469 properties for sale in Caine Keys

Relaxed coastal living takes center stage in this inviting North Ocean City home, where comfortable interiors, fantastic indoor-outdoor living, and an enviable Montego Bay location create the perfect setting for enjoying life at the beach. An expansive open-concept main living area brings together the living room, dining area, and kitchen beneath a cathedral ceiling, creating a bright, connected space for everyday living and gathering. A beautiful fireplace anchors the living room, while an additional sitting area provides a comfortable spot to relax and unwind. The dedicated dining area offers plenty of room for meals with family and friends, and the adjoining kitchen features stainless steel appliances, ample cabinetry, recessed lighting, and a center island with breakfast bar seating. Three bedrooms are conveniently located on the main level, including a primary suite with a private en suite bath. Two additional bedrooms share a full hall bath. A spacious laundry room adds tremendou

Welcome to 181 Jamestown Road #5, a rare opportunity to own a 2-bedroom, 2-bath direct bayfront condo offering an owners entrance and rear bayfront entrance, a private boat slip in the heart of Ocean City. A true boaters paradise, this waterfront retreat offers easy access to the bay and endless days on the water. With low condo fees, no current assessments, and sweeping panoramic views, this property boasts what is arguably one of the most spectacular waterfront views in all of Ocean City, MD. Inside, the charming nautical theme provides the perfect dcor, complementing the coastal setting and creating a relaxed waterfront atmosphere. A spacious living room opens to the dining area and galley style kitchen, offering plenty of cabinet storage and countertop prep spaces to create all your coastal favorites. This exceptional bayfront setting offers the quintessential Eastern Shore lifestyle, drop a crab pot from your pier and enjoy an abundance of fresh Maryland blue crabs right outside y

Beautifully maintained 2nd floor 2-bedroom, 2-bath condominium in quiet North Ocean City, offering comfort, convenience, and an easy coastal lifestyle. This move-in-ready home features numerous updates, including luxury vinyl plank flooring, sleek granite countertops, a stylish tiled backsplash, updated bathrooms, and more. The oversized 24' x 6' private balcony provides a peaceful retreat with an ocean peek and convenient access from both the primary bedroom and family room. A separate utility room includes a full-size washer and dryer, along with additional shelving for extra storage. The well-maintained building is scheduled to receive a new roof, and the outdoor pool has recently been resurfaced. Each unit also includes two parking spaces. Ideally located just a short walk from the beach, restaurants, shopping, and other popular Ocean City amenities. Most everything you see conveys with the sale, making this a truly turnkey opportunityjust bring your suitcase and start enjoying the

Located in the highly sought after community of Montego Bay in North OC, this 2 Bedroom 1-1/2 Bathroom home is being sold fully furnished and ready for you to move right in. Whether you're looking for a full-time residence, a vacation retreat, or an investment property, this one checks all the boxes. Conveniently located within walking distance to the beach, community amenities, shopping, dining, mini-golf, the bus stop, and Ocean City's 58-acre Northside Park. Home of the 4th of July Fireworks! Community amenities include 2 inground swimming pools, 1 kiddie pool, 2 tennis courts, pickle ball courts, a shuffleboard court, a 9 hole mini-golf course, a bayfront boardwalk with 3 fishing/crabbing piers, and an 8 acre wildlife sanctuary that has a pond with a blacktop walking/jogging path. All for a low hoa fee of $415.00 a year!

Stop scrolling! This is the turnkey beach opportunity you have been waiting for! Located one the first floor of the Balmoral Cove VII, featuring 3 bedrooms and 2 full bathrooms, this spacious Ocean City condo is ideally located within walking distance of the beach. Spend your days soaking up the sun, relaxing by the community pool, or enjoying some of Ocean Citys best dining and entertainment nearby. This property has been thoughtfully updated and well maintained, with new flooring throughout and a new water heater installed in 2021. Additional improvements include a new HVAC system in 2022; replacement sliding glass doors and rear bedroom windows in 2023; fresh interior paint throughout most of the condo and new bedroom furniture in 2024; and a beautifully remodeled rear bathroom in 2025. Recent appliance upgrades include a new stacked washer and dryer, refrigerator, and microwave, along with a new kitchen table. Whether you are searching for a personal beach retreat, a second home, o

Discover the charm of CLUB OCEAN VILLAS, with all the conveniences to enjoy life at the beach in this delightful 1st floor 2-bedroom, 2-bathroom unit is just 2 blocks to the ocean. Open floor plan with 864 sq. Ft. that features a spacious layout with private bedrooms & bathrooms on each side of living area. The kitchen is equipped with a built-in microwave, dishwasher, electric oven/range and wall pantry. The master bathroom features a walk-in shower. A stacked washer and dryer is conveniently located off the kitchen area. Step outside to enjoy your private enclosed courtyard perfect for relaxing, entertaining or extra storage. Chill & refresh by the community outdoor pool, ideal for sunny afternoons and a break from the beach. HVAC replaced within last 3 years. Located on 120th St on the bay side within 1 block to restaurants, grocery store, shops, drug store and other services. Plus, you'll enjoy the proximity to North Side Park on the water front, perfect for leisurely strolls fishi

Well-maintained waterfront condo with a pool and short walk to the beach in Ocean City, Maryland. This condo offers one bedroom, one full-bathroom, an open living area and a private waterfront balcony. The living area features a comfortably furnished living room and a fully-equipped kitchen with a convenient breakfast-counter. There is a good-sized, private balcony located off of the living area with favored southern exposure. This is a great place to relax, unwind and enjoy the nice waterfront setting after a long day on the beach or out on the water. The bedroom is generously sized, providing for a variety of configuration options depending on your needs. The full-bathroom is centrally located and easily accessible from throughout the condo. Community amenities include onsite parking, outdoor pool and outside showers. The communitys prime location is within walking distance to the beach, restaurants, shopping, coffee shops, amusements, Northside Park and more. The condo conveys fully

No condo fees*no hoa fees*. Comparable units with condo fees could pay an average of $50,000 more over 10 years. This bay front townhome has 2 bedrooms, 1.5 baths, 1st and 2nd floor decks and private parking. Inside you'll find a newly remodeled kitchen with granite counters, stainless steel appliances and luxury vinyl plank flooring that runs throughout the main level. The views of the bay and sunsets are gorgeous! 163b jamestown rd sold for $500,000

Bayfront Beauty in Ponte Vista Endless Views & Gorgeous Sunsets! Welcome to your perfect coastal getaway in Ponte Vista! This beautifully maintained 1-bedroom, 1-bath bayfront condo offers endless bay views and breathtaking nightly sunsets from your spacious private balcony. Enjoy your morning coffee overlooking the water or unwind in the evening as the sky lights up with spectacular coastal colors. The unit features updates including a newer hot water heater, stainless steel appliances, and laminated flooring, making it comfortable and ready to enjoy. With a great rental history, this condo is an excellent investment opportunityor keep it all to yourself as your own beach retreat! A storage closet is on each floor with individual caged areas to store all your beach belongings or bikes in the off season. Basic cable & wifi are included in the condo fee! The well-maintained building offers an outdoor pool, storage, and elevator access for added convenience. Boat slips may be rented thro

Welcome to 162 Sunshine Ln in Montego Bay, you're new retreat at the beach! As you arrive, the marigold exterior transports you to a laid back era that continues into the retro-styled interior. Decks on both sides of the home offer a relaxing outdoor atmosphere along with two koi ponds. On those rainy days, there is also an enclosed patio area near the entrance to enjoy. This home has three separate bedrooms and an additional flex space by the back door that provides plenty of places to sleep. A private shed out back offers plenty of storage for all of your beach supplies. New flooring throughout the entire home including new 3/4' subflooring and repaired floor joists. The refrigerator was also replaced in 2025. With an excellent rental history, this home can offer additional income while being your beach escape. Come take a look at this home today!

Top-floor water front living with 180 water views boat slips 24-ft balcony! Experience the very best of coastal living from this top-floor 2-bedroom, 2-bathroom waterfront condominium, where sweeping 180-degree views stretch from the open bay to Northside Parks spectacular Sunday night fireworks and all the way toward the ocean. Water views and refreshing breezes surround you for a perfect waterfront lifestyle. Vaulted ceilings create an airy, spacious feel, while recently installed luxury vinyl plank flooring flows seamlessly throughout the main living areas. The nicely appointed kitchen features stainless steel appliances and a custom island that opens effortlessly to the dining and living spaces and extends the entertaining area onto the massive 24-foot waterfront balcony. The large balcony is designed for year-round enjoyment, enclosed with vinyl sliding panels that stack completely open for warm-weather living and close comfortably for the cooler months. Whether youre enjoying mor

Tucked within the sought-after Club Ocean Villas II community, this inviting two-bedroom, two-bath condominium embodies the easygoing lifestyle that has made North Ocean City a favorite destination for generations. Thoughtfully designed to maximize both comfort and functionality, the bright interior features an open living, dining, and kitchen layout with low-maintenance ceramic tile flooring, creating a welcoming space for relaxing after a day at the beach or gathering with family and friends. The private primary suite offers its own full ensuite bath, while the second bedroom is conveniently situated near an oversized hall bath complete with a soaking tub and separate walk-in shower, ideal for rinsing away the sand after long days by the ocean. The well-equipped kitchen includes a pantry for added storage, and an in-unit washer and dryer provide everyday convenience. One of the home's standout features is its exceptional outdoor living space. The spacious, fully fenced patio and deck

Professional pictures to follow: Beautiful 1BR/1BA condo in Bluewater East with ocean views is now on the market and being sold fully furnished! The spacious bedroom provides plenty of room to relax, while the updated bathroom features a convenient walk-in shower. Located in the desirable south building, Bluewater East offers a community pool and a convenient location close to the beach, restaurants, and shopping. Condo also has a storage closet for your beach gear

This waterfront townhome with a deeded boat slip has been completely renovated inside and out including updated kitchen cabinets, stainless appliances, granite countertops, LVP flooring throughout and vinyl sliding doors and windows. The 1st level features an open floor plan with kitchen, dining area, living room, a half bath and laundry closet. The living room sliding door leads you out to a private composite deck with vinyl handrails and black aluminum balusters, and a deeded boat slip plus use of a bonus slip. The 2nd level features 2 large bedrooms and a shared updated bathroom. The waterfront bedroom features a balcony overlooking the canal and is spacious enough for a king sized bed with plenty of closet space. The 2nd bedroom is roomy enough for a queen and twin beds. This end unit provides you with bonus features including some open bay views and open outdoor space by the community picnic table. Home is being sold partially furnished and offers 2 assigned parking spots, allowin

Waterfront Condo with Private Boat Slip in North Ocean City Rare Canal-Front Opportunity. Experience the best of coastal living in this beautifully maintained waterfront condo in North Ocean City, featuring 30 feet of canal frontage and a private boat slip that conveys with the sale. Located on the first floor for easy access and convenience, this spacious 3-bedroom, 2-bath residence offers the ideal blend of comfort, boating lifestyle, and investment potential. Lovingly cared for by the original long-term owners and never used as a rental, this move-in-ready property stands apart from many waterfront offerings in Ocean City. The open floor plan is designed for relaxed beach living, while the generous primary suite overlooks the canal, creating a peaceful waterfront retreat. Step outside to enjoy composite decking, wood railings, a vinyl bulkhead, and an electronic awningthoughtful upgrades that enhance both enjoyment and durability. From your private slip, enjoy direct bay access for

Welcome to your dream getaway or primary residence! This beautifully updated 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and coastal charm. Enter into your own private fence to find an enclosed courtyard/patio area, perfect for leaving your beach chairs for your next beach day, your bicycle, or create another outdoor living space if you wish. Steps from here take you onto the 2nd floor where you will access the beautiful condo. As you enter, you are greeted by the spacious living room, which is open to the kitchen. Off of the living room, youll find the primary bedroom featuring a private ensuite, currently utilized as a guest space. The second bedroom boasts a sliding glass door that opens to your own private spacious deck/balcony, inviting you to enjoy your morning coffee or unwind in the evenings with the salty air on your skin. There have been many updates in the past few years including: new vinyl plank flooring, beautifully remodeled bathrooms, new HVAC in 2018,

Welcome to the Tiburon I located in Caine Woods in North Ocean City, where quiet coastal living meets unbeatable convenience. Nestled in a peaceful neighborhood just moments from the beach, dining, and entertainment, this fully furnished 2 bedroom, 2 bath condo offers the perfect blend of relaxation and accessibility. Recent upgrades include new flooring, updated primary shower, new bath tub and shower in secondary bathroom, new roof, new HVAC system, and new hot water heater, providing both style and peace of mind. Enjoy a spacious layout with a private balcony and a strong rental history, making it ideal as a second home or investment property. Community amenities include an outdoor pool, tennis courts and a beautifully maintained courtyard adding to the appeal of this sought-after uptown location

Bayside Living in Ocean City First-Floor Condo Near the Beach! Enjoy the best of coastal living in this 1-bedroom, 1-bathroom first-floor condo located on the bayside of Ocean City! Featuring an open floor plan that creates a comfortable, inviting living space, this condo offers a functional layout perfect for a beach getaway, weekend retreat, or year-round living. The kitchen features black appliances and flows seamlessly into the main living area, while the in-unit stackable washer and dryer add everyday convenience. Step outside to enjoy the front porch, a great spot to relax and unwind after a day at the beach. Conveniently located near Ocean City's beaches, shopping, restaurants, and local attractions, this condo offers easy access to everything the area has to offer. Whether you're looking for your own coastal escape or a place to enjoy all that Ocean City has to offer, this property is full of possibilities!

Front-row seats to paradise! Discover the magic of direct open-bay living on 511 Harbour Drive, where breathtaking panoramic sunset views, endless sparkling waters, and refreshing coastal breezes turn every day into a waterfront getaway! Located in Ocean City's highly sought-after Montego Bay Community, this coastal gem offers an incredible opportunity to own a piece of waterfront paradise! Imagine relaxing on your expansive waterfront deck as the evening sky transforms into a spectacular display of brilliant colors reflecting across the open bay. These are the kind of sunsets you'll never get tired of watching! Be sure to check out the spectacular aerial drone photos! These breathtaking bird's-eye views showcase the property's incredible direct open-bay location, expansive waterfront setting, and surrounding coastal beauty. One look from above and you'll understand why this location is so special! Situated on a 3,610-square-foot lot with a vinyl bulkhead installed in 2016, this proper

Back-up offers will be considered*. Welcome to 8901 Rusty Anchor Road #C, a rare opportunity to own a spacious 3 bedroom, 3 full bath condo in the highly sought after Little Salisbury neighborhood of North Ocean City. Offering nearly 1,900 square feet across two thoughtfully designed levels, this home delivers the space, layout, and flexibility that is so hard to find at the beach. The main level features a bright and open living area along with a full bedroom and bathroom, perfect for guests or easy one level living. Upstairs, you will find two additional bedrooms, each paired with their own full baths, creating ideal separation and privacy for owners and guests alike. What truly sets this property apart are the three oversized balconies, each offering incredible bay and canal views. Whether you are starting your morning with coffee at sunrise or winding down in the evening with a sunset, this home gives you front row seats to both. This property is being sold fully furnished, making

Waterfront Living Awaits at Barbados Sun! This beautifully appointed 2-bedroom, 1-bathroom condo in Barbados Sun features 909 square feet of comfortable coastal living just off 94th Street. Offered fully furnished, this inviting retreat showcases lovely bay views and includes a deeded boat slip with lifta fantastic bonus for boating enthusiasts looking to embrace the waterfront lifestyle. Adding to the convenience, the condo complex offers a separate storage area for bikes, kayaks, and beach gear, making it easy to keep all your coastal essentials organized and ready for your next adventure. Whether you're searching for a relaxing beach getaway, an investment opportunity, or your own coastal escape, this condo offers the ideal blend of comfort, convenience, and boating access. Enjoy the best of coastal living with beautiful bay views and easy access to the surrounding beach area. Don't miss your opportunity to own a piece of the coastal lifestyle at Barbados Sun!

Welcome to 181 Jamestown Road #4, a rare opportunity to own a beautifully updated 2-bedroom, 2-bath direct bayfront condominium with a private boat slip in the heart of Ocean City. Offering both an owners entrance and a rear bayfront entrance, this waterfront retreat places you just steps from the water. A true boaters paradise, the property offers convenient access to the bay along with sweeping panoramic views that are arguably among the most spectacular in Ocean City, Maryland. Low condo fees and no current assessments add even more appeal to this exceptional waterfront property. Inside, the home has been tastefully updated throughout and is being sold furnished with minor exclusions, making it easy to settle in and immediately begin enjoying the coastal lifestyle. Luxury vinyl plank flooring, crown molding, plantation shutters, a stylish barn door, and a cozy pellet stove add character and comfort, while the updated kitchen and baths provide a fresh, polished feel. The beautifully

Welcome to the coastal lifestyle you've been waiting for in the sought-after Montego Bay community of North Ocean City! This spacious. *double-wide home offers 3 bedrooms and 2 full baths*, providing plenty of room for family, friends, and weekend guests while putting you close to everything that makes Ocean City living special. Whether you're searching for a beach getaway, seasonal retreat, or a place to enjoy the relaxed coastal lifestyle, this home offers an incredible location just. *three blocks from the beach*. Spend your mornings with your toes in the sand, your afternoons exploring the area, and your evenings enjoying everything North Ocean City has to offer. Outdoor enthusiasts will love being just minutes from. *Northside Park*, where you'll find walking and biking paths, fishing, kayaking, sports fields, an outdoor fitness area, playgrounds, and seasonal events including the popular Sundays in the Park. Nearby, enjoy miniature golf, local restaurants, shopping, and easy acce

Timeshare opportunity in uptown Ocean City! Interval E features a 2-bedroom, 2-bath unit with a private balcony overlooking the waterthe perfect place to relax and enjoy the coastal setting. The property also offers a shared dock with private access for residents. Conveniently located on 120th Street, youll be close to the beach, popular restaurants, bars, shopping, and entertainment. Enjoy the best of Ocean City with both the beach and the bay lifestyle right at your fingertips. Dont miss this affordable opportunity to own your piece of Ocean City!

