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$399,900
3 Beds ⋅ 2 Baths
This charming property in Ocean Pines, MD features 3 bedrooms and 2 bathrooms, offering comfortable living in a peaceful setting.

35 Tail Of The Fox Dr, Ocean Pines

Listing courtesy of Sell Your Home Services. Contact: 8882193009
$410,000
3 Beds ⋅ 2 Baths
Welcome Home to 9 Holly Court, tucked away at the end of a quiet cul-de-sac in south Ocean Pines. Upon entry, you are greeted by an open living space featuring LVP flooring, skylights, and a soaring vaulted ceiling. The upgraded kitchen offers granite countertops and stainless steel appliances and opens to a second Great Room featuring a wood-burning fireplace, additional skylights, and sliding glass doors leading outside. The first floor also includes an attached garage and spacious primary suite with a walk-in closet and private ensuite bath. Upstairs, you’ll find two additional bedrooms and a full bathroom. Outside, the oversized lot offers plenty of open space for entertaining and enjoying the coastal lifestyle. Ocean Pines offers resort-style amenities including pools, golf, tennis, pickleball, marina, parks, trails and a private oceanfront beach club, all just minutes from Ocean City and Berlin. Whether you have been searching for a second home at the beaches, primary residence, or an addition to your investment portfolio- don't delay. Please reach out anytime with questions, or to schedule a private tour.

9 Holly Ct, Berlin

Listing courtesy of Atlantic Shores Sotheby's International Realty. Contact: (410) 524-0919
$1,950,000
4 Beds ⋅ 6 Baths
Welcome to an extraordinary coastal residence in the highly sought-after South Point community of Berlin, Maryland, where approximately 5,800 square feet of luxury living is surrounded by some of the most impressive scenery on Maryland’s Eastern Shore. Perfectly positioned between two spectacular coastal landscapes, this exceptional home captures sweeping views toward Assateague Island from the rear and beautiful Newport Bay views from the front, creating incredible scenery throughout the home and a setting that is truly difficult to duplicate. Offering 4 bedrooms, 4 full bathrooms and 2 half bathrooms, this residence was designed with space, comfort and upscale coastal living in mind. High-end finishes and thoughtful craftsmanship are showcased throughout the expansive interior, complemented by abundant windows that take full advantage of the surrounding water, marsh and island views. The home's impressive layout provides generous spaces for both everyday living and entertaining. Exquisite Roman Clay range hood as well as fireplace! One of the home's most impressive features is the ability to open the first-floor living space to the outdoors through expansive bifolding doors, creating a seamless transition from the interior to the pool and surrounding coastal setting. Open the doors and transform the main level into an incredible indoor-outdoor entertaining space where the pool, bay breezes and spectacular views become an extension of the home. The massive primary suite is a destination of its own, offering exceptional proportions offering privacy and breathtaking views that make waking up here something special. Spacious additional bedrooms and beautifully appointed baths provide plenty of room for family and guests. Property also features two additional "flex" spaces that could be utilized for whatever your heart desires. Outside, enjoy your own private pool and a setting made for entertaining, relaxing and taking in the natural beauty of South Point. Combined with the bifolding doors, the outdoor living area creates an exceptional setting for hosting, relaxing by the pool and enjoying the surrounding bay and coastal scenery. The home is also fully sprinklered, adding another level of protection and convenience. For boating enthusiasts, the location is outstanding. The county-operated South Point Boat Ramp is located at the end of South Point Road and provides direct access to Sinepuxent Bay, putting boating, fishing, crabbing and exploring the coastal bays practically at your doorstep. Across Sinepuxent Bay lies the protected landscape of Assateague Island, while Newport Bay borders the western side of South Point. Despite its peaceful, private coastal setting, South Point remains conveniently located to Ocean City, Assateague Island, championship golf, restaurants, shopping, marinas and the area's renowned beaches. Assateague's Maryland entrance is approximately eight miles south of Ocean City, making this entire coastal corridor exceptionally convenient for enjoying everything the area has to offer. Located within Worcester County Public Schools, the Berlin/Ocean City area offers access to the area's established public-school system, including Berlin-area elementary/intermediate schools and Stephen Decatur Middle and High Schools, subject to current attendance zoning.

6222 S Point Rd, Berlin

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$549,900
3 Beds ⋅ 3 Baths
Welcome to one of West Ocean City's finest communities! This beautiful, single-level home sits privately back from the street on an elevated lot. Inside, you will find a bright, light-filled interior featuring vaulted ceilings, elegant built-ins, and a cozy wood-burning fireplace. A finished flex room located right off the garage provides the perfect space for a dedicated home office or an extra guest bedroom. The exterior features a highly private yard complete with gorgeous landscaping and an integrated irrigation system. Relax or entertain guests on your elevated deck that peacefully overlooks a protected forest area. Enjoy peace of mind knowing that both the roof and the HVAC system are just a few years old. This property offers exceptionally low carrying costs with zero city taxes and a professionally managed HOA at just $730 per year. To preserve the quiet neighborhood atmosphere, short-term rentals under 30 days are strictly prohibited. Looking for a pool? The adjoining Mystic Harbour neighborhood offers community pool and clubhouse memberships for only $500 per year. Best of all, you are just a short drive from Ocean City beaches, great restaurants, championship golf courses, local marinas, historic downtown Berlin, and the beautiful wild spaces of Assateague State and National Seashore. Start living your best life in West OC today.

12510 Deer Point Cir, Berlin

Listing courtesy of Seaside Resort Group, LLC. Contact:

$549,000
3 Beds ⋅ 2 Baths
Located in the sought-after community of Caine Woods in North Ocean City. This well-built 3-bedroom, 2-bathroom home offers the perfect coastal lifestyle just 3 blocks from the ocean and just one street over from the beautiful Assawoman Bay. Open floor plan- on the ground level is a nice sized foyer, super large storage area with a 2-car garage. The main level includes oversized living and dining area, nice kitchen, bedroom and a full bathroom. The second level includes 2 nice-sized bedrooms with big closets and a full bathroom. Enjoy a prime location within the community near two beautiful neighborhood parks and scenic Northside Park. This coastal style light filled home offers many features such as vaulted ceilings, skylights, and a beautiful brick wood burning fireplace. Pine ceiling accents. New roof in 2017. Generous outdoor space includes 2 large balconies. Fenced in backyard. Plenty of storage includes large closets, oversized 2 car garage and oversized storage area on the ground level. New garage door (summer 2026). From the front balcony you can enjoy some amazing sunsets. The back balcony has peaceful views of the fenced in backyard. Nice sized driveway and plenty of off-street parking. The great location allows you to walk or ride bikes to the beach, local restaurants and all types of shopping. Walking distance to the Ocean City Beach Bus stop. A wonderful opportunity to enjoy coastal living in one of Ocean City's most sought-after neighborhoods.

704 Surf Rd, Ocean City

Listing courtesy of RE/MAX Advantage Realty. Contact: (410) 723-3600
$1,385,000
3 Beds ⋅ 2 Baths
Nearly 36.5 acre Gentleman's Farm ready for your personal touch! Neighboring Parcels 149 and 202 are a blank canvas for you to create your vision.

10863 Cathell Rd, Berlin

Listing courtesy of Newport Bay Realty. Contact: 4102137040
$345,000
2 Beds ⋅ 2 Baths
Welcome to this charming and well-maintained 2-bedroom, 2-bath upper-level condo in Oyster Bay Villas, located in the desirable Caine Woods neighborhood of North Ocean City, just off 142nd Street. Only 2.5 blocks from the beach, this home is within easy walking distance to the ocean while offering a quiet residential setting. This nicely furnished second-floor unit is located in a duplex-style building and features an open living and dining area, luxury vinyl plank flooring, a full kitchen, two bedrooms, two full bathrooms, and its own in-unit laundry. The unit also includes two assigned parking spaces behind the building. Conveniently located near restaurants, shopping, entertainment, and other North Ocean City amenities. Whether you're looking for a beach getaway, second home, full-time residence, or investment property, this is a wonderful opportunity in a great coastal location. Reserve Study completed.

504 Seaweed Ln Unit #A, Ocean City

Listing courtesy of Evergreen Properties. Contact:

$799,000
5 Beds ⋅ 4 Baths
Contractor's Alert! R-2 Zoning. This strategically located home within a short walk to the Ocean and the Bay has so much potential to expand the living space! In addition to the 3 bedroom 1.5 bath home and a separate entrance second floor 1 bedroom 1.5 bath apartment with balcony and loft this property possesses a huge 20 ft by 20 ft first floor two story unfinished room off the kitchen that could be finished to a great room with cathedral ceilings,or possibly primary bedroom suite, or additional bedrooms. This room is already studded out with electricity, insulation and beautiful sliders and arched windows on two sides already in place. It just needs drywall and your imagination! The 2nd floor 1 bedroom apartment with balcony and and extra sleeping room in loft has separately metered electric service. There is a one car garage plus a separate large storage shed. The backyard is fenced for privacy with lots of outdoor seating space and room for a hot tub. Potential, potential, potential for awesome rental income or a flip after conversion of huge unfinished area. A list of newly upgraded features is attached as a document in disclosures. Must see. No condo or HOA fees. The owners do not rent but the rental income potential, especially if the massive 20 x 20 unfinished 1st floor space were finished would be high.

148 Jamestown Rd, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$669,500
4 Beds ⋅ 3 Baths
Welcome to 10785 Windmill Creek Lane, a beautiful brand-new Cumberland model and currently for sale in the new community of The Refuge at Windmill Creek. Offering approximately 1,907 sq. ft. on the main living level plus an additional 1,421 sq. ft. on the lower level, this home provides an impressive amount of space, a thoughtfully designed floor plan, and the convenience of a two-car garage. Step inside and enjoy a bright, inviting layout featuring three bedrooms conveniently located on the main level, including a spacious primary suite with a relaxing soaking tub. The beautifully appointed kitchen features quartz countertops, a gas range, and plenty of space for gathering and entertaining. One of the standout features of this home is the lower level/basement, offering approximately 1,421 sq. ft. of additional space and featuring a fourth bedroom and full bath. Whether you envision a private guest space, family room, home office, fitness area, or additional entertaining space, the lower level offers wonderful flexibility. With four bedrooms and three full baths, there is plenty of room for family and guests while still enjoying the convenience of main-level living. Step outside to the covered rear porch and enjoy the peaceful setting of a private backyard backing to trees. It’s the perfect place for morning coffee, outdoor dining, or simply relaxing at the end of the day. Even better, landscaping is taken care of, giving you more time to enjoy your home and less time worrying about yard maintenance. The Refuge at Windmill Creek also offers wonderful community amenities, including sports courts, a pickleball court, playground, and community fire pit—perfect for recreation, relaxation, and gathering with neighbors. Additional features include a two-car garage, gas heat, a tankless water heater, and all the comfort and peace of mind that come with owning a brand-new home. The location makes this home even more special. Enjoy being just minutes from River Run and GlenRiddle Golf, as well as shopping, grocery stores, restaurants, medical facilities, and more. Convenient access to Route 113 and Route 50 makes getting around the area a breeze, and the beaches of Ocean City are approximately 10 minutes away. Brand-new construction, a basement, main-level living, a two-car garage, beautiful finishes, a covered rear porch, a private tree-lined setting, community amenities, and a fantastic location near golf, shopping, dining, and the beach—10785 Windmill Creek Lane offers an exceptional opportunity to enjoy the best of the Berlin and Ocean City area. Schedule your private showing and come see everything this beautiful new home has to offer!

10785 Windmill Creek Ln, Berlin

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 520-2707
$329,900
2 Beds ⋅ 2 Baths
Pride of ownership evident as soon as you walk in the door of this lovely home. Large living room and dining area is great for entertaining family and friends. Kitchen has beautiful wood cabinets, a nice pantry and Quartz counter tops. Separate laundry room. Primary bedroom is very spacious and features an in suite bathroom wich has been upgraded with new cabinet and sink and new shower insert. 2nd bedroom has access to the hall bathroom from inside the room. Hall bath also features a new cabinet and sink. HWH is approx 5 yrs old and HVAC is approx 6yrs (serviced twice a year by Artic). Other updates include all the plumbing pipes have been replaced as well as a the picture window . Outside the home features a deck for outdoor enjoyment, a nice built in shed for all your beach and outdoor stuff, a 2 car driveway and irrigation system. Low HOA fee of $95 per month includes, grass cutting, trash pick up, outdoor pool, tennis and basketball court as well as a tot-lot. Mystic Harbour is a wonderful community close to everything in West OC. Restaurants, ice-cream parlours, groceries, shopping, beaches and the amazing Assategues Ponies! The perfect year round or beach retreat!

14 E Wind Dr, Berlin

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$329,900
2 Beds ⋅ 2 Baths
Instant equity! Recently appraised at $345,000! Location, location, location! Conveniently located right between Snow Hill & Salisbury but tucked back in the woods making you feel away from it all! Featuring 2 bedrooms and 2 full baths downstairs - with an office or potential 3rd bedroom upstairs - living room with high ceilings and natural light, eat in kitchen with cut out into the living room, and huge wrap around deck to enjoy your private lot! A concrete driveway leads to your detached 2 car garage for parking or plenty of storage! HVAC and roof have been replaced in the last 4 years among many other updates and improvements! Move right in and make this your own!

3841 Sirman Dr, Snow Hill

Listing courtesy of ERA Martin Associates. Contact: 4107491818
$419,900
4 Beds ⋅ 3 Baths
Seller is offering closing cost assistance to Buyer with an acceptable offer. Welcome to this charming Cape Cod-style home tucked away in the peaceful North Ocean Pines community, where you can enjoy a quiet neighborhood setting while still being just 10–15 minutes from the Ocean City beaches! Offering plenty of space and flexibility, this home has been recently expanded with a 4th bedroom and an additional full bathroom—perfect for guests, family, or a private home office. Fresh interior paint and new carpet upstairs make it ready for its next owners to move right in and make it their own. One feature you won't want to overlook is the huge pantry and storage space, giving you plenty of room to keep everything organized. Step outside and enjoy the front porch, or head to the backyard where a spacious patio and fenced-in yard create a great setting for cookouts, entertaining, pets, or simply relaxing among the trees. A separate storage shed provides even more room for beach gear, bikes, tools, and outdoor equipment. Need space for your toys? The property also offers room along the side of the home to park a boat or RV. Living in Ocean Pines means enjoying much more than just the home. The community offers an impressive variety of amenities, including pools, playgrounds, tennis and recreation facilities, parks, and more. Even better, Ocean Pines residents have access to the Ocean Pines Beach Club in Ocean City, including a convenient option for beach parking—making those beach days that much easier. If you're looking for more space, a peaceful setting, community amenities, and easy access to the beach, this North Ocean Pines home offers a little bit of everything!

22 Capetown Rd, Ocean Pines

Listing courtesy of RE/MAX Advantage Realty. Contact: (410) 723-3600
$674,300
4 Beds ⋅ 4 Baths
Tucked away on 1.37 private acres, this spacious 4-bedroom, 3.5-bath home offers plenty of room to spread out inside and out. The flexible floor plan features two primary suites, with one conveniently located on each level. Enjoy a bonus living room on the first floor and a spacious second-level great room with a gas fireplace and newer luxury vinyl plank flooring. The kitchen includes stainless steel appliances, a gas range, and pantry storage. A well-appointed laundry room offers abundant shelving and basket storage. Additional highlights include geothermal heating and cooling, central vacuum installed in 2025, and an oversized two-car garage with a workshop. Above the garage is an impressive 760 square feet of heated and cooled living space, offering even more flexibility. Outside, the stamped-concrete driveway welcomes you to a private retreat featuring an above-ground pool, multiple decks, a retractable awning, and plenty of outdoor space for relaxing, entertaining, and enjoying the peaceful surroundings.

5034 Spencer Rd, Snow Hill

Listing courtesy of Hileman Real Estate-Berlin. Contact: (410) 208-9200
$1,495,000
6 Beds ⋅ 6 Baths
Welcome to 10220 Shingle Landing Road, an impressive estate offering over 5,600 square feet of living space on more than 4.5 beautifully landscaped acres. Located in an exclusive setting of just five estate-sized homesites, this exceptional property offers privacy, space, and versatility—all just a few miles from the beaches of Ocean City. This expansive home features 6 bedrooms and 5.5 bathrooms, along with an attached 3-car garage and a separate 3-car detached garage. The detached garage includes a spacious second floor offering tremendous potential for a game room, home office, studio, recreation space, or other future use. The outdoor living area is truly a highlight, featuring a 40' x 20' in-ground pool with waterfall, hot tub hookup, gorgeous stone patio, and gas fire pit—creating the perfect setting for entertaining or relaxing at home. The beautifully maintained grounds feature extensive landscaping and an impressive irrigation system with more than 80 sprinkler heads across 10 zones. Inside, the kitchen features beautiful appliances, two dishwashers, trash compactor, butcher-block countertop, and Andersen French doors providing a seamless connection to the outdoor living areas. The spacious family room offers hardwood flooring and recessed lighting, while multiple additional first-floor flex rooms give the new owner the opportunity to customize the home to fit their lifestyle. A first-floor bedroom with a full bathroom provides excellent flexibility for guests or multi-generational living. Upstairs you'll find five additional bedrooms, including a spacious primary suite complete with a mini refrigerator/wet bar and separate his-and-hers closets. Additional features include two Rinnai tankless hot water systems providing an abundant supply of hot water throughout the home. With over 4.5 acres, 5,600+ square feet, six garage spaces, a resort-style pool and outdoor entertaining area, this remarkable Bishopville estate offers a rare combination of privacy and space while remaining just minutes from Ocean City beaches, restaurants, golf, marinas, and all the attractions of the resort area. A truly unique Eastern Shore property that must be seen to be fully appreciated.

10220 Shingle Landing Rd, Bishopville

Listing courtesy of RE/MAX One. Contact: 4105356291
$319,900
3 Beds ⋅ 2 Baths
Welcome to peaceful country living just minutes from downtown Snow Hill and Route 113! This well-maintained 3-bedroom, 2-bath rancher offers approximately 1,300 square feet of comfortable living space on over an acre with no HOA. Built in 1994, the home features a popular split-bedroom floor plan, an open-concept living area, and beautiful real hardwood floors.Recent improvements include fresh paint, new appliances, a brand-new hot water heater, new exterior doors and sliding glass door, updated plumbing and electrical fixtures, a water softener, and well pump. Outside, enjoy a wide covered front porch, rear deck, spacious newer shed, and a clam-shell fire pit and picnic area. With over an acre, there's plenty of room for boats, trailers, equipment, gardens, chickens, a future pole barn, outdoor entertaining, or additional improvements. The septic system has also been inspected for added peace of mind. Surrounded by a quiet, serene setting with exceptional privacy, this property offers the benefits of country living while remaining convenient to Snow Hill and Route 113. Low taxes, low-maintenance living, and low energy costs make this a great option for a first-time buyer, retiree, investor, or anyone looking for extra space and freedom without HOA restrictions.

5702 Blake Rd, Snow Hill

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$1,565,000
4 Beds ⋅ 3 Baths
Welcome to the prestigious water front home called the MERMAID house! This one owner custom built, 4 bedroom, 2.5 bath home will become your new home once you see it! Much larger then it looks! Vacation home or year round residence enjoyment awaits, this home screams rest and relaxation, inside or out! Comfortable and elegant...inside you can have a formal dining area or the current sitting area arrangement. The vaulted ceiling leading to the private area balcony is unique and adds space. Bedrooms are all of good size, 3 upstairs and with the primary bedroom and bath on the main level, you have convenience and comfort! The kitchen is spacious and bright! From the kitchen dining areas, you have a relaxing view of the water. Outside, you can relax on the deck taking in the water views or enjoy deep water access on your boat that can lead you directly to the inlet to the ocean and many points of interest and adventure! This property has an extra long dock, 6 Ft wide and can accommodate your larger vessels. Boat accessory house to store your vessels needs. Docks are a precious commodity in this area and you can have your very own. Outside shower for your water fun clean up! Sculptured driveway! All appliances convey. Furniture is negotiable, Personal property is excluded. Come and see for yourself, Mother Nature's beauty at its finest...and, just think, this can all be yours.

13463 Madison Ave, Ocean City

Listing courtesy of Ability Real Estate Service. Contact:

$498,750
4 Beds ⋅ 2 Baths
Lovingly maintained home in Downtown Berlin. Close to everything you need and all the fun stuff you want. Live comfortably on the first floor with two bedrooms (originally 3 as wall was removed between rooms to make one bedroom larger) and a shared full bath or spread out to the 2nd floor where there are 2 more bedrooms and another shared full bath. Roof replaced 2024. Screened back porch with attached deck overlooking fenced private backyard with remainder of lot beyond fence as a nice green space buffer .

330 Williams St, Berlin

Listing courtesy of Sheppard Realty Inc. Contact: 4437830299
$259,000
4 Beds ⋅ 2 Baths
Welcome to 711 Homewood Drive in Pocomoke City! This spacious 4-bedroom, 2-bath home offers plenty of room with a flexible layout and great potential to make it your own. The upgraded kitchen features stainless steel appliances, ample cabinet space, and plenty of room for everyday cooking and entertaining. The home features a large primary suite complete with a private full bathroom, along with three additional guest bedrooms and a full hall bathroom. An additional flex room provides even more versatility and could be used as a home office, playroom, hobby room, or additional bedroom depending on your needs. Outside, you'll find a detached two-car garage offering plenty of space for vehicles, storage, or projects. The garage also features a bonus second floor, providing substantial additional storage space or the potential to create a workshop or additional workspace. With generous living space, a versatile floor plan, an upgraded kitchen, and a detached garage with bonus space, 711 Homewood Drive offers plenty of possibilities for its next owner. Schedule your private showing and come see the potential this Pocomoke City home has to offer!

711 Homewood Dr, Pocomoke City

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$385,000
3 Beds ⋅ 3 Baths
A rare opportunity to own one of Pocomoke City’s grand historic homes, beautifully preserved, thoughtfully updated, and truly turnkey. This stately Dutch Colonial pairs the gracious scale and craftsmanship of another era with significant modern improvements, all in the heart of historic Pocomoke City, with the Pocomoke River just blocks from the front door. Documented as built in 1920, this home is a contributing structure within the National Register of Historic Places-listed Pocomoke City Historic District without local historic district restrictions. Three classic dormers, handsome brick steps, mature landscaping, and a beautiful corner setting introduce a home filled with architectural character. Inside, a grand center hall and exceptionally generous rooms create an immediate sense of space. Original hardwood floors, Craftsman trim, detailed millwork and dentil molding, original glass doorknobs, three sets of French doors, the beautifully detailed original staircase with its graceful volute at the base of the banister, and original cast-iron radiators preserve the home’s authentic character. The expansive living room features a wood-burning fireplace, built-in seating, abundant natural light, and room to gather on a grand scale. An adjoining window-wrapped sunroom offers wonderful flex space for an office or retreat, while the elegant dining room features an original built-in corner cabinet and period detailing. The remarkably spacious renovated kitchen features custom-crafted solid wood cabinetry with soft-close features and pull-out pantry storage, under-cabinet lighting, abundant counter space, a separate pantry, and breakfast-bar seating. An additional breakfast area provides flexible casual dining or sitting space. Just beyond, a screened porch overlooks the level, fully fenced backyard. Upstairs, a broad landing and wide hallway continue the home’s generous proportions. The primary suite offers a spacious bedroom and private bath with a walk-in shower and separate jetted soaking tub. Two additional light-filled bedrooms share a full hall bath, and upper-level laundry adds modern convenience. Stairs from the laundry area lead to a walk-up partially finished attic offering additional storage and flexible utility space. Outside are mature landscaping, a fully fenced yard, off-street driveway parking, and an Amish-built garage with automatic opener. A huge, dry full basement provides additional storage. Meticulous stewardship is evident throughout, with major improvements including a new roof in 2023 (with 47 years remaining on its warranty), dual high-efficiency heat pumps that remain under warranty, updated plumbing, upgraded electrical, replacement double-hung vinyl-clad windows throughout, and an oil boiler providing backup heat. Located along the Pocomoke River, historic Pocomoke City offers public docks and boat slips, Cypress Park, a scenic riverfront walking trail, athletic courts, theater, shops, and waterfront dining. Ocean City, Chincoteague Island, Assateague National Seashore, Berlin, and the Atlantic Coast are all within easy reach. Grand yet welcoming, historic yet wonderfully livable, this beautifully maintained Eastern Shore classic offers a rare combination of space, craftsmanship, character, and thoughtful updates.

1 2nd St, Pocomoke City

Listing courtesy of Northrop Realty. Contact: (302) 539-0800
$1,990,000
3 Beds ⋅ 3 Baths
Welcome to this spacious 3-bedroom, 2.5-bath single-family home offering 3,448 square feet of living space in a prime midtown Ocean City, ocean-block location just steps from the beach. The main living area features an open dining and living space that flows seamlessly into the modern kitchen, creating a bright and welcoming setting for everyday living and entertaining. A standout feature is the downstairs office space, currently utilized as a dental office, which offers excellent flexibility for a home office, professional workspace, additional living area or additional income! The home also features a 2-car garage, asphalt driveway which has 6 parking spaces, inviting front porch, and a spacious back deck perfect for relaxing and enjoying the ocean breeze. Ideally located near popular restaurants, bars, shopping, and area attractions, this home offers generous square footage, flexible space, and the convenience of being just steps from the beach.

4306 Coastal Hwy, Ocean City

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$419,900
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated 3-bedroom, 2-bath home in desirable Ocean Pines, Maryland—approximately 9.2 miles from Ocean City! The inviting floor plan features a convenient main-level bedroom and numerous recent improvements, including new kitchen cabinets and countertops, seven new windows, nine new doors, and 9 trees removal that created a more open and spacious setting. The crawl space has also been improved with select joist replacements and the installation of a new vapor barrier. Enjoy the many amenities Ocean Pines has to offer, including indoor and outdoor pools, the Yacht Club, parks, recreational facilities, and more—all just a short drive from Ocean City’s beaches, dining, and entertainment. Don’t miss this opportunity—schedule your private showing today!

3 Rabbit Run Ln, Ocean Pines

Listing courtesy of Douglas Realty. Contact: (866) 987-3937
$200,000
3 Beds ⋅ 2 Baths
OPEN HOUSE DATES:           SATURDAY, SEPTEMBER 5, 2026 FROM 12:00 PM - 1:00 PM          SATURDAY, SEPTEMBER 12, 2026 FROM 12:00 PM - 1:00 PM List price is Opening Bid at The Online Only Auction Sale to Be Held on The Auctioneers Website – Bidding begins Friday, September 11th @ 1:00PM & ends Wednesday, September 16th @ 1:00 PM. Welcome to 38 Fairway Lane, a charming single-level home ideally situated on a quiet cul-de-sac in the sought-after Ocean Pines community. Offering approximately 1,040± square feet of living space, this well-maintained residence features 3 bedrooms, 2 full baths, and a spacious 0.22± acre lot. Inside, the home offers an inviting and comfortable layout highlighted by hardwood flooring, crown molding, and a welcoming living area. The eat-in kitchen provides a functional space for casual dining and everyday living. Outdoor living is enhanced by multiple decks, offering plenty of space for entertaining, relaxing, or simply enjoying the peaceful surroundings. Ample storage and a practical single-level floor plan add to the home's appeal, making it well suited as a primary residence, coastal getaway, or investment property. Residents of Ocean Pines enjoy an impressive array of community amenities, including a Robert Trent Jones Sr.-designed golf course, marina, yacht club, beach club, indoor and outdoor swimming pools, tennis courts, parks, walking trails, a community center, and a variety of year-round recreational activities. Conveniently located just minutes from Ocean City beaches, dining, shopping, and entertainment.

38 Fairway Ln, Berlin

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

$1,449,900
6 Beds ⋅ 6 Baths
Rare waterfront investment opportunity! This completely turn-key property features a four-unit building with four 1-bedroom, 1-bath units, plus a separate 2-bedroom, 2-bath single-family home, all situated directly on the water in a fantastic in-town location. Enjoy the convenience of keeping your boat right outside your back door while being just minutes from many of the area’s favorite restaurants, shops, and local attractions. An exceptional opportunity for investors seeking multiple income-producing units combined with an unbeatable waterfront setting.

222 Trimper Ave, Ocean City

Listing courtesy of Coastal Life Realty Group LLC. Contact: (443) 235-8382
$430,000
3 Beds ⋅ 2 Baths
NO HOA FEES! AND This home comes with a 1-year HOME WARRANTY! Welcome to 101 Burley Street in Berlin, Maryland, America's Coolest Small Town! Featuring a warm welcome with covered front porch! Walking in you'll notice the open floorplan, with large, fully renovated, eat-in kitchen featuring warm wood cabinets, granite tops, center island, stainless appliances, stone backsplash and large table area! Just off the kitchen is a walk-in laundry room with extra refrigerator. The living room and kitchen features LVP flooring. The HUGE primary suite offers plenty of room for a king bed, sitting area or desk space! With an ensuite bath and LARGE walk-in closet. On the other side of the house you'll find 2 additional large bedrooms with nice closets and shared hall bath. The home features an oversized backyard, with FULL fencing, play area, shed and plenty of room for a DREAM garden! Located within Berlin, and just across the street from Stephen Decatur park! In Berlin you'll find a grocery store, local banks, post office, variety of quaint shops, SUNDAY farmer's market and MANY popular restaurants. Enjoy town celebrations like New Years, holiday parades, music festivals, car shows and the all-famous bathtub races! Berlin was also featured in movies like Runaway Bride and Huck Everlasting. Conveniently located Just 10-15 minutes to Ocean City and Assateague beaches! Don't Hesitate, or you'll miss this one!

101 Burley St, Berlin

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400
$299,900
4 Beds ⋅ 3 Baths
Welcome to this classically elegant Colonial home in scenic Pocomoke City, Maryland, ideally located within city limits and convenient to the river, shopping, hospitals, churches, and other local amenities. Offering 4 bedrooms, 2.5 baths, public water and sewer, a detached carport, and an additional separately deeded corner lot included in the sale, this distinctive property provides exceptional space both inside and out. From the moment you enter the foyer, you will appreciate the remarkable Amish craftsmanship and custom woodworking throughout the home. Beautiful hardwood floors, wide crown molding, chair rail, raised panels, custom cabinetry, and handcrafted details give this home warmth and timeless character. Just off the foyer is a spacious family room featuring custom-built Amish cabinetry, wood shutters at the windows, an impressive wall of display cabinets with doors, and a wet bar-perfect for entertaining. To the opposite side of the foyer is the generously sized living room with hardwood floors, custom Amish cabinetry and raised-panel detailing, a wood-burning fireplace, crown molding, and chair rail. The large formal dining room continues the home's beautiful hardwood flooring and custom woodworking, providing an inviting setting for holiday dinners and special gatherings. From the dining room, continue into the spacious kitchen, where you will find extensive custom Amish cabinetry, a built-in desk, a long center island with numerous built-in features, double ovens, and a comfortable breakfast area accented by attractive built-in display areas. The laundry/mud room offers a washer and dryer along with abundant built-in cabinetry for storage. The main level also includes a convenient half bath and an exceptionally spacious primary bedroom suite featuring a walk-in closet, private bath, and custom Amish-made full-window shutters. Upstairs are three additional bedrooms with hardwood floors and a large full bath, providing plenty of room for family, guests, home office space, or hobbies. Additional features include a roof less than five years old and a partial basement equipped with a sump pump and French drain system. Since installation of the drainage system, the basement has remained dry. Outside, enjoy a detached carport, storage shed for lawn and outdoor equipment, and the adjoining separately deeded corner lot that is included with the property, providing additional yard space and endless possibilities. This one-of-a-kind Pocomoke City home combines traditional Colonial style, outstanding craftsmanship, generous living spaces, and a convenient in-town location. A truly special property with details rarely found in today's homes.

102 Winter Quarters Dr, Pocomoke City

Listing courtesy of ERA Martin Associates. Contact: 4107491818
$139,900
6 Beds ⋅ 3 Baths
3 STORY VICTORIAN WITH ORIGINAL 3 STORY STAIRCASE AND MOLDINGS. LOTS OF ROOM FOR A LARGE FAMILY. FIRST FLOOR CONTAINS LARGE FORMAL FOYER, LIVING ROOM, DINING ROOM, FAMILY ROOM, KITCHEN, MUD ROOM, UTILITY ROOM, EAT IN KITCHEN, UNFINISHED FULL BATH AND A HALF BATH. SECOND FLOOR CONTAINS 4 BEDROOMS AND 1 FULL BATH. THIRD FLOOR CONTAINS 2 BEDROOMS. REAR STAIRCASE FROM KITCHEN TO SECOND FLOOR. SHORT WALK TO THE DOWNTOWN BUSINESS AREA AND POCOMOKE RIVER. PRIVAE BACK YEARD WITH DETACHED GARAGE. SOME DEFERRED MAINTEANCE WHICH WAS CONSIDERED IN THE MODEST LIST PRICE. A GREAT OPPORTUNITY TO INVEST SOME TIME AND MONEY AND HAVE ONE OF THE MOST IMPRESSIVE HOMES IN THE AREA. BEING SOLD IN AS-IS CONDITION. CASH OR POSSIBLE CONVENTIONAL FINANCING WITH LOCAL LENDER.

405 Market St, Pocomoke City

Listing courtesy of Hall Realty. Contact: 4104302000
$325,000
3 Beds ⋅ 3 Baths
Welcome to 1717 Cedar Street, a well-maintained contemporary home located in the established Woodland Manor community of Pocomoke City. Built in 2020, this 3-bedroom, 2.5-bath home offers 1,877 square feet of living space with a comfortable, functional layout designed for everyday living. Inside, you'll find a bright and inviting interior featuring vaulted ceilings, stainless steel appliances, generous closet space, and plenty of natural light. The home offers three spacious bedrooms and two full baths upstairs, along with a convenient half bath on the main level. Outside, enjoy a 0.24-acre lot with plenty of yard space, plus a deck and porch for relaxing, entertaining, or enjoying the outdoors. An attached two-car garage provides additional parking and storage. Best of all, there is no HOA, giving you the freedom to enjoy your property without additional association fees. With its newer construction, spacious layout, large yard, and convenient Pocomoke City location, 1717 Cedar Street is ready to welcome its next owner. Schedule your private showing today!

1717 Cedar St, Pocomoke City

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4105463211
$1,975,000
5 Beds ⋅ 4 Baths
Welcome to an exceptional waterfront retreat in the prestigious community of Bay Point Plantation, where refined coastal living, beautiful water views, and effortless access to the bay come together. This beautifully appointed 5-bedroom, 3.5-bath, three-story residence includes coveted Boat Slip #20, offering an incredible opportunity to embrace the waterfront lifestyle. From the moment you arrive, the home impresses with an oversized, finished two-car garage and a private backyard designed for relaxation and entertaining. Your own outdoor oasis features a swimming pool, spa, spacious patio, and fenced yard, creating an inviting setting for summer afternoons, evening gatherings, and weekends spent by the water. Two bay-view balconies extend the living space outdoors and provide beautiful vantage points for taking in the coastal surroundings. The ground level was thoughtfully designed to complement days spent by the pool. Enter through the garage into a generous living area ideally positioned for casual gatherings, entertaining, or relaxing after a day on the water. With convenient access to the outdoor living area, this level creates an effortless connection between indoor and outdoor spaces. A private bedroom and full bathroom complete the floor, making it an excellent retreat for family and overnight guests. The main living level is the heart of the home, showcasing an expansive great room where coastal sophistication meets everyday comfort. The spacious living area flows seamlessly into a water-view dining space and impressive chef's kitchen featuring newly upgraded high-end appliances, abundant cabinetry, and a massive quartz island that serves as the centerpiece of the space. A dedicated butler's pantry provides additional storage and convenience while keeping the kitchen beautifully organized. The home's interior has recently been professionally painted in a sophisticated neutral palette, creating a fresh and timeless backdrop throughout. Updated interior light fixtures further elevate the home's polished presentation. Built-in surround-sound speakers throughout the walls and ceilings enhance the entertainment experience, and all televisions convey with the property. Even better, the residence is being offered fully furnished with select exclusions, making it easy to begin enjoying your waterfront retreat from day one. Two additional bedrooms are located on the main living level, each featuring a walk-in closet with custom organization systems, along with one full and one-half bathroom. As you continue toward the third floor, a thoughtfully designed drop zone provides dedicated organization for coats, hats, shoes, and everyday essentials. The upper level is highlighted by an impressive primary suite showcasing stunning bay views. Step outside onto your private balcony for morning coffee overlooking the water or unwind at the end of the day while taking in the peaceful coastal setting. The spa-inspired primary bathroom features an oversized Roman shower, dual quartz-topped vanity, soaking tub, private water closet, and an expansive walk-in closet with custom organizers. Completing the third level is the home's fifth bedroom, currently utilized as a private office and offering flexibility for additional sleeping accommodations, a home workspace, or a quiet retreat. With its included boat slip, private pool and spa, multiple bay-view balconies, beautifully updated interiors, generous living spaces, high-end kitchen, and furnished presentation, this exceptional Bay Point Plantation residence offers a rare opportunity to enjoy waterfront living at its finest. Whether envisioned as a primary residence or an unforgettable coastal getaway, this is a home designed for making the most of life by the water. Boat slip #20 is part of Marina Condominium with a $821 annual fee.

10312 Plantation Ln, Berlin

Listing courtesy of Keller Williams Realty Delmarva. Contact: 4105246400
$697,500
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated canal-front home in West Ocean City, Maryland. This three bedroom, two bathroom home offers freshly renovated living spaces featuring brand new kitchen cabinets, countertops and appliances, new flooring throughout, and fresh paint from top to bottom. The primary bathroom has been updated with a walk-in shower as well as new cabinetry and countertops. Outside you have your own private canal frontage complete with a boat lift. The fully fenced backyard includes a charming patio sitting area, ideal for relaxing or entertaining. A one car attached garage adds everyday convenience. Move-in ready and full of possibility, this is a rare opportunity to own a slice of the Eastern Shore.

10362 Keyser Point Rd, Ocean City

Listing courtesy of AushCo Realty, LLC. Contact:

$749,900
4 Beds ⋅ 3 Baths
Beautifully maintained 4-bedroom, 3-bath home offering an exceptionally versatile floor plan in one of West Ocean City's most desirable areas. The main level features two bedrooms, including the primary suite, two full baths, a private office, and inviting living spaces with an open flow to the beautifully updated kitchen. The kitchen features new quartz countertops, a center island, a new refrigerator and microwave, abundant cabinetry, and a walk-in pantry. The first-floor primary suite includes a beautifully remodeled, spa-like bath with double vanities and an impressive oversized walk-in tiled shower. Upstairs you'll find two additional bedrooms, a full bath, and a spacious bonus room offering wonderful flexibility for a second living area, game room, media room, or guest space. Additional features include geothermal heating on the first floor, a heat pump serving the second level, new carpet in the living room and a new washer and dryer in the laundry room, conveniently located just off the garage. Outside, enjoy a peaceful, private wooded setting with a fenced backyard, rear deck, and hot tub—perfect for relaxing or entertaining after a day at the beach. Ideally situated in West Ocean City, this home offers the best of both worlds: a quiet residential setting while remaining just minutes from Ocean City beaches, Assateague Island, marinas, shopping, and some of the area's favorite waterfront restaurants. A wonderful opportunity to enjoy space, privacy, and the coastal lifestyle in a highly desirable location. Owners have an option to purchase a pool membership at the neighboring community of Mystic Harbor for $500 per year, offering an Olympic-sized swimming pool. Furniture may be available and is negotiable with an acceptable offer.

12514 Whispering Woods Dr, Ocean City

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500