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$465,000
4 Beds 3 Baths
Welcome to 308 Glenburn! This is a classically-designed 2,284 SF house surrounded by a multitude of glorious lush gardens on .26 of an acre! 308 is a lovely 4 bedroom, 2.5 bath home, served by central air conditioning and brand new windows throughout. 308 showcases a beautiful sunny living room with a charming wood-burning fireplace and a great screened-in porch just off the living room. Additionally, the house offers a gracious dining room with a cozy den/office located just off the dining room. The inviting updated kitchen is large and well laid out with great appliances and a sunny bonus/office room behind the kitchen, which leads to the back yard. Thee laundry room is located conveniently just off the kitchen. The second floor boasts 4 well-sized bedrooms and 2 updated bathrooms. The third floor is reached by built-in steps and has great potential for serving as additional living space if desired. Additionally, the house has a spacious attached 2-car garage with new remotely-controlled garage doors. The back yard hosts a large, useful garden shed sited amongst beautiful gardens. This beautiful classic house is located on a wide gracious street in Cambridge, just a few blocks from the banks of the mighty Choptank River and the Cambridge Yacht Club. If walkability to downtown restaurants and shops is of interest to you this is the ideal location. Please consider joining in the ongoing renaissance taking place in Cambridge, MD!

308 Glenburn Ave, Cambridge

Listing courtesy of Compass. Contact: (410) 429-7425

$2,295,000
4 Beds 4 Baths
Set on a 2.38 acre peninsula with 1,100 feet of waterfrontage, 1301 Broadview Drive is a thoughtfully crafted waterfront retreat defined by exceptional materials, timeless detail, and water views from every room. The exterior pairs stone and cedar shingles with copper lanterns and bluestone hardscaping for a classic Eastern Shore look, while inside, custom millwork, mahogany accents, brass floor registers, and a refined mix of designer fixtures and finishes create a warm and elevated feel throughout. The main level is designed for both everyday living and effortless entertaining, centered around an open gourmet kitchen with Shaw fireclay sinks, Waterworks fixtures, marble counters and backsplash, a mahogany island, and a fully integrated appliance suite. A beautifully finished butler’s pantry, breakfast area with custom bench seating, and great room with custom built ins and a gas fireplace with marble surround add both style and function. A dining room, library or office with built ins, powder room, mudroom, and laundry room complete the main level, while the covered deck provides the perfect place to take in the sunset. Upstairs, the private spaces are equally inviting, highlighted by a serene primary suite with a large walk-in closet, private deck, and a spacious marble bath with soaking tub and custom shower. Additional bedrooms offer custom closets, designer lighting, and beautifully finished baths, while a gym and rear upper deck add to the home’s comfort and flexibility. Outside, sweeping views stretch across the Chesapeake Bay, Little Choptank River, and Fishing Creek, with a waterside pool (as-Is) , pier with lift, boat ramp, and detached storage garage completing this exceptional property. Modern conveniences including Nest climate control, security cameras, fiber wiring in most rooms, and smartphone-controlled dimmers add ease to a home where craftsmanship, comfort, and waterfront living come together beautifully.

1301 Broadview Dr, Cambridge

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com

$1,250,000
5 Beds 4 Baths
🔥 Eastern Shore Waterfront Estate 🔥 Welcome to a true sportsman’s paradise tucked along the shores of the Chesapeake Bay—where space, privacy, and waterfront living come together in a BIG way. Built in 1988 and spanning nearly 5,000+/- square feet, this one checks boxes most properties can’t even reach… 🏡 5 Bedrooms | 3.5 Baths | 4,933+/- Sq Ft Step inside and you’ll find: • A massive eat-in country kitchen (with heated floors 👀) • Formal dining for hosting the big nights • TWO oversized family rooms for spreading out • Space for everyone… and then some But here’s where it gets wild 👇 🎯 Next-Level Extras: • Huge workshop + multiple garage spaces • Dedicated entertainment hall with FULL kitchen, bar & pool table • Built for hosting, holidays, and unforgettable weekends 🌅 Waterfront Lifestyle: • Private pier on Brooks Creek • TWO boat lifts + electric lift • Westerly sunset views over the Bay (the kind people chase 🌅) • Expansive deck for relaxing or entertaining • Private pond adding to the already unreal setting ⚙️ Major Upgrades: • Geothermal system (efficient + smart) • New roof (Oct 2024) • Expanded shop addition This isn’t just a home… it’s a compound. A retreat. A place people don’t want to leave once they get here. 💬 If you’ve been waiting for something special on the Eastern Shore… this is it.

5253 Ragged Point Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800

$1,350,000
4 Beds 5 Baths
A Private Waterfront Estate Where the World Falls Quiet—and Time Slows to Your Pace... There are homes that offer space. And there are homes that offer escape. At 5419 Ragged Point Road, you leave more than traffic behind—you leave noise, urgency, and compromise. Just a comfortable drive from Washington, D.C., Baltimore, and Ocean City, this contemporary waterfront estate gives you something rare: true privacy without isolation. Set on nearly 12 acres, with an extraordinary 1,500 feet of frontage along the quiet waters of Brooks Creek, this is not simply a home. It is a front-row seat to nature—uninterrupted, unhurried, and entirely your own. Inside, the house speaks in the language of craftsmanship. Four bedrooms. Two full and three half baths. Built in 2007 with a discipline you can feel in every line and finish. And unlike most properties of this caliber, it is offered fully furnished—each piece chosen to complement the home, not merely fill it. The kitchen is not designed to impress—it simply does. Precision appliances from Wolf, Sub-Zero, and Bosch. Everything exactly where it should be, whether you are preparing a quiet dinner for two or hosting a weekend that stretches late into the evening. The primary suite offers a different kind of luxury—the kind that restores you. A deep soaking tub. A separate shower. Silence when you want it. Space when you need it. But it is outside where this property earns its distinction. Step onto one of several balconies or decks, and the view does the work for you. Water in every direction. Light changes by the hour. Mornings that begin with stillness and sunrise and end with beauty that seem almost staged. A private pier extends your living space into the creek, complete with water, electric, and a 12,000 lb boat lift. For boaters, it is effortless. For fishermen, irresistible. For hunters, the presence of a duck blind and abundant wildlife turns the land itself into an asset few properties can claim. And yet, for all its features, the real value of this home is harder to measure. It is the moment you realize you have nowhere else to be. The quiet conversation lasts longer because it can. The feeling—rare, and increasingly valuable—that you have found a place that gives more than it takes. If you’ve been waiting for a property that offers not just waterfront, but a way of living that feels deliberate, private, and complete—this is it. Come see it for yourself. You’ll know very quickly whether it’s simply a beautiful home… or the one you’ve been looking for.

5419 Ragged Point Rd, Cambridge

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$384,900
4 Beds 3 Baths
Nestled in the waterfront community of Longboat Estates along Jenkins Creek and the scenic Choptank River, this beautifully maintained Lennar-built home offers the relaxed Eastern Shore lifestyle so many buyers are searching for. Imagine mornings on the covered front porch, afternoons spent boating or lounging by the community pool, and evenings gathering with family and friends on the rear deck and covered patio. Designed for both comfort and easy everyday living, the home features a spacious open-concept layout with four generously sized bedrooms and three full bathrooms. The highly sought-after first-floor primary suite, along with a second bedroom, creates the perfect setup for convenience and effortless main-level living. At the heart of the home, the large eat-in kitchen flows seamlessly into the main living spaces, making entertaining easy and natural. A formal dining room provides additional space for holidays, celebrations, and weekend dinners after a day on the water. Two large upstairs bedrooms share a bath, and abundant storage is located throughout the home. Situated on a lovely corner lot, the property offers a spacious fenced-in yard with established gardens, along with a large storage shed perfect for outdoor equipment, boating gear, gardening tools, and seasonal storage. Longboat Estates residents enjoy community amenities including a pool, boat ramp, and dock area, all just moments from the charm, restaurants, marinas, and waterfront attractions of Cambridge. Whether you are searching for a full-time residence, a peaceful retirement retreat, or simply a place to slow down and enjoy life near the water, this home offers the perfect blend of space, comfort, and Eastern Shore charm.

107 Regulator Dr N, Cambridge

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$290,000
4 Beds 3 Baths
***IMPROVED PRICE*** Sellers have added a brand new central heat and air system and are ready to move! Plenty of living space for extended family and packed with upgrades, this beautiful classic Colonial offers exceptional curb appeal and thoughtful updates throughout. The first floor features a bright, open-concept kitchen with recent stainless steel appliances, a new double sink and faucet, and seamless flow into the dining and family rooms—ideal for everyday living and entertaining. A flexible main-level space offers potential for a fifth bedroom, complemented by a conveniently located, recently renovated half bath. A private home office, generous family room, dining area, and laundry room provide all the space today’s buyers need. Upstairs, you’ll find four spacious bedrooms, including a private primary suite with an attached bath. A recently renovated second full bath features plank flooring that continues throughout the second level. Pull-down stairs lead to a floored attic, offering easy access to abundant storage. This home has been meticulously maintained with major updates including a 3-year-old roof, brand-new sump pump,Brand new heat and air system, new under-house lighting, fresh paint, rewired electrical outlets, a 2-year-old water heater, recent air conditioners, and new storm doors at both the front and back. All three baths have new toilets and vanities and fixtures. The kitchen has a new stainless double sink. Step outside to enjoy an entertainer’s dream backyard featuring an 8x10 gazebo, a 16x18 fire pit area, ample parking for guests (6 to 8 cars), and an outdoor shed for additional storage. This charming, classic Colonial is move-in ready and waiting to welcome your family.

807 Bayly Rd, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$615,000
8 Beds 3 Baths
This recently renovated home offers unique flexibility. It sits on a rare TRIPLE corner lot, and the expansive backyard spans two additional lots that may be subdivided. The first floor is beautifully finished with a new kitchen, scullery/laundry, parlor, great room, 3 bedrooms (including primary ensuite) and 2 more bathrooms. Nine rooms on the 2nd floor are ready to be finished as bedrooms, bathrooms, office/gym, etc. The 3rd floor includes additional heated space and storage. Historic charm is showcased throughout with grand front and rear staircases, built-in cabinetry, millwork, wainscoting, pocket doors, architectural radiators, and two original Rumford corner fireplaces. Major upgrades include a new two-zoned central HVAC system along with a high efficiency boiler for hot water and adjustable radiant heating, upgraded 320 Amp electric service (the whole home has been rewired), and updated plumbing. The front entrance has been brought back to the original woodwork with restored leaded glass sidelights and transom. The large front and side wrapped porch have been refreshed. Enjoy ample off-street parking from Choptank Avenue where there is also room for a "carriage house"/garage, workshop, boat storage and/or pool. Are you thinking Country Inn or Bed and Breakfast? A handicap ramp gives access to the porch and front entrance. There is an existing sprinkler system. Within blocks of historic downtown shopping and dining, water access, the Yacht Club, city marina, and waterfront parks. Also, there are nearby marinas that offer travel lifts, maintenance, and offseason storage. Nearby beaches and commuting distances: Assateague Island (61 miles), Rehoboth (65 miles), Ocean City (69 miles), Lewes with ferry to Cape May, and Cape Henlopen (61 miles). Distances to other areas of interest: Blackwater National Wildlife Refuge and Harriet Tubman Museum (11 miles), Saint Michaels (26 miles), Annapolis (58 miles), Washington DC (86 miles), Newark DE (88 miles), Wilmington (98 miles), NY, NY (414 miles). Washington, Newark and Wilmington have Amtrack train stations. Airports and distances: BWI (78 miles), Dulles (117 miles), PHL (115 miles).

709 Church St, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800

$225,000
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:

$625,000
3 Beds 2 Baths
Situated as the last privately owned property on Maple Dam Road before entering Blackwater National Wildlife Refuge, this 10.54± acre offering occupies an exceptional setting surrounded by refuge lands on all sides. The property lies within thousands of acres of permanently protected public ground, providing unmatched privacy, wildlife presence, and long-term landscape preservation in the heart of Dorchester County. Improvements include a 1,718± square-foot residence powered by a PV solar array, backed by an on-demand 22kw generator delivering efficient and sustainable energy. Climate control is handled by six mini-split systems, with an additional in-box unit conveying with the sale, offering flexibility for future expansion or replacement. The home features two gas fireplaces, with one having an option to burn wood, adding both comfort and versatility. A four-person hot tub is included, creating an ideal space to unwind and watch the sunset. A 30’ x 30’ garage with 14-foot ceilings provides ample room for boats, equipment, and sporting gear. in addition to the large garage, a climate-controlled office/workshop is just steps away from the main house. The land itself is highlighted by natural marsh ponds and wetlands, enhancing habitat and contributing to the area’s outstanding waterfowl hunting and well-established Sika deer population. This property offers a unique opportunity to enjoy legitimate hunting and outdoor recreation from a private home site while being fully immersed within one of Maryland’s most iconic conservation landscapes. Whether used as a full-time residence, weekend retreat, or generational sporting property, Maple Dam Road delivers an exceptional blend of access, privacy, and outdoor heritage that is increasingly difficult to find on the Eastern Shore. A BAT System upgrade plan has been developed to bring BAT/BIP System up to standards. Contact for additional information.

3819 Maple Dam Rd, Cambridge

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

$1,995,000
7 Beds 7 Baths
Nestled on the private four-acre waterfront enclave of Three Creeks Point, this extraordinary estate offers breathtaking sunrises and sunsets over Fishing Creek with sweeping southerly views of Church Creek spanning more than 180 degrees. The primary residence features 5 bedrooms, 4.5 baths, and over 5,400 square feet of thoughtfully designed living space, complemented by an expansive maintenance-free wraparound deck providing panoramic water views from nearly every angle. Enhancing the main residence is a separate 2-bedroom, 1.5-bath guest home featuring a Primary Bedroom on the 1st floor with full bath and additional bedroom in the loft with adjoining half bath. The guest home is complete with a full kitchen, laundry, private deck, and tranquil water vistas — ideal for hosting guests or multi-generational living. Just minutes from the open Chesapeake Bay, this property boasts approximately 6 feet mean low water (MLW) along the protected waters of Fishing Creek, creating exceptional opportunities for boating, fishing, crabbing, paddleboarding, and kayaking along the quiet creeks of the Little Choptank River. The L-shaped pier is fully equipped with an electric boat lift, jet ski lift, and multiple slips, offering ease of waterfront access. Recent extensive exterior improvements and renovations have enhanced both the low-maintenance appeal of the property and maximized the stunning waterfront views. Inside, the home showcases a spacious open layout perfect for everyday living and entertaining. The Great Room is filled with natural light and opens seamlessly to the wraparound deck, creating a remarkable indoor-outdoor flow. The Brand-New 2025 Kitchen is the heart of the home, completely remodeled with high-end finishes and designed to serve both the casual homeowner and the enthusiastic entertainer alike. New hardwood flooring throughout the first floor elevates the living spaces while maintaining warmth and coastal elegance. Formal living and dining areas provide refined entertaining space anchored by a stunning stone fireplace, while the sunroom, spanning the width of the home, delivers captivating eastern, western, and southern water views that shift beautifully throughout the day. The main level includes two bedrooms and a full bath tucked into a private alcove, offering comfortable guest accommodations or flexible living options. The upper level hosts the impressive primary suite, complete with vaulted ceiling, fireplace, private waterside balcony, spa-inspired ceramic tile bath with walk-in shower, and spacious walk-in closet. Two additional bedrooms and a full bath are also located on the second floor. An oversized office with vaulted ceiling and its own balcony provides an inspiring remote workspace overlooking the water. The guest house is equally inviting, featuring a first-floor bedroom and bath, full kitchen, stacked washer and dryer, and a second-floor bedroom with loft area — perfect for extended stays. A detached four-car garage offers ample storage for vehicles, water toys, and workshop needs. With its unrivaled waterfront views, deep water access, private setting, generous living spaces, updated interior features, guest accommodations, and extensive dock amenities, this exceptional property represents the pinnacle of luxury Eastern Shore living.

5202 Heron Rd, Cambridge

Listing courtesy of Sharon Real Estate P.C.. Contact:

$264,950
3 Beds 1 Baths
*****PRICE IMPROVEMENT*****Turn-key and cute as a button, this move-in-ready home is ready for you to settle in and make it your own. Be sure to review the floorplans for both the house and oversized detached garage in the photo and document sections of the MLS. Thoughtfully updated throughout, this charming property offers the perfect blend of comfort, style, and flexibility. The spacious 24' x 24' detached two-car garage features an unfinished upper level, providing endless possibilities for future expansion, a workshop, studio, home office, or additional storage. Numerous improvements have already been completed, including a brand-new HVAC system with transferable warranty, new hot water heater, and updated plumbing. Previous renovations include a tastefully updated kitchen, replacement windows, durable cedar-impression siding, and architectural roof. A convenient laundry room addition and wide brick steps further enhance the home's functionality and appeal. The spotless basement offers added peace of mind with a professionally installed drainage system and dehumidifier. From the third bedroom, stairs lead to an unfinished upper level that could easily be finished for additional living space or utilized for storage. Outside, enjoy the pleasant backyard behind the garage—perfect for gardening, entertaining, or simply relaxing. Ideally located just minutes from Route 50, this home offers easy access to shopping, restaurants, schools, and everyday conveniences, making it an excellent choice for commuters and those seeking a convenient in-town lifestyle.

409 Bayly Ave, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000

$265,900
3 Beds 2 Baths
BACK TO ACTIVE - PREVIOUS BUYER'S HOME SALE CONTINGENCY FELL THROUGH. Looking for a great home with one-level living? This well-maintained 3-Bedroom, 2-Bathroom home is what you've been looking for! The large (29' x 6') railed front porch is the perfect place for rocking chairs & relaxing, plus it offers a limited water view of the Choptank River. But if the backyard is your preferred outdoor space, then the 28' x 15' rear deck offers ample space for entertaining or enjoying the sunshine. The attached garage features additional storage and has direct access to the rear deck area & to the kitchen for ease when bringing in groceries. Original hardwood floors exist in all rooms except the kitchen & bathrooms (Living, Dining & hallway have carpet, but hardwood is underneath). The ease of the 4 1/2' hallway will be appreciated, whether moving furniture or for accessibility use. Besides all of the design and features that support efficient & comfortable living, this home is located just one block from the beautiful Choptank River and within close distance to grocery stores, banks, gas stations, restaurants, as well as the downtown businesses. Hot Tub is AS-IS, unsure of its functionality. New Furnace-2025, Attic Windows Replaced-2023, Refrigerator - 2021, Gutter Guards - 2020, Washer & Dryer - 2017, Central A/C Replaced - 2014, Crawlspce Poly - 2007, 40-Year Roof - 2001

1005 Willowmere Ln, Cambridge

Listing courtesy of McClain-Williamson Realty, LLC. Contact:

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