawn sprinklers, and attached garage! You won't be sorry you took the time to look at this one!

30416 Plantation Dr, Princess Anne

Listing courtesy of RE/MAX Advantage Realty. Contact: (302) 628-2500
$539,000
3 Beds ⋅ 4 Baths
We want all offers! Welcome to this beautifully maintained brick ranch home situated on a canal-front double lot at the end of a quiet cul-de-sac, offering privacy, space, and waterfront living at its finest. This spacious home features 3 bedrooms, 3 full baths, and 1 half bath, including a huge primary suite with a private en suite bath. The inviting living area showcases a stunning brick fireplace with a woodstove insert, creating the perfect cozy gathering space. New wood flooring that flows throughout the home, complemented by custom wood blinds and multiple ceiling fans for comfort and style. The bright and airy sun room is a true highlight, featuring six sliding glass doors with screens that open to a brand-new deck complete with built-in self-watering planters (removable) — ideal for entertaining or relaxing while enjoying serene canal views. The kitchen was updated in 2022 with new cabinetry, and the home continues to impress with thoughtful upgrades throughout, including: Brand-new roof (2023), New carriage-style garage door with new tracks and Bluetooth-enabled openers with remotes, Screened-in attached patio gazebo, Oversized dock with a private boat ramp, Continuous pest and rodent protection contract with Terminix, Dry-lock system installed under the home (guaranteed by Terminix), Furnace and AC professionally cleaned and serviced annually by Morrow’s, and New attic caps installed in 2025. The beautifully landscaped yard enhances curb appeal, and the one-and-a-half car garage offers additional storage space. Located in a peaceful neighborhood with a minimal HOA fee of just $75 per year, this property combines modern updates, waterfront amenities, and long-term maintenance care — providing peace of mind for years to come. This exceptional canal-front retreat truly has it all — space, upgrades, and location. Please note that the square footage from the sun room and master is not encluded in the total square footage of the home.

5000 Joshua Thomas Rd, Crisfield

Listing courtesy of Decatur Byrd Realty. Contact: (410) 957-2220
$205,000
3 Beds ⋅ 2 Baths
Welcome to 30090 Kristwood, a charming 3-bedroom, 2 full bathroom home nestled in the heart of the desirable Princess Anne area. Surrounded by mature landscaping and a peaceful residential setting, this property offers the perfect blend of comfort, privacy, and convenience. Inside, you’ll find light-filled living spaces designed for both everyday living and easy entertaining. The functional layout flows effortlessly, creating a warm and inviting atmosphere. The three bedrooms provide comfortable retreats, while the two full bathrooms add everyday convenience for both residents and guests. The included leased solar panels offer added energy efficiency and potential utility savings. Outdoors, the yard offers a relaxing retreat—ideal for morning coffee, evening gatherings, or simply enjoying the quiet surroundings. Located just minutes from local shopping, dining, parks, and major routes, this home delivers a serene setting without sacrificing accessibility. Whether you’re searching for a primary residence or an investment opportunity, 30090 Kristwood offers timeless appeal in a sought-after location.

30090 Kristwood Way, Princess Anne

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200
$365,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained home located on a desirable corner lot in the Beckford Manor Association. Featuring 2 bedrooms and 2 full bathrooms, this home also offers the potential for a third bedroom, providing flexibility to fit your lifestyle. Hardwood floors flow throughout the home, creating a warm and cohesive feel. The open kitchen is perfect for everyday living and entertaining, offering plenty of cabinet space and equipped with an electric cooktop, built-in oven, and microwave. Just off the living area, enjoy cozy evenings by the gas fireplace. The spacious primary suite includes a walk-in closet and a private bath. Step outside to the deck, completely rebuilt just two years ago—ideal for relaxing or hosting guests. Major updates include a heat pump and air conditioning system installed only two years ago, offering peace of mind and energy efficiency. With thoughtful updates, a functional layout, and a prime corner lot location, this home is one you won’t want to miss.

30472 Plantation Dr, Princess Anne

Listing courtesy of The Land Group. Contact: (410) 934-3478
$245,900
3 Beds ⋅ 2 Baths
Welcome to Princess Anne, Maryland and discover 11484 Somerset Avenue—a thoughtfully designed and inviting 3-bedroom, 2-bath home situated on approximately one-third of an acre. This property offers a balance of comfort, functionality, and modern style, making it ideal for both everyday living and entertaining. From the moment you arrive, you’re greeted by an impressive 40-foot front porch—perfect for relaxing mornings, evening unwinding, or hosting guests. Around back, a spacious rear deck extends your living area outdoors, creating an ideal setting for gatherings, grilling, or simply enjoying the peaceful surroundings. Inside, the home opens into a stunning great room featuring vaulted ceilings that enhance the sense of space and natural light. The open-concept layout flows seamlessly, highlighting high-quality finishes throughout, including elegant quartz and/or granite countertops that complement the kitchen and living areas. Generous closet space provides practical storage solutions, ensuring the home is as functional as it is beautiful. Every detail has been considered to deliver a blend of modern convenience and timeless charm, all within close proximity to local amenities while maintaining a quiet, residential feel. Renderings are intended for illustrative purposes only and do not reflect the exact color palette, materials, or final exterior finishes of the completed structure.

11484 Somerset Ave, Princess Anne

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$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
$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: