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5421 Skipjack Dr N, Cambridge
$110,000
3 Beds ⋅ 2 Baths
Enjoy peaceful country living at an incredible value! Located in the Bay Country community, this charming three bedroom, two bath home is conveniently located a short distance to route 50, restaurants, entertainment and shopping centers. This home has undergone some interior renovations in the last two years, offering you a head start on personalizing the space. Buyer is subject to park approval.

5421 Skipjack Dr N, Cambridge

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

700 Cattail Cv Unit 412, Cambridge
$235,000
2 Beds ⋅ 2 Baths
Experience affordable waterfront living without compromising on lifestyle in this beautifully updated top-floor penthouse. From your private balcony, enjoy peaceful long-water views stretching toward the Choptank River and front-row seats to the Fourth of July fireworks over the water. Offering 1,493 square feet of thoughtfully updated living space, this 2-bedroom, 2-bath residence features new luxury vinyl plank flooring throughout, upgraded lighting, elegant chair rail detailing, and a spacious open layout designed for comfortable everyday living. The modern kitchen has been refreshed with all-new stainless steel appliances, while the upgraded full-size stacked washer and dryer add everyday convenience. The generous primary suite includes a spa-inspired bathroom with dual vanities, new comfort-height toilets, a walk-in shower, and timeless white marble flooring. Located within the secure, gated Deep Harbour waterfront community, residents enjoy elevator access, front-door intercom entry, an assigned indoor garage parking space, and the added benefit of a rare private storage unit. Deep Harbour offers an exceptional waterfront lifestyle with a community marina, piers, kayak launch, scenic walking paths, swimming pool, bathhouse, picnic areas, and beautifully maintained grounds along Cambridge Creek. Just moments from historic downtown Cambridge, you'll enjoy locally owned restaurants, shops, marinas, festivals, and the exciting Cambridge Harbor redevelopment on the Choptank River, bringing new waterfront dining, entertainment, and recreational amenities. Perfectly positioned for commuters and weekend travelers alike, Cambridge offers convenient access to Annapolis, Easton, Salisbury, Ocean City, and the broader Chesapeake Bay region—making it easy to enjoy coastal living while staying connected to work and recreation. Whether you're looking for a full-time residence, weekend retreat, or low-maintenance waterfront home, this penthouse delivers exceptional value, security, and an enviable Eastern Shore lifestyle. 𝗣𝗿𝗼𝗽𝗲𝗿𝘁𝘆 𝗛𝗶𝗴𝗵𝗹𝗶𝗴𝗵𝘁𝘀 • Top-floor penthouse with long water views toward the Choptank River • 1,493 sq. ft. | 2 Bedrooms | 2 Full Baths • Private balcony with water views and Fourth of July fireworks • New luxury vinyl plank flooring throughout • All-new stainless steel kitchen appliances • Full-size stacked washer & dryer • Spacious primary suite with dual vanities, walk-in shower & marble flooring • Upgraded lighting fixtures and chair rail detailing • Upgraded comfort-height toilets installed • Assigned indoor garage parking space • Rare private storage unit • Secure gated building with front-door intercom • Two elevators serving all residential floors • Waterfront community with marina, piers & kayak launch • Swimming pool, bathhouse, picnic areas & waterfront walking paths • Minutes to historic downtown Cambridge • Near the exciting Choptank Harbor waterfront redevelopment • Easy access to Easton, Annapolis, Salisbury, Ocean City & the Chesapeake Bay • Affordable, low-maintenance waterfront living on Maryland's Eastern Shore

700 Cattail Cv Unit 412, Cambridge

Listing courtesy of Kinetic Realty, Inc.. Contact:

1213 Horse Point Rd, Fishing Creek
$199,000
3 Beds ⋅ 1 Baths
Looking for a fixer-upper with sweeping views of the Chesapeake Bay? This is your chance to own a special piece of Hoopers Island paradise. The property features a 3-bedroom home ready for renovation, along with two outbuildings offering excellent storage or workshop potential. Enjoy breathtaking sunsets over the Chesapeake Bay from the front of the property, while the rear backs to a peaceful creek—perfect for launching canoes or kayaks right from your backyard. Whether you envision a full-time residence, weekend retreat, or second home, this property offers the setting to create your ideal island getaway. Located within the highly regarded K–8 Southern Dorchester School District, this unique waterfront-adjacent opportunity combines stunning views, water access, and endless potential.

1213 Horse Point Rd, Fishing Creek

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

603 Academy St, Cambridge
$199,900
3 Beds ⋅ 3 Baths
Welcome home to 603 Academy St, a charming 3 Bed, 2.5 Bath home in downtown Cambridge, just blocks from the Choptank River. A spectacular, fully-renovated property that blends everything new with the peace of mind that comes with a top-to-bottom 2025 renovations. Key Home Features & Upgrades: Brand New Systems (2025): Enjoy maximum efficiency and safety with a new roof, new mini split heat and air conditioning systems, new electrical wiring, and new plumbing. Modern Interior: The home boasts all-new LVP flooring throughout and a beautifully renovated kitchen equipped with brand new appliances. The bathrooms have also been fully updated with modern fixtures and finishes. Spacious and Bright with a functional floor plan, ample living space, and charming details. Discover the Cambridge Lifestyle: Cambridge, MD, offers a unique blend of small-town hospitality, rich history, and stunning natural beauty. This historic seaport community is a haven for outdoor enthusiasts, with easy access to the Choptank River and Chesapeake Bay for boating, fishing, and kayaking. Enjoy the local culture in the revitalized downtown area, featuring boutique shops, art galleries, and diverse local cuisine. Year-round community events and festivals like the Taste of Cambridge and the Cambridge Classic Powerboat Regatta. Proximity to the Blackwater National Wildlife Refuge, offering extensive trails for hiking and biking amidst diverse wildlife. This move-in-ready home offers an exceptional opportunity to own a piece of this desirable and growing Eastern Shore town.

603 Academy St, Cambridge

Listing courtesy of TTR Sotheby's International Realty. Contact:

Michaels Way Unit 2E, East New Market
$210,000
2 Beds ⋅ 2 Baths
55+ Condominium Living in Historic East New Market Welcome to affordable, low-maintenance living in the heart of historic East New Market. This quiet 55-and-older condominium community offers thoughtfully designed residences perfect for those looking to downsize without sacrificing comfort or quality. Each building features five well-appointed units with spacious layouts, including large kitchen areas and beautifully tiled showers. All units include two full bathrooms, with handicap-accessible showers designed for ease, safety, and long-term comfort. Quality construction and practical design make everyday living both convenient and enjoyable. One building is fully completed with residents currently living in the community, while the second building is under construction. Three one-bedroom units are available now for immediate move-in. Residents enjoy a peaceful setting with a nearby park, ideal for easy walks and outdoor relaxation. Best of all, there is no yard maintenance, allowing you to focus on enjoying life instead of upkeep. Weekend open houses will be held regularly. This is an excellent opportunity for those seeking very affordable 55+ living in a charming small-town setting. Tax amounts are not accurate The first new two bedroom unit is ready for move in. Schedule a tour!

Michaels Way Unit 2E, East New Market

Listing courtesy of Keller Williams Realty. Contact:

Michaels Way Unit 2D, East New Market
$199,900
2 Beds ⋅ 2 Baths
55+ Condominium Living in Historic East New Market Welcome to affordable, low-maintenance living in the heart of historic East New Market. This quiet 55-and-older condominium community offers thoughtfully designed residences perfect for those looking to downsize without sacrificing comfort or quality. Each building features five well-appointed units with spacious layouts, including large kitchen areas and beautifully tiled showers. All units include two full bathrooms, with handicap-accessible showers designed for ease, safety, and long-term comfort. Quality construction and practical design make everyday living both convenient and enjoyable. One building is fully completed with residents currently living in the community, while the second building is under construction. Three one-bedroom units are available now for immediate move-in. Residents enjoy a peaceful setting with a nearby park, ideal for easy walks and outdoor relaxation. Best of all, there is no yard maintenance, allowing you to focus on enjoying life instead of upkeep. Weekend open houses will be held regularly. This is an excellent opportunity for those seeking very affordable 55+ living in a charming small-town setting. Tax amounts are not accurate. The first new two bedroom unit is ready for move in. Schedule a tour

Michaels Way Unit 2D, East New Market

Listing courtesy of Keller Williams Realty. Contact:

Michaels Way Unit 2C, East New Market
$199,900
2 Beds ⋅ 2 Baths
55+ Condominium Living in Historic East New Market Welcome to affordable, low-maintenance living in the heart of historic East New Market. This quiet 55-and-older condominium community offers thoughtfully designed residences perfect for those looking to downsize without sacrificing comfort or quality. The first of the new two bedroom units is available for move in. Schedule a tour. Each building features five well-appointed units with spacious layouts, including large kitchen areas and beautifully tiled showers. All units include two full bathrooms, with handicap-accessible showers designed for ease, safety, and long-term comfort. Quality construction and practical design make everyday living both convenient and enjoyable. One building is fully completed with residents currently living in the community, while the second building is under construction. Three one-bedroom units are available now for immediate move-in. Residents enjoy a peaceful setting with a nearby park, ideal for easy walks and outdoor relaxation. Best of all, there is no yard maintenance, allowing you to focus on enjoying life instead of upkeep. Weekend open houses will be held regularly. This is an excellent opportunity for those seeking very affordable 55+ living in a charming small-town setting.

Michaels Way Unit 2C, East New Market

Listing courtesy of Keller Williams Realty. Contact:

Michaels Way Unit 2B, East New Market
$199,900
2 Beds ⋅ 2 Baths
55+ Condominium Living in Historic East New Market Welcome to affordable, low-maintenance living in the heart of historic East New Market. This quiet 55-and-older condominium community offers thoughtfully designed residences perfect for those looking to downsize without sacrificing comfort or quality. Each building features five well-appointed units with spacious layouts, including large kitchen areas and beautifully tiled showers. All units include two full bathrooms, with handicap-accessible showers designed for ease, safety, and long-term comfort. Quality construction and practical design make everyday living both convenient and enjoyable. One building is fully completed with residents currently living in the community, while the second building is under construction. Three one-bedroom units are available now for immediate move-in. Residents enjoy a peaceful setting with a nearby park, ideal for easy walks and outdoor relaxation. Best of all, there is no yard maintenance, allowing you to focus on enjoying life instead of upkeep. Weekend open houses will be held regularly. This is an excellent opportunity for those seeking very affordable 55+ living in a charming small-town setting. The first of the new 5 two bedrooms units is ready for move in! Schedule a tour

Michaels Way Unit 2B, East New Market

Listing courtesy of Keller Williams Realty. Contact:

Michaels Way Unit BUILDING 2 A, East New Market
$210,000
2 Beds ⋅ 2 Baths
55+ Condominium Living in Historic East New Market Welcome to affordable, low-maintenance living in the heart of historic East New Market. This quiet 55-and-older condominium community offers thoughtfully designed residences perfect for those looking to downsize without sacrificing comfort or quality. Each building features five well-appointed units with spacious layouts, including large kitchen areas and beautifully tiled showers. All units include two full bathrooms, with handicap-accessible showers designed for ease, safety, and long-term comfort. Quality construction and practical design make everyday living both convenient and enjoyable. One building is fully completed with residents currently living in the community, while the second building is under construction. Three one-bedroom units are available now for immediate move-in. Residents enjoy a peaceful setting with a nearby park, ideal for easy walks and outdoor relaxation. Best of all, there is no yard maintenance, allowing you to focus on enjoying life instead of upkeep. Weekend open houses will be held regularly. This is an excellent opportunity for those seeking very affordable 55+ living in a charming small-town setting. The first of five new two bedroom is ready for move in. Schedule an appointment today!

Michaels Way Unit BUILDING 2 A, East New Market

Listing courtesy of Keller Williams Realty. Contact:

3241 Robbins Rd, Crapo
$239,000
Duck and Geese Paradise – This unique hunting property, with an existing church, could be your dream hunting lodge. This remarkable estate offers a rare opportunity to own your hunting camp in the heart of nature's bounty, bordered on the southern property line by Fishing Bay Wildlife Sanctuary. The property's key feature is its ideal location, nestled in the serene surroundings of Crapo, MD, offering a tranquil escape from the hustle and bustle of modern life. While conveniently close to modern metro centers, it's ideally situated amid some of the best hunting and fishing grounds on the East Coast. The property boasts an existing church that opens up exciting possibilities. Transform it into your hunting lodge, creating a unique and atmospheric retreat for you and your friends. For hunting enthusiasts, this property is a haven for Sika deer and waterfowl. The property is expertly set up for duck hunting and features a long boardwalk that takes you to the duck pond and duck blind in the center of the marsh. And a convenient location in the pines with a deer stand and feeder. Immerse yourself in the natural beauty and abundance of wildlife that surrounds you, creating an unparalleled hunting experience. Take advantage of this rare opportunity to own an affordable piece of paradise. Whether you're a seasoned hunter or looking to establish a nature retreat, this property offers a cost-effective way to make your dreams a reality. This is more than just a property; it's an invitation to immerse yourself in the great outdoors, create lasting memories, and build a unique haven for hunting and relaxation. You can use the opportunity to make 3241 Robbins Rd your private retreat in the heart of nature's wonders. The property consists of two lots. Church: 0.519 acres (See the attached survey plat in documents). The more considerable lot: the tax map indicates 15 acres; however, the survey documents indicate 34.5 acres. (A survey performed by the former owner but not recorded is attached in the documents, indicating 34.5 acres are connected to the documents)

3241 Robbins Rd, Crapo

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

2603 Toddville Rd, Toddville
$44,000
2 Beds ⋅ 1 Baths
This bungalow is located in the quaint, water oriented community of Toddville. It has had some repairs including a brand new architectural shingled roof. More repairs still needed-likely new well is needed. Great get away or hunting/fishing cabin, or primary residence if you are seeking peace and quiet! Elijah's store is just down the road, so no need to drive to Cambridge for supplies. Prior contract fell thru due to personal reasons of buyer.

2603 Toddville Rd, Toddville

Listing courtesy of Coldwell Banker Realty. Contact:

802 Allen St, Cambridge
$240,000
2 Beds ⋅ 2 Baths

802 Allen St, Cambridge

Listing courtesy of Marius Realtors, Inc.. Contact:

206 Maryland Ave, Cambridge
$165,000
INVESTOR ALERT! PRICE IMPROVEMENT! As well as price improvement seller is willing to provide credit toward roof replacement with an acceptable offer. Rare opportunity to own a duplex, with bottom unit currently occupied! "Downtown" zoning, no flood insurance required and steps away from the up-and-coming waterfront project "Cambridge Harbour". Location, Location Location! Walking distance from Historic downtown Cambridge; including restaurants, marinas and shops. This unique property offers water views of the Choptank River, ample parking, and the convenience of being steps away from businesses while offering that neighborhood feel. The first-floor unit offers two bedrooms, one full bath, kitchen, laundry, dining room and living room with direct access to garage. 2nd/3rd floor unit offers 3 bedrooms with a kitchenette, laundry, full bath, and living room. * Minimum 24 hours notice required for showings.*

206 Maryland Ave, Cambridge

Listing courtesy of Keller Williams Realty. Contact:

4715 Petersburg Back St, Hurlock
$56,000
1 Beds ⋅ 1 Baths
Nestled on 0.60 acres just outside the City of Hurlock, this charming country property offers a world of possibilities. Currently home to a 924 sq. ft. mobile home in need of removal, this land is the perfect blank slate for your dream home or weekend getaway. Across the street, a brand-new construction home sets the tone for new development and a peaceful neighborhood. If they can do it, so can you! According to the County and City of Hurlock it is outside the city limits and considered Dorchester County. They also said it has well and septic but you must call the Health Department to verify. Located just 15 minutes from Katie's Cafe, Johnny’s Tavern, and Suicide Bridge Restaurant, you'll enjoy the best of country serenity with convenient access to local hotspots. Plus, you're only 20 minutes to Cambridge, 50 minutes from St. Michaels, 75 minutes from Ocean City or Dover, and 90 minutes to Annapolis making weekend escapes a breeze. Fishing, boat, or water enthusiasts will love the nearby Chester River Country Club Lake, just 5 minutes away, offering a great spot to unwind. Whether you're looking to build new or embrace country life, this property offers a perfect balance of peace and accessibility

4715 Petersburg Back St, Hurlock

Listing courtesy of EXP Realty, LLC. Contact: