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$580,000
5 Beds ⋅ 4 Baths
This is a beautifully updated and well-maintained Four Square located in Cambridge's Historic District. It is a grand house for entertaining both inside and out. In addition to the 5 bedrooms and 3.5 baths in the Manor House, the property boasts 2 additional buildings on the .57 acre lot filled with specimen flowers, shrubs and trees. 1 building, originally built as a Montessori school, is well suited as a studio, in-law suite, professional office space or Man cave. It is currently registered and generating income as an Airbnb.

309 Glenburn Ave, Cambridge

Listing courtesy of Compass. Contact: (410) 429-7425
$399,000
3 Beds ⋅ 4 Baths
Experience elevated coastal living in this exceptional three-level townhome in the sought-after Deep Harbor community on Cambridge Creek. Unlike anything else in the neighborhood, this residence showcases over $100,000 in post-purchase custom upgrades and curated designer finishes; crafted for the buyer who expects the very best. From the moment you step inside, the attention to detail is unmistakable. Custom wainscoting, 6" crown molding, luxury wallpaper, and bespoke drapery and window treatments create a refined, cohesive aesthetic that carries throughout the home. The entry level offers a comfortable family room, powder room, and access to a beautifully designed paver patio, perfect for relaxing or entertaining. The main living level is both stylish and functional, centered around a stunning gourmet kitchen featuring stainless steel appliances, quartz countertops, ceramic tile backsplash, and an oversized island ideal for gathering. The showstopping Ortal Wilderness gas fireplace, framed by soapstone and shiplap, adds a level of sophistication and warmth rarely found, which is truly a signature feature that sets this home apart. A dining area and private balcony provides seamless options for indoor or outdoor dining. Upstairs, the primary suite is a serene retreat, complete with tray ceiling, private balcony, and a spa-inspired bath featuring tempered tile, a frameless walk-in shower, and thoughtful luxury finishes. The walk-in closet is outfitted with a custom California Closet system for optimal organization. The second bedroom is equally impressive with custom California Closets and a built-in window seat that would be ideal as a beautifully appointed home office or guest space. The third bedroom continues the theme of quality and comfort. Outdoor living has been thoughtfully enhanced across three separate spaces, with added privacy elements including strategic landscaping, separation from neighboring homes, outdoor lighting, irrigation, and improved drainage...creating peaceful, usable environments at every level. Even the garage has been elevated with a custom cabinetry system and overhead storage solutions. Located within walking distance to downtown Cambridge, you’ll enjoy easy access to local restaurants, shops, and the brewery, all while residing in a waterfront community offering amenities such as a pool, walking paths, and direct water access on Cambridge Creek. Perfectly positioned for convenience, this home is approximately 2 hours from Washington, D.C. and just 1.5 hours from Baltimore, making it an ideal primary residence or weekend retreat. Opportunities like this are rare. Schedule your private showing today and discover what it means to own one of Deep Harbor’s most distinctive and refined homes.

416 S Seaway Ct Unit #142, Cambridge

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

$293,500
3 Beds ⋅ 2 Baths
Charming and thoughtfully updated, this move-in ready 3BR/2BA water-view farmhouse is ideally situated on a quiet street in the Cambridge Historic District. A welcoming covered front porch leads into a bright entry and dining space, with classic pocket doors opening to the living room. The kitchen is well-appointed with wood cabinetry, crown molding, granite countertops, and stainless steel appliances. A full bath with a walk-in shower and timeless black-and-white tile completes the main level. Upstairs, you’ll find two generously sized bedrooms and a spacious primary suite. The outdoor space offers a private, garden-style setting with a patio, tiered beds, a shed with electric, and an enclosed porch. Recent upgrades, including HVAC and a tankless hot water heater, provide added comfort and efficiency.

105 West End Ave, Cambridge

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$309,900
3 Beds ⋅ 3 Baths
**Price Improvement MOTIVATED SELLERS** Lovely End Unit in Deep Harbor Enjoy connection to the outdoors with two composite decks overlooking Cambridge Creek & Generation III Marina—perfect for morning coffee, sunset watching, or entertaining. This like-new, 3-level townhome delivers incredible value and convenience, a water view, and a long list of upgraded finishes throughout — including enhanced flooring, additional recessed lighting, high-end fixtures, composite decking, and upgraded kitchen + bath selections that elevate both style and function. Thoughtfully designed -the entry level features a welcoming foyer and versatile den—ideal as a home office, lounge, fitness space, or playroom—plus interior access to the attached garage. The main living level showcases an exceptional kitchen with abundant cabinetry, beautiful backsplash, recessed lighting, stainless steel appliances, large center island, and plenty of prep + storage space. The top floor features a lovely primary suite with tray ceiling detail, walk-in closet, private deck, dual vanities, and an oversized walk-in shower. Two additional bedrooms share a beautifully appointed hall bath. A great perk is the full-size stack washer & dryer which are conveniently located on the bedroom level. Deep Harbor amenities include: gated entrance, waterside walking paths, community pool, and marina access—and are all within walking distance to downtown Cambridge dining, shops, events, and waterfront recreation. **The unit is located in an area of Deep Harbor where short term rental like Air BNB, VRBO, etc. are permitted- making this a great investment opportunity as well! ** Boat slips are available on a first come first serve basis within the Deep Harbor Community OR utilize slip leases at: City of Cambridge's Municipal Yacht Basin, Dorchester Co., Generation III Marina, and Cambridge Yacht Club. Don’t miss this exceptional opportunity to secure a modern, low-maintenance home on the Eastern Shore!

519 Seaway Ln Unit #157, Cambridge

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

$425,000
3 Beds ⋅ 2 Baths
Welcome to 102 Choptank Avenue! Seller is generously offering $5,000.00 in a seller contribution toward closing costs. This quintessential 1918 house has been completely updated and currently showcases the best of the past and the present. Located just steps from the beautiful Choptank River, this house has multiple decks and a charming wrap-around porch affording glorious views of the Choptank! There are water views from virtually every room in the house. The house has been masterfully upgraded from top to bottom. The roof, heating systems, baths and kitchen have all been upgraded. The siding is new, the hot water on demand is new, the windows are new! The floors are beautiful and the porches and decks are lovely! The third floor has been completely insulated and serves as a storage area now but could definitely be finished off to provide more living space if so desired. Please come take a look! Sited within the charming historic district and just a block from the water, this lovely house is located just a few blocks from the iconic yacht club, the lighthouse and the vibrant downtown, which offers fun bars, restaurants and shops. Cambridge is alive and flourishing! Please call me for details!

102 Choptank Ave, Cambridge

Listing courtesy of Compass. Contact: (410) 429-7425
$249,000
2 Beds ⋅ 1 Baths
Welcome to 408 Bayly Avenue! This is an absolutely charming cottage sited on a magnificent lot. The living spaces are generously sized, lovely and full of great natural light. The 2 bedrooms are separated by a hall bath. Beautiful hardwood floors have been run throughout the entire house. The Dining Room is located just off the kitchen and features a large window that captures the backyard vistas. The kitchen is large, well laid out and enhanced with sparkling appliances. The laundry is conveniently located off the kitchen with direct access to the incredible back yard. There is a wonderful front porch for watching the world pass by if one is so inclined. There is also an awesome covered porch in the back, overlooking a beautiful tranquil park-like setting. There is a plethora of places throughout the house and the yard that offer great choices for entertaining, seclusion, reading or working. Parking for 2-3 cars is easily accommodated in the driveway to the left of the house. Bayly Avenue is a well-loved quiet family street located just blocks from the bustling downtown and the magnificent harbour.

408 Bayly Ave, Cambridge

Listing courtesy of Compass. Contact: (410) 429-7425
$305,000
3 Beds ⋅ 4 Baths
Nestled in the charming historic waterfront town of Cambridge, this meticulously cared-for, almost-new townhome offers a wonderful blend of comfort and style. Step inside to discover a versatile, finished recreation room on the first floor – envision a productive home office, a fun game room, or an extra space for entertaining guests. On the second level you will be greeted by a bright and airy living space. The kitchen boasts a convenient center island and elegant granite countertops. Seamlessly connected are a cozy breakfast area and an open living room, creating an ideal flow for everyday living and gatherings. Upstairs, you'll find three generously sized bedrooms. The primary suite is a true retreat, complete with a private bathroom and walk-in closet. This lovely townhome in Cambridge presents a fantastic opportunity for low-maintenance living in a vibrant, private, gated, waterfront community on the Choptank River featuring a pool, club house and marina. Don't miss your chance to make it yours! ****This home is in an FHA Approved Section of the Community! *** *****

340 Shipyard Dr, Cambridge

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
$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
$479,999
4 Beds ⋅ 3 Baths
A rare opportunity to own a piece of history with modern comforts in one of Cambridge’s most desirable neighborhoods. Welcome to 700 Church St., a charming 4-bedroom, 2.5-bath home nestled in the heart of Cambridge’s historic district. This beautifully maintained property blends classic character with thoughtful modern updates, offering the perfect balance of charm and functionality. Step inside to discover bright, inviting spaces filled with natural light, enhanced by elegant transom windows and timeless architectural details. The spacious layout includes a recently finished third-floor bedroom—ideal for guests, a home office, or a private retreat. Enjoy outdoor living with a newly added rear deck and a convenient storage shed. The yard is a gardener’s delight, featuring a thriving vegetable garden along with established mulberry, blueberry, and fig trees, plus fragrant rosemary and lavender bushes. Located just moments from downtown Cambridge and the lighthouse, this home offers easy access to local shops, dining, waterfront views, and community events—all within walking distance.

700 Church St, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$448,500
4 Beds ⋅ 4 Baths
Back on the market! Due to no fault of the Seller's, you have another chance to make this your home! Welcome to resort-style living at the prestigious Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina in Cambridge, Maryland. This beautifully maintained townhome offers the perfect blend of comfort, convenience, and Eastern Shore charm, located within one of the region’s most sought-after waterfront resort communities along the Choptank River. This 4 Bedroom 3.5 Bathroom home features tasteful upgrades throughout, including maple cabinetry in the kitchen and bathrooms, granite countertops, crown molding, and quality finishes that add warmth and sophistication to the living spaces. Enjoy a balcony on the front of the home offering views of the Choptank River-perfect for morning coffee or evening sunsets. The rear of the home offers three outdoor living spaces, ideal for entertaining, relaxing, or enjoying the peaceful resort surroundings Enjoy a relaxed coastal lifestyle just moments from the award-winning River Marsh Golf Club, marina, spa, waterfront pools, and dining. Whether you’re searching for a primary residence or weekend retreat this property places you in the heart of resort living. Golf, pool, and certain resort amenities may require membership or additional fees.

2830 Persimmon Pl Unit #A5, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$305,000
3 Beds ⋅ 4 Baths
Don’t miss this opportunity to own a beautifully maintained, nearly BUILT IN 2024 townhome in the charming waterfront town of Cambridge. Located in a private gated community along the scenic Choptank River, this home offers the perfect blend of modern comfort, style, and low-maintenance living. The entry level features a versatile finished recreation room. The main living level showcases a bright, open floor plan with a spacious living area and a stylish kitchen complete with granite countertops, a large center island, and a cozy breakfast area designed for both everyday living and entertaining. Upstairs, you’ll find three generously sized bedrooms, including a relaxing primary suite with a private bath and walk-in closet. Residents enjoy exceptional community amenities including a pool, clubhouse, and marina, all just moments from the waterfront. A fantastic opportunity to own in one of Cambridge’s most desirable waterfront communities schedule your showing today

343 Shipyard Dr, Cambridge

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

$90,000
4 Beds ⋅ 2 Baths
Come check out this spacious and versatile 4 bedroom, 1. 1/2- bath home ready for its new owner! This well-maintained property features: One bedroom and full bath on the main level, nice size livingroom , dinningroom, three additional bedrooms upstairs with a half bathroom. Bright enclosed front porch currently being used as a home office, additional storage /walk in closet space upstairs. detached shed for extra storage and a brand -new roof for a piece of mind. Plenty of space, functionality, and recent upgrades make this home a must see!

604 Pine St, Cambridge

Listing courtesy of New Realty, LLC. Contact: 4433246001
$320,440
3 Beds ⋅ 3 Baths
Quick Move-In opportunity! This new three-story townhome features a versatile recreation room, a large rear deck and scenic golf course views. The first level includes the recreation room and an attached two-car garage for added convenience. On the second floor, a modern open-concept layout seamlessly connects the Great Room, dining area and kitchen, along with a flex space ideal for working from home. All three bedrooms are privately situated on the top floor, including the owner’s suite with a well-appointed private bath, offering a peaceful retreat.

2178 Winterberry Ln, Cambridge

Listing courtesy of Builder Solutions Realty. Contact:

$699,900
7 Beds ⋅ 3 Baths
THE ORIGINAL HOME OF "CAPTAIN JOHNNIE" BUILT IN 1920 AND TOTALLY RESTORED. EXPANSIVE WATER-VIEWS WITH 300 FEET OF RIP RAP/BULK HEADING. PERFECT FOR YEAR ROUND LIVING, WEEKLY VACATION RENTAL OR VACATION HOME . BEAUTIFUL HARDWOOD FLOORS, FULLY EQUIPPED EAT IN KITCHEN, HUGE FAMILY/GREAT ROOM WITH WALL MOUNTED TV . HOME IS FULLY FURNISHED AND EXCEPTIONALLY EQUIPPED - EVERYTHING EXCEPT POOL/CARD TALBE CONVEYS. DIRECT TV AND HUGHES INTERNET. NIT-RED SEPTIC SYSTEM, HAS BEEN A SUCCESSFUL VACATION RENTAL - CAN PROVIDE DOCUMENTATION. LARGE OUTBUILDING HOUSING BIKES,CANOES AND KAYAKS THAT ALL CONVEY FABULOUS ON LINE ARTICLE AND PICTURES OF HOOPERS ISLAND AND LOCATION "ONLYINYOURSTATE - MARYLAND - MOST SCENIC DRIVE MD

1632 Steamboat Wharf Rd S, Fishing Creek

Listing courtesy of Douglas Realty LLC. Contact: (866) 987-3937
$1,495,000
3 Beds ⋅ 2 Baths
Rare opportunity in Dorchester County to purchase 108 +/- acres on Pig Neck Road just outside of Cambridge. Estimated 93 +/- acres tillable with 11.9 acres +/- acres woodland. Gorgeous old home in need or major repair or tear down. Value is in the land only. Numerous outbuildings, 20 x20 garage is newer and in good shape. Please enter home at your own risk and call local health department and planning and zoning for potential uses of property. There is a cemetery on the property near the home that can't be disturbed.

2238 Pig Neck Rd, Cambridge

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$389,900
4 Beds ⋅ 2 Baths
NEW PRICE: $389,900! Exceptional square footage value in the Historic District. This spacious 4-bedroom, 2-bathroom home is much larger than it looks, offering loads of living space and beautiful historic charm—highlighted by gorgeous hardwood floors and a stunning stained-glass window. Enjoy the modern conveniences alongside classic grace. Outdoors, you'll find a fully fenced yard plus a major historic district rarity: a concrete driveway for ample off-street parking and a detached garage! Don't miss this incredible opportunity.

306 Belvedere Ave, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$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 two rental units 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: 3028467839