533 properties for sale in Dagsboro town

The potential is here! Major updates and renovations needed in this Coastal Contemporary 3-bedroom 2 Bath 1 level home with a short walk to the Golf Course and Clubhouse. Owner replaced the roof and all of the appliances including HVAC about 10 years ago. Owner is moving out and relocating in the area and might need time to vacate the property

Brand-new construction in the exciting Triple Crown neighborhood of Ocean Pines! This beautifully designed 4-bedroom, 3.5-bath home is currently under construction, with anticipated completion in 2026. The thoughtfully designed 3,348 sqft layout features a first-floor primary suite and an attached garage, offering both convenience and functionality. There's still time to customize select finishes and add your personal touch to this beautiful new home! See the documents for a complete list of features and finishes. Don't miss this opportunity to get in early and make it your own before construction is complete!

Rarely available! Top-floor southeast corner unit in the highly desirable West Winds condominium, where units rarely come on the market. This exceptional 1-bedroom, 1.5-bath condo offers unobstructed Southern Ocean views stretching down the beach and is ideally located on 93rd Street, close to popular restaurants, shopping, and all that Ocean City has to offer. At 682 square feet, this is one of the larger 1-bedroom oceanfront condos, and the southeast corner location provides an abundance of natural light and extra windows, creating a bright, open, and inviting atmosphere. The spacious living area is the perfect place to relax and enjoy the beautiful coastal views. The unit features updated flooring throughout, an updated kitchen with stainless steel appliances, and a convenient dining area. The spacious bedroom and updated bathroom complete this comfortable coastal retreat. West Winds is a well-maintained 30-unit condominium complex featuring an elevator, assigned parking space, and

Spacious and open floor plan designed for easy living and effortless entertaining. This inviting home features 3 generously sized bedrooms and 2 full baths. Sliding glass doors open to a large screened porch. The charming front porch is perfect for enjoying your morning coffee or relaxing in the evenings with your favorite beverage. Roof replaced in 2022 with 50 year warranty. Central Heat /AC for year round comfort. Abundant closet space and storage shed for all of your beach and boating essentials. You'll love being part of a vibrant waterfront community offering exceptional amenities including 5 pools, tennis, pickleball, yacht club, restaurants, Robert Trent Jones, Sr designed championship golf course as well as a beachfront pool, parking and restaurant in Ocean City. EVERYTHING you need to embrace the Coastal Lifestyle to the fullest. Ocean Pines is located just 5 miles inland from Ocean City and blends wooded serenity with Coastal Charm. Fresh paint, new carpeting in bedrooms. Le

Discover unmatched coastal living in this 5bedroom, 4.5bath waterfront retreat, perfectly positioned on a picturesque point along Greys Creek off Assawoman Bay. Offering 330 feet of private waterfront, this property delivers sweeping water views, unforgettable sunsets, and a rare blend of privacy, space, and tranquilityjust minutes from the ocean yet worlds away from the bustle. A gated entrance leads to an extended driveway and an impressive oversized 3car garage, designed with high ceilings ideal for vehicle stacking, storage, or hobby space. For boating enthusiasts, this is truly a boaters paradisecomplete with a private pier, boat lift, and effortless access to the creek and bay. Inside, the home is crafted for comfort and efficiency, featuring geothermal heating and cooling and generous square footage for hosting, relaxing, or working from home. Multiple rooms capture serene water views, including a striking panorama of the Ocean City skyline in the distance. Outdoor living shines

A rare opportunity to own directly on the bay in Ocean Pines with a view of Ocean City. Main living area is positioned on an upper level to take advantage of the full bay view. Main floor features the upstairs full kitchen, two bedrooms, one full bath and 1 12 bath. A laundry room completes this level. Located in Turns Landing, one of the most desirable water front proprties in Ocean Pines. Just minutes from several shopping centers. On Route 589. Convenient access to many amenities ncluding multiple pools, the Ocean Pines Beach Club in Ocean City, golf, tennis, parks, walking trails, and more

Welcome to the Ballyliffin Model, a beautifully crafted custom home built by Celtic Nations Contracting. Offering approximately 2,200 square feet, this thoughtfully designed home features four bedrooms, 3 baths, two en-suite bedrooms, and exceptional custom details throughout. Step inside to a spacious family room highlighted by an awesome fireplace, custom built-ins, a flat-frame TV, and decorative faux ceiling beams that add warmth and character. The family room flows seamlessly into the open-concept kitchen and dining area, creating the perfect space for everyday living and entertaining. The stunning coastal-inspired kitchen features quartz countertops, stainless steel appliances, a large farmhouse sink, floating shelves, and a generous island, all complemented by stylish finishes and thoughtful design. The first-floor en suite offers a beautifully designed custom closet and dressing area, along with a spacious private bath featuring distinctive tilework and a warm, relaxing ambianc

Cottage-style, picture perfect home. Located on a beautiful tidal pond with unobstructed open views of water, marsh, golf course, and offers significant privacy. (Update regarding tidal pond! Last saturday during my open house while out on back deck with visitors, much to our surprise, there came two kayakers out of the marsh's tidal creek! Asked where they came from, they said from the route 90 bridge. Asked how deep the pond is, the kayaker in the middle put his paddle down and said the pond was higher than the paddel; about 7 feet+. Deep at high tide. The one closer to the shoreline said he thought it was around 3-4 feet! )No one can build on the lot next door on right side of house. Meticulously maintained and so many updates and improvements have been made. Kitchen offers French Vanilla-colored custom cabinetry with PLENTY of cabinet space and walk-in pantry. Island features a maple cutting board counter top and granite flanks the other counters. Great room has 20' ceiling and a w

Brand new kitchen cabinets, stainless steel appliances, LVP flooring, carpet, and more! French Doors lead from the dining area to rear deck and yard. Guest bath includes ceramic tile floors, walls, and glass block. Primary bath features a tiled shower stall. Fresh paint, storage shed, vinyl siding and front entry deck. Located in the amenity-filled community of Ocean Pines, which is just a short drive to the beaches of Ocean City, Assateague Island National Seashore, and historic downtown Berlin!

A Charming Eastern Shore Cottage in the Heart of Ocean Pines, tucked into a beautifully landscaped setting. This custom-built 2004 cottage offers the character, warmth, and livability that make an Eastern Shore home truly special. With its inviting architecture, refinished hardwood floors, distinctive details, and wonderful indoor-outdoor flow, this is a home designed for both everyday living and relaxed coastal entertaining. The welcoming open floor plan centers around a comfortable kitchen and family room, where a commercial-grade gas range, abundant cabinetry, and gas fireplace create a natural gathering space. The dining area adds an unexpected touch of charm with its beautiful domed ceiling and special lighting. Refinished hardwood floors, now extended throughout the home, add warmth and continuity. The primary suite is a peaceful retreat with a spacious bath and walk-in closet. Two additional bedrooms and a full bath provide plenty of space for household and guests. A four-season

Welcome to 12740 Jarvis Road! A rare waterfront retreat set on 10.75 acres in Bishopville, MD. This spacious 4-bedroom, 3-bath home offers the perfect blend of privacy, open land, and direct water access. Enjoy endless outdoor possibilities with a beautiful pasture stretching across the front of the property, ideal for horses, hobby farming, or simply taking in the peaceful surroundings (a new tin roof was put on the barn in 2023). Out back, take advantage of your private waterfront lifestyle complete with a boat liftperfect for boating, fishing, and exploring the nearby waterways. New boards on the dock in 2024 and new boat lift in 2025. The home offers generous living space with a functional layout suited for both everyday living and entertaining. Brand new HVAC System and a new septic pump installed 2025. A detached 2-car garage provides ample storage for vehicles, equipment, or recreational gear. Whether youre looking for a full-time residence, weekend escape, or a property with ro

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 posi

BIGGER, BETTER BUT you better hurry if you want to pick your own colors! Photos are actually pictures of 83 King Richard the beautiful HUNTER I model that sold! The Hunter I model is the little brother of The Hunter II currently being built at 5 Jockey Court (also pending) and now on 7 Jockey Court with a larger footprint and on a larger lot (see house plans). Crafted by Ultimate Homes, LLC, this masterfully designed 4-bedroom, 2.5-bath with den/office all in this sprawling rancher located in the prestigious new section of Triple Crown Estates in Ocean Pines. Blending timeless craftsmanship with refined modern finishes, this residence offers an elevated lifestyle just moments from the coast. Inspired Design. Exceptional Comfort, From the moment you arrive, the homes commanding presence and architectural detail set the tone for what lies within. Built with 2x6 construction and topped with 40-year architectural shingles, the quality is evident at every turn. Inside, an expansive open-con

Open house, monday. November 2, 2026 12:00 pm. 1:00 PM List price is Opening Bid at the Online auction to be conducted on Auctioneers website. Bidding begins Saturday, October 31, & ends Thursday, November 5, 2026 @ 12:00 PM. Important Notice: There is a computer program glitch affecting auctions scheduled November 2-5. The auction time displayed in the top-right corner of each Featured Listing is incorrect by one hour. Please be sure to verify the correct auction start time in the listing details. Single-family home located in the Ocean Pines community of Berlin, Maryland, featuring three bedrooms, dedicated office space, two full bathrooms, and one half bath. The property offers separate living and dining rooms, a partially covered rear deck, a private driveway, and an attached one-car garage. Ocean Pines offers community recreational amenities, including golf, swimming pools, marinas, parks, and trails, with convenient access to Ocean City and downtown Berlin. Main Level Living room

In highly desirable Ocean Pines! This beautifully maintained and recently updated 3-bedroom, 2-bath home offers the perfect combination of comfort, outdoor living, and waterfront enjoyment. The kitchen features stainless steel appliances, and the updated bathrooms add a fresh, modern touch. The spacious layout is ideal for entertaining family and friends, while the huge screened-in porch and adjoining patio provide the perfect setting to relax and enjoy peaceful canal views. A private dock with a boat lift, making it easy to get out on the water and enjoy life on the Assawoman Bay. A storage shed provides plenty of room for boating and outdoor gear. Ocean Pines is an amenity-rich community offering multiple pools, a yacht club, beach club, golf course, tennis and basketball courts, playgrounds, and a skatepark. Conveniently located with easy access to Route 90 and just a short drive to Ocean Citys beaches, restaurants, and attractions, this home is a fantastic opportunity to enjoy the

Welcome to River Run, a gated golf course community in Berlin, Maryland! This gorgeous, turnkey 4-bedroom, 3-full-bath duplex with a spacious loft offers beautiful views of the Gary Player-designed River Run Golf Course, overlooking the green on the par-5 3rd hole. Tucked away in a private setting, this beautifully updated home is the perfect place to relax and enjoy the best of coastal living. The inviting enclosed porch, outdoor patio, and second-floor balcony provide multiple spaces to unwind while taking in the peaceful golf course views. Inside, you'll find stunning tile work in the updated bathrooms and the convenience of two primary suites, with one on each level. The versatile loft features a built-in desk, making it ideal for a home office, reading nook, or additional living space. River Run offers an incredible lineup of community amenities, including a bar and restaurant, swimming pool, fitness center, and pickleball and tennis courts. Conveniently located with easy access t

Turnkey living with flexibility, value & investment potential! 'AS IS' Move-in ready. Beautifully maintained. Exceptionally versatile. This thoughtfully updated condo presents an outstanding opportunity for buyers seeking comfort, convenience, and flexibility in todays discerning market. Whether you're looking for a primary residence, second home, vacation retreat, or investment property, this home offers the freedom to make it your own from day one. A major recent upgrade includes completely replaced flooring throughout the home, particularly throughout the entry level, creating a fresh, cohesive, and inviting interior. Because the property has been vacant, portions of the newly installed flooring may have a slight bounce or give underfoot due to the new underlayment/padding. This is a characteristic of the installation and is not indicative of a structural issue. Adding even more value and convenience, virtually everything currently in the property conveys with the sale, with the exc

Welcome to this beautifully maintained rancher in the desirable community of Ocean Pines! Offering 1,456 square feet of comfortable one-level living, this 3-bedroom, 2-bath home features a spacious open floor plan, tasteful updates, and LVP flooring throughout. Large windows fill the living spaces with natural light, while the generously sized kitchen offers plenty of cabinet and counter space along with stainless steel appliances, making it ideal for both everyday living and entertaining. A dedicated laundry room adds convenience and functionality. Step outside and enjoy your own private backyard retreat, complete with a full fence, spacious deck, shed, and firepit, creating the perfect setting for outdoor gatherings, relaxing evenings, and entertaining friends and family. A covered front porch welcomes you home, while the large driveway provides ample parking. As an Ocean Pines resident, you'll have access to an impressive array of community amenities, including multiple swimming poo

Welcome Home! Discover the perfect blend of comfort, style, and coastal living in this beautifully refurbished 3-bedroom home nestled in the desirable Ocean Pines community. Thoughtfully updated from top to bottom, this inviting home offers the fresh, modern finishes you love with the warmth and comfort that make a house feel like home. Step inside and imagine settling into a space where so much has already been done for you. The stunning new kitchen features quartz countertops, a custom backsplash, and stainless steel appliances, creating the perfect gathering place for morning coffee, family meals, and entertaining friends. Luxury vinyl plank flooring flows throughout the entire home, complemented by new light fixtures and a fresh, updated feel in every room. Both bathrooms have been beautifully renovated. The hall bath features a tub with a stylish tile surround and tile flooring, while the primary suite offers a touch of everyday luxury with his-and-hers vanities, a spacious custom

A coastal A-frame with character, extensive renovations, and access to one of the Eastern Shores most amenity-rich communities. Welcome to 49 Bramblewood Drive in Ocean Pines. This 3-bedroom, 1.5-bath home has been thoughtfully renovated from top to bottom while keeping the charm that makes an A-frame so distinctive. Inside, youll find all new flooring and walls, tongue-and-groove ceilings, shiplap and board-and-batten details, plus fully remodeled kitchen and baths. A loft area adds even more flexible space for guests, a home office, or a cozy retreat. The improvements go far beyond the finishes, with a new roof and soffit, new hot water heater, new front window, new front and rear doors, whole-house water filtration system, and brand-new front and rear decks. Then theres the Ocean Pines lifestyle. Residents have access to multiple pools, parks, playgrounds, racquet sports and pickleball, golf, the Yacht Club and marina, boat access, and even the Ocean Pines Beach Club in Ocean City.

Welcome to the beautiful River Run community, where life is good, and picturesque views of the golf course and the Saint Martins River surround you. Nicely landscaped grounds and a spacious front porch welcome you to the skylight-brightened foyer, leading to the 2-story cathedral ceiling in the delightful kitchen, featuring granite countertops and smudge proof stainless steel GE appliances. Luxury vinyl plank flooring shows off the living areas, including a dining area with triple window, and a living room with gas fireplace and sliding doors to the rear patio, overlooking the 9th fairway of the Gary Player designed River Run golf course. Sliding doors lead to a cozy screened porch from the first floor primary suite, which includes 2 organizer closets, gorgeous ceramic tile flooring, double granite vanity, and a 3x6 walk-in tiled shower. You will find another bedroom, full bath, laundry room, and single car garage with workbench and cabinets to complete the lower level. Extra Bonus. Go

Steps from the ocean and ready to enjoy or rent, this beautifully decorated Ocean City condo offers the perfect blend of coastal comfort, convenience, and investment potential. Offered partially furnished and turnkey, this three-bedroom, two-bathroom end-unit condo comfortably sleeps up to 8 guests and is an excellent rental opportunity. Located on the second floor of a well-maintained four-story ocean-block building, the condo offers great ocean views and an assigned private parking spacea highly desirable feature in Ocean City. Inside, the light-filled interior is decorated in tasteful coastal colors, creating a relaxed beach-inspired atmosphere. The condo was renovated in 2022 and features new luxury vinyl plank flooring installed in August 2026 and has in-unit stackable laundry. The inviting living room opens through sliding glass doors to a private deck, providing the perfect spot to sip your morning coffee while watching the sunrise over the Atlantic or unwind in the evening as t

Tucked away at the end of a quiet cul-de-sac in Ocean Pines, this inviting 3-bedroom, 2-bath ranch offers comfortable one-level living, a peaceful wooded setting, and numerous major improvements! Step inside to discover beautiful hardwood floors, vaulted ceilings, skylights, and a distinctive double-sided gas fireplace that adds warmth and character to the living spaces. The kitchen features white cabinetry and granite countertops, creating a bright and welcoming space. The primary suite includes a walk-in closet and private bath with an oversized shower. Two additional bedrooms, an updated hall bath, and a separate laundry room complete the convenient single-level layout. Enjoy the privacy of a backyard backing to trees, whether relaxing on the screened porch or entertaining on the low-maintenance deck. An attached two-car garage provides additional storage and convenience. Major improvements include a new roof (2025), siding (2021), windows (2018), and dual-fuel HVAC system (2018) va

Seller offering $20,000 towards a 2-1 interest rate buy down with an acceptable offer. Comfort, privacy, and waterfront living come together in this fully renovated three-level contemporary home, ideally positioned along one of the quietest canals in Ocean Pines with direct access to the bay and beaches of Ocean City. Offering 4 bedrooms, 3.5 baths, and approximately 3,250 square feet, this exceptional residence has been thoughtfully updated to provide the perfect blend of coastal comfort, functionality, and entertaining space. Designed with an open-concept layout, the home features soaring vaulted ceilings, skylights, and expansive windows that fill the interior with natural light while showcasing tranquil water views from all three levels. Multiple gathering areas throughout the home allow family and guests to comfortably spread out, including a spacious great room, waterfront den, and bar area adjacent to the kitchen. The middle level also offers a private guest suite with en suite

Welcome to 80 Cresthaven Drive in the desirable community of Ocean Pines! This beautifully refreshed three-bedroom, two-bath home offers a wonderful blend of comfort, character, and thoughtful updates. Recent improvements include a new roof in 2023, HVAC replacement in 2022, freshly painted interior and exterior, reclaimed hardwood flooring in the living room and kitchen, updated bathroom vanities, new light fixtures, and additional lighting throughout. The inviting living room features a charming wood-burning fireplace, creating the perfect gathering spot on cool evenings and adding warmth and character to the home. Just beyond the living space, the large screened-in porch provides an ideal setting for morning coffee, relaxing evenings, entertaining friends, or gathering for a classic Maryland crab feast. Located in Ocean Pines, residents can enjoy an impressive variety of amenities, many of which are available la carte for an additional fee. This flexible approach allows you to choos

