329 houses for sale in Caine Keys

New Listing in Caine Keys II Extended Waterfront Corner Lot! Beautifully updated 3-bedroom, 2-bath home located on a desirable corner waterfront lot in Cane Keys II Extendedjust approximately 0.5 miles from Ocean Citys stunning beaches. This property is a boaters dream, featuring both a boat lift and jet ski lift, offering easy access to the water. Enjoy outdoor living at its finest with multiple spacious balconies and an upper deck showcasing gorgeous water views. The lower-level deck is fully shaded, creating the perfect entertainment space complete with a TVideal for relaxing after a day on the water or at the beach. A rare opportunity to own a move-in-ready waterfront home in a prime location close to everything Ocean City has to offer. Large lot. Possible add on potential / Some furniture will stay with home, ask agent for list

Experience elevated coastal living in this stunning luxury waterfront retreat in Ocean City. Offering 4 spacious bedrooms and 4.5 beautifully designed bathrooms, this recently updated home blends modern elegance with relaxed beachside charm. Soaring vaulted ceilings create an open, airy feel, while expansive living areas and oversized bedrooms provide comfort and flexibility for both everyday living and entertaining. The gourmet kitchen and spa-inspired bathrooms showcase high-end finishes and thoughtful design throughout. Step outside to your private tropical oasiscomplete with lush landscaping, full irrigation and drip systems, a stylish pergola, and a relaxing hot tub surrounded by vibrant greeneryperfect for unwinding after a day on the water. Boating enthusiasts will appreciate direct access to both the Atlantic Ocean and the scenic Assawoman Bay, along with two PWC lifts and a full powerboat lift, making waterfront living effortless. An attached garage adds convenience and additi

Welcome to this beautiful five-bedroom, two-and-a-half-bath single-family home in the sought-after Caine Keys II community of Ocean City, Maryland. Perfect for boaters and beach lovers alike, this home features a private boat slip right outside your back door, providing easy access to the water. Enjoy the coastal lifestyle with a large balcony offering scenic views, a cozy gas fireplace, and plenty of parking, Located just minutes from Ocean Citys stunning beaches, this home is ideal for year-round living or a relaxing vacation retreat. Dont miss this rare opportunity to own a spacious waterfront home in one of Ocean Citys most desirable neighborhoods! Home Extras: Central Vac, Gas stove, 2 large waterfront decks, gas fireplace, and in home stereo speakers. *new roof april 2026

103 Channel Buoy Road sits canal-front in the heart of Caine Keys II, one of North Ocean City's most coveted waterfront addresses. A private pier and boat dock sit steps from the back door, with the beach directly across the street — two of the Shore's most sought-after features on a single property. Inside, vaulted ceilings, skylights, and walls of glass create a bright, open atmosphere throughout, anchored by a stone gas fireplace in the great room. The kitchen features granite countertops and a full stainless steel appliance suite, and the waterfront deck offers generous space for outdoor living and entertaining. Four bedrooms, three full baths, and 2,248 square feet across a thoughtfully designed layout — no HOA. Major updates completed within the past two years include a new roof, water heater, appliances, pier, carpet, and all-new living room windows. Turnkey, fully furnished, and ready

Waterfront opportunity in a prime oc location! Bring your boat and your beach gear! Vinyl 60' Bulkheaded waterfront on a wide canal with direct water access, just minutes to open bay. Whether you're looking to cruise, fish, or kayak, you'll love having the water right out your back door, plus NO HOA means more freedom to enjoy your property. 3 bed, 2 full bath home with second floor loft for extra storage. Attached garage has storage above as well. Updates include NEW HVAC (2025), NEW appliances (2022), and NEW roof (2021). One of the best features? Channel Buoy Rd ends in a traffic light, giving you easy, safe access onto Coastal Hwy and easy cross to the BEACH. Great location in North OC close to restaurants, bars, shopping, and beach fun!

What happens when Ocean City stops numbering the streets and starts naming them? You find rare waterfront retreats like this house on Winter Harbor Dr. Tucked into the Caine Keys section of North Ocean City, just a few short blocks where the streets suddenly trade numbers for names, this waterfront cul-de-sac feels different than the rest of town. More relaxed. More personal. More like the version of beach life people remember. And people want more of. Affordable waterfront living! Its disappearing fast. 118 Winter Harbor is a 3-bedroom, 2-bath waterfront home offering direct canal frontage with immediate access to the Assawoman Bay, along with something buyers are struggling to find anymore a move-in-ready waterfront property, with a dock, at a price point that still feels attainable. The home itself has been thoughtfully updated and exceptionally well cared for, with coastal finishes, updated bathrooms, updated decor, a newer roof, updated vinyl bulkheading, and an updated rear deck

Caine Keys 2 Extended Direct Bayfront! Experience luxury waterfront living in this unbelievably gorgeous custom-built home, perfectly situated on the bay in Caine Keys 2 Ext, just approximately mile from the beautiful beaches of Ocean City. Built approximately five years ago and meticulously maintained by its original owner, this exceptional property features five bedrooms and five-and-a-half baths with upgrades and high-end finishes throughout. Enjoy boating and waterfront living with your private boat lift and updated bulkheading, all while taking in spectacular bayfront views. The outdoor space also includes a private swimming pool, perfect for relaxing or entertaining. Inside, the home offers beautiful hardwood floors, a stunning chefs kitchen, and luxuriously appointed baths designed with both comfort and style in mind. Additional features include two one car attached garages, offering ample space for vehicles, storage, or recreational equipment. This custom-built bayfront retreat

Welcome to 134 Old Landing Rd A Stunning Waterfront and Bay View Retreat! Experience waterfront living at its finest in this beautifully maintained Cap Code style home, offered fully furnished and ready for immediate enjoyment. Perfectly positioned along the canal with direct bay access, this spacious home offers breathtaking water views and unforgettable sunsets from multiple outdoor spaces. Plus a front entry ramp provides easy access to the home, adding both convenience and accessibility. The first floor features two comfortable bedrooms and a full bathroom, along with a convenient laundry area. The main living spaces include a bright kitchen, an inviting living room, and a second living area or a family room, ideal for gathering with family and friends after a day on the water. Upstairs, the second floor offers a spacious primary suite with a private bath, along with a versatile open sitting area and a large walk-in closet. This level also includes three additional bedrooms and ano

Waterfront Bungalow in Prestigious Caine Keys II Ext/(Seller would like to sell'As Is' but will allow a termite) Welcome to your dream coastal retreat in the exclusive community of Caine Keys II. Ext.This beautifully updated 3-bedroom, 2-bath waterfront bungalow perfectly combines relaxed coastal living with modern comfort. Enjoy breathtaking water views from your private backyard oasis, complete with a boat docking area and jet ski lift-ideal for those who love life on the water. Inside, you'll find a thoughtfully designed open layout featuring an updated kitchen, spacious living area, and plenty of natural light throughout. The home's seamless indoor-outdoor flow makes it perfect for entertaining or simply soaking up the tranquil waterfront ambiance. Located just a half mile from Ocean City's world-famous beaches, this property offers the best of both worlds-peaceful waterfront living with the ocean, restaurants, and entertainment just minutes away. Whether you're looking for a full-

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Seller offering owner financing. Call listing agent for details! 100k price reduction! 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 fireplace anchors the living

Presenting this finest and elegant, custom-built waterfront home, situated in the finest neighborhood in OC. This is truly an entertainer's paradise. You will find an open floor plan, that is wrapped in windows, offering majestic views. There are 4 BR and 3 BA, and a 35 Ft pier. First floor there are 2 guest rooms and can easily sleep 8 Guests. The main level is host to a large living room with Panoramic views. Gourmet Kitchen with all SS Appliances. This is a wonderful once in a life time opportunity to own the best of ocean city, Maryland. Come home to coastal living at its finest. Qualified Buyers Only, no Solicitation! This is a limited service listing: do not contact the listing agent. Contact the OWNERu002FSELLER directly

Remodeled and re vamped 2 bedroom 1 bath getaway in Summertime Park. Enjoy beautiful sunsets on the bay or walk across the street to the beach via the private path. New exterior siding, roof, windows, and decking. Brand new kitchen with bright white cabinets, stone counters, attractive back splash, stainless appliances, and recessed lighting. Newly upgraded bath, luxury vinyl plank throughout. Smartly furnished in a coastal style and move in ready! New sliding glass doors ($5000) and flooring are being installed in the family room. Park is open for April 1st until the second week of November. All prospective buyers need park approval. Ground lease $10,500 annually

Discover this great opportunity to own in the Montego Bay community of North Ocean City. This property features an oversized lot with no rear neighbor, offering added privacy and open space. It is a great building lot, and possible floor plans are included on file to help show potential layout options. The Montego Bay community features a variety of amenities, including pools, tennis courts, walking paths, and convenient access to North Ocean City attractions. Enjoy the benefits of a well-maintained neighborhood with a strong sense of community. Dont miss your chance to own in one of Ocean Citys most sought-after neighborhoods by the beach! Property being sold as-is. Please call listing office for lockbox details!

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 it completely turnkey and ready for

Discover this waterfront opportunity in the desirable Montego Bay community. Situated on a deep, well-protected basin, this property offers a private boat slip with southern exposure—ideal for boating enthusiasts and those who enjoy life on the water. The Montego Bay community offers an array of amenities, including pools, tennis courts and convenient access to shopping, dining, and the beach. Perfect as a year-round residence, vacation retreat, or investment property, this home combines the best of coastal living with a prime waterfront setting. Don’t miss your chance to own in one of Ocean City’s most sought-after waterfront neighborhoods. Property being sold 'as-is'. Home has new Au002FC, has been freshly painted and is located on a quiet cul-de-sac. Please call Listing Agent for Lockbox Code

Spacious 4BRu002F2.5BA home with den that could serve as a 5th bedroom! Well-maintained uptown property on a foundation with room for your finishing touches. Perfect as a year-round home or beach getaway with plenty of space for guests and entertaining. Great uptown location close to many local favorite restaurants, shopping, and attractions. Enjoy the amenities that Montego Bay has to offer including pools, tennis courts, walking and biking paths, plus extra storage with the backyard shed

A great opportunity to create your own space in the highly sought-after Montego Bay Community. You can either refresh this 2-bedroom, 1-bath home and make it your own, or you can start anew. This property is a few doors down from the community swimmingu002Ftennisu002Fmini golfu002Fshuffleboard complex. Property sold “As Is' Community amenities include 2 inground swimming pools, 1 kiddie pool, 2 tennis courts, pickle ball courts, shuffleboard court, a 9-hole mini-golf course a bayfront boardwalk with 3 fishingu002Fcrabbing piers, a wildlife sanctuary park area with large pond and a blacktop walkingu002Fjogging path all for $415.00 per year! A few blocks from the beach, dining, and Ocean City’s 58-acre North Side Park

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

Just reduced $100k and offering 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, butler's pantry, built-in drawer microwave, gas oven/range, and a premium refrigerator with on-demand hot water. A cozy gas fireplace anchors the living space

Welcome to 37630 W Shady Dr, a good sized 2 bedroom, 2 bath home, with room for a possible 3rd bedroom, in the desirable community of Shady Park, only about 3 miles from the beaches of Fenwick Island, DE and Ocean City, MD. This home has plenty of room for guests including 2 living areas and 1 with a fireplace. The kitchen has plenty of cabinet space, a breakfast bar and a good sized dining area. Both baths have walk-in showers. The community has a waterfront picnic area, playground, dog park and access to a boat ramp for a small annual fee. This home is close to shopping, restaurants, beach, bay, golf courses and Freeman Arts Pavilion, which hosts a Summer Concert Series featuring local and national acts

Welcome to 13309 peach tree road! This beautifully maintained custom-built waterfront home is located in the highly desirable, and sought-after, Montego Bay community in North Ocean City Maryland and is situated on a 600' plus wide canal offering deep water and quick and easy access to the open bay. The 1st floor features 3 bedrooms and 2 full baths-including an en suite in the primary bedroom, a great room with 16.5' high cathedral ceilings and a laundry room. The 2nd floor features a huge bonus room with a full bath and an abundance of storage space. Outside features include a 10 x 24 waterfront porch with cathedral ceilings and glass inserts in the railings, a pier with 2 slips, a high-end electric boat lift, a 40' waterfront ground level deck, a 5 x 18 finished off storage shed, a hot & cold enclosed shower, a cement patio and a 2-car cement parking pad. Additional features/upgrades include a kitchen island, granite countertops, ceramic backsplash, 42' cabinets, stainless steel app

Back on the market at no fault of the seller. Charming 2-bedroom, 1-bathroom home in the Shady Park community, just minutes from Fenwick Island. This well-maintained home offers a comfortable living room, a cozy den for extra gathering space, and a kitchen with a dining area. Enjoy coastal living with a screened porch and an outdoor shower—perfect for rinsing off after a day at the beach. Additional storage for all your beach needs is available in the backyard shed. Whether you're looking for a summer getaway or a year-round residence, this home provides a fantastic location and a relaxed lifestyle near shopping, dining, and the shore. Don’t miss the opportunity to schedule a private tour!