Welcome to your waterfront retreat in the highly desirable Caine Woods community of North Ocean City! This beautifully updated 2-bedroom end-unit townhome offers the perfect combination of coastal charm, modern updates, and canal-front living. Inside, you'll find wood laminate flooring throughout, creating a warm, cohesive look that's both stylish and easy to maintain. The updated kitchen features granite countertops, a stunning backsplash, stainless steel appliances, and plenty of cabinet space, while the renovated bathroom boasts tile flooring, a spacious tiled walk-in shower and an attractive vanity. Step outside and enjoy peaceful canal views from your southern exposure waterfront deck, with dock access providing the perfect opportunity for boating, kayaking, paddleboarding, or simply relaxing by the water. The community has also benefited from major improvements, including a new bulkhead, expanded dock, and low-maintenance composite decking. Parking is a breeze with one assigned p

Motivated seller just reduced another $100k and offering 5% owner financing. Call listing agent for details! Bring your buyers and offers for this beautiful new construction home nestled within the prestigious Lighthouse Sound community! This exceptional 2025 new construction residence offers the perfect blend of coastal elegance, natural beauty, and modern luxury. Set on an expansive 1.22-acre private oasis homesite, the property is surrounded by lush trees, tidal wetlands, and open lowlands, delivering daily wildlife sightings and breathtaking sunset views over the bay and the scenic landscape of Worcester County. Designed for both refined living and effortless entertaining, the open-concept layout seamlessly connects the gourmet kitchen to the inviting family room. The kitchen is a true showpiece, featuring solid surface countertops, an oversized island, butlers pantry, built-in drawer microwave, gas oven/range, and a premium refrigerator with on-demand hot water. A cozy gas firepla

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

Turnkey Waterfront Retreat with Dock Access Near the Beach Beautifully updated and fully furnished, this turnkey North Ocean City retreat offers elevated coastal living close to the beach, dining, shopping, and the Delaware line. Featuring two bedrooms, one-and-a-half baths, and two levels of inviting indoor and outdoor living space, it is designed for effortless relaxation and entertaining. Enjoy peaceful canal views from the south-facing waterfront deck, along with dock access for boating, kayaking, paddleboarding, or simply unwinding by the water. The nearby crosswalk provides convenient beach access, while Gorman Park is just around the corner for pickleball, recreation, and dog walking. Located outside the R-1 district, the property offers added flexibility for owners and investors. With a proven rental history and established income potential, this ideally located coastal retreat is an exceptional opportunity as a second home, investment property, or personal beach getaway

Direct Bayfront, one-bedroom, one-bath condo in midtown Ocean City. Building is located on Jamestown Rd, just across the street (1.5 blocks and a 34-minute walk) from the beach and Atlantic Ocean. Enjoy early morning sunrise or your evening sunsets from the balcony. The Harbor Sails complex features an outdoor pool, tennis courts and an elevator. There is one unassigned parking spot. You can take a leisurely stroll to nearby attractions such as the Gold Coast Mall, Fox Gold Coast Movie Theater and Greene Turtle, or the Carousel, which offers ice-skating to the public. Also, within walking distance are many restaurants

Huge price improvement! Enjoy waterfront living at its finest in this beautifully situated 2-bedroom, 2-bath condo right off of 94th Street in Ocean City! Featuring a spacious and functional layout, this coastal retreat offers beautiful canal views and a large waterfront deckperfect for relaxing, entertaining, or enjoying your morning coffee by the water. Sliding glass doors from both the primary bedroom and living room provide easy access to the deck and bring the waterfront setting right inside. Boaters will love the opportunity for a boat slip for just $200 per year, making it easy to enjoy everything Ocean City has to offer by land and water. The condo is being sold fully furnished (See exclusions list), making it ready to enjoy from day one. With low condo fees and professional management, this is a fantastic opportunity for a beach getaway, investment property, or year-round coastal home!