Brand-new and move-in ready, 5 Seattle Slew Lane is a single-level coastal rancher in Triple Crown Estates, one of the newest sections of Ocean Pines. Built by local builder Del Mar Construction, this 4-bedroom, 2.5-bath home offers approximately 2,103 finished square feet on a 0.32-acre lot backing to open common area. A double-door entry opens to vaulted ceilings, wainscoting, and luxury vinyl plank flooring throughout an open living, dining, and kitchen layout. The kitchen features quartz countertops, a large center island with breakfast bar, a pantry, and stainless ENERGY STAR appliances. The primary suite offers a tray ceiling, dual walk-in closets, and a spa-style bath with a freestanding soaking tub, frameless glass walk-in shower, and double vanity. Three additional bedrooms, a full hall bath, a powder room, and main-level laundry complete the plan. Step outside to an oversized front porch and a screened rear porch. Additional highlights include an oversized two-car garage with

This property offers a front row seat to resort style luxury every day with breathtaking, panoramic views of the nicely manicured golf course and shimmering ponds. Large windows perfectly frame this picturesque backdrop, offering a feeling of vast space and privacy. Enjoy your morning coffee or evening cocktails on the deck, while watching the sun shine on the peaceful waters in your own backyard oasis. The entire interior has been tastefully remodeled to include luxury vinyl plank flooring, tub showers, built-in shelving, stainless steel appliances, upgraded countertops, up-to-date ceiling fan, ship lap and bead-board walls, all while maintaining the original aesthetics such as wooden beamed ceilings and wood burning fireplace. Designed for effortless hosting, the lower level family room serves as an entertainment hub. At its heart is a custom, natural wood bar, a dedicated wet bar, and a mini refrigerator to keep refreshments perfectly chilled. Includes high-quality, unique furnishin

Buyers failed to sell their home. Tucked along the canal in the sought after community of Ocean Pines, this charming A-frame retreat blends rustic cottage character with the laid back waterfront lifestyle youve been dreaming of. With soaring vaulted ceilings, oversized windows, and an open layout designed to capture natural light and tranquil water views, this home is ready for relaxing weekends, family gatherings and entertaining after a day on the water. Step outside to enjoy the expansive wraparound deck overlooking the canal, the perfect place for morning coffee or evening sunsets. Boaters will appreciate the shared dock with a dedicated private slip for the home, offering easy access to the water. A cozy fireplace adds warmth and charm to the inviting living space, while the garage provides additional storage for all your beach and boating essentials. The main level features two bedrooms, a full bathroom, and a convenient laundry closet. Upstairs, the loft overlooks both the water

Waterfront luxury | 73' bulkhead | boat lift | bay access | 2.5-car garage | ocean pines! Experience the best of Eastern Shore waterfront living at 14 Goldeneye Court, an exceptional 4-bedroom, 2.5-bath residence in the desirable Wood Duck I community of Ocean Pines. Set on a generous waterfront lot with 73 feet of bulkhead, a private boat lift, and direct access to the bay, this property is designed for those who appreciate boating, beautiful water views, and an elevated coastal lifestyle. From sunrise over the water to evening gatherings on the expansive outdoor spaces, the setting is truly the centerpiece of this home. Multiple decks, balconies, and gathering areas provide exceptional opportunities to relax, entertain, and enjoy the waterfront. The second-level sun deck offers sweeping water views and an impressive vantage point for taking in the surrounding coastal landscape. Inside, soaring ceilings, abundant natural light, and an open-concept floor plan create a spacious and invi

We're going to call this canal-front because technically, that's what it is. Just don't expect it to look like most canal-front homes in Ocean Pines! Walk out back and you'll understand the difference. Instead of staring across a narrow canal at another row of homes, the water (and views) open up considerably. With no homes blocking your view, you're given a stunning view of the Ocean Pines Golf Course, and beyond. Plus, you get the boating access you're looking for in a waterfront home. Let's move on to the house itself. At approximately 2,500 square feet, this 3-bedroom, 3-full-bath home gives you something else that's surprisingly difficult to find on the waterfront in Ocean Pines: SPACE. There's a true two-car garage, generous living areas, a three-season room overlooking the water, and a large first-floor deck that turns the backyard into a pretty compelling reason to spend more time outside. Plus, the interior has been extensively renovated with a new kitchen, new bathrooms